Organisation for Economic Co-operation and Development

Unclassified

ENV/CBC/MONO(2022)1
English - Or. English
18 January 2022

ENVIRONMENT DIRECTORATECHEMICALS AND BIOTECHNOLOGY COMMITTEE

Fact Cards of Major Groups of Per- and Polyfluoroalkyl Substances (PFASs)
Series on Risk Management
No. 68JT03488355
OFDE

This document, as well as any data and map included herein, are without prejudice to the status of or sovereignty over any territory, to thedelimitation of international frontiers and boundaries and to the name of any territory, city or area.

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FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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ENV/CBC/MONO(2022)1  3OECD Environment, Health and Safety Publications
Series on Risk Management
No. 68Fact Cards of Major Groups of Per- andPolyfluoroalkyl Substances (PFASs)

Environment Directorate
ORGANISATION FOR ECONOMIC CO-OPERATION AND DEVELOPMENT
Paris 2022

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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About the OECDThe Organisation for Economic Co-operation and Development (OECD) is an intergovernmentalorganisation in which representatives of 38 industrialised countries in North and South America,
Europe and the Asia and Pacific region, as well as the European Commission, meet to co-ordinate
and harmonise policies, discuss issues of mutual concern, and work together to respond tointernational problems. Most of the OECD’s work is carried out by more than 200 specialisedcommittees and working groups composed of member country delegates. Observers from several
countries with special status at the OECD, and from interested international organisations, attend
many of the OECD’s workshops and other meetings. Committees and working groups are servedby the OECD Secretariat, located in Paris, France, which is organised into directorates anddivisions.
The Environment, Health and Safety Division publishes free-of-charge documents in twelve
different series: Testing and Assessment; Good Laboratory Practice and Compliance
Monitoring; Pesticides; Biocides; Risk Management; Harmonisation of Regulatory Oversightin Biotechnology; Safety of Novel Foods and Feeds; Chemical Accidents; Pollutant Release
and Transfer Registers; Emission Scenario Documents; Safety of Manufactured
Nanomaterials; and Adverse Outcome Pathways. More information about the Environment,
Health and Safety Programme and EHS publications is available on the OECD’s World Wide Web
site (www.oecd.org/chemicalsafety/).

This publication was developed in the IOMC context. The contents do not necessarilyreflect the views or stated policies of individual IOMC Participating Organisations.
The Inter-Organisation Programme for the Sound Management of Chemicals (IOMC) wasestablished in 1995 following recommendations made by the 1992 UN Conference on
Environment and Development to strengthen co-operation and increase international coordination in the field of chemical safety. The Participating Organisations are FAO, ILO,
UNDP, UNEP, UNIDO, UNITAR, WHO, World Bank and OECD. The purpose of the
IOMC is to promote co-ordination of the policies and activities pursued by theParticipating Organisations, jointly or separately, to achieve the sound management ofchemicals in relation to human health and the environment.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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ENV/CBC/MONO(2022)1  5This publication is available electronically, at no charge.
Also published in the Series on Risk Management link
For this and many other Environment,
Health and Safety publications, consult the OECD’s
World Wide Web site www.oecd.org/chemicalsafety/
or contact:
OECD Environment Directorate,
Environment, Health and Safety Division2, rue André-Pascal
75775 Paris cedex 16
FranceFax : (33-1) 44 30 61 80
E-mail : ehscont@oecd.org© OECD 2022
Applications for permission to reproduce or translate all or part of this material should be made to: Headof Publications Service, RIGHTS@oecd.org, OECD, 2 rue André-Pascal, 75775 Paris Cedex 16, FranceOECD Environment, Health and Safety Publications

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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Acknowledgements: These fact cards were prepared under the framework of the
OECD/UNEP Global PFC Group and developed with financial support of Switzerland, led
by Zhanyun Wang (ETH Zürich, Switzerland) and with technical support from Thomas
Roiss. Input was received from reviews of the fact cards by the Global PFC Group. The
report is published under the responsibility of the Chemicals and Biotechnology
Committee.

The OECD Per- and Polyfluoroalkyl Substances (PFAS) project has been
produced with the financial assistance of the European Union. The views expressed herein
can in no way be taken to reflect the official opinion of the European Union.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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Table of contents
Background, aims and scope ................................................................................................................ 8
1. Perfluoroalkyl phosphonic (a) and phosphinic acids (b) (PFPAs & PFPIAs) ........................... 10
2. Perfluoroalkyl carboxylic (a) and dicarboxylic (b) acids ............................................................. 16
3. Perfluoroalkane sulfonic (a) and sulfinic (b) acids ....................................................................... 31
4. Per- and polyfluoroalkylether carboxylic (a) and sulfonic (b) acids ........................................... 42
5. Perfluoroalkanoyl fluorides (a) and their derivatives (b) ............................................................ 48
6. Perfluoroalkanesulfonyl fluorides (a) and their derivatives (b) ................................................. 52
7. n:2 Fluorotelomer-based compounds ............................................................................................ 58
8. n:1 Fluorotelomer-based compounds ............................................................................................ 66
9. Perfluoroalkylethers (a), epoxides (b), and vinyl ethers (c) (non-polymers) .............................. 68
10. Perfluoroalkenes (a) and derivatives (b) ..................................................................................... 70
11. Specific hydrofluoro-carbons (a), -ethers (b), and -olefins (c) .................................................. 73
12. Side-chain fluorinated aromatics ................................................................................................. 79
13. Fluoropolymers .............................................................................................................................. 83
14. Fluoroelastomers ........................................................................................................................... 87
15. Perfluoropolyethers ....................................................................................................................... 92
Annex A. List of PFASs Included in the Fact Cards, Their Acronyms, CAS Registry Numbers(CASRNs), DTXSIDs and Fact Card Location................................................................................. 95

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Background, aims and scope
The OECD/UNEP Global PFC Group1 was established to respond to the Resolution II/5
adopted at the second session of the UN International Conference on Chemicals
Management (ICCM 2) in 2009, which calls upon intergovernmental organizations,
governments and other stakeholders to “consider the development, facilitation andpromotion in an open, transparent and inclusive manner of national and international
stewardship programmes and regulatory approaches to reduce emissions and the content ofrelevant perfluorinated chemicals of concern in products and to work toward global
elimination, where appropriate and technically feasible”. Further work on this resolution
was reaffirmed in Resolution III/3 adopted at ICCM 3 noting that a significant need remains
for additional work to support implementation of Resolution II/5. This report is preparedwithin the framework of the Group. For more details on the Group and its work, see theOECD PFAS web portal (https://oe.cd/2M9).
This document contains a set of 15 fact cards2 on major groups of per- and polyfluoroalkyl
substances (PFASs), prepared by the OECD/UNEP Global PFC Group between June 2018
and June 2021. The fact cards aim to provide non-expert stakeholders a quick initial glance
into these groups of PFASs with some basic information on: (1) chemical identities3,
synthesis and inherent properties such as bioaccumulation and transformation, (2) historicaland ongoing industrial practices and commercial uses of some major commercial products,(3) regulatory status, (4) examples of reported occurrences in the environment and humans,and (5) major knowledge gaps in terms of previous sections. The fact cards also provide
references where interested readers may find additional information; note that due to thefast-moving nature of the science and knowledge on PFASs, the listed references are by nomeans complete. For information and practical guidance on the use of terminology inregard to PFASs, readers are referred to the OECD PFAS Terminology report4.
It should also be noted that health and environmental effects of PFASs are not included in
the fact cards. For a number of well-studied legacy PFASs, most notably perfluorooctanoic
acid (PFOA) and perfluorooctane sulfonic acid (PFOS), a wealth of knowledge on theirrelated environmental and human health effects have been studied and synthesized,
demonstrating that they may cause a wide range of adverse health effects. These studies
have played a key role in the decision making of existing regulatory actions on them,including restrictions and setting up health guideline values. For many other PFASs,
considerable efforts are being made to study their health and environmental effects; existing
evidence shows that exposure to many novel and emerging PFASs may result in adverse

1

The term “PFC” in “OECD/UNEP Global PFC Group” refers to “per- and polyfluorinated chemicals”, andnot to perfluorocarbons. “Per- and polyfluorinated chemicals” or “PFCs” were widely used before the more
precise term “per- and polyfluoroalkyl substances” was recommended by Buck et al. in 2011. As it is part ofthe official name of the Group, it remains unchanged here.
2
Note that one fact card may contain more than one groups of PFASs that may share some similarities, e.g. interms of structural traits, characteristics or uses; however, this arrangement does not imply any grouping
strategies for PFASs.
3
Note that the Markush structure representations and molecular formulas in each fact card represent only thelinear isomer of the respective substances. In reality, for many PFASs, branched or cyclic isomers have also
been generated, and may be identified in products or the environment.
4
OECD (2021), Reconciling Terminology of the Universe of Per- and Polyfluoroalkyl Substances:
Recommendations and Practical Guidance, OECD Series on Risk Management, No. 61, OECD Publishing,Paris,
https://www.oecd.org/chemicalsafety/portal-perfluorinated-chemicals/terminology-per-andpolyfluoroalkyl-substances.pdf.
FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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ENV/CBC/MONO(2022)1  9health and environmental effects of concern, including similar adverse effects as the PFASs
that they replace (though possibly with different mechanisms of action). Interested readers
are strongly recommended to consult the following sources, references therein, and othersources for information on the health and environmental effects of PFASs:

DeWitt JC (ed.), 2015. Toxicological effects of perfluoroalkyl and polyfluoroalkyl
substances.
SpringerInternational
Publishing,
Switzerland.
https://doi.org/10.1007/978-3-319-15518-0.

National Toxicology Program, 2016. Monograph on immunotoxicity associatedwith exposure to perfluorooctanoic acid (PFOA) and perfluorooctane sulfonate(PFOS)
https://ntp.niehs.nih.gov/ntp/ohat/pfoa_pfos/pfoa_pfosmonograph_508.pdf.

International Agency for Research on Cancer (IARC), 2017. Some chemicals usedas solvents and in polymer manufacture. IARC Monographs on the Evaluation ofCarcinogenic Risks to Human, Volume 110. https://publications.iarc.fr/547.

Pelch KE, Reade A, Wolffe TAM, Kwiatkowski CF. 2019. PFAS health effects
database: Protocol for a systematic evidence map. Environment International 130,104851, https://doi.org/10.1016/j.envint.2019.05.045; https://pfastoxdatabase.org.

Ankley GT, Cureton P, Hoke RA, Houde M, Kumar A, Kurias J, Lanno R,
McCarthy C, Newsted J, Salic CJ, Sample BE, Sepúlveda MS, Steevens J,
Valsecchi S. 2020. Assessing the ecological risks of per- and polyfluoroalkyl
substances: current state-of-the science and a proposed path forward.
Environmental
Toxicology
andChemistry
40(3),
564–605.
https://doi.org/10.1002/etc.4869.

Fenton SE, Ducatman A, Boobis A, DeWitt JC, Lau C, Ng C, Smith JS, Roberts
SM. 2020. Per- and polyfluoroalkyl substance toxicity and human health review:
Current state of knowledge and strategies for informing future research.
Environmental
Toxicology
andChemistry,
40(3),
606–630.
https://doi.org/10.1002/etc.4890.

Interstate Technology Regulatory Council (ITRC), 2020. PFAS Fact Sheets – 7.
Human and Ecological Health Effects of select PFAS. https://pfas-1.itrcweb.org/7human-and-ecological-health-effects-of-select-pfas/.

Lohmann R, Cousins IT, DeWitt JC, Glüge J, Goldenman G, Herzke D, Lindstrom
AB, Miller MF, Ng CA, Patton S, Scheringer M, Trier X, Wang Z. 2020. Are
fluoropolymers really of low concern for human and environmental health andseparate from other PFAS? Environmental Science & Technology 54(20), 12820–
12828. https://doi.org/10.1021/acs.est.0c03244.



Hodnebrog Ø, Aamaas B, Fuglestvedt JS, Marston G, Myhre G, Nielsen CJ,
Sandstad M, Shine KP, Wallington TJ. 2020. Updated global warming potentials
and radiative efficiencies of halocarbons and other weak atmospheric absorbers.
ReviewsofGeophysics
58,
e2019RG000691.
https://doi.org/10.1029/2019RG000691.



Agency for Toxic Substances and Disease Registry (ATSDR). 2021. Toxicological
profile for Perfluoroalkyls. United States Department of Health and Human
Services,
PublicHealthService.
https://wwwn.cdc.gov/TSP/ToxProfiles/ToxProfiles.aspx?id=1117&tid=237; p C8
SciencePanel.
C8
Study
Publications.
http://www.c8sciencepanel.org/publications.html.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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1. Perfluoroalkyl phosphonic (a) and phosphinic acids (b) (PFPAs & PFPIAs)
Key publication: Wang, Z., Cousins, I. T., Berger, U., Hungerbühler, K. & Scheringer, M.
Comparative assessment of the environmental hazards of and exposure to perfluoroalkyl
phosphonic and phosphinic acids (PFPAs and PFPIAs): Current knowledge, gaps,
challenges and research needs. Environ. Int. 89–90, 235–247 (2016).

Chemical Information & Properties
Identification and Terminology
Name

Perfluoroalkyl phosphonic acids

Perfluoroalkyl phosphinic acids

Other Names

Phosphonic acid, perfluoro-alkyl
derivatives[1];perfluoroalkyl phosphonic acids [1];mono-substituted perfluorinated phosphonicacids [2]Phosphinic acid, bis(perfluoro-alkyl)
derivatives [1];bis(perfluoroalkyl) phosphinic acids [1];di-substituted perfluorinated phosphonic acids[2]

Acronym

PFPAs

PFPIAsChemical
FormulaCnF2n+1P(=O)(OH)2
e.g. 4 ≤ n ≤ 12

CnF2n+1P(=O)(OH)(CmF2m+1)
e.g. 4 ≤ n, m ≤ 12

DTXSID801024679

DTXSID101024680

e.g. perfluorooctyl phosphonic acid(C8 PFPA)

e.g. bis(perfluorooctyl) phosphinic acid
(C8/C8 PFPIA)

General
Structure (onlylinear isomers
shown here)
US EPA
CompToxMarkush ID
CommonTerminology

Degradability, Mobility, Bioconcentration
Abiotic
degradation

No degradation when exposed to heat,
oxidants, and bases [3]Hydrolyzes to yield PFPAs and CnF2n+1H (aPFCA precursor) when exposed to heat orbases [3]Biodegradation

No aerobic biodegradation in surface water[3]

Biotransforms to yield PFPAs in rainbow
trout [3]Adsorption onorganic matter(log Kd, cm3/g)

C6 PFPA: −0.15 (soil)
C8 PFPA: 0.89 (soil), 1.07 (sludge)
C10 PFPA: 1.1 (soil),
1.17–1.63 (sludge) [3]

C6/C6 PFPIA: 1.70 (soil)
C6/C8 PFPIA: 2.09 (soil)
C8/C8 PFPIA: 1.96 (soil) [3]Sorption insoils

C6 PFPA: 90% remaining in aqueous phase
after 24 h;
C8 PFPA: 60% remaining in aqueous phase
after 24 h;
C10 PFPA: 15% remaining in aqueous phase
after 24 h; [4]C6/C6 PFPIA: 10% remaining in aqueous
phase after 24 h;
C6/C8 PFPIA, C8/C8-PFPIA: <LOD remaining
in aqueous phase after 24 h; [4]FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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ENV/CBC/MONO(2022)1  11

Bioaccumulati
on potential

Binds to proteins and blood cells [3]Elimination in rainbow trout [5]:t1/2 (C6 PFPA) = 0.13 d
t1/2 (C8 PFPA) = 4.4 d
t1/2 (C10 PFPA) = 5.3 d
Elimination in rats [2]:t1/2 (C6 PFPA) = ≤0.96 d (♂), ≤1.6 (♀)
t1/2 (C8 PFPA) = ≤1.6 d (♂), ≤2.1 (♀)
t1/2 (C10 PFPA) = ≤2.5 d (♂), ≤2.8 (♀)

Binds to proteins [3]Elimination in rainbow trout [5]:t1/2 (C6/C6 PFPIA) = 5.5 dt1/2 (C6/C8 PFPIA) = 20.4 d
t1/2 (C8/C8 PFPIA) = 52.7 d
Elimination in rats [2]:t1/2 (C6/C6 PFPIA) = ≤1.8 d (♂), ≤2.3 (♀)
t1/2 (C6/C8 PFPIA) = ≤2.0 d (♂), ≤2.7 (♀)
t1/2 (C8/C8 PFPIA) = ≤2.7 d (♂), ≤4.0 (♀)
t1/2 (C6/C10 PFPIA) = ≤2.0 d (♂), ≤3.0 (♀)
t1/2 (C8/C10 PFPIA) = ≤5.1 d (♂), ≤9.3 (♀)
t1/2 (C6/C12 PFPIA) = ≤5.4 d (♂), ≤8.4 (♀)

BCFsteady state(zebrafish,
whole body)

15.8–200 L/kg [6](for C6, C8, and C10 PFPAs; fish were
exposed to mixture of PFAS at two different
exposure levels)

3.9×104–1.58×109 L/kg [6](for C6/C6, C6/C8, C8/C8, C6/C10, C8/C10, andC6/C12 PFPIAs; fish were exposed to mixtureof PFAS at two different exposure levels)

Synthesis
Main Synthesis
Method [3]Starting material: perfluoroalkyl iodides (PFAIs, often as a mixture of linear homologs)ℎ𝑒𝑎𝑡

6 𝐶𝑛 𝐹2𝑛+1 𝐼 + 𝑃4 →2 𝐶𝑛 𝐹2𝑛+1 𝑃𝐼2 + 2 (𝐶𝑛 𝐹2𝑛+1 )2 𝑃𝐼

Then, either
𝑜𝑥𝑖𝑑𝑎𝑛𝑡

𝐶𝑛 𝐹2𝑛+1 𝑃𝐼2 𝑜𝑟 (𝐶𝑛 𝐹2𝑛+1 )2 𝑃𝐼 + 𝐻2 𝑂 →or𝐶𝑛 𝐹2𝑛+1 𝑃𝐼2 𝑜𝑟 (𝐶𝑛 𝐹2𝑛+1 )2 𝑃𝐼 + 𝐴𝑔𝐶𝑙 →𝐶𝑛 𝐹2𝑛+1 𝑃𝑂(𝑂𝐻)2 𝑜𝑟 (𝐶𝑛 𝐹2𝑛+1 )2 𝑃𝑂(𝑂𝐻)

𝑜𝑥𝑖𝑑𝑎𝑛𝑡𝑜𝑥𝑖𝑑𝑎𝑛𝑡

𝐶𝑛 𝐹2𝑛+1 𝑃𝐶𝑙2 𝑜𝑟 (𝐶𝑛 𝐹2𝑛+1 )2 𝑃𝐶𝑙 + 𝐻2 𝑂 →𝐶𝑛 𝐹2𝑛+1 𝑃𝐶𝑙2 𝑜𝑟 (𝐶𝑛 𝐹2𝑛+1 )2 𝑃𝐶𝑙

𝐶𝑛 𝐹2𝑛+1 𝑃𝑂(𝑂𝐻)2 𝑜𝑟 (𝐶𝑛 𝐹2𝑛+1 )2𝑃𝑂(𝑂𝐻)

Alternatively, tri(perfluoroalkyl)difluorophosphoranes can be used as a starting material. Thisroute then yields PFPIAs with side chains of the same length, preferably n = 2 or n = 4. [7]Possible
Impurities

PFCAs and/or other byproducts can be formed during PFAI manufacture. [3]Industrial Practices & Commercial Uses
Major Commercial Products
Name

Masurf-780 [2]Composition

80% aqueous solution of mixtures of PFPAs and PFPIAs. [3]Measured composition:
10% C6 PFPA, 8% C8 PFPA, 5% C10 PFPA
37% C6/C6 PFPIA, 33% C6/C8 PFPIA, 27% C8/C8 PFPIA(amounting to 120%, likely due to empirical deviations)Name

Tivida FL 2100 [3]CAS Number

52299-25-9

Composition

C4/C4-PFPIA [3], [8]FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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Production or
import volumes

EU: 0–10 t/yr [3], [8]Name

Phosphonic acid, perfluoro-C6–12-alkyl derivatives (C6–C12 PFPAs) [3]

CAS Number

68412-68-0

Production or
import volumes

US: <1,000,000 lbs (500t) in 2015 [23]Denmark, Norway, Sweden: >4.33 t/yr in 1999–2011 (some amounts have been claimed asconfidential business information) [3]Name

Phosphinic acid, bis(perfluoro-C6–12-alkyl) derivatives (C6–C12 PFPIAs)

CAS Number

68412-69-1

Production or
import volumes

US: <500t in 2015 [23]Denmark, Norway, Sweden: >3.33 t/yr in 1999–2011 (some amounts have been claimed asconfidential business information) [3]

Uses
Major
applications

Surfactants, levelling and wetting agents in waxes and coatings, and defoaming agents in the
textile industry, pharmaceutical industry, metal industry, and in pesticide formulations [2], [9]Regulatory Status
Some of these substances are regulated under 40 CFR §721.10536 Long-chain perfluoroalkyl
UScarboxylate chemical substances [10].
A final rule to revoke the tolerance exemptions for mono- and bis-(1H,1H,2H,2Hperfluoroalkyl) phosphates (PAPs) where the alkyl group is even numbered and in the C6-C12
range was published in August 2006 with an effective date 18 months after the publication of
the final rule. They were used as surfactants (inert ingredients) in pesticide formulations in thepast, but are no longer included in U.S. EPA’s list of approved inert ingredients for pesticide
products. [11], [12]CanadaAs CAS Numbers 68412-68-0 and 68412-69-1 are also precursors to long-chain (C9–C20)
PFCAs, they were assessed together in 2012 and are managed pursuant to the Prohibition of
Certain Toxic Substances Regulations, 2012 [19], [20].

International efforts
The proposal to list long-chain perfluorocarboxylic acids (PFCAs), their salts and related compounds in Annexes
A, B and/or C to the Stockholm Convention on Persistent Organic Pollutants is under review by the Persistent
Organic Pollutants Review Committee [22].

Examples of reported occurrences
Type oflocations/samples(Environmental)
media

Detected in
one ormultipleregions

ExamplesLocation,year

Levels [min.–max. (detection
frequency)]

Note: Non-detects are reported as below the value of the limit of detection (“<LOD”).
ng = nanograms, NR = not reported, ww = wet weight
airone
Close toChina,C6 PFPA: <0.04–30.2 ng/L (2/32)
surfacefluorochemical
multiple 2012
water
manufacturing
soil
park
sediment
airone
Close toNorth
C6 PFPA: <0.025–1.2 ng/L (12/30)

Ref.

[13]

[14]

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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agricultural
inputssurfacewater
soil
sediment

multiple

America,2005 &
2007

C8 PFPA: <0.025–3.4 ng/L (24/30)
C10 PFPA: <0.025–0.87 ng/L (22/30)

Not close to
specific point
sourcesair
surfacewater
soil
sedimentone
multiple

Europe,2009

C8 PFPA: 1.0 ng/L (1/10)[15]Asia, 2009

C6 PFPA: <0.3–9.95 ng/L (14/76)[16]

effluent
sludgeone
multiple

North
America,2004 &
2007

C6 PFPA: <0.083–6.5 ng/L (4/7)
C8 PFPA: <0.083–2.5 ng/L (6/7)
C10 PFPA: <0.083–0.46 ng/L (3/7)[14]Indoorenvironment

Indoor dustone
multiple

North
America,
2007–2008

C6 PFPA: <0.25–846 ng/g (57/102)
C8 PFPA: <0.38–290 ng/g (28/102)
C10 PFPA: <2.1–152 ng/g (6/102)
C6/C6 PFPIA: <0.088–525 ng/g
(62/102)
C6/C8 PFPIA: <0.086–944 ng/g
(78/102)
C8/C8 PFPIA: <0.17–525 ng/g
(42/102)[18]

Wildlife

Lake troutone
multiple

North
America,
2008–2010

C6/C6 PFPIA: <0.001–0.018 ng/g (NR)C6/C8 PFPIA: <0.002–0.032 ng/g (NR)

[9]

North
America,
2010–2012

C6/C6 PFPIA: 0.2–1.6 ng/g ww(grouped means, 66/66)
C6/C8 PFPIA: 0.25–3.0 ng/g ww(grouped means, 66/66)
C8/C8 PFPIA: <0.025–0.29 ng/g ww(grouped means, 55/66)
C6/C10 PFPIA: <LOD–0.15 ng/g ww(grouped means, 55/66)
C8/C10 PFPIA: <LOD ng/g ww (0/66)
C6/C12 PFPIA: <LOD ng/g ww (0/66)

[21]

North
America,2009

C6/C6 PFPIA: <1–50.24 ng/g (17/70)
C6/C8 PFPIA: <1–60.96 ng/g (28/40)
C8/C8 PFPIA: <1–22.19 ng/g (1/40)

[17]

WWTP

Doublecrested
cormorants

Humangeneralpopulation
occupational
exposureone
multiple

Knowledge gaps

- Information on commercial products, especially current production and use (including volumes).

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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References
[1]

[2]
[3]

[4]
[5]

[6]

[7]
[8]

[9]

[10]

[11]

[12]
[13]

[14]

[15]

[16]

[17]

National Industrial Chemicals Notification and Assessment Scheme (NICNAS), “Perfluoroalkyl
phosphonic and phosphinic acids: Environment tier II assessment,” Department of Health - AustralianGovernment, 2018. [Online]. Available: https://www.nicnas.gov.au/chemical-information/imapassessments/imap-assessments/tier-ii-environment-assessments/pfpas_PFPIAs. [Accessed: 19-Jul-2019].
J. C. D’eon and S. A. Mabury, “Uptake and elimination of perfluorinated phosphonic acids in the rat,”
Environ. Toxicol. Chem., vol. 29, no. 6, pp. 1319–1329, Mar. 2010.
Z. Wang, I. T. Cousins, U. Berger, K. Hungerbühler, and M. Scheringer, “Comparative assessment of theenvironmental hazards of and exposure to perfluoroalkyl phosphonic and phosphinic acids (PFPAs and
PFPIAs): Current knowledge, gaps, challenges and research needs,” Environ. Int., vol. 89–90, pp. 235–
247, Apr. 2016.
H. Lee and S. A. Mabury, “Sorption of Perfluoroalkyl Phosphonates and Perfluoroalkyl Phosphinates inSoils,” Environ. Sci. Technol., vol. 51, no. 6, pp. 3197–3205, Mar. 2017.
H. Lee, A.O. de Silva, and S.A. Mabury, “Dietary bioaccumulation of perfluorophosphonates andperfluorophosphinates in juvenile rainbow trout: evidence of metabolism of perfluorophosphinates,”
Environ. Sci. Technol., vol. 46, pp. 3489–3497, 2012.
F. Chen, Z. Gong, and B. C. Kelly, “Bioavailability and bioconcentration potential of perfluoroalkylphosphinic and -phosphonic acids in zebrafish ( Danio rerio ): Comparison to perfluorocarboxylates andperfluorosulfonates,” Sci. Total Environ., vol. 568, no. 1, pp. 33–41, Oct. 2016.
U. Welz-Biermann et al., “Process for the Preparation of Bis(perfluoroalkyl)phosphinic acids and salts
thereof,” US 7,202,379 B2, 2007.
European Chemicals Agency (ECHA), “bis(nonafluorobutyl)phosphinic acid - Registration Dossier”[Online].
Available:
https://echa.europa.eu/registration-dossier/-/registered-dossier/8036/3/1/4.
[Accessed: 26-Mar-2020].
R. Guo et al., “Determination of polyfluoroalkyl phosphoric acid diesters, perfluoroalkyl phosphonicacids, perfluoroalkyl phosphinic acids, perfluoroalkyl carboxylic acids, and perfluoroalkane sulfonicacids in lake trout from the Great Lakes region,” Anal. Bioanal. Chem., vol. 404, no. 9, pp. 2699–2709,
Nov. 2012.
USA, “40 CFR §721.10536 Long-chain perfluoroalkyl carboxylate chemical substances,” Available at:https://www.ecfr.gov/cgi-bin/textidx?SID=c8175aed22d0b9446beca21293ba915f&mc=true&node=se40.33.721_110536&rgn=div8.
U.S. Environmental Protection Agency, “Inert ingredient; Revocation of the tolerance exemption for
mono- and bis-(1H, 1H, 2H, 2H-perfluoroalkyl) phosphates where the alkyl group is even numbered andin the C6-C12 range,” Fed. Reg., vol. 71, no. 153, pp. 45408–45411, Aug. 2006.
U.S. EPA, “Inert Ingredients Regulation,” Available at: https://www.epa.gov/pesticide-registration/inertingredients-regulation.
H. Jin, Y. Zhang, L. Zhu, and J. W. Martin, “Isomer Profiles of Perfluoroalkyl Substances in Water andSoil Surrounding a Chinese Fluorochemical Manufacturing Park,” Environ. Sci. Technol., vol. 49, no. 8,
pp. 4946–4954, Apr. 2015.
J. C. D’eon, P. W. Crozier, V. I. Furdui, E. J. Reiner, E. L. Libelo, and S. A. Mabury, “Perfluorinatedphosphonic acids in Canadian surface waters anhd wastewater treatment plant effluent: Discovery of a
new class of perfluorinated acids” Environ. Toxicol. Chem., vol. 28, no. 10, p. 2101, 2009.
X. Esparza, E. Moyano, J. de Boer, M. T. Galceran, and S. P. J. van Leeuwen, “Analysis of perfluorinatedphosponic acids and perfluorooctane sulfonic acid in water, sludge and sediment by LC–MS/MS,”
Talanta, vol. 86, no. 1, pp. 329–336, Oct. 2011.
Y. Zushi, F. Ye, M. Motegi, K. Nojiri, S. Hosono, T. Suzuki, Y. Kosugi, K. Yaguchi, and S. Masunaga,“Spatially Detailed Survey on Pollution by Multiple Perfluorinated Compounds in the Tokyo Bay Basin
of Japan” Environ. Sci. Technol., vol. 45, no. 7, pp. 2887–2893, 2011.
H. Lee and S. A. Mabury, “A Pilot Survey of Legacy and Current Commercial Fluorinated Chemicals in

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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ENV/CBC/MONO(2022)1  15

[18]

[19]

[20]
[21]

[22]

[23]

Human Sera from United States Donors in 2009,” Environ. Sci. Technol., vol. 45, no. 19, pp. 8067–8074,
Oct. 2011.
A. O. De Silva, C. N. Allard, C. Spencer, G. M. Webster, and M. Shoeib, “Phosphorus-containing
fluorinated organics: Polyfluoroalkyl phosphoric acid diesters (diPAPs), perfluorophosphonates (PFPAs),and perfluorophosphinates (PFPIAs) in residential indoor dust,” Environ. Sci. Technol., vol. 46, no. 22,
pp. 12575–12582, 2012.
Environment Canada, “Screening assessment: Long-Chain (C9–C20) Perfluorocarboxylic Acids, their
Salts and their Precursors,” Gatineau (QC): Environment Canada, Existing Substances Division, 2012.
Available at: http://ec.gc.ca/ese-ees/default.asp?lang=En&n=CA29B043-1.
Canada, “Prohibition of Certain Toxic Substances Regulations, SOR/2012-285,” 2016. Available at:https://laws-lois.justice.gc.ca/eng/regulations/SOR-2012-285/index.html.
A. O. De Silva et al., “Perfluoroalkylphosphinic Acids in Northern Pike (Esox lucius), Double-Crested
Cormorants (Phalacrocorax auritus), and Bottlenose Dolphins (Tursiops truncatus) in Relation to Other
Perfluoroalkyl Acids,” Environ. Sci. Technol., vol. 50, no. 20, pp. 10903-10913, 2016.
Stockholm Convention on Persistant Organic Pollutants, “Proposal to list long-chain perfluorocarboxylic
acids, their salts and related compounds in Annexes A, B and/or C to the Stockholm Convention on
Persistent Organic Pollutants” 2021. UNEP/POPS/POPRC.17/7.
U.S. EPA, Chemical Data Reporting (CDR), 2016. Available at https://www.epa.gov/chemical-datareporting/access-cdr-data.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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2. Perfluoroalkyl carboxylic (a) and dicarboxylic (b) acids
Key publication: Prevedouros, Konstantinos, Ian T. Cousins, Robert C. Buck, and Stephen
H. Korzeniowski. 2006. “Sources, Fate and Transport of Perfluorocarboxylates.”
Environmental Science & Technology 40 (1): 32–44. https://doi.org/10.1021/es0512475.

