Document ID: EPA-HQ-TRI-2016-0222-0001
Agency: epa
Document Type: Proposed Rule
Title: Addition of Nonylphenol Ethoxylates Category: Community Right-to-Know Toxic Chemical Release Reporting
Posted Date: 2016-11-16T05:00Z

[Federal Register Volume 81, Number 221 (Wednesday, November 16, 2016)]
[Proposed Rules]
[Pages 80624-80629]
From the Federal Register Online via the Government Publishing Office [www.gpo.gov]
[FR Doc No: 2016-27547]

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ENVIRONMENTAL PROTECTION AGENCY

40 CFR Part 372

[EPA-HQ-TRI-2016-0222; FRL-9951-01]
RIN 2070-AK15

Addition of Nonylphenol Ethoxylates Category; Community Right-To-
Know Toxic Chemical Release Reporting

AGENCY: Environmental Protection Agency (EPA).

ACTION: Proposed rule.

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SUMMARY: EPA is proposing to add a nonylphenol ethoxylates (NPEs) 
category to the list of toxic chemicals subject to reporting under 
section 313 of the Emergency Planning and Community Right-to-Know Act 
(EPCRA) and section 6607 of the Pollution Prevention Act (PPA). EPA is 
proposing to add this chemical category to the EPCRA section 313 list 
because EPA believes NPEs meet the EPCRA section 313(d)(2)(C) toxicity 
criteria. Specifically, EPA believes that longer chain NPEs can break 
down in the environment to short-chain NPEs and nonylphenol, both of 
which are highly toxic to aquatic organisms. Based on a review of the 
available production and use information, members of the NPEs category 
are expected to be manufactured, processed, or otherwise used in 
quantities that would exceed EPCRA section 313 reporting thresholds.

DATES: Comments must be received on or before January 17, 2017.

ADDRESSES: Submit your comments, identified by Docket ID No. EPA-HQ-
TRI-2016-0222, by one of the following methods:
     Federal eRulemaking Portal: http://www.regulations.gov. 
Follow the online instructions for submitting comments. Do not submit 
electronically any information you consider to be Confidential Business 
Information (CBI) or other information whose disclosure is restricted 
by statute.
     Mail: Document Control Office (7407M), Office of Pollution 
Prevention and Toxics (OPPT), Environmental Protection Agency, 1200 
Pennsylvania Ave. NW., Washington, DC 20460-0001.
     Hand Delivery: To make special arrangements for hand 
delivery or delivery of boxed information, please follow the 
instructions at http://www.epa.gov/dockets/where-send-comments-epa-dockets#hq.
    Additional instructions on commenting or visiting the docket, along 
with more information about dockets generally, is available at http://www.epa.gov/dockets/commenting-epa-dockets.

FOR FURTHER INFORMATION CONTACT: For technical information contact: 
Daniel R. Bushman, Toxics Release Inventory Program Division (7410M), 
Office of Pollution Prevention and Toxics, Environmental Protection 
Agency, 1200 Pennsylvania Ave. NW., Washington, DC 20460-0001; 
telephone number: (202) 566-0743; email: bushman.daniel@epa.gov.
    For general information contact: The Emergency Planning and 
Community Right-to-Know Hotline; telephone numbers: toll free at (800) 
424-9346 (select menu option 3) or (703) 412-9810 in the Washington, DC 
Area and International; or toll free, TDD (800) 553-7672; or go to 
http://www.epa.gov/superfund/contacts/infocenter/.

SUPPLEMENTARY INFORMATION: 

I. General Information

A. Does this notice apply to me?

    You may be potentially affected by this action if you manufacture, 
process, or otherwise use NPEs. The following list of North American 
Industrial Classification System (NAICS) codes is not intended to be 
exhaustive, but rather provides a guide to help readers determine 
whether this document applies to them. Potentially affected entities 
may include:
     Facilities included in the following NAICS manufacturing 
codes (corresponding to Standard Industrial Classification (SIC) codes 
20 through 39): 311 *, 312 *, 313 *, 314 *, 315 *, 316, 321, 322, 323 
*, 324, 325 *, 326 *, 327, 331, 332, 333, 334 *, 335 *, 336, 337 *, 339 
*, 111998 *, 211112 *, 212324 *, 212325 *, 212393 *, 212399 *, 488390 
*, 511110, 511120, 511130, 511140 *, 511191, 511199, 512220, 512230 *, 
519130 *, 541712 *, or 811490 *.
    * Exceptions and/or limitations exist for these NAICS codes.
     Facilities included in the following NAICS codes 
(corresponding to SIC codes other than SIC codes 20 through 39): 
212111, 212112, 212113 (corresponds to SIC code 12, Coal Mining (except 
1241)); or 212221, 212222, 212231, 212234, 212299 (corresponds to SIC 
code 10, Metal Mining (except 1011, 1081, and 1094)); or 221111, 
221112, 221113, 221118, 221121, 221122, 221330 (Limited to facilities 
that combust coal and/or oil for the purpose of generating power for 
distribution in commerce) (corresponds to SIC codes 4911, 4931, and 
4939, Electric Utilities); or 424690, 425110, 425120 (Limited to 
facilities previously classified in SIC code 5169, Chemicals and Allied 
Products, Not Elsewhere Classified); or 424710 (corresponds to SIC code 
5171, Petroleum Bulk Terminals and Plants); or 562112 (Limited to 
facilities primarily engaged in solvent recovery services on a contract 
or fee basis (previously classified under SIC code 7389, Business 
Services, NEC)); or 562211, 562212, 562213, 562219, 562920 (Limited to 
facilities regulated under the Resource Conservation and Recovery Act, 
subtitle C, 42 U.S.C. 6921 et seq.) (corresponds to SIC code 4953, 
Refuse Systems).
     Federal facilities.
    To determine whether your facility would be affected by this 
action, you should carefully examine the applicability criteria in part 
372, subpart B of Title 40 of the Code of Federal Regulations. If you 
have questions regarding the applicability of this action to a 
particular entity, consult the person listed under FOR FURTHER 
INFORMATION CONTACT.

