Federal Register / Vol. 53, No. 221 / Wednesday, November 16, 1988 / Notices

ENVIRONMENTAL PROTECTION

AGENCY

(OPTS-41030; FRL-3476-61

Twenty-Third Report of the

Interagency Testing Committee to the

Administrator, Receipt of Report and

Request for Comments Regarding

Priority List of Chemicals

AGENCY: Environmental Protection

Agency (EPA).

ACTION: Notice.

SUMMARY: The Interagency Testing

Committee (ITC), established under

section 4(e) of the Toxic Substances

Control Act (TSCA), transmitted its

Twenty-Thiird Report to the

Administrator of EPA on November 1,

1988. This report, which revises and

updates theCommittee's priority list of

chemicals, adds six chemicals to the list

for priority consideration by EPA in

promulgation of test rules under section

4(a) of the Act. The Twenty-Third

Report is included with this notice, The

new chemicals are tris(2-chloroethyl)-

phosphate (CAS No. 115-96-8), three

tris(2-chloropropyl)-phosphate, (CAS

Nos. 6145-73-9,13674-84-5, and 13674-

87-8), tetrakis(2-chloroethyl)-ethylene

diphosphate (CAS No. 33125-86-9) and

butyraldehyde (CAS No. 123-72-8).

These chemicals are not designated for

response within 12 months.

Crotonaldehyde (CAS No. 4170-30-3),

which was recommended with intent-todesignate by the ITC in its TwentySecond Report (53 FR 18196; May 20,

1988), now is designated for response

within 12 months. In response to ITC's

designation, EPA will either initiate

rulemaking under section 4(a) of TSCA.

or publish a Federal Register notice

explaining the reasons for not initiating

such rulemaking within 12 months. EPA

invites interested persons to submit

written comments on the report, and to

attend Focus Meetings to help narrow

and focus the issues raised by the ITC's

recommendations.

Additionally, EPA is soliciting interest

in public participation in the consent

agreement process for tris(2-

chloroethyl)-phosphate, three tris(2-

chloropropyl)-phosphates, and

tetrakis(2-chloroethyl)-ethylene

diphosphate.

The ITC also has removed two

chemicals, ethylbenzene and methyl

ethyl ketoxime, from the priority list.

DATES: Written comments should be

submitted by December 16, 1988. Submit

written notice of interest in being

designated an "interested party" to

development of consent agreements for

tris(2-chloroethyl)-phosphate, three

tris(2-chloropropyl)-phosphates and

tetrakis(2-chloroethyl)-ethylene

diphosphate by December 16, 1988.

Focus Meetings will be held on

December 13, 1988.

ADDRESS: Send written submissions to:

TSCA Public Docket Office (TS-793),

Office of Toxic Substances,

Environmental Protection Agency, Rm.

NE G-004, 401 M Street SW.,

Washington, DC 20460.

Submissions should bear the

document control number (OPTS-41030).

The public record supporting this

action, including comments, is available

for public inspection in Rm. NE G-004 at

the address noted above from 8 a.m. to 4

p.m., Monday through Friday, except

legal holidays.

The Focus Meetings will be held at

EPA Headquarters, Rm. 103 NE Mall, 401

M Street SW., Washington, DC. Persons

planning to attend the Focus Meetings,

and/or seeking to be informed of

subsequent public meetings on these

chemicals, should notify the TSCA

Assistance Office at the address listed

below. To ensure seating

accommodations at the Focus Meetings,

persons interested in attending are

asked to notify EPA at least one week

ahead of the schedule date.

FOR FURTHER INFORMATION CONTACT

Michael M. Stahl, Director, TSCA

Assistance Office (TS-799}, Office of

Toxic Substances, Environmental

Protection Agency, 401 M Street, SW.,

Washington, DC 20460, (202) 554-1404,

TDD (202) 554--0551.

SUPPLEMENTARY INFORMATION: EPA has

received the TSCA Interagency Testing

Committee's Report to the

Administrator.

I. Background

TSCA (Pub. L. 94-469,90 Stat. 2003 et

seq; 15 U.S.C. 2601 et seq.) authorizes

the Administrator of EPA to promulgate

regulations under section 4(a) requiring

testing of chemical substances and

mixtures in order to develop data

relevant to determining the risks that

such chemical substances and mixtures

may present to health and the

environment. Section 4(e) of TSCA

established an Interagency Testing

Committee to make recommendations to

the Administrator of EPA on chemical

substances and mixtures to be given

priority consideration in proposing test

rules under section 4(a). Section 4(e)

directs the ITC to revise its list of

recommendations at least every 6

months as necessary. The ITC may

"designate" up to 50 substances and

mixtures at any one time for priority

consideration by the Agency.

.Crotonaldehyde is a designated

chemical. For such designations, the

Agency must within 12 months either

intitiate rulemaking or issue in the

Federal Register its reasons for not

doing so. The ITC's Twenty-Third

Report was received by the

Administrator on November 1,1988, and

follows this Notice. The Report adds six

substances to the TSCA section 4(e)

priority list.

IL Written and Oral Comments and

Public Meetings

EPA invites interested persons to

submit detailed comments on the ITC's

new recommendations. The Agency is

interested in receiving information

concerning additional or ongoing health

and safety studies on the subject

chemicals as well as information

relating to the human and environmental

exposure to these chemicals.

A notice is published elsewhere in

today's Federal Register adding the

substances recommended in the ITC's

Twenty-Third Report to the TSCA

section 8(d) Health and Safety Data

Reporting Rule (40 CFR Part 716), which

requires the reporting of unpublished

health and safety studies on the listed

chemicals. These chemicals also will be

added to the TSCA section 8(a)

Preliminary Assessment Information

Rule (40 CFR Part 712) published

elsewhere in this issue. The section 8(a)

rule requires the reporting of production

volume, use, exposure, and release

information on the listed chemicals.

Focus Meetings will be held to discuss

relevant issues pertaining to these

chemicals and to narrow the range of

issues/effects which will be the focus of

the Agency's subsequent activities in

responding to the ITC recommendations.

The Focus Meetings will be held on

December 13, 1988, as follows:

9:30 a.m. Tris(2-chloroethyl)-phosphate,

three tris(chloroprophyl)-phosphates,

and tetrakis(2-chloroethyl)-ethylene

disphosphate

1:00 p.m. Butyraldehyde

They will be held at EPA

Headquarters, Rm. 103 NE Mall, 401 M

St., SW., Washington, DC. These

meetings are intended to supplement

and expand upon written comments

submitted in response to this notice.

Persons wishing to attend these

.meetings, or subsequent meetings on

these chemicals, should call the TSCA

Assistance Office at the telephone

number listed above at least one week

in advance. ,

This notice also serves to invite

persons interested in participating in or

monitoring negotiations for consent

agreements for tris(2-chloroethyl)-

46262 46262
Federal Register / Vol. 53, No. 221 / Wednesday, November 16, 1988 / Notices

phosphate, three tris(chloropropyl)-

phosphates, and tetrakis(2-chloroethyl)-

ethylene diphosphate to notify EPA no

later than December 16, 1988. The

procedures for negotiations are

described in 40 CFR 790.22. All written

submissions should bear the identifying

docket number (OPTS-41030).

III. Status of List

In addition to adding the six

recommendations to the priority list, the

ITC's Twenty-Third Report notes the

removal of two chemicals from the list.

Ethylbenzene has been removed from

the list because the data gaps previously

identified by the ITC have been

satisfactorily resolved. Subsequent to

ITC's preparation of its Twenty-Second

Report, EPA responded to the ITC's

recommendation for methyl ethyl

ketoxime by publishing a Notice of

Proposed Rulemaking in the Federal

Register (53 FR 35838; September 15,

1988). The current list contains two

designated substances, five chemicals

recommended with intent-to-designate,

and fourteen recommended substances.

Authority: 15 U.S.C. 2603.

Dated: November 4, 1988.

Joseph J. Merenda,

Director, Existing Chemical Assessment

Division. -

TWENTY-THIRD REPORT OF THE

TSCA INTERAGENCY TESTING

COMMITTEE TO THE

ADMINISTRATOR,

ENVIRONMENTAL PROTECTION

AGENCY

Summary

Section 4 of the Toxic Substances

Control Act of 1976 (TSCA, Pub. L 94-

469) provides for the testing of

chemicals in commerce that may present

an unreasonable risk of injury to health

or the environment. It also provides for

the establishment of a Committee (ITC),

composed of representatives from eight

designated Federal agencies, to

recommend chemical substances and

mixtures (chemicals) to which the

Administrator of the U.S. Environmental

Protection Agency (EPA) should give

priority consideration for the

promulgation of testing rules.

Section 4(e)(1)(Al of TSCA directs the

Committee to recommend to the EPA

Administrator chemicals to which the

Administrator should give priority

consideration for the promulgation of

testing rules pursuant to section 4(a).

The Committee is required to designate

thosa chemicals, from among its

recommendations, to which the

Administrator should respond within 12

months by either initiating a rulemaking

proceeding under section 4(a) or

publishing the Administrator's reason

for not initiating such a proceeding. At

least every 6 months, the Committee

makes those revisions in the TSCA

section 4(e) Priority List that it

determines to be necessary and

transmits them to the EPA

Administrator.

As a result of its deliberations, the

Committee is revising the TSCA section

4(e) Priority List by the addition of 6

chemicals.

The Priority List is divided into three

parts: Part A contains those

recommended chemicals and groups

designated for priority consideration

and response by the EPA Administrator

within 12 months. Part B contains

chemicals and groups of chemicals

recommended with intent-to-designate.

This category was established by the

Committee in its seventeenth report (50

FR 47603; November 19, 1985) to take

advantage of rules promulgating

automatic reporting requirements for

non-designated ITC recommendations

under the section 8(a) Preliminary

Assessment rule and the TSCA section

8(d) Health and Safety Data Reporting

rule. Information received following

recommendation with intent-todesignate may influence the Committee

to either designate or not designate the

chemicals or groups of chemicals in a

subsequent report to the Administrator.

Part C contains chemicals and groups of

chemicals that have been recommended

for priority consideration by EPA

without being designated for response

within 12 months. The changes to the

Priority List are presented, together with

the types of testing recommended, in the

following Table 1:

TABLE 1.-ADDITIONS TO THE SECTION

4(E) PRIORITY LIST

[November 1988]

Chemical/Group Recommended studies

A. Designated for

response whn12

months:

Crotonaldehyde'

CAS No. 4170-

30-3.

B. Recommended with

Intent-to-Designate:

Tris(2-chloroethyl)-

phosphate I CAS

No. 115-96-8.

Chemical Fate:

Volatilization rate from

water aerobic aquatic

biodegradation rate.

Health Effects: None.

Ecological Effects: Acute

toxicity to algae, fish

and aquatic

invertebrates.

Chemical Fate:

Environmental

monitoring; vapor

pressure;

biodegradation.

Health Effects: None.

TABLE 1.-ADDITIONS TO THE SECTION

4(E) PRIORITY LIST-Continued

[November 1988]

Chemical/Group I Recommended studies

Tris(chloropropyl)- phosphates.

including the

following:

Tris(2-chloro-1- propyl)

phosphate 3

CAS No. 6145-

73-9

Tris(1-chloro-2-

propyl)

phosphate

CAS No.

13674-84-5;

and

Tris(1,3-dichloro-2-

propyl)

phosphate 3 CAS

No. 13674-87-8.

Tetrakis(2-chloroethy)-

ethylene

diphosphate 0 CAS

No. 33125-86-9.

C. Recommended

Without Being

Designated for

Response Within t2

Months:

Butyraldehyde 7

CAS No. 123-72-

8.

Ecological Effects: Acute

toxicity to aquatic and

terrestrial plants

chronic toxicity to fish.

Chemical Fate:

Environmental

monitoring; water

solubility; vapor

pressure; octanol/

water partition

coofficient; ,

biodegradation.

Health Effects: Acute

and subchronic

effects, including

cholinesterase

inhibition, 90-day

subchronic effects and

reproductive effects.

Health effects

recommendations

apply only to CAS

No% 6145-73-9 and

13674-84-5.

Ecological Effects: Acute

toxicity to fish, aquatic

invertebrates and

algae; chronic toxicity

to fish.

Chemical Fate:.

Environmental

monitoring; water

solubility; vapor

pressure; octanol/

water partition

coefficient

biodegradation.

Health Effects: None.

Ecological Effects: Acute

toxicity to fish, algae

and aquatic

invertebrates.

Chemical Fate:

Monitoring in the

vicinity of major

manufacturing and use

sites.

Health Effects: In depth

toxicology evaluation if

warranted by

monitoring data.

