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

ENVIRONMENTAL PROTECTION
AGENCY (OPTS-41030; FRL-3476-61 

### Twenty-Third Report ofthe Interagency Testing Committee to the Administrator, Receipt of Report and Request for Comments Regarding Priority Listof 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 ofEPA 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 oftest rules under section 4(a) ofthe 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 arenot designated for
response within 12 months. Crotonaldehyde (CAS No. 4170-30-3), which was recommended with intent-todesignate by the ITC inits TwentySecond Report (53FR 18196; May 20, 1988), nowis designated forresponse within 12 months. In response to ITC's designation, EPA will either initiate rulemaking under section 4(a) ofTSCA.

orpublish a Federal Register notice explaining the reasons fornotinitiating 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, EPAis soliciting interest inpublic participation in the consent agreement process fortris(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 thepriority list. DATES: Written comments should be submitted by December 16, 1988. Submit written notice of interest in being designated an "interested party" to development ofconsent 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 PublicDocket Office (TS-793), Office ofToxic 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 publicrecord 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 theFocus 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 ofthe 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. 2003et seq;15 U.S.C. 2601 et seq.)authorizes the Administrator ofEPA to promulgate regulations under section 4(a) requiring testing ofchemical 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) ofTSCA established an Interagency Testing Committee to make recommendations to the Administrator ofEPAon chemical substances and mixtures to be given priority consideration in proposing test rules under section 4(a). Section 4(e) directs the ITCto revise its list of recommendations at least every 6 months as necessary. The ITCmay "designate" up to 50 substances and mixtures at any one time forpriority consideration by the Agency. .Crotonaldehyde is a designated chemical. For such designations, the Agency must within 12 months either intitiate rulemaking orissue in the Federal Registerits reasons fornot 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.
ILWritten 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 Part716), which requires the reporting ofunpublished 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 ofproduction 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 therange of issues/effects which will be the focus of the Agency's subsequent activities in responding to the ITCrecommendations. TheFocus Meetings will be held on December 13, 1988, as follows: 9:30 a.m.Tris(2-chloroethyl)-phosphate,

three tris(chloroprophyl)-phosphates, andtetrakis(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 fortris(2-chloroethyl)- 

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### 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 laterthan December 16, 1988. The procedures fornegotiations are described in40 CFR 790.22. All written submissions should bear the identifying docket number (OPTS-41030).
III. Status ofList

In addition to adding the six recommendations to the priority list,the ITC's Twenty-Third Report notes the removal oftwo chemicals from the list. Ethylbenzene has been removed from the listbecause the data gaps previously identified by the ITC have been satisfactorily resolved. Subsequent to ITC'spreparation ofits 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 listcontains 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, ExistingChemical Assessment Division.

- 

### TWENTY-THIRD REPORT OFTHE TSCA INTERAGENCY TESTING COMMITTEE TO THE ADMINISTRATOR, ENVIRONMENTAL PROTECTION AGENCY
Summary

Section 4 ofthe Toxic Substances 

### Control Act of1976 (TSCA, Pub.L 94- 469) provides for the testing of chemicals in commerce that maypresent

anunreasonable risk ofinjury to health

or the environment. It also provides for the establishment ofa Committee (ITC), composed ofrepresentatives from eight designated Federal agencies, to recommend chemical substances and mixtures (chemicals)to which the Administrator ofthe U.S. Environmental Protection Agency (EPA) should give priority consideration for the promulgation oftesting rules.

Section 4(e)(1)(Al ofTSCA directs the Committee to recommend to the EPA Administrator chemicals to which the Administrator should give priority consideration for the promulgation of testing rulespursuant to section 4(a). TheCommittee isrequired 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 fornot initiating such aproceeding. 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 ofits deliberations, the Committee is revising the TSCA section 4(e) Priority List by the addition of6 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 ofchemicals 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 ofrules promulgating automatic reporting requirements for non-designated ITCrecommendations 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 forpriority consideration byEPA without being designated for response within 12 months. The changes to the Priority List are presented, together with the types oftesting 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. Recommendedwith

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

WithoutBeing 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 effectsand reproductive effects. Health effects recommendations apply onlyto 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 (9Cl) 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 

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### 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 InteragencyTesting Committee Statutory Member Agencies and Their Representatives
Council on Environmental Quality