B. What action is the agency taking?

    EPA is proposing to add a NPEs category to the list of toxic 
chemicals subject to reporting under EPCRA section 313 and PPA section 
6607. As discussed in more detail later in this document, EPA is 
proposing to add this chemical category to the EPCRA section 313 list 
because EPA believes NPEs meet the EPCRA section 313(d)(2)(C) toxicity 
criteria.

C. What is the agency's authority for taking this action?

    This action is issued under EPCRA sections 313(d) and 328, 42 
U.S.C. 11023 et seq., and PPA section 6607, 42 U.S.C. 13106. EPCRA is 
also referred to as Title III of the Superfund

[[Page 80625]]

Amendments and Reauthorization Act of 1986.
    Section 313 of EPCRA, 42 U.S.C. 11023, requires certain facilities 
that manufacture, process, or otherwise use listed toxic chemicals in 
amounts above reporting threshold levels to report their environmental 
releases and other waste management quantities of such chemicals 
annually. These facilities must also report pollution prevention and 
recycling data for such chemicals, pursuant to section 6607 of the PPA, 
42 U.S.C. 13106. Congress established an initial list of toxic 
chemicals that was comprised of 308 individually listed chemicals and 
20 chemical categories.
    EPCRA section 313(d) authorizes EPA to add or delete chemicals from 
the list and sets criteria for these actions. EPCRA section 313(d)(2) 
states that EPA may add a chemical to the list if any of the listing 
criteria in EPCRA section 313(d)(2) are met. Therefore, to add a 
chemical, EPA must demonstrate that at least one criterion is met, but 
need not determine whether any other criterion is met. Conversely, to 
remove a chemical from the list, EPCRA section 313(d)(3) dictates that 
EPA must demonstrate that none of the criteria in ECPRA section 
313(d)(2) are met. The listing criteria in EPCRA section 313(d)(2)(A)-
(C) are as follows:
     The chemical is known to cause or can reasonably be 
anticipated to cause significant adverse acute human health effects at 
concentration levels that are reasonably likely to exist beyond 
facility site boundaries as a result of continuous, or frequently 
recurring, releases.
     The chemical is known to cause or can reasonably be 
anticipated to cause in humans: Cancer or teratogenic effects, or 
serious or irreversible reproductive dysfunctions, neurological 
disorders, heritable genetic mutations, or other chronic health 
effects.
     The chemical is known to cause or can be reasonably 
anticipated to cause, because of its toxicity, its toxicity and 
persistence in the environment, or its toxicity and tendency to 
bioaccumulate in the environment, a significant adverse effect on the 
environment of sufficient seriousness, in the judgment of the 
Administrator, to warrant reporting under this section.
    EPA often refers to the EPCRA section 313(d)(2)(A) criterion as the 
``acute human health effects criterion;'' the EPCRA section 
313(d)(2)(B) criterion as the ``chronic human health effects 
criterion;'' and the EPCRA section 313(d)(2)(C) criterion as the 
``environmental effects criterion.''
    EPA published in the Federal Register of November 30, 1994 (59 FR 
61432) (FRL-4922-2), a statement clarifying its interpretation of the 
EPCRA section 313(d)(2) and (d)(3) criteria for modifying the EPCRA 
section 313 list of toxic chemicals.

II. Background Information

A. What are NPEs?

    NPEs are nonionic surfactants containing a branched nine-carbon 
alkyl chain bound to phenol and a chain of repeating ethoxylate units 
(C9H19C6H4(OCH2CH
2)nOH). The number of repeating ethoxylate units 
(n) can range from 1 to 100 (Reference (Ref.) 1). The major positional 
isomer is para (>=90%), while the ortho isomer is typically less than 
10% (Ref. 2). The number of ethoxylate units can be designated as NP#EO 
where # indicates the number of ethoxylate groups. For example, 
nonylphenol monoethoxylate would be NP1EO and nonylphenol diethoxylate 
would be NP2EO. Alternatively, NPE-# can be used where # indicates the 
number of ethoxylate groups. The surfactant properties of NPEs have 
resulted in their widespread industrial and commercial use in 
adhesives, wetting agents, emulsifiers, stabilizers, dispersants, 
defoamers, cleaners, paints, and coatings (Refs. 1, 3, 4, 5, and 6). 
The widespread use of NPEs surfactants has resulted in their release to 
surface waters (Ref. 4).

