U.S. Environmental Protec tion Agency Draft 04/26/10 EPA Deliberative Document, Do Not Quote, Cite or Release

Nonylphenol (NP) and Nonylp henol Ethoxylates (NPEs)

Action Plan

I. Overview

Nonylphenol (NP) and nonylphe nol ethoxylates (NPEs) are pr oduced in large volumes, with uses that lead to widespread re lease to the aquatic environment. NP is persistent in the aquatic environment, moderately bioaccumulative, and extremel y toxic to aquatic organi sms. NP’s main use is

in the manufacture of NPEs. NPEs ar e nonionic surfactants that are used in a wide variety of industrial applications and consumer products. NPEs, though less toxic than NP, are also highly toxic to aquatic organisms, and in the environment degrade to more environmentally persistent NP. NP has also been detected in human breast milk, bl ood, and urine and is associated w ith reproductive and developmental

effects in rodents.

NPEs were once commonly used in househol d laundry detergents. EPA and the detergent manufacturers have cooperated to elim inate this use. Howeve r, NPEs are still wi dely used in large quantities in industrial laundry detergents and have some additional uses that lead to releases to water. Therefore, EPA intends to initiate action to address its concerns about potential ecological effects due to the manufacturing, processing, di stribution in commerce, and uses of NP and NPEs. Additionally, based on available exposure and he alth effects information, EPA c ontinues to have some concern about potential risk to human heal th. EPA anticipates that the actions put forward in this Action Plan will further reduce human exposure thereby reducing risk concerns associated with NP and NPEs.

II. Introduction

As part of EPA’s efforts to enhance the exis ting chemicals program under the Toxic Substances Control Act (TSCA; 15 U.S.C. §2601 et seq. ), the Agency intends to identify chemicals for Action Plan development based on their presence in humans; persistent, bioaccumulative, and toxic (PBT) characteristics; use in consumer products; production volume; or other similar factors. NP and certain oligomeric NPEs are highly toxic to aquatic organi sms, are moderately bioaccumulative in mollusks, are persistent in the aquatic e nvironment, and accumulate in soil s and sediments (EPA, 2005). This

Action Plan is based on EPA’s initia l review of readily available use, exposure, and hazard information on NP and NPEs. In developing the Action Plan, EP A considered which of the various authorities provided under TSCA and other statutes might be a ppropriate to address poten tial concerns regarding

NP and NPEs. The Action Plan is intended to descri be the courses of action the Agency intends to pursue in the near term to addre ss its concerns. It does not constitut e a final Agency determination or other final Agency action. Regul atory proceedings i ndicated by the Action Plan will include appropriate opportunities for public and stake holder input, including th rough notice-and-comment rulemaking processes.U.S. Environmental Protec tion Agency Draft 04/26/10 EPA Deliberative Document, Do Not Quote, Cite or Release

2 III. Scope of Review

This Action Plan addresses uses of nonylphenols and nonylphenol ethoxylates that fall into the general chemical categories of alkylphenols and alkylphenol ethoxylates (APEs), respectively.

Chemical Abstract Service registry names and numbers (CASRNs) routin ely used to refer to nonylphenols or nonylphenol ethoxylates may not accurate ly reflect the identity of those substances. The nine carbon nonyl group may be branched or linear and bind at various locations around the phenol ring (“ortho”, “meta” or “par a”). Many manufacturers incorrectly use the linear identity when referring to the branched nonyl phenol. CASRN 84852-15-3 corresponds to the most widely produced nonylphenol, branched 4-nonylphenol (refe rred to herein as NP). Note that NP is not a single chemical structure. It is a comp lex mixture of highly bran ched nonylphenols, largel y mono-substituted in the

para - position, but with small amounts of ortho - and di-substituted nonyl phenols. In addition it

includes small amounts of branched C 8 and C 10 alkyl groups (Seidel 2004a). Much of the literature refers to the linear (or normal-) nonylphe nol (CASRN 25152-52-3), often the specific para regioisomer (i.e. 4-n-nonylphenol , CASRN 104-40-5). Many, but not al l, references are inaccurate about the identity of the substances listed as nonylphe nol. This is likely due to inaccurate identities in the source material. A supplier of nonylphe nol may use CASRN 104- 40-5, signifying 4-nnonylphenol, while actually supplying br anched 4-nonylphenol (CASRN 84852-15-3).

The mono- and di-ethoxy NPEs (NP1EO, NP2EO) do not appear on the TSCA inventory, but are among the degradation products of the polymeric NPEs and may be present with NP in the environment in appreciable concentrations.

Production

Nonylphenol

U.S. demand for NP (which includes both produc tion and imports less ex ports) is estimated to be 380 million pounds in 2010 (ICIS, 2007). This is well within the range for the reported production volume (manufactured volume plus imports) reporte d under the TSCA Inventory Update Rule (IUR) in 2006, which ranged from approximately 100 to 500 million pounds, based on reporting for the most widely produced branched and linear nonylphe nol substances (i.e., CASRN 84852-15-3 and CASRN 25154-52-3, respectively).