Ecological Effects:

Toxicity studies with

representative blots if

warranted by

monitoring data.

CA Index Names (9 Cl)

1. 2-Butenao

2. Ethanol, 2-chloro-, phosphate (3:1)

3. 1-Propanol,2-chloro-, phosphate (3:1)

4. 2-Propanol,1 -chioro-, phosphate (3:1) 5. 2-Propanot,l,.3-dichtoro., phosphate (3:1)

6. Phosphoric acid,t,2-ethanedly! tetrakis(2chnloroethyl) ester

7. Butanal

46263
Federal Register / Vol. 53, No. 221 / Wednesday, November 16, 1988 / Notices

Note: Crotonatdehyde was recommended with

Intent-to-designate by the Committee in the twentysecond report (53 FR 18196; May 20, 1988).

TSCA Interagency Testing Committee

Statutory Member Agencies and Their

Representatives

Council on Environmental Quality

William Mills, Member 1

Department of Commerce

Patrick D. Cosslett, Member

Raimundo Prat, Alternate

Environmental Protection Agency

John D. Walker, Member

Laurence S. Rosenstein, Alternate

National Cancer Institute

Richard Adamson, Member

Elizabeth K. Weisburger, Alternate

National Institute of Environmental

Health Sciences

James K. Selkirk, Member and'

Chairperson

National Institute for Occupational

Safety and Health

Bryan D. Hardin, Member and Vice

Chairperson

Rodger L. Tatken, Alternate

National Science Foundation

Rodger W. Baier, Member

Jarvis L. Moyers, Alternate

Occupational Safety and Health

Administration

Robert Turnage, Member

Stephen Mallinger, Alternate

Liaison Agencies and Their

Representatives

Consumer Product Safety Commission

Lakshmi C. Mishra

Department of Agriculture

Richard M. Parry, Jr.

Elise A. B. Brown

Department of Defense

Harry Salem 2

Melvin E. Anderson 2

Department of the Interior

Gregory J. Smith 3

Martha L. Gay 4

Food and Drug Administration

Arnold Borsetti

National Library of Medicine

Vera Hudson

National Toxicology Program

Dorothy Canter

Committee Staff

Robert H. Brink, Executive Secretary

Norma Williams, ITC Program Specialist

Support Staff

Alan Carpien-Office of the General

Counsel, EPA

Notes

(1) Appointed on July 27, 1988.

(2) Appointed on September 9, 1988.

(3) Appointed on April 29,1988.

(4) Appointed on June 3, 1988.

The Committee acknowledges and is

grateful for the assistance and support

given the ITC by the staff of Dynamac

Corporation (technical support

contractor) and personnel of the EPA

Office of Toxic Substances.

Chapter 1-Introduction

1.1 Background. The TSCA

Interagency Testing Committee

(Committee) was established under

section 4(e) of the Toxic Substances

Control Act of 1976 (TSCA, Pub. L. 94-

469). The specific mandate of the

Committee is to recommend to the

Administrator of the U.S. Environmental

Protection Agency (EPA) chemical

substances and mixtures in commerce

that should be given priority

consideration for the promulgation of

testing rules to determine their potential

hazard to human health and/or the

environment. TSCA specifies that the

Committee's recommendations shall be

in the form of a Priority List, which is to

be published in the Federal Register.

The Committee is directed by section

4(e)(1)(A) of TSCA to designate those

chemicals on the Priority List to which

the EPA Administrator should respond

within 12 months by either initiating a

rulemaking proceeding under section

4(a) or publishing the Administrator's

reason for not initiating such a

proceeding. There is no statutory time

limit for EPA response regarding

chemicals that ITC has recommended

but not designated for response within

12 months.

At least every 6 months, the

Committee makes those revisions in the

section 4(e) Priority List that it

determines to be necessary and

transmits them to the EPA

Administrator.

The Committee is composed of

representatives from eight statutory

member agencies and seven liaison

agencies. The specific representatives

and their affiliations are named in the

front of this report. The Committee's

chemical review procedures and priority

recommendations are described in

previous reports (Refs. 1 through 7).

1.2 Committee's previous reports.

Twenty-two previous reports to the EPA

Administrator have been issued by the

Committee and published in the Federal

Register (Refs. 1 through 7). Ninety-six

entries (seventy-six chemicals and

twenty groups of chemicals) were

recommended for priority consideration

by the EPA Administrator and

designated for response within 12

months. In addition, 24 chemicals and

one group of chemicals were

recommended without being so

designated. Overall, in the 22 reports to

the EPA Administrator, the CQmmittee

has recommended testing for 100

chemicals and 21 groups of chemicals. A

complete list of recommended chemicals

may be obtained by contacting the ITC

Executive Secretary at the following

address/telephone number: Robert

Brink, U.S. Environmental Protection

Agency (TS-792), 401 M St., SW.,

Washington, DC 20460, (202) 382-3820.

1.3 Committee's activities during this

reporting period. Between April 22, 1988

and October 20, 1988, the Committee

continued to review chemicals from its

fifth and sixth scoring exercises, and

from nominations by Member Agencies,

Liaison Agencies and State Agencies.

The Committee contacted chemical

manufacturers and trade associations to

request information that would be of

value in its deliberations. Most of those

contacted provided unpublished

information on current production,

exposure, uses, and effects of chemicals

under study by the Committee.

During this reporting period, the

Committee reviewed available

information on 54 chemicals. Six were

selected for addition to the section 4(e)

Priority List, and twenty-one were

deferred indefinitely. The remaining

chemicals are still under study.

In its twentieth report to the EPA

Administrator (Ref. 5, ITC, 1987), the

Committee placed ethylbenzene (CAS

No. 100-41-4) on the Priority List in the

"Recommended with Intent-toDesignate" category. The Committee

recommeded that ethylbenzene be

tested for acute toxicity to freshwater

algae and invertebrates and to saltwater

algae, invertebrates and fish.

Subsequently, the Committee learned

that acute toxicity testing of

ethylbenzene with freshwater

invertebrates had recently been

completed at the University of

Wisconsin. As noted in the twenty-first

and twenty-second reports, the

Committee also was informed that a

consortium of ethylbenzene producers,

the Styrene and Ethylbenzene

Association, voluntarily sponsored

studies on the other acute toxicity tests

recommended by the Committee. The

Committee deferred a decision on

whether or not to designate

ethylbenzene pending a review of the

data developed during the above

studies. The Committee has reviewed

the data developed in those studies and

has concluded that all of the data gaps

identified in the twentieth report have

been satisfactorily resolved. Therefore,

the Committee has decided that

ethylbenzene should be removed from

the Priority List.

1.4 The TSCA section 4(e) Priority

List Section 4(e)(1)(B) of TSCA directs

the Committee to: "* * * make such

revisions in the [priority] list as it

46264
Federal Register / Vol. 53, No. 221 / Wednesday, November 16, 1988 / Notices

determines to be necessary and * * *

transmit them to the Administrator

together with the Committee's reasons

for the revisions." Under this authority,

the Committee is revising the Priority

List by adding six chemicals: tris(2-

chloroethyliphosphate (CAS No. 115-96-

8), tris(2-chloro-l-propyl)-phosphate

(CAS No. 6145-73-9), tris(l-choloro-2-

propyl~phosphate (CAS No. 13674-84-5),

tris(1,3-dichloro-2-propyl)phosphate

(CAS No. 13674-87-8), tetrakis(Zchloroethyl)ethylene diphosphate (CAS

No. 33125-86-9), and butyraldehyde

(CAS No. 123-72-8). In addition, the

Committee is designating, for repsonse

within 12 months, crotonaldehyde,

which was recommended with intent-todesignate in the twenty-second report.

Two chemicals are being removed from

the Priority List at this time. Methyl

ethyl ketoxime (CAS No. 96-29-7) was

the subject of a Notice of Proposed

Rulemaking (53 FR 35838; September 15,

1988) and ethylbenzene (CAS No. 100-

41-4) is being removed for the reasons

given in section 1.3.

With the six new recommendations

and two removals noted in this report,

twenty-one entries now appear on the

section 4(e) Priority List. The Priority

List is divided in the following Table 2

into three parts; namely, A. Chemicals

and Groups of Chemicals Designated for

Response Within 12 Months, B.

Chemicals and Groups of Chemicals

Recommended with Intent-to-Designate,

and C. Chemicals and Groups of

Chemicals Recommended Without Being

Designated for Response Within 12

Months. Table 2 follows:

TABLE 2-THE TSCA SECTION 4(E)

PRIORITY LIST, NOVEMBER 1988

Entry Date of I designation

A. Chemicals and Groups of

Chemicals Recommended and

Designated for Response Within

12 Months:

1. 1,6-Hexamethylene dilsocyanate.

2. Crotonaldehyde ........................

B. Chemicals and Groups of

Chemicals Recommended with

Intent-to-Designate:

1. Tds(2-chloroethyl phosphate..

2. Tris(2-ctdoro-propyl) phosphate.

3. Tris(1-choloro-2-propyl)

phosphate.

4. Trds(1.3-dichloro-2-propyl)

phosphate.

5. Tetrakis(2-chloroethyl) ethylene diphosphate.

C. Chemicals and Groups of

Chemicals Recommended Wthout Being Designated for Response Within 12 Months:

1. Disodecyt phenyt phosphite.

2. C.I. Disperse Blue 79 ............

May 1988

Nov. 1988

Nov. 1988

Nov, 1988

Nov. 1988

NOV. 1988

Nov. 1988

Nov. 1985

NoV. 1986

TABLE 2-THE TSCA SECTION 4(E) PRIORITY LIST, NOVEMBER 1988--Continued

Entry Date of

I designation

3. N[5-[bis[2-(acetyloxy)

ethyflemino]-2-4(2-bromo4,6-dinltrophanyl) azo]-4-

methoxy phenytl-ecetamide.

4. N-5-bis[2-(acetyloxy)

ethyljamino]-2-(2-chloro4,6.dinitropheny) azo]-4-

methoxy phenyl]-acetemide.

5. N-[5-[bis[2-(acetytoxy)

ethyl]aminol-2-[(2-choro4,6-dinitrophenyl) azo]-4-

ethoxy phenyl]-acetamide.

6. Imidazolium compounds,

4,5-dihydro-1-methyl-2-

nortallow alkyl-1-(2-taflow

amidoethyl), Me sulfates.

7. Ethanaminium,2-amno-N-(2-

aminoethyl)-N-(2-

hydroxyethyl)-N-methy-N,N'-

ditallow acyl derivs. Me sulfates (salts).

8. Poly(oxy-1,2-ethanediyl)a-

[2-[bis(2-aminoethy)-

methylammonio]-ethyl]-ohydroxy-, N,N'.dicoco acyl

derive., Me sulfates (salts).

9. PoIy(oxy-1,2-ethanedyl),a-

[2- Ibis (2-aminoethyl)-

methylammonio-ethyll-w-,

N,N'-bis(hydrogenated tallow

acyl) derivs., Me sulfates

(salts).

10. Poly(oxy-1,2-ethanediyl), a-

(2-[bis (2-aminoethyl)-methylam monio-ethyll-w-hydroxy-,

N,N'-ditallow acyl derivs.,

Me sulfates (salts).

11. Polyloxy(methyl-1,2-ethanediyl),a-[2-[bis(2-

aminoethyl)-

methyfammoniol-methyl

ethyl]-co-hydroxy-, N,N'-ditallow acyl deiv., Me sulfates

(salts).

12. Pofy(oxy-1,2.ethanediyl),a-

[3-[bis(2aminoethyl)-

methylammonio]-2-

hydroxypropyl]-whydroxy-,

N-coco acyl derivs., Me sulfates (salts).

13. Poly(oxy-1,2-4thanedly),a-

[2-[bis(2-aminoethy0-

methylammonio]-ethy )-

eohydroxy-, NN'-di-Cu.,. acyl

derive., Me sulfates (salts)D

May 1988.

14. Butyraldehyde .......................

May 1987

May 1987

May 1987

May 1988

May 1988

May 1988

May 1988

May 1988

May 198

May 1988

Nov. 1988.

REFERENCES

(1) Sixteenth Report of the TSCA

Interagency Testing Committee to the

Administrator, Environmental Protection

Agency. TSCA In teragency Testing

Committee, May 21, 1985, 50 FR 20930-20939.

Includes references to Reports I through 15

and an annotated'list of removals.

(2) SeventeenthReport of the TSCA

Interagency Testing Committee to the

Administrator, Environmental Protection

Agency. TSCA Interagency Testing

Committee. November 19, 1885, 50 FR 47603-

47612.