William Mills, Member 1 Department ofCommerce

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 ofAgriculture

Richard M. Parry, Jr. Elise A. B. Brown Department ofDefense

Harry Salem 2 Melvin E. Anderson 2 Department ofthe Interior

Gregory J.Smith 3 Martha L. Gay 4

Food and Drug Administration

Arnold Borsetti National Library ofMedicine

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 ITCby the staffof Dynamac Corporation (technical support contractor) and personnel ofthe EPA Office ofToxic 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 ofthe 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 ofa Priority List, which is to be published in theFederal Register. The Committee is directed by section 4(e)(1)(A) ofTSCA 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) orpublishing the Administrator's

reason fornot initiating such a proceeding. There is no statutory time limit forEPA response regarding chemicals that ITChas 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 ofthis report. The Committee's chemical review procedures and priority recommendations are described in previous reports (Refs. 1through 7).

1.2 Committee's previousreports. Twenty-two previous reports to the EPA Administrator have been issued by the Committee and published in the Federal Register (Refs. 1through 7). Ninety-six entries (seventy-six chemicals and twenty groups ofchemicals) were recommended forpriority consideration by the EPAAdministrator and designated for response within 12 months. In addition, 24 chemicals and

one group ofchemicals 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 ofchemicals. A complete list ofrecommended 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'sactivitiesduringthis reporting period. Between April 22, 1988 and October 20, 1988, the Committee continued toreview 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 ofthose contacted providedunpublished information on current production, exposure, uses, and effects ofchemicals under studyby 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 ofethylbenzene 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 ofthe data developed during the above studies.The Committee has reviewed the data developed in those studies and has concluded that all ofthe 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 section4(e)Priority List Section 4(e)(1)(B) ofTSCA directs the Committee to: "* * * make such 

### revisions in the [priority] list as it 

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### 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 therevisions." 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, forrepsonse 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 ofa Notice ofProposed Rulemaking (53 FR 35838; September 15, 1988) and ethylbenzene (CAS No. 100- 41-4) is being removed forthe 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 ofChemicals Designated for Response Within 12 Months, B. Chemicals and Groups ofChemicals Recommended with Intent-to-Designate, and C. Chemicals and Groups of Chemicals Recommended Without Being Designated forResponse 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)-methylammonio-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 ofthe TSCA Interagency Testing Committee to the Administrator, Environmental Protection Agency. TSCA Interagency Testing Committee, May 21, 1985, 50 FR 20930-20939. Includes references to Reports I through 15 and an annotated'list ofremovals.

(2) SeventeenthReport ofthe TSCA Interagency Testing Committee to the Administrator, Environmental Protection Agency. TSCA Interagency Testing Committee. November 19, 1885, 50 FR47603- 47612. (3)Eighteenth Report ofthe TSCA Interagency Testing Committee to the Administrator, Environmental Protection Agency. TSCA Interagency Testing Committee, May 19, 1986, 51 FR 18368-18375.

(4) Nineteenth Report ofthe TSCA Interagency Testing Committee to the Administrator, Environmental Protection Agency. TSCA Interagency Testing Committee, November 14,1986,51 FR41417- 41432.

(5) Twentieth Report of theTSCA Interagency Testing Committee to the Administrator, Environmental Protection Agency. TSCA Interagency Testing Committee, May 20,1987, 52 FR 19020-1902,.

(6) Twenty-first Report ofthe TSCA Interagency Testing Committee to the Administrator, Environmental Protection Agency. TSCA Interagency Testing Committee, November 20,1987, 52 FR44830- 44837.

(7)

Twenty-second Report ofthe 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) ofTSCA, 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 ofCommittee members.