Nonylphenol ethoxylates

NPEs are surface active agents (surfactants) that are part of the broade r category of surfactants known as alkyphenol ethoxylates (APE s). NPEs represent approximately 80% to 85% of the volume of APEs. Surfactants are generally cat egorized based upon their electric charge in water. Categories of surfactants include anionic (neg ative), nonionic (no charge), cati onic (positive), and amphoteric (positive and negative). NPEs ar e part of the nonionic category.U.S. Environmental Protec tion Agency Draft 04/26/10 EPA Deliberative Document, Do Not Quote, Cite or Release

3 U.S. demand for all surfactants in 2007 wa s 7.5 billion pounds (Rust a nd Wildes, 2008). U.S. and Canadian consumption of NPE surfactants has been estimated between 300 and 400 million pounds per year (EPA, 2008). In a study by ToxE cology in 2002, NPE surfactant consumption in Canada was estimated at approximate ly 29 million pounds. It is not clear if this es timate includes soap, so it may be an underestimate of total surfactan t consumption by Canada. However, if Canadian consumption of NPEs is approxi mately 29 million pounds, then U.S. consumption of NPEs would range from approximately 270 to 370 million pounds.

IV. Uses and Sub stitutes Summary

The primary use of NP is as an intermed iate in the manufacture of NPEs. NPEs are manufactured by reacting NP with ethylene oxi de (EO) under basic conditions. The degree of ethoxylation depends on the molar ratio of NP to EO. All degrees of ethoxylation may be manufactured under the CASRN for the poly-ethox ylates (formally poly(oxy-1,2-ethanediyl),  -(4- nonylphenyl)-  -hydroxy-, branched, CASRN 127087-87-0), as long as they ar e synthesized via polymerization reaction between NP and EO.

NP may also be reacted to form tris(4- nonyl-phenyl) phosphite (TNPP, CASRN 26523-78-4) an antioxidant used to pr otect polymers such as rubber, vinyl, polyolefins, and polys tyrenics (Seidel 2004a). TNPP is also used as a stabilizer in plas tic food packaging. Although it does contain residual NP, TNPP has been approved for this use by the Food and Drug Administration (FDA). FDA also lists

NP as an indirect food contact substance (Vazquez-Duhalt, et al., 2005). Barium and calcium salts of

NP are used as heat stabilizers for poly vinyl chloride (PVC) (Seide l 2004a). NP is also used as a catalytic diluent in epoxy resins (Seidel 2004a).

Non-ionic surfactants, including NPEs, are used in a wide vari ety of applications including detergents, cleaners, degreasers, dry cleaning aids, pe troleum dispersants, emul sifiers, wetting agents, adhesives, agrochemicals, paper and textile pro cessing formulations, prewash spotters, metalworking fluids, oilfield chemicals, paints and coatings, and dust control ag ents. NPEs are hydrophilic (“waterattracting”) at one end of the molecule and hydrophobic (“water-a voiding”) at the opposite end. The hydrophilic “head” attracts water a nd the hydrophobic “tail” attracts poor ly soluble substances, such as oils and greases. This ability to simultaneously attract wate r and hydrophobic substances makes NPEs useful in the surfactant appli cations listed above, accounting fo r nearly 80% of consumption. Additional uses include: 1) phosphate antioxidants for rubber and pl astics; and 2) mi scellaneous uses, including lube oil additi ves. These uses each account for anot her 10% of total consumption (ICIS, 2007).

Alternatives to NPEs

There is enormous variability in the stru cture of non-ionic surf actants. Most non-ionic surfactants rely on polyethoxylation to provide th e hydrophilic moiety. Othe rs rely on glycerol (glycerin), glucosides, or other s ugars, either as monosaccharides (e.g. sorbitol) or disaccharides (e.g.U.S. Environmental Protec tion Agency Draft 04/26/10 EPA Deliberative Document, Do Not Quote, Cite or Release

4 sucrose) (Seidel 2004c). The simplest substitution for NPEs is to use other APEs . NPEs are just one of many APEs available commercially, and other APEs are used for many of the same commercial purposes as emulsifiers, dispersant s, and surfactants. The main alte rnatives for NPEs also include alcohol ethoxylates, both linear and branched, and glucose-based carbohydrate derivatives such as alkylpolyglucoside, glucamides, and glucamine oxid es. Some surfactants may substitute for specific applications only, for instance, si licon surfactants are used in production of polyurethane foam while napthalene condensates are used in photofinishing soluti ons. In other cases, NPE can be replaced with

a surfactant blend of alternative nonionics or a ble nd that include anionic or amphoteric surfactants. Market acceptance of these alternatives depends on a number of fact ors including cost and performance in the intended use. Many of these a lternatives are less persistent and break down to chemicals which are less toxic than NP and may be deemed safer substitutes for NPEs by EPA (EPA 2010).