B. How does EPA propose to list NPEs?

    EPA is proposing to list NPEs as a category that would include the 
thirteen NPEs that currently appear on the Toxic Substances Control Act 
inventory (https://www.epa.gov/tsca-inventory). The NPEs category would 
be defined as Nonylphenol Ethoxylates and would only include those 
chemicals covered by the following Chemical Abstracts Service Registry 
Numbers (CASRNs):
    [ssquf] 7311-27-5; Ethanol, 2-[2-[2-[2-(4-
nonylphenoxy)ethoxy]ethoxy]ethoxy]-
    [ssquf] 9016-45-9; Poly(oxy-1,2-ethanediyl), [alpha]-(nonylphenyl)-
[omega]-hydroxy-
    [ssquf] 20427-84-3; Ethanol, 2-[2-(4-nonylphenoxy)ethoxy]-
    [ssquf] 26027-38-3; Poly(oxy-1,2-ethanediyl), [alpha]-(4-
nonylphenyl)-[omega]-hydroxy-
    [ssquf] 26571-11-9; 3,6,9,12,15,18,21,24-Octaoxahexacosan-1-ol, 26-
(nonylphenoxy)-
    [ssquf] 27176-93-8; Ethanol, 2-[2-(nonylphenoxy)ethoxy]-
    [ssquf] 27177-05-5; 3,6,9,12,15,18,21-Heptaoxatricosan-1-ol, 23-
(nonylphenoxy)-
    [ssquf] 27177-08-8; 3,6,9,12,15,18,21,24,27-Nonaoxanonacosan-1-ol, 
29-(nonylphenoxy)-
    [ssquf] 27986-36-3; Ethanol, 2-(nonylphenoxy)-
    [ssquf] 37205-87-1; Poly(oxy-1,2-ethanediyl), [alpha]-
(isononylphenyl)-[omega]-hydroxy-
    [ssquf] 51938-25-1; Poly(oxy-1,2-ethanediyl), [alpha]-(2-
nonylphenyl)-[omega]-hydroxy-
    [ssquf] 68412-54-4; Poly(oxy-1,2-ethanediyl), [alpha]-
(nonylphenyl)-[omega]-hydroxy-, branched
    [ssquf] 127087-87-0; Poly(oxy-1,2-ethanediyl), [alpha]-(4-
nonylphenyl)-[omega]-hydroxy-, branched

III. What is EPA's evaluation of the ecological toxicity and 
environmental fate of NPEs?

    EPA prepared two technical documents to support the listing of the 
NPEs category. The first document is ``Chemistry and Environmental Fate 
ofol Ethoxylates (NPEs)'' (Ref. 7), which provides detailed information 
on the chemistry and environmental fate of NPEs. The second document is 
``Ecological Hazard Assessment for Nonylphenol Monoethoxylate (NP1EO) 
and Nonylphenol Diethoxylate (NP2EO)'' (Ref. 8), which provides an 
assessment of the ecological toxicity of short-chain NPEs. Unit III.A. 
provides a brief summary of the chemistry and environmental fate of 
NPEs and Unit III.B. provides a brief summary of the ecological 
toxicity of short-chain NPEs. Readers should consult the support 
documents (Refs. 7 and 8) for further information.

A. What is the environmental fate of nonylphenol ethoxylates?

    In the environment, NPEs (in particular, those containing long 
ethoxylate chains) are expected to have very low volatility based on 
Henry's law constant values of <9.8 x 10-7 atmospheres-cubic 
meter per mole (atm-m\3\/mol) (Ref. 9). However, the vapor pressures of 
some of the degradation products of long-chain NPEs (e.g., nonylphenol, 
NP1EO) indicate the potential to exist in the atmosphere in the vapor 
phase. Although nonylphenol itself is somewhat volatile, volatilization 
of most NPEs from soil and water surfaces is not expected to be a 
significant environmental transport process. The potential for 
adsorption of NPEs to organic carbon in soil and to suspended solids 
and sediment in water is expected to increase with decreasing 
ethoxylation as water solubilities decrease (Ref. 9). In general, 
partitioning to soils and sediments is expected to be significant based 
on carbon-normalization partition coefficient (log Koc) 
values of 4.87-5.46 for NP1EO, NP2EO, and NP3EO and 3.61-4.63 for

[[Page 80626]]

NP9EO, which indicate a potential for strong adsorption to suspended 
solids and sediments in water and to organic matter in soils (Ref. 9). 
The highly water-soluble, higher molecular weight (i.e., longer chain) 
NPEs are expected to adsorb less to organic carbon, and may therefore 
have some mobility in soil (Refs. 9 and 10).
    Biodegradation is the dominant fate process for NPEs in the 
environment; abiotic degradation processes such as hydrolysis are not 
expected to be significant (Ref. 9). The available data indicate that 
NPEs undergo rapid primary biodegradation but slow ultimate 
biodegradation (Refs. 11, 12, 13, 14, 15, 16, 17, 18, and 19). Half-
lives ranging from 2 to 57.8 days have been determined for these 
substances based on river water die-away studies, which report primary 
degradation (Ref. 13). Anaerobic biodegradation appears to proceed more 
slowly than aerobic biodegradation (Ref. 13). Nonylphenol ethoxylate 
biodegradation products include shorter chain NPEs and 
ethoxycarboxylates. (Refs. 9, 10, and 20). Nonylphenol 
ethoxycarboxylates are NPEs that terminate with a carboxylate group (-
CO2H) rather than an alcohol group (-OH). Although not 
commonly observed under aerobic conditions, nonylphenol is a major 
metabolite of NPEs under anaerobic conditions (Refs. 9, 10, 21, 22, 23, 
24, 25, 26, and 27).
    Well-designed and properly functioning wastewater treatment plants 
(WWTPs) can greatly reduce effluent concentrations of NPEs and their 
degradation products relative to those found in the influent (Ref. 28). 
However, treatment efficiency varies considerably for WWTPs depending 
on plant design and operating conditions (Refs. 10, 29, 30, 31, and 
32). WWTP effluent remains a significant source of NPEs, nonylphenol 
ethoxycarboxylates, and nonylphenol in the environment, and 
concentrations of these compounds in surface waters, sediments, and 
wildlife tend to be higher near WWTP outfalls (Refs. 10, 31, 33, 34, 
35, 36, and 37).
    Nonylphenol ethoxylates and the degradation products, nonylphenol 
ethoxycarboxylates and nonylphenol, are widely distributed in surface 
waters, including rivers, lakes, estuaries, marine ecosystems, and 
their underlying sediments (Refs. 10, 31, 33, 34, 35, 38, 39, 40, and 
41). The more hydrophobic of these compounds, such as nonylphenol, 
NP1EO, and NP2EO, tend to partition to sediments (Ref. 10). Because 
sediments are often anaerobic, sorbed nonylphenol ethoxylates and their 
degradation products undergo further biodegradation slowly, ultimately 
producing nonylphenol. Through a combination of strong sorption and 
slow biodegradation, NPEs and nonylphenol can accumulate in sediments 
in concentrations that are much higher than are found in the 
surrounding water (Refs. 10 and 37) and can persist for years (Ref. 
42).