Chemical Information & Properties
Identification and Terminology
Name

Perfluoroalkyl carboxylic acids5

Perfluoroalkyl dicarboxylic acids

Other Names

Perfluorcarboxylic acids; perfluorinatedcarboxylic acids; perfluoroalkanoic acids [1]Fluorinated dicarboxylic acids;
perfluoroalkanedicarboxylic acids [2]Acronym

PFCAs

PFdiCAs

Chemical FormulaC(n−1)F2n−1COOH

C(n−2)F2n−4(COOH)2DTXSID00893893

DTXSID80893896

General Structure(linear isomers)

US EPA CompTox
Markush ID
Individualacronyms andcarbon chain
length (asrecommended by
Buck et al. 2011)

Short-chain PFCAs (n ≤ 7) TFA: n=2; PFPrA: n=3; PFBA: n=4;
PFPeA: n=5; PFHxA: n=6; PFHpA: n=7;Long-chain PFCAs (n ≥ 8) PFOA: n=8; PFNA: n=9; PFDA: n=10; PFUnDA: n=11:
PFDoDA: n=12; PFTrDA: n=13; PFTeDA: n=14

Degradability, Mobility, Bioconcentration
Note: The following information refers only to PFCAs, due to a lack of information on PFdiCAs.
Abiotic
degradation

PFCAs generally do not undergo degradation in the environment [3].

Atmosphericdegradation

An estimated atmospheric lifetime regarding degradation (via reaction with OH
radicals, forming COF2) of PFCAs (n >1) is 130 days. Dry and wet deposition is more
relevant, with time scales in the order of 10 days. [4]Biodegradation

No degradation of PFCAs under aerobic or anaerobic conditions over 15 weeks inclosed bottle tests with municipal sewage sludge [5] 6

Bioaccumulation
potential

Long-chain PFCAs (n ≥8) are known to be bioaccumulative [9], [10]. Due to theirproteinophilic nature and slow elimination rates in air-breathing animals they are5

For more examples of compounds in the group of PFCAs and their associated information, one may searchfor “DTXSID40893892”, “DTXSID00893893”, “DTXSID60893894” at the U.S. EPA CompTox Chemicals
Dashboard: https://comptox.epa.gov/dashboard.
6
One study found PFOA was no longer detected after 26 d under anaerobic conditions in WWTP sludge [6].
However, since no increase in fluoride concentration was observed, it is doubtful that this result is due toanaerobic degradation, and more likely to be due to sorption phenomena [7]. In another study, PFOA was foundto be partially degraded (removal of up to 60% over 100 day inoculations) by a specific bacterial strain(Acidimicrobium sp. Strain A6) under laboratory conditions where they were used as the sole source of carbon;
the applicability of this method in the field environment is currently unclear. [8]FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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especially bioaccumulative in higher trophic level wildlife and humans [11]. Someshort-chain PFCAs (such as PFBA and PFHxA) are also biomagnifying with BMF
values >1 [11].
TMF (trophic
magnification
factor)In the overall Arctic marine food web [12]: PFHpA: 0.76; PFOA: 1.93; PFNA: 4.23;
PFDA: 4.81; PFUnDA: 4.79; PFDoDA: 2.96; PFTeDA: 1.97
In French riverine systems [13]: PFOA: 0.39–0.58; PFNA: 0.61–9.9; PFDA: 2.6–10.9;
PFUnDA: 2.4–4.2; PFDoDA: 1.4–2.7; PFTrDA: 0.9–14.9; PFTeDA: 0.7–2.8

BCF (carp,
liver/blood,[L/kg])7[14]

PFOA 134 / 611; PFNA: 150 / 4686; PFDA: 5957 / 34,896; PFUnDA: 1877 / 17,328;
PFDoDA: 1945 / 11,988

Plant uptake

PFCAs have been found to accumulate in plants, with BCF values generally decreasing
as chain lengths increase [61]–[64]. In various crops (lettuce, tomato, cabbage, zucchini),highest concentrations of long-chain PFCAs (>C11) have been found in roots, while shortchain PFCAs have been found to accumulate in leaves. [61], [62]In trees (birch, spruce), the highest BCF values (chain-length-unspecified) have beenfound in foliage. [64]Environmental
transport

Main emissions sources of PFCAs lie in fluoropolymer manufacture and degradation offluorotelomer compounds, among others [9]. Apart from manufacturing sites, relevant
point sources also include airports, military bases, and other installations where AFFFs
are or were used, as well as landfills. [15], [16]The majority of PFCAs in the environment are contained within the oceans, wheresediment and the transport to deep oceans are sinks. Similarly, oceanic transport isbelieved to be most important transport pathway for PFCAs to the Arctic ocean. [3]Adsorption onorganic matter 8(log Koc, [logL/kg])

Log Koc = 2.1 (for PFOA, average derived from multiple studies) [17]Partitioncoefficients (Kd)between sedimentand water

Increasing with chain length:0.04 (PFOA)–0.72 (PFDoDA) [14](measured in Korea, n=17)

Synthesis
Main Synthesis
MethodMainly electrochemical fluorination of alkanoyl fluorides is employed to produce
PFCAs (although in a mixture of linear and branched isomers):
𝐶𝑛 𝐻2𝑛+1 𝐶𝑂𝐹 + (2𝑛 + 1)𝐻𝐹 →𝐶𝑛 𝐹2𝑛+1 𝐶𝑂𝐹 + (2𝑛 + 1)𝐻2
Hydrolysis then yields the respective carboxylic acid. Yields decrease with increasing
chain length, and when acid chlorides instead of acid fluorides are used. [1], [2], [18],[19]
Alternatively, telomerization-based processes, followed by dehydroiodination andoxidation or direct carboxylation of the fluorotelomer iodide, to synthesize linear

7 Note that due to the acidic nature and the proteinophilic properties of PFCAs, BCFs are not necessarily

accurate indicators of their overall biomagnification behavior in aquatic organisms. [11]8 It should be noted that “the behaviour of PFASs in the environment is more complex than can be explainedby a single soil or sediment property and it is not appropriate to express the sorption behaviour of thesechemicals normalized over the OC content of the sorbent (Koc). An assessment of the published data has shownthat neither OC, pH nor clay content alone could explain the sorption behaviour of the PFASs.” [18]
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PFCAs with one or two (respectively) more carbon atoms than the starting material (seealso the fact cards #7 on n:2 fluorotelomers). [1], [2], [18], [56]
𝐹(𝐶𝐹2 )𝑛 𝐼 + 𝐶𝐻2 𝐶𝐻2 →− 𝐻𝐼

𝐹(𝐶𝐹2 )𝑛 𝐶𝐻2 𝐶𝐻2 𝐼 →𝐹(𝐶𝐹2 )𝑛 𝐼 + 𝐶𝑂2 + 𝑍𝑛-𝐶𝑢 →+𝐶𝑟2 𝑂72−
𝑜𝑟 𝑂3

𝐹(𝐶𝐹2 )𝑛 𝐶𝐻𝐶𝐻2 →(𝑎𝑞.) 𝐻𝐶𝑙

(𝐶𝐹2 )𝑛 𝐶𝑂𝑂𝐻

(𝐶𝐹2 )𝑛 𝐶𝑂𝑂𝐻

On a laboratory scale, there are several other synthesis methods available, see [19, p.
1488].
PFOA is synthesized by direct oxidation of the corresponding iodide (C8F17I) using SO3(or H2SO4)9, yielding C7F15CO2X [20].
PFdiCAs are generally synthesized via the electrochemical fluorination method, followedby hydrolysis, acidification, and extraction (similarly to for PFCAs above) [2], or are
obtained from diiodoperfluoroalkanes [67]Possible Impurities

Electrochemical fluorination is not very selective and yields – besides the target
compound – a number of linear, branched, or cyclic homologues. In the telomerization
process, the purity of the product depends on the purity of the starting material.

Industrial Practices & Commercial Uses
Major Commercial ProductsNameAmmonium perfluorooctanoate (APFO)

Chemical Formula

NH4+ C7F15COO−

CAS Number

3825-26-1

Use

As a processing aid in the dispersion process for production of fluoropolymers [1];surfactant [1]Production/Import
volumes10

Global (1999): approx. 260 t/yr [3]US (2015): <500t in 2015 [21]Global (1951–2004): 3600–5700 t (estimated) [3]Name

Ammonium perfluorononanoate (APFN)

Chemical Formula

NH4+ C8F17COO−

CAS Number

4149-60-4

Use

Processing aid in polyvinylidene fluoride (PVDF) production. [3]Production/Import
volumesGlobal (1951–2004): 800–2300 t (estimated) [3]Global (2004): 15–75 t/yr [3]NameSurflon® S-111 [1], [3]Composition

74% APFN (NH4+ C8F17COO−), 20% APFUnD (NH4+ C10F21COO−),
5% APFTrD (NH4+ C12F25COO−), 1% other linear PFCAs (with n=7,9,11) [1]

CAS Number

72968-38-8

9According to information provided by representatives of the manufacturing industry.
Long-chain PFCAs have largely been phased out and replaced in the past years; however, no information on
more recent production volumes is available.
10

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Use

Processing aid in polyvinylidene fluoride (PVDF) production. [3]Uses
Major applications

PFCAs have been used as polymerization aids in the production of fluoropolymers, assurfactants, in insecticide formulations, and in various consumer products. Historically,
PFCAs were also ingredients of early generations of fire-fighting foams [9], [23], [24].
The use of silver salts of PFdiCAs in coordination polymers has been investigated [25],[26] and perfluoroadipic acid (HOOC–C4F8–COOH; CAS Number 336-08-3) is
mentioned in a small number of patents (e.g. for thermoplastic elastomers or lowrefractive-index layers in electrooptical devices) [27], [28]. PFdiCAs are also used to
produce the corresponding alcohols via reduction [2].
Perfluorosuccinic acid (377-38-8), perfluoroglutaric acid (376-73-8), and perfluoroadipic
acid (336-08-3) are listed as commercially active in the US TSCA Inventory, while theiruses are unknown.

Regulatory Status
General remarks

Most risk assessment activities focus mainly on PFOA, the most prominent PFCA [18].
Furthermore, regulations generally focus more on longer-chain PFCAs (n ≥8), and lesson short-chain PFCAs, which are believed to be less bioaccumulative (although this belief
is being challenged [10]) and are often used as replacement chemicals [10], [18], [29].
Many limit values for different environmental media have been set at regional, country
and sub-country levels, and a comprehensive overview is available online by the US
Interstate Technology Regulatory Council (ITRC) at https://pfas-1.itrcweb.org/factsheets/ (see “PFAS Water and Soil Values Table”). [30]US

Under the 2010/2015 PFOA Stewardship Program by the U.S. EPA, eight major multinational fluoropolymer and fluorotelomer manufacturers started to phase out long-chain
PFCAs in 2006, which was achieved by 2015. [32] In July 2020, U.S. EPA issued a final
rule requiring notice and U.S. EPA review before manufacturing/processing of certain
long-chain PFAS that have been phased out in the United States could commence. [32]In March 2020, U.S. EPA made a preliminary determination to regulate PFOA in drinking
water. U.S. EPA finalized regulatory determinations in February 2021. In addition,certain PFCAs are regulated at the state level in the United States. [33]EuropePFOA and its ammonium salt (APFO), as well as C9–C14 PFCAs have been identified as
substances of very high concern (SVHCs) under REACH in 2013 [34]. PFOA, APFO andrelated substances have been also added to the restricted substances list (REACH Annex
XVII) in 2017. Restrictions of PFHxA, C9–C14 PFCAs and related substances have also
been proposed [35], [36]. In summer 2020, PFOA and related compounds moved to the
EU POP regulation [37].
EFSA set a TWI (tolerable week intake) value for PFOA of 6 ng/kg bw (nanogram per
kilogram bodyweight) in 2018 [18] and in 2020 set a TWI value for the sum of PFOA,PFNA, PFHxS and PFOS of 4.4 ng/kg bw [38].
PFOA, its salts and precursors as well as long-chain perfluorocarboxylic acids (LCPFCAs), their salts and precursors were assessed in 2012. [39], [40]These substances are prohibited with a limited number of exemptions under theProhibition of Certain Toxic Substances Regulations, 2012 [41].

CanadaInternational Efforts
PFOA, its salts, and PFOA-related compounds are listed as POPs (persistent organic pollutants) under the

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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Annex A (Elimination) to the Stockholm Convention, with several specific exemptions [31]. See the listing forthe definition of PFOA-related compounds covered.
In 2021, long-chain PFCAs (C9–C21), their salts and related compounds were proposed for listing under the
Stockholm Convention (see UNEP/POPS/POPRC.17/7 at https://www.pops.int/poprc17).

Examples of reported occurrences
Type oflocations/samples(Environmental) media

Detected in
one ormultipleregions

ExamplesLocation,year

Levels [min. –max. (detection
frequency)]

Note: Non-detects are reported as below the value of the limit of detection (“<LOD”).
ng = nanograms, dw= dry weight, ww = wet weight, ND = not detected, NR = not reported
airone
PFBA: 4.6–12.0 ng/L (13/13)
Close toEurope,surfacewaterfluorochemical
multiple 2016
PFPeA: <4–8.2 ng/L (10/13)
soil
manufacturing
PFHxA: 4–6.4 ng/L (13/13)
park or othersediment
point sources
PFHpA: 1.5–2.2 ng/L (13/13)

Ref.

[42]

PFOA: 3.5–12 ng/L (13/13)
PFNA: 0.49–1.0 ng/L (13/13)
PFDA: 0.23–0.8 ng/L (13/13)
airsurface watersoil
sedimentone
multiple

North
America,2009

PFHpA: 0.88–6.6 ng/g dw (19/19)[43]

PFOA: 47–470 ng/g dw (19/19)
PFNA: 1.6–6.3 ng/g dw (19/19)
PFDA: 2.1–5.3 ng/g dw (19/19)
PFUnDA: 2.6–14 ng/g dw (19/19)
PFDoDA: 2.2–11 ng/g dw (19/19)

Earth worm

one
multiple

North
America,2009

PFHpA: ND–3.6 ng/g dw (14/19)[43]

PFOA: 51–860 ng/g dw (19/19)
PFNA: 2.0–52 ng/g dw (19/19)
PFDA: 5.9–74 ng/g dw (19/19)
PFUnDA: 19–380 ng/g dw(19/19)PFDoDA: 22–660 ng/g dw(19/19)Surface water,
groundwater,
waste leachate
Not close to
specific point
sourcesair
surface watersoil
sedimentone
multiple

Sweden,2017–
2018

TFA: <34–14000 ng/L (21/34)
PFPrA: <3.1–53000 ng/L (27/34)

[60]

one
multipleAsia,
2010 &
2012

PFHxA: ND–7.94 ng/L (15/19)[14]

PFHpA: ND–3.43 ng/L (16/19)
PFOA: ND–8.34 ng/L (17/19)
PFNA: ND–4.49 ng/L (16/19)
PFDA: ND–4.80 ng/L (12/19)
PFUnDA: ND–1.13 ng/L (15/19)

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PFDoDA: ND–0.33 ng/L (12/19)
11

Drinking waterone
multiple

Europe,2016

PFBA <2–13 ng/L (1/6)[42]

PFPeA: <4–5.7 ng/L (2/6)
PFHxA: <0.1–5.3 ng/L (5/6)
PFHpA: <0.05–2.4 ng/L (3/6)
PFOA: <0.3–2.7 ng/L (4/6)
PFNA: <0.03–0.28 ng/L (3/6)
PFDA: <0.03–0.1 ng/L (2/6)

Canada,2012–
2019

PFBA <1–10 ng/L (151/226)[55]

PFPeA: <1–15 ng/L (115/226)
PFHxA: <1–13 ng/L (122/226)
PFHpA: <1–3.6 ng/L (27/226)
PFOA: <0.5–7.6 ng/L (165/226)
PFNA: <0.5–1.2 ng/L (41/226)
PFDA: <0.5–0.63 ng/L (5/226)
PFUnDA: <1 ng/L (0/226)

DWTP influent

DWTP effluent

North
America,
2013–
2015

PFDoDA: <1 ng/L (0/226)
PFBA: <0.24–96.8 ng/L (23/25)
PFPeA: <0.051–501 ng/L (23/25)
PFHxA: <0.044–55.1 ng/L
(24/25)PFHpA: <0.04–184 ng/L (24/25)
PFOA: <0.56–112 ng/L (19/25)
PFNA: <0.094–41.4 ng/L (24/25)
PFDA: <0.084–31.1 ng/L (15/25)
PFUnDA: <0.067–2.9 ng/L (8/25)
PFDoDA: <0.062–0.28 ng/L
(2/25)PFTrDA: <0.072 ng/L (0/25)
PFTeDA: <0.13 ng/L (0/25)
PFHxDA: <0.4 ng/L (0/25)
PFOcDA: <0.29 ng/L (0/25)
PFBA: <0.24–104 ng/L (22/25)
PFPeA: <0.051–514 ng/L (24/25)
PFHxA: NR–60.8 ng/L (25/25)
PFHpA: <0.04–177 ng/L (23/25)

[44]

[44]

11

U.S. EPA has also collected nationwide drinking water data for certain PFAS, a summary of which can befound here: https://www.epa.gov/sites/production/files/2017-02/documents/ucmr3-data-summary-january2017.pdf. Such data were further analyzed in, e.g., Guelfo, J.L. and D.T. Adamson. 2018. “Evaluation of anational data set for insights into sources, composition, and concentrations of per- and polyfluoroalkyl
substances (PFASs) in U.S. drinking water.” Environmental Pollution 236 (May): 505-513. Additionally, many
U.S. states have also published data on the occurrence of PFAS in drinking water on their websites. Such data
were recently analyzed in Andrews, D.Q. and Naidenko, O.V. 2020. Population-wide exposure to per- andpolyfluoroalkyl substances from drinking water in the United States. Enviornmental Science & Technology
Letters 7(12): 931–936.
FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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PFOA: <0.56–104 ng/L (19/25)
PFNA: <0.094–38.6 ng/L (22/25)
PFDA: <0.084–24.7 ng/L (13/25)
PFUnDA: <0.067–1.85 ng/L
(4/25)
PFDoDA: <0.062–0.09 ng/L
(1/25)PFTrDA: <0.072 ng/L (0/25)
PFTeDA: <0.13 ng/L (0/25)
PFHxDA: <0.4 ng/L (0/25)
PFOcDA: <0.29 ng/L (0/25)
air
surface watersoil
sedimentone
multipleAsia,
2010 &
2012

PFHxA: ND–0.05 ng/g dw (6/27)[14]

PFHpA: ND–0.06 ng/g dw (3/27)
PFOA: ND–0.28 ng/g dw (24/27)
PFNA: ND–0.15 ng/g dw (24/27)
PFDA: ND–0.08 ng/g dw (24/27)
PFDoDA: ND–0.09 ng/g dw(23/27)

Snow (ski area)

Remote regions

Ice (41 cm
depth)

Northern
Europe,2010one
multiple

Arctic,2017

PFUnDA: 0.01–0.13 ng/g dw(27/27)PFHxA: <4.0–15.9 ng/L (7/8)
PFHpA: <13.3 ng/L (0/8)
PFOA: <7.8–55.5 ng/L (6/8)
PFNA: <11.2–19.6 ng/L (1/8)
PFDA: <4.15–17.2 ng/L (6/8)
PFUnDA: <3.16–12.8 ng/L (5/8)
PFDoDA: <0.168–21.8 ng/L (7/8)
PFTrDA: <1.72–22.0 (6/8)
PFTeDA: <0.377–57.9 (7/8)
PFPeDA: <0.615–16.8 ng/L (5/8)
PFHxDA: <1.36–108 ng/L (5/8)
PFHpDA: <1.4–55.9 ng/L (4/8)
PFOcDA: <5.59–786 ng/L (5/8)
PFNDA: <4.03–60.6 ng/L (3/8)
PFEiA: <3.29–113 ng/L (4/8)
TFA: 137 ng/L (1/1)

[45]

[46]

PFPrA: 6.3 ng/L (1/1)
PFBA: 1.5 ng/L (1/1)

WWTP

effluent
sludgeone
multiple

Europe,2007

PFPeA: 1.5–40.9 ng/L (9/9)[47]

PFHxA: 3.7–57.4 ng/L (9/9)
PFHpA: 1.6–15.7 ng/L (9/9)
PFOA: 12.3–77.6 ng/L (9/9)
PFNA: 1.0–18.6 ng/L (9/9)
PFDA: 0.9–34.5 ng/L (9/9)

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

ENV/CBC/MONO(2022)1  23

PFUnDA: <0.004–8.8 ng/L (7/9)
PFDoDA: <0.01–0.5 ng/L (3/9)
effluent
sludgeone
multiple

UnitedStates,2012 &
2013

PFHxA: 3.67–99.0 ng/L (28/28)[57]

PFHpA: ND–12.9 ng/L (27/28)
PFOA: 5.70–38.8 ng/L (28/28)
PFNA: 0.83–4.95 ng/L (28/28)
PFDA: 1.11–4.43 ng/L (28/28)
PFUnDA: ND–0.92 ng/L (16/28)
PFDoDA: ND–5.91 ng/L (9/28)

Landfillleachate andimpactedgroundwater(historic =closed 25-90
years)

Indoorenvironment

Indoor air (hotel
rooms)

one
multiple

Canada,2021

PFBA: NR–0.29 μg/L
PFPeA: NR–0.21 μg/L
PFHxA: NR–0.67 μg/L
PFHpA: NR–0.27 μg/L
PFOA: NR–0.85 μg/L
PFNA: NR–1.0 μg/L
PFDA: NR–0.006 μg/L
PFUnA: NR–0.016 μg/L
PFDoDA: NR–0.001 μg/L
PFTriDA: NR–0.007 μg/L
PFTeDA: NR–0.0002 μg/L

[58]

one
multiple

Asia,
2015

C4–C7-PFCAs: 0.0444–0.541
ng/m3 (13/13)[48]> C7-PFCAs: 0.0568–0.756 ng/m3(13/13)
Indoor air(residential
homes)

C4–C7-PFCAs: 0.351–1.970 ng/m3(19/19)Indoor dust
(hotel rooms)

C4–C7-PFCAs: ND–170 ng/g
(7/13)> C7-PFCAs: 0.091–0.686 ng/m3(19/19)> C7-PFCAs 11.5–775 ng/g
(13/13)C4–C7-PFCAs: 41.6–226 ng/g
(19/19)Indoor dust
(residential
homes)
Vegetation

Tree leaves> C7-PFCAs: 10.7–205 ng/g
(19/19)one
multiple

North
America,2009

PFHpA: 2.4–7.3 ng/g dw (19/19)[43]

PFOA: 200–700 ng/g dw (19/19)
PFNA: 0.36–5.8 ng/g dw (19/19)
PFDA: 1.2–4.3 ng/g dw (19/19)
PFUnDA: 1.6–8.6 ng/g dw(19/19)FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified24  ENV/CBC/MONO(2022)1
PFDoDA: <0.216–4.2 ng/g dw(15/19)Wildlife

one
multiple

PlanktonAsia,
2010 &
201212

PFNA: ND–0.50 ng/g ww (10/12)[14]

PFDA: ND–0.39 ng/g ww (1/12)
PFUnDA: ND–0.44 ng/g ww(6/12)
PFDoDA: ND–1.08 ng/g ww(7/12)

Crucian carp,
blood

Asia,
2010 &
2012

PFHxA: ND–0.36 ng/ml (7/69)[14]

PFOA: ND–0.89 ng/ml (24/69)
PFNA: ND–13.22 ng/ml (16/69)
PFDA: 0.44–20.58 ng/ml (69/69)
PFUnDA: 0.88–45.16 ng/ml(69/69)PFDoDA: 0.11–19.18 ng/ml(69/69)Crucian carp,
liver

Asia,
2010 &
2012

PFOA: ND–0.33 ng/g ww (9/69)[14]

PFNA: ND–0.86 ng/g ww (30/69)
PFDA: 0.06–3.48 ng/g ww(69/69)PFUnDA: 0.04–5.01 ng/g ww(69/69)PFDoDA: ND–2.08 ng/g ww(67/69)Peregrine
falcons, plasma

12one
multiple

Canada,2016 &
2018

PFBA: ND–6.70 ng/g ww (5/57)
PFPeA: ND–0.23 ng/g ww (3/57)
PFHxA: ND–3.56 ng/g ww(41/57)
PFHpA: ND–3.14 ng/g ww(28/57)
PFOA: 0.17–2.38 ng/g ww(57/57)
PFNA: 0.83–21.8 ng/g ww(57/57)
PFDA: 0.45–9.65 ng/g ww(57/57)
PFUnDA: 0.78–9.84 ng/g ww(57/57)
PFDoDA: 0.24–3.62 ng/g ww(57/57)
PFTrDA: 0.56–4.49 ng/g ww(57/57)
PFTeDA: 0.22–2.81 ng/g ww(57/57)[59]

PFHxA, PFHpA, and PFOA were not detected in any sample.
FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)

Unclassified

ENV/CBC/MONO(2022)1  25

PFHxDA: 0.09–3.00 ng/g ww(55/57)PFODA: 0.01–1.08 ng/g ww(18/57)

Human serum

Peregrine
falcons, egg

one
multiple

Canada,2018

PFBA: ND ng/g ww (0/9)
PFPeA: ND–0.64 ng/g ww (8/9)
PFHxA: 0.06–0.09 ng/g ww (9/9)
PFHpA: ND–0.06 ng/g ww (8/9)
PFOA: 0.11–0.31 ng/g ww (9/9)
PFNA: 0.46–4.05 ng/g ww (9/9)
PFDA: 0.90–3.49 ng/g ww (9/9)
PFUnDA: 1.12–7.22 ng/g ww(9/9)
PFDoDA: 1.47–4.05 ng/g ww(9/9)
PFTrDA: 1.93–8.18 ng/g ww (9/9)
PFTeDA: 1.40–5.25 ng/g ww(9/9)
PFHxDA: 0.19–0.46 ng/g ww(9/9)
PFODA: ND–0.03 ng/g ww (7/9)

generalpopulation
occupational
exposureone
multiple

Asia,
2011

TFA: 5.36–12.55 ng/ml (244/252)[49]

PFPrA: 0.24–0.82 ng/ml(194/252)
PFBA: 0.31–0.89 ng/ml (216/252)
PFHxA: 0.41–0.76 ng/ml(251/251)
PFHpA: ND–0.18 ng/ml(168/252)
PFOA: 8.45–26.76 ng/ml(252/252)
PFNA: 1.99–5.20 ng/ml (252/252)
PFDA: 0.96–4.11 ng/ml (250/252)
PFUnDA: 1.71–3.02 ng/ml(252/252)
PFDoDA: 0.07–0.21 ng/ml(224/252)

generalpopulation
occupational
exposure

Canada,20162017

PFOA: 1.3 ng/ml (mean;
2593/2593)
PFNA: 0.51 ng/ml (mean;
2413/2442)
PFDA: 0.18 ng/ml (mean;
2157/2360)[65]

generalpopulation
occupational
exposureNorth
America,2015–

PFNA: 0.577 ng/ml (mean;
NR/1993)
PFDA: 0.154 ng/ml (mean;
NR/1993)[66]

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified26  ENV/CBC/MONO(2022)1
2016
Children age 311

North
America,
2013–
2014

PFOA: 1.56 ng/ml (mean;
NR/1993)
PFOA (linear): <0.07–8.22 ng/ml(638/639)
PFOA (branched): <0.07–0.69
ng/ml (163/639)
PFHpA: <0.07–0.97 ng/ml(124/639)
PFNA: <0.07–52.92 ng/ml(638/639)
PFDA: <0.07–2 ng/ml (300/639)
PFUnDA: <0.07–2.83 ng/ml(208/639)
PFDoDA: <0.07 ng/ml (0/639)[50]

Other known occurrences and sources
Many other PFASs, such as fluorotelomer-based substances, can yield PFCAs upon degradation, including
atmospheric oxidation of volatile precursors [9], [51], [52], [54]. For example, degradation (e.g. via OHradicals) of fluoroalkylsilane substances can yield significant amounts of PFCAs [53].
Knowledge gaps
- Little is known about the uses, occurrence, and environmental fate of PFdiCAs.
- Current production volumes of PFCAs and PFdiCAs are unknown.
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Unclassified28  ENV/CBC/MONO(2022)1

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Unclassified

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S. Kleywegt, M. Raby, S. McGill, and P. Helm, “The impact of risk management measures on theconcentrations of per-and polyfluoroalkyl substances in source and treated drinking waters in Ontario,
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N. S. Rao, and B. E. Baker, “Textile Finishes and Fluorosurfactants,” in Organofluorine Chemistry.
Principles and Commercial Applications, R. E. Banks, B. E. Smart, and J. C. Tatlow, Eds. New York:
Springer Science + Business Media, LLC, 1994
B. Subedi et al., “A pilot study on the assessment of trace organic contaminants including
pharmaceuticals and personal care products from on-site wastewater treatment systems along
Skaneateles Lake in New York State, USA,” Water Research, vol. 72, no. 19, pp. 28–39, 2015.
V. R. Propp, A. O. De Silva, C. Spencer, S. J. Brown, S. D. Catingan, J. E. J. W. R. Smith, “Organic
contaminants of emerging concern in leachate of historic municipal landfills,” Environ. Pollut., vol.
276, 116474, 2021. https://doi.org/10.1016/j.envpol.2021.116474.
J. Sun, R. J. Letcher, M. Eens, A. Covaci, and K. J. Fernie, “Perfluoroalkyl acids and sulfonamides anddietary, biological and ecological associations in peregrine falcons from the Laurentian Great Lakes
Basin, Canada,” Env. Res., vol. 191, pp. 110151, 2020.
M. K. Björnsdotter, L. W. Y. Yeung, A. Kärrman, and I. E. Jogsten, “Ultra-Short-Chain Perfluoroalkyl
Acids Including Trifluoromethane Sulfonic Acid in Water Connected to Known and Suspected Point
Sources in Sweden,” Environ. Sci. Technol., vol. 53, pp. 11093–11101, 2019.
S. Felizeter, M. S. McLachlan, and P. de Voogt, “Uptake of Perfluorinated Alkyl Acids byHydroponically Grown Lettuce (Lactuca sativa),” Environ. Sci. Technol., vol. 46, pp. 11735–11743,
2012.
S. Felizeter, M. S. McLachlan, and P. de Voogt, “Root Uptake and Translocation of PerfluorinatedAlkyl Acids by Three Hydroponically Grown Crops,” J. Agric. Food Chem., vol. 62, pp. 3334–3342,
2014.
S. Zhao, S. Fang, L. Zhu, L. Liu, Z. Liu, and Y. Zhang, “Mutual impacts of wheat (Triticum aestivumL.) and earthworms(Eisenia fetida) on the bioavailability of perfluoroalkyl substances(PFASs) in soil,”
Environ. Pollut., vol. 184, pp. 495-501, 2014.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified30  ENV/CBC/MONO(2022)1
[64]

[65]
[66]
[67]

L. Gobelius, J. Lewis, and L. Ahrens, “Plant Uptake of Per- and Polyfluoroalkyl Substances at a
Contaminated Fire Training Facility to Evaluate the Phytoremediation Potential of Various Plant
Species,” Environ. Sci. Technol., vol. 51, pp. 12602–12610, 2017.
Health Canada, “Fifth Report on Human Biomonitoring of Environmental Chemicals in Canada,” 2019.
U.S. CDC, “Fourth National Report on Human Exposure to Environmental Chemicals: Updated Tables,
March 2021. Volume Two: NHANES 2011-2016,” 2021.
Daikin Kogyo KK, JP-Kokai 84 048436, 1982 (S. Misaki, T. Kamifukikoshi, M. Suefuji). Referenced
in: G. Siegemund, W. Schwertfeger, A. Feiring, B. Smart, F. Behr, H. Vogel, and B. McKusick,“Fluorine Compounds, Organic,” Ullmann’s Encycl. Ind. Chem., Wiley-VCH, 2000.
https://doi.org/10.1002/14356007.a11_349.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

ENV/CBC/MONO(2022)1  31

3. Perfluoroalkane sulfonic (a) and sulfinic (b) acids
Chemical Information & Properties
Identification and Terminology13
Name

Perfluoroalkane sulfonic acids

Perfluoroalkane sulfinic acids

Other Names

Perfluoroalkyl sulfonic acids;
fluorinated alkanesulfonic acids

Perfluoroalkyl sulfinic acids;
fluorinated alkanesulfinic acids

AcronymPFSAs

PFSIAsChemical Formula

CnF2n+1SO2OH

CnF2n+1SOOH

US EPA CompTox
Markush IDDTXSID70892979

DTXSID801024681

Individual
Acronyms (as usedin this document)

Short-chain PFSAs (n ≤5): PFBS: n=4; PFPeS: n=5
Long-chain PFSAs (n ≥6): PFHxS: n=6; PFHpS:
n=7; PFOS: n=8; PFNS: n=9; PFDS: n=10

PFOSI: n=8 (other PFSIAs exist,
but no information on those wasavailable)

General Structure(linear isomers)

Degradability, Mobility, Bioconcentration
General remarks

PFOS and other long-chain PFSAs are known to bebioaccumulative and persistent in the environment[1], with PFHxS being the most bioaccumulative
PFAS known [2]. Short-chain PFSAs (n ≤ 5) areless bioaccumulative, but are expected to be ofsimilar persistence [1], [4].