V. Hazard Identification Summary

The Office of Pollution Prevention and Toxics (OPPT) assessed the human health and environmental effects hazards of NP, specifical ly CASRN 84852-15-3, whic h is branched, parasubstituted NP, as part of its Hazard Characterization (HC) of 18 alklyphenols (http://www.epa.gov/chemrtk/hpvis /hazchar/Category_Alkylphenols_ Sept2009.pdf). This CASRN is one of two nonylphenol CASRNs in cluded in this Action Plan. The other CASRN, 25154-52-3, is for straight chain nonylphenol. Since very little stra ight chain nonylphenol is produced, OPPT’s HC coverage of CASRN 84852- 15-3 (and not of CASRN 25154-52-3) is used here. OPPT has evaluated the metabolism of NPEs in mammals [placeholder fo r future link] and has concluded that they are

metabolized to NP.

Human Health Effects

NP’s acute (oral and dermal) toxicity is low. NP is highly irritating and corrosive to the skin and eye, but does not have signif icant skin sensitizing potential. NOAELs (No Observed Adverse Effect Levels) and LOAELs (Lowest Observed Advers e Effect Levels) for syst emic toxicity (based on body weight or body weight gain) in repeat dose rat oral toxicity studies range from 13 to 100 mg/kgbw/day and from 43 to 400 mg/kg-bw/day, respectiv ely. NOAELs and LOAELs in rat for reproductive toxicity (based on decreases in epididymal sperm dens ity or testicular sperm h ead counts, increases in estrous cycle length, and decreases in ovarian wei ghts) range from 13 to19 mg /kg-bw/day, and from 43 to 64 mg/kg-bw/day, respectively. Developmental rat NOAELs and LOAELs for offspring (based on accelerated vaginal opening in pups) range approximately from 13 to 19 mg/kg-bw/day and from 43 to 64 mg/kg-bw/day, respectively. Developmental NOAELs and LOAELs for rat maternal toxicity (based on decreased terminal body weights) range from 13 to 19 mg/kg-bw/day and from 43 to 64 mg/kgbw/day, respectively. NP is not mutagenic in the Ames assay, in vitro chromosomal aberration assay,

or in vivo micronucleus assay. There are no data on its carcinogenic potential.U.S. Environmental Protec tion Agency Draft 04/26/10 EPA Deliberative Document, Do Not Quote, Cite or Release

5 Environmental Effects

Aquatic Toxicity:

The available acute and chronic t oxicity data of NP to aquatic or ganisms indicates NP is highly toxic to fish, aquatic invertebrates, and aquatic plants. The 28-day no observe d effect concentration (NOEC) of CASRN 84852-15-3 fo r fish ranges from 0.05 to 0.07 mg/L and the 28-day lowest observed effect concentration (LOEC) ranges fr om 0.12 to 0.19 mg/L. A 33-day NOEC for fish is 0.007 mg/L and the 33-day LOEC is 0.014 mg/L. The 21-day NOEC for aquatic invertebrates ranges from 0.10 to 0.24 mg/L (EU, 2002; Canada, 2002; EPA, 2005).

For NPEs, toxicity to aquatic organisms tends to decrease with increasing degree of ethoxylation. For example, acute toxicity to k illifish was 1.4 mg/L, 3 mg/L, 5.4 mg/L, 12 mg/L and 110 mg/L for NP, NP1EO (i.e., NPE with one ethoxyl ate group), NP6.4EO (i.e., NPE mixture with an average of 6.4 ethoxylate groups ), NP9EO and NP16.6EO, respectively (Canada, 2002). Environment Canada, based on a comprehensive analysis of ava ilable toxicity data for NP and NPEs, developed Toxic Equivalency Factors (TEFs) for NP and NP Es, as follows: NP =1 ; NP1EO and NP2EO =0.5 (i.e., half as toxic as NP ); NP3EO to NP8EO also = 0.5 (a conser vative estimate because of inadequate data); NP9EO and greater = 0.005 (i.e., 100 ti mes less toxic than NP) (Canada 2002).

Bioconcentration Factor (BCF)

The measured BCF for fish is lo w, ranging from 87 to 344. However, the BCF for mussel ranges from 14 (low) to 3,400 (moderate) (EPA, 1996).

VI. Physical-Chemical Properties a nd Fate Characterization Summary

NP is a clear to pale yellow viscous liquid at room temperature with moderate water solubility and moderate vapor pressure (A hel and Geiger, 1993; EU, 2002; Se idel, 2004b). NP has moderate volatility, and, while air concentrati ons of NP are generally expected to be low (EU, 2002), research

has shown that in some locations there may be water-to-air volatiliza tion that results in significant atmospheric concentrations of NP substances (Canada, 2002). In the atmosphere, NP will be degraded rapidly by hydroxyl radicals and is not expected to be persistent in air (rated a P1, low) (EPA, 2009). NP is primarily found in the environment as a degr adation product of NPEs. NP Es are released most often to sewage treatment plants, and are degr aded to shorter-chain NPEs, including NP1EO and NP2EO in active sewage sludge; these short-chain NPEs are then further degraded to NP (EPA, 2005). NP is expected to adsorb strongly to soils and sediments. In sewage tr eatment plants, NP is expected to partition to sludge, and when released to the aquatic environment, is expect ed to partition mainly between water and sediment (EPA, 2005; Canada, 2002). NP and NPEs that are present in surface waters or landfills may also potentially leach into groundwat er (Canada, 2002). NP undergoes biodegradation, but not readily, and is considered persistent in the aquatic environment (Canada, 2002).U.S. Environmental Protec tion Agency Draft 04/26/10 EPA Deliberative Document, Do Not Quote, Cite or Release