B. What is the ecological toxicity of short-chain NPEs?

    For NPEs, aquatic toxicity generally decreases as the length of the 
ethoxylate chain increases (Refs. 43 and 44). The available data show 
that NP1EO and NP2EO are significantly more toxic to aquatic organisms 
than the longer chain ethoxylates (e.g., NP9EO). Experimental data on 
acute aquatic toxicity of NP1EO indicate 96-hour LC50 values 
(i.e., the concentration that is lethal to 50% of test organisms) as 
low as 218 [mu]g/L in the fathead minnow (Pimphales promelas) (Ref. 
45). The 48-hour LC50 for the water flea, (Daphnia magna) 
and NP2EO was as low as 148 [mu]g/L (Ref. 46). Longer term exposures to 
NP1EO resulted in a Maximum-Acceptable-Toxicant-Concentration (MATC) of 
61 [micro]g/L based on an increase of mixed secondary sex 
characteristics for the Japanese medaka (Oryzias latipes) (Ref. 47). 
Exposure of rainbow trout (Oncorhynchus mykiss) to NP2EO indicated a 
22-day Lowest-Observed-Effect-Concentration (LOEC) for growth 
inhibition of 1 [micro]g/L (Ref. 48). Gonadosomatic Index (GSI) (weight 
of testes expressed as a percentage of total body weight) in rainbow 
trout also decreased relative to controls with a 21-day LOEC of 38 
[micro]g/L for NP2EO (Ref. 49). Additional toxicity values are included 
in the ecological hazard assessment (Ref. 8).
    The available experimental data demonstrate that NP1EO and NP2EO 
have been shown to cause acute and chronic toxicity to aquatic 
organisms at very low concentrations (Ref. 8). They have been shown to 
reduce individual survival, growth, and reproduction in aquatic 
organisms and NP2EO has been shown to reduce testicular growth and GSI 
in fish. The concentrations at which toxicity is observed are well 
below 1 mg/L and as low as 148 [mu]g/L for acute effects and less than 
0.1 mg/L for chronic effects. Acute and chronic toxicity values at 
these low concentrations show that NP1EO and NP2EO are highly toxic to 
aquatic organisms.

IV. Rationale for Listing NPEs

    The NPEs category that EPA is proposing to add to the EPCRA section 
313 toxic chemical list, contains both short and long-chain NPEs. 
Short-chain NPEs are highly toxic to aquatic organisms with toxicity 
values well below 1 mg/L as described in Unit III. Therefore, EPA 
believes that the evidence is sufficient for listing short-chain NPEs 
on the EPCRA section 313 toxic chemical list pursuant to EPCRA section 
313(d)(2)(C) based on the available ecological toxicity data. Long-
chain NPEs, while not as toxic as short-chain NPEs, degrade in the 
environment to produce products that include highly toxic short-chain 
NPEs and nonylphenol. Nonylphenol is even more toxic to aquatic 
organisms than short-chain NPEs and was added to the EPCRA section 313 
toxic chemical list based on its toxicity to aquatic organisms (79 FR 
58686, FRL-9915-59-OEI, September 30, 2014). As a source of degradation 
products that are highly toxic to aquatic organisms, EPA believes that 
the evidence is sufficient for listing long-chain NPEs on the EPCRA 
section 313 toxic chemical list pursuant to EPCRA section 313(d)(2)(C) 
based on the available ecological toxicity and environmental fate data.
    EPA does not believe that it is appropriate to consider exposure 
for chemicals that are highly toxic based on a hazard assessment when 
determining if a chemical can be added for environmental effects 
pursuant to EPCRA section 313(d)(2)(C) (see 59 FR 61440-61442). 
Therefore, in accordance with EPA's standard policy on the use of 
exposure assessments (see November 30, 1994 (59 FR 61432) (FRL-4922-
2)), EPA does not believe that an exposure assessment is necessary or 
appropriate for determining whether NPEs meet the criteria of EPCRA 
section 313(d)(2)(C).

V. References

    The following is a listing of the documents that are specifically 
referenced in this document. The docket includes these documents and 
other information considered by EPA, including documents that are 
referenced within the documents that are included in the docket, even 
if the referenced document is not itself physically located in the 
docket. For assistance in locating these other documents, please 
consult the person listed under FOR FURTHER INFORMATION CONTACT.