Photochemicaldegradation

PFOS photolyzes slowly under UV C light (100–280 nm), with complete degradation in 11 days [5].

Hydrolysis

PFOS hydrolyzes at high temperatures (300 °C) [6].

Biodegradation

No biodegradation of PFOS observed [7].
PFSAs are not effectively removed by conventional
activated sludge processes in WWTP [8], [9].14

Adsorption onorganic matter(log Kd, cm3/g)

Log Koc = 2.68 (PFOS, in sediment) [10]Partitioncoefficients (Kd,sediment–water)

0.03 (PFHxS); 0.07 (PFOS) [11](measured in Korea, n=17)

PFSIAs are transformed to PFSAs
in the environment. [3]13For more examples of compounds in the group of PFSAs and their associated information, one may searchfor “DTXSID70892979” at the U.S. EPA CompTox Chemicals Dashboard: https://comptox.epa.gov/dashboard
14
In one study, PFOS was found to partially degraded (removal of up to 60% over 100 day inoculations) by aspecific bacterial strain (Acidimicrobium sp. Strain A6) under laboratory conditions where they were used as
the sole source of carbon; the applicability of this method in the field environment is currently unclear. [56]
FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified32  ENV/CBC/MONO(2022)1
Bioaccumulation
potential

PFOS: depuration half-life (rainbow trout) = 13d
Blood elimination half-life (rat, male) = 8–30d [7]Short-chain PFSAs (PFBS) are accumulating inplants and trees [12-15].
In various crops (lettuce, tomato, cabbage,
zucchini) PFBS and PFHxS accumulate rather inleaves, whereas PFOS accumulates rather in roots.
In trees (birch, spruce), the highest BCF values havebeen found in foliage. [56]–[59]TMF in the overall
Arctic marine foodweb [16]
TMF in riverine
systems [17]PFOS: 17.4

BAF (earthworm)

PFHxS: 0.36–3.7
PFHpS: 0.65–8.3
PFOS (linear): 0.81–4.5
PFOS (branched): 1.4–8.3
PFDS: 0.73–3.0
PFBS: 0.21–0.92
PFHxS: 0.51–4.69 [18]BMF (different
species)PFHxS: 6.9–22 [19]; 20 [20]
PFOS: 30 [20]PFDS: 36 [20]

BCF15 (carp,
liver/blood, [L/kg])

PFHxS: 8 / 342
PFOS: 4572 / 11,167 [11]Synthesis
Main Synthesis
MethodMostly the Simons electrochemical fluorination process is used, where the hydrocarbon
sulfonyl fluoride is electrolyzed in anhydrous hydrogen fluoride:𝐶𝑛 𝐻2𝑛+1 𝑆𝑂2 𝐹 + (2𝑛 + 1)𝐻𝐹 →𝐶𝑛 𝐹2𝑛+1 𝑆𝑂2𝐹 + (2𝑛 + 1)𝐻2
Alternatively, a nonelectrochemical route for the synthesis of trifluoromethanesulfonicacid derivatives is also possible:
𝐹3 𝐶 − 𝑆 − 𝑆 − 𝐶𝐹3 →𝐶𝑙2

2 𝐹3 𝐶 − 𝑆 − 𝐶𝑙 →

𝐶𝑙2
𝐻2 𝑂

2 𝐹3 𝐶 − 𝑆𝑂2 𝐶𝑙

Alkaline hydrolysis then gives the sulfonate salt, which can be acidified to yield the acid.
[21]
PFSIAs are similarly also synthesized via electrochemical fluorination [1].
Possible Impurities

The electrochemical fluorination process is unselective and yields, besides the target
compound, a mixture of linear, branched, and cyclic homologues, which can be found as
impurities in the final product [1], [22]. Product yields decrease with increasing chain
lengths [23].

15Note that due to the acidic nature and the proteinophilic properties of PFSAs, BCFs are not necessarily
accurate indicators of their overall biomagnification behavior in aquatic organisms. [10]FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

ENV/CBC/MONO(2022)1  33

Industrial Practices & Commercial Uses
Major Commercial Products
Name

Perfluorooctane sulfonic acid (PFOS)CAS Number

1763-23-1

Production/Import
volumes

PFOS production was phased out in the US (in 2002), but it is still being produced in
China. The production volume of perfluorooctane sulfonyl fluoride (the parent compoundof PFOS) in China in 2006 was more than 200 tonnes [1]. Global production between
2003 and 2008 reached 410 tonnes, mainly in China, followed by Japan and Germany[24]. Production volumes in 2015 were estimated at 170 tonnes per year in China [25].

Uses

Surfactant [1] (e.g. potassium salt of PFOS, CAS Number 2795-39-3, as a mist
suppressant in electroplating) [24]NamePotassium perfluorobutanesulfonate (K-PFBS)CAS Number

29420-49-3

Production/Import
volumes

Registered under REACH with a production/import volume of 100–1000 tonnes/yr inEurope. [26]Uses

Mainly used as flame retardant in polycarbonate, but also as intermediate in the synthesisof other chemicals. [27]Uses
Major applications

Short-chain PFSAs are used as esterification catalysts, as electrolytes in fuel cells andbatteries (in the form of their lithium salts), as antistatic agents, and as flame retardants(K-PFBS is mainly used as flame retardant in polycarbonate) [27], [21]. Longer-chain
PFSAs are used as surfactants and in fire extinguishing formulations [21].
PFSIAs themselves are not commercially used, but are known degradation products
formed from perfluoroalkane sulfonamides. [1]Regulatory Status
General remarks

Current risk assessment and regulations mainly focus on PFHxS and PFOS, with shortchain PFSAs such as PFBS being used as replacements [4], [22].
Many limit values for different environmental media have been set at regional, country
and sub-country levels, and a comprehensive overview is available online by the US
Interstate Technology Regulatory Council (ITRC) at https://pfas-1.itrcweb.org/factsheets/ (see “PFAS Water and Soil Values Table”). [28]USThrough its voluntary agreement with US EPA, 3M (the then largest manufacturer)
phased out its global production of PFOS in 2002. [32] US EPA promulgated Significant
New Use Rules (SNURs) in 2002 and 2007 under the Toxic Substances Control Act(TSCA) that require manufacturers (including importers) and processors to notify US
EPA at least 90 days before starting or resuming manufacture, import, or processing forsignificant new uses of 271 PFSAs and related compounds, essentially encompassing all
PFSAs and related compounds on the US market. Articles (except carpets) containing
these substances may still be imported. [33]In March 2020, US EPA made a preliminary determination to regulate PFOS in drinking
water. US EPA finalized regulatory determinations in February 2021. In addition, certain
PFSAs have been regulated at the state level in the US. [34]PFOS, its salts and precursors were assessed in 2006 and are prohibited with a limited
number of exemptions under the Prohibition of Certain Toxic Substances Regulations,2012 [35], [36].

CanadaFACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified34  ENV/CBC/MONO(2022)1
EuropePFOS added to the restricted substances list (REACH Annex XVII) in 2017 [37].
In 2018, EFSA set the tolerable week intake (TWI) for PFOS to 13 ng/kg bw [38] and in
2020, EFSA set a TWI value for the sum of PFOA, PFNA, PFHxS and PFOS of 4.4 ng/kg
bw [39].
The EU Water Framework Directive set an EQS (environmental quality standard) value
for PFOS (and its derivatives) in surface waters of 0.65 ng/L [40].
PFBS and PFHxS (and their salts) are identified as SVHCs [41], [42].

International efforts
2002: OECD classified PFOS as a PBT chemical. [29]2009: PFOS, its salts and perfluorooctane sulfonyl fluoride added to Annex B (Restriction) to the Stockholm
Convention as persistent organic pollutants (POPs) [53], with specific exemptions and acceptable purposes
amended in 2019 [54].
2013: Perfluorooctane sulfonic acid, perfluorooctane sulfonates, perfluorooctane sulfonamides andperfluorooctane sulfonyls added to Annex III to the Rotterdam Convention on the Prior Informed Consent
Procedure for Certain Hazardous Chemicals and Pesticides in International Trade. [55]PFHxS, its salts and related compounds are recommended by the Persistent Organic Pollutants Review
Committee (POPRC) to the Stockholm Convention for listing under the Convention (to be determined by the
Conference of the Parties (COP) in 2022). [30], [31]Examples of reported occurrences
Type oflocations/samples(Environmental)
media

Detected in
one ormultipleregions

ExamplesLocation,year

Levels [min. –max. (detection
frequency)]

Ref.

Note: Non-detects are reported as below the value of the limit of detection (“<LOD”).
pg = picograms, ng = nanograms, dw = dry weight, ww = wet weight, ND = not detected, NR = not reported
airone
Close toNetherlands PFBS: 16–27 ng/L (13/13)[43]
surface water
fluorochemical
multiple 2016
PFHxS: 1.5–2.2 ng/L (13/13)
soil
manufacturing
PFHpS: 0.095–0.2 ng/L (13/13)
park
sediment
PFOS: 2.7–6.5 ng/L (13/13)
airone
Not close to
Korea
PFHxS: ND–3.97 ng/L (18/19)[11]
surface water
multiple
specific point2010 &PFOS: 0.25–15.07 ng/L (19/19)
soil
sources2012
sediment
PFBS: 0.9–3.4 ng/L (15/15)
Germany[44]
2007
PFHxS: 0.3–1.3 ng/L (15/15)
PFOS: 0.5–2.9 ng/L (15/15)
PFOSI: <0.01–0.1 ng/L (1/15)
one
multiple

Brazil2015

PFBS: 0.48–16 ng/L (19/21)

France2015

PFBS: 2.0–15 ng/L (5/8)[45]

PFOS: 4.6–44 ng/L (21/21)[46]

PFOS: 12–30 ng/L (3/8)
PFDS: 5.9–12 ng/L (3/8)
PFBS: 2.8–24 ng/L (9/29)

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

ENV/CBC/MONO(2022)1  35

Drinking water16

Spain
2015

PFOS: 2.0–140 ng/L (11/29)[45]

Netherlands
2016

PFBS: 0.54–19.0 ng/L (6/6)[43]

PFHxS: 0.02–0.43 ng/L (6/6)
PFHpS: <0.02–0.03 ng/L (3/6)
PFOS: <0.03–0.41 ng/L (5/6)

Drinking water
treatment plant(DWTP) influent

Canada2012–2016

PFBS: <1–8.3 ng/L (14/226)
PFHxS: <1–2.6 ng/L (43/226)
PFOS: <0.5–5.9 ng/L (113/226)
PFDS: <1 ng/L (0/226)

[61]

North
America,
2013–2015

PFBS: <0.032–11.1 ng/L (24/25)
PFHxS: <0.034–44.8 ng/L (23/25)[46]

PFOS: <0.13–48.3 ng/L (22/25)
PFDS: <0.049 ng/L (0/25)

DWTP effluent

PFBS: <0.032–11.9 ng/L (24/25)
PFHxS: <0.034–21.1 ng/L (20/25)[46]

PFOS: <0.13–36.9 ng/L (20/25)
PFDS: <0.049 ng/L (0/25)
air
surface watersoil
sediment
air
surface watersoil
sedimentone
multiple

Korea
2010 &
2012

PFHxS: ND–0.01 ng/g dw (9/27)

one
multiple

North
America2016∑PFSAs: 0.035–1.99 ng/g dw(33/33)

Europe2016∑PFSAs: ND–3.27 ng/g dw (9/10)

Asia 2016∑PFSAs: 0.079–0.421 ng/g dw(6/6)

Africa 2016

∑PFSAs: ND–0.144 ng/g dw (4/5)

Australia
2016∑PFSAs: 0.044–0.297 ng/g dw
(4/4)

South
America2016∑PFSAs: 0.026–0.048 ng/g dw
(3/3)

[11]

PFOS: 0.01–0.048 ng/g dw(27/26)[47]

16

U.S. EPA has also collected nationwide drinking water data for certain PFAS, a summary of which can befound here: https://www.epa.gov/sites/production/files/2017-02/documents/ucmr3-data-summary-january2017.pdf. Such data were further analyzed in, e.g., Guelfo, J.L. and D.T. Adamson. 2018. Evaluation of anational data set for insights into sources, composition, and concentrations of per- and polyfluoroalkyl
substances (PFASs) in U.S. drinking water. Environmental Pollution 236 (May): 505–513. Additionally, many
U.S. states have also published data on the occurrence of PFAS in drinking water on their websites. Such data
were recently analyzed in Andrews, D.Q. and Naidenko, O.V. 2020. Population-wide exposure to per- andpolyfluoroalkyl substances from drinking water in the United States. Environmental Science & Technology
Letters 7(12): 931–936.
FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified36  ENV/CBC/MONO(2022)1
Remoteregionsair
surface watersoil
sedimentone
multiple

Antarctica
2016∑PFSAs: 0.007 ng/g dw (1/1)

[47]

WWTP

effluent
sludgeone
multiple

Germany
2007

PFBS: 1.8–25.9 ng/L (9/9)[44]

PFHxS: 0.3–6.3 ng/L (9/9)
PFHpS: <0.08–0.5 ng/L (3/9)
PFOS: <0.06–82.2 ng/L (7/9)
PFOSI: 0.1–1.2 ng/L (9/9)

effluent
sludgeLandfillleachate andimpactedgroundwater(historic, i.e.
closed 25–90
years)
Indoorenvironment

Wildlife

Indoor air (hotel
rooms)

one
multiple

UnitedStates 2012
& 2013

PFBS: ND-14.0 ng/L (23/28)
PFHxS: ND-2.48 ng/L (25/28)
PFOS: 2.18-94.4 ng/L (28/28)

[62]

one
multiple

Canada,2018

PFBS: NR–710 ng/L (NR)PFHxS: NR–1300 ng/L (NR)
PFOS: NR–2800 ng/L (NR)PFDS: NR–2 ng/L (NR)
FOSA: NR–13 ng/L (NR)PFECHS: NR–9500 ng/L (NR)

[63]

one
multiple

China
2015

∑PFSA: 0.0712–0.231 ng/m3(13/13)[48]

Indoor air(residential
homes)∑PFSA: 0.0868–0.567 pg/m3(19/19)Indoor dust
(hotel rooms)∑PFSA: 2.44–99.1 ng/g (13/13)

Indoor dust
(residential
homes)∑PFSA: 3.43–72.5 ng/g (19/19)

one
multiple

Plankton
Crucian carp,
blood

Korea
2010 &
2012

PFOS: ND–12.67 ng/g ww (6/12)[11]

PFHxS: ND–4.96 ng/ml (26/69)[11]

PFOS: 0.18–145.23 ng/ml (69/69)
PFDS: ND–0.60 ng/ml (1/69)
PFHxS: ND–0.30 ng/g ww (4/69)

Crucian carp,
liver

[11]

PFOS: ND–43.76 ng/g ww(58/69)PFDS: ND–0.58 ng/g ww (9/69)

Harbor seals(Phoca vitulina,
liver)

Germany
2007

PFBS: ND–0.78 ng/g ww (NR)

[49]

PFPeS: 0.13–5.38 ng/g ww (NR)PFHxS: 1.11–10.4 ng/g ww (NR)PFHpS: ND–5.43 ng/g ww (NR)

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

ENV/CBC/MONO(2022)1  37

PFOS: 559–1665 ng/g ww (NR)PFNS: 0.12–1.80 ng/g ww (NR)PFDS: 0.11–1.02 ng/g ww (NR)PFOSI: ND–0.16 ng/g ww (NR)
Eggs of Northern
Fulmars andThick-Billed
MurresNorth
America,
2010-2011

PFBS: <0.1–0.57 ng/g ww (rangeof means, NR/60)[50]

PFHxS: <0.1–0.13 ng/g ww(range of means, NR/60)
PFOS: <19.8–27.4 ng/g ww(range of means, NR/60)
PFDS: <0.2 ng/g ww (NR/60)

Human serum

Ringed seals(Pusa hispida)
plasmaNorthern
Europe,2010

PFBS: <0.07 ng/g ww (mean,
NR/11)PFHxS: 1.29 ng/g ww (mean,
NR/11)PFOS: 48 ng/g ww (mean, NR/11)
PFDS: <0.07 ng/g ww (mean,
NR/11)[51]

Peregrine
falcons, plasma

Canada,2016 &
2018

PFEtCHxS: ND–3.96 ng/g ww(36/57)
PFBS: ND–3.47 ng/g ww (27/57)
PFHxS: ND–4.89 ng/g ww(56/57)
PFOS: 4.97–124 ng/g ww (57/57)
PFDS: ND–8.31 ng/g ww (53/57)[64]

Peregrine
falcons, egg

Canada,2018

PFEtCHxS: ND–0.26 ng/g ww(7/9)
PFBS: ND–0.10 ng/g ww (3/9)
PFHxS: 0.09–0.92 ng/g ww (9/9)
PFOS: 11.8–53.2 ng/g ww (9/9)
PFDS: 0.90–2.63 ng/g ww (9/9)

generalpopulation
occupational
exposureNorth
America,
2015–2016

PFHxS: 1.18 ng/ml (mean;
NR/1993)
PFOS: 4.72 ng/ml (mean;
NR/1993)[65]Children age 3–
11

North
America,
2013–2014

PFBS: <0.07–0.17 ng/ml (27/639)
PFHxS: <0.07–12.9 ng/ml(638/639)
PFOS (linear): <0.07–26.54 ng/ml(639/639)
PFOS (branched): <0.07–10.68
ng/ml (639/639)[52]

generalpopulation

Canada,2016-2017

PFHxS: 0.9 ng/ml (mean;[66]

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified38  ENV/CBC/MONO(2022)1
occupational
exposure

2587/2595)
PFOS: 3.0 ng/ml (mean;
2591/2594)

Knowledge gaps

- Very little is known about the use, occurrence, and environmental fate of PFSIAs.
- Current production volumes are only available as estimates.
- More information on PFHxS and PFBS can be found in their EU REACH SVHC dossiers and in the
PFHxS risk profile under the Stockholm Convention [13], [41], [42], [19].
References
[1]
[2]

[3]
[4]
[5]
[6]

[7]
[8]

[9]

[10]
[11]
[12]
[13]
[14]

[15]

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Z. Wang, I. T. Cousins, M. Scheringer, and K. Hungerbühler, “Fluorinated alternatives to long-chain
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Environ. Sci. Technol., vol. 51, pp. 12602–12610, 2017.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

ENV/CBC/MONO(2022)1  39

[16]

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[23]
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PFAS concentrations bracketing environmental relevance”, Chemosphere., vol. 199, pp. 168–173, 2018.
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H. Lehmler, “Synthesis of environmentally relevant fluorinated surfactants—a review,” Chemosphere,
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C. Lassen et al., “Survey of PFOS, PFOA and other perfluoroalkyl and polyfluoroalkyl substances,” The
Danish Environmental Protection Agency, Copenhagen, 2013.
Z. Wang, J. Boucher, M. Scheringer, I. Cousins, and K. Hungerbuehler, “Toward a Comprehensive
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29-Jul-2019].
European Chemicals Agency, “Report of the Persistent Organic Pollutants Review Committee on thework of its fifteenth meeting. Addendum: Risk management evaluation on perfluorohexane sulfonic acid
(PFHxS), its salts and PFHxS-related compounds,” 2019.
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Organisation for Economic Co-operation and Development (OECD), “Co-operation on existingchemicals. Hazard assessment of perfluorooctane sulfonate (PFOS) and its salts,” in Environment
Directorate the Joint Meeting of the Chemicals Committee and Working Party on Chemicals, Pesticides
and Biotechnology, ENV/JM/RD(2002)17/FINAL, Paris, France, 2002.
Stockholm Convention on Persistant Organic Pollutants, ““Report of the Persistent Organic Pollutants
Review Committee on the work of its fifteenth meeting,” 2019. Decision POPRC-15/1.
Secretariat of the Basel, Rotterdam and Stockholm Conventions “Meetings of the conferences of theParties to the Basel, Rotterdam and Stockholm conventions,”. [Online]. Available:
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U.S. Environmental Protection Agency, “Long-Chain Perfluorinated Chemicals (PFCs) Action Plan,”
2009.
USA, “40 CFR §721.9582. Certain perfluoroalkyl sulfonates,” Avaible at: https://www.ecfr.gov/cgibin/textidx?SID=c8175aed22d0b9446beca21293ba915f&mc=true&node=se40.33.721_19582&rgn=div8
U.S. Environmental Protection Agency, “Regulatory Determination 4,” 2020. [Online]. Available:
https://www.epa.gov/ccl/regulatory-determination-4. [Accessed: 21-Dec-2020].
Environment Canada, “Screening assessment: Perfluorooctane sulfonic acid, its salts and its precursors,”

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified40  ENV/CBC/MONO(2022)1
Environment Canada, Existing Substances Division, Gatineau (QC), 2006. Available at:https://www.canada.ca/en/environment-climate-change/services/canadian-environmental-protectionact-registry/publications/ecological-screening-report-sulfonate.html.
[36] Canada, “Prohibition of Certain Toxic Substances Regulations, SOR/2012-285,” 2016. Available at:https://laws-lois.justice.gc.ca/eng/regulations/SOR-2012-285/index.html.
[37] European Commission, “Commission Regulation (EU) 2017/1000 of 13 June 2017 amending Annex
XVII to Regulation (EC) No 1907/2006 of the European Parliament and of theCouncil concerning the Registration, Evaluation, Authorisation and Restriction of Chemicals(REACH) as regards perfluorooctanoic acid (PFOA), its salts and PFOA-related substances,” Official Journalof the European Union, 2017.[38] EFSA CONTAM Panel, “Risk to human health related to the presenceof perfluorooctane sulfonic acid and perfluorooctanoic acid in food,” EFSA Journal, vol. 16., no. 12,
2018.
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[43]

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[45]
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[49]

[50]

[51]

[52]

EFSA CONTAM Panel, “Risk to human health related to the presence of perfluoroalkyl substances infood,” EFSA Journal, vol. 18., no. 9, 2020.
European Commission, “Directive 2013/39/EU of the European Parliament and of the Council of 12
August 2013 amending directives 2000/60/EC and 2008/105/EC as regards priority substances in the fieldof water policy,” Official Journal of the European Union, vol. 56, 2013.
European Chemicals Agency, “Agreement of the Member State Committee on the Identification of
Perfluorobutane sulfonic acid and its Salts as Substances of Very High Concern According to Articles 57
and 59 of Regulation (EC) 1907/2006,” 2019.
European Chemicals Agency, “Agreement of the Member State Committee on the Identification of
Perfluorohexane-1-sulphonic acid and its Salts as Substances of Very High Concern According to
Articles 57 and 59 of Regulation (EC) 1907/2006,” 2017.
W. A. Gebbink, L. Van Asseldonk, and S. P. J. Van Leeuwen, “Presence of Emerging Per- andPolyfluoroalkyl Substances (PFASs) in River and Drinking Water near a Fluorochemical Production
Plant in the Netherlands,” Environ. Sci. Technol., vol. 51, no. 19, pp. 11057–11065, 2017.
L. Ahrens, S. Felizeter, R. Sturm, Z. Xie, and R. Ebinghaus, “Polyfluorinated compounds in waste water
treatment plant effluents and surface waters along the River Elbe, Germany,” Mar. Pollut. Bull., vol. 58,
no. 9, pp. 1326–1333, 2009.
T. G. Schwanz, M. Llorca, M. Farré, and D. Barceló, “Perfluoroalkyl substances assessment in drinking
waters from Brazil, France and Spain,” Sci. Total Environ., vol. 539, pp. 143–152, 2016.
J. S. Boone et al., “Per- and polyfluoroalkyl substances in source and treated drinking waters of the UnitedStates,” Sci. Total Environ., vol. 653, pp. 359–369, 2019.
K. Rankin, S. A. Mabury, T. M. Jenkins, and J. W. Washington, “A North American and global surveyof perfluoroalkyl substances in surface soils: Distribution patterns and mode of occurrence,”
Chemosphere, vol. 161, pp. 333–341, 2016.
Y. Yao et al., “Per- and Polyfluoroalkyl Substances (PFASs) in Indoor Air and Dust from Homes andVarious Microenvironments in China: Implications for Human Exposure,” Environ. Sci. Technol., vol.
52, no. 5, pp. 3156–3166, 2018.
L. Ahrens, U. Siebert, and R. Ebinghaus, “Total body burden and tissue distribution of polyfluorinatedcompounds in harbor seals (Phoca vitulina) from the German Bight,” Mar. Pollut. Bull., vol. 58, no. 4,
pp. 520–525, 2009.
B. M. Braune, and R. J. Letcher, “Perfluorinated Sulfonate and Carboxylate Compounds in Eggs ofSeabirds Breeding in the Canadian Arctic: Temporal Trends (1975− 2011) and Interspecies Comparison,”Environ. Sci. Technol., vol. 47, pp. 616–624, 2013.
H. Routti, G. W. Gabrielsen, D. Herzke, K. M. Kovacs, and C. Lydersen, “Spatial and temporal trends inperfluoroalkyl substances (PFASs) in ringed seals (Pusa hispida) from Svalbard,” Environ. Pollut., vol.
214, pp.230–238, 2016.
U.S. CDC, “National Health and Nutrition Examination Survey. 2013-2014 Data Documentation,
Codebook, and Frequencies. Perfluoroalkyl and Polyfluoroalkyl Substances in US children 31-11 Years
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Unclassified

ENV/CBC/MONO(2022)1  41

[53]

[54]

[55]

[56]

[57]

[58]
[59]

[60]

[61]

[62]

[63]

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Stockholm Convention on Persistent Organic Pollutants on the work of its fourth meeting,” Geneva, 2009.
Decision SC-4/17.
Stockholm Convention on Persistent Organic Pollutants, “Report of the Conference of the Parties to the
Stockholm Convention on Persistent Organic Pollutants on the work of its ninth meeting,” Geneva, 2019.
Decision SC-9/4.
Rotterdam Convention on the Prior Informed Consent Procedure for Certain Hazardous Chemicals andPesticides in International Trade, “Report of the Conference of the Parties to the Rotterdam Convention
on the Prior Informed Consent Procedure for Certain Hazardous Chemicals and Pesticides in International
Trade on the work of its sixth meeting,” Geneva, 2013. Decision RC-6/7.
S. Huang, and P. R. Jaffe, “Defluorination of Perfluorooctanoic Acid (PFOA) and Perfluorooctane
Sulfonate (PFOS) by Acidimicrobium sp. Strain A6”, Environ. Sci. Technol., vol. 53, pp. 11410–11419,
2019.
S. Felizeter, M. S. McLachlan, and P. de Voogt, “Uptake of Perfluorinated Alkyl Acids byHydroponically Grown Lettuce (Lactuca sativa),” Environ. Sci. Technol., vol. 46, pp. 11735–11743,
2012.
S. Felizeter, M. S. McLachlan, and P. de Voogt, “Root Uptake and Translocation of Perfluorinated Alkyl
Acids by Three Hydroponically Grown Crops,” J. Agric. Food Chem., vol. 62, pp. 3334–3342, 2014.
S. Zhao, S. Fang, L. Zhu, L. Liu, Z. Liu, and Y. Zhang, “Mutual impacts of wheat (Triticum aestivum L.)and earthworms(Eisenia fetida) on the bioavailability of perfluoroalkyl substances(PFASs) in soil,”
Environ. Pollut., vol. 184, pp. 495-501, 2014.
L. Gobelius, J. Lewis, and L. Ahrens, “Plant Uptake of Per- and Polyfluoroalkyl Substances at a
Contaminated Fire Training Facility to Evaluate the Phytoremediation Potential of Various Plant
Species,” Environ. Sci. Technol., vol. 51, pp. 12602–12610, 2017.
S. Kleywegt, M. Raby, S. McGill, and P. Helm, “The impact of risk management measures on theconcentrations of per-and polyfluoroalkyl substances in source and treated drinking waters in Ontario,
Canada,” Sci. Total Environ., vol. 748, pp. 141195, 2020.
B. Subedi et al., “A pilot study on the assessment of trace organic contaminants including pharmaceuticals
and personal care products from on-site wastewater treatment systems along Skaneateles Lake in New
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Health Canada, “Fifth Report on Human Biomonitoring of Environmental Chemicals in Canada,” 2019.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified42  ENV/CBC/MONO(2022)1

4. Per- and polyfluoroalkylether carboxylic (a) and sulfonic (b) acids
Key publication: Wang, Zhanyun, Ian T. Cousins, Martin Scheringer, and Konrad
Hungerbuehler. 2015. “Hazard Assessment of Fluorinated Alternatives to Long-Chain
Perfluoroalkyl Acids (PFAAs) and Their Precursors: Status Quo, Ongoing Challenges andPossible
Solutions.”
Environment
International75:
172–79.
https://doi.org/10.1016/j.envint.2014.11.013.

