Federal Registor 

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## I Pu.cs aod Reou~ations 5991

40 CFR Part799

IOPTS—42104B; FAL 3661-41

RIN 2070-AB07

Testing Consent OrderOn 4 Nonyiphenol, Branched

AGENCY: Environmental Protection Agency (EPA).
ACTION: Final rule.

SUMMARY: This document announces that EPA has signed an enforceable testing Consent Order with CAF Chemicals Corporation, CE Specialty Chemicals Incorporated, Kalama Chemicals Incorporated, Monsanto Company, Rohm & I faas Company, Schenectady Chemicals Incorporated, Texaco Chemical Company, and Uniroyal Chemical Company Incorporated, hereinafter referred to as the Alkyl Phenols and Ethoxylates (APE) Program Panel of the Chemical Manufacturers Assaci,it~o~ (CMA). The APE Program Panel has agreed to perform certain chemical fate and environmental effects tests on 4- nonylpheno). branched (4—NP) with CAS No. 84852—15--3~.

This chenucal substance is added to the list oftesting Consent Orders in 40 CFR ‘799.5000 for which ihe export notification requirements of40 CFR part707 apply.
EFFECTIVE DATE: February 21, 1990.
FOR FURTHER :NFORMATION CONTACT: Michael M. Stahl, Director, Environmental Assistance Division (TS— 799). Office ofToxic Substances, Rm. E5430. 401 Nt St., SW., Washington, DC 204’tO. (2L2~ 5~4 4~4.

TDI) (202) 55— 055t.
SUPPLEMENTARY INrct~uAT;oN: [tudor proc~’dures



### dt nbe’~ a 3() CFR part 790, theAPEP~gram

Rin’l ;as er.te~ed

into

a testing Consint Order with EPA. and has ng~’eed

to perfuim certain chemical fate and environmental effects tests for 4—NPwith CAS No. 84852_15_3* (Ref. 1). The Chemical Ahs~racts Service does not consider this rcgistry number (CAS No.) to represcr.t a unique chemical substance: therefore, this is denoted by

an asterisk (‘)

. For tlc~ purposec ofthis rulein accordance with section 3 ofthe Toxic Substance Control Act (TSCA), 

### 4— NP with CAS No 84352_15_3* is herein referred to as a chemical substanc2 comprised ofmostly pam-branched C9- aikylphenols. This rule amends 40 CFR 799.5000 by adding 4-NP to the list of chemical substances and mixtures subject to testin3 Consent Ortler~.

I. Recommendation
OnJuly 30, 1987, the Testing Priority Committee 

### (TPC) ofEPA formally nominated nony!phenol as a candidate for rulemaking underTSCA. The recommendation was based on the review ofa draft Chemical Hazard Information Profile (CHIP)and interaction between EPA and other Federal offices in a program review process. TheTPC did not detail specific testing recommendations with regard to the various forms ofnonylphenol (2-. 4-, monoethoxylated-, and polyethoxylated nonyiphenal) that were identified in the CHIP. The Cl-HP review was considered the first stage in the assessment ofrisk for “nonyiphenol.” Chemical information

wasprovided for 2-nonylphenol, normal (CAS No. 136-83-4), 4-nonylphenol. normal (CAS No. 104—40—5), and nonyiphenol. mixed isomers (CAS No. 25154—52—3); three distinct chemical entities. The TPC requested an investigation of the data gaps and environmental testing needs for nonylphenal. From the program review, EPA’s Office ofWater Regukitions and Standards (OWRS) recommended environmental effects testing, and the U.S. Food and Drug Administration (FDA) and t:PA’~

Office of Solid Waste (OSW) recornmend~~d

chemical fate testing. Following the

### TPC’s recorrimcndation to identify data ~ups ted testing needs, EPA initiated discussians with tndust:y manufacturers and other EPA offices.
II. Background

EPA issued a Federal Register nutice

on October21, 1987 (52 FR 39273), announcing the first public meeting and5992 Federal Register 

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EPA’s considorutiort ofdeveloping a testing Conscnt Order ora t*’st rule for nonyiphenol. The meeting convened on October27th, ~%‘l~r1