(3) Eighteenth Report of the TSCA

Interagency Testing Committee to the

Administrator, Environmental Protection

Agency. TSCA Interagency Testing

Committee, May 19, 1986, 51 FR 18368-18375.

(4) Nineteenth Report of the TSCA

Interagency Testing Committee to the

Administrator, Environmental Protection

Agency. TSCA Interagency Testing

Committee, November 14,1986, 51 FR 41417-

41432.

(5) Twentieth Report of the TSCA

Interagency Testing Committee to the

Administrator, Environmental Protection

Agency. TSCA Interagency Testing

Committee, May 20,1987, 52 FR 19020-1902,.

(6) Twenty-first Report of the TSCA

Interagency Testing Committee to the

Administrator, Environmental Protection

Agency. TSCA Interagency Testing

Committee, November 20,1987, 52 FR 44830-

44837.

(7) Twenty-second Report of the TSCA

Interagency Testing Committee to the

Administrator, Environmental Protection

Agency. TSCA Interagency Testing Committee, May 20, 1988,53 FR 18196-18210.

Chapter 2--Recommendations of the

Committee

2.1 Chemicals recommended for

priority consideration by the EPA

Administrator. As provided by section

4(e)(1)(B) of TSCA, the Committee is

adding the following chemical

substances to the section 4(e) Priority

List: tris(2-chloroethyl)phosphate (CAS

No. 115-90-8), tris(2-chloro-1-

propyl)phosphate (CAS No. 6145-73-9),

tris(1-chloro-2-propyl)phosphate (CAS

No. 136744-5), tris(1, 3-dichloro-2-

propyl)phosphate (CAS No. 13674-87-8),

tetrakis(2-chloroethyl)ethylene

diphosphate (CAS No. 33125-86-9), and

butyraldehyde (CAS No. 123-72-8). In

addition, the Committee is designating

for response within 12 months one

chemical that was recommended with

intent-to-designate in the twenty-second

report. The designated chemical is

crotonaldehyde (CAS No. 4170-30-3).

The recommendation of these chemicals

is made after considering the factors

identified in section, 4(e)(1)(A) and other

relevant information, as well as the

professional iudgment of Committee

members.

2.2 Chemicals designated for response

within 12 months-2.2.a

Crotonaldehyde. In the twenty-second

report to the Administrator of EPA (53

FR 181,96) crotonaldehyde was

recommended with intent-to-designate.

The rationale for that recommendation

appears in the twenty-second report.

Information reviewed by the Committee

in response to the twenty-second report

includes any public comments on the

Committee's recommendations;

production volume, use, exposure and

release information reported by

46265
Federal Register / Vol. 53, No. 221 / Wednesday, November 16, 1988 / Notices

manufacturers of crotonaldehyde under

the TSCA section 8(a) Preliminary

Assessment rule; health and safety

studies submitted under TSCA 8(d)

Health and Safety Data Report rule; and

any unpublished and published data

available to the Committee.

After reviewing the information, the

Committee concluded that data are still

lacking on certain chemical fate factors

and ecological effects. For these reasons

and for the reasons previously presented

(53 FR 18196) the Committee is now

designating crotonaldehyde for response

within 12 months and recommending

that it be tested for the following:

1. Chemical fate. Volatilization rate

from water, aerobic aquatic

biodegradation rate.

2. Health effects. None.

3. Ecological effects. Acute toxicity to

algae, fish and aquatic invertebrates.

2.3 Chemicals recommended with

intent-to-designate-2.3.a Tris(2-

chloroethyl)phosphate-Summary of

recommended studies, It is

recommended that tris(2-

chloroethyl)phosphate (TCEP) be tested

for the following:

1. Chemical Fate. Environmental

monitoring; vapor pressure;

biodegradation,

2. Health Effects. None.

3. Environmental Effects. Acute

toxicity to aquatic and terrestrial plants;

chronic toxicity to fish,

PHYSICAL AND CHEMICAL INFORMATION

CAS No. 115-96-8

.VMY1 ............................................I

Structural Formula:

O--CHCH2Cl

0 = P-0-CHCHCl

Fn O-CHCHCl

Emo" .... ca ................................... .................... ......... M olecular W eight ................................................................

M elting Point ('C) ...............................................................

Boiling Point ('C) ................................................................

Vapor Pressure (m m Hg) ...................................................

Solubility in W ater (m g/L); ................................................ Specific Gravity: .................................................................. Log Octanol/Water Partition Coefficient (log P) .............

Henry's Law Constant: .......................................................

Adsorption Coefficient (Koc): ............................................

Description of Chemical: ...........................

Ethanol, 2-chloro, phosphate (3:1) (gCt);

Tris (rchloroethyl) phosphate;

FYROL CEF;

FYROL PCF;

Colluflex CEF;

Disfiamol TCA;

Nax Flame Retardant 3CF.

TCEP.

Cst2CHaW4 . 285.5.

-55 (Ref. 25, Sandmeyer and Kirwin, 1981).

330 (Ret. 2, Aldrich, 1986).

No information was found.

7,943 (Ref. 31, Yoshioka et al., 1986).

1.425 @ 20/20- (Ref. 28, Sax and Lewis, 1987).

1.7 (Ref. 31, Yoshioka et al., 1986).

1.81 x 10- atm mS/mol (Ref. 21, Muir, 1984).

5.2 (Estimated; Ref. 4, CHEMEST, 1988).

Colorless liquid with slight odor (Ref. 17, Lefaux, 1968).

Rationale for Recommendations

1. Exposure Information

A. Production/use/release to the

environment. Tris (2-chloroethyl)

phosphate (TCEP) is produced in

substantial but CBI annual amounts in

the U.S. Actual production volumes are

considered to be confidential business

information. It is used as a flame

retardant additive for flexible and rigid

polyurethane and polyisocyanurate

foams, carpet-backing, flame-retardant

paints and lacquers, various resins,

coatings and adhesives (Ref 15, KirkOthmer, 1980). The major use appears to

be in foams such as the flexible foams

used in automobiles and furniture and

iigid foams for building insulation

mterials. It is unlikely that there is any

natural production of TCEP. Most of the

production eventually will be released

to the environment as furniture, and

landfills. Some may be released during

thermal decomposition (accidental fires

and waste incineration). Muir (Ref. 21,

1984) cited a report by Cho and Klaus

(1980) stating that 41 percent of TCEP

remains intact after thermal oxidation in

air at 370°C. However, Paciorek et al.

(Ref. 23, 1978) reported that 85 percent of

the TCEP chlorine was accounted for in

volatile products of degradation at

370C, which indicates that no more

than 15 percent of the TCEP was left

undegraded.

B. Evidence for environmental

exposure. TCEP, in common with many

similar tris(haloalkyl)phosphates, has

been found in numerous environmental

samples throughout the world, at very

low concentrations. TCEP was found in

river waters in Japan at 17 to 350 ng/L at

14 of 16 sites at Kitakyushu (Ref. 12,

Ishikawa et al., 1985b) and in Canadian

rivers at 13 sites, with a mean

concentration of 8.7 ng/L (Ref. 29,

Williams and LeBel, 1981). TCEP was

detected in the Netherlands in the river

Waal (Ref. 19, Meijers and Van der Leer,

1976) and the Rhine (Ref. 24, Piet et al.,

1987). TCEP was present in ground

water from two wells at Fort Devens,

MA at concentrations of 0.28 and 0.81

ug/L (Ref. 3, Bedient et al., 1983; Ref. 10,

Hutchins et al.. 1984). Water from the

Great Lakes contained TCEP at a mean

concentration of 1.7 ng/L at ten

Canadian sites (Ref. 30, Williams and

LeBel. 1981] and at concentrations of 3

to 9.6 ng/L at 4 of 5 sites in a later report

(Ref. 16, LeBel et al., 1987). Samples from

10 coastal sites in Japan contained 14 to

60 ng/L in the seawater (Ref. 12,

Ishikawa et al., 1985b). Sewage

treatment facilities in Japan contained

from 540 to 1,200 ng/L TCEP in the

influent to the plants and 500 to 1,200

46266
Federal Register / Vol. 53, No. 221 / Wednesday, November 16, 1988 / Notices

ng/L in the effluents. Similarly, at night

soil treatment facilities, the influent

contained 190 to 1,500 ng/L TCEP and

the effluents were found to have 190 to

1,500 ng/L (Ref. 13, Ishikawa et al.,

1985c). Five river and ocean sediment

samples from Japan contained 13 to 28

ng TCEP/g of sediment. None was

detected in a sixth sample (Ref. 12,

Ishikawa et al., 1985b). TCEP was

detected but not quantified in ambient

air at Kitakyushu, Japan (Ref. 9,

Haraguchi et al., 1985).

In a survey of infant and toddler

dietary intake from October 1978

through September 1979, Gartrell et al.

(Ref. 7, 1985a) reported finding TCEP in

composite U.S. drinking water at anaverage concentration of 0.3 ug/L.

Drinking water in Japan, examined over

a 1-year period, contained 2 to 60.5 ng/L

TCEP, with a mean concentration of 17.4

ng/L (Ref. 1, Adachi et al., 1984). Fifteen

pooled U.S. drinking water samples

contained an average of 2.6 ng/L TCEP

(Ref. 18, Lucas, 1984) and Millington et

al. (Ref. 20, 1983) reported finding TCEP

on activated carbon filter beds used at

40 U.S. drinking water treatment plants.

In a study of drinking water samples in

England, Fielding et al. (Ref. 6, 1981)

found TCEP in one of fourteen samples.

LaBel et al. (Ref. 16, 1987) found TCEP at

0.3 to 9.2 ng/L in duplicate drinking

water samples from six sites in eastern

Ontario. Drinking water from 22 other

Canadian cities contained TCEP at 0.3 to

52 ng/L while water from 7 other cities

contained no detectable TCEP (Ref. 29,

Williams and LeBel, 1981). In a survey of

drinking water from the Great Lakes at

twelve Canadian cities, Williams et al.

(Ref. 30, 1982) found concentrations of

TCEP at 0.3 to 13.8 ng/L in water at 11 of

the cities. In a survey of infant and

toddler diets from October 1979 through

September 1980, Gartrell et al. (Ref. 8,

1985b) reported TCEP in composite fruit

and fruit juice samples at an average

concentration of 0.2 ug/L It was not

detected in other foods tested. Fish from

the Okayama Prefecture in Japan

contained from less than 0.005 ug/g up

to 0.019 ug/g TCEP (Ref. 14, Kenmochi et

al., 1981).

TCEP and other widely used

tris(chloroalkyl)phosphate flame

retardants appear to be widely

distributed in the environment,

especially in water, at low

concentrations. It is not known whether

the environmental concentrations are

increasing with time or whether these

anthropogenic phosphates have attained

some steady-state, low-level

concentrations.

II. Chemical Fate Information

A. Transport. The water solubility of

TCEP is reported to be from 7,000 (Ref.

17, LeFaux, 1968) to 8,300 mg/L (Ref. 11,

Ichikawa et al., 1985a). A measured

value of 7,943 mg/L was reported by

Yoshioka at al. (Ref. 31,1986). A

measured value for the log octanol/

water partition coefficient was reported

as 1.7 (Ref. 31, Yoshioka et al., 1986).

These data indicate that TCEP,

following release to the environment,

will partition largely to water with little

accumulation in sediments or biota.

Vapor pressure data at environmentally

relevant temperatures were not found,

but the Henry's Law constant reported

by Muir (Ref. 21, 1984) indicates no

significant volatilization from water.

The monitoring evidence (see preceding

paragraph 1.B.) demonstrates

widespread occurrence of TCEP in

water with some partitioning to air,

sediments and biolipids.

B. Persistence. The

trialkylphosphates, in general, are

resistant to hydrolysis and free-radical

oxidations although hydrolysis at the pH

of sea water (approximtely 8.5) may be

significant. TCEP is expected to

demonstrate similar resistance to

hydrolysis and oxidation, although no

data were found. Biodegradation is

probably the major degradation

mechanism in nature but the available

data, which indicate that biodegradation

is slow, are mostly circumstantial. There

are reports of very little biodegradation

of TCEP as it passes through drinking

water sand filtration units (Ref. 24, Piet

et al., 1981) and through sewage

treatment and night soil treatment

facilities (Ref. 11, Iehikawa et al., 1985a).

TCEP was reported to be hardly

degraded after 50 hours in activated

sludge (Ref. 11, Ishikawa, et al., 1985a).