6 NPEs show a gradual, linear increase in wate r solubility with greater degree of ethoxylation (for example the reported water so lubility of NP5EO is 9.48 mg/L; of NP12EO, 42.5 mg/L) (Ahel and Giger 1993; Brix et al. 2001). There are conflicting re ports in the literature on the biodegradability of NP and NPEs. They are not readily biodegradable using standard tests, but are inherently biodegradable (Canada, 2002; EU, 2002). After a peri od of acclimation, NPEs, in sewage sludge or the natural environment, can undergo biodegradation to shorter-chain NPEs invol ving stepwise loss of ethoxy groups to lower NPE congeners (Maguire, 1999). In the environment the long-chain NPEs biodegrade relatively quickly to short-chain NPEs a nd NP, which are much more resistant to further degradation (Canada, 2002; EU, 2002). When in water, NPEs can also undergo photo-induced degradation (Canada, 2002), and NP can also be photol yzed in the surface layer of natural waters with a half-life of 10-15 hours (Canada, 2002).

VII. Exposure Characterization Summary

Releases

NPs and NPEs are not listed in the Toxic Release Inventory (T RI). No readily available, quantitative release data in the U.S. were found for NPs and NPEs. Based on information from the European Union (EU) and Canada (EU, 2002 and Environment Canada, 1999), there are

environmental releases of NPs and NPEs to wate r during their manufacture a nd uses including:

Release of NP

 during production of NPEs

 during production of nonylphenol/formaldehyde

 during production of epoxy resins

 during production of plastic Release of NP and NP

 in industrial and instit utional cleaning products

 during agricultural use Release of NPEs

 from emulsion polymerization processes

 in textiles processes including wool scouring

 from paper processes

 from printed circuit boards manufacturing processes

 from metal extraction, refini ng and processing industry

 during paints, lacquers and va rnishes manufacturing processes

 from use in deicer formulationsU.S. Environmental Protec tion Agency Draft 04/26/10 EPA Deliberative Document, Do Not Quote, Cite or Release

7 Human Exposure

There are no U.S. Occupational Health a nd Safety Administrati on (OSHA) Permissible Exposure Limits (PELs) or Nati onal Institute for Occupational Safety and Health (NIOSH) Recommended Exposure Limits (RELs) for NP or NPEs. No readily available, quantitative occupational exposure monitoring data in th e U.S. were found for NP and NPEs.

Based on IUR data, the total numb er of workers reasonably likely to be exposed to NP or NPEs during manufacturing and industr ial processing and use may be 1,000 or greater. There may be additional potentially exposed indust rial workers who are not included in this estimate. This estimate also does not include potentiall y exposed commercial workers.

The National Occupational Exposure Survey (NOES), conducted from 1981 to 1983, estimated 306, 211 workers were potentially exposed to NPs and 1,961,225 worker s were potentially exposed to NPEs. The Survey lists the linear isomer, but EPA believes the bran ched isomer is more accurate.

The following exposure information is based on information obtained from the EU (EU, 2002). It is not known if the processes a nd associated exposures in the U.S. would be similar to those in the European countries.

The EU Risk Assessment indicated the ma nufacturing and use of NP as a chemical intermediate is carried out in closed systems. Occupational exposure may occur during sampling, maintenance and product filling to drums and tankers (EC, 2002). Occupational exposure was estimated at about 0.9 mg/m 3 (8-hour TWA) for both production and use of NP (EC, 2002).

During the manufacture of specialty paints, th e EU identified two act ivities where potential exposure to NP may occur: during loading of th e NP into the solvent, and during coupling and uncoupling of the pipe work during product loading in to tins. The inhalation exposure was estimated to be 0.091 mg/m 3 (8-hour TWA), and the dermal exposure was estimated to be from 0 to 0.1 mg/cm 2 /day. During the use of these pain ts, the EU identified two exposu re points: mixing of the paint, and spray application. Dermal exposure during mixing was estimated to range from 0.01 to 0.24 mg/cm 2 /day, and inhalation exposure during sp raying was estimated to be 9.1 mg/m 3 (8-hour TWA) (EC, 2002).

No quantitative worker exposure data were found during the production of epoxy resins using NP. However, NP is blended directly into the hard ening component of the epoxy resin and filled into tubes for use (EC, 2002), indicating potential exposure s may occur from adding the NP to the mixer.

