[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: [email protected].
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