CMA announced the formation ofthe APE ProgramPanel. proposed the testing ofnortylphenol through a Consent Order, and indicated the APE ProgramPanel’s intent to conduct a voluntary environmental monitoring survey ofitonviphenol in addition to tests conducted pursuant to the Consent Order. Provisions ofthis multi-site survey, developed following consultation with EPA’s Exposure Evaluation Division in the Office of Toxic Substances, are not a part ofthis testing Consent Order and will not be addressed. However, theprotocol is available inthe public docket (Ref. 2). In response to questions raised during the October27th public meeting. the APE Program Panelsubmitted comments to EPA concerning information from the CHIP (Ref. 3) In summary, thePanel believed that the Chemical Abstracts Service (CAS) registry numbers for 2- nonyiphenol, 4-(normal) nonylphenol. and nonylphenol-mixed isomers previously reported by the manufacturers in the 1979 TSCA Inventory ofChemical Substances did
not now representthe correct commercially manufactured products on themarket today. The Panelbelieves that currently the commercial product that best represents “nonylphenol” is a chemical substance comprised of branched C9-alkyl phenols with CAS No. 84852_15_3*.The CHIPreported information for the normal-nonyl alkyl

chain isomers, which do not meet the current commercial product specifications. In addition, on January 14, 1988, EPA proceeded with delisting 2-nonylphenol from theTSCA Public Inventory (53 FR 949), since itwas no longer manufactured (Ref. 4~

As aresult. EPA has modified its original intention of requiring testing for nonylphenol-mixed isomers (CAS No. 25154—52—3). and is recommending that testing be conducted with the chemical substance comprised ofmostly pare-branched C9- alkylphenrils with CAS No. 84832-15—3’. hereinafter referred to as 4-NP.

III. Testing Consent OrderNegotiations
In the Federal Register ofFebruary 6. 1989 (54FR 6170). and in accordance with theprocedures established in

### 40 CFR 790.28. EPA requested persons interested inparticipating in or monitoring oftesting negotiations on 4— NP to contact theAgency by February 24. 1989. OnFebruary 13, 1989, EPA convened a second public meeting to discuss 4-NPtesting. Prior to this meeting. EPA drafted a testing Consent Order for 4-NP and submitted itto the APE Program Panel for review (Ref. 5) Subsequent meetings were convened to modify the draft testing Consent Order. OnJanuary 12, 1990, eight members of the APE ProgramPanel signed atesting Consent Order for 4—NP. The members agreedto performcertain chemical fate and environmental effects tests by specified dates according to thetest standards included in this Order. 

### IV. Production and Use
Technical grade 4—NP is produced by the liquid-phase alkylation ofphenol with propylene trimerin the presence of

an acid catalyst. Based on an aggregate report ofsales from the producers. 245.1 million pounds ofnonyiphenol were produced by eight U.S. companiesin 1987. Approximately 65 percent of nonylphenol is used as an intermediate in the production ofnonionic ethoxylated surfactants. In addition to its use as areactive Intermediate to produce ethoxylates for surfactant use. nonyiphenol is used as areactive intermediate in otherindustrial applications: Lube additives (appropriately 15 percent); formakiehvde resins. puivrneric stabilizers, and epoxyresins (collectiveiy eccounting for approximately 18 percent of nonylphenol enduse): and, to a h’sser extent, (approximately <10 percent) in themanufacture ofphosphate antioxidants, oil additives,synthetic lubricants, and corrosion inhibitors. 

### V. Testing Program
EPA will use the data generated by these tests to determine the chemical fate of4—NP andpotential environmental risks associated with the manufacture, use, and disposal of4-NP. OWRS intends to utilize these data to issue water quality advisories for the protection of aquatic organisms. OSW and the FDA intend to utilize these data in a risk analysis and evaluation of chemical fate as part ofprogram reviews.
A. GhemicalFate High levels ofunspecified nonylphenol were reported in stabilized sewage sludge containingsurfactants, suggesting that the point oforigin of4— NP Is from anaerobic degradation of alkylphenol ethoxylates. Several studies have identified nonylphenols in ~secondary effluents from municipal, treatment plants or in rivers receiving
wastewater fromvarious chemical industries. The APEProgram Panelhas agreed to determine the following physical and chemical properties of4-NP’ Boiling point, melting point, dissociation constant, partition coefficientand vapor pressure. The APE ProgramPanel has agreed to also measure the water solubility of4-NP in freshwater and saltwater. The APE Program Panelhas agreed to develop the following chemical fate data: Sediment adsorption isotherm, anaerobic biodegradation. and aerobic microcosm biodegradation as

seen in the following table.