2.2 Chemicalsdesignated forresponse within 12months-2.2.a Crotonaldehyde. In the twenty-second report to the Administrator ofEPA (53 FR 181,96) crotonaldehyde was recommended with intent-to-designate. Therationale 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 

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### Federal Register 

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

manufacturers ofcrotonaldehyde under the TSCA section 8(a) Preliminary Assessment rule; health and safety studies submitted underTSCA 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 forthe reasons previously presented (53 FR 18196) the Committee is now designating crotonaldehyde for response within 12months and recommending that it be tested for the following:

1. Chemical fate.Volatilization rate from water,aerobic aquatic biodegradation rate.

2. Healtheffects. None. 3.Ecologicaleffects. Acute toxicity to algae, fish and aquatic invertebrates.

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

### chloroethyl)phosphate-Summary of recommendedstudies,It is recommended that tris(2- chloroethyl)phosphate (TCEP)be tested for the following:

1.Chemical Fate.Environmental monitoring; vapor pressure; biodegradation,

2.HealthEffects.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--CHCH 2

## Cl


# 0 = P-0-CHCHCl

Fn O-CHCHCl

Emo" ca

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

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

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

................................................................ Vapor Pressure (m m

Hg)

................................................... Solubility inW 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 Retardant3CF. TCEP.

Cst2 CHaW 4 . 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 forRecommendations
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 forflexible 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 forbuilding insulation mterials. It is unlikely that there is any natural production ofTCEP.Most ofthe 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 ofTCEP remains intact afterthermal oxidation in air at 370°C. However, Paciorek et al. (Ref.23, 1978) reported that 85 percent of the TCEP chlorine was accounted forin volatileproducts ofdegradation at 370C,which indicates that no more than 15 percent ofthe TCEP was left undegraded.

B. Evidence forenvironmental 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 of16 sites at Kitakyushu (Ref.12, Ishikawa et al., 1985b) and in Canadian rivers at 13 sites, with a mean concentration of 8.7ng/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 of0.28 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 of3
to 9.6 ng/L at 4 of5 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 inJapan contained from 540 to 1,200 ng/L TCEP in the influent to the plants and 500 to 1,200 

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# / 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/LTCEP and the effluents were found tohave 190 to 1,500 ng/L (Ref.13, Ishikawa et al., 1985c). Five river and ocean sediment samples from Japan contained 13 to 28 ngTCEP/g ofsediment. 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 ofinfant 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 of0.3 ug/L. Drinking water in Japan, examined over

a 1-year period, contained 2to 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 of2.6 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 ofdrinking water samples in England, Fielding et al. (Ref.6, 1981) found TCEPin one offourteen 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 etal. (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 ofinfant and toddler diets from October 1979 through September 1980, Gartrell et al. (Ref.8, 1985b) reported TCEPin composite fruit and fruitjuice samples at an average concentration of0.2 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/gTCEP (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 isreported tobe from 7,000 (Ref. 17, LeFaux, 1968) to8,300 mg/L (Ref.11, Ichikawa et al., 1985a). A measured value of7,943 mg/L was reported by Yoshioka atal. (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 thatTCEP, 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 ofTCEP in water with some partitioning to air, sediments and biolipids.

B. Persistence. The trialkylphosphates, ingeneral, are resistant to hydrolysis and free-radical oxidations although hydrolysis at the pH ofsea water (approximtely 8.5) may be significant.TCEP is expected to demonstrate similarresistance to hydrolysis and oxidation, although no data were found. Biodegradation is probably the majordegradation mechanism in nature but the available data, which indicate that biodegradation is slow, are mostly circumstantial. There

are reports ofvery little biodegradation ofTCEP 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). TCEPwas reported to be hardly degraded after50 hours in activated sludge (Ref. 11, Ishikawa, et al., 1985a).

C. Rationale forchemical fate recommendations. There is widespread contamination ofthe 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 itswater solubility and octanol/water partition coefficients, TCEPreleased 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 innatural 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 ofConcern 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 ofTCEP for health effects pending receipt and review of data from the NTP study.

IV. Ecological Effects ofConcern

A. Acute andsubchronic(short-term) effects. The 96-hour LC50 ofTCEP 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/ Lwith a flatworm (Dugesia japonica). Another literature report (Ref. 5, Eldefrawi et al., 1977) stated that 5 mg/L TCEPhad 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 aweak inhibitor ofacetyl-cholinesterase and this may produce some chronic effects.

C. Otherecological effects (biological, behavioral, orecosystemprocesses) No information was found.

D. Bioconcentration and food-chain transport. The bioconcentration ofTCEP

was examined by Sasaki et al. (Ref. 26, 1981 and Ref. 27,1982) in both static and continuous-flow studies. Static tests withkillifish and goldfish showed bioconcentration factors (BCFs) of2 and 1, respectively. A BCF of I was observed forkillifigh in continuous-flow studies

over a 10-day period. When the fish

were placed in clean water there was rapid depuration with halfgone in 0.7 hours after-cessation of exposure.