No readily available quantitative information on exposure to NP or NPEs were found for use of NP in the manufacturing of NPEs or the processing or uses of NP Es in industrial and institutional cleaning products, emulsion polymeriza tion, textiles, pulp and paper, electrical and el ectronic products, metal extraction, refining and pr ocessing industry or lacquers and varnishes industry.U.S. Environmental Protec tion Agency Draft 04/26/10 EPA Deliberative Document, Do Not Quote, Cite or Release

8 General population exposure to NP (either dir ectly or as a metabolite of NPE) has been confirmed by biomonitoring data fro m breast milk (Ademollo et al., 2008), umbilical cord blood (Chen et al., 2008) and urine (Calafet et al., 2008). Exposure is a result of the presence of NP and NPEs in detergents, cleaners, agricultural and indoor pes ticides, food packaging and cosmetics. These are potentially products of concern for women and ch ildren. For example, small children crawling on floors would be exposed to NPEs an d NP in floor and carpet cleaners.

Estimates of human exposure are available for several of these sources. These include exposures from: diet_0.1  g/kg/day from a reported 7.5  g/day with the conversion done for a 70 kg person (Guenther et al. 2002); hair dye_0.1  g/kg/day; food containers_2  g/kg/day; and indoor pesticides_0.35  g/kg/day (EU, 2002). The EU report al so estimates NP exposure due to

environmental sources to be 5  g/kg/day, with 70% – 80 % of th is due to fish and shellfish consumption (EU 2002). A biomonitoring study of breast milk also found a positive correlation between seafood consumption and levels of NP (Ademollo et al., 2008). Significant exposure could

also result from hard surface cleaners and thei r residue. The largest estimated exposure (4.4 mg/kg/day) was due to living n ear a textile factory that used NP and NPEs (EU, 2002). The appropriate exposure factors for dr inking water ingestion of water acr oss all ages ranges from a mean of 0.926 L/day to the 95 th percentile factor of 2.544 L/day (E PA, 2009). If the measured value of

1  g/L (EPA, 2001) for alkylphenols in drinking wate r is combined with the mean drinking water estimate of 0.926 L/day; the result is an estimated exposure of 0.01  g/kg/day. Based on this analysis, EPA believes that drinking water should not be the main source of exposure, a view shared by other sources (EU, 2002; Soar es et al. 2008).

Environmental Exposure

Ecological receptors have the potential for signi ficant exposure to NP a nd NPE for two reasons: 1) facilities that manufactur e products containing NP or NPEs are di scharging them into surface waters (Ellis et al., 1982); and 2) NP and NPEs tend to partition to sedime nts and accumulate (Naylor et al., 1992). Both freshwater and saltwater i nvertebrates, plants and fish ar e sensitive to this category of

chemicals and have demonstrated to xicity to it in varying degrees. EP A’s Office of Water has derived freshwater and saltwater water quality criteria (WQC) for NP. The acute and chronic WQC for freshwater species are 28 μ g/L and 6.6 μ g/L, respectively. The acute and chronic WQC for saltwater species are 7 μ g/L and 1.7 μ g/L, respectively (USEPA, 2005). A ra nge of surface water and sediment

levels of NP and NPEs have been measured in US waters. Surface waters near 11 different industrial discharges ranged in concentration of NP from 2 to 1617 μ g/L (Shackelford et al., 1983). Surface water

and sediments measured in the Great Lakes contained NP concentrations from 0.01 to 0.92 μ g/L for

water and 37 μ g/g to 300 μ g/g for sediments (Bennett et al., 1997). Surface water samples collected along the Ohio River measured for total NPEs ranged from 0.13 to 1.0 μ g/L for water, from 250 to

1020 μ g/g for sediments, and from 32 to 920 μ g/g for carp, a bottom dwelli ng fish (Rice et al., 2003).

Some of the measured surface water concentrations particularly those near industrial discharges exceed the WQC for freshwater species living in the wa ter column. NP and NPEs in the freshwater andU.S. Environmental Protec tion Agency Draft 04/26/10 EPA Deliberative Document, Do Not Quote, Cite or Release

9 saltwater ecosystems have the potential for ecological effects on all trophic leve ls of aquatic species exposed to them (USEPA, 2005).

VIII. Risk Management Considerations

General Considerations

EPA has identified a number of is sues that it has taken into cons ideration in the development of

an Action Plan for NP and NPEs:

1) NP and the short-chain NPEs (N P1EO and NP2EO) are persistent , moderately bioaccumulative, and extremely toxic to aquatic organisms. The lo ng-chain NPEs, while less “PBT”, are also highly toxic and degrade to the more toxic and persistent short forms of NPEs and NP in the environment. Internationally, Canada and the EU have acted to regulate NP and NPEs, and the United Nations Environment Programme (UNEP) ha s identified NP as a chemical of global concern in its Regionally-based Assessment of Persistent Toxic Substances. 2) NPEs are generally sold as mi xtures; substances represented by CASRNs under the IUR cover a broad spectrum of these substances. There appear to be possible reporting inaccuracies regarding what is actually manufactured. Original TSCA inve ntory substances identifi ed as straight-chain

substances have often been found to be branched-c hain forms. PMN submissions for straight-chain