Chemical Information & Properties
Identification and Terminology
NamePer- and polyfluoroether carboxylic
acidsPer- and polyfluoroether sulfonic acids

Acronym

PFECAsPFESAsExemplary Chemical
FormulaCnF2n+1OCmF2mCOOH

CnF2n+1OCmF2mSO3HDTXSID001024687

DTXSID301024686

Exemplary Structure(perfluorinated ones
and linear isomers)

US EPA CompTox
Markush ID

Degradability, Mobility, Bioconcentration
Abiotic degradation

Resistant to photolysis, hydrolysis,
and OH radical-mediated reactions,
underenvironmentally
relevant
conditions. [1]Resistant to photolysis, hydrolysis, and OH
radical-mediatedreactions,
underenvironmentally relevant conditions [1]F-53B shows only very low degradation inadvanced oxidation processes [2]Biodegradation

Resistant to biodegradation [1]Not being removed in conventional
drinking water treatment plants [3]Resistant to biodegradation [1]F-53B is not readily biodegradable in closed
bottle tests [2]Adsorption on PACPFECAs have a lower affinity for
PAC than other PFASs of similar
chain length. About 35% removal of
HFPO-DA (CAS Number 62037-803) after 1h with 100 mg/L PAC. [3]Bioaccumulation
potential

Likely low bioaccumulation potential,with BCF (fish) <10 [4].
Log BAFfrogs, whole body (L/kg) = −0.12(HFPO-TA) [5]
t1/2 (rats) = 44 h (ADONA)

log BAFfrogs, whole body (L/kg) = ~3 (6:2 ClPFESA17) / ~4.2 (8:2 Cl-PFESA)
Black-spotted frogs sampled from several
Chinese cities, which have large-scale
fluorochemical industries [5]17Note on nomenclature: n:m here refers to the length of the carbon chain on each side of the ether bond. e.g.
6:2 means C6F13OC2F4–. Note that this commonly used nomenclature differs from the nomenclature of n:2
fluorotelomers.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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ENV/CBC/MONO(2022)1  43

t1/2 (humans) = 23 ± 11 d (ADONA)[1], [6]Environmental
transport

expected to have similar transport
properties as PFCAs [1]Synthesis
Main
synthesis
method(s)Some PFECAs are synthesized by an addition reaction of perfluoroalkyl fluorides withhexafluoropropylene oxide (HFPO), catalyzed by alkali-metal fluorides. Subsequenthydrolysis then yields the carboxylic acid.
Other synthesis routes, including electrochemical or direct fluorination may exist as well.
[7], [8]Rf = perfluorinated chain

Industrial Practices & Commercial Uses
Major Commercial Products
Trade name

GenX18Full name

Hexafluoropropylene oxide-dimer acid, ammonium salt

Other names

PFPrOPrA, HFPO-DA (acid form) [9]Composition

CF3CF2CF2OCF(CF3)COO− NH4+ [10]CAS Number

62037-80-3

Production/Import
volumes

Registered in 2011 under REACH with a production volume of 10–100 tonnes/yr in the
EU. [10]Use

Used as a processing aid in fluoropolymer production, replacing APFO. [11]Trade name

ADONA

Full name

3H-Perfluoro-3-[(3-methoxy-propoxy)propanoic acid], ammonium salt

Composition

CF3OC3F6OCHFCF2COO− NH4+ [6]CAS Number

958445-44-8

Production/Import
volumes

Registered under REACH with 1–10 tonnes/yr of production or import in the EU. [12]Use

As a processing aid, specifically as emulsifier, in fluoropolymer production. [6]Trade name

F-DIOX ammonium salt; cC6O4 ammonium salt

Full name

Perfluoro{acetic acid, 2-[(5-methoxy-1,3-dioxolan-4-yl)oxy]}, ammonium salt

Composition

C6F9O6− NH4+ [13]CAS Number

1190931-27-1

Production/Import

Registered under REACH with 1–10 tonnes/yr of production or import in the EU. [14]18Note that GenX has often been used interchangeably with hexafluoropropylene oxide dimer acid
(HFPO-DA) and HFPO-DA ammonium salt.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified44  ENV/CBC/MONO(2022)1
volumesUse

As a processing aid in fluoropolymer production. [13]Trade name

F-53B

Composition

ClF2C(CF2)5O(CF2)2SO3− K+ [2]

CAS Number

73606-19-6

Use

A mist suppressant in chrome plating, used as a substitute to PFOS [2]Uses
Major applications

A number of PFECAs (usually in the form of their ammonium salts) are used as
fluoropolymer processing aids, to replace APFO and APFN. [15] PFESAs like F-53B areused as PFOS substitutes, e.g. as mist suppressants in chrome plating [2].

Regulatory StatusUS

US EPA has released a draft reference dose of 80 ng/kg bw per day of HFPO-DA in 2018.
[16]

Europe

HFPO-DA has been added to the list of Substances of Very High Concern (SVHC) due
to its very high persistence, mobility, and potential harm to humans and the environment.
[4]

Examples of reported occurrences
Type oflocations/samples(Environmental) media

Detected in
one ormultipleregions

ExamplesLocation,year

Levels [min.–max. (detection
frequency)]

Note: Non-detects are reported as below the value of the limit of detection (“<LOD”).
pg = picograms, ng = nanograms, ww = wet weight, ND = not detected, NR = not reported
airone
Close toNetherlands HFPO-DA: 1.7–433 ng/L (13/13)
surfacewaterfluorochemical
multiple 2016
manufacturing
soil
park
sediment
US
HFPO-DA: 55–4560 ng/L (34/34)
2013
Not close to
specific point
sourcesair
surface watersoil
sedimentone
multiple

Ref.

[7]

[3]

Germany &Netherlands
2013

HFPO-DA: <0.11–86.1 ng/L
(4/23)

[17]

China
2014

HFPO-DA: <0.25–3060 ng/L
(22/29)

[17]

China
2013

F-53B: 11.7–54.7 ng/L (7/7)

[2]

China
2016

HFPO-DA: <0.05–1.54 ng/L
(33/35)[18]

HFPO-TA: <0.1–1.29 ng/L
(27/35)
4:2 Cl-PFESA: <0.01–0.04 ng/L
(4/35)
FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

ENV/CBC/MONO(2022)1  45

6:2 Cl-PFESA: 0.12–12.94 ng/L
(35/35)
8:2 Cl-PFESA: <0.01–0.29 ng/L
(18/35)
6:2 H-PFESA: 0.02–4.07 ng/L
(35/35)UK2016

HFPO-DA: 0.7–1.58 ng/L (6/6)[18]

HFPO-TA: <0.1–0.21 ng/L (4/6)
6:2 Cl-PFESA: 0.01–0.08 ng/L
(6/6)

Germany
2016

HFPO-DA: 0.59–1.98 ng/L
(20/20)[18]

HFPO-TA: <0.1–0.31 ng/L
(14/20)ADONA: <0.01–1.55 ng/L
(15/20)
6:2 Cl-PFESA: 0.02–0.38 ng/L
(20/20)US2016

HFPO-DA: 0.78–8.75 ng/L
(12/12)[18]

HFPO-TA: <0.1–4.33 ng/L (9/12)
6:2 Cl-PFESA: <0.01–0.08 ng/L
(8/12)
Drinking water
WWTP

effluent
influent
sludgeone
multiple

Netherlands
2016

HFPO-DA: <0.2–11 ng/L (3/6)

[7]

one

China
2013

F-53B: 79.9–108.7 ng/L (5/5)[2]

multipleeffluent
influent
sludgeBlack-spotted
frogs (P.
nigromaculatus,
liver)

Wildlife

F-53B: 45.7–74.8 ng/L (5/5)

onemultiple

China

HFPO-TA: <0.05–27.3 ng/g ww(4/56)[5]

6:2 Cl-PFESA: 0.13–119.05 ng/g
ww (56/56)
8:2 Cl-PFESA: 0.01–14.89 ng/g
ww (56/56)

Polar bear (liver)Greenland
2012–2013

F-53B: 0.27 ng/g (mean) (8/8)19

[19]

19

F-53B was also among a number of halogenated contaminants found in polar bears in Canada between 1984
and 2014 [20].
FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

46  ENV/CBC/MONO(2022)1
Knowledge gaps

- Main synthesis pathways for the commercial products of PFECAs and PFESAs.
- Global production volumes of commercial PFECAs and PFESAs.
- More information on the bioaccumulation potential needed.
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[15]
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W. A. Gebbink, L. Van Asseldonk, and S. P. J. Van Leeuwen, “Presence of Emerging Per- andPolyfluoroalkyl Substances (PFASs) in River and Drinking Water near a Fluorochemical Production
Plant in the Netherlands,” Environ. Sci. Technol., vol. 51, no. 19, pp. 11057–11065, 2017.
Z. Wang, I. T. Cousins, M. Scheringer, and K. Hungerbühler, “Fluorinated alternatives to long-chain
perfluoroalkyl carboxylic acids (PFCAs), perfluoroalkane sulfonic acids (PFSAs) and their potential
precursors,” Environ. Int., vol. 60, no. 2013, pp. 242–248, Oct. 2013.
Z. R. Hopkins, M. Sun, J. C. DeWitt, and D. R. U. Knappe, “Recently Detected Drinking Water
Contaminants: GenX and Other Per- and Polyfluoroalkyl Ether Acids,” J. Am. Water Works Assoc., vol.
110, no. 7, pp. 13–28, Jul. 2018.
Committee for Risk Assessment (RAC) and Committee for Socio-economic Analysis (SEAC),“Background document to the Opinion on the Annex XV dossier proposing restrictions on
Perfluorooctanoic acid (PFOA), PFOA salts and PFOA-related substances,” 2018.
“Scientific Opinion on the safety assessment of the substance, Perfluoro{acetic acid, 2-[(5-methoxy-1, 3dioxolan-4-yl)oxy]}, ammonium salt, CAS No 1190931-27-1, for use in food contact materials,” EFSA
J., vol. 12, no. 6, p. 3718, Jun. 2014.
ECHA, “Substance information Ammonium difluoro{[2,2,4,5-tetrafluoro-5-(trifluoromethoxy)-1,3dioxolan-4-yl]oxy}acetate,” 2019. [Online]. Available: https://echa.europa.eu/substance-information//substanceinfo/100.207.411. [Accessed: 04-Dec-2019].
R. C. Buck et al., “Perfluoroalkyl and polyfluoroalkyl substances in the environment: Terminology,
classification, and origins,” Integr. Environ. Assess. Manag., vol. 7, no. 4, pp. 513–541, Oct. 2011.
US EPA, “Technical Fact Sheet: Draft Toxicity Assessments for GenX Chemicals and PFBS,” 2018.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

ENV/CBC/MONO(2022)1  47

[17]
[18]
[19]

[20]

[Online].
Available:
https://www.epa.gov/sites/production/files/201812/documents/tech_fact_sheet_genx_pfbs_draft_tox_assess_final_508.pdf. [Accessed: 28-Apr-2021].
F. Heydebreck, J. Tang, Z. Xie, and R. Ebinghaus, “Alternative and Legacy Perfluoroalkyl Substances:
Differences between European and Chinese River/Estuary Systems,” 2015.
Y. Pan et al., “Worldwide Distribution of Novel Perfluoroether Carboxylic and Sulfonic Acids in Surface
Water,” Environ. Sci. Technol., vol. 52, no. 14, pp. 7621–7629, Jul. 2018.
W. Gebbink, R. Bossi, F. Riget, A. Rosing-Asvid, C. Sonne, and R. Dietz, “Observation of emerging perand polyfluoroalkyl substances (PFASs) in Greenland marine mammals,” Chemosphere., vol. 144, pp.
2384–2391, 2016.
Y. Liu et al., “Hundreds of Unrecognized Halogenated Contaminants Discovered in Polar Bear Serum,”Angew. Chem. Int. Ed., vol. 57, pp. 16401–16406, 2018.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

48  ENV/CBC/MONO(2022)1

5. Perfluoroalkanoyl fluorides (a) and their derivatives (b)20
Chemical Information & Properties
Identification and Terminology
Name

Perfluoroalkanoyl fluorides

Perfluoroalkyl fluoride derivatives

Acronym

PACFs

PACF-based derivatives

Chemical FormulaCn-1F2n-1COF

Cn-1F2n-1CONR2 (e.g. perfluoroalkyl
amides, PFAMs)21

General Structure(linear isomers)-1

US EPA CompTox
Markush ID
Examples ofIndividual
Acronyms (as usedin this document)

DTXSID10893647
MeFOA: n = 8, R1 = CH3, R2 = H
EtFOA: n = 8, R1 = CH2CH3, R2 = H
EtFBA: n = 4, R1 = CH2CH3, R2 = H

Degradability, Mobility, Bioconcentration
Degradation

Atmospheric lifetime

PACFs hydrolyze when released into theenvironment and form the corresponding
perfluoroalkyl carboxylic acids (PFCAs),
similarly to PASFs [1], [2]. These PFCAs
then are persistent in the environment; formore information, see the fact card #2 on
perfluoroalkyl carboxylic acids andperfluoroalkyl dicarboxylic acids.

MeFOA and EtFOA are expected tovolatilize to the atmosphere and react withhydroxyl radicals, ultimately forming
perfluorinated carboxylic acids (PFCAs)[2]. EtFBA is shown to degrade to PFBA,PFPrA, and TFA, among other products.
[3]

MeFOA: approx. 19 days (estimate)
EtFOA: approx. 2.7 days (estimate)
EtFBA: approx. 4.4 days (estimate)
Perfluorobutyramide (the primaryoxidation product of EtFBA): 7 times
EtFBA [3]Synthesis
Main Synthesis
MethodElectrochemical fluorination of an alkanoyl fluoride [1]𝐶𝑛 𝐻2𝑛+1 𝐶𝑂𝐹 + (2𝑛 + 1)𝐻𝐹 →𝐶𝑛 𝐹2𝑛+1 𝐶𝑂𝐹 + (2𝑛 + 1)𝐻2

20

For more examples of compounds in this group and their associated information, one may search for thefollowing IDs at the U.S. EPA CompTox Chemicals Dashboard website: https://comptox.epa.gov/dashboard,
namely DTXSID10893647, DTXSID70893648, DTXSID50893883, DTXSID10893884, DTXSID70893885,
DTXSID30893886, DTXSID90893887, DTXSID10893889, DTXSID20893890, DTXSID80896827
21
Note that PFCAs are also considered PACF-derivatives, but are discussed in their own fact card #2.
FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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ENV/CBC/MONO(2022)1  49

Reaction of these PACFs or of perfluoroalkanoyl chlorides with amines yields PFAMs:[2]
𝐶𝑛 𝐹2𝑛+1 𝐶𝑂𝐹 + 𝑁𝐻2 𝑅 →𝐶𝑛 𝐹2𝑛+1 𝐶𝑂𝑁𝐻𝑅 + 𝐻𝐹
PFAMs are also produced as by-products from POSF-based syntheses [2].
Possible Impurities

The electrochemical fluorination process is unselective and yields, besides the target
compound, a mixture of linear, branched, and cyclic homologues, which can be foundas impurities in the final product [1], [4].

Industrial Practices & Commercial Uses
Major Commercial Products
Full name

Perfluorobutanoyl fluoride (PBCF)

Composition

C3F7COFCAS Number

335-42-2

Production/Import
volumes

500 - <10,000t in the US in 2015 [11].

Use

Production of PFBA and potentially other, unknown uses [5].

Full name

Perfluorooctanoyl fluoride (POCF, sometimes also PFOF)

Composition

C7F15COF

CAS Number

335-66-0

Production/Import
volumes

0 lbs in the US in 2015 [11].

Use

Used to produce PFOA [1], [6].

Full nameN-(3-Trimethoxysilylpropyl)perfluorohexanamide

Composition

CF3(CF2)4CONH(CH2)3Si(OCH3)3

CAS Number

154380-34-4

Use

Surface treatment of glasses, natural stones, metals, wood, cellulose, cotton, leather,and ceramics [5].22

Uses
Major applications

PACFs are raw materials or intermediates in the production of the respective carboxylic
acids and derivatives thereof [5]. For example, POF is an intermediate in the productionof PFOA [1], [6].

Regulatory Status
General remarks

Since PACFs and their derivatives are precursors to PFCAs, most regulatory activities
are directed towards PFCAs, but include PACFs explicitly or implicitly.

US

Under the 2010/2015 PFOA Stewardship Program by the US EPA, eight major
multinational fluoropolymer and fluorotelomer PFCA manufacturers started to phase out
long-chain PFCAs in 2006, which was achieved by 2015. [4] In July 2020, the US EPA
issued a final rule requiring notice and US EPA review before manufacturing/processing
22

Note that these might be historical uses, as the manufacturer, Miteni, has declared bankruptcy since 2018[10].
FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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50  ENV/CBC/MONO(2022)1
of certain long-chain PFASs that have been phased out in the United States could
commence. [7]EuropePFOA and its ammonium salt (APFO), as well as some related substances, including
POF, have been classified as substances of very high concern (SVHCs) under REACH
in 2013. In 2017, these substances were also added to the restricted substances list. [4]International efforts
PFOA, its salts and PFOA-related compounds are listed as POPs (persistent organic pollutants) under Annex A(Elimination) to the Stockholm Convention with several specific exemptions (see listing for the chemical
definition of PFOA-related compounds covered) [8].
PFOA, its salts and PFOA-related compounds are recommended by the Chemical Review Committee (CRC) of
the Rotterdam Convention for listing under the Convention (to be determined by the Conference of the Parties(COP) in 2022). [9]Examples of reported occurrences
Note: As noted above, PACFs and their derivatives form the corresponding carboxylic acids when released tothe environment, similarly to PASFs. For examples of reported occurrences of the carboxylic acids in theenvironment, see the fact card #2 on PFCAs and PFdiCAs. No direct measurements of PACFs or their derivatives(other than PFCAs) in the environment have been found.
Knowledge gaps

- Information on recent uses and production volumes of PACFs is very limited.
- Information on PACF-based derivatives (such as PFAMs) is very limited and no environmental
monitoring studies of these compounds could be found.
References
[1]
[2]
[3]

[4]

[5]

[6]
[7]

[8]
[9]

R. C. Buck et al., “Perfluoroalkyl and polyfluoroalkyl substances in the environment: Terminology,
classification, and origins,” Integr. Environ. Assess. Manag., vol. 7, no. 4, pp. 513–541, Oct. 2011.
D. Jackson, and S. Mabury, “Polyfluorinated Amides as a Historical PFCA Source by Electrochemical
Fluorination of Alkyl Sulfonyl Fluorides,” Environ. Sci. Technol., vol. 47, no. 1, pp. 382–389, 2013.
D. Jackson, M. Wallington, and S. Mabury, “Atmospheric Oxidation of Polyfluorinated Amides:
Historical Source of Perfluorinated Carboxylic Acids to the Environment,” Environ. Sci. Technol., vol.
47, no. 9, pp. 4317–4324, 2013.
K. Sznajder-Katarzyńska, M. Surma, and I. Cieślik, “A Review of Perfluoroalkyl Acids (PFAAs) interms of Sources, Applications, Human Exposure, Dietary Intake, Toxicity, Legal Regulation, andMethods of Determination,” J. Chem., vol. 2019, 2019.
Z. Wang, I. T. Cousins, M. Scheringer, R. C. Buck, and K. Hungerbühler, “Global emission inventories
for C4–C14 perfluoroalkyl carboxylic acid (PFCA) homologues from 1951 to 2030, part II: The remaining
pieces of the puzzle,” Environ. Int., vol. 69, pp. 166–176, Aug. 2014.
C. Lassen et al., “Survey of PFOS, PFOA and other perfluoroalkyl and polyfluoroalkyl substances,”
2013.
U.S. EPA, “Risk Management for Per- and Polyfluoroalkyl Substances (PFAS) under TSCA,” available
at:https://www.epa.gov/assessing-and-managing-chemicals-under-tsca/risk-management-andpolyfluoroalkyl-substances-pfas.
Stockholm Convention on Persistent Organic Pollutants, “Report of the Conference of the Parties to the
Stockholm Convention on Persistent Organic Pollutants on the work of its ninth meeting,” Geneva, 2019.
Rotterdam Convention on the Prior Informed Consent Procedure for Certain Hazardous Chemicals andPesticides in International Trade, “Report of the Chemical Review Committee on the work of its sixteenth

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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ENV/CBC/MONO(2022)1  51

[10]
[11]

meeting,” Geneva, 2020. Decision CRC-16/2.
Eurofound,“ERM
factsheets:
Miteni,”
2018.
Availableat:https://www.eurofound.europa.eu/observatories/emcc/erm/factsheets/miteni.
U.S. EPA, Chemical Data Reporting (CDR), 2016. Available at https://www.epa.gov/chemical-datareporting/access-cdr-data.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified52  ENV/CBC/MONO(2022)1

6. Perfluoroalkanesulfonyl fluorides (a) and their derivatives (b) 23
Chemical Information & Properties
Identification and Terminology
Name

Perfluoroalkanesulfonyl fluorides

Perfluoroalkanesulfonyl fluoride derivatives

Acronym

PASFs

PASF-based derivatives

Chemical Formula

CnF2n+1SO2F

CnF2n+1SO2NR2 (example of a sulfonamide)DTXSID601024685(example of a sulfonamide)DTXSID501024694

General Structure(linear isomers)

US EPA CompTox
Markush ID
Examples ofIndividual
Acronyms (as usedin this document)

POSF: n = 8

FOSA: n = 8, R = H
MeFOSA: n = 8, R1 = CH3, R2 = H
MeFOSE: n = 8, R1 = CH3, R2 = CH2CH2OH
EtFOSA: n = 8, R1 = CH2CH3, R2 = H
EtFOSE: n = 8, R1 = CH2CH3, R2 =CH2CH2OH
MeFBSA: n = 4, R1 = CH3, R2 = H
MeFBSE: n = 4, R1 = CH3, R2 = CH2CH2OH
SAmPAP diester: N-ethyl perfluorooctane
sulfonamido ethanol-based phosphate diester

Degradability, Mobility, Bioconcentration
Degradation

PASFs rapidly hydrolyze to form thecorresponding sulfonic acids [1].
These sulfonic acids then are
persistent in the environment, formore information see the fact card #3
on perfluoroalkane sulfonic andsulfinic acids.

Biotic degradation of perfluorosulfonamides
mostly yields the corresponding sulfonicacids24, while abiotic degradation yields
sulfonic acids, carboxylic acids, and otherdegradation products [2] [3].
For example, EtFOSE is transformed in marine
sediments to N-ethyl perfluorooctane
sulfonamidoacetate, perfluorooctane

23

For more examples of compounds in this group and their associated information, one may search for thefollowing IDs at the U.S. EPA CompTox Chemicals Dashboard website: https://comptox.epa.gov/dashboard,
namely DTXSID50892977, DTXSID10892978, DTXSID80893634, DTXSID40893635, DTXSID70896775,
DTXSID30896832, DTXSID101010201, DTXSID801010202, DTXSID701010209, DTXSID701010211,
DTXSID101010213, DTXSID001010234, DTXSID701010235, DTXSID401010236, DTXSID101010237,
DTXSID801010238, DTXSID501010239, DTXSID801010240, DTXSID501010241, DTXSID201010242,
DTXSID901010243, DTXSID601010244, DTXSID201010254, DTXSID901010255, DTXSID601010256,
DTXSID301010257, DTXSID001010258, DTXSID701010259, DTXSID001010260, DTXSID701010261,
DTXSID401010262, DTXSID101010263
24
For more information on those compounds, see the fact card #3 on perfluoroalkane sulfonic and sulfinicacids.
FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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ENV/CBC/MONO(2022)1  53

sulfonamidoacetate, N-ethyl perfluorooctane
sulfonamide, perfluorooctane sulfonamide, andperfluorooctane sulfonate, with t1/2=44 d (25°C)
and 160 d (4°C). SAmPAP diester showed little
to no biotransformation over 120 d. [4]Adsorption on soil
& sediment

FOSA adsorbs strongly to organic matter,making soils an important environmental sink[5].

Bioaccumulation
potential

FOSA can be accumulated by various plants[5].

Synthesis
Main Synthesis
MethodMostly the Simons electrochemical fluorination process is used, where the hydrocarbon
sulfonyl fluoride is electrolyzed in anhydrous hydrogen fluoride [6]:𝐶𝑛 𝐻2𝑛+1 𝑆𝑂2 𝐹 + (2𝑛 + 1)𝐻𝐹 →𝐶𝑛 𝐹2𝑛+1 𝑆𝑂2𝐹 + (2𝑛 + 1)𝐻2
Reaction with an amine then yields sulfonamides:
𝐶𝑛 𝐹2𝑛+1 𝑆𝑂2 𝐹 + 𝑅𝑁𝐻2 →𝐶𝑛 𝐹2𝑛+1 𝑆𝑂2 𝑁𝐻𝑅 + 𝐻𝐹
These can be further reacted with, for example, ethylene carbonate, to give
perfluoroalkane sulfonamido ethanols. Possible subsequent reaction steps can yield Nalkyl perfluoroalkane sulfonamidoethyl acrylates and N-alkyl perfluoroalkane
sulfonamidoethyl methacrylates. [1]Possible Impurities

The electrochemical fluorination process is unselective and yields, besides the target
compound, a mixture of linear, branched, and cyclic homologues, which can be foundas impurities in the final products [1], [7].

Industrial Practices & Commercial Uses
Major Commercial Products
Full name

Perfluorooctane sulfonyl fluoride (POSF)

Composition

C8F17SO2FCAS Number

307-35-7

Production/Import
volumesGlobally: 96 000 tonnes (estimated) between 1970 and 2002; 410 tonnes between 2003
and 2008 [8]China: 250 tonnes (estimated) between 2003 and 2008 [8]Japan: 100 tonnes between 2003 and 2008 [8]Germany: 25 tonnes between 2003 and 2008 [8]Full name

Perfluorobutane sulfonyl fluoride (PBSF)

Composition

C4F9SO2FCAS Number

375-72-4

Production/Import
volumesGlobal production: in total, 317 tonnes in 2015 (299 tonnes in China). [9]Full nameSulfluramid / N-ethyl perfluorooctane sulfonamide

Composition

C8F17SO2NH(C2H5)FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified54  ENV/CBC/MONO(2022)1
CAS Number

4151-50-2

Production/Import
volumes

Production phased out in the US. [1], [10]Production in Brazil in 2013 was estimated to be about 60 tonnes. [10]Uses

Pesticide, especially used against leaf-cutter ants [1] [10]Full name

Sodium 2-(N-ethylperfluorooctane-1-sulfonamido)ethyl phosphate / perfluorooctane
sulfonamido ethanol-based phosphate diester / SAmPAP

Composition

F3C(F2C)7SO2N(C2H5)CH2CH2OPO(ONa)2

Production/Import
volumes

A high production volume chemical until 2002, then phased out in North America. [4]Uses

Used in food contact paper and packaging until it was phased out in North America
2002 [4]Other PASF
derivatives

PBSF-derivatives are used as surfactants (e.g. in coatings), as intermediates in the
manufacture of other chemicals, or as plastic additives. [9]Other PASF derivatives, such as N-MeFOSEA and N-EtFOSE, have been produced by
3M (which were phased out in 2002) and others [1]. They were used in surface treatment
products, as paper protectors, and as performance chemicals (e.g. fire extinguishingfoams and surfactants) [11].

Uses
Major applications

PASFs are used as starting material in the synthesis of sulfonamides and other derivatives
including side-chain fluorinated polymers, which have been and are used as plant growth
regulators, herbicides, in paper-protecting applications, and as surfactants and surface
protection products in other applications [1], [2], [6]. PASFs are precursors to PFSAs
with the same chain length [8].

Regulatory Status
US

In 2002, 3M - the then largest manufacturer of POSF phased out the production of POSFbased products, in agreement with the US EPA [7]. Certain PASFs are subject to a TSCA
significant new use rule [12]. US EPA cancelled the last remaining manufacturing-use
product registration for Sulfluramid in May 2008 and all remaining pesticide end-use
product registrations by 2013. [13]Some of these substances are precursors to PFOS, and they were assessed and managed
along with PFOS, its salts and precursors in 2006. They are prohibited with a limited
number of exemptions under the Prohibition of Certain Toxic Substances Regulations,2012 [14], [15]PFOS and its derivatives (including POSF and FOSA) are regulated as persistent organic
pollutants (POPs) and their production, sale, and use in the EU is prohibited, with certain
exemptions [8]. PFBS, PFHxS and their salts are listed as SVHC under REACH [16].

CanadaEuropeInternational efforts
POSF25 was added to Annex B to the Stockholm Convention as POP in 2009, together with PFOS and its salts.
[19] The acceptable pursposes and specific exemptions were amended in 2019. [20]
POSF was added to Annex III to the Rotterdam Convention in 2013, together with PFOS, perfluorooctane
sulfonates, perfluorooctane sulfonamides. [21]25

In the Stockholm Convention and the Rotterdam Convention the acronym PFOSF is used.
FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)

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ENV/CBC/MONO(2022)1  55

Examples of reported occurrences
Type oflocations/samples(Environmental)
media

Detected in
one ormultipleregions

ExamplesLocation,year

Levels [min. –max. (detection
frequency; substance)]

Ref.