C. Rationale for chemical fate

recommendations. There is widespread

contamination of the environment by

TCEP (and other

tris(chloroalkyl)phosphates) at very low

concentrations. There is some evidence

that TCEP may be resistant to

biodegradation. Based on its water

solubility and octanol/water partition

coefficients, TCEP released to the

environment is expected to partition

largely to water. No data were found on

its vapor pressure at ambient

temperatures. Since TCEP has been and

will continue to be released to both

water and soil (landfill) environments,

there is a need to obtain measured

vapor pressure data and to evaluate its

biodegradability in natural waters. It

also is recommended that appropriate

follow-on monitoring studies be

conducted at sites sampled in the 1970's

and early 1980's in an attempt to

determine whether environmental

concentrations are increasing with time.

III. Biological Effects of Concern to

Human Health

A two-year gavage study with rats

and mice has recently been completed

under the National Toxicology Program

(Ref. 22, NTP, 1988) and is currently in

the histopathology stages. Given this

information, the Committee has deferred

its review of TCEP for health effects

pending receipt and review of data from

the NTP study.

IV. Ecological Effects of Concern

A. Acute and subchronic (short-term)

effects. The 96-hour LC50 of TCEP was

reported to be 210 mg/L with killifish

(Orizias latipes) and 90 mgtL with

goldfish (Carassius auratus) (Ref. 26,

Sasaki et al., 1981). These authors also

reported spine deformations .(caused by

convulsive muscle contractions) in

killifish with exposure to 200 mg/L of

TCEP for 72 hours and protrusion of

killifish eyes after 24 to 72 hours

exposure to 200 mg/L. Yoshioka et al.

(Ref. 31, 1986) reported LC50 values of

251 mg/L with red killifish (Orizias

latipes), 1,000 mg/L with a daphnia

species (Moina macrocopa) and 158 mg/

L with a flatworm (Dugesia japonica).

Another literature report (Ref. 5,

Eldefrawi et al., 1977) stated that 5 mg/L

TCEP had no observable effects on

goldfish after 7 days exposure.

B. Chronic (long-term) effects. No

information on chronic effects was

found. Sasaki et al. (Ref. 26, 1981), as

noted in the preceding paragraph,

reported spine deformations and eye

bulging in killifish exposed to 200 mg/L

for 72 hours. Eldefrawi at al. (Ref. 5,

1977) reported that TCEP is a weak

inhibitor of acetyl-cholinesterase and

this may produce some chronic effects.

C. Other ecological effects (biological,

behavioral, or ecosystem processes) No

information was found.

D. Bioconcentration and food-chain

transport. The bioconcentration of TCEP

was examined by Sasaki et al. (Ref. 26,

1981 and Ref. 27,1982) in both static and

continuous-flow studies. Static tests

with killifish and goldfish showed

bioconcentration factors (BCFs) of 2 and

1, respectively. A BCF of I was observed

for killifigh in continuous-flow studies

over a 10-day period. When the fish

were placed in clean water there was

rapid depuration with half gone in 0.7

hours after-cessation of exposure.

E. Rationale for ecological effects

recommendation. The widespread

occurrence of TCEP in environmental

samples raises concerns for its

46267
Federal Register / Vol. 53, No, 221 / Wednesday, November 16, 1988 / Notices

ecological effects. On the other hand,

the available data indicate that acute

toxicity levels for fish and aquatic

invertebrates are 1,000 times or more

greater than observed environmental

concentrations. However, there were no

data on plants and it is recommended

that TCEP be tested for acute toxicity to

aquatic and terrestrial plants. There

appear to be chronic exposures to low

concentrations of TCEP in aquatic

environments and reports of spine

deformations raise concerns for chronic

effects. Therefore, it is recommended

that TCEP also be tested for chronic

toxicity to fish.

References

(1) Adachi, K., Mitsuhaski, T., and Ohkuni,

N. "Pesticides and trialkyl phosphates in tap

water." Hyogo-ken Eisei Kenkyusho Kenkyu

Hokoku. 19:1-6 (1984).

(2) Aldrich. Aldrich Chemical Company. Catalog Handbook of Fine Chemicals, p. 1341

(3) Bedient, P.B., Springer, N.K., Baca, E.,

Bouvette, T.C., Hutchins, SR., and Tomson,

M.B. "Ground-water transport from

wastewater infiltration." Journal of

Environmental Engineering. 109(2):485-501 (1983).

(4) CHEMEST. "A program for chemical

property estimation [data base)."

Washington, DC: U.S. Environmental

Protection Agency. Office of Pesticides and

Toxic Substances (1988). (5) Eldefrawi, A.T., Mansour, N.A.,

Brattsten, LB., Ahrens, V.D., and Lisk, D.J.

"Further toxicologic studies with commercial

and candidate flame retardant chemicals.

Part U." Bulletin of Environmental

Contamination and Toxicology. 17:720-726

(1977). (6) Fielding, M., Gibson, T.M., James, H.A.,

McLoughlin, K., and Steel, C.P. "Organic micropollutants in drinking water." Technical

Report TR159, Water Research Centre,

Medmenham, England. 47 pp. (1981). (7) Gartrell, M.J., Craun, I.C., Podrebarac,

D.S., and Gunderson, E.L. "Pesticides,

selected elements and other chemicals in

infant and toddler total diet samples, October

1978-September 1979." Journal of Association

of Official Analytical Chemists. 68(5):842-861

(1985a).

(8) Gartrell, M.J., Craun, I.C., Podrebarac,

D.S., and Gunderson, E.L., "Pesticides,

selected elements, and other chemicals in

infant and toddler total diet samples, October

1979-September 1980," Journal of Association

of Official Analytical Chemists. 68(6):1163-

1183 (1985b). (9) Haraguchi, K., Yamashita, T., and

Shigemori, N. "Sampling and analysis of

phosphoric acid triesters in ambient air."

Taiki Osen Cakkaishi 20,407-415 (1985). (10) Hutchins, S.R., Tomson, M.B., Wilson,

J.T., and Ward, C.H. "Fate of trace organics

during rapid infiltration of primary

wastewater at Fort Devens, Massachusetts."

Water Research. 18:1025-1036 (1984).

(11) Ishikawa, S., Shigezumi, K., Yasuda, K.,

and Shigemori, N "Behavior of organic

phosphate esters in several waste water

treatment processes." Suishitsu Odaka

Kenkyu, 8:799-807 (1985a).

(12) Ishikawa, S., Taketomi, M,, and

Shinohara, R. "Determination of trialkyl and

triaryl phosphates in environmental

samples." Water Research. 19(1):119-125

(1985b).

(13) Ishikawa. S., Shigezumi, K., Yasuda, K.,

and Shigemori, N. "Determination of organic

phosphate esters in factory effluent and

domestic effluent." Suishitsu Odako Kenkyu

8:529-535 (1985c).

(14) Kenmochi, U., Matsunaga, K., and

Ishida, R., "The effects of environmental

pollutants on biological systems. 6. Organic

phosphates in environments." Okoyamaken

Kankyo Hoken Senta Nenpo. 5:167-175 (1981).

(15) Kirk-Othmer. Kirk-Othmer

Encyclopedia of Chemical Technology. New

York, NY: John Wiley & Sons, Inc. Vol. 10, p.

401-402 (1980).

(16) LaBel, G.L., Williams, D.T., and Benoit,

F.M. "Use of large-volume resin cartridges for

the determination of organic contaminants in

drinking water derived from the Great

Lakes." Advances in Chemistry Series.

214:309-325 (1987).

(17) LeFaux, R. Practical Toxicology of

Plastics. English Edition. London, UK: Iliffe

Books Ltd. (1968).

(18) Lucas, S.V. "GC/MS analysis of

organics in drinking water concentrates and

advanced waste treatment concentrates:

Volume I. Analysis results for 17 drinking

water, 16 advanced waste treatment and 3

process blank concentrates." EPA-600/1-84-

020a. Washington, DC: U.S. Environmental

Protection Agency, Office of Research and

Development. 321 pp. (Nov. 1984).

(19) Meliers, A.P., and Van der Leer, R.,

Chr. "The occurrence of organic

micropollutants in the River Rhine and the

River Maas in 1974." WaterReseorch. 10:597-

604 (1976).

(20) Millington. D.C., Bertino, D.J., Kamei,

T., and Christman, R.F. "Analysis of organic

compounds adsorbed on granular activated

carbon filters used in treatment plants."

Water Chlorination, Environmental Impact

and Health Effects. Vol. 4, Book 1, R. L Jolley

at al. (ads.), Ann Arbor Science, Ann Arbor,

MI, pp. 445-454 (1987).

(21) Muir, D.C.G. "Phosphate Esters." The

Handbook of Environmental Chemistry. Vol.

3/Part C, 0. Hutzinger, ad., Springer-Verlag,

New York,, pp. 41-66 (1984).

(22) NTP, National Toxicology Program.

Data from NTP CHEMTRACK System

(database), July 21,1988.

(23) Paciorek, K.J.L. Kratzer, R.H.,

Kaufman, I., Nakahara, J.H., Christos, T., and

Hartstein. A.M. "Thermal oxidative

degradation studies of phosphate esters."

American Industrial Hygiene Association

Journal. 39(8):1633-639 (1978).

(24) Piet, G.J.. Morra, C.H.F., and DeKruijf,

M.A.M. "The behaviour of organic

micropollutants during passage through the

soil." Studies in Environmental Science.

17:557-564 (1981).

(25) Sandmeyer, E.E., and Kirwin, C.J,

"Esters." G.D. Clayton and F.E. Clayton, Eds.

"Patty's Industrial Hygiene and Toxicology"

Third Revised Edition. New York, NY John

Wiley and Sons., pp. 2259-2412 (1981).

(26) Sasaki, K., Takeda, M., and Uchiyama,

M. "Toxicity absorption and elimination of

phosphoric acid triesters by killifish and

goldfish." Bulletin of Environmental

Contamination and Toxicology. 27:775-782

(1981).

(27) Sasaki, K., Suzuki, T., Takeda, M., and

Uchiyama, M. "Bioconcentration and

excretion of phosphoric acid triesters by

killifish (Oryzeas latipes)." Bulletin of

Environmental Contamination and

Toxicology. 28:752-759 (1982).

(28) Sax, N.L. and Lewis Sr., R.J. Hawley's

Condensed Chemical Dictionary. 11th ad.,

New York, NY: Van Nostrand Reinhold Co. p.

1194 (1987).

(29) Williams, D.T., and LaBel, G.L. "A

national survey of tri(haloalkyl)-, trialkyl-,

and triarylphosphates in Canadian drinking

water." Bulletin of Environmental

Contamination and Toxicology. 27:450-457

(1981).

(30) Williams, D.T., Nestmann, E.R., LeBel,

GL., Benoit, F.M., Otson. R., and Lee, E.G.H.

"Determination of mutagenic potential and

organic contaminants of Great Lakes

(Canada, USA) drinking water."

Chemosphere. 11(3):263-276 (1982).

(31) Yoshioka, Y., Ose, Y., and Sato, T.

"Correlation of five test methods to assess

chemical toxicity and relation to physical

properties." Ecotoxicity and Environmental

Safety. 12:15-21 (1986).

2.3.b Tris(chloropropylphosphates--

Summary of recommended studies. It is

recommended that tris(Z-chloro-lpropyl)phosphate (CAS No. 6145-73-9)

and tris(1-chloro-2-propyl)phosphate

(CAS No. 13674-84-5) be tested for the

following:

1. Chemical fate. Environmental

monitoring; water solubility; vapor

pressure; octanol/water partition

coefficient; biodegradation.

2. Health effects. Acute and

subchronic effects; including

cholinesterase inhibition, 90-day

subchronic effects and reproductive

effects.

3. Ecological effects. Acute toxicity to

fish, aquatic invertebrates and algae;

chronic toxicity to fish. It is further

recommended that tris(1,3-dichloro-2-

propyl)phosphate (CAS No. 13674-87-8)

be tested for the following:

1. Chemicalfate. Environmental

monitoring; water solubility; vapor

pressure; octanolfwater partitioning

coefficient; biodegradation.

2. Health effects. None.

3. Ecological effects. Acute toxicity to

fish, aquatic invertebrates and algae;

chronic toxicity to fish.

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PHYSICAL AND CHEMICAL INFORMATION

CAS No. 6145-73-9 1 i

9 Cl Name ...........................................................................

Synonyms ......................................

Acronym ..............................................................................

Structural Formula:

0

II

':HCHCICH-- ---- CHCHCICH,

THCI

CH

Empirical Formula ...............................................................

Molecular Weight ................................................................

Melting Point ('C) ........................

Boiling Point ('C) ................................................................

Vapor Pressure (mmHg) ...........................

Solubility in Water (mg/L) ..................................................

Specific Gravity ...................................................................

Log Octanol/Water Partition Coefficient .........................