NPEs have also been found to be branched a nd are corrected during the PMN review process. 3) NPEs frequently contain a mixture of substances with C6 to C12 (hexyl to dodecyl) alkylphenol ethoxylates; these “APEs” could al so be sold as easily manufactu red substitutes for NPEs. These substances are anticipated to have similar prope rties as NPEs. EPA notes, however, that for many uses of NPEs, safer substitute s are available and use of thes e substitute chemicals should be encouraged. 4) It appears that a large proportion of use and subse quent environmental release is associated with industrial laundries; howe ver, more analysis is needed to understand other TSCA (and non-TSCA)

uses and releases. 5) EPA’s Office of Pesticide Progr ams (OPP) also conducted an a ssessment of NPEs that was released shortly before publication of this doc ument. OPPT and OPP have worked together to ensure that the toxicological conclusions in both documents are consistent.

Potential Impacts on Children

There are potential children’s health concer ns related to NP and NPEs. NP exposure over several generations has been obser ved to cause slight changes in the estrous cycle length, timing of vaginal opening, ovarian weight, and sperm/sperma tid count in laboratory animals (EU, 2002), and more recently in vitro effects on human placenta (B echi et al., 2006; Bechi et al., 2010). These findings

are consistent with the observati on that NP has estrogenic activity (EU, 2002), but a mode of action analysis has not been conducted. Data on childre n’s exposure are limited, though children may have greater exposure to NP and NPEs because they consume more food, drink more water, and breatheU.S. Environmental Protec tion Agency Draft 04/26/10 EPA Deliberative Document, Do Not Quote, Cite or Release

10 more air per pound than adults. While biomonitoring data are also limited, a r ecent Italian study found maximum exposures from hu man breast milk of 3.9 μ g /kg/day (Ademollo, 2008).

IX. Next Steps

In conducting this review of NP and NPEs, EPA considered a number of potential risk management actions, including re gulatory actions under TSCA sections 4 and 5, requiring reporting under the Emergency Planning and Community Right-to-Know Act (E PCRA) section 313, and voluntary actions through such programs as Design for the Environment (DfE).

Based on its screening-level review of hazard and exposure information, EP A intends to initiate actions to protect humans and th e environment from exposure to NP and NPEs due to manufacture (including import) use, or disposal of commercial NP and NPEs. In addition, as part of the Agency’s

efforts to address these chemi cal substances, EPA also intends to evaluate the potential for disproportionate impact of e xposure to NP and NPEs on child ren and other sub-populations.

On the basis of existing information, the Agency believes that the follo wing actions would be

warranted:

1. Support and encourage the voluntary phase out of the use of NPEs in industrial laundry detergents.

a. In discussions with EPA, th e Textile Rental Services A ssociation of America (TRSA), whose members represent a large majority of the industrial launde rers in the U.S., agreed to expedite a phase out of the use of NPEs in industrial laundry detergents. The phase out, which has already begun, would end the use of NPEs in industrial laundry detergents by 2013 (for liquid detergents ) and 2014 (for powder detergents).

b. The phase-out of detergents in industrial laundry detergents and other products will also

be coordinated with EPA’s DfE Safer Detergents Stewardship Initiative (SDSI) program which has had great success in obtain ing public commitment by consumer product manufacturers to end the use of NPEs in household la undry detergents. EPA intends to encourage any indus trial launderers who are not members of TRSA to also join this effort.

2. Initiate rulemaking to simultaneously propose a TSCA significant new use rule (SNUR) and a

test rule for NP and NPEs.

a. The proposed SNUR would desi gnate use of NPEs in dete rgents and cleaning products as a significant new use, which would re quire submission of a significant new use notice (SNUN) to EPA at least 90 days befo re beginning that use. This gives EPA the opportunity to take regulator y action if appropriate. Th e proposed SNUR would be published at the end of 2011; with the effective date of the final SNUR timed to coincide with the anticipated completion of th e phase-out of NPEs in industrial laundry detergents.U.S. Environmental Protec tion Agency Draft 04/26/10 EPA Deliberative Document, Do Not Quote, Cite or Release

11 b. The proposed test rule under section 4 of TSCA would require development of the information necessary to determine the effect s that NPEs and NP have on human health or the environment. EPA has already issued an advance notice of proposed rulemaking (ANPRM) for NPEs and NP (published J une 17, 2009). However, EPA intends to

evaluate how releases and exposures are mitigated through the phase-out action; and would finalize any proposed te sting actions accordingly.

c. EPA also intends to evaluate the utility of issuing a SNUR for the straight-chain NPEs that EPA believes are no longer being ma nufactured. Many comm ercial NPEs are identified as linear nonyl isomer, but EPA be lieves that these may be misidentified branched forms. In part, the intent of the SNUR would be to eliminate discrepancies on the TSCA inventory and improve accura cy in reporting under the IUR.

d. In addition, EPA will consider SNURs for additional uses, depending on the results of an ongoing use and exposure analysis.