Note: As noted above, PASFs and their derivatives transform in the environment, forming PFSAs and PFCAs(not in the case of PASFs). For examples of reported occurrences of those, see the fact cards #2 on
perfluoroalkyl carboxylic and dicarboxylic acids and #3 on perfluoroalkane sulfonic and sulfinic acids.
Non-detects are reported as below the value of the limit of detection (“<LOD”).
pg = picograms, ng = nanograms, ND = not detected, NR = not reported
airone
Close toCanadaMeFOSA: 6.11–48.2 pg/m3
surface water
WWTP and(16/16)
multiple 2009
landfills
soil
EtFOSA: 6.07–30 pg/m3 (16/16)
sediment
MeFOSE: 1.06–41.5 pg/m3(16/16)[17]

EtFOSE: <4.8–29.2 pg/m3(16/16)
Not close to
specific point
sourcesair
surface watersoil
sedimentone
multiple

Germany
2007

FOSA: 0.1–1.0 ng/L (15/15)[18]

WWTP andon-site septic
systems

effluent
influent
sludgeone

Germany
2007

FOSA: 0.3–1.1 ng/L (9/9)[18]

multiple

MeFBSA: <0.17–14 ng/L (3/9)
MeFBSE: <0.07–0.5 ng/L (3/9)

Wildlife

effluent
sludgeone
multiple

UnitedStates 2012
& 2013PFOSA: ND-6.56 ng/L (12/28)[22]

Peregrine falcons,
serum

one
multiple

Canada,2018

FOSA: ND–0.12 ng/g ww (5/29)
MeFOSA: ND–0.05 ng/g ww(3/29)
EtFOSA: ND–0.02 ng/g ww(1/29)[23]

Peregrine falcons,egg

one
multiple

Canada,2018

FOSA: ND (0/9)
MeFOSA: ND (0/9)
EtFOSA: ND–0.01 ng/g ww (1/9)

Knowledge gaps

- Current commercial products of PASF-derivatives, especially their production and uses (including
volumes), are largely unknown.
References[1]

R. C. Buck et al., “Perfluoroalkyl and polyfluoroalkyl substances in the environment: Terminology,
classification, and origins,” Integr. Environ. Assess. Manag., vol. 7, no. 4, pp. 513–541, Oct. 2011.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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56  ENV/CBC/MONO(2022)1
[2]

[3]

[4]

[5]

[6]
[7]

[8]
[9]
[10]

[11]

[12]

[13]
[14]

[15]
[16]
[17]

[18]

[19]

[20]

T. Frömel and T. P. Knepper, “Biodegradation of Fluorinated Alkyl Substances,” in Reviews ofEnvironmental Contamination and Toxicology, vol. 208, P. De Voogt, Ed. New York, NY: Springer New
York, 2010, pp. 161–177.
J. Martin, B. Asher, S. Beesoon, J. Benskin and M. Ross, “PFOS or PreFOS? Are perfluorooctane
sulfonate precursors (PreFOS) important determinants of human and environmental perfluorooctane
sulfonate (PFOS) exposure?,” in J. Environ. Monit., vol. 12, no. 11, pp. 1979–2004, 2010.
J. Benskin, M. Ikonomou, F. Gobas, T. Begley, M. Woudneh, and J. Cosgrove, “Biodegradation of N Ethyl Perfluorooctane Sulfonamido Ethanol (EtFOSE) and EtFOSE-Based Phosphate Diester (SAmPAP
Diester) in Marine Sediments,” Environ. Sci. Technol., vol. 47, no. 3, pp. 1381–1389, 2013.
S. Zhao et al., “Biotransformation and responses of antioxidant enzymes in hydroponically cultured
soybean and pumpkin exposed to perfluorooctane sulfonamide (FOSA),” Ecotoxicol. Environ. Saf., vol.
161, pp. 669–675, Oct. 2018.
G. Siegemund et al., “Fluorine Compounds, Organic,” Ullmann’s Encycl. Ind. Chem., pp. 1–56, 2016.
K. Sznajder-Katarzyńska, M. Surma, and I. Cieślik, “A Review of Perfluoroalkyl Acids (PFAAs) in termsof Sources, Applications, Human Exposure, Dietary Intake, Toxicity, Legal Regulation, and Methods ofDetermination,” J. Chem., vol. 2019, 2019.
C. Lassen et al., “Survey of PFOS, PFOA and other perfluoroalkyl and polyfluoroalkyl substances,” 2013.
C. Lassen, A. Brinch, and A. Jensen, “Investigation of Sources to PFBS in the Environment,” Norwegian
Environment Agency, 2017.
J. Löfstedt Gilljam, J. Leonel, I. Cousins, and J. Benskin, “Is Ongoing Sulfluramid Use in South Americaa Significant Source of Perfluorooctanesulfonate (PFOS)? Production Inventories, Environmental Fate,and Local Occurrence,” Environ. Sci. Technol., vol. 50, no. 2, pp. 653–659, 2016.
3M Company, “Fluorochemical use, distribution and release overview. USEPA Administrative Record
AR226-0550,” 1999 [Online]. Available: www.regulations.gov as document EPA-HQ-OPPT-20020051-000. [Accessed: 24-Jul-2020].
USA, “40 CFR §721.9582. Certain perfluoroalkyl sulfonates,” Avaible at: https://www.ecfr.gov/cgibin/textidx?SID=c8175aed22d0b9446beca21293ba915f&mc=true&node=se40.33.721_19582&rgn=div8
Environmental Protection Agency, “Product Cancellation Order for Certain Pesticide Registrations,” Fed.
Reg., vol. 78, no. 79, pp. 24197–24199, 2013.
Environment Canada, “Screening assessment: Perfluorooctane sulfonic acid, its salts and its precursors,”
Environment Canada, Existing Substances Division, Gatineau (QC), 2006. Available at:https://www.canada.ca/en/environment-climate-change/services/canadian-environmental-protectionact-registry/publications/ecological-screening-report-sulfonate.html.
Canada, “Prohibition of Certain Toxic Substances Regulations, SOR/2012-285,” 2016. Available at:https://laws-lois.justice.gc.ca/eng/regulations/SOR-2012-285/index.html
European Chemicals Agency, “Agreement of the Member State Committee on the Identification of
Perfluorobutane sulfonic acid and its salts as Substances of Very High Concern,” 2019.
L. Ahrens, M. Shoeib, T. Harner, S. C. Lee, R. Guo, and E. J. Reiner, “Wastewater treatment plant andlandfills as sources of polyfluoroalkyl compounds to the atmosphere,” Environ. Sci. Technol., vol. 45, no.
19, pp. 8098–8105, 2011.
L. Ahrens, S. Felizeter, R. Sturm, Z. Xie, and R. Ebinghaus, “Polyfluorinated compounds in waste water
treatment plant effluents and surface waters along the River Elbe, Germany,” Mar. Pollut. Bull., vol. 58,
no. 9, pp. 1326–1333, 2009.
Stockholm Convention on Persistent Organic Pollutants, “Report of the Conference of the Parties to the
Stockholm Convention on Persistent Organic Pollutants on the work of its fourth meeting,” Geneva,2009.
Decision SC-4/17.
Stockholm Convention on Persistent Organic Pollutants, “Report of the Conference of the Parties to the
Stockholm Convention on Persistent Organic Pollutants on the work of its ninth meeting,” Geneva, 2019.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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ENV/CBC/MONO(2022)1  57

[21]

[22]

[23]

Decision SC-9/4.
Rotterdam Convention on the Prior Informed Consent Procedure for Certain Hazardous Chemicals andPesticides in International Trade, “Report of the Conference of the Parties to the Rotterdam Convention
on the Prior Informed Consent Procedure for Certain Hazardous Chemicals and Pesticides in International
Trade on the work of its sixth meeting,” Geneva, 2013. Decision RC-6/7.
B. Subedi et al., “A pilot study on the assessment of trace organic contaminants including pharmaceuticals
and personal care products from on-site wastewater treatment systems along Skaneateles Lake in New
York State, USA,” Water Research, vol. 72, no. 19, pp. 28–39, 2015.
J. Sun, R. J. Letcher, M. Eens, A. Covaci, and K. J. Fernie, “Perfluoroalkyl acids and sulfonamides anddietary, biological and ecological associations in peregrine falcons from the Laurentian Great Lakes
Basin, Canada,” Env. Res., vol. 191, pp. 110151, 2020.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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58  ENV/CBC/MONO(2022)1

7. n:2 Fluorotelomer-based compounds
Key publications: J. W. Washington, T. M. Jenkins, K. Rankin, and J. E. Naile. 2015.
Decades-Scale Degradation of Commercial, Side-Chain, Fluorotelomer-Based Polymers inSoils and Water. Environ. Sci. Technol., 49(2): 915–923.
Buck, Robert C, James Franklin, Urs Berger, Jason M Conder, Ian T Cousins, Pim de
Voogt, Allan Astrup Jensen, Kurunthachalam Kannan, Scott A Mabury, and Stefan PJ van
Leeuwen. 2011. “Perfluoroalkyl and Polyfluoroalkyl Substances in the Environment:
Terminology, Classification, and Origins.” Integrated Environmental Assessment andManagement 7 (4): 513–41.

Chemical Information & Properties
Identification and Terminology
Namen:2 Fluorotelomers

n:2 Fluorotelomer olefins

Acronymn:2 FT[R], e.g. FTOH

n:2 FTO

Chemical Formula

CnF2n+1C2H4R

CnF2n+1C2HR1R2

General Structure(linear isomers)

R1 and R2 = H, unless for carboxylic acids
US EPA CompTox
Markush IDDTXSID401024691

DTXSID601024928

Terminology

n:m FT[R], where n = number of perfluorinated carbons and m = number of nonfluorinated carbons.

Overview of n:2 Fluorotelomer derivatives [1]26

26

For more examples of compounds in this group and their associated information, one may search for thefollowing IDs at the US EPA CompTox Chemicals Dashboard website: https://comptox.epa.gov/dashboard,
namely DTXSID50892558 (FTSAs), DTXSID90893802 (FTOHs), DTXSID50892972, DTXSID70892974,
DTXSID30892975, DTXSID90892976, DTXSID40893817, DTXSID70893820, DTXSID80893876,
DTXSID60893879, DTXSID301010245, DTXSID801010264, DTXSID501010265. In addition, fluorinatedacrylate and urethane polymers belong to so-called “side-chain fluorinated polymers” (polymers with
nonfluorinated polymer backbones and fluorinated side chains).
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Acronyms: FTI = fluorotelomer iodide; FTO = fluorotelomer olefin; FTSA = fluorotelomer sulfonic acid; FTOH = fluorotelomer alcohol; sFTOH= fluorotelomer secondary alcohol; FTAB = fluorotelomer sulfonamide alkylbetaine; FTEO = fluorotelomer ethoxylate; monoPAP = fluorotelomer
monophosphate; diPAP = fluorotelomer diphosphate; FTS = fluorotelomer alkyl stearate; FT(M)AC = fluorotelomer (meth)acrylate; FTUCA =unsaturated fluorotelomer carboxylic acid27

Degradability, Mobility, Bioconcentration
General remarks
and degradation
products

Degradation pathways of n:2 fluorotelomer-based chemicals depend on theenvironmental matrices and can be very complex [2], [3]. Generally, though, the alcohols
are transformed to aldehydes, which are further oxidized to form the corresponding
carboxylic acids. These can then be further transformed to a range of saturated andunsaturated compounds, including PFCAs [3]. For more detailed information on the
degradation of fluorotelomer-based compounds, see Buck et al. 2011 and Frömel &Knepper 2010.

Atmosphericdegradation

Reaction of n:2 FTOHs with OH radicals in the atmosphere (or surface waters) yields
PFCAs [4].

(Bio)degradation insoil and sediment

8:2 FTOH degraded rapidly (<7 d) in aerobic soil and yielded (on average) 25% PFOA,
and 11% 7:3 FTCA, both of which did not degrade further [5].
6:2 FTOH degraded rapidly (t1/2 <2 d) in aerobic soil and formed 30% PFPeA, 15% 5:3
FTCA, and 8% PFHxA after 180 days. [6]6:2 FTSA was rapidly (t1/2 <5 d) transformed in aerobic river sediment to form PFPeA(21%mol), PFHxA (20%mol), and 5:3 FTCA (16%mol) after 90 days. No degradation at all
was observed in anaerobic sediment after 100 days. [7]Fluorotelomer-based side-chain fluorinated polymers degrade in saturated soil and water
to form FTOHs and PFCAs, among other PFAS species. Hydrolysis occurs slowly under
neutral conditions (t1/2 = 55–89 yrs), but much faster at higher pH values (t1/2 at pH 10 =4.9 yrs, t1/2 at pH 12 = 0.7 yrs). [8], [9]Biodegradation inbacterial culture

6:2 FTOH degraded rapidly (t1/2 <2 days) in mixed bacterial culture to form 23% FTUA,
16% 5:2 sFTOH (secondary alcohol, [F(CF2)5CH(OH)CH3]), 6% 5:3 FTCA, and 5%
PFHxA after 90 days. [6]In activated sludge from WWTPs, 6:2 FTOH was found to be transformed mainly to 5:2

27

Note that often a different nomenclature is used for FTUCAs in literature. According to this nomenclature,
6:2 FTUCA is referred to as FHUEA, 8:2 FTUCA as FOUEA, and so forth. This fact card will keep the generaln:2 fluorotelomer nomenclature though.
FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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60  ENV/CBC/MONO(2022)1
sFTOH (40%mol) after 2 months [10].
Metabolism inmammals

FTOHs are mostly rapidly eliminated in urine as conjugates, although PFCAs have also
been detected as transformation products [3]. In rats, 8:2 FTOH has been found to be
excreted mainly via feces, with metabolites including 7:2 sFTOH, 7:2 Ketone, and PFOA,
among others [11]. 6:2 FTOH is reported to be rapidly metabolized and eliminated inhumans, although its main metabolites PFHxA, PFHpA, PFBA, and 5:3 Acid can exhibit
elimination half-lives of 1–2 months after a period of high exposure [12].

Mobility

FTOHs generally exhibit high volatilities and poor water solubilities, resulting in highwater-air partition coefficients and high tendency for sorption onto particles when
dissolved in water. [2]Synthesis
Main Synthesis
MethodTelomerization: A perfluoroalkyl iodide (usually perfluoroethyl iodide) is reacted withtetrafluoroethylene to increase the perfluorinated chain length. Subsequently, ethylene isinserted (using catalysts or increased temperature and pressure) to form perfluoroalkyl
ethyl iodides [3]𝐹(𝐶𝐹2 )𝑛 𝐼 + 𝐶𝐻2 = 𝐶𝐻2 →𝐹(𝐶𝐹2 )𝑛 𝐶𝐻2𝐶𝐻2 𝐼

Possible Impurities

The telomerization process yields only homologues. Whether they are linear (common)or branched (uncommon) isomers, depends on the starting perfluoroalkyl iodide [3].

Industrial Practices & Commercial Uses
Major Commercial Products28
Full name

6:2 Fluorotelomer sulfonamide betaine

Composition

F(CF2)6(CH2)2SO2NH(CH2)3NH2+CH2COOH

CAS Number

34455-29-3

Production/Import
volumes

Registered in the EU under REACH with a production/import volume of 100–1000 t/yr.
[13]

Use

Used in fire-fighting foams, professional cleaning products, and inks and films. [13]Full name

Triethoxy(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane

Composition

F(CF2)6(CH2)2Si(OCH2CH3)3

CAS Number

51851-37-7

Production/Import
volumes

Registered in the EU under REACH with a production/import volume of 10–100 t/yr.
[14]

Use

Used as oil/water repellence for carpets, fabric/upholstery, apparel, leather and glass. [14]Full name

3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctanesulfonic acid

Other names

6:2 Fluorotelomer sulfonic acid

Composition

F(CF2)6(CH2)2SO3H

CAS Number

27619-97-2

Production/Import
volumes

Registered in the EU under REACH with a production/import volume of 10–100 t/yr.
[15]

28

Note that these are just some examples of fluorotelomer-based products, not including polymers. For a morecomprehensive overview see the overview figure above.
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ENV/CBC/MONO(2022)1  61

Use

Used as a mist suppressant in metal plating [15]Uses
Major applications

Raw material intermediates such as n:2 FTOHs are used to produce surfactants andsurface protectors, including side-chain fluorinated polymers. n:2 FTSAs are also directly
used as surfactants. diPAPs have also been used as grease-proofing agents for foodcontact paper, as defoaming adjuvants in pesticide formulations and as surfactants inindustrial cleaning products [3]. For more details on the applications of side-chain
fluorinated polymers, see Buck et al. (2011).

Regulatory Status
US

Some of these substances are regulated under 40 CFR §721.10536, the long-chain
perfluoroalkyl carboxylate chemical substances significant new use rule. [16]A final rule to revoke tolerance exemptions for mono- and bis-(1H,1H,2H,2Hperfluoroalkyl) phosphates where the alkyl group is even numbered and in the C6-C12
range was published in August 2006 with an effective date 18 months after the publicationof the final rule. [17]Under the 2010/2015 PFOA Stewardship Program by the US EPA, eight major multinational fluoropolymer and fluorotelomer PFCA manufacturers started to phase out longchain PFCAs and related chemicals in 2006, which was achieved by 2015. [26]CanadaCertain fluorotelomers (including diPAPs) are precursors to PFOA and long-chain (C9–C20) PFCAs. Non-exhaustive lists of precursors to PFOA and long-chain (C9–C20) PFCAs
can be found in the ecological screening assessments for PFOA and long-chain (C9–C20)
PFCAs [18], [19].
These substances are prohibited with a limited number of exemptions under theProhibition of Certain Toxic Substances Regulations, 2012 [20].

Europe(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) silanetriol and any of its mono-, di- or tri-O(alkyl) derivatives (TDFAs) have been added to the restricted substances list (REACH
Annex XVII) in 2021. [27]International efforts
Some long-chain fluorotelomers (n≥8 and n≤16) are considered PFOA-related compounds under the Stockholm
Convention on Persistent Organic Pollutants. [28]Examples of reported occurrences
Type oflocations/samples(Environmental)
media

Detected in
one ormultipleregions

ExamplesLocation,year

Levels [min.–max. (detection
frequency)]

Ref.

Non-detects are reported as below the value of the limit of detection (“<LOD”).
pg = picograms, ng = nanograms, ND = not detected, NR = not reported
airone
Close toCanada
6:2 FTOH: 0.09–12.3 ng/m3
surface water
WWTP and(16/16)
multiple 2009
landfills
soil
8:2 FTOH: 0.14–17.4 ng/m3
sediment(16/16)[10]

10:2 FTOH: 0.07–2.15 ng/m3(16/16)
Landfill leachate

US

4:2 FTUCA: ND–6.3 ng/L (1/87)[23]

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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2013–2014

6:2 FTUCA: <2.0–52.0 ng/L
(45/87)
8:2 FTUCA: <2.0–161 ng/L
(24/87)
10:2 FTUCA: ND–49.3 ng/L
(9/87)
4:2 FTSA: <5.0–22.7 ng/L (22/87)
6:2 FTSA: <2–2247.8 ng/L
(84/87)
8:2 FTSA: <2–667.0 ng/L (64/87)
6:2 diPAP: <1.9–26.4 ng/L
(14/87)
8:2 diPAP: <2.0–208.8 ng/L
(12/87)
10:2 diPAP: ND–47.7 ng/L (6/87)

Not close to
specific point
sourcesair
surface watersoil
sedimentone
multiple

Germany
2007

6:2 FTSA: <0.2–1.1 ng/L (8/15)[21]

8:2 FTUCA: <0.01–0.1 ng/L
(1/15)
10:2 FTUCA: <0.03–0.3 ng/L
(3/15)

Japan
2007–2008

8:2 FTOH: <0.2–3.38 ng/L
(19/33)[22]

10:2 FTOH: <0.2–4.06 ng/L
(4/33)
8:2 FTAc: <0.05–0.16 ng/L
(6/33)
WWTP

Indoorenvironment

one

effluent
influent
sludgeIndoor air, hotels

6:2 FTOH: <0.2–37.9 ng/L (5/9)

multiple

Germany
2007

one
multiple

China
2015

6:2 FTOH: <0.026–1.9 ng/m3(16/19)[21]

6:2 FTUCA: <0.07–0.9 ng/L (1/9)[24]

8:2 FTOH: 0.253–48.0 ng/m3(19/19)10:2 FTOH: 0.054–13.6 ng/m3(19/19)
6:2 diPAP: <0.001–0.0067 ng/m3(10/19)
8:2 diPAP: <0.002–0.0177 ng/m3(6/19)
6:2 FTUCA: <0.002–0.0084
ng/m3

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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ENV/CBC/MONO(2022)1  63

(13/19)
8:2 FTUCA: <0.001–0.005 ng/m3(13/19)Indoor dust, hotels

China
2015

6:2 FTOH: 4.71–372 ng/g (11/11)[24]

8:2 FTOH: 15.6–438 ng/g (11/11)
10:2 FTOH: 3.96–123 ng/g
(11/11)
6:2 diPAP: 1.08–67.4 ng/g (11/11)
8:2 diPAP: <0.06–115 ng/g
(10/11)
6:2 FTUCA: <0.06–0.75 ng/g
(6/11)
8:2 FTUCA: 0.11–8.29 ng/g
(11/11)

Indoor dust,
residential

Germany
2008–2009

6:2 FTOH: <1.6–246 ng/g
(24/31)[25]

8:2 FTOH: 2.4–256 ng/g (31/31)
10:2 FTOH: 1.0–232 ng/g (31/31)
Knowledge gaps

- Current global production and use volumes are unknown.
References
[1]

[2]

[3]
[4]
[5]

[6]
[7]
[8]

[9]

Z. Wang, I. T. Cousins, M. Scheringer, R. C. Buck, and K. Hungerbühler, “Global emission inventories
for C4–C14 perfluoroalkyl carboxylic acid (PFCA) homologues from 1951 to 2030, Part I: production andemissions from quantifiable sources,” Environ. Int., vol. 70, pp. 62–75, Sep. 2014.
T. Frömel and T. P. Knepper, “Biodegradation of Fluorinated Alkyl Substances,” in Reviews ofEnvironmental Contamination and Toxicology, vol. 208, P. De Voogt, Ed. New York, NY: Springer New
York, 2010, pp. 161–177.
R. C. Buck et al., “Perfluoroalkyl and polyfluoroalkyl substances in the environment: Terminology,
classification, and origins,” Integr. Environ. Assess. Manag., vol. 7, no. 4, pp. 513–541, Oct. 2011.
J. R. Parsons, M. Sáez, J. Dolfing, and P. de Voogt, “Biodegradation of Perfluorinated Compounds,” inReviews of Environmental Contamination and Toxicology, vol. 196, 2008, pp. 53–71.
N. Wang, B. Szostek, R. C. Buck, P. W. Folsom, L. M. Sulecki, and J. T. Gannon, “8-2 Fluorotelomer
alcohol aerobic soil biodegradation: Pathways, metabolites, and metabolite yields,” Chemosphere, vol.
75, no. 8, pp. 1089–1096, May 2009.
J. Liu et al., “6-2 Fluorotelomer alcohol aerobic biodegradation in soil and mixed bacterial culture,”
Chemosphere, vol. 78, no. 4, pp. 437–444, Jan. 2010.
S. Zhang, X. Lu, N. Wang, and R. C. Buck, “Biotransformation potential of 6:2 fluorotelomer sulfonate(6:2 FTSA) in aerobic and anaerobic sediment,” Chemosphere, vol. 154, pp. 224–230, Jul. 2016.
J. W. Washington, T. M. Jenkins, K. Rankin, and J. E. Naile, “Decades-Scale Degradation of Commercial,
Side-Chain, Fluorotelomer-Based Polymers in Soils and Water,” Environ. Sci. Technol., vol. 49, no. 2,
pp. 915–923, Jan. 2015.
J. W. Washington and T. M. Jenkins, “Abiotic Hydrolysis of Fluorotelomer-Based Polymers as a Source

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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[10]
[11]

[12]
[13]

[14]

[15]

[16]

[17]

of Perfluorocarboxylates at the Global Scale,” Environ. Sci. Technol., vol. 49, no. 24, pp. 14129–14135,
Dec. 2015.
L. Zhao et al., “6:2 Fluorotelomer alcohol aerobic biotransformation in activated sludge from twodomestic wastewater treatment plants,” Chemosphere, vol. 92, no. 4, pp. 464–470, Jul. 2013.
W. J. Fasano et al., “Kinetics of 8-2 fluorotelomer alcohol and its metabolites, and liver glutathione status
following daily oral dosing for 45 days in male and female rats,” Chemico-Biological Interactions, vol.
180, no. 2, pp. 281-295, 2009.
M.H. Russell, M. W. Himmelstein, R. C. Buck, “Inhalation and oral toxicokinetics of 6:2 FTOH and its
metabolites in mammals,” Chemosphere, vol. 120, pp. 328-335, 2015.
European Chemicals Agency (ECHA), “Carboxymethyldimethyl-3-[[(3,3,4,4,5,5,6,6,7,7,...-Registration
Dossier” [Online]. Available: https://echa.europa.eu/registration-dossier/-/registered-dossier/17549.
[Accessed: 10-Dec-2019].
European Chemicals Agency (ECHA), “Triethoxy(3,3,4,4,5,5,6,6,7,7,...-Registration Dossier” [Online].
Availableat:https://echa.europa.eu/registration-dossier/-/registered-dossier/24656/3/1/4[Accessed: 21-Dec-2020].
European Chemicals Agency (ECHA), “3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctanesu... - Registration
Dossier” [Online]. Available: https://echa.europa.eu/registration-dossier/-/registered-dossier/24637.
[Accessed: 10-Dec-2019].
USA, “40 CFR §721.10536 Long-chain perfluoroalkyl carboxylate chemical substances”, Available at:https://www.ecfr.gov/cgi-bin/textidx?SID=c8175aed22d0b9446beca21293ba915f&mc=true&node=se40.33.721_110536&rgn=div8.
Environmental Protection Agency, “Inert ingredient; Revocation of the tolerance exemption for monoand bis-(1H, 1H, 2H, 2H-perfluoroalkyl) phosphates where the alkyl group is even numbered and in the
C6-C12 range,” Fed. Reg., vol. 71, no. 153, pp. 45408–45411, Aug. 2006.

[18]

Environment Canada. 2012. Screening assessment: Long-Chain (C9–C20) Perfluorocarboxylic Acids,
their Salts and their Precursors Gatineau (QC): Environment Canada, Existing Substances Division.
Available at: http://ec.gc.ca/ese-ees/default.asp?lang=En&n=CA29B043-1.

[19]

Environment Canada. 2012. Screening assessment: Perfluorooctanoic acid, its salts and its precursors.
Gatineau (QC): Environment Canada, Existing Substances Division. Available at: http://ec.gc.ca/eseees/default.asp?lang=En&n=370AB133-1.
Canada. 2016. Prohibition of Certain Toxic Substances Regulations, SOR/2012-285. Available at:https://laws-lois.justice.gc.ca/eng/regulations/SOR-2012-285/index.html.
L. Ahrens, S. Felizeter, R. Sturm, Z. Xie, and R. Ebinghaus, “Polyfluorinated compounds in waste water
treatment plant effluents and surface waters along the River Elbe, Germany,” Mar. Pollut. Bull., vol. 58,
no. 9, pp. 1326–1333, 2009.
M. A. M. Mahmoud, A. Kärrman, S. Oono, K. H. Harada, and A. Koizumi, “Polyfluorinated telomers inprecipitation and surface water in an urban area of Japan,” Chemosphere, vol. 74, no. 3, pp. 467–472,
Jan. 2009.
J. R. Lang, B. M. Allred, J. A. Field, J. W. Levis, and M. A. Barlaz, “National Estimate of Per- andPolyfluoroalkyl Substance (PFAS) Release to U.S. Municipal Landfill Leachate,” Environ. Sci. Technol.,vol. 51, no. 4, pp. 2197–2205, Feb. 2017.
Y. Yao et al., “Per- and Polyfluoroalkyl Substances (PFASs) in Indoor Air and Dust from Homes andVarious Microenvironments in China: Implications for Human Exposure,” Environ. Sci. Technol., vol.
52, no. 5, pp. 3156–3166, 2018.
Z. Xu et al., “Human exposure to fluorotelomer alcohols, perfluorooctane sulfonate andperfluorooctanoate via house dust in Bavaria, Germany,” Sci. Total Environ., vol. 443, pp. 485–490,
2013.
U.S. EPA, “Risk Management for Per- and Polyfluoroalkyl Substances (PFAS) under TSCA,” available
at:https://www.epa.gov/assessing-and-managing-chemicals-under-tsca/risk-management-and-

[20]
[21]

[22]

[23]

[24]

[25]

[26]

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[27]

[28]

polyfluoroalkyl-substances-pfas.
European Chemicals Agency (ECHA), “Annex XVII to REACH – Conditions of restriction. Entry 73”[Online].
Availableat:https://echa.europa.eu/documents/10162/57497ef0-ee60-a9e9-8bd19daba3b3c427 [Accessed: 26-May-2021].
Stockholm Convention on Persistent Organic Pollutants, “Report of the Conference of the Parties to the
Stockholm Convention on Persistent Organic Pollutants on the work of its ninth meeting,”
Geneva,2019. Decision SC-9/12.

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8. n:1 Fluorotelomer-based compounds
Chemical Information & Properties
Identification and Terminology
Namen:1 Fluorotelomers29

Acronymn:1 FT[R], e.g., n:1 FTOH30

Chemical Formula

CnF2n+1CH2OH

General Structure(linear isomers)

R = e.g. OH, NH2, I
US EPA CompTox
Markush ID
Terminology

DTXSID901024684
n:m FT[R], where n = number of perfluorinated carbons and m = number of nonfluorinated carbons

Degradability, Mobility, Bioconcentration
Degradation

n:1 FTOHs can react with OH radicals in the environment to form corresponding
aldehydes and subsequently carboxylic acids [1].

Reaction with OH
radicals

3:1 FTOH: 1.0–1.1 × 10−13 k(OH+R)/cm3 molecule−1 s−1Note: The reaction rate constant is likely largely independent of the chain length, andtherefore, valid also for other n:1 FTOHs [1].