1. Dow Chemical. 2010. Product safety assessment. Nonylphenol 
ethoxylate surfactants. The Dow Chemical Company. October 11, 2010.
2. Naylor, C.G. 2004. The environmental safety of alkylphenol 
ethoxylates demonstrated by risk assessment and guidelines for their 
safe use. In: Handbook of detergents. Part B: Environmental impact. 
New York, NY: Marcel Dekker. p. 429-445.
3. Dow Chemical. 2002. Tergitol. Nonylphenol ethoxylate surfactants.

[[Page 80627]]

Products and applications. Dow Chemical Company, Midland, MI.
4. USEPA. 2009. Testing of certain nonylphenol and nonylphenol 
ethoxylate substances. Federal Register 74(115):28654-28262.
5. USEPA. 2010. Poly(oxy-1,2-ethanediyl),-alpha. 
(nonylphenyl)-.omega.-hydroxy-. IUR (Inventory Update Reporting) 
data. Non-confidential 2006 IUR records by chemical, including 
manufacturing, processing and use information.
6. USEPA. 2010. Nonylphenol (NP) and Nonylphenol Ethoxylates (NPEs) 
Action Plan. RIN 2070eZA09.
7. USEPA, OPPT. Chemistry and Environmental Fate of Nonylphenol 
Ethoxylates (NPEs). May 10, 2016.
8. USEPA, OPPT. Ecological Hazard Assessment for Nonylphenol 
Monoethoxylate (NP1EO) and Nonylphenol Diethoxylate (NP2EO). May 5, 
2016.
9. Staples, C.A., G.M. Klecka, C.G. Naylor, and B.S. Losey. 2008. 
C8- and C9-alkylphenols and ethoxylates: 1. Identity, physical 
characterization, and biodegradation pathways analysis. Hum. Ecol. 
Risk Assess. 14(5):1007-1024.
10. Ying, G.G., B. Williams, and R. Kookana. 2002. Environmental 
fate of alkylphenols and alkylphenol ethoxylates: a review. Environ. 
Int. 28:215-226.
11. Ahel, M., D. Hr[scaron]ak, and W. Giger. 1994. Aerobic 
transformation of short-chain alkylphenol polyethoxylates by mixed 
bacterial cultures. Arch. Environ. Contam. Toxicol. 26:540-548.
12. Jurado, E., M. Fern[aacute]ndez-Serrano, J. N[uacute][ntilde]ez-
Olea, and M. Lechuga. 2009. Aerobic biodegradation of a nonylphenol 
polyethoxylate and toxicity of the biodegradation metabolites. Bull. 
Environ. Contam. Toxicol. 83:307-312.
13. Klecka, G.M., C.A. Staples, C.G. Naylor, K.B. Woodburn, and B.S. 
Losey. 2008. C8- and C9-Alkylphenols and ethoxylates: II. Assessment 
of environmental persistence and bioaccumulation potential. Hum. 
Ecol. Risk Assess. 14(5):1025-1055.
14. Kve[scaron]tak, R., and M. Ahel. 1995. Biotransformation of 
nonylphenol polyethoxylate surfactants by estuarine mixed bacterial 
cultures. Arch. Environ. Contam. Toxicol. 29:551-556.
15. Maki, H., M. Fujita, and Y. Fujiwara. 1996. Identification of 
final biodegradation product of nonylphenol ethoxylate (NPE) by 
river microbial consortia. Bull. Environ. Contam. Toxicol. 57:881-
887.
16. Manzano, M.A., J.A. Perales, D. Sales, and J.M. Quiroga. 1999. 
The effect of temperature on the biodegradation of a nonylphenol 
polyethoxylate in river water. Water Res. 33(11):2593-2600.
17. Potter, T. L., K. Simmons, J. Wu, M. Sanchez-Olvera, P. 
Kostecki, and E. Calabrese. 1999. Static die-away of a nonylphenol 
ethoxylate surfactant in estuarine water samples. Environ. Sci. 
Technol. 33:113-118.
18. Quiroga, J.M., M.A. Manzano, D. Sales, and J.A. Perales. 1996. 
Biodegradation of a nonyfenol polyethoxilate (NPEO) in river water. 
Barcelona, Spain: World Surfactant Congress, 4th. p. 417-425.
19. Staples, C.A., C.G. Naylor, J.B. Williams, and W.E. Gledhill. 
2001. Ultimate biodegradation of alkylphenol ethoxylate surfactants 
and their biodegradation intermediates. Environ. Toxicol. Chem. 
20(11):2450-2455.
20. Gu, X., Y. Zhang, J. Zhang, M. Yang, H. Tamaki, Y. Kamagata, and 
D. Li. 2010. Isolation of phylogenetically diverse nonylphenol 
ethoxylate-degrading bacteria and characterization of their 
corresponding biotransformation pathways. Chemosphere 80:216-222.
21. Lu, J., Q. Jin, Y. He, and J. Wu. 2007. Biodegradation of 
nonylphenol polyethoxylates under Fe(III)-reducing conditions. 
Chemosphere 69:1047-1054.
22. Lu, J., Q. Jin, Y. He, J. Wu, W. Zhang, and J. Zhao. 2008. 
Anaerobic degradation behavior of nonylphenol polyethoxylates in 
sludge. Chemosphere 71:345-351.
23. Patureau, D., N. Delgenes, and J.P. Delgenes. 2008. Impact of 
sewage sludge treatment processes on the removal of the endocrine 
disrupters nonylphenol ethoxylates. Chemosphere 72:586-591.
24. Luppi, L.I., I. Hardmeier, P.A. Babay, R.F. Itria, and L. 
Erijman. 2007. Anaerobic nonylphenol ethoxylate degradation coupled 