TABLE—TESTING REQUIRED FOR 4-NONVLPHENOt., BRANCHED

Test Test standards in
‘ Stall 40 CFR date’

Tier I: Env,roomental Effects Tests: Algae bioasSay, Seleeastnjm sp. and Skelotorvemasp

.. Acute toxicity, st~eepsheadminnow

.. ., - Acute toxicity. mysid stirirnp

-
.. .. Bioconcentration. tatt~oadmsnnow

-
.. ct~ernicat

Fate Tests: Botlsng point

... .. ,,,~.. Melting point

.. ., .. Dissociation constant

.. .. .. Partition coefficient

.. .. - ,. Water solubility

- — Vapor pressure
....~
.. Sediment adsorption isomerm

.. ...._ :.

.. .~
... Anaerobic biodegradation

.. ..... _. -
.. .... §797.1050 § 797.1400 §797.1930
*797.1520

§796.1220 CG 1300 § 796.1370 §796.1550 §196.1860 § 796.1950 § 796.2750 §796.3140 Final report date

9

9 9 Is

8 & 8 S 6 6 6 12 3 3 3 6

3 3 .3 3 3 3 3 9Federal Register .1 VoL 55, No. 35 

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## / Rules and Regulations 5993

~~----~_--—_—--.-~_-__-_. —---=-- .—-— —.-—-—--.~- ——_______ TABLE—TESTING REQUtPED FOR 4-NONVLPHENOL, BRANCHED—Continued

- Test Test s’ardards in Start [‘‘~treport

40 CFR oate’ date

~robc m.~rocosm

b.odegladatlon

‘ B.)urt~,n 3 12 Tier II:

~—~1rorimental

Effects Tests: Ct’.ror”c toxicity, Invertebate § 797 1330 6 15 §797.1~)50 6 15 F,sh early life stage”

- § 797.1600 ‘1 6 15 Benth.c sediment bioassay. fridge

- EPA protocol i” 18 Sentri,c sediment bioassay, tadpole EPA protocol 6 18

Number ul rnor’ms afterthe efiectr~e date of the Consent Orderor the completion of Tier I test(s). Njmr.ec of mortr.S after the effective nate of the Consent Order. Interim t6-month) prc,gress repo:ts shall be sub’vr’t.~dto E1~Afor all tests having fin~t report

~ of greslerthan 9 months, starting 6 months afterthe startdate. Chemical Guideline (CG) 1300 is appendedto the testing Consent Order for 4-NP. Bourquin et at. (1977) is appended to the testingConsent Oroer for4—NP. Dao”nia macna (~

797 1330) or mysid shrimp (~ 797.1950) wilt be setectad as the lest species, based on sensitivity to 4-NP during acute tox’cty testir3.
or sheepshead minnow wIt be selected as the test species. b5sedon sensitisty to 4—NP during acute to~clty testing The cr”oi”r’tid sediment tosiclty test guideline is appended to thetesting Consent Order he 4-NP. The .~iooie;

sediment subchron,c to,”cit~ test guideline is 4ppended to thetesting Cor.s,~nt Order for4—NP.