Synthesis
Main Synthesis
Methodn:1 Fluorotelomer compounds are NOT produced via the telomerization process. Instead,they are synthesized through catalytic reduction (hydrogenation) of the corresponding
perfluoroalkyl carboxylic acids [1], [2]. For example, LiAlH4 can be used to produce n:1
FTOHs [3]:𝐿𝑖𝐴𝑙𝐻4

𝐹(𝐶𝐹2 )𝑛 𝐶𝑂𝑂𝐻 →Possible Impurities

𝐹(𝐶𝐹2 )𝑛 𝐶𝐻2 𝑂𝐻

Unreacted PFCAs may remain as impurities in n:1 fluorotelomer derivative products.
Additionally, the PFCAs themselves, which are used as starting material, are likely tocontain both branched and linear isomers, due to them being produced via the ECF
process. [1]Industrial Practices & Commercial Uses
Major Commercial Products

29

As known commercial n:1 fluorotelomer-based compounds are not derived from the telomerization process,but rather from the reduction of perfluoroalkyl carboxylic acids, they are not, strictly speaking, fluorotelomers.
Despite this, they are termed “n:1 FT-based compounds” here for readability, since the pattern of theperfluorocarbon:hydrocarbon chain is the same (i.e., n:1 vs. n:2). Future work may consider to identify more
proper terminology for this group of PFASs.
30
While other n:1 fluorotelomers (such as n:1 fluorotelomer amins or iodides) exist [4], no information onthem could be found.
FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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ENV/CBC/MONO(2022)1  67

Trade Name

RM 610

Full Name(Perfluoropropyl)methanol (3:1 FTOH)

Composition

C3F7CH2OH

CAS Number

375-01-9

Use

Used as monomers to produce side-chain fluorinated polymers. [1]Uses
Major applications

Acrylates or methacrylates of n:1 FTOHs are monomers used to produce side-chain
fluorinated polymers, which can be used as levelling agents, dispersants, and oil andwater repellents, especially for textiles and electronics [1], [5].

Regulatory Status
US

Together with the phase-out of other long-chain PFAS and in agreement with the EPA,
3M ceased its production of 7:1 FTOH (used to produce acrylate and methacrylatemonomer for side-chain fluorinated polymethacrylate-acrylate copolymers – e.g., CAS
Number 53515-73-4) in 2002. [1]Knowledge gaps

- Recent production and use volumes of n:1 FTOHs and their derivatives are unknown.
- Knowledge about the environmental fate of n:1 FTOHs is very limited, especially regarding their sidechain fluorinated acrylate and methacrylate polymers.
- Knowledge about other n:1 fluorotelomers is very sparse.
References
[1]

[2]

[3]
[4]
[5]

Z. Wang, I. T. Cousins, M. Scheringer, R. C. Buck, and K. Hungerbühler, “Global emission inventories
for C4–C14 perfluoroalkyl carboxylic acid (PFCA) homologues from 1951 to 2030, part II: The remaining
pieces of the puzzle,” Environ. Int., vol. 69, pp. 166–176, Aug. 2014.
B. Sha, E. L. Schymanski, C. Ruttkies, I. T. Cousins, and Z. Wang, “Exploring open cheminformatics
approaches for categorizing per- and polyfluoroalkyl substances (PFASs),” Environ. Sci. Process.
Impacts, vol. 21, no. 11, pp. 1835–1851, 2019.
D. R. Husted, and A. H. Ahlbrecht, “Fluorinated alcohols and acetate esters,” US 2666797, 1954.
OECD, “New Comprehensive Global Database of PFASs,” [Online]. Available:
https://www.oecd.org/chemicalsafety/portal-perfluorinated-chemicals/ [Accessed: 24-Jul-2020]
R. E. Banks, B. E. Smart, and J. C. Tatlow, Eds., Organofluorine Chemistry. Principles and Commercial
Applications. New York: Springer Science + Business Media, LLC, 1994.

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9. Perfluoroalkylethers (a), epoxides (b), and vinyl ethers (c) (non-polymers)
Chemical Information & Properties
Identification and Terminology
Name

Perfluoroalkylethers31
Trade names: Fluorinert
liquids; galden
fluorinated fluids [1]Perfluoroalkyl epoxides

Perfluorovinyl ethers

Acronym

PFEs

PFEp

PFVEs

Chemical Formula(linear isomers)e.g. CnF2n+1OCmF2m+1

CnF2nOCmF2m

RO(C3F6O)CF=CF2

DTXSID90893882

DTXSID501024682

DTXSID301024929

General Structure

US EPA CompTox
Markush ID
Synthesis
Main Synthesis
MethodElectrochemical
fluorination of aliphatic
ethers, alcohols, orcarboxylic acids, or
fluorination of etherswith cobalt fluoride orelemental fluorine undercontrolled conditions [1]

HFPO (hexafluoropropyleneoxide) is reacted with afluorinated alkoxide or othernucleophiles. This yields acidfluorides, which are thenconverted to acid salts that aresubsequently heated in an
aprotic environment to lose
carbon dioxide and metal
fluoride and yield PFVEs [1]Major Commercial Products
Name

FC-75

CAS Number

335-36-4

Composition

Mostly perfluorobutyltetrahydrofurans [1]Use

Solvent [1]Name

Hexafluoropropylene oxide (HFPO)CAS Number

428-59-1

Composition

C3F6O

Production/Import
volumes

Registered in Europe under REACH with a production/import volume of 100–1000
tonnes per year. [2]500 - <10,000t in the US in 2015 [4]31

For more examples of compounds in this group and their associated information, one may search for thefollowing IDs at the US EPA CompTox Chemicals Dashboard website: https://comptox.epa.gov/dashboard,
namely DTXSID90893882.
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ENV/CBC/MONO(2022)1  69

Use

Starting material for the synthesis of hexafluoroacetone, perfluoropolyethers, andfluorinated vinyl ethers. [1]Uses
Major applications

Perfluoroalkylether chemicals mentioned here and mixtures thereof (perfluorinatedfluids) are used in the electronics industry, as immersion coolants for supercomputers
and testing applications. [3]Knowledge gaps

- Little information is available on perfluoroalkylethers that do not feature acids groups or are consideredpolymers.
- There is limited to no information on their degradation or reported occurrences in the environment.
References
[1]
[2]

[3]

[4]

G. Siegemund et al., “Fluorine Compounds, Organic,” Ullmann’s Encycl. Ind. Chem., pp. 1–56, 2016.
European Chemicals Agency (ECHA), “Trifluoro(trifluoromethyl)oxirane – Registration Dossier”[Online]. Available: https://echa.europa.eu/registration-dossier/-/registered-dossier/5721. [Accessed:
05-Dec-2019].
M. G. Costello, R. M. Flynn, and J. G. Owens, “Fluoroethers and Fluoroamines,” in Kirk-Othmer
Encyclopedia of Chemical Technology, vol. 11, Hoboken, NJ, USA: John Wiley & Sons, Inc., 2004, pp.
1–12.
U.S. EPA, Chemical Data Reporting (CDR), 2016. Available at https://www.epa.gov/chemical-datareporting/access-cdr-data.

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10. Perfluoroalkenes (a) and derivatives (b)Chemical Information & Properties
Identification and Terminology
Name

Perfluoroalkenes

Other Names

Fluorinated Olefins; fluoroolefins

Chemical Formula

CnF2n (n>2)33

General Structure(linear isomers)(Examples ofderivatives shownon the right takenfrom [1])US EPA CompTox
Markush &Substance IDs

Perfluoroalkene derivatives32

CAS 88022-48-4

DTXSID201024683

CAS 120695-78-5

CAS 70829-87-7 (OBS, also see below
under Major Commercial Products)
DTXSID40897491, DTXSID20694127,
DTXSID601020833

Degradability, Mobility, Bioconcentration
Atmospheric lifetimes: 6 d for C3F6 [1]Degradation in theatmosphere
Reaction rate constants with OH-radicals: 2.6 (C3F6) × 10−12 cm3 molecules−1 s−1, yielding
CF3CFO and CF2O, then enter the aqueous phase in 5–10 days, where they are eventuallydegraded to HF and TFA, and HF and CO2, respectively. [2]Ozonolysis

Reaction with ozone under atmospheric conditions is slow [1], but perfluoroalkenes canbe broken down via reductive ozonolysis [3].

Biodegradation

OBS is non-readily biodegradable [4]Other degradation
methods

OBS can be decomposed by photolysis combined with hydrogen peroxide [4]Synthesis
Main Synthesis
MethodDehalogenation of halofluoroalkanes with zinc and an alcohol or dehydrohalogenation of
haloalkanes with alcoholic alkali or by heating. Alternatively, addition of hydrogen
halides to alkynes, decarboxylation of fluorocarboxylic acid salts, or pyrolysis of32

For more examples of compounds in this group and their associated information, one may search for thefollowing IDs at the US EPA CompTox Chemicals Dashboard website: https://comptox.epa.gov/dashboard,
namely DTXSID101010249, DTXSID401010250.
33
According to the revised PFAS definition in the latest OECD PFAS Terminology report(https://www.oecd.org/chemicalsafety/portal-perfluorinated-chemicals/), tetrafluoroethylene (TFE; CF2=CF2)
and hexafluorobutadiene (F2C–CF=CF–CF2) are not PFASs due to a lack of saturated fluorinated atoms.
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ENV/CBC/MONO(2022)1  71

fluorohydrocarbons are also common synthesis methods. [5]Perfluoroalkenes (such as C3F6 or C4F8) can also be released when fluoropolymers areincinerated and the polymers are degraded to release the monomers. [6]Other sources

Industrial Practices & Commercial Uses
Major Commercial Products
Name

Hexafluoropropene (HFP)

CAS Number

116-15-4

Use

Most importantly in the production of copolymers, e.g. with TFE or VDF, also to produce
the epoxide hexafluoropropylene oxide. [5]Production/Import
volumes

Registered in Europe under REACH with a production/import volume of 1000–10 000
tonnes per year. [7]5000 – <25,000t in the US in 2015 [8]Name

Sodium ρ-perfluorous nonenoxybenzene sulfonate (OBS)

Composition

C9F17OC6H4SO3Na

CAS Number

70829-87-7

Use

Additive for fire-fighting foams; surfactant for oil production, mainly used in China [9],[4]Production/Import
volumes

3500 tonnes/yr in China (reported in 2017) [9], [4]Degradation

Can be decomposed by UV/H2O2 or UV, while in aqueous solution [4]Examples of reported occurrences
Type oflocations/samples(Environmental) media

Detected in
one ormultipleregions

ExamplesLocation,year

Levels [min.–max. (detection
frequency)]

Non-detects are reported as below the value of the limit of detection (“<LOD”).
pg = picograms, ng = nanograms, ww = wet weight, ND = not detected, NR = not reported
airone
Close to point
China 2015 OBS: 9.9–110 ng/L (9/9)
surface water
sources
multiple (close to
soil
new
sediment
oilfield)

Not close to
specific point
sourcesair
surface watersoil
sedimentone
multiple

China 2015
(close toold oilfield)

OBS: 10–3200 ng/L (26/26)

China
2015

OBS: <0.96–19 ng/L (NR/8)

Ref.

[10]

Knowledge gaps

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

72  ENV/CBC/MONO(2022)1- Little information is available on long-chain perfluoroalkenes and derivatives.
- Environmental monitoring data are missing.
References
[1]
[2]
[3]
[4]

[5]
[6]

[7]
[8]
[9]

[10]

OECD, “New Comprehensive Global Database of PFASs,” [Online]. Available:
https://www.oecd.org/chemicalsafety/portal-perfluorinated-chemicals/ [Accessed: 24-Jul-2020]
G. Acerboni et al., “Atmospheric degradation and global warming potentials of three perfluoroalkenes,”
Atmos. Environ., vol. 35, no. 24, pp. 4113–4123, 2001.
K. I. Odinokov, I. F. R. Akhmetova, R. G. Savchenko, / I Y Bazunova, J. A. Yatykhov, and A. Y.
Zapevalov, “Ozonolysis of perfluoroalkenes and perfluorocycloalkenes,” 1997.
Y. Bao, Y. Qu, J. Huang, G. Cagnetta, G. Yu, and R. Weber, “First assessment on degradability of sodium
p-perfluorous nonenoxybenzene sulfonate (OBS), a high volume alternative to perfluorooctane sulfonate
in fire-fighting foams and oil production agents in China,” RSC Adv., vol. 7, no. 74, pp. 46948–46957,
2017.
G. Siegemund et al., “Fluorine Compounds, Organic,” Ullmann’s Encycl. Ind. Chem., pp. 1–56, 2016.
Z. Wang, I. T. Cousins, M. Scheringer, R. C. Buck, and K. Hungerbühler, “Global emission inventories
for C4–C14 perfluoroalkyl carboxylic acid (PFCA) homologues from 1951 to 2030, part II: The remaining
pieces of the puzzle,” Environ. Int., vol. 69, pp. 166–176, Aug. 2014.
European Chemicals Agency (ECHA), “Hexafluoropropene – Registration Dossier” [Online]. Available:
https://echa.europa.eu/registration-dossier/-/registered-dossier/15192. [Accessed: 13-Dec-2019].
U.S. EPA, Chemical Data Reporting (CDR), 2016. Available at https://www.epa.gov/chemical-datareporting/access-cdr-data.
C. Wang et al., “Bioaccumulation in the gut and liver causes gut barrier dysfunction and hepatic
metabolism disorder in mice after exposure to low doses of OBS,” Environ. Int., vol. 129, pp. 279–290,
Aug. 2019.
L. Xu et al., “Discovery of a Novel Polyfluoroalkyl Benzenesulfonic Acid around Oilfields in Northern
China,” Environ. Sci. Technol., vol. 51, no. 24, pp. 14173–14181, 2017.

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ENV/CBC/MONO(2022)1  73

11. Specific hydrofluoro-carbons (a), -ethers (b), and -olefins (c) 34
Chemical Information & Inherent Properties
Identification and Terminology35
Name

Hydrofluorocarbons

Hydrofluoroethers

Other Names

Hydrofluoroolefins
Fluorinated olefins [1]Acronym

HFCs

HFEs

HFOs

Chemical Formula(those with at least
one saturated fully
fluorinated carbon
atom)

CnHxFywith x + y = 2n + 2

CnHxFyOCmHpFq
with x + y = 2n + 1;
p + q = 2m + 1;
x+ y + p + q = 2(n + m +1)

CnHxFywith x + y = 2n

Between 0.8 (HFE-7200;
C4F9OCH3) and 165 (HFE125; CHF2OCF3) years [3]ca.10 d (HFO-1234yf;
CF3CF=CH2) [4,5]Degradability, Mobility, Bioconcentration
Atmospheric lifetime

13.4 years (HFC-134a;
CH2FCF3) [2]Atmospheric reactions with OH radicals can yield PFCAs. [1], [6] For HFCs and HFOs
used as refrigerants and foam blowing agents, some yield TFA (trifluoroacetic acid) andnot longer-chain PFCAs. [7] [8] [9]Ozone Depletion
Potential (ODP)

Between 10−5 and 10−3
(varying between studies)[10]. Atmospheric changes
in temperature andcirculation arising from
HFC emissions lead to aweak, indirect depletion ofstratospheric ozone [11].

Negligible [12]Negligible [9]100 Year Global
Warming Potential(GWP)

Between 1300 (HFC-134a)and 8060 (HFC-236fa;
CF3CH2CF3) [2]

Between 60 (HFE-7200)
and 14 000 (HFE-125) [3]<1 (HFO-1234yf) [2]2 (HFO-1336mzz;
CF3CH=CHCF3) [2]

Biodegradation(The commercially relevant) HFCs, HFEs, and HFOs are gases with low watersolubility. They almost entirely partition into the atmosphere, with atmosphericdegradation as a major degradation process. For this reason and others, there are limited
data on biodegradation or bioconcentration.

Bioconcentration

Synthesis
Main Synthesis

Addition of hydrogen

Synthesized from alkoxides

Dehalogenation of

34

Note that not all HFCs, HFEs and HFOs are included here, but only those that contain at least one
perfluorinated methyl (–CF3) or methylene (–CF2–) group. Many HFCs and HFOs used as refrigerants andfoam blowing agents do not fall under PFAS according to the revised PFAS definition in the latest OECD PFAS
Terminology report (https://oe.cd/2M9), e.g. those having CF2XY (where X and Y ≠ F) structures.
35
Common naming conventions have been established for HFCs, HFEs, HFOs and many other fluorinatedgases; for more details, see for example https://www.fluorocarbons.org/wp-content/uploads/2020/06/EFCCNamingNumbering_A4_V01-23062020.pdf;
https://eur-lex.europa.eu/legalcontent/EN/TXT/PDF/?uri=CELEX:32014R0517&from=EN.

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74  ENV/CBC/MONO(2022)1
Methodfluoride to olefins or
alkynes; exchange ofchlorine for fluorine, via
hydrogen fluoride or metal
fluorides; addition ofhydrogen toperfluoroalkenes;
decarboxylation of
perfluorocarboxylates;
electrochemical
fluorination. [1]or phenoxides andfluoroolefins. [1]Possible Impurities

haloalkanes;
dehydrohalogenation ofhydrogen-containing
haloalkanes; addition ofhydrogen halides toalkynes; decarboxylation offluorocarboxylic acids;
pyrolysis offluorohydrocarbons. [1]CHCl2F andhexafluoropropene in the
production oftetrafluoroethylene. [1]Industrial Practices & Commercial Uses
Major Commercial ProductsName(s)1,1,1,2-Tetrafluoroethane

Trade Name(s)HFC-134a / R-134a / Freon 134a / Forane 134a / Genetron 134a / Florasol 134a / Suva
134a / Norflurane

Chemical Formula

CH2FCF3

CAS Number

811-97-2

Use

See Major applications below.

Production/Import
volumes

Between 1990 and 1995, 159 500 t have been produced [1]. HFC-134a is registered in
the EU under REACH with a production/import volume of 10 000 – 100 000 tonnes per
year [13].
50,000 - <125.000t in the US in 2015 [14]Name(s)2,3,3,3-Tetrafluoropropene

Trade Name(s)HFO-1234yf / R-1234yf / Opteon YF / Solstice YF / HFC-1234yf

Chemical Formula

CH2=CFCF3

CAS Number

754-12-1

Use

See Major applications below.

Production/Import
volumes

Registered in the EU under REACH with a production/import volume of 1000 –10 000 tonnes per year. [15]500 - <10,000t in the US in 2015 [14]Uses
Major applications

HFCs are mostly used as
substitutes for CFCs and
HCFCs: in refrigeration
and air-conditioning, as
propellants in aerosols, andas foaming agents inclosed cell foams (e.g. forbuilding insulation), as

HFEs replace HFCs insome of the applications
mentioned, due to theirlower global warming
potential [6]. Some HFEs
are also used as inhalation
anesthetics. [1]Replacements for HFCs
and HFEs [17].
Production of fluorinatedpolymers and inert fluids[1].

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ENV/CBC/MONO(2022)1  75

well as in fire
extinguishing systems, andother applications [1], [16],[7]. HFC-134a and HFC227ea (CF3CFHCF3) havebeen used as propellants
for metered dose inhalers.
[7]
Regulatory Status
US

Under the SNAP (Significant New Alternatives Policy) Program the US EPA identifies
and approves climate-friendly alternatives for ozone-depleting substances. Federal
Agencies have to report their greenhouse gas emissions, including HFC emissions, andhave to procure alternatives to HFCs with high global warming potentials, if possible.
[16]. Several US states have implemented stricter regulations to reduce HFC emissions.
[18]. In December 2020, the US passed the American Innovation and Manufacturing Act,
mandating an 85 % phasedown of HFCs by 2036, consistent with the Kigali Amendment
and other emission-reducing measures. [19]European Union

The F-gas Regulation 517/2014 limits the total amount of fluorinated greenhouse gases(including HFCs, perfluorocarbons, Sulphur hexafluoride and other greenhouse gases that
contain fluorine, listed in Annex I; note that HFEs and HFOs are not addressed by thisregulation) that can be sold in the EU, with the goal to cut emissions by two-thirds by2030 compared to 2014. Use of these gases is banned where less harmful alternatives areavailable, and emissions are to be prevented by proper servicing of equipment andrecovery of the gases at the end of the product life cycle. The regulation also setsrequirements of reporting on production, import, export, feedstock use and destruction of
the substances listed in Annexes I or II (including HFO, HFEs and other perfluorinatedcompounds). [20]The use of refrigerants in new cars (in heating, ventilation and air conditioning), whichhave global warming potentials higher than 150 (which includes HFC-134a) is prohibitedby the MAC Directive [17], [20].

CanadaHFCs are regulated pursuant to the Ozone-depleting Substances and Halocarbon
Alternatives Regulations. The purpose of these Regulations is to implement Canada’s
obligations under the Montreal Protocol, including the Kigali amendment, by setting out
rules concerning HFCs and certain products containing or designed to contain HFCs [21].

International efforts
The Kigali Amendment to the Montreal Protocol specifically addresses HFCs (not HFEs and HFOs), with thegoal to reduce HFC production and consumption by 85 % by 2036 for developed countries, by 80 % by 2045 formost developing countries and by 85 % by 2047 for a small group of developing countries (reduction based on
baseline levels). [22] The Amendment came into effect in 2019, with some countries that are parties to theProtocol yet to ratify the amendment. [18]The Scientific Assessment Panel and the Environmental Effects Assessment Panel to the Montreal Protocol
provide regular updates on emissions and environmental fate of HFCs [23, 24].

Examples of reported occurrences
Type oflocations/samples(Environmental)
media

Detected in
one ormultipleregions

ExamplesLocation,year

Levels [min. –max. (detection
frequency)]

Ref.

Non-detects are reported as below the value of the limit of detection (“<LOD”).

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76  ENV/CBC/MONO(2022)1
ppt = parts per trillion, pptv = parts per trillion (volume fraction), ND = not detected, NR = not reported
airone
Not close to
China
HFC-134a: 87 pptv (mean)[25]
surface water
multiple 2010
specific point(NR/92)sourcessoil
US
HFC-134a: 65.4 pptv (mean) (NR)sediment
2010
Globalsurfacemean
2016

HFC-125: 20.1–20.8 ppt (means
derived by different methods)
HFC-134a: 89.3–92.1 ppt (means
derived by different methods)
HFC-143a (CH3CF3): 19.0–19.3
ppt (means derived by different
methods)
HFC-245fa (CHF2CH2CF3): 2.43
ppt (mean)
HFC-365mfc (CF3CH2CF2CH3):
0.87–1.0 ppt (means derived bydifferent methods)
HFC-227ea: 1.17–1.24 ppt (means
derived by different methods)
HFC-43-10mee(CF3CHFCHFCF2CF3): 0.27 ppt(mean)
HFC-236fa: 0.15 ppt (mean)[23]

Urban area

air
surface watersoil
sedimentone
multiple

Switzerland
2016

HFO-1234yf: <0.003–approx. 9.2ppt (NR)
HFO-1234ze (transCHF=CHCF3): <0.003–approx. 25
ppt (NR)[23]

Remoteregionsair
surface water
soil

one
multiple

Swiss alps
2004

HFC-134a: approx. 30–approx.
130 ppt (NR)[26]

Italian alps
2004

HFC-134a: approx. 30–approx.
140 ppt (NR)

Swiss alps
2016

HFO-1234yf: <0.003–approx. 8.2ppt (NR)
HFO-1234ze: <0.003–approx. 10ppt (NR)sediment[23]

Knowledge gaps

- Environmental concentrations of less commonly known HFEs and some of the newer HFOs.
References[1][2]

G. Siegemund et al., “Fluorine Compounds, Organic,” Ullmann’s Encycl. Ind. Chem., pp. 1–56, 2016.
Myhre, G., D. Shindell, F.M. Bréon, W. Collins, J. Fuglestvedt, J. Huang, D. Koch, J.F. Lamarque, D.
Lee, B. Mendoza, T. Nakajima, A. Robock, G. Stephens, T. Takemura and H. Zhang, 2013:
Anthropogenic and Natural Radiative Forcing. In: Climate Change 2013: The Physical Science Basis.
Contribution of Working Group I to the Fifth Assessment Report of the Intergovernmental Panel on
Climate Change [Stocker, T.F., D. Qin, G.K. Plattner, M. Tignor, S.K. Allen, J. Boschung, A. Nauels,

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ENV/CBC/MONO(2022)1  77

[3]

[4]

[5]

[6]

[7]
[8]
[9]

[10]
[11]
[12]
[13]
[14]
[15]

[16]
[17]
[18]
[19]

[20]
[21]

[22]

Y.Xia, V. Bex and P.M. Midgley (eds.)]. Cambridge University Press, Cambridge, United Kingdom
and New York, NY, USA.
T. J. Wallington and O. J. Nielsen, “Atmospheric Chemistry and Environmental Impact ofHydrofluorocarbons (HFCs) and Hydrofluoroethers (HFEs),” in The Handbook of Environmental
Chemistry Vol. 3, Part N Organofluorines, A. H. Neilson, Ed. Berlin Heidelberg: Springer-Verlag, 2002.
O. J. Nielsen, M. S. Javadi, M. P. Sulbaek Andersen, M. D. Hurley, T. J. Wallington, and R. Singh,“Atmospheric chemistry of CF3CF CH2: Kinetics and mechanisms of gas-phase reactions with Cl
atoms,OH radicals, and O3,” Chem. Phys. Lett., vol. 439, no. 1–3, pp. 18–22, May 2007.
European Chemicals Agency (ECHA), “2,3,3,3-tetrafluoroprop-1-ene - Registration Dossier.”[Online]. Available: https://echa.europa.eu/registration-dossier/-/registered-dossier/16012. [Accessed:
27-Jan-2020].
Z. Wang, I. T. Cousins, M. Scheringer, R. C. Buck, and K. Hungerbühler, “Global emission inventories
for C4–C14 perfluoroalkyl carboxylic acid (PFCA) homologues from 1951 to 2030, part II: Theremainingpieces of the puzzle,” Environ. Int., vol. 69, pp. 166–176, Aug. 2014.
IPCC/TEAP, “Special Report Safeguarding the Ozone Layer and the Global Climate System: Issues
Related to Hydrofluorocarbons and Perfluorocarbons”, 2005.
World Meteorological Organisation, “Global Ozone Research and Monitoring Project Report No.
52. Scientific Assessment of Ozone Depletion”, 2010
T. J. Wallington, M. P. Sulbaek Andersen and O. J. Nielsen,“Atmospheric chemistry of short-chain
haloolefins: Photochemical ozone creation potentials (POCPs), global warming potentials (GWPs),
and ozone depletion products (ODPs),” Chemosphere, vol. 129, pp. 135-141, 2015.
M. M. Hurwitz et al., “Ozone depletion by hydrofluorocarbons,” Geophys. Res. Lett., vol. 42, no. 20,
pp.8686–8692, Oct. 2015.
M. M. Hurwitz, E. L. Fleming, P. A. Newman, F. Li and Q. Liang, “Early action on HFCs mitigates
future atmospheric change,” Environ. Res. Lett., vol. 11, 2016.
P. Blowers, D. M. Moline, K. F. Tetrault, R. R. Wheeler, and S. L. Tuchawena, “Global Warming
Potentials of Hydrofluoroethers,” Environ. Sci. Technol., vol. 42, no. 4, pp. 1301–1307, Feb. 2008.
“Norflurane - Registration Dossier - ECHA.” [Online]. Available: https://echa.europa.eu/registrationdossier/-/registered-dossier/15155.[Accessed: 27-Jan-2020].
U.S. EPA, Chemical Data Reporting (CDR), 2016. Available at https://www.epa.gov/chemical-datareporting/access-cdr-data.
“2,3,3,3-tetrafluoroprop-1-ene Registration
Dossier ECHA.”[Online]
Available: https://echa.europa.eu/registration-dossier/-/registered-dossier/16012.[Accessed: 29-Jul2020].
U.S. Environmental Protection Agency (EPA), “Reducing HFC Emissions in the Federal Sector,”
2016.
G. Raabe and E. J. Maginn, “A Force Field for 3,3,3-Fluoro-1-propenes, Including HFO-1234yf,” J.
Phys.Chem. B, vol. 114, no. 31, pp. 10133–10142, Aug. 2010.
A. Ulrich, “Feature: In the crosshairs – hydrofluorocarbons in the US,” Chemical Watch, 2019.
United States Congress, ” S.2754 - American Innovation and Manufacturing Act of 2019.” 2019.
[Online]. Available: https://www.congress.gov/bill/116th-congress/senate-bill/2754/text[Accessed: 0705-2021]
European Commission, “EU legislation to control F-gases | Climate Action.” [Online]. Available:
https://ec.europa.eu/clima/policies/f-gas/legislation_en.[Accessed: 28-Jan-2020].
Canada, ”Ozone-depleting Substances and Halocarbon Alternatives Regulations, SOR/2016-137.”
2016.
[Online].
Available::https://laws-lois.justice.gc.ca/eng/regulations/SOR-2016137/FullText.html [Accessed: 07-05-2021]
UNIDO, “Way to go wuth UNIDO. Mapping the HFC phase-down.” [Online]. Available:
https://www.unido.org/sites/default/files/files/2020-04/UNIDO-brochure_HFC-Phase_Down-

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[23]
[24]

[25]
[26]

Complete.pdf[Accessed: 07-May-2021].
World Meteorological Organization, “Scientific Assessment of Ozone Depletion: 2018, Global Ozone
Research and Monitoring Project, Report No. 58,” Geneva, Switzerland, 2018.
EEAP, “Environmental Effects and Interactions of Stratospheric Ozone Depletion, UV Radiation, andClimate Change 2018 Assessment Report,“ Environmental Effects Assessment Panel, United Nations
Environment Programme (UNEP), 2019.
X. Fang et al., “Ambient mixing ratios of chlorofluorocarbons, hydrochlorofluorocarbons andhydrofluorocarbons in 46 Chinese cities,” Atmos. Environ., vol. 54, pp. 387–392, Jul. 2012.
M. Maione et al., “Localization of source regions of selected hydrofluorocarbons combining datacollected at two European mountain stations,” Sci. Total Environ., vol. 391, no. 2–3, pp. 232–240,
Mar. 2008.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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12. Side-chain fluorinated aromatics
Chemical Information & Inherent Properties
Identification and Terminology
NameSide-chain fluorinated aromatics

Other Names

Aromatic compounds with perfluorocarbon moieties on the side chain(s)Chemical Formulae.g. C6R5CnF2n+1

Exemplary Structure(linear isomers)

Note that fluorinated side chains may also be attached via other types of bonds, e.g. via
an ester bond.
General remarks

Benzotrifluorides (e.g. C6R5CF3, n=1) are a group of commercially relevant side-chain
fluorinated aromatics [1]. As there is little information on other side-chain fluorinatedaromatics, this fact card focuses on benzotrifluorides and their derivatives.

Degradability, Mobility, Bioconcentration
Biodegradation

No biodegradation of benzotrifluoride (BTF) in activated sludge after 28 days [2];Complete mineralization of fluorinated drugs is rare. Fluoxetine (see in section oncommercial products below) is not eliminated by conventional wastewater treatment, but
is removed via ozone or active carbon [3]–[5].
Fluometuron (see in section on commercial products below) is not readily biodegradable[6].

Bioaccumulation

BCF (aquatic species) of BTF = 58 [2]BCF (fish) of fluoxetine = 8.8–260 (estimated) [7]
BCF (fish) of norfluoxetine = 80–650 (estimated) [7]
BCF (mussels) of fluoxetine = 125–1347 [8]Synthesis
Main Synthesis
MethodHalogen exchange using hydrogen fluoride [1]:𝐶6 𝐻5 𝐶𝐶𝑙3 + 3 𝐻𝐹 →𝐶6 𝐻5𝐶𝐹3 + 3 𝐻𝐶𝑙

Possible Impurities

Typically, a yield between 70–90% is obtained, depending on the specific process
conditions. It remains unclear what side products and possible impurities are generated.
[1]

Industrial Practices & Commercial Uses
Major Commercial Products
Name

Benzotrifluoride / α,α,α-trifluorotoluene / trifluoromethylbenzene

Acronym

BTF

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Chemical Formula

C6H5CF3

CAS Number

98-08-8

Use

Intermediate in the synthesis of dyes, pesticides, and pharmaceuticals.