E. Rationale forecologicaleffects recommendation. The widespread

occurrence ofTCEP in environmental samples raises concerns for its 

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ecological effects. On the other hand, the available data indicate that acute toxicity levels for fish and aquatic invertebrates are 1,000 times ormore greater than observed environmental concentrations. However, there were no data on plants and itis recommended that TCEPbe tested for acute toxicity to aquatic and terrestrial plants. There appear to be chronic exposures to low concentrations ofTCEP in aquatic environments and reports ofspine deformations raise concerns forchronic effects. Therefore, it is recommended thatTCEP 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-kenEiseiKenkyusho Kenkyu Hokoku. 19:1-6 (1984).

(2)Aldrich. Aldrich Chemical Company. 

### Catalog Handbook ofFine 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."Journalof 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 ofPesticides and Toxic Substances (1988).

(5) Eldefrawi, A.T., Mansour, N.A., Brattsten, LB., Ahrens, V.D., andLisk, D.J. "Further toxicologic studies with commercial and candidate flame retardant chemicals. Part U." Bulletin of Environmental Contamination andToxicology.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. 47pp. (1981).

(7) Gartrell, M.J., Craun, I.C., Podrebarac, D.S., and Gunderson, E.L. "Pesticides, selected elements and otherchemicals in infant and toddlertotal diet samples, October 1978-September 1979." Journal of

Association ofOfficialAnalyticalChemists.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 andtoddler total diet samples, October 1979-September 1980," Journal of

Association ofOfficialAnalyticalChemists.68(6):1163- 1183 (1985b).



### (9) Haraguchi, K.,Yamashita, T., and Shigemori, N. "Sampling and analysis of phosphoric acid triesters in ambient air." Taiki OsenCakkaishi 20,407-415 (1985).



### (10) Hutchins, S.R.,Tomson, M.B., Wilson, J.T., andWard, C.H."Fate oftrace organics duringrapid infiltration ofprimary wastewater atFortDevens,Massachusetts." WaterResearch.18:1025-1036 (1984). (11) Ishikawa, S., Shigezumi, K., Yasuda, K., and Shigemori, N "Behavior oforganic phosphate esters in several waste water treatment processes." SuishitsuOdaka Kenkyu, 8:799-807 (1985a).

(12) Ishikawa, S., Taketomi, M,,and Shinohara, R. "Determination oftrialkyl and triaryl phosphates in environmental samples." WaterResearch.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." SuishitsuOdako Kenkyu 8:529-535 (1985c).

(14) Kenmochi, U.,Matsunaga, K., and Ishida, R., "The effects ofenvironmental pollutants on biological systems. 6. Organic phosphates in environments." Okoyamaken KankyoHoken Senta Nenpo.5:167-175 (1981).

(15) Kirk-Othmer. Kirk-Othmer EncyclopediaofChemicalTechnology.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 oforganic contaminants in drinking water derived from the Great Lakes." Advances in ChemistrySeries. 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 ofResearch and Development. 321 pp.(Nov. 1984).

(19)Meliers, A.P., and Van der Leer, R., Chr. "The occurrence oforganic 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 oforganic compounds adsorbed on granular activated carbon filters used in treatment plants." WaterChlorination, Environmental Impact andHealthEffects.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 Handbookof 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), July21,1988.

(23) Paciorek, K.J.L. Kratzer, R.H., Kaufman, I., Nakahara, J.H., Christos, T., and Hartstein. A.M. "Thermal oxidative degradation studies ofphosphate esters." AmericanIndustrial HygieneAssociation Journal. 39(8):1633-639 (1978). (24) Piet, G.J.. Morra, C.H.F., and DeKruijf, M.A.M. "Thebehaviour oforganic micropollutants during passage through the soil." StudiesinEnvironmentalScience. 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 andToxicology" 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 andToxicology.27:775-782 (1981).

(27) Sasaki, K., Suzuki, T., Takeda, M., and Uchiyama, M. "Bioconcentration and excretion ofphosphoric acid triesters by killifish (Oryzeaslatipes)."Bulletinof Environmental Contamination and Toxicology.28:752-759 (1982).