13. En‘.‘ironnwntulEffucts Nonylphenols ofdifferent structure arid purity’ than 4-NP are highly toxic to aquatic organisms (CHIP). The4—NP 96- hour fathead minnow LC3O value was 0.30 mg/L (Ref. 6). The 4-NP 4-I-hour Dap/inia inagno EC5O value was 0.44 rn~/L (~ef. 7). Acute toxicity testing of 4-NP in algae and marine orgdnisms (sheepshead minnow and mysid si~rimp), and biaconcentration testing in fish, will be sponsored by the APE Program Panel. The APE Program Panel and EPA have agreedto a tiered testing program described in the Table in Unit V.A. of this preamble. All tests are required; the tiering is necessary for species selection for the aquatic invertebrate chronic toxicity and the fish early life stage ti’sts. TheAPE Program Panel agrees to perforni the testing according to cited EPA test standards and specified test schedules presented in the Table in unit V.A. TierI testing will be completed within 18 months, and interim status reports are due in 6-month increments for tests with final report dates due 9 months or more after the effective date ofthe testing Consent Order. TierII testing will be completed in 18 months, with interim status reports due in 6- month increments after the start ofeach t,’st.
C. Test ~ub.s~ance EPA recognizes that the chemical substance, 4—NP, is a commercial mixtiir~ containing up to 95 percent of the branched poro-nonylphenol isomer. The commercial production of4-NP does not result in a single pure chemical entity. Moreover, low-voltime, highpurity laboratory synthesis would, most likely, not produce a material comparable to’ the commercial mixture. Industrially prodttced 4--NP, both technical and high-purity grades. is a mixture ofseveral components. The predominant components ofcommercial 4—NP arepara-branched C9- alkylphcr.ols (95 to 96percent) which differonly in thebranched configuration ofthe C9-alkyl chain.The remaining components consist ofortho-branched C9-alkylpherrnls (approximately 2 to 3 percent). di-nonyiphenol (less than0.01 percent), andphenol/propylene trimer (less than 0.03 percent) (Ref

### 8). The synthetic process involves a multicomponent system with impurities present in the feedstocks. Separation of the individual impurity components with chromatographic techniques in order to purify the final 4-NPproduced may resultin a product which is not indicative ofthe4-NPmixture commerciallyproduced. Therefore, testing will be conducted using anon

radiolabelled, high-puritygrade, uldustrially produced 4-NP at a95 percent purity level.


### VI. Export Notification

The issuance ofthis testing Consent Order subjectsany person who exports

or intends to exportthe chemical substance, 4-NP with CAS No. 84852—
15—3” at anypurity grade, to the export notification requirements of section 12(b) ofTSCA. The specific requirements are listed in 40 CFR part 707. Chemicals subject to testing Consent Orders are listed at40 CFR 799.5tX~J. This listing serves as notification to persons who export or intend to export the chemical substance which is the subject ofthis testing Consent Order that 40 CFR part707 applies.
VII. Rulemaking Record

EPA has established a record for this considered by EPA in developing this Consent Order. This record includes the following information:
A. Supporting Documentation (1) Testing Consent Orderfor 4—NP. (2) Federal Registernotices perta~niitg
to this notice and consent order consisting of: (a) Notice soliciting interested partiat for developing a consent order for nonylphenol, mixed isomers, and possibly 2- and 4-nor.ylphenol (October 21, 1987; 52 FR 39273). (b) Notice announcing public meeting for February 13, 1969, and soliciting interestedparties for developing a consent order for 4-nonyiphenol, branched (4—NP) (February 8, 1989; 54 FR 6170). (c) Notice ofintent to remove incorrectly reported chemical substances from the TSCA Inventory (January 14, 1988; 53 FR 949). (3) Communications consisting of: (a) Written letters. (b) Contactreports oftelephone conversations. (c) Meeting summaries. (4) Reports—published and unpublished factual materials including: Chemical Hazard Information Profile (CII1P)—Nonylphenol 25154—52—3 (draft). EPA Office ofToxic Substances, Existing Chemical Assessment Division. (September 17, 1985).