Production/Import
volumes

Registered in the EU under REACH with a production/import volume of 0–10 tonnes per
year. [2]Name4-chlorobenzotrifluoride / Parachlorobenzotrifluoride

Acronym

4CBTF / PCBTF

Trade Name(s)Oxsol 100 [9]Chemical Formula

C6H4ClCF3

CAS Number

98-56-6

Use

Solvent, especially for paint and ink formulations; cosmetic stain remover; aerosol rust
inhibitor [9]Production/Import
volumes

Registered in the EU under REACH with a production/import volume of 100–1000
tonnes per year. [10]5,000 - <25,000t in the US in 2015 [16]Name

Fluoxetine

Trade Name(s)(active ingredient in) Prozac [8]Chemical Formula

C17H18F3NO

CAS Number

54910-89-3

Use

Antidepressant, specifically selective serotonin reuptake inhibitor (SSRI) [8]

Production/Import
volumesVolumes sold in 2003 and 2004: 3.7 t/yr (France), 4.8 t/yr (UK), 4.2 t/yr (Spain) [4]Name

N,N-dimethyl-N′-[3-(trifluoromethyl)-phenyl]-urea

Trade Name(s)Fluometuron

Chemical Formula

C10H11F3N2O

CAS Number

2164-17-2

Use

Herbicide, especially used in cotton production [1], [11]Production/Import
volumes

Registered in the EU under REACH with a production/import volume of 10–100 tonnes
per year. [6]Uses
Major applications

Benzotrifluorides derivatives are used as dyes, where the trifluoromethyl group improvescolor clarity, as well as pharmaceuticals [12] and pesticides, since the trifluoromethylgroup accelerates absorption [1]. BTF and PCBTF are also used as organic solvents [13].

Examples of reported occurrences
Type oflocations/samples(Environmental)
media

Detected in
one ormultipleregions

ExamplesLocation,year

Levels [min. –max. (detection
frequency)]

Ref.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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ENV/CBC/MONO(2022)1  81

Non-detects are reported as below the value of the limit of detection (“<LOD”).
ng = nanograms, ww = wet weight, ND = not detected, NR = not reported
airone
Close to point
US (close to Fluoxetine: 17.4 ng/g ww (mean)surface water
sources(NR/12)
multiple WWTP
effluent)
soil
2010
sediment(year ofpublication)
Groundwater
Italy 2008
BTF: 98 ng/L (mean) (3/3)(Valleagno
area, site of 4-Chloro-BTF: 11900 ng/L(mean) (3/3)
chemicalspill in
3,4-dicholoro-BTF: 6400 ng/L
1977)
(mean) (3/3)

[8]

[15]

2,4-dicholoro-BTF: 220 ng/L(mean) (3/3)
3-nitro-BTF: 430 ng/L (mean)(3/3)
3-amino-BTF: 580 ng/L (mean)(3/3)
3-amino-4-chloro-BTF: 2600
ng/L (mean) (3/3)
3-nitro-4-chloro-BTF: 5900 ng/L(mean) (3/3)
Not close to
specific point
sourcesair
surface watersoil
sedimentone
multiplePortugal
2013–2014

Fluoxetine: 2.01–19.5 ng/L
(55/55)

[14]

WWTP

effluent
influent
sludgeone

Portugal
2013–2014

Fluoxetine: 5.21–17.8 ng/L
(55/55)[14]

Portugal
2013–2014

Fluoxetine: 10.5–34.0 ng/L
(55/55)[14]

US 2010(year ofpublication)

Fluoxetine: 118.8 ng/L (mean)(NR/6)[8]

US 2010(year ofpublication)

Fluoxetine: 79.1 ng/g ww (mean)
(NR)

[8]

multipleeffluent
influent
sludgeWildlife

Freshwater
mussels (Elliptio
complanata) at
WWTP effluent

one
multiple

Knowledge gaps

- Biodegradation properties of many side-chain fluorinated aromatics are still not thoroughly investigated.
[3]

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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82  ENV/CBC/MONO(2022)1- Current production volumes are unknown, especially outside the EU.
- Environmental monitoring data are sparse.
References
[1]
[2]

[3]

[4]

[5]

[6]
[7]
[8]
[9]

[10]

[11]
[12]
[13]
[14]

[15]
[16]

G. Siegemund et al., “Fluorine Compounds, Organic,” Ullmann’s Encycl. Ind. Chem., pp. 1–56, 2016.
European Chemicals Agency (ECHA), “α,α,α-trifluorotoluene - Registration Dossier” [Online].
Available: https://echa.europa.eu/registration-dossier/-/registered-dossier/29639. [Accessed: 08-Jan2020].
C. D. Murphy, “Microbial degradation of fluorinated drugs: biochemical pathways, impacts on theenvironment and potential applications,” Appl. Microbiol. Biotechnol., vol. 100, no. 6, pp. 2617–2627,
Mar. 2016.
S. C. Monteiro and A. B. A. Boxall, “Occurrence and Fate of Human Pharmaceuticals in theEnvironment,” in Reviews of Environmental Contamination and Toxicology 202, D. M. Whitacre, Ed.
2010, pp. 53–154.
C. H. Redshaw, M. P. Cooke, H. M. Talbot, S. McGrath, and S. J. Rowland, “Low biodegradability offluoxetine HCl, diazepam and their human metabolites in sewage sludge-amended soil,” J. Soils
Sediments, vol. 8, no. 4, pp. 217–230, Sep. 2008.
“Fluometuron - Registration Dossier - ECHA.” [Online]. Available: https://echa.europa.eu/registrationdossier/-/registered-dossier/16818. [Accessed: 22-Jan-2020].
A. Puckowski et al., “Bioaccumulation and analytics of pharmaceutical residues in the environment: A
review,” J. Pharm. Biomed. Anal., vol. 127, pp. 232–255, Aug. 2016.
R. B. Bringolf et al., “Environmental occurrence and reproductive effects of the pharmaceuticalfluoxetine in native freshwater mussels,” Environ. Toxicol. Chem., vol. 29, no. 6, pp. 1311–1318, 2010.
“Parachlorobenzotrifluoride (PCBTF) - Silver Fern Chemical Inc.” [Online]. Available:
https://www.silverfernchemical.com/products/parachlorobenzotrifluoride-pcbtf/. [Accessed: 13-Jan2020].
European Chemicals Agency (ECHA), “4-chloro-α,α,α-trifluorotoluene - Registration Dossier.”[Online]. Available: https://echa.europa.eu/registration-dossier/-/registered-dossier/5322. [Accessed: 13Jan-2020].
M. A. Locke, R. M. Zablotowicz, and L. A. Gaston, “Environmental Fate of Fluometuron in a Mississippi
Delta Lake Watershed,” 2002, pp. 206–225.
J. Wang et al., “Fluorine in Pharmaceutical Industry: Fluorine-Containing Drugs Introduced to the Market
in the Last Decade (2001-2011),” Chemical Reviews, vol. 114, pp. 2432–2506, 2014.
J. J. Maul, P. J. Ostrowski, G. A. Ublacker, B. Linclau, and D. P. Curran, “Benzotrifluoride andDerivatives: Useful Solvents for Organic Synthesis and Fluorous Synthesis,” 1999, pp. 79–105.
P. Paíga, L. H. M. L. M. Santos, S. Ramos, S. Jorge, J. G. Silva, and C. Delerue-Matos, “Presence ofpharmaceuticals in the Lis river (Portugal): Sources, fate and seasonal variation,” Sci. Total Environ., vol.
573, pp. 164–177, 2016.
R. Lava, E. Aimo, L. Menegus, G. Pojana, and A. Marcomini, “Determination of benzotrifluoride
derivative compounds in groundwater,” Anal. Chim. Acta, vol. 804, pp. 126–134, Dec. 2013.
U.S. EPA, Chemical Data Reporting (CDR), 2016. Available at https://www.epa.gov/chemical-datareporting/access-cdr-data

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13. Fluoropolymers
Key publications: Dams, Rudy, and Klaus Hintzer. 2017. “Chapter 1. Industrial Aspectsof Fluorinated Oligomers and Polymers.” In Fluorinated Polymers: Volume 2:
Applications, edited by Bruno Ameduri and Hideo Sawada, 1–31. Royal Society ofChemistry. https://doi.org/10.1039/9781782629368-00001.
Ebnesajjad, S., Introduction to Fluoropolymers – Materials, Technology and Applications.
Plastics Design Library (PDL) Handbook Series. Elsevier. 2011

Chemical Information & Inherent Properties
Identification and Terminology
Name

Fluoropolymers

Other Names

Fluoroplastics

Chemical Formula(Examples)(C2F2)n (PTFE) / (C2H2F2)n (PVDF, ETFE)

General Structure(Examples, left:
PTFE, right: FEP)

Note: End-groups of these polymers can differ. Beside non-functionalized ones (as shown
above), functional end-groups (e.g. carboxyl end-groups) are also possible.
Examples of major fluoropolymers (adapted from [1])TFE Co-polymers

Homopolymers

+

+

+

+

+

PPVE

HFP

Ethene

HFP

CTFE

+

+

VDF

Ethene

+
TFE

CTFE

VDF

↓

↓

↓

↓

↓

↓

↓

↓

↓

PFA

FEP

ETFE

THVs

ECTFE

Teflon AF

PTFE

PCTFE

PVDF

Acronyms: TFE = tetrafluoroethylene; PPVE = perfluoropropylvinylether; HFP = xexafluoropropylene; VDF = vinylidene fluoride;
CTFE = chlorotrifluoroethyle; VF = vinyl fluoride

Degradability, Mobility, Bioconcentration
Abiotic degradation Fluoropolymers exhibit high chemical resistance and weather resistance. [2]Thermal degradation Fluoropolymers are stable up to high temperatures, e.g., PTFE is stable up to 250 °C. Thermal
degradation begins slowly at higher temperatures and results mainly in monomer formation(e.g. tetrafluoroethylene), although the formation of hydrogen fluoride is also possible athigher temperatures [2]–[4]. Also, the formation of C2–C14 per- and polyfluoroalkyl
carboxylic acids have been reported. [5], [6]Synthesis
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Main Synthesis
MethodFree-radical polymerization, either in aqueous suspension or aqueous emulsion. The latteroften requires fluorinated emulsifiers (fluorosurfactants) as polymerization aids. Water
soluble peroxides or trialylboron catalysts are used to initiate the polymerization process. [7],[8] In some cases, free-radical solvent polymerization can also be utilized.36

Possible Impurities Residues of fluorosurfactants, used as processing aids in the emulsion polymerization
process, can potentially remain in the final products and can be released during later lifecycle stages [8]. Low molecular weight oligomers are also produced and can be released tothe environment [9].
Industrial Practices & Commercial Uses
Major Commercial ProductsName(s)

Polytetrafluoroethylene (PTFE)

Trade Name(s)TeflonChemical Formula–[CF2–CF2]n–CAS Number

9002-84-0

Use

Chemical processing, resistant components & coatings, pipes, fittings, linings, tapes, seals,
filters, wire & cable insulation, laminates, waterproof & stain repellent clothing, architectural
coatings, printing, cookware, fabrics, biomedical devices [8]Production/Import
volumesGlobal production in 2013: 200 000 tonnes; 15 000 tonnes produced in Europe [10]Global demand in 2016: 160 000 tonnes [3]Name(s)Polyvinylidene fluoride (PVDF)

Chemical Formula–[CH2–CF2]n–CAS Number

24937-79-9

Use

Fluid handling systems, valves, pumps, water piping, resistant paints, architectural coatings,
wire & cable insulation, electronic components, solar panels, printing [7]Production/Import
volumesGlobal consumption in 2012: 35 500 tonnes [11]Global demand in 2016: 33 000 tonnes [3]Name(s)Fluorinated ethylene propylene (FEP)

Chemical Formula–[CF2–CF2]n–[CF2–CF(CF3)]m–

CAS Number

25067-11-2

Use

Chemically resistant components & coatings, plenum cable insulation [7]Production/Import
volumesGlobal demand in 2016: 40 000 tonnes [3]Name(s)

Perfluoroalkoxy alkane (PFA) / Perfluoroalkoxy polymer

Chemical Formula–[CF2–CF2]n–[CF2–CF(ORF)]m– (RF = fluorinated group)

CAS Number

26655-00-5 / 31784-04-0

Use

Chemical processing, resistant components and fittings, electrical insulation, industrial &architectural coatings, semiconductor manufacturing [4], [7]36According to information provided by representatives of the manufacturing industry.

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Uses
Major applications Chemically resistant coatings and linings in chemical processing (e.g. pipe linings, tanks,
reaction vessels, valves, membranes), electrical insulation, nonstick coatings (e.g. forcookware), high-performance textiles, medical devices (such as catheters, heart patches,sutures, and others) [3]Regulatory Status
General remarks

In the US, fluoropolymers and their safety are reviewed in the context of specific applications(e.g. as food contact materials or for use in a medical context) by the US EPA, the US FDA,
and the US Consumer Product Safety Commission, and similarly in the EU [2], [3].

Examples of reported occurrences
Type oflocations/samples(Environmental)
media

Detected in
one ormultipleregions

ExamplesLevels [min. –max. (detection
frequency)]

Ref.

Non-detects are reported as below the value of the limit of detection (“<LOD”).
pg = picograms, ng = nanograms, ww = wet weight, ND = not detected, NR = not reported
airone
Remote regions
Arctic ocean 0.89–9.43 particles/kg sedimentsurface water(9/9; PTFE)
multiple 2015
soil
sediment[12]

Location,year

Knowledge gaps

- Quantified environmental occurrences of fluoropolymers, especially others than PTFE, are largely unknown.
- Production volumes are not publicly available.
- Limited information is available regarding chemical identities of commercial PFPE products (including
molecular weight range, molar ratio and composition of monomer units, impurity content, functional groups).
- More information is needed on how much PFCAs and other organofluorine compounds are currently emitted
from fluoropolymers throughout their life cycle, although fluoropolymer manufacturing was shown to be amajor historical source of PFOA in the environment.
References
[1]

[2]
[3]
[4]

[5]
[6]

K. Hintzer, and W. Schwertfeger, “Fluoropolymers – Environmental Aspects,” in Handbook of
Fluoropolymer Science and Technology, D. W. Smith, S. T. Iacono, and S. S. Iyer, Eds. Hoboken, NJ,
USA: John Wiley & Sons, Inc., 2014.
H. Teng, “Overview of the Development of the Fluoropolymer Industry,” Appl. Sci., vol. 2, no. 2, pp. 496–
512, 2012.
J. G. Drobny, Technology of Fluoropolymers, Second. Boca Raton, London, New York: CRC Press, Taylor& Francis Group, 2009.
R. Dams and K. Hintzer, “Chapter 1. Industrial Aspects of Fluorinated Oligomers and Polymers,” inFluorinated Polymers: Volume 2: Applications, B. Ameduri and H. Sawada, Eds. Royal Society ofChemistry, 2017, pp. 1–31.
D. Ellis, S. Mabury, J. Martin, and D. Muir, “Thermolysis of fluoropolymers as a potential source of
halogenated organic acids in the environment,” Nature, vol. 412, no. 6844, pp. 321-324, 2001.
D. Ellis, J. Martin, D. Muir, and S. Mabury, “The use of 19F NMR and mass spectrometry for the
elucidation of novel fluorinated acids and atmospheric fluoroacid precursors evolved in the thermolysis of

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[7]
[8]
[9]

[10]

[11]
[12]

fluoropolymers,” The Analyst, vol. 128, no. 6, pp. 756-764, 2003.
J. Gardiner, “Fluoropolymers: Origin, Production, and Industrial and Commercial Applications,” Aust. J.
Chem., vol. 68, no. 1, p. 13, 2015.
R. C. Buck et al., “Perfluoroalkyl and polyfluoroalkyl substances in the environment: Terminology,
classification, and origins,” Integr. Environ. Assess. Manag., vol. 7, no. 4, pp. 513–541, Oct. 2011.
S. Newton, R. McMahen, J. Stoeckel, M. Chislock, A. Lindstrom, and M. Strynar, “Novel PolyfluorinatedCompounds Identified Using High Resolution Mass Spectrometry Downstream of Manufacturing Facilities
near Decatur, Alabama,” Environ. Sci. Technol., vol. 51, no. 3, pp. 1544–1552, 2017.
“PTFE
globalandEuropean
production
2013,”
Statista.
[Online].
Available:
https://www.statista.com/statistics/732006/polytetrafluoroethylene-production-worldwide-and-in-europe/.
[Accessed: 30-Jan-2020].
Industry Experts, “Polyvinylidene Fluoride (PVDF)-A Global Market Overview,” 2016.
M. Bergmann et al., “High Quantities of Microplastic in Arctic Deep-Sea Sediments from the
HAUSGARTEN Observatory,” Environ. Sci. Technol., vol. 51, no. 19, pp. 11000–11010, Oct. 2017.

Additional References:
Hougham, G.; Cassidy, P. E.; Johns, K.; Davidson, T.; Editors, Fluoropolymers 2: Properties. In Springer,
New York, NY., 1999; Vol. Topics in Applied Chemistry. http://doi.org/10.1007/b114560
Ameduri, B., Fluorinated (Co)Polymers: Synthesis, Properties, and Applications. In Encyclopedia of
Polymer Science and Technology, Wiley: 2012; https://doi.org/10.1002/0471440264.pst575
Gangal, S. V.; Brothers, P. D., Perfluorinated Polymers, Perfluorinated Ethylene–Propylene Copolymers.
In Encyclopedia of Polymer Science and Technology, John Wiley & Sons, Inc.: 2002;
http://doi.org/10.1002/0471440264.pst417.pub2
Gangal, S. V.; Brothers, P. D., Perfluorinated Polymers, Tetrafluoroethylene–Ethylene Copolymers. In
Encyclopedia of Polymer Science and Technology, John Wiley & Sons, Inc.: 2002;
http://doi.org/10.1002/0471440264.pst419.pub2
Gangal, S. V.; Brothers, P. D., Perfluorinated Polymers, Tetrafluoroethylene–Perfluorovinyl Ether
Copolymers. In Encyclopedia of Polymer Science and Technology, John Wiley & Sons, Inc.: 2002;
http://doi.org/10.1002/0471440264.pst418.pub2
Banks, R. E., Smart, B.E., Tatlow, J.C. , Organofluorine Chemistry: Principles and Commercial
Applications. In Plenum, New York, NY USA, 1994;
Scheirs, J. e., Modern Fluoropolymers - High Performance Polymers for Diverse Applications. Wiley.
ISBN 0-471-97055-7: 1997.
Ameduri and Sawada, 2017. Fluorinated Polymers. Volume 2: Applications. Royal Society of Chemistry.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
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14. Fluoroelastomers37
Key publications: Worm, A. T.; Gorrtaert, W., Fluorocarbon Elastomers. Encyclopedia of
Polymer Science & Engineering 2015. https://doi.org/10.1002/0471440264.pst137
Améduri, B.; Boutevin, B.; Kostov, G., Fluoroelastomers: Synthesis, properties andapplications. Progress in Polymer Science (Oxford) 2001, 26, (1), 105-187.
https://www.sciencedirect.com/science/article/pii/S0079670000000447?via%3Dihub.

Chemical Information & Inherent Properties
Identification and Terminology
Name

Fluorocarbon elastomers

Fluorinatedpolyphosphazenes

Fluorocarbonmodified silicones

Other Names
Acronym

FKM

General structures(exemplary)

Copolymers of VDF (C2H2F2) &HFP (C3F6)
Terpolymers of VDF, HFP & TFE(C2F4)
Terpolymers of VDF, TFE & PMVE
(C3F6O) [19]Schematic overview(adapted from [2])Fluorosilicones

FLS

PNF elastomers

TFE

+

+

+

VDF

Propene

PMVE

+

+

HFP

fct. comonomer

+

+

+

Cure package

Cure package

Cure package

↓

↓

↓

FKM

FEPM

FFKM

Acronyms: TFE = Tetrafluoroethylene; VDF = Vinylidene fluoride; HFP = Hexafluoropropylene; FKM = fluorocarbon elastomers;
FEPM = Tetrafluoroethylene propylene; PMVE = Perfluoromethylvinylether; FFKM = perfluoro-elastomers

37

Fluoroelastomers are also fluoropolymers, but have rather different physical and chemical
properties from those presented in the previous fact card on fluoropolymers. Therefore, they are
made into a separate fact card here.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

88  ENV/CBC/MONO(2022)1
Degradability, Mobility, Bioconcentration
Stability

Mostly resistant towards light, ozone,
heat, solvents, aggressive chemicals,
and combinations thereof. Heat
resistant until 250 °C. In general,stability increases with fluorine
content. [3]FKM is more susceptible to alkalinedegradation, e.g. FKM was found todegrade slowly (>12 weeks) in a
warm alkaline environment (10%
NaOH, 80 °C). [4], [5]Some “base-resistant” FKMs and
FEPM resist degradation in high pH
environments.38

Inert under normal
conditions, but
decompose at extreme
pH-values or at hightemperatures, in whichcase toxic fluorinatedcompounds such as
3,3,3-trifluoropropionaldehyde areproduced. [6]Depolymerization
occurs attemperatures above
300 °C. Fluorinatedpolyphosphazenes arevery resistant to
combustion. [7]Main Synthesis
MethodHigh-pressure, free-radical aqueous
emulsion polymerization, withorganic or inorganic peroxycompounds as initiators.
Fluorosurfactants (or non-fluorinatedsurfactants) can be added as
emulsifiers, and ethyl acetate,methanol, acetone, or others can beused as chain-transfer agents. For
curing, bisphenol cross-linking
agents are added as well as a cureaccelerator, such as
triphenylbenzylphosphonium
chloride. [1], [8]Base-catalyzed ringopening
polymerization of
cyclic trimers,
obtained throughhydrolysis of thecorresponding
dichlorosilane. [1]First, ring-opening
polymerization of thecyclic trimer(NPCl2)3 or living
cationic condensation
polymerization of aphosphoranimine
yields poly(dichlorophosphazene). In asecond step, chlorine
is replaced withfluoro-organic sidegroups. [7]Possible Impurities

Residues of processing aids canpotentially remain in the final
product.

Synthesis

Industrial Practices & Commercial Uses
Major Commercial Products
Production/Import
volumes

Total fluoroelastomers consumption globally: approximately 10 000 t/yr as of 2001,
40% of which in the US, 30% in Europe, 20% in Japan, and 10% in Asia-Pacific (excl.
Japan). [8]Name(s)1,1-difluoroethylen-hexafluoropropene polymer /polyvinylidenefluoride/hexafluoropropene [9], [10]Vinylidene fluoride-hexafluoropropylene copolymer [16]CAS Number

9011-17-0

Trade Name(s)DAI-EL; Dyneon; Tecnoflon, Viton

Use

O-ring and oil seal applications in high-heat environments [17]38

According to information provided by representatives of the manufacturing industry.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

ENV/CBC/MONO(2022)1  89

Name(s)Vinylidene fluoride-hexafluoropropylene-tetrafluoroethylene terpolymer
Poly(TFE-ter-VDF-ter-PMVE)CAS Number

25190-89-0

Trade Name(s)Viton GLT [12] DAI-EL; Dyneon; Tecnoflon; Viton

Use

Transfer or compression molded automotive fuel, chemical, and petroleum industry seals[13]. Extruding fuel tubing and hose [20].

Name(s)Vinylidene fluoride-tetrafluoroethylene-perfluorovinyl methyl ether terpolymer
Poly(TFE-ter-PMVE-ter-VDF)

CAS Number

56357-87-0

Trade Name(s)DAI-EL LT [17], Tecnoflon-PL [12]; Viton GLT [12]UseO-rings, seals, gaskets used in the automotive, aerospace, and energy industries. [14]Name(s)Fully fluorinated copolymers of tetrafluoroethylene and a perfluoroalkyl vinyl ether
Poly(TFE-ter-PMVE-ter-8CNVE)

Trade Name(s)DAI-EL Perfluor [17]; Kalrez [12]; Tecnoflon PFR, PFR-HT, PFR-LT

Composition

Perfluorinated rubbers of polymethylene type having all fluoro, perfluoroalkyl or
perfluoroalkoxy substituent groups on the polymer chain (e.g. TFE and PMVE).

Use

O-rings, seals, gaskets used in the automotive, aerospace, and energy industries. [14]O-rings, seals, gaskets and tubing used in the semiconductor processing industry [17]Names(s)Copolymers of tetrafluroethylene and propylene [18]Trade names(s)

Aflas

Use

O-rings, seals, gaskets and wire covering for the oil and gas, chemical process, industrial
equipment, food handling, pharmaceutical, heavy duty diesel and automotive industries.
[18]

Name(s)1-Propene, 1,1,2,3,3,3-hexafluoro-, polymer with 1,1,1,2,2,3,3-heptafluoro-3-((1,2,2trifluoroethenyl)oxy)propane and 1,1,2,2-tetrafluoroethene

CAS Number

63654-41-1

Use

Wire coating and small diameter transparent tubing. [12]Uses
Major applications

Mainly in ground transportation, i.e.
engine oil seals, fuel systemcomponents, and drive-train seals.
Also in the aerospace industry, inindustrial hydraulic and pneumatic
applications as well as the chemical
processing industry andsemiconductor manufacturing. [8],[15]

Fuel-resistantelastomers, antigraffiti and antifouling
coatings, siliconepressure-sensitiveadhesive releaseliners. [6]Fibers andnanofibers, impactabsorbing elastomers,
surface coatings (e.g.
ice-phobic coatings
on helicopter rotor
blades, coatings forbiomedical devices),as radiation resistantpolymers. [7]Knowledge gaps

- Specific production volumes are not publicly available.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

90  ENV/CBC/MONO(2022)1- Environmental monitoring data are not available for these compounds.
- Limited information is available regarding chemical identities of commercial products (including
molecular weight range, molar ratio and composition of monomer units, impurity content, functionalgroups) and their life cycle, including possible releases of low molecular weight compounds.
References
[1]
[2]

[3]
[4]

[5]
[6]

[7]
[8]
[9]
[10]

[11]

[12]
[13]
[14]
[15]
[16]
[17]
[18]
[19]
[20]

J. G. Drobny, Technology of Fluoropolymers, Second. Boca Raton, London, New York: CRC Press,
Taylor & Francis Group, 2009.
K. Hintzer, and W. Schwertfeger, “Fluoropolymers – Environmental Aspects,” in Handbook of
Fluoropolymer Science and Technology, D. W. Smith, S. T. Iacono, and S. S. Iyer, Eds. Hoboken, NJ,
USA: John Wiley & Sons, Inc., 2014
H. Schroeder, “Fluorocarbon Elastomers,” in Rubber Technology, M. Morton, Ed. Dordrecht: Springer
Netherlands, 1999, pp. 410–437.
S. Mitra, A. Ghanbari-Siahkali, P. Kingshott, K. Almdal, H. Kem Rehmeier, and A. G. Christensen,“Chemical degradation of fluoroelastomer in an alkaline environment,” Polym. Degrad. Stab., vol. 83,
no. 2, pp. 195–206, Feb. 2004.
R. E. Banks, B. E. Smart, and J. C. Tatlow, Eds., Organofluorine Chemistry. Principles and Commercial
Applications. New York: Springer Science + Business Media, LLC, 1994.
M. J. Owen, “Fluorosilicones,” in Advances in Silicones and Silicone-Modified Materials, S. J. Clarson,
M. J. Owen, S. D. Smith, and M. E. Van Dyke, Eds. Washington DC: American Chemical Society, 2010,
pp. 99–108.
H. R. Allcock, “Fluorinated Polyphosphazenes,” in Handbook of Fluoropolymer Science andTechnology, Hoboken, NJ, USA: John Wiley & Sons, Inc., 2014, pp. 1–20.
A. T. Worm and W. Grootaert, “Fluorocarbon Elastomers,” in Encyclopedia of Polymer Science andTechnology, Hoboken, NJ, USA: John Wiley & Sons, Inc., 2001, pp. 577–590.
DuPont Performance Elastomers, “Material Safety Data Sheet Viton ® fluoroelastomer.” 2008.
European Chemicals Agency (ECHA), “1,1-Difluoretylen-hexafluorpropenpolymer - Substance
Information.”[Online].
Available:
https://echa.europa.eu/substance-information//substanceinfo/100.111.540. [Accessed: 30-Jan-2020].
Parchem, “Vinylidene fluoride/hexafluoropropylene copolymer supplier distributor- CAS 9011-17-0.”[Online]. Available: https://www.parchem.com/chemical-supplier-distributor/Vinylidene-fluoridehexafluoropropylene-copolymer-042485.aspx. [Accessed: 01-Feb-2020].
Z. Wang, G. Goldenman, T. Tugran, A. McNeil, and M. Jones, “Per- and polyfluoroalkylether
substances: identity, production and use,” 2019.
Chemours, “Viton Fluorelastomers Selection Guide,” 2017.
“Tecnoflon® Fluoroelastomers & Perfluoroelastomers | Solvay.” [Online]. Available:
https://www.solvay.com/en/brands/tecnoflon-fkm-pfr-ffkm. [Accessed: 01-Feb-2020].
J. Gardiner, “Fluoropolymers: Origin, Production, and Industrial and Commercial Applications,” Aust.
J. Chem., vol. 68, no. 1, p. 13, 2015.
Daikin America, “Safety Data Sheet DAI-EL G-701, 702, 704, 751, 752,755,” 2016
“Fluoroelastomers,” Daikin-America. [Online]. Available: https://daikin-america.com/fluoroelastomers/[Accessed: 27-Nov-2020].
Asahi Glass Corporation, “Aflas Fluoroelastomers Product Information Sheet,” 2013
D.L. Hertz, Jr., “Fluoroelastomers” in Basic Elastomer Technology, K.C. Baranwal and H.L. Stevens,
Akron, Rubber Division, American Chemical Society, 2001, pp 483-497.
Daikin Industries, Ltd., DAI-EL Handbook, Osaka, 2016, pp 55-61.

Additional references:

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

ENV/CBC/MONO(2022)1  91

Améduri, B.; Boutevin, B.; Kostov, G., Fluoroelastomers: Synthesis, properties and applications.
Progress in Polymer Science (Oxford) 2001, 26, (1), 105-187. Fluoroelastomers: synthesis, properties
and applications - ScienceDirect.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

92  ENV/CBC/MONO(2022)1

15. Perfluoropolyethers
Key publications: Moffett, et al., Perfluoroalkylpolyethers. In Synthetics, Mineral Oils,
and Bio-Based Lubricants. Chemistry and Technology, Rudnick, L. R., Ed. Taylor &Francis, 2020. https://doi.org/10.1201/9781315158150.