1-Propanol, 2-chloro-, phosphate (3:1).

2-Chloro-l-propanol phosphate;

Tris(beta-chloropropyl)-phosphate;

Tris(2-chloropropyl)phosphate;

FYROL PCF.

TCPP.

CpHiC4O4P.

327.55.

No information was found.

No information was found.

No information was found.

No information was found.

No information was found.

No information was found.

Physical and Chemical Information

CAS No. 13674-84-5

9 CI Name ........................................................................... 2-Propanol, 1-chloro-, phosphate (3:1).

Synonyms .......... I.-Chloro-2-propanol phosphate;

Tris(2-chloroisopropyl)-phosphate;

Phosphoric acid, tris(2-chloro-l-methylethyt) ester;,

Tris(1-chloromethylethyl)-phosphate.

Acronym .......................................................................... TCIP.

Structural Formula:

~H3

CH CH

CHCI---CH,

H

Empirical Formula ................... ................... ..... C.H.C60.P,

Molecular W eight ................................................................ 327.55,

Melting Point ('C) ................................................................ No information was found.

Boiling Point ('C) .......................... No information was found,

Vapor Pressure (mmHg) ................................................... No information was found.

Solubility in Water (mg/L) .................... No information was found.

Specific Gravity........................................................ No information was found.

Log Octanol/Water Partition Coefficient ........... No information was found,

Physical and Chemical Information

CAS No. 13674-87-8

9 C1 Name ..................................................... 2-Propanol, 1,3-dichloro-,phosphate (3:1)

46269

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Federal Register / Vol. 53, No. 221 / Wednesday, November 16, 1988 / Notices

PHYSICAL AND CHEMICAL INFORMATioN-Continued

Synonyms ............................................................................

Acronyms .............................................................................

Structural Formula:

CH2CI 0 CHSCI

CH2CI CHXCI

CH.CI- 1 -CHXCI

H

Empirical Formula ...............................................................

Molecular Weight ................................................................

Melting Point ('C) ..................................

Boiling Point ('C) .................................................................

Vapor Pressure (mmHg) ....................................................

Solubility in Water (mg/L) ....................................

Specific Gravity ...........................................................

Log Octanol/Water Partition Coefficient (log P) ..............

___________________________________________________________________________ I

Rationale for Recommendations

I. Exposure Information

A. Production/use/release to

environment. TCPP, TCIP and TDCP are

each produced in substantial annual

amounts in the U.S. but actual

production volumes are classified as

confidential business information. TCPP

and TDCP are used as additive flame

retardants in various plastic materials.

TDCP is known to be used primarily in

flexible polyurethane foams. No

information was found on the use of

TCIP but it appears likely that it too is

used as an additive flame retardant.

Most of the production eventually will

be released to the environment as the

plastic materials containing them are

scrapped or disposed of in dumps and

landfills. Some may be released during

thermal decomposition (accidental fires

and waste incineration). A report by

Cho and Klaus (1980) stating that 32

percent of TDCP remains intact after

thermal oxidation in air at 370* C was

cited by Muir (Ref. 11, 1984). It was

reported by Paciorek et al. (Ref. 12, 1978)

that TDCP underwent 68 percent

thermal oxidation at 370* C. It is unlikely

that there is any natural production of

these phosphates.

t,3-Dichloro-2-propanol phosphate;

Tris(t .3-dichloro-2-propyl)-phosphate;

Trls(1 ,3-dichloroisopropyl)-phosphate;

i ns~ll -unlOromrun"

FYROL FR2; PF38

TDCP: TDCPP.

C(lHCI6O4P.

430.88.

26.7 (Ref. 18, Stauffer, 1979).

No information was found.

No information at environmentally relevant temperatures and pressures was found.

7 at 24'C (Ref. 2, Hollifield 1979);

100 at 25'C (Ref. 11, Muir, 1984);

1000 at 30'C (Ref. 18, Stauffer, 1979).

1.515 at 20/20- (Ref. 18, Stauffer, 1979).

3.8 (Ref. 13, Sasaki t al., 1981).

B. Evidence for environmental

exposure. No information was found on

TCPP or TCIP and there was no

indication that they have been looked

for in the environment. TDCP, in

common with many similar

tris(haloalkyl)phosphates, has been

found in many environmental samples

throughout the world, at very low

concentrations. TDCP was found in

Great Lakes water at 4 of 5 Canadian

sites (Ref. 9, LeBel et al., 1987). TDCP

was found by LeBel et al. (Ref. 7, 1981)

at 0.2 to 1.8 ng/L in drinking water at six

eastern Ontario sites. Drinking water

from 15 other Canadian cities contained

TDCP at 0.3 to 23 ng/L while water from

14 other cities contained no detectable

TDCP (Ref. 21, Williams and LeBel,

1981). In a survey of drinking water from

the Great Lakes at twelve Canadian

Cities, Williams et al. (Ref. 22, 1982)

found concentrations of TDCP at 0.1 to

15.7 ng(L. A study of activated carbon

filter beds used at 40 U.S. drinking water

treatment plants found

tris(chloropropyl)phosphate (not further

identified) on the carbon (Ref. 11,

Millington et al., 1983).

Fish and shellfish from the Okayama

,prefecture in Japan were reported to

contain tris(2, 3-

dichloropropyl)phosphate (Ref. 6,

Kenmochi et al., 1981).

In an examination of Swedish

products thought to contain additive

flame retardants (Ref. 16, Sellestroem

and Jansson, 1987), 11 of 104 samples

were found to contain TDCP. It'was

most common in polyurethane products

such as sound absorbing materials and

liners for cars and buses. These same

authors also examined the contents of

vacuum cleaner bags from one new and

one older (15-year old) house and found

TDCP in the dust from the older house.

In analyses of human adipose tissues,

LeBel and Williams (Ref. 8,1983) found

TDCP in 5 of 16 samples at 0.5 to 110 ng/

g. TDCP also was found at 5 to 50 ppb in

34 of 123 human seminal plasma

samples (Ref. 3, Hudec et al. 1981].

Japanese studies have reported

finding tris(chloropropyl)-phosphate

(CAS No. 26248-87-3) and

tris(dichloropropyl)phosphate (CAS No.

26604-51-3) (Ref. 1, Haraguchi et al.,

1985) and tris(3-chloropropyl)phosphate

(CAS No. 1067-98-7) and tris(2, 3-

dichloropropyl~phosphate (CAS No. 78-

43-3) (Ref. 4, Ishikawa et al., 1985a) in

air and treatment plant influents and

effluents in Japan. The first three CAS

numbers are not listed in the TSCA

Inventory and the fourth CAS number is

46270

r-- lorOwlipnowpnate;
Federal Register / Vol. 53, No. 221 / Wednesday, November 16, 1988 / Notices

a compound that is produced in low

amounts in the U.S. It may be that

Japanese industry uses

tris(chloropropyl)phosphate flame

retardants not commonly used in the

U.S. and that those compounds may be

introduced into the U.S. environment

from imported products.

TDCP and other widely used

tris(chloroalkyl)phosphate flame

retardants appear to be widely

distributed in the environment. When

they are looked for, they often are

found. No information was found on

monitoring studies designed to look for

TCPP or TCIP and monitoring should be

conducted if continued high production

and use are confirmed. Additional

monitoring studies to evaluate the

concentrations of TDCP in the

environment should be conducted to

determine whether its concentration in

the environment is increasing with time.

I. Chemical Fate Information

A. Transport. The water solubility of

TDCP is reported to be from 7 to 1,000

mg/L (Ref. 2, Hollifield, 1981, Ref. 11,

Muir, 1984, Ref. 18, Stauffer, 1979). The

log octanol/water partition coefficient is

reported to be 3.8 (Ref. 14, Sasaki et al.,

1981). No information was found for

TCPP and TCIP. The monitoring

evidence (see I.B., above) for TDCP

demonstrates widespread occurrence of

TDCP in water with some partitioning to

sediments and biolipids. TCPP and TCIP

are expected to behave similarly.

B. Persistence. No information was

found for TCPP, TCIP or TDCP.

However, Ishikawa et al. (Ref. 5,1985b)

reported that influent and effluent data

for activated sludge treatment showed

no biodegradation of

tris(chloropropyt~phosphate (CAS No.

1067-98-7) and tris(2,3-

dichloropropyl)phosphate (CAS No. 78-

43-3).

C. Rationale for chemical fate

recommendations. There is widespread

contamination of the environment by

TDCP. There may be persistent

background levels of TCPP and TCIP in

the environment but this is unknown.

There is a need to conduct appropriate

monitoring studies to determine if TCDD

and TCIP, like similar

tris(chloroalkyl)phosphate flame

retardants, are present in the

environment at low concentrations and

whether the environmental

concentrations of TDCP are increasing.

There also is a need to obtain reliable,

measured water solubility, vapor

pressure and octanol/water partition

coefficient data on these flame

retardants to better estimate their

transport in the environment and to

evaluate their biodegradability in

natural waters.

II. Biological Effects of Concern to

Human Health

The Committee determined that

tris(1,3-dichloro-2-propyl)phosphate

(CAS No. 13674--87-8 has-been studied

extensively for health effects and

concluded that additional studies are

not required. Therefore, health effects

testing is not being recommended at this

time.

A. Metabolism and toxicokinetics. No

information was found for TCPP or

TCIP.

B. Acute (short-term) effects. No

information was found for TCPP. An

LD5O of 56 mg/kg, administered

intravenously in mice, was found for

TCIP (U.S. Army data, cited in Ref. 13,

RTECS, 1988). The reliability of this

information cannot be assessed since

experimental details are not available.

Stauffer (cited in Ref. 20, USEPA,

1981) reported studies on the neurotoxic

potential of TDCP, a structurally similar

phosphate, on adult hens. At 10 g/kg, the

maximum tolerated dose, there was 7

percent inhibition of brain neurotoxic

esterase. In positive controls, treated

with tri-o-cresyl phospate at 0.5 g/kg,

there was an 85 percent inhibition.

No subchronic effects data were

found for TCIP. The neurotoxic potential

of TCPP in adult white Leghorn hens

was evaluated by Sprague et al. (Ref. 17,

1981). A group of 18 hens received an

initial oral dose of 13.23 g TCPP/kg,

followed by the same treatment 3 weeks

later. The animals were sacrificed 3

weeks after the second dose. Loss of

body weight, transient reductions in

food consumption and one death were

reported for the treated animals. Egg

production ceased shortly after the first

dose and there was severe feather loss.

No behavioral or histological evidence

of delayed neurotoxicity was observed.

C. Genotoxicity. No information was

found for TCPP or TCIP.

D. Oncogenicity. No information was

found for TCPP or TCIP. A structurally

similar compound, TDCP, was tested for

oncogenicity in rats of both sexes and

-produced a significantly increased

incidence of hepatocellular carcinoma

and interstitial cell tumors of the testes

(Ref. 19, Stauffer, 1981).

E. Chronic (long-term) effects. No

information was found for TCPP or

TCIP.

F. Reproductive and developmental

effects. No information was found for

TCPP or TCIP.

G. Observations in humans. No

information was found for TCPP or

TCIP.

H. Rationale for health effects

recommendations. Three

tris(chloropropyl)phosphates (TCPP,

TCIP and TDCP) are produced in

substantial amounts in the U.S. and used

as additive flame retardants. TDCP is

widely distributed in the environment at

low concentrations. No exposure

information (occupational, consumer or

environmental) is available for TCPP or

TCIP. It is assumed that use of the latter

two compounds as flame retardants will

eventually lead to the release of TCPP

and TCIP to the environment. TDCP

appears to be well studied for potential

health effects but there is very little

health effects information on TCIP and

TCPP. The health effects information is

limited to a LD50 for TCIP in mice by

intravenous exposure and a subchronic

evaluation of the neurotoxic potential of

TCPP in hens. An evaluation of

neurotoxicity should be conducted for a

period of 90 days.

In view of the lack of health effects

information on TCIP and TCPP and

given the acute effects, oncogenicity and

neurotoxicity of TDCP, it is

recommended that TCIP and TCPP be

tested for acute effects, including

cholinesterase inhibition, 90-day

subchronic effects and reproductive

effects. Based on the results of the

recommended studies, the need for longterm studies should be considered.

IV. Ecological Effects of Concern

A. Acute and subchronic (short-term)

effects. No information was found for

TCPP or TCIP.

The 96-hr LC5O for TDCP was

reported to be 3.6 mg/L with killifish

and 5.1 mg/L with goldfish (Ref. 14,

Saaski et al., 1981). These authors also

reported spine deformations (caused by

convulsive muscle contractions) in

killifish after 24 hours exposure at 3.5

mg/L TDCP.