to nitrate reduction in a modified biodegradability batch test. 
Chemosphere 68:2136-2143.
25. Chang, B.V., C.H. Yu, and S.Y. Yuan. 2004. Degradation of 
nonylphenol by anaerobic microorganisms from river sediment. 
Chemosphere 55:493-500.
26. Ejlertsson, J., M.L. Nilsson, H. Kylin, A. Bergman, L. Karlson, 
M. Oquist, and B.H. Svensson. 1999. Anaerobic degradation of 
nonylphenol mono- and diethoxylates in digestor sludge, landfilled 
municipal solid waste, and landfilled sludge. Environ. Sci. Technol. 
33(2):301-306.
27. Giger, W., P.H. Brunner, and C. Schaffner. 1984. 4-Nonylphenol 
in sewage sludge: accumulation of toxic metabolites from nonionic 
surfactants. Science 225:623-625.
28. Ying, G., and R.S. Kookana. 2003. Degradation of five selected 
endocrine-disrupting chemicals in seawater and marine sediment. 
Environ. Sci. Technol. 37(7):1256-1260.
29. Loyo-Rosales, J.E., C.P. Rice, and A. Torrents. 2007. Fate of 
octyl- and nonylphenol ethoxylates and some carboxylated derivatives 
in three American wastewater treatment plants. Environ. Sci. 
Technol. 41(19):6815-6821, Including supplemental information.
30. Ahel, M., W. Giger, and C. Schaffner. 1994. Behaviour of 
alkylphenol polyethoxylate surfactants in the aquatic environment--
II. Occurrence and transformation in rivers. Water Res. 28:1142-
1152.
31. Barber, L.B., B.K. Brown, and S.D. Zaugg. 2000. Potential 
endocrine disrupting organic chemicals in treated municipal 
wastewater and river water. In: Keith L.H., T.L. Jones-Lepp, and 
L.L. Needham, eds. Analysis of Environmental Endocrine Disruptors, 
ACS Symposium Series 747. American Chemical Society, Washington, DC 
USA. p. 97-123.
32. Shao, B., J. Hu, and M. Yang. 2003. Nonylphenol ethoxylates and 
their biodegradation intermediates in water and sludge of a sewage 
treatment plant. Bull. Environ. Contam. Toxicol. 70:527-532.
33. Rice, C. P., I. Schmitz-Afonso, J.E. Lolyo-Rosales, E. Link, R. 
Thoma, L. Fay, Altfater, D., and M.J. Camp. 2003. Alkylphenol and 
alkylphenol-ethoxylates in carp, water, and sediment from the 
Cuyahoga River, Ohio. Environ. Sci. Technol. 37:3747-3754.
34. Bennett, E.R., and C.D. Metcalfe. 1998. Distribution of 
alkylphenol compounds in Great Lakes sediments, United States and 
Canada. Environ. Toxicol. Chem. 17(7):1230-1235.
35. Bennett, E.R., and C.D. Metcalfe. 2000. Distribution of 
degradation products of alkylphenol ethoxylates near sewage 
treatment plants in the lower Great Lakes, North America. Environ. 
Toxicol. Chem. 19(4):784-792.
36. Ferguson, P.L., C.R. Iden, and B.J. Brownawell. 2001. 
Distribution and fate of neutral alkylphenol ethoxylate metabolites 
in a sewage-impacted urban estuary. Environ. Sci. Technol. 
35(12):2428-2435.
37. Ferguson, P.L., R.F. Bopp, S.N. Chillrud, R.D. Aller, and B.J. 
Brownawell. 2003. Biogeochemistry of nonylphenol ethoxylates in 
urban estuarine sediments. Environ. Sci. Technol. 37:3499-3506.
38. Bennie, D.T. 1999. Review of the environmental occurrence of 
alkylphenols and alkylphenol ethoxylates. Water Qual. Res. J. Canada 
34:79-122.
39. Montgomery-Brown, J., and M. Reinhard. 2003. Occurrence and 
behavior of alkylphenol polyethoxylates in the environment. Environ. 
Eng. Sci. 20(5):471-486.
40. Naylor, C.G., J.P. Mieure, W.J. Adams, J.A. Weeks, and F.J. 
Castaidi. 1992. Alkylphenol ethoxylates in the environment. J. Am. 
Oil Chem. Soc. 69(7):695-703.
41. Kolpin, D.W., E.T. Furlong, M.T. Meyer, E.M. Thurman, S.D. 
Zaugg, L.B. Barber, and H.T. Buxton. 2002. Pharmaceuticals, 
hormones, and other organic wastewater contaminants in U.S. streams, 
1999-2000: A national reconnaissance. Environ. Sci. Technol. 
36(6):1202-1211.
42. Shang, D.Y., R.W. Macdonald, and M.G. Ikonmou. 1999. Persistence 
of nonylphenol ethoxylate surfactants and their primary degradation 
products in sediments from near a municipal outfall in the Strait of 
Georgia, British Columbia, Canada. Environ. Sci. Technol. 33:1366-
1372.
43. Hall, W.S., M.B. Patoczka, R.J. Mirenda, B.A. Porter, and E. 
Miller. 1989. Acute toxicity of industrial surfactants to Mysidopsis 
bahia. Arch. Environ. Contam. Toxicol. 18: 765-772.
44. Servos, M.R. 1999. Review of the aquatic toxicity, estrogenic 
responses and bioaccumulation of alkylphenols and alkylphenol 
polyethoxylates. Water Qual. Res. J. Canada 34: 123-177.