B. Iief.9rr’ncc’S
(1) CA fit.~

computer search, completed May20. 1988. (2)Clieniical M.inuf~cturersAssociation (UMA). Coverletter to “Environmental Monstor~ng

and Modeling Studies”, from Geraldine V. Cox to SarahShapley (Expoture Evaluation Di~ision),

Environment.iI Protection Agency (EPA: March 16. 19110). Includes attachment “Environmental rule (docketnumber OPTS—42104B). This ~amp!ing and An.il~’si~

for Nonylphenul record contains the information

. Fthiixyfate Sps’i:ii’s in the Alabama and,it194 Federal Register 

## / Vol. 55, No. 35 

## I Wednesday, February 21, 1990 

## / Rules and Regulations

.,‘.~ eavr Ri 1’rs, prcp~irm’m1fur ?f’t Alkyi Phenuls arid Ethos~i.itu’s (At~1i t’rigrun $‘iiel. )F’tmru~ir 1989). t~’i CMr\. titter with attomi’ ii nonyiphinol report on CASnomliers and structures. from henry J. Summer(APE Prottram l’mmnet M,mnager) to Y~’e tte 111,1lv*’r (Test Rules I 1,vi’topne’n Branch). EPA. (May 11, 1988). (4) CM\. July 5. 1088. coverti’tter kim Schiunmctmidy Chemicals. Inc.. t’rom ttmnry I

Sauer IAPE Prrigrmmnt Panel Manager) to Ilenrv P. I au (Chime r:aI lrive’rttory S,,ct ion). EPA. (July 13. 1988). (5) EPA. Letter with at tachr’d nraft tisIing Consetit Order from Yvette P. Uellyer(Test Rules Development Branch) toHenry J. Snuer, CM~\.

(February 3, 1989). (Ii) Mutoanto Industrial Chemicals Company. Static Acute Bioassay Report ~26822. Analytical [ho Chemistry Laboratories. (February 3.1981). (7) Calvert. C.. andAdams. W. J. “Acute toxicity ofnonylphenol’ to Dophnianragna.” Monsanto Industrial Chemicals Company. Report No. F.S—81—SS—19. (June 8. 1981).. (8) Yunick, R. Technical DataReport for para-nony)phenol. CASNo. 84852-15—3, presented at EPA Ifeadqmarters. Washington. DC. (June 14.1988),
Confidential BUSIOOSS Information (CBI), whilepart ofthe record, is not available for publicreview. A public version oftherecord, from whichC131 has been deleted, is available for inspection in theTSCA Public Docket Office. Rm. NE—G004. 401 M St.. SW.. Washington, DC. from 8 a.m. to -1 p.m.. Monday through Friday. except legal holidays.

VIII. Other Regulatory Requirements Pupt~’ru’orh

ReductionAct
The Office ofManagement and Budget (0MB) has approved the information collection requirements contained in this rule under the provisions ofthe Paperwork ReductionAct of1980.44 U.S.C. 3501 etseq., andhas assigned 0MB Controlnumber2070-0033. Public reportingburden for this collection ofinformation is estimated to average900 hours per response. The estimates include time for reviewing instructions, searching existing data
sources, gathering and maintaining the data needed, and completing and reviewing the collection ofinformation. Send comments regarding theburden estimate orany other aspect ofthis collection ofinformation, including suggestions for reducing this burden to. Chief. Information Policy Branch. PM— 223, US Environmental Protection Agency, 401 M St.. SW.. Washington. DC 2(1460: and the Office (ifM~iiiagemnnt and Budget. Paperwork Reduction Project 12t)70—003tl. Washington. DC 20503.
List ofSubjects in 40 CFR Part 799

Chemicals. Chemical export, Chemical fate. Environmental effects. Environmental protection, lIazardous substances. Laboratories. Recordkeepingandreporting requirements. l’esting.
Dated: February 3. 1990. Linda J. Fisher, ,lssertap(A.’Imi’nistra(or

forPest/cri/n’sand Th.ricSubstances. Therefore. 40 CER part 799 is amended

as follows:

PART 799—EAMENDEDJ

I. The authority citation for part 79~1 continues to read as follows: Autho~’ity:

15 U.S.C. 2603. 2611. 2625.
2. Section 799.5000 is amended by adding 4—NP to thetable in CAS Numberorder, to read as follows:
§ 799.5000 Testing consent orders.

JFRDoc. 90-3965 Filed2—20—9th 8:45 amj

CAS No. Substance or mistume name Testing FR citation

84852-15-3’ 4-Nonytphenot. branched J~~ternscal Envwonmentat eftects..._

..........._ ...~..._. fate..._

..._.... .. 2/2111990 2/21/1990

BIWNG CODE 5560-50-0