B. Chronic (long-term) effects. No

information on chronic effects was

found. However, as noted in the

preceding paragraph, Sasaki et al. (Ref.

14, 1981) reported spine deformations in

killifish exposed to 3.5 mg/L TDCP for

24 hours,

C. Other ecological effects. No

information was found.

D. Bioconcentration and food-chain

transport. The bioconcentration of

TDCP was examined by Sasaki et al.

(Ref. 14, 1981 and Ref. 15, 1982) in both

static and continuous flow studies.

Static tests with killifish and goldfish

showed bioconcentration factors of 47 to

107 with killifish and 3 to 5 with

goldfish. In continuous-flow studies, the

bioconcentration factor for TDCP was 31

to 59 for up to 32 days exposure. There

46271
Federal Register / Vol. 53, No. 221 / Wednesday, November 16, 1988 / Notices

was a rapid depuration following

cessation of exposure to TDCP in the

continuous-flow studies, with half gone

in 1.7 hours.

E. Rationale for ecological effects

recommendations. The widespread

occurrence of TDCP in environmental

samples and the likely contamination of

the environment by TCPP and TCIP

raise concerns for their ecological

effects. Each should be tested for acute

toxicity to fish, aquatic invertebrates

and algae to better evaluate the hazard

associated with chronic exposures to

low environmental concentrations. The

observation of spine deformations in

fish exposed to TDCP and the

widespread occurrence of TDCP at low

concentrations also raises concerns for

chronic effects. It is recommended that

each of these tris(chloropropyl)-

phosphates be tested for chronic toxicity

to fish.

References

(1) Haraguchi, K., Yamashita, T., and

Shigemori, N. "Sampling and analysis of

phosphoric acid triesters in ambient air."

Taiki Osen Gakkaishi. 20:407-415 (1985).

(2) Hollifield, H.C. "Rapid nephelometric

estimate of water solubility of highly

insoluble organic chemicals of environmental

interests," Bulletin of Environmental

Contamination and Toxicology. 23:579-58

(1979).

(3) Hudec, T., Thean, J., Kuehl, D., and

Dougherty, R.C.

"Tris(dichloropropyl)phosphate, a mutagenic flame retardant: frequent occurrence in

human seminal plasma," Science. 211:951-952

(1981). (4) Ishikawa, S., Shigezumi, K., Yasuda, K..

and Shigemort, N. "Determination of organic phosphate esters in factory effluent and

domestic effluent." Suishitsu Odako Kenkyu. 8:529-535 (1985a). (5) Ishikawa, S., Shigezumi, K.. Yasuda, K., and Shigemori, N. "Behavior of organic phosphate esters in several waste water

treatment processes." Suishitsu Odaka

Kenkyu. 8:799-807 (1985b),

(6) Kenmochi, U., Matsunaga, K. and

Ishida, R. "The effects of environmental

pollutants on biological systems. 6. organic

phosphates in environments." Okoyomo-ken

Konkyo Hoken Senta Nenpo. 5:167-175 (1981).

(7) LeBel, G.L., Williams, D.T., and Benoit,

F.M. "Gas chromatographic determination of

trialkyl/aryl phosphates in drinking waterfollowing isolation using macroreticular

resin." Journal of Association of Official Analytical Chemists. 64:991-998 (1981).

(8) LaBel, G.L., and Williams, D.T.

"Determination of organic phosphate triesters

in human adipose tissue." Journal of

Association of Official Analytical Chemists.

66:691-699 (1983).

(9) LeBel, G.L., Williams, D.T., and Benoit,

F.M. "Use of large-volume resin cartridges for

the determination of organic contaminants in

drinking water derived from the Great

Lakes." Advances in Chemistry Series.

214:309-325 (1987).

(10) Millington, D.C., Bertino, D.J., Kamei,

T., and Christman, R.F. "Analysis of organic

compounds adsorbed on granular activated

carbon filters used in treatment plants."

Water Chlorination, Environmental Impact

and Health Effects. Vol. 4, Book 1. Jolley, R.L

at al. (eds.), Ann Arbor Science, Ann Arbor,

MI, pp. 445-454 (1987).

(11) Muir, D.C.G. "Phosphate esters." The

Handbook of Environmental Chemistry. Vol.

3/Part C, 0. Hutzinger (ed.), Springer-Verlag,

New York, pp. 41-46 (1984).

(12) Paciorek, K.J.L., Kratzer, R.H.,

Kaufman, J., Nakahara, J.H., Christos, T., and

Hartstein, A.M. "Thermal oxidative

degradation studies of phosphate esters."

American Industrial Hygiene Association

Journal. 18:633-639 (1978).

(13) RTECS. "Registry of Toxic Effects of

Chemical Substances" (database). Cincinnati,

OH: National Institute for Occupational

Safety and Health (1988).

(14) Sasaki, K., Takeda, M., and Uchiyama.

M. "Toxicity, absorption and elimination of

phosphoric acid triesters by killifish and

goldfish." Bulletin of Environmental

Contamination and Toxicology. 27:775-782

(1981).

(15) Sasaki, K., Suzuki, T., Takeda, M., and

Uchiyama, M. "Bioconcentration and

excretion of phosphoric acid triesters by

killifish (Oryzeas latipes)." Bulletin of

Environmental Contamination and

Toxicology, 28:752-759 (1982).

(16) Sellstroem, U., and Jansson, B. "Mass

spectrometric determination of tris(1,3-

dichloro-2-propyl)phosphate (TDCP) using

NCl-technique." International Journal of

Environmental Analytical Chemistry. 29:277-

287 (1987).

(17) Sprague, G.L., Sandvik. L.L, BrookinsHendricks. M.J. and Bickford, A.A.

"Neurotoxicity of two organophosphorous

ester flame retardants in hens." Journal of Toxicology and Environmental Health, 8:507-

518(1981).

(18) Stauffer. The Stauffer Chemical

Company. Product Safety Information FyrolR

FR-2 (1979).

(19) Stauffer. The Stauffer Chemical

Company. "Summary of a two-year oral

toxicity/carcinogenicity study of Fyrol FR-2

in rats," EPA TSCA Test Submission 8EHQ1084-04015, Follow-up 88-8100282 (1981).

(20) USEPA. "Tris(1,3-dichloro-2-

propanol)phosphate." Chemical Hazard

Information Profile (CHIP), Draft Report.

Office of Pesticides and Toxic Substances,

U.S. Environmental Protection Agency

(August 31, 1981).

(21) Williams, D.T., and Label, G.L. "A

national survey of tri(haloalkyl)-, trialkyl-, and triarylphosphates in Canadian drinking water." Bulletin of Environmental

Contamination and Toxicology. 27:450-457

(1981).

(22) Williams, D.T., Nestmann, E.R., LeBel,

G.L., Benoit, F.M., Otson, R., and Lee, E.G.H.

"Determination of mutagenic potential and

organic contaminants of Great Lakes

(Canada, USA) drinking water."

Chemosphere. 11-283-276 (1982).

2.3.c Tetrakis(2-chloroethyl)ethylene

diphosphate-Summary of

recommended studies. It is

recommended that tetrakis(2-

chloroethyl)ethylene diphosphate

(TCEED) be tested for the following:

1. Chemical fate. Environmental

monitoring; water solubility; vapor

pressure; octanol/water partition

coefficient; biodegradtion.

2. Health effects. None.

3. Ecological effects. Acute toxicity to

fish, algae and aquatic invertebrates.

PHYSICAL AND CHEMICAL INFORMATION

CAS No. 33125-86-9

Synonyms ... .................................................. ............

Acronym..............................

Structural Formula:

Phosphoric acid, 1,2-ethanediyl (2-chloro-ethyl) ester (91);

Thermolin 101.

TCEEP.

o 0 II II

CICH 2CH 2O-P-OCH2CH2O-P-OCHCH2Cl I I

O 0

I I

=C 2 CHCHCl

46272
Federal Register / Vol. 53, No. 221 / Wednesday, November 16, 1988 / Notices

PHYSICAL AND CHEMICAL INFORMATON-Continued

CAS No. 33125-86-9

Empirical Formula ......................................................... C10HXC 4O5P2.

Molecular Weight ............................. 471.9.

Melting Point (*C( .............. . . . No information was found.

Boiling Point (*C) ........................... No information was found.

Vapor Pressure (mmHg) ..................... 0.85 at 25"C (Ref. 3, Olin, 1987). Solubility In Water (mg/L) ................................................... 3000 at 24*C (Ref. 3, Olin, 1987). Specific Gravity .................................................................... 1.45 at 25*C (Ref. 3, Olin 1987). Log Octanoll/Water Partition Coefficient (log P) .............. 1.16, estimated (Ref. 2, CLOGP, 1987). Henry's Law Constant ....................... 1.76 x o

- O 4 atm m3

/mol (calculated) Log Adsorption Coefficient ................................................ 2.0 (Ref. 1, CHEMEST, 1987) Description of Chemical ...................................................... Dark liquid under ambient conditions. (Ref. 3, Olin, 1987).

Rationale for Recommendations

L Exposure Information

A. Production/use. Tetrakis(2-

chloroethyl)ethylene diphosphate

(TCEEP) is produced in substantial

annual amounts in the U.S. but actual

production volumes are classified as

confidential business information.

TCEEP is used as an additive flame

retardant in flexible polyurethane foams

and may be used as a flame retardant in

various resins. There is no known

natural production of TCEEP.

B. Environmental release. It is likely

that most of the TCEEP production is

eventually released to the environment

as furniture, automobiles, construction

materials, etc. are scrapped and

disposed of in dumps and landfills.

Some TCEEP may be released during

thermal decomposition (in accidental

fires and incinerators) but no

information was found on thermal

decomposition.

C. Evidence for environmental

exposure. No information was found.

Related chioroalkyl phosphate flame

retardants (e.g., tris(2-

chloroethyl)phosphate and tris(1,3-

dichloropropyll-phsophate), when

looked for in the environment, have

been found at low concentrations in a

wide variety of environmental media in

industrialized countries. It is not known

whether anyone has looked for TCEEP

in the environment.

II. Chemical Fate Information

A. Transport. The water solubility,

vapor pressure and estimated octanol/

Water partition coefficient for TCEEP

suggest significant transport to both air

and water, with little sorption to soil or

sediment. The calculated Henry's law

constant, if true, would produce a halflife for volatilization from water of

about I to 2 days. A related phosphate,

the tris(2-chloroethyl)-phosphate, has a

reported Henry's constant of 1.81 x 10 - 7

atm m3

/mol for a predicted half-life in

water of about 1.4 years. It is difficult to

believe that there would be such a great

difference between these two

phosphates and the water solubility and

vapor pressure used to calculate the

Henry's constants should be reliably

measured. If this phosphate behaves

similarly to the

tris(chloroalkyl)phosphate flame

retardants, it will partition largely to

water following release to the

environment.

B. Persistence. No information was

found.

C. Rationale for chemical fate and

recommendations. TCEEP, like the

related tris(chloroalkyl)phosphate flame

retardants, may partition largely to the

aquatic environment and be relatively

persistent. The related

tris(chloroalkyl)phospates have been

found throughout the industrialized

world in a variety of environmental

media at low concentrations. There is a

need for monitoring studies that look for

TCEEP to determine if it also appears at

low concentrations in the environment.

In addition, it is recommended that

studies be conducted to determine the

water solubility, vapor pressure and

octanol/water partition coefficient of

TCEEP and to evaluate its

biodegradability in natural waters.

III. Biological Effects of Concern to

Human Health

The Committee, at the conclusion of

its Sixth Scoring Exercise, concluded

that it would not review TCEEP for

health effects (52 FR 10409, April 1,

1987). Therefore, no health effects

studies are being recommended at this

time.

W. Ecological Effects of Concern

A. Acute and subchronic (short-term)

effects. No information was found.

B. Chronic (long-term) effects. No

information was found.

C. Other ecological effects. No

information was found.

D. Bioconcentration and food-chain

transport. No information was found.

E. Rationale for ecological effects

recommendations. It is likely that

TCEEP has been and will continue to be

released to the environment in

significant quantitieswhere it may

persist and accumulate. Studies should

be conducted to evaluate the acute

toxicity of TCEEP to fish, aquatic

invertebrates and algae.

References

(1) CHEMEST. "A program for chemical

property estimation [data base]."

Washington, DC: U.S. Environmental

Protection Agency, Office of Pesticides and

Toxic Substances (1987).

(2) CLOGP. "A program for the estimation

of octanol/water partition coefficients [data

base]." Washington, DC: U.S. Environmental

Protection Agency, Office of Pesticides and

Toxic Substances (1987).