3. Initiate rulemaking under TSCA Section 5(b)(4) of TSCA to add NP and NPEs to the list of chemicals that present or may present an unr easonable risk of injury to health or the

environment. EPA intends to publish a notice of proposed rulemaking by the end of 2011.

4. Initiate rulemaking in late 2011 to add NP and NPEs to the TRI list. At pr esent, neither NP nor

NPEs are on this EPCRA section 313 list of toxic chemicals.

5. Support and encourage the elimination of other uses of NP and NPEs, followed by regulatory actions as necessary.

a. EPA intends to encourage the manufacturer s of all NPE-contai ning direct-release products (e.g., firefighting gels and foams, dust-control agents and deicers) to move to

NPE-free formulations. As TRSA implements its phase -out commitment through SDSI, it will provide an example for other product s ectors to follow, especially those with

“direct releases” to the e nvironment. The DfE-sponsored CleanGredients database offers a source of ready alternatives—f unctionally equivalent to NPEs based on performance characteristics and safer because they meet the Df E Criteria for Safer Surfactants. (For more information, visit http://www.epa.gov/dfe/pubs/pro jects/formulat/sdsi.htm. )

b. EPA will develop an alternatives analysis and encourage the elimination of NPE use in other industries that discharge NPEs to wate r, such as the pulp and paper processing and textile processing sectors, where safer alterna tives may be available. DfE also intends to expand the scope of SDSI, and encourage t hose industries to make commitments under

SDSI.

REFERENCES

Ahel, M. and Giger, W. 1993. Aque ous solubility of alkylphenols and alkylphenol polyethoxylates. Chemosphere 26(8): 1461-1470.U.S. Environmental Protec tion Agency Draft 04/26/10 EPA Deliberative Document, Do Not Quote, Cite or Release

12 Ademollo, N.; Ferrara, F.; Delise, M.; Fabietti, F.; and Funari, E. 2008. Nonylphenol and octylphenol

in human breast milk. Environment International . 34: 984-987.

Bechi, N.; Ietta, F.; Romagnoli, R; Focardi, S.; Cors i, I.; Buffi, C.; et al. 2006. Estrogen-Like Response to p-Nonylphenol in Human First Trimester Placenta and BeWo Choriocarcinoma Cells. Toxicological

Sciences 93(1):75-81.

Bechi, N.; Ietta, F.; Romagnoli, R; Jantra , S.; Cencini, M.; Galassi, G.; et al. 2010. Environmental Levels of para-Nonylphenol Are Able to Aff ect Cytokine Secretion in Human Placenta. E nvironmental Health Perspectives 118 (3):427-431.

Bennett, E.R. and Metcalfe, C.D. 1997. Distribu tion of Alkylphenol Co mpounds in Great Lakes Sediments, United States and Canada. Environmental Toxicology and Chemistry . 17(7):1230-1235.

Brix, R.; Hvidt, S.; a nd Carlsen, L. 2001. Solubility of nonyl phenol and nonylphenol ethoxylates. On the possible role of micelles. Chemosphere 44:759-763.

Calafat, A.; Kuklenyik, Z.; Re idy, J.; Caudill, S.; Ekong, J.; and Needham, L. 2008. Urinary concentration of Bisphenol A and 4-Nony lphenol in a human reference population. Environmental Health Perspectives . 113:391-395.

Canada. 1999. Environment Canada. Priority Substanc es List Assessment Re port: Nonylphenol and its Ethoxylates.

Canada. 2002. Environment Canada. Canadian Environm ental Quality Guidelines for Nonylphenol and its Ethoxylates (Water, Sediment, and Soil) Scientific Supporting Document . Ecosystem Health: Science-based Solutions Report N o. 1-3. National Guidelines and St andards Office, Environmental Quality Branch, Environment Canada.

Chen, M.; Chang, C.C.; Shen, Y.J.; Hung, J.H.; G uo, B.R.; Chuang, H.Y.; and Mao, I.F. 2008. Quantification of prenatal exposure and maternal-fetal transfer of nonylphenol. Chemosphere . 73:

5349-5245.

Ellis, D.D.; Jones, C.M.; Larson, R.A.; and Schaeffer, D.J. 1982. Or ganic constituents of mutagenic secondary effluents from wast ewater treatment plants. Archives of Environm ental Contamination and Toxicology . 11:373-382.

EPA. 1996. RM-1 Document for Para-Nonyphenol. Washington, DC. Office of Pollution, Prevention

and Toxics.

EPA. 1997. Exposure Factors Handbook. National Center for Environm ental Assessment. Washington, DC. August, 1997.U.S. Environmental Protec tion Agency Draft 04/26/10 EPA Deliberative Document, Do Not Quote, Cite or Release

13 EPA. 2001. Removal of Endocrine Di sruptor Chemicals Using Drinki ng Water Treatment Processes.

Office of Research and Deve lopment. Washington, DC 2046 0. EPA/625/R-00/015. March 2001.