Chemical Information & Inherent Properties
Identification and Terminology
Name

Perfluoropolyethers

Acronym

PFPEs

An example ofgeneral structure(linear isomer
examples) [1]Note: monomer units distributed randomly along the polymer backbone. In different
PFPEs, different monomer units may present.
Degradability, Mobility, Bioconcentration
Stability

Thermally stable, non-flammable, chemically resistant, resistant to ionizing radiation,
non-volatile (up to 350 °C) [2]Synthesis
Main Synthesis
MethodAnionic ring opening polymerization or UV-catalysed radical oxopolymerization (e.g.
copolymerization of tetrafluoroethylene with O2) [1], [2]Industrial Practices & Commercial Uses
Major Commercial ProductsName(s)Poly[oxy[trifluoro(trifluoromethyl)-1,2-ethanediyl]], α-(1,1,2,2,2-pentafluoroethyl)-ω[tetrafluoro(trifluoromethyl)ethoxy]-

Trade Name(s)Krytox PFPE High Performance Lubricant (60–100% of total product), Krytox Sodium
Nitrite Inhibited PFPE/PTFE Greases (71–80% of total product) [3]Chemical Formula–[OCF(CF3)CF2OCF(CF3)CF2OCF(CF3)CF2]–

CAS Number

60164-51-4

Use

Nonflammable, stable and inert lubricant for applications in the aerospace and nuclear
industries. [4]Name(s)Diphosphoric acid, polymers with ethoxylated reduced methyl esters of reduced
polymerized oxidized tetrafluoroethylene

Trade Name(s)Possibly Fomblin HC/P2-1000 [3]CAS Number

200013-65-6

Use

Lubricant, and water and oil repellent in paper products and food packaging. [3]Production/Import
volumes

Produced or imported in volumes of over 11 340 kg in the US.
Estimated value of dutiable imports to the US by 2017: 13 000 000 $ [3]

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

ENV/CBC/MONO(2022)1  93

Name(s)1-Propene, 1,1,2,3,3,3-hexafluoro-, oxidized, polymd.

Trade Name(s)Fomblin Y (also in Fomblin HC, Fomblin Y LVAC, Galden HT-90 Assay, Solkatherm
SES 36) [3]Chemical Formula–[CF(CF3)CF2OCF2CF(CF3)CF2OCF2CF(CF3)CF2OCF2]–

CAS Number

69991-67-9

Use

As a lubricant, welding and soldering agent, and in personal care products (cosmetics)[3]

Production/Import
volumes

0.5 tonnes used in Sweden in 2017
0.3 tonnes used in Denmark in 2016 [3]Name(s)Ethene, 1,1,2,2-tetrafluoro-, oxidized, polymd.

Trade Name(s)Fomblin Z60, Fomblin Z-15, FOMBLINCR 862 (50 - 55% of total product) [3]

CAS Number

69991-61-3

Name(s)

Tetrafluoroethylene, oxidized, oligomers, reduced, methyl esters, reduced, reaction
products with ethylene oxide

Trade Name(s)Fluorolink E10-H

CAS Number

162492-15-1

Use

Non-stick coating [3]Name(s)Hexafluoropropene, oxidized, oligomers, reduced and hydrolyzed

Trade Name(s)Carbaflo XTR S5 F80 (1–2,4% of total weight) [3]

CAS Number

161075-14-5

Use

Lubricant used in automotive industry, also corrosion inhibitor and used in surface
treatment applications effective in sub-zero temperatures. [3]Production/Import
volumes

Estimated value of dutiable imports to the US by 2017: 2 000 000 $ [3]Trade Name(s)Fluorolink AD1700

Chemical Formula

XCF2O-(CF2CF2O)m(CF2O)n-CF2X where X = CH2OCOCH=CH2

Use

Used as additive for coatings, in battery systems and smart devices [3]Trade Name(s)Optool DSX

Chemical Formula

CF3CF2CF2O-(CF2CF2CF2O)n-CF2CF2X where X = CH2CH2Si(OR)3Use

Used in anti-smudge coatings [3]Uses
Major applications

Mainly high performance lubricants for engines and machinery [2], but also as surface
treatments for natural stone, metal, glass, plastic, textiles, leather, and paper, as well as
paperboard treatment for food-contact applications [1].

Knowledge gaps

- Production and use volumes are not publicly available.
- Environmental fate and monitoring data are not available for these compounds.

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

94  ENV/CBC/MONO(2022)1- Limited information is available regarding chemical identities of commercial PFPE products (including
molecular weight range, molar ratio and composition of monomer units, impurity content, functionalgroups) and their life cycle (including releases and degradation).
References
[1]
[2]
[3]
[4]

R. C. Buck et al., “Perfluoroalkyl and polyfluoroalkyl substances in the environment: Terminology,
classification, and origins,” Integr. Environ. Assess. Manag., vol. 7, no. 4, pp. 513–541, Oct. 2011.
J. Gardiner, “Fluoropolymers: Origin, Production, and Industrial and Commercial Applications,” Aust.
J. Chem., vol. 68, no. 1, p. 13, 2015.
Z. Wang, G. Goldenman, T. Tugran, A. McNeil, and M. Jones, “Per- and polyfluoroalkylether
substances: identity, production and use,” 2019.
“Krytox Lubricants | High Performance Greases & Oils | PFPE,” Miller-Stephenson. [Online]. Available:
https://miller-stephenson.com/krytox/. [Accessed: 31-Jan-2020].

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

ENV/CBC/MONO(2022)1  95

Annex A. List of PFASs Included in the Fact Cards, Their Acronyms, CAS
Registry Numbers (CASRNs), DTXSIDs and Fact Card Location

Full name

Acronym/
Trade name

Phosphinic acid, P,P-bis(1,1,2,2,3,3,4,4,4nonafluorobutyl)-;Bis(nonafluorobutyl)phosphinic acid

C4/C4-PFPIA /Tivida FL 2100

A mixture of perfluoroalkyl phosphonic andphosphinic acids

Masurf-780

Phosphonic acid, perfluoro-C6–12-alkyl derivs.

CASRN

DTXSIDs39

Fact
card

52299-25-9

DTXSID605
56851

#1

DTXSID801
027192#1

DTXSID808
82003

#1

68412-68-0

Phosphinic acid, bis(perfluoro- C6–12-alkyl) derivs.;
Phosphinic acid, bis(perfluoro- C6–12-alkyl)
derivatives (C6–12 PFPIAs)(C6–C12PFPIAs)

68412-69-1

Phosphonic acid, P-(1,1,2,2,3,3,4,4,5,5,6,6,6tridecafluorohexyl)-;
Perfluorohexyl phosphonic acid

C6-PFPA40143-76-8

DTXSID908
80439

#1

Phosphonic acid, P(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8heptadecafluorooctyl)-;
Perfluorooctyl phosphonic acid

C8-PFPA40143-78-0

DTXSID808
79832

#1

Phosphonic acid, P(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10heneicosafluorodecyl)-;
Perfluorodecyl phosphonic acid

C10-PFPA

52299-26-0#1

Phosphinic acid, P(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8heptadecafluorooctyl)-P-(1,1,2,2,3,3,4,4,5,5,6,6,6tridecafluorohexyl)-;(Perfluorohexyl) (perfluorooctyl) phosphinic acid

C6/C8-PFPIA

610800-34-5#1

Phosphinic acid, P,Pbis(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8heptadecafluorooctyl)-;Bis(perfluorooctyl) phosphinic acid

C8/C8-PFPIA

40143-79-1#1

Phosphinic acid, P,P-bis(1,1,2,2,3,3,4,4,5,5,6,6,6tridecafluorohexyl)-;Bis(perfluorohexyl) phosphinic acid

C6/C6-PFPIA

40143-77-9

#1

39

#1

DTXSID = Distributed Structure-Searchable Toxicity Database (DSSTox) substance ID

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

96  ENV/CBC/MONO(2022)1
Phosphinic acid, P(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10heneicosafluorodecyl)-P-(1,1,2,2,3,3,4,4,5,5,6,6,6tridecafluorohexyl)-;(Perfluorohexyl) (perfluorodecyl) phosphinic acid

C6/C10-PFPIA

1240600-401#1Phosphinic acid, P(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10heneicosafluorodecyl)-P(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8heptadecafluorooctyl)- ;(Perfluorooctyl) (perfluorodecyl) phosphinic acid

C8/C10-PFPIA

500776-81-8#1(Perfluorohexyl) (perfluorododecyl) phosphinicacid

C6/C12-PFPIA

Octanoic acid, 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8pentadecafluoro-, ammonium salt (1:1);
Ammonium perfluorooctanoate

APFO

3825-26-1

DTXSID803
7708#2

Nonanoic acid, 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9heptadecafluoro-, ammonium salt (1:1);
Ammonium perfluorononanoate

APFN

4149-60-4

DTXSID208
80205

#2

Ammonium henicosafluoroundecanoate;
Ammonium perfluoroundecanoate

APFUnD

4234-23-5

DTXSID208
97176

#2

Ammonium pentacosafluorotridecanoate;
Ammonium perfluorotridecanoate

APFTrD

Fatty acids, C7–13, perfluoro, ammonium salts

Surflon® S-111

72968-38-8

DTXSID801
04590

#2

Acetic acid, 2,2,2-trifluoro-;
Trifluoro acetic acidTFA

76-05-1DTXSID904
1578#2

Propanoic acid, 2,2,3,3,3-pentafluoro-;
Perfluoropropionic acidPFPrA

422-64-0

DTXSID805
9970#2

Butanoic acid, 2,2,3,3,4,4,4-heptafluoro-;
Perfluorobutanoic acid;
Heptafluorobutyric acidPFBA375-22-4

DTXSID405
9916#2

Pentanoic acid, 2,2,3,3,4,4,5,5,5-nonafluoro-;
Perfluoropentanoic acid;
Perfluorovaleric acid

PFPeA

2706-90-3

DTXSID606
2599#2

Hexanoic acid, 2,2,3,3,4,4,5,5,6,6,6-undecafluoro-;
Perfluorohexanoic acid

PFHxA

307-24-4

DTXSID303
1862#2

Heptanoic acid, 2,2,3,3,4,4,5,5,6,6,7,7,7tridecafluoro-;
Perfluoroheptanoic acid

PFHpA

375-85-9

DTXSID103
7303#2

Octanoic acid, 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8pentadecafluoro-;
Perfluorooctanoic acid

PFOA

335-67-1

DTXSID803
1865

#2

#1

#2

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

ENV/CBC/MONO(2022)1  97

Nonanoic acid, 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9heptadecafluoro-;
Perfluorononanoic acidPFNA375-95-1

DTXSID803
1863#2

Decanoic acid,
2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10nonadecafluoro-;
Perfluorodecanoic acidPFDA335-76-2

DTXSID303
1860#2

Undecanoic acid,
2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11heneicosafluoro-;
Perfluoroundecanoic acid

PFUnDA

2058-94-8

DTXSID804
7553#2

Dodecanoic acid,
2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12tricosafluoro-;
Perfluorododecanoic acid

PFDoDA

307-55-1

DTXSID803
1861#2

Tridecanoic acid,
2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,
13,13-pentacosafluoro-;
Perfluorotridecanoic acid

PFTrDA

72629-94-8

DTXSID908
68151

#2

Tetradecanoic acid,
2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,
13,14,14,14-heptacosafluoro-;
Perfluorotetradecanoic acid

PFTeDA

376-06-7

DTXSID305
9921#2

Pentadecanoic acid,
2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,
13,14,14,15,15,15-nonacosafluoro-;
Perfluoropentadecanoic acid

PFPeDA

141074-63-7

DTXSID308
93341

#2

Hexadecanoic acid,
2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,
13,14,14,15,15,16,16,16-hentriacontafluoro-;
Perfluorohexadecanoic acid

PFHxDA

67905-19-5

DTXSID107
0800#2

Heptadecanoic acid,
2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,
13,14,14,15,15,16,16,17,17,17-tritriacontafluoro-;
Perfluoroheptadecanoic acid

PFHpDA

57475-95-3

DTXSID608
96623

#2

Octadecanoic acid,
2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,
13,14,14,15,15,16,16,17,17,18,18,18pentatriacontafluoro-;
Perfluorooctadecanoic acid

PFOcDA

16517-11-6

DTXSID106
6071#2

Eicosanoic acid,
2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,
13,14,14,15,15,16,16,17,17,18,18,19,19,20,20,20nonatriacontafluoro-;
Perfluoroeicosanoic acid

PFEiDA

68310-12-3

DTXSID908
87327

#2

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

98  ENV/CBC/MONO(2022)1
1-Butanesulfonic acid, 1,1,2,2,3,3,4,4,4-nonafluoro, potassium salt (1:1);
Potassium perfluorobutanesulfonate

K-PFBS

29420-49-3

DTXSID303
7707#3

1-Butanesulfonic acid, 1,1,2,2,3,3,4,4,4-nonafluoro;
Perfluorobutanesulfonic acidPFBS375-73-5

DTXSID5030030#3

1-Pentanesulfonic acid, 1,1,2,2,3,3,4,4,5,5,5undecafluoro-;
Perfluoropentanesulfonic acidPFPeS

2706-91-4

DTXSID806
2600#3

1-Hexanesulfonic acid, 1,1,2,2,3,3,4,4,5,5,6,6,6tridecafluoro-;
Perfluorohexanesulfonic acid

PFHxS

355-46-4

DTXSID704
0150#3

1-Heptanesulfonic acid,
1,1,2,2,3,3,4,4,5,5,6,6,7,7,7-pentadecafluoro-;
Perfluoroheptanesulfonic acid

PFHpS

375-92-8

DTXSID805
9920#3

1-Octanesulfonic acid,
1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-;
Perfluorooctanesulfonic acid

PFOS

1763-23-1

DTXSID303
1864#3

1-Nonanesulfonic acid,
1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9nonadecafluoro-;
Perfluorononanesulfonic acid

PFNS

68259-12-1

DTXSID807
1356#3

1-Decanesulfonic acid,
1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10heneicosafluoro-;
Perfluorodecanesulfonic acidPFDS

335-77-3

DTXSID304
0148#3

1-Octanesulfinic acid,
1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-;
Perfluorooctane sulfinic acid

PFOSI

647-29-0

DTXSID109
04262

#3

Ethanesulfonic acid, 2-[(6-chloro1,1,2,2,3,3,4,4,5,5,6,6-dodecafluorohexyl)oxy]1,1,2,2-tetrafluoro-, potassium salt (1:1);
Potassium 9-chlorohexadecafluoro-3-oxanonane-1sulfonate

F-53B / 6:2 ClPFESA

73606-19-6

DTXSID608
81236

#4

Propanoic acid, 2,3,3,3-tetrafluoro-2-(1,1,2,2,3,3,3heptafluoropropoxy)-, ammonium salt (1:1);
Hexafluoropropylene oxide-dimer acid, ammonium
salt

GenX /PFPrOPrA,
HFPO-DA (acidform)

62037-80-3

DTXSID401
08559

#4

Propanoic acid, 2,2,3-trifluoro-3-[1,1,2,2,3,3hexafluoro-3-(trifluoromethoxy)propoxy]-,ammonium salt (1:1);
3H-Perfluoro-3-[(3-methoxy-propoxy)propanoicacid], ammonium salt

ADONA

958445-44-8

DTXSID008
74026

#4

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

ENV/CBC/MONO(2022)1  99

Acetic acid, 2,2-difluoro-2-[[2,2,4,5-tetrafluoro-5(trifluoromethoxy)-1,3-dioxolan-4-yl]oxy]-,ammonium salt (1:1);
Perfluoro{acetic acid, 2-[(5-methoxy-1,3-dioxolan4-yl)oxy]}, ammonium salt

F-DIOX
ammonium salt;
cC6O4
ammonium salt

1190931-271

DTXSID008
82626

#4

Propanoyl fluoride, 2,3,3,3-tetrafluoro-2[1,1,2,3,3,3-hexafluoro-2-(1,1,2,2,3,3,3heptafluoropropoxy)propoxy]-;
Hexafluoropropene oxide trimer

HFPO-TA

2641-34-1

DTXSID2044630#4

2-(4-chloro-1,1,2,2,3,3,4,4-octafluorobutoxy)1,1,2,2-tetrafluoroethane-1-sulfonic acid

4:2 Cl-PFESA

737728-96-0

2-[(8-Chloro-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8hexadecafluorooctyl)oxy]-1,1,2,2tetrafluoroethanesulfonic acid

8:2 Cl-PFESA

763051-92-9

2-((1,1,2,2,3,3,4,4,5,5,6,6-dodecafluorohexyl)oxy)1,1,2,2-tetrafluoroethane-1-sulfonic acid6:2 H-PFESA

874280-03-2

Butanoyl fluoride, 2,2,3,3,4,4,4-heptafluoro-;
Perfluorobutanoyl fluoride

PBCF

335-42-2

DTXSID004
1696#5

Octanoyl fluoride, 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8pentadecafluoro-;
Perfluorooctanoyl fluoride

POCF

335-66-0

DTXSID005
9829#5

154380-34-4

DTXSID808
93356

#5

89685-56-3

DTXSID504
78336

#5

Hexanamide, 2,2,3,3,4,4,5,5,6,6,6-undecafluoro-N[3-(trimethoxysilyl)propyl]-;N-[3-(trimethoxysilyl)propyl]-perfluorohexanamide#4
DTXSID408
92507

#4

#4

Octanamide, 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8pentadecafluoro-N-methyl-;N-methylperfluorooctanamide

MeFOA

N-ethylperfluorooctanamide

EtFOA

#5

N-ethylperfluorobutanamide

EtFBA

#5

1-Octanesulfonyl fluoride,
1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-;
Perfluorooctanesulfonyl fluoride

POSF

307-35-7

DTXSID502
7140#6

1-Butanesulfonyl fluoride, 1,1,2,2,3,3,4,4,4nonafluoro-;
Perfluorobutanesulfonyl fluoride

PBSF

375-72-4

DTXSID208
61913

#6

1-Octanesulfonamide, N-ethyl1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-;
N-Ethylperfluorooctanesulfonamide

Sulfluramid
EtFOSA

4151-50-2

DTXSID103
2646#6

Sodium 2-(N-ethylperfluorooctane-1sulfonamido)ethyl phosphate;
perfluorooctane sulfonamido ethanol-based
phosphate diester

SAmPAP

1-Octanesulfonamide,
1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-;
Perfluorooctanesulfonamide

FOSA

#6

754-91-6

DTXSID303
8939#6

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

100  ENV/CBC/MONO(2022)1
1-Octanesulfonamide,
1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-Nmethyl-;N-methyl perfluorooctane sulfonamide

MeFOSA

31506-32-8

DTXSID1067629#6

1-Octanesulfonamide,
1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-N(2-hydroxyethyl)-N-methyl-;N-methyl perfluorooctane sulfonamidoethanol

MeFOSE

24448-09-7

DTXSID702
7831#61-Octanesulfonamide, N-ethyl1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-N(2-hydroxyethyl)-;N-ethyl perfluorooctane sulfonamidoethanol

EtFOSE

1691-99-2

DTXSID602
7426#6

1-Butanesulfonamide, 1,1,2,2,3,3,4,4,4-nonafluoroN-methyl-;N-methyl perfluorobutane sulfonamide

MeFBSA

68298-12-4

DTXSID107
1373#6

1-Butanesulfonamide, 1,1,2,2,3,3,4,4,4-nonafluoroN-(2-hydroxyethyl)-N-methyl-;N-methyl perfluorobutane sulfonamidoethanol

MeFBSE

34454-97-2

DTXSID006
7848#6

1-Octanesulfonic acid, 3,3,4,4,5,5,6,6,7,7,8,8,8tridecafluoro-;
6:2 Fluorotelomer sulfonic acid

27619-97-2

DTXSID606
7331#7

1-Propanaminium, N-(carboxymethyl)-N,Ndimethyl-3-[[(3,3,4,4,5,5,6,6,7,7,8,8,8tridecafluorooctyl)sulfonyl]amino]-, inner salt;
6:2 Fluorotelomer sulfonamide betaine

34455-29-3

DTXSID404
1284#7

Silane, triethoxy(3,3,4,4,5,5,6,6,7,7,8,8,8tridecafluorooctyl)-;
Triethoxy(3,3,4,4,5,5,6,6,7,7,8,8,8tridecafluorooctyl)silane

51851-37-7#7

1-Octanol, 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-;
6:2 Fluorotelomer alcohol;
2-(perfluorohexyl)ethanol;
1H,1H,2H,2H-perfluorooctan-1-ol

6:2 FTOH

647-42-7

DTXSID504
4572#7

1-Decanol, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10heptadecafluoro-;
8:2 Fluorotelomer alcohol;
2-(perfluorooctyl)ethanol;
1H,1H,2H,2H-Perfluorodecan-1-ol

8:2 FTOH

678-39-7

DTXSID702
9904#7

1-Dodecanol,
3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12heneicosafluoro-;
10:2 Fluorotelomer alcohol;
2-(perfluorodecyl)ethanol;
1H,1H,2H,2H-perfluorododecan-1-ol

10:2 FTOH

865-86-1

DTXSID202
9905#7

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

ENV/CBC/MONO(2022)1  101

1-Hexanesulfonic acid, 3,3,4,4,5,5,6,6,6nonafluoro-;
4:2 Fluorotelomer sulfonic acid;
1H,1H,2H,2H-perfluorohexanesulphonic acid

4:2 FTSA

757124‐72‐4

DTXSID308
91564

#7

1-Octanesulfonic acid, 3,3,4,4,5,5,6,6,7,7,8,8,8tridecafluoro-;
6:2 Fluorotelomer sulfonic acid;
1-Octanesulfonic acid, 3,3,4,4,5,5,6,6,7,7,8,8,8tridecafluoro-

6:2 FTSA

27619-97-2

DTXSID606
7331#7

1-Decanesulfonic acid,
3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10heptadecafluoro-;
8:2 Fluorotelomer sulfonic acid;
3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10heptadecafluorodecanesulphonic acid

8:2 FTSA

39108-34-4

DTXSID001
92353

#7

1-Octanol, 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-,
1,1'-(hydrogen phosphate);
6:2 Fluorotelomer phosphate diester;Bis[2-(perfluorohexyl)ethyl]phosphate

6:2 diPAP

57677-95-9

DTXSID505
61590

#7

1-Decanol, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10heptadecafluoro-, 1,1'-(hydrogen phosphate);
8:2 Fluorotelomer phosphate diester;Bis[2-(perfluorooctyl)ethyl]phosphate

8:2 diPAP

678-41-1

DTXSID902
18051

#7

1-Dodecanol,
3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12heneicosafluoro-, 1,1'-(hydrogen phosphate);
10:2 Fluorotelomer phosphate diester;Bis[2-(perfluorodecyl)ethyl]phosphate
3,3,4,4,5,5,6,6,7,7,7-Undecafluoro-2-heptanol; 5:2
fluorotelomer secondary alcohol

10:2 diPAP

1895-26-7

DTXSID301
72360

#7

5:2 sFTOH(secondary
alcohol,[F(CF2)5CH(OH)CH3]),

914637-05-1

DTXSID805
97206

#7

4:2 Fluorotelomer unsaturated carboxylic acid

4:2 FTUCA

70887-90-0#72-Octenoic acid, 3,4,4,5,5,6,6,7,7,8,8,8dodecafluoro-;
6:2 Fluorotelomer unsaturated carboxylic acid;
2H-perfluoro-2-octenoic acid

6:2 FTUCA

70887-88-6#7

8:2 Fluorotelomer unsaturated carboxylic acid;2-Decenoic acid, 3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10hexadecafluoro-

8:2 FTUCA

70887-84-2

DTXSID608
25615

#7

2-Dodecenoic acid,
3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12eicosafluoro-;
10:2 Fluorotelomer unsaturated carboxylic acid;
2H-perfluoro-2-dodecenoic acid

10:2 FTUCA

70887-94-4

DTXSID708
95723

#7

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

102  ENV/CBC/MONO(2022)1
2-Propenoic acid,
3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10heptadecafluorodecyl ester;
1H,1H,2H,2H-perfluorodecyl acrylate

8:2 FTAc

27905-45-9

DTXSID506
7348#7

1-Butanol, 2,2,3,3,4,4,4-heptafluoro-;(Perfluoropropyl)methanol

3:1 FTOH / RM
610

375-01-9

DTXSID405
9914#853515-73-4

DTXSID308
80458

#8

2-Propenoic acid, 2-methyl-,
2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctyl
ester, polymer with 2-propenoic acid
Oxirane, 2,2,3-trifluoro-3-(trifluoromethyl)-;Hexafluoropropylene oxide /Trifluoro(trifluoromethyl)oxirane

HFPO

428-59-1

DTXSID602
9177#9

Furan, 2,2,3,3,4,4,5-heptafluorotetrahydro-5(1,1,2,2,3,3,4,4,4-nonafluorobutyl)-;
Perfluoro-2-butyltetrahydrofuran

FC-75

335-36-4

DTXSID608
71632

#9

Ethene, tetrafluoro-;
Tetrafluoroethylene

TFE

116-14-3

DTXSID602
1325

#10

Benzenesulfonic acid, 4-[[3,4,4,4-tetrafluoro-2[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-1,3bis(trifluoromethyl)-1-buten-1-yl]oxy]-, sodium salt
(1:1);
Sodium ρ-perfluorous nonenoxybenzene sulfonate

OBS

70829-87-7

DTXSID601
020833#102-Pentenoyl fluoride, 2,3,4,5,5,5-hexafluoro-4(trifluoromethyl)-;
Perfluoro-4-methylpent-2-enoyl fluoride

88022-48-4

DTXSID408
97491

#10

2-Pentene, 1,1,2,3,4,5,5,5-octafluoro-1-iodo-4(trifluoromethyl)-, (E)-;(2E)-1,1,2,3,4,5,5,5-Octafluoro-1-iodo-4(trifluoromethyl)-2-pentene

120695-78-5

DTXSID206
94127

#10

1-Propene, 1,1,2,3,3,3-hexafluoro-;
Hexafluoropropene

HFP

116-15-4

DTXSID202
6949

#10

Ethane, 1,1,1,2-tetrafluoro-;
1,1,1,2-Tetrafluoroethane

HFC-134a /R-134a /Freon 134a /Forane 134a /Genetron 134a /Florasol 134a /Suva 134a /Norflurane811-97-2

DTXSID102
1324

#11

Ethene, 1,1-difluoro-;
1,1-Difluoroethylene;
vinylidene fluoride

VDF

75-38-7DTXSID302
1439

#11

1-Propene, 2,3,3,3-tetrafluoro-;
2,3,3,3-Tetrafluoropropene

HFO-1234yf

754-12-1

DTXSID407
4728

#11

Butane, 1-ethoxy-1,1,2,2,3,3,4,4,4-nonafluoro-;
Ethylnonafluorobutylether

HFE-7200

163702-05-4

DTXSID007
3118

#11

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

ENV/CBC/MONO(2022)1  103

Methane, (difluoromethoxy)trifluoro-;
Pentafluorodimethylether

HFE-1253822-68-2

DTXSID407
3968

#11

Propane, 1,1,1,2,3,3,3-heptafluoro-;
1,1,1,2,3,3,3-heptafluoropropane

HFC-227ea

431-89-0

Propane, 1,1,1,3,3,3-hexafluoro-;
1,1,1,3,3,3-hexafluoropropane

HFC-236fa

690-39-1

DTXSID805
2435

#11

2-Butene, 1,1,1,4,4,4-hexafluoro-, (2Z)-;(Z)-1,1,1,4,4,4-hexafluorobut-2-ene

HFO-1336mzz

692-49-9

DTXSID008
83476

#11

Ethane, 1,1,1,2,2-pentafluoro-;
1,1,1,2,2-pentafluoroethane

HFC-125354-33-6

DTXSID102
4251

#11

Propane, 1,1,1,3,3-pentafluoro-;
1,1,1,3,3-pentafluoropropane

HFC-245fa

460-73-1

DTXSID605
2110

#11

Butane, 1,1,1,3,3-pentafluoro-;
1,1,1,3,3-pentafluorobutane

HFC-365mfc

406-58-6

DTXSID507
3901

#11

Pentane, 1,1,1,2,2,3,4,5,5,5-decafluoro-;
1,1,1,2,2,3,4,5,5,5-decafluoropentane

HFC-43-10mee

138495-42-8

DTXSID308
69884

#11

1-Propene, 1,3,3,3-tetrafluoro-, (1E)-;
1,3,3,3-tetrafluoroprop-1-ene

HFC-1234ze

29118-24-9

DTXSID609
36952

#11

Benzene, (trifluoromethyl)-;Benzotrifluoride

98-08-8

DTXSID202
4589

#12

Benzene, 1-chloro-4-(trifluoromethyl)-;
1-Chloro-4-(trifluoromethyl)benzene

98-56-6

DTXSID702
4821

#12

#11

Benzenepropanamine, N-methyl-γ-[4(trifluoromethyl)phenoxy]-

Fluoxetine

54910-89-3

DTXSID702
3067

#12

Urea, N,N-dimethyl-N′-[3-(trifluoromethyl)phenyl]-

Fluometuron

2164-17-2

DTXSID802
0628

#12

Ethene, 1,1,2,2-tetrafluoro-, homopolymer;
Polytetrafluoroethylene

PTFE

9002-84-0

DTXSID704
7724

#13

Ethene, 1,1-difluoro-, homopolymer;
Polyvinylidene fluoride

PVDF

24937-79-9

DTXSID808
95097

#13

1-Propene, 1,1,2,3,3,3-hexafluoro-, polymer with
1,1,2,2-tetrafluoroethene;
Fluorinated ethylene propylene

FEP

25067-11-2

DTXSID708
80371

#13

Propane, 1,1,1,2,2,3,3-heptafluoro-3-[(1,2,2trifluoroethenyl)oxy]-, polymer with 1,1,2,2tetrafluoroethene;
Perfluoro-3-[(trifluoroethenyl)oxy]propane,
polymer with tetrafluoroethene

26655-00-5

DTXSID408
80383

#13

Ethene, 1,1,2,2-tetrafluoro-, polymer with 1,1,2trifluoro-2-(1,1,2,2,2-pentafluoroethoxy)ethane;
Tetrafluoroethene polymer withtrifluoro(pentaflurorethoxy)ethene31784-04-0

DTXSID108
81948

#13

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified

104  ENV/CBC/MONO(2022)1
1-Propene, 1,1,2,3,3,3-hexafluoro-, polymer with
1,1-difluoroethene;
1,1-Difluorethylene-hexafluorpropene polymer

9011-17-0

DTXSID308
80211

#14

1-Propene, 1,1,2,3,3,3-hexafluoro-, polymer with
1,1,1,2,2,3,3-heptafluoro-3-[(1,2,2trifluoroethenyl)oxy]propane and 1,1,2,2tetrafluoroethene;
Hexafluoropropene, 1-((trifluoroethenyl)oxy)heptafluoropropane, tetrafluoroethene polymer

63654-41-1

DTXSID108
80532

#14

FACT CARDS OF MAJOR GROUPS OF PER- AND POLYFLUOROALKYL SUBSTANCES (PFASS)
Unclassified