Federal Registor / Vol. f’5. No. 35 / ~Vednesdjv, February 21. 1990 I Pu.cs aod Reou~ations 5991

40 CFR Part 799

IOPTS—42104B; FAL 3661-41

RIN 2070-AB07

Testing Consent Order On 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 of testing

Consent Orders in 40 CFR ‘799.5000 for

which ihe export notification

requirements of 40 CFR part 707 apply.

EFFECTIVE DATE: February 21, 1990.

FOR FURTHER :NFORMATION CONTACT:

Michael M. Stahl, Director,

Environmental Assistance Division (TS—

799). Office of Toxic 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~’duresdt nbe’~ a 3() CFR part 790,

the APE P~gramRin’l ;as er.te~edinto

a testing Consint Order with EPA. and

has ng~’eedto perfuim certain chemical

fate and environmental effects tests for

4—NP with CAS No. 84852_15_3* (Ref. 1).

The Chemical Ahs~ractsService 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

rule in accordance with section 3 of the

Toxic Substance Control Act (TSCA), 4—

NP with CAS No 84352_15_3* is herein

referred to as a chemical substanc2

comprised of mostly 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

On July 30, 1987, the Testing Priority

Committee (TPC) of EPA formally

nominated nony!phenol as a candidate

for rulemaking under TSCA. The

recommendation was based on the

review of a draft Chemical Hazard

Information Profile (CHIP) and

interaction between EPA and other

Federal offices in a program review

process. The TPC did not detail specific

testing recommendations with regard to

the various forms of nonylphenol (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 of Water 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~~dchemical fate

testing.

Following the TPC’s recorrimcnda tion

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 October 21, 1987 (52 FR 39273),

announcing the first public meeting and
5992 Federal Register / Vol. 35. No. 35 I Wednesday. February 21, 19th.) / Rules an(1 Regulations

EPA’s considorutiort of developing a

testing Conscnt Order or a t*’st rule for

nonyiphenol. The meeting convened on

October 27th, ~%‘l~r1CMA announced the

formation of the APE Program Panel.

proposed the testing of nortylphenol

through a Consent Order, and indicated

the APE Program Panel’s intent to

conduct a voluntary environmental

monitoring survey of itonviphenol in

addition to tests conducted pursuant to

the Consent Order. Provisions of this

multi-site survey, developed following

consultation with EPA’s Exposure

Evaluation Division in the Office of

Toxic Substances, are not a part of this

testing Consent Order and will not be

addressed. However, the protocol is

available in the public docket (Ref. 2).

In response to questions raised during

the October 27th public meeting. the

APE Program Panelsubmitted comments

to EPA concerning information from the

CHIP (Ref. 3) In summary, the Panel

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

the market 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 CHIP reported

information for the normal-nonyl alkylchain isomers, which do not meet the

current commercial product

specifications.

In addition, on January 14, 1988, EPA

proceeded with delisting 2-nonylphenol

from the TSCA Public Inventory (53 FR

949), since it was no longer

manufactured (Ref. 4~As a result. 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

of mostly pare-branched C9-

alkylphenrils with CAS No. 84832-15—3’.

hereinafter referred to as 4-NP.

III. Testing Consent OrderNegotiations

In the Federal Register of February 6.

1989 (54 FR 6170). and in accordance

with the procedures established in 40

CFR 790.28. EPA requested persons

interested in participating in or

monitoring oftesting negotiations on 4—

NP to contact the Agency by February

24. 1989. On February 13, 1989, EPA

convened a second public meeting to

discuss 4-NP testing. Prior to this

meeting. EPA drafted a testing Consent

Order for 4-NP and submitted it to the

APE Program Panel for review (Ref. 5)

Subsequent meetings were convened to

modify the draft testing Consent Order.

On January 12, 1990, eight members of

the APE ProgramPanel signed a testing

Consent Order for 4—NP. The members

agreed to perform certain chemical fate

and environmental effects tests by

specified dates according to the test

standards included in this Order.

IV. Production and Use

Technical grade 4—NP is produced by

the liquid-phase alkylation of phenol

with propylene trimer in the presence of

an acid catalyst. Based on an aggregate

report ofsales from the producers. 245.1

million pounds of nonyiphenol were

produced by eight U.S. companiesin

1987.

Approximately 65 percent of

nonylphenol is used as an intermediate

in the production of nonionic

ethoxylated surfactants. In addition to

its use as a reactive Intermediate to

produce ethoxylates for surfactant use.

nonyiphenol is used as a reactive

intermediate in other industrial

applications: Lube additives

(appropriately 15 percent);

formakiehvde resins. puivrneric

stabilizers, and epoxy resins

(collectiveiy eccounting for

approximately 18 percent of

nonylphenol end use): and, to a h’sser

extent, (approximately <10 percent) in

the manufacture of phosphate

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 of 4—NP and potential

environmental risks associated with the

manufacture, use, and disposal of 4-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 of program

reviews.

A. GhemicalFate

High levels of unspecified

nonylphenol were reported in stabilized

sewage sludge containingsurfactants,

suggesting that the point of origin of 4—

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 APE Program Panel has agreed to

determine the following physical and

chemical properties of 4-NP’ Boiling

point, melting point, dissociation

constant, partition coefficient and vapor

pressure. The APE Program Panel has

agreed to also measure the water

solubility of 4-NP in freshwater and

saltwater. The APE Program Panel has

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 Skelotorvema sp ..