EPA. 2005. Ambient Aquatic Life Wat er Quality Criteria-Nonylphenol Final. Office of Water, Office of Science and Technology, Washin gton, DC. EPA-822-R-05- 005. December, 2005.

EPA. 2006. Inventory Update Reporting (IUR). http://www.epa.gov/oppt/iur/ . Accessed February

2010.

EPA. 2008. Bi-national Framework for Identifying Substa nces of Potential Threat to The Great Lakes Basin, Test Case: Nonylphenol a nd its Ethoxylates (NPEs) . Draft, November 20, 2008. Citing [Colin
A. Houston & Associates, In c. Surfactant Market Profile : North America, June 2007.]

EPA. 2009. Estimation Programs Interface Suite TM for Microsoft® Windows, v4.00. U.S. Environmental Protection Agen cy, Washington, DC, USA.

http://www.epa.gov/opptintr/exposure/pubs/episuitedl.htm

.

EPA. 2009. Exposure Factors Handbook. http://www.epa.gov/ncea/efh/pubs/ . July 2009.

EPA 2010. DfE Criteria for Safer Chemical Ingredient s: DfE Criteria for Sa fer Surfactants. March

2010.

EU. 2002. European Union Risk Assessment Report. 4-Nonylphenol (Branched) and Nonylphenol. 2nd Prior ity List Volume: 10

Guenther, K.; Heinke, V.; Thiele, B.; Kleist, E.; Prast, H.; and Raecker, T. 2002. Endocrine Disrupting Nonylphenols Are Ub iquitous in Food. Environmental Science and Technology . 36: 1676-1680.

Huntsman, 2010. Annual Report Pursuant to Section 13 or 15( D) of the Securities Exchange Act of

1934 for the Fiscal Year Ended Decem ber 31, 2009. Form 10-K. February.

ICIS. Nonylphenol. http://www.icis.com/Articles/2007/06/ 25/4503346/nonylphenol.html. June 25

, 2007.

Maguire, R.J. 1999. Review of the persisten ce of nonylphenol and non ylphenol ethoxylates. Water Quality Research Journal of Canada . 34:37–78.

Naylor, C.G.; Mieure, J.P.; Adams, W.J.; Weeks, J.A.; Ca staldi, F.J.; Ogle, L. D.; and Romano, R.R. 1992. Alkylphenol ethoxylate s in the environment. Journal of the Americ an Oil Chemists’ Society

. 69:695-708.U.S. Environmental Protec tion Agency Draft 04/26/10 EPA Deliberative Document, Do Not Quote, Cite or Release

14 NIOSH, 1983. National Occupati onal Exposure Survey (NOES, 1981-1983). Accessed, 05/14/2008. http://www.cdc.gov/noes/

Rice, C.P.; Schmitz-Afonso, I.; Loyo -Rosales, J.E.; Link, E.; Thoma, R.; Fay, L.; Altfater, D.; and Camp, M.J. 2003. Alkylphenol and Al kylphenol-Ethoxylates in Carp, Water, and, sediment from the Cuyahoga River, Ohio. Environmental Science and Technology . 37:3747–3754.

Rust and Wildes. 2008. Surfactants A Market Opportunity Study Update. Prepared for the United Soybean Board. Omni Tech Inte rnational, Ltd. December.

Seidel, A. (2004a). Kirk-Othmer Encyclopedia of Chemical Technology. Hoboken, NJ, John Wiley & Sons, Inc. 2 : 225.

Seidel, A. (2004b). Kirk-Othmer Encyclopedia of Chemical Technology. Hoboken, NJ, John Wiley & Sons, Inc. 24 : 148.

Seidel, A. (2004c). Kirk-Othmer Encyclopedia of Chemical Technology. Hoboken, NJ, John Wiley & Sons, Inc. 2 : 205.

Schoenfuss, H.L.; S.E. Bartell, T. B. Bistodeau, R.A. Cediel, K.J. Gr ove, L. Zintek, K.E., Lee and L.B. Barber. 2008. Impairment of the reproductive potentia l of male fathead minnows by environmentally relevant exposures to 4-nonylphenol. Aquatic Toxicology 86: 91–98.

Shackelford, W.M., D.M. Cline, L. Faas and G. Kurth. 1983. Evaluation of automated spectrum matching for survey identification of wastew ater components by gas chromatography-mass spectrometry. PB83-182931. National Technical Information Service, Springfield, VA.

Soares , A.; Guieysse, B.; Jeffe rson, B.; Cartmell, E.; and Lester , J.N. 2008. Nonylphenol in the

environment: A critical review on occurrence, fate, toxicity and treatment in wastewaters. Environment

International 34: 1033–1049

Vazquez-Duhalt, R.; Marquez-Rocha, F.; Pon ce, E.; Licea, A. F.; and Viana, M.T. 2005. Nonylphenol, An Integrated Vision of a Polluta nt. Scientific Review. Applied Ecology and Environmental Research 4(1): 1-25.