(28) Sax, N.L. and Lewis Sr., R.J. Hawley's CondensedChemicalDictionary. 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 ofmutagenic potential and organic contaminants ofGreat Lakes (Canada, USA) drinking water." Chemosphere.11(3):263-276 (1982).

(31) Yoshioka, Y., Ose, Y., and Sato, T. "Correlation offive test methods to assess chemical toxicity and relation to physical properties." Ecotoxicityand Environmental Safety. 12:15-21 (1986).

2.3.b Tris(chloropropylphosphates-- Summaryofrecommendedstudies.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.Healtheffects. 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. Healtheffects. 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:



## ~H 3



### CH CH

CHCI---CH,



### H

Empirical Formula

................... ................... ..... C.H.C60.P, Molecular Weight

................................................................ 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. SpecificGravity........................................................ 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 

### 46269

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

PHYSICAL AND CHEMICAL INFORMATioN-Continued

Synonyms

............................................................................

Acronyms

............................................................................. Structural Formula:



### CH2CI 0 CHSCI

CH 2 

### CI 

## 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 forRecommendations

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 ofthe 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 ofTDCP 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) thatTDCP 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;

ins~ll -unlOromrun" FYROL FR2; PF38 TDCP: TDCPP.

C(lHCI 6O

4 P. 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 forenvironmental
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 of5 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 ofdrinking water from the Great Lakes at twelve Canadian Cities, Williams et al. (Ref.22, 1982) found concentrations ofTDCP at 0.1 to 15.7 ng(L. A study ofactivated carbon filter beds used at 40 U.S. drinking water
treatment plants found tris(chloropropyl)phosphate (notfurther 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 ofSwedish 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 ofhuman adipose tissues, LeBel and Williams (Ref. 8,1983) found TDCP in 5 of16 samples at 0.5 to 110 ng/
g. TDCP also was found at 5 to 50 ppb in 34 of123 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 importedproducts.

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 orTCIP and monitoring should be conducted ifcontinued high production and use are confirmed. Additional monitoring studies to evaluate the concentrations ofTDCP 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 to1,000 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 TCPPand TCIP. Themonitoring evidence (see I.B., above) forTDCP demonstrates widespread occurrence of TDCP inwater with some partitioning to sediments and biolipids. TCPP and TCIP

are expected to behave similarly.

B.Persistence. No information was found for TCPP,TCIPor 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 forchemical fate recommendations. There is widespread contamination ofthe environment by TDCP. There may be persistent background levels ofTCPP and TCIP in the environment but this is unknown. There is a need to conduct appropriate monitoring studies to determine ifTCDD and TCIP, like similar tris(chloroalkyl)phosphate flame retardants, are present in the environment at low concentrations and whether the environmental concentrations ofTDCP are increasing. There also isa 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 theirbiodegradability in natural waters.
II. Biological Effects ofConcern to Human Health

The Committee determined that tris(1,3-dichloro-2-propyl)phosphate (CAS No. 13674--87-8 has-been studied extensively forhealth effects and concluded that additional studies are not required. Therefore, health effects testing is not being recommended at this time.

A. Metabolismandtoxicokinetics.No information was found for TCPPor TCIP.



### B.Acute (short-term)effects. No information was found for TCPP.An LD5O of56 mg/kg, administered intravenously in mice, was found for TCIP(U.S. Armydata, cited in Ref. 13, RTECS, 1988). The reliability ofthis information cannot be assessed since experimental details are not available.

Stauffer (cited inRef. 20, USEPA, 1981) reported studies on the neurotoxic potential ofTDCP, a structurally similar phosphate, on adult hens. At 10 g/kg,the maximum tolerated dose, there was 7 percent inhibition ofbrain neurotoxic esterase. In positive controls, treated with tri-o-cresyl phospate at 0.5 g/kg, there was an 85percent inhibition.

No subchronic effects data were found for TCIP.The neurotoxic potential ofTCPP in adult white Leghorn hens

was evaluated by Sprague et al. (Ref. 17, 1981). A group of 18hens received an initial oral dose of13.23 gTCPP/kg, followedby the same treatment 3weeks 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 forTCPP or TCIP.