[[Page 80628]]

45. TenEyck, M.C. and T.P. Markee. 2007. Toxicity of nonylphenol, 
nonylphenol monoethoxylate, and nonylphenol diethoxylate and 
mixtures of these compounds to Pimephales promelas (Fathead minnow) 
and Ceriodaphnia dubia. Arch. Environ. Contam. Toxicol. 53: 599-606.
46. Maki, H., H. Okamura, I. Aoyama, and M. Fujita. 1998. 
Halogenation and toxicity of the biodegradation products of a 
nonionic surfactant, nonylphenol ethoxylate. Environ. Toxicol. Chem. 
17: 650-654.
47. Balch, G., and C. Metcalfe. 2006. Developmental effects in 
Japanese medaka (Oryzias latipes) exposed to nonylphenol ethoxylates 
and their degradation products. Chemosphere 62: 1214-1223.
48. Ashfield, L.A., T.G. Pottinger, and J.P. Sumpter. 1998. Exposure 
of female juvenile rainbow trout to alkylphenolic compounds results 
in modifications to growth and ovosomatic index. Environ. Toxicol. 
Chem. 17: 679-686.
49. Jobling, S., D. Sheahan, J.A. Osborne, P. Matthiessen, and J.P. 
Sumpter. 1996. Inhibition of testicular growth in rainbow trout 
(Oncorhynchus mykiss) exposed to estrogenic alkylphenolic chemicals. 
Environ. Toxicol. Chem. 15: 194-202.
50. USEPA, OPPT. Economic Analysis of the Proposed Rule to Add 
Nonylphenol Ethoxylates to the EPCRA Section 313 List of Toxic 
Chemicals. April 12, 2016.

VI. What are the Statutory and Executive Orders reviews associated with 
this action?

    Additional information about these statutes and Executive Orders 
can be found at http://www2.epa.gov/laws-regulations/laws-and-executive-orders.

A. Executive Order 12866: Regulatory Planning and Review and Executive 
Order 13563: Improving Regulation and Regulatory Review

    This action is not a significant regulatory action and was 
therefore not submitted to the Office of Management and Budget (OMB) 
for review under Executive Orders 12866 (58 FR 51735, October 4, 1993) 
and 13563 (76 FR 3821, January 21, 2011).

B. Paperwork Reduction Act (PRA)

    This action does not contain any new information collection 
requirements that require additional approval by OMB under the PRA, 44 
U.S.C. 3501 et seq. OMB has previously approved the information 
collection activities contained in the existing regulations and has 
assigned OMB control numbers 2025-0009 and 2050-0078. Currently, the 
facilities subject to the reporting requirements under EPCRA section 
313 and PPA section 6607 may use either EPA Toxic Chemicals Release 
Inventory Form R (EPA Form 1B9350-1), or EPA Toxic Chemicals Release 
Inventory Form A (EPA Form 1B9350-2). The Form R must be completed if a 
facility manufactures, processes, or otherwise uses any listed chemical 
above threshold quantities and meets certain other criteria. For the 
Form A, EPA established an alternative threshold for facilities with 
low annual reportable amounts of a listed toxic chemical. A facility 
that meets the appropriate reporting thresholds, but estimates that the 
total annual reportable amount of the chemical does not exceed 500 
pounds per year, can take advantage of an alternative manufacture, 
process, or otherwise use threshold of 1 million pounds per year of the 
chemical, provided that certain conditions are met, and submit the Form 
A instead of the Form R. In addition, respondents may designate the 
specific chemical identity of a substance as a trade secret pursuant to 
EPCRA section 322, 42 U.S.C. 11042, 40 CFR part 350.
    OMB has approved the reporting and recordkeeping requirements 
related to Forms A and R, supplier notification, and petitions under 
OMB Control number 2025-0009 (EPA Information Collection Request (ICR) 
No. 1363) and those related to trade secret designations under OMB 
Control 2050-0078 (EPA ICR No. 1428). As provided in 5 CFR 1320.5(b) 
and 1320.6(a), an Agency may not conduct or sponsor, and a person is 
not required to respond to, a collection of information unless it 
displays a currently valid OMB control number. The OMB control numbers 
relevant to EPA's regulations are listed in 40 CFR part 9 or 48 CFR 
chapter 15, and displayed on the information collection instruments 
(e.g., forms, instructions).

C. Regulatory Flexibility Act (RFA)

    I certify that this action will not have a significant economic 
impact on a substantial number of small entities under the RFA, 5 
U.S.C. 601 et seq. The small entities subject to the requirements of 
this action are small manufacturing facilities. The Agency has 
determined that of the 178 entities estimated to be impacted by this 
action, 161 are small businesses; no small governments or small 
organizations are expected to be affected by this action. All 161 small 
businesses affected by this action are estimated to incur annualized 
cost impacts of less than 1%. Thus, this action is not expected to have 
a significant adverse economic impact on a substantial number of small 
entities. A more detailed analysis of the impacts on small entities is 
located in EPA's economic analysis (Ref. 50).

D. Unfunded Mandates Reform Act (UMRA)

    This action does not contain an unfunded mandate of $100 million or 
more as described in UMRA, 2 U.S.C. 1531-1538, and does not 
significantly or uniquely affect small governments. This action is not 
subject to the requirements of UMRA because it contains no regulatory 
requirements that might significantly or uniquely affect small 
governments. EPA did not identify any small governments that would be 
impacted by this action. EPA's economic analysis indicates that the 
total cost of this action is estimated to be $619,627 in the first year 
of reporting (Ref. 50).