(3) Olin Corporation. Material Safety Data

Sheet on tetrakis (2-chloroethyl) ethylene diphosphate, and use information and

product data on Thermolin 101 flame

retardant additive provided by N.J. Barone of

Olin Corporation (May 26,1987).

2.4 Chemicals recommended without being

designated for response within 12 months--

2.4.a Butyroldehyde-Summary of

recommended studies. It is recommended

that butyraldehyde be tested for the

following:

1. Chemicalfate. Monitoring in the vicinity

of major manufacturing and use sites.

2. Health effects. In depth toxicology

evaluation if warranted by monitoring data.

3. Ecological effects. Toxicity studies with

representative biota if warranted by

monitoring data.

4R27R
Federal Register / Vol. 53, No. 221 / Wednesday, November 16, 1988 / Notices

PHYSICAL AND CHEMICAL INFORMATION

CAS No. 123-72-e I

Butanal (9CI);

Butyraldehyde (8C0);

n-Butyraldehyde;

Butal;

Butyric aldehyde;

n-Butyraldehyde;

Butanaldehyde;

Butyric aldehyde,

Structural Formula:

CH 3CHCH2CHO

Empirical Formula ............................................................ C -O.

Molecular W eight ................................................................ 72.10.

Melting Point (OC) .............................................................. .- 99 (Ref. 61,

Boiling Point (C) ................................................................. - 74.0 (Ref. 61

Vapor Pressure (mmHg) ..................................................... 92 @ 20' (Refo.

Solubility in water (mg/L) ................................................... 6,000 (Ref. 14,

Specific Gravity .................................................................... 0.8016 (Ref. 61

Log Octanol/Water Partition Coefficient (log P) .............. 0.88 (Ref. 15, E

Henry's Law Constant ........................................................ 1.4 x 10- (c al

Vapor Density In Air (air=1) ............ 2.5 (Ref. 14, E

DescriD Ilon of Chemicals .................. .... .. Cooaless liquid

Windholz, 1983).

Windholz, 1983).

14, Eastman, (1988).

Eastman, 1988). , Wlndholz, 1983).

ENVIROFATE, 1988).

Iculated).

istman, 1988).

with characteristic pungent, aldehyde odor (Ref. 25, Hawley, 1987).

Rationale for Recommendations

1. Exposure Information

A. Production/use/release to

environment Butyraldehyde is produced

and used in the U.S. at a rate in excess

of one billion pounds per year. SRI

reported U.S. production of

butyraldehyde in 1987 at 1.835 billion

pounds by five manufacturers at six

sites spread across Texas (Ref. 52, SRI

International, 1987). Greater than 90

percent of the production is used as a

chemical intermediate to synthesize nbutanol and 2-ethylhexanol. Domestic

production of n-butanol and 2-,

ethylhexanol was 935 million and 638

million pounds, respectively, in 1987

(Ref. 9, C&EN, 1988). Other important

uses for butyraldehyde include its use as

a solvent for surface coatings and its

combination with polyvinyl alcohol to

form a resin in laminated safety glass

(Ref. Butyraldehyde 8, CEH, 1985). occurs naturally in

many plants, including fruits and

vegetables, and in cheese, meats and

wines. It has FDA approval as a direct

food additive for use as a synthetic

flavoring substance and as an indirect

food additive as a component of

packaging (21 CFR 172.515; 21 CFR

175.105; and Ref. 44, Opdyke, 1979).

The major releases of butyraldehyde

to the environment will occur at the

manufacturing sites in Texas and at

major use sites elsewhere in the U.S.

This volatile water soluble chemical

may be released to water and air in

significant quantities. One company

(Ref. 14, Eastman, 1988) reported 1987

emissions at its Texas plant of about

831,000 pounds with 90 percent of the

emissions listed as fugitive emissions to

air. Toxic chemical release inventory

reporting forms submitted to the EPA in

response to the Toxic Chemical Release

Reporting rule (53 FR 4500; February 16,

1988) provide information on substantial

releases to air (from 54,000 to 836,000

lbs. per year) at six manufacturing and

use sites (Ref. 55, USEPA, 1988).

B. Evidence for human and

environmental exposure. According to

the National Occupational Hazard

Survey (NOHS) conducted by the

National Institute for Occupational

Safety and Health (NIOSH) from 197Z to

1974, 1,259 workers were potentially

exposed to butyraldehyde in the

workplace in 1970 (Ref. 38, NIOSH,

1976). Preliminary data available from

the National Occupational Exposure

Survey (NOES), conducted by NIOSH

from 1980 to 1983, indicate that 5,392

workers, including 950 women, were

potentially exposed to butyraldehyde in

the workplace in 1980 (Ref. 39, NIOSH,

1984). Since domestic production has

been increasing since 1982 (Ref. 56,

USITC 1983) it is expected that more

workers are exposed today.

Occupational exposure limits have not

been established by the American

Conference of Governmental Industrial

Hygienists or the Occupational Safety

and Health Administration.

One company (Ref. 14, Eastman, 1988)

reported that the major points of worker

exposure to n-butyraldehyde are in

sampling, loading, and unloading

shipping containers, and maintaining the

equipment. Also, during production at

its Texas plant, from 4 to 8 workers are

potentially exposed daily, and from I to

2 maintenance workers are potentially exposed for approximately 120 days per

year. The same company reported that

during use of n-butyraldehyde to

manufacture other chemicals, 12 to 18

workers are potentially exposed at its

Tennessee plant. These processes run

from 180 to 360 days per year. Personal

monitoring of production workers (42

samples) indicated air concentrations of

n-butyraldehyde averaging less than 1.0

ppm (8-hour.TWA) with no sample

above 1.25 ppm. Personal monitoring of

materials handling workers (7 samples)

indicated a geometric mean (-hour

TWA) of 3.7 ppm n-butyraldehyde. Five

of the seven samples were under 1.0

ppm, the other two were 21.3 and 4.57

ppm. (Ref. 14, Eastman, 1988).

Another company (Ref. 26, HoechstCelanese, 1988) reported that 120

employees were working in the

butyraldehyde unit of its Texas

processing plant. It reported no

monitoring data collected in previous

years, and only one sample collected in

1988 which "was I ppm for an 8 hour

period." It was not reported whether this

was a personal or area sample. Its

Texas purification plant (Ref. 26,

Hoechst-Celanese, 1988) reported 4 to 8

workers exposed to n-butyraldehyde

with monitoring data indicating

exposure levels less than 10 ppm.

However, no information was given

concerning the collection of monitoring

data.

There are no monitoring data

available showing general population

exposure to n-butyraldehyde. Exposures

may be significant for populations living

near major manufacturing sites since

bvnonwms ............................................ ..

46274
Federal Register / Vol. 53, No. 221 / Wednesday, November 16, 1988 / Notices

toxic release information indicates

substantial fugitive emissions from

manufacturing and use sites (Ref. 14,

Eastman, 1988; Ref. 55, USEPA, 1988).

One company (Ref. 26, HoechstCelanese, 1988), however, reported

community exposure near its Texas

processing plant to be less than 0.0004

ppm n-butyraldehyde although fugitive

emissions of butyraldehyde at the plant

exceeded 106,000 pounds per year.

Details of the sampling and other

procedures used to determine this

number were not reported.

Butyraldehyde was detected but not

quantified in the respired air of a

heterogenous nonsmoking control

population living in' Chicago and the

surrounding suburbs; however, it was

not detected in the respired air of two

other populations examined in the

study: A prediabetic group and a

diabetic group. The total sample was 62

persons. The authors classified

butyraldehyde as a physiologic volatile

metabolite but did not suggest a

mechanism for its generation (Ref. 34,

Krotoszynski and O'Neill, 1982).

No information was found concerning

drinking water exposures to nbutyraldehyde.

Many of the monitoring studies that

report environmental concentrations of

butyraldehyde have dealt with urban air

in areas where smogs are a problem.

This appears to be due to the presence

of butyraldehyde in the emissions from

internal combustion engines and the

involvement of butyraldehyde in smog

formation. Grosjean et al. have

conducted several of these studies in

Southern California (Ref. 17, Fung et al.,

1981; Ref. 21, Grosjean, 1982; Ref. 22,

Grosjean et al., 1983; Ref. 23, Grosjean

and Wright, 1983; and Ref. 24, Grosjean

and Fung, 1984). Similar studies have

been conducted in Sweden (Ref. 31,

Jonsson et al., 1985). Isodorov (Ref. 28,

1985) reported on the emissions of

butyraldehyde into the'atmosphere by

ferns in the forests of northern Russia.

Little or no monitoring data were found

on the presence of butyraldehyde in the

air near major manufacturing and use

sites although toxic release information

reveals substantial fugitive emissions at

manufacturing and use sites.

Some monitoring studies have looked

for butyraldehyde in surface, ground

and drinking waters and it has been

found at very low concentrations in a

few samples (Ref. 11, Corwin, 1969; Ref.

16, Ewing et al., 1977; and Ref. 58, Viar,

1988). No data were found on monitoring

conducted on water samples obtained

near manufacturing and use sites.

Ito et al. (Ref. 29, 1980) reported

finding butyraldehyde in fish in Japan.

.11. Chemical Fate Information

A. Transport. Based on its vapor

pressure, water solubility and log P,

butyraldehyde released to the

environment will partition to both water

and air. The Henry's law constant for

butyraldehyde indicates that

butyraldehyde in surface waters will

volatilize rapidly with a half-life in

water of about 12 hours.,

B. Persistence. Butyraldehyde

released to the environment will not

persist. It will be rapidly degraded in the

atmosphere by reaction with hydroxyl

radicals with an atmospheric half-life of

4 to 9 hours (Ref. 14, Eastman, 1988).

Butyraldehyde is readily biodegraded

under both aerobic and anaerobic

conditions by acclimated

microorganisms.

C. Rationale for chemical fate

recommendations. Butyraldehyde

released to the environment will not

persist and concerns for potential

adverse effects are low in most parts of

the U.S. However, the large production

volumes at sites in Texas and the toxic

release data on substantial releases to

air at manufacturing and use site raise

concerns with respect to environmental

concentrations of butyraldehyde in air

and water at those sites. Those

emissions will occur on a nearly

continuous basis and butyraldehyde

may be present in the air and water at

significant concentrations that represent

a balance between rates of release and

rates of removal by degradation

processes. It .is recommended that

monitoring studies be conducted to

determine butyraldehyde concentrations

in air and water in the vicinity of the

major manufacturing and use facilities.

Monitoring for the presence of low

molecular weight, volatile, hydrophilic

compounds in water samples, as noted

by Ogawa and Fritz (Ref. 43, 1985), can

be very difficult and special care should

be taken to assure realistic results.

III. Biological Effects of Concern to

Human Health

A. Metabolism and pharmacokinetics.

Aldehydes are oxidized to the

corresponding acid by the enzyme

aldehyde dehydrogenase (Ref. 59,

Weiner, 1980) Three isozymes have been

identified from human liver, all of which

oxidized several aldehydes, including

butyraldehyde (Ref. 30, Jones and Teng,

1983).

Butyraldehyde has been detected in

mother's milk (6 or 8 samples) obtained

from urban areas in the U.S. (Ref. 45,

Pellizzari et al., 1982) and in the sera of

normal and diabetic patients (Ref. 62,

Zlatkis et al., 1980).

In virto studies indicate that

butyraldehyde at concentrations of 0.1

to 1 mM inhibits multiplication of mouse

sarcoma cells in culture (Ref. 46, Pilotti

et al., 1975; Ref. 13, Curvall et al., 1984),

and inhibits chemotaxis and reduces

viability of human polymorphonuclear

leukocytes at 90 mM (Ref. 3, Bridges et

al., 1977). Other in vitro effects incliuded:,

damage to the cell membranes of human

fibroblasts at 25 mM (Ref. 54, Thelestam

et al., 1980; Ref. 13, Curvall et al., 1984)

and human red blood cells at 1mM (Ref.

47, Poli et al., 1987), and Interference

with lipolysis and glucose metabolism in

adipose tissue cells at concentrations of

I to 20 mM (Ref. 20, Giudicelli et al.,

1973).

B. Acute and subchronic (short-term)

effects. The acute toxicity data for

butyraldehyde are summarized in the

following Table 3.

TABLE 3.-TOXICITY OF BUTYRALDEHYDE IN LABORATORY ANIMALS

LC5O LDO

Species Duration Concentration Dermal (mg/ Reference

(hours) (mg/m 3

) Oral (mg/kg) kg) _

Rat ...... ....................................... 2,490 ............. Marhold (1972, as cited in RTECS, Ref. 48).

Rat .................................... 4 >23,590 5,890 ............................. Smyth at al. (1951, Ref. 51).

Rat ............................... 0.5 174,000 ....................................... ................. Skog (1950, Ret. 50).

Mouse ...... ........................................ zmerov (1982, as cited in RTECS, Ret. 48).

Rabbit .... ............ ........................................... 3 ,560 'Union Carbide Data Sheet (1967, as cited in RTECS, Ref. '48).

Guinea pig ........................ .............................. . .................... .. ................. ....... . >16 Brabec (1981, Ref. 2).

"One of six animals died.

46275
Federal Register / Vol. 53, No. 221 / Wednesday, November 16, 1988 / Notices

Inhalation toxicity in males of two

mouse strains was defined by a 50

percent reduction in respiratory rate

(RD50) following exposure of 3 or 4 mice

per dose (dose range not specified] for

10 minutes (Ref. 53, Steinhagen and

Barrow, 1984). An RD50 of 1,532 ppm

(4,518 mg/m3) was determined for

B6C3F1 mice, and an RD50 of 1,015 ppm

(2,993 mg/M) was determined for

Swiss-Webster mice. An RD50 of 5,572

ppm (16,431 mg/m s} was determined for

male rats under similar conditions (Ref.

1, Babiuk et al., 1985).

Inhalation exposure of ten SpragueDawley derived CD rats to measured

concentrations of 1,820 ppm (5,367 mg/L)

butyraldehyde for 4 hours caused

irritation of the ocular and respiratory

mucous membranes during the exposure

and subsequent 4 hours (Ref. 26,

Hoechst-Celanese, 1988). No other

treatment-related effects were reported

during the 14-day observation period or

at necropsy.

Inhalation exposure of rats to 1,000

ppm (2,949 mg/ml) butyraldehyde for

twelve 6-hour exposures produced no

observable toxic signs (Ref. 18, Gage,

1970.

Oral administration of butyraldehyde

to rats at dose levels of 0.075, 0.15, 0.3,

0.6, or 1.2 g per kg, daily for 5 days per

week for 13 weeks caused irritation,

inflammation, necrosis, hyperplasia, and

lesions in the forestomach and gastric

mucosa (Ref. 40, NTP, 1988). The

increased incidence of these lesions was

dose-related and affected 100 percent of

the males and 90 percent of females at

the highest does level, 1.2 g/kg.

Dermal exposure of rabbits to

butyraldehyde (2.5 mL/kg) for 24 hours

caused severe dermal lesions that

became infected and led to termination

of the study after 7 days (Ref. 26,

Hoechst-Celanese, 1988). Extensive

necrosis and severe edema were

exhibited by all animals at 24 hours;

eschar developed about day 4 or 5.

Toxic signs evident in several animals

during the 24-hour application period

included ataxia, fine tremors,

hypoactivity, and respiratory anomalies.

Tremors, hypoactivity, hypopnea and

respiratory arhythmia persisted in a few

aniamls for an unspecified period of

time. Apart from the dermal lesions, no

other treatment-induced changes were

evident at necropsy.

Butyraldehyde is a severe skin and

eye irritant in rabbits (Ref. 26, HoechstCelanese, 1988). It exhibits little or no

potential to produce dermal

sensitization in guinea pigs (Ref. 26,

Hoechst-Celanese, 1981). After a 3-week

induction period consisting of nine 6-

hour applications of butyraldehyde,

there was no dermal response from

guinea pigs challenged with 10 percent

butyraldehyde. A second challenge at 25

percent elicited an equivocal response

in only 2 of 20 animals.

C. Genotoxicity. In the Salmonella

assay, butyraldehyde was not mutagenic

in strains TA1535, TA1537, TA98, or

TA100, with or without activation (Ref.

35, Mortelmans et al., 1986). No increase

in chromosomal aberrations was

detected in Chinese hamster ovary cells

at butyraldehyde concentrations of 59 to

135 ug/mL with or without metabolic

activation, but sister chromatid

exchange was induced in these cells at

nontoxic levels ranging from 9 to 90 ug/

mL (Ref. 19, Galloway et al., 1987). The

lowest effective doses were less than 9

ug/mL without activation and 30 ug/mL

with activation. When butyraldehyde

was administered to male mice (Q

strain) in the drinking water at 0.2 mg/L

for 50 days, chromosomal aberrations

were evident as polyploidy at all stages

of spermatogenesis and abnormal

pairing of chromosomes at metaphase I

(Ref. 37, Moutschen-Dahmen, 1976).

Butyraldehyde did not increase sister

chromatid exchange in human

lymphocytes treated in vitro at a

concentration of ZX10-3 percent (v/v)

without metabolic activation (Ref. 42,

Obe and Beck, 1979). No increase was

reported in sex-linked recessive lethals

of Drosophila melanogaster fed

butyraldehyde at a concentration of

2,000 ppm in 5 percent aqueous sucrose

(Ref. 57, Valencia et al., 1985).

D. Oncogenicity. No information was

found on the subject compound. Plans

for a chronic inhalation bioassay of

butyraldehyde were dropped by NTP

because of technical difficulties in

generating the atmosphere for exposure

(Ref. 41, NTP, 1988). A related

compound, isobutyraldehyde, is

scheduled for a chronic inhalation

bioassay starting in February 1989 under

the National Toxicology Program. Other

structural analogues of n-butyraldehyde

including formaldehyde and

acetaldehyde have shown sufficient

evidence for carcinogenicity in animal

studies; the evidence in humans is

considered by IARC to be limited for

formaldehyde and inadequate for

acetaldehyde (Ref. 27, IARC, 1987).

E. Chronic (long-term) effects. No

information was found.

F. Reproducitve and developmental

effects. A single intraperitoneal injection

of I mg butyraldehyde per animal

produced chromosomal damage and

meiotic anomalies including

degenerative nuclei, multispindle cells

and polyploid cells at all stages of

spermatogenesis in male mice I month

following the treatment (Ref. 36,

Moutschen-Dahmen et al., 1975). In a

later study (Ref. 37, Moutschen-Dahmen

et al., 1976), one group of male mice

received a single intraperitoneal dose of

30 mg butyraldehyde per kg, and a

second group received 0.2 mg/L in their

drinking water for 50 days.

Administration of butyraldehyde by

either route damaged the spermatogenic

cells of the seminiferous tubules. In

addition to gross degeneration,

polyploidy was observed at all stages of

spermatogenesis and abnromal pairing

of sex chromosomes occurred at

metaphase I; there was increased

incidence of spermatozoa without

acrosomes in the vas deferens.

G. Observations in humans. Among 12

individuals of Oriental ancestry

characterized as susceptible to

cutaneous flushing after ingestion of

ethanol, all reacted positively (with

erythema) to patch testing with 75

percent butyraldehyde (Ref. 60, Wilkin

and Fortner,' 1985).

Butyraldehyde was found to be mildly

irritating when applied in epicutaneous

tests (Ref. 44, Fiser and Pokorny, 1965,

as cited in Opdyke, 1979), whereas 1

percent butyraldehyde in petrolatum

produced no irritation after a 48-hour

closed patch test (Ref. 44, Kligman 1977,

as cited in Opdyke, 1979). One out of 25

tested with 1 percent butyraldehyde in

petrolatum had a positive but

nonspecific sensitization reaction in a

maximization test.

Butyraldehyde vapor (230 ppm) was

nonirritating to the eyes of 15 men

during a 30 minute exposure (Ref. 49,

Sim and Pattle, 1957).

H. Rationale for health effects

recommendations. Annual domestic

production of n-butyraldehyde is about

1.8 billion pounds by five manufacturers

at six sites in Texas. Preliminary data

indicate that over 5,000 workers

(including 950 women) were potentially

exposed to n-butyraldehyde in the

workplace in 1980. Since domestic

production has been increasing since

1982, it is expected that more workers

are exposed today.

Sizeable airborne fugitive emissions

have been reported (from 54,000 to

836,000 lbs. peryear) from six major

manufacturing and use sites. Therefore,

there is potential for significant

community population exposure in the

vicinity of manufacturing and use sites.

Structural analogues of nbutyraldehyde including formaldehyde

and acetaldehyde have shown

carcinogenic effects in animals. IARC

considers that there is sufficient

evidence from animal studies for the

carcinogenicity of formaldehyde and

acetaldehyde whereas the evidence in

humans is limited or inadequate,

46276
Federal Register / Vol. 53, No.- 221 / Wednesday, November 16, 1988 / Notices 46277

respectively. The National Toxicology indicating impaired spermatogenesis in should be conducted if warranted by

Program is scheduled to perform a 2- male mice. Considering the lack of monitoring data.

year inhalation study with definitive data, the Committee IV. Ecological Effects of Concern

isobutyraldehyde. There are, however, recommends that testing addressing

no data available to assess the carcinogenicity and reproductive and A. Acute and subchronic (short-term]

carcinogenicity of n/butyraldehyde developmental effects of butyraldehyde effects. Acute toxicity (LC50) values

itself. The Committee noted the data have been reported as shown below.

Organism Endpoint Cocy(sl) Reference

Fathead minnow ...................................................................................................................... 96-hr LCS0 25.8 Ref. 12, Curtis and W ard, 1981.

Golden Orfe ............................................................................................................................. 96-hr LC50 57 & 114 Ref. 32, Juhnke and Ludemann, 1978.

Aedes aegyp larva a .................................................................................................................. 4-hr LC50 2,000 Ref. 33, Kramer et al., 1983.

B. Chronic (long-term) effects. No

information was found.

C. Other ecological effects. In a series

of articles, Bringmann and Kuhn

reported on minimum inhibitory

concentrations for a large number of

chemicals and a variety of aquatic

organisms. The definition of minimum

inhibitory concentration varied

according to the organism being tested.

For daphnids it was described as the

maximum tested concentration at which

all of the daphnids were able to retain

their swimming capability following 24

hours exposure to the test chemical. For

protozoa the minimum inhibitory

concentration was the concentration

that caused cell counts in test cultures to

be 5 percent or more below the counts in

control cultures with 48 hours exposure.

For algae, the minimum inhibitory

concentration was the concentration of

test material that inhibited cell

multiplication in test versus control

cultures during 8 days exposure. For the

bacterium, Pseudomonasputida, the

endpoint was inhibition of cell

multiplication after 24 hours exposure,

as determined by turbidity

measurements of test versus control

cultures (Ref. 4, Bringmann, 1978; Ref. 5,

Bringmann and Kuhn, 1980; Ref. 6,

Bringmann and Kuhn, 1981; and Ref. 7,

Bringmann and Kuhn, 1982). Their

results with butyraldehyde are

summarized below:

Minimum

Organisminhibitory Organism concentration

(mg/L)

MAicocystis aeruginosa algae ......... 19

Scenedesmus guadicauda algae.. 83

Entosohon sulcatum protozoa 4.2

Urunerna parduczi protozoa ........... 98

Chilomonas paramaecium proto- zoa .......................................... 44

Daphnia magna ................................. 100

Pseudomonas pu&(da bacterium...... . 100

The butyraldehyde concentrations

that inhibited the swimming capability

of 50 percent and 100 percent of

Dcphnio magna populations after 24-

hours exposure also were reported by

Bringmann and Kuhn (Ref. 7, 1982) to be

195 and 383 mg/L, respectively.

Chou et al. (Ref. 10, 1978) reported

that butyraldehyde was relatively nontoxic to methanogenic bacteria.

In a study on the use of bacteria as an

indication of toxicity to fish, Curtis et al

(Ref. 12,1981) reported a 5-minute EC50

of 16.4 mg/L for Photobacterium

phosphoreum exposed to butyraldehyde.

D. Bioconcentration and food-chain

transport. An examination of fish in

Japan revealed the presence of

butyraldehyde at low concentrations

(Ref. 29, Ito et al., 1980]. The significance

of this information in unclear since

butyraldehyde is produced naturally

and is found in many food products.

Based on its high water solubility and

low octanol/water partitioning

coefficient, butyraldehyde is not

expected to bioconcentrate.

E. Rationale for ecological effects

recommendations. Butyraldehyde is

produced in very large annual quantities

at several locations in Texas. There are

reports of substantial emissions of

butyraldehyde to air at manufacturing

and use sites. There may be significant

concentrations of butyraldehyde in the

air and surface waters in the vicinity of

one or more of the manufacturing and

use sites. Few data are available on the

acute toxicity of butyraldehyde to

aquatic species and none were found for

terrestrial plants and animals. No

chronic toxicity information was found.

It is recommended that appropriate

toxicity studies be conducted with

representative species of biota if

warranted by monitoring data.

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IFR Doc. 88-26300 Filed 11-15-88; 8:45 am]

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