D. Oncogenicity. No information was found forTCPP orTCIP.A structurally similar compound, TDCP, was tested for oncogenicity in rats ofboth sexes and -produced a significantly increased incidence ofhepatocellular carcinoma and interstitial cell tumors ofthe testes (Ref. 19, Stauffer, 1981).

E. Chronic(long-term)effects.No information was found forTCPP or TCIP.



### F.Reproductiveanddevelopmental effects. No information was found for TCPP orTCIP.

G. Observationsinhumans.No information was found forTCPP or TCIP. 

### H.Rationale forhealtheffects 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 ofthe latter two compounds as flame retardants will eventually lead to the release ofTCPP 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 forTCIP inmice 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 of90 days.

In view ofthe lack ofhealth effects information on TCIP and TCPP and given the acute effects, oncogenicity and neurotoxicity ofTDCP, it is recommended thatTCIPand TCPPbe tested for acute effects, including cholinesterase inhibition, 90-day subchronic effects and reproductive effects. Based on theresults ofthe recommended studies, the need for longterm studies should be considered.
IV. Ecological Effects ofConcern

A.Acute andsubchronic(short-term) effects. No information was found for TCPP orTCIP.

The 96-hr LC5O forTDCP was reported to be 3.6mg/L with killifish and 5.1 

### mg/L with goldfish (Ref. 14, Saaski et al., 1981). These authors also reported spine deformations (causedby convulsive muscle contractions) in killifish after24 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 24hours,

C. Otherecologicaleffects. 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 of47 to 107 with killifish and 3to 5 with goldfish.In continuous-flow studies, the bioconcentration factor forTDCP was 31 to 59 forup 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 halfgone in 1.7 hours.

E. Rationale forecologicaleffects 

### recommendations. The widespread

occurrence ofTDCPin environmental samples and the likely contamination of the environment by TCPPand TCIP raise concerns for their ecological effects. Each should be tested for acute toxicity to fish, aquatic invertebrates and algae to better evaluate thehazard associated with chronic exposures to low environmental concentrations. The observation ofspine deformations in fish exposed to TDCP and the widespread occurrence ofTDCP at low concentrations also raises concerns for chronic effects. It is recommended that each ofthese 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." TaikiOsenGakkaishi.20:407-415(1985).

(2)Hollifield, H.C. "Rapid nephelometric estimate ofwater solubility ofhighly insoluble organic chemicals ofenvironmental interests," Bulletinof Environmental Contamination andToxicology.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 oforganic phosphate esters in factory effluent and domestic effluent." SuishitsuOdakoKenkyu. 8:529-535 (1985a).

(5) Ishikawa, S.,Shigezumi, K.. Yasuda, K., and Shigemori, N."Behavior oforganic phosphate esters inseveral waste water treatment processes." SuishitsuOdaka Kenkyu.8:799-807 (1985b), (6) Kenmochi, U., Matsunaga, K. and Ishida, R. "The effects ofenvironmental pollutants on biological systems. 6. organic phosphates in environments." Okoyomo-ken Konkyo HokenSentaNenpo.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 usingmacroreticular resin." Journal of

AssociationofOfficial AnalyticalChemists.64:991-998 (1981).

(8)LaBel, G.L., and Williams, D.T. "Determination oforganic phosphate triesters inhuman adipose tissue."Journal of AssociationofOfficialAnalyticalChemists. 66:691-699 (1983).

(9)LeBel, G.L., Williams, D.T., and Benoit, F.M. "Use oflarge-volume resin cartridges for the determination oforganic contaminants in drinking water derived from the Great Lakes." Advances in ChemistrySeries. 214:309-325 (1987).

(10) Millington, D.C., Bertino,D.J., Kamei, T., and Christman, R.F. "Analysis oforganic compounds adsorbed on granular activated carbon filters used in treatment plants." WaterChlorination, Environmental Impact and HealthEffects.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 Handbookof EnvironmentalChemistry.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 studiesof phosphate esters." AmericanIndustrial HygieneAssociation Journal. 18:633-639 (1978). (13) RTECS. "Registry ofToxic 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 andToxicology.27:775-782 (1981).

(15) Sasaki, K., Suzuki, T., Takeda, M., and Uchiyama, M. "Bioconcentration and excretion ofphosphoric acid triesters by killifish (Oryzeaslatipes