Acute toxicity, st~eepsheadminnow .. ., -

Acute toxicity. mysid stirirnp - .. ..

Bioconcentration. tatt~oadmsnnow - ..

ct~ernicatFate 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

9
Federal Register .1 VoL 55, No. 35 I Wednesday, February 21. 1990 / 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.~rocosmb.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 after the efiectr~edate of the Consent Order or 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~treport

~ of gresler than 9 months, starting 6 months after the start date.

Chemical Guideline (CG) 1300 is appended to the testing Consent Order for 4-NP.

Bourquin et at. (1977) is appended to the testing Consent Oroer for 4—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. b5sed on sensitisty to 4—NP during acute to~cltytesting

The cr”oi”r’tid sediment tosiclty test guideline is appended to the testing Consent Order he 4-NP.

The .~iooie;sediment subchron,c to,”cit~test guideline is 4ppended to the testing Cor.s,~ntOrder for 4—NP.

13. En‘.‘ironnwntulEffucts

Nonylphenols of different structure

arid purity’ than 4-NP are highly toxic to

aquatic organisms (CHIP). The 4—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 agreed to 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. Tier I 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

of the testing Consent Order. Tier II

testing will be completed in 18 months,

with interim status reports due in 6-

month increments after the start of each

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 of 4-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 of commercial

4—NP are para-branched C9-

alkylphcr.ols (95 to 96 percent) which

differonly in the branched configuration

of the C9-alkyl chain.The remaining

components consist of ortho-branched

C9-alkylpherrnls (approximately 2 to 3

percent). di-nonyiphenol (less than 0.01

percent), and phenol/propylene trimer

(less than 0.03 percent) (Ref8). 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-NP produced may

result in a product which is not

indicative of the 4-NPmixture

commercially produced. Therefore,

testing will be conducted using a nonradiolabelled, high-purity grade,

uldustrially produced 4-NP at a 95

percent purity level.

VI. Export Notification

The issuance of this testing Consent

Order subjectsany person who exports

or intends to export the chemical

substance, 4-NP with CAS No. 84852—

15—3” at any purity grade, to the export

notification requirements of section

12(b) of TSCA. The specific

requirements are listed in 40 CFR part

707. Chemicals subject to testing

Consent Orders are listed at 40 CFR

799.5tX~J.This listing serves as

notification to persons who export or

intend to export the chemical substance

which is the subject of this testing

Consent Order that 40 CFR part 707

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 Register notices 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

interested parties 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) Contact reports 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

May 20. 1988.

(2) Clieniical M.inuf~cturersAssociation

(UMA). Cover letter to “Environmental

Monstor~ngand Modeling Studies”, from

Geraldine V. Cox to Sarah Shapley (Expoture

Evaluation Di~ision),Environment.iI

Protection Agency (EPA: March 16. 19110).

Includes attachment “Environmental

rule (docketnumber OPTS—42104B). This ~amp!ingand 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~1it’rigrun

$‘iiel. )F’tmru~ir 1989).

t~’iCMr\. titter with attomi’ ii nonyiphinol

report on CAS nomliers and structures. from

henry J. Summer (APE Prottram l’mmnet M,mnager)

to Y~’et te 111,1 lv*’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 ISauer I APE Prrigrmmnt Panel Manager) to

Ilenrv P. I au (Chime r:a I lrive’rttory S,,ct ion).

EPA. (July 13. 1988).

(5) EPA. Letter with at tachr’d nra ft tisIi ng

Consetit Order from Yvette P. Uellyer(Test

Rules Development Branch) to Henry J.

Snuer, CM~\.(February 3, 1989).

(Ii) Mutoanto Industrial Chemicals

Company. Sta tic Acute Bioassay Report

~26822. Analytical [ho Chemistry

Laboratories. (February 3.1981).

(7) Calvert. C.. and Adams. W. J. “Acute

toxicity of nonylphenol’ to Dophnia nragna.”

Monsanto Industrial Chemicals Company.

Report No. F.S—81—SS—19. (June 8. 1981)..

(8) Yunick, R. Technical Data Report for

para-nony)phenol. CASNo. 84852-15—3,

presented at EPA Ifeadqmarters. Washington.

DC. (June 14.1988),

Confidential BUSIOOSS Information

(CBI), while part ofthe record, is not

available for public review. A public

version of the record, from which C131

has been deleted, is available for

inspection in the TSCA 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’orhReduction Act

The Office of Management and Budget

(0MB) has approved the information

collection requirements contained in this

rule under the provisions ofthe

Paperwork Reduction Act of 1980.44

U.S.C. 3501 et seq., and has assigned

0MB Control number 2070-0033.

Public reporting burden for this

collection of information is estimated to

average 900 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 the burden

estimate or any other aspect ofthis

collection of information, 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 (if M~iiiagemnnt

and Budget. Paperwork Reduction

Project 12t)70—003tl. Washington. DC

20503.

List of Subjects in 40 CFR Part 799

Chemicals. Chemical export, Chemical

fate. Environmental effects.

Environmental protection, lIazardous

substances. Laboratories.

Recordkeeping and reporting

requirements. l’esting.

Dated: February 3. 1990.

Linda J. Fisher,

,lssertap( A.’Imi’nistra(orforPest/c ri/n’s and

Th.ric Substances.

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 the table in CAS

Number order, to read as follows:

§ 799.5000 Testing consent orders.

JFRDoc. 90-3965 Filed 2—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