E. Executive Order 13132: Federalism

    This action does not have federalism implications as specified in 
Executive Order 13132 (64 FR 43255, August 10, 1999). It will not have 
substantial direct effects on the States, on the relationship between 
the national government and the States, or on the distribution of power 
and responsibilities among the various levels of government.

F. Executive Order 13175: Consultation and Coordination With Indian 
Tribal Governments

    This action does not have tribal implications as specified in 
Executive Order 13175 (65 FR 67249, November 9, 2000). This action 
relates to toxic chemical reporting under EPCRA section 313, which 
primarily affects private sector facilities. Thus, Executive Order 
13175 does not apply to this action.

G. Executive Order 13045: Protection of Children From Environmental 
Health Risks and Safety Risks

    EPA interprets Executive Order 13045 (62 FR 19885, April 23, 1997) 
as applying only to those regulatory actions that concern environmental 
health or safety risks that EPA has reason to believe may 
disproportionately affect children, per the definition of ``covered 
regulatory action'' in section 2-202 of the Executive Order. This 
action is not subject to Executive Order 13045 because it does not 
concern an environmental health risk or safety risk.

H. Executive Order 13211: Actions Concerning Regulations That 
Significantly Affect Energy Supply, Distribution, or Use

    This action is not subject to Executive Order 13211 (66 FR 28355, 
May 22, 2001), because it is not a significant regulatory action under 
Executive Order 12866.

[[Page 80629]]

I. National Technology Transfer and Advancement Act (NTTAA)

    This rulemaking does not involve technical standards and is 
therefore not subject to considerations under section 12(d) of NTTAA, 
15 U.S.C. 272 note.

J. Executive Order 12898: Federal Actions To Address Environmental 
Justice in Minority Populations and Low-Income Populations

    EPA has determined that this action will not have 
disproportionately high and adverse human health or environmental 
effects on minority or low-income populations as specified in Executive 
Order 12898 (59 FR 7629, February 16, 1994). This action does not 
address any human health or environmental risks and does not affect the 
level of protection provided to human health or the environment. This 
action adds an additional chemical to the EPCRA section 313 reporting 
requirements. By adding a chemical to the list of toxic chemicals 
subject to reporting under section 313 of EPCRA, EPA would be providing 
communities across the United States (including minority populations 
and low income populations) with access to data which they may use to 
seek lower exposures and consequently reductions in chemical risks for 
themselves and their children. This information can also be used by 
government agencies and others to identify potential problems, set 
priorities, and take appropriate steps to reduce any potential risks to 
human health and the environment. Therefore, the informational benefits 
of the action would have positive human health and environmental 
impacts on minority populations, low-income populations, and children.

List of Subjects in 40 CFR Part 372

    Environmental protection, Community right-to-know, Reporting and 
recordkeeping requirements, and Toxic chemicals.

    Dated: November 2, 2016.
Gina McCarthy,
Administrator.

    Therefore, it is proposed that 40 CFR chapter I be amended as 
follows:

PART 372--[AMENDED]

0
1. The authority citation for part 372 continues to read as follows:

    Authority: 42 U.S.C. 11023 and 11048.

0
2. In Sec.  372.65, paragraph (c) is amended by adding alphabetically 
an entry for ``Nonylphenol Ethoxylates (This category includes only 
those chemicals covered by the CAS numbers listed here)'' to the table 
to read as follows:

Sec.  372.65  Chemicals and chemical categories to which this part 
applies.

* * * * *
    (c) * * *

------------------------------------------------------------------------
                      Category name                       Effective date
------------------------------------------------------------------------
 
                              * * * * * * *
Nonylphenol Ethoxylates (This category includes only              1/1/18
 those chemicals covered by the CAS numbers listed here)
     7311-27-5 Ethanol, 2-[2-[2-[2-(4-
     nonylphenoxy)ethoxy]ethoxy]ethoxy]-
     9016-45-9 Poly(oxy-1,2-ethanediyl), [alpha]-
     (nonylphenyl)-[omega]-hydroxy-
     20427-84-3 Ethanol, 2-[2-(4-nonylphenoxy)ethoxy]-
     26027-38-3 Poly(oxy-1,2-ethanediyl), [alpha]-(4-
     nonylphenyl)-[omega]-hydroxy-
     26571-11-9 3,6,9,12,15,18,21,24-Octaoxahexacosan-1-
     ol, 26-(nonylphenoxy)-
     27176-93-8 Ethanol, 2-[2-(nonylphenoxy)ethoxy]-
     27177-05-5 3,6,9,12,15,18,21-Heptaoxatricosan-1-ol,
     23-(nonylphenoxy)-
     27177-08-8 3,6,9,12,15,18,21,24,27-Nonaoxanonacosan-
     1-ol, 29-(nonylphenoxy)-
     27986-36-3 Ethanol, 2-(nonylphenoxy)-
     37205-87-1 Poly(oxy-1,2-ethanediyl), [alpha]-
     (isononylphenyl)-[omega]-hydroxy-
     51938-25-1 Poly(oxy-1,2-ethanediyl), [alpha]-(2-
     nonylphenyl)-[omega]-hydroxy-
     68412-54-4 Poly(oxy-1,2-ethanediyl), [alpha]-
     (nonylphenyl)-[omega]-hydroxy-, branched
    127087-87-0 Poly(oxy-1,2-ethanediyl), [alpha]-(4-
     nonylphenyl)-[omega]-hydroxy-, branched
 
                              * * * * * * *
------------------------------------------------------------------------

[FR Doc. 2016-27547 Filed 11-15-16; 8:45 am]
 BILLING CODE 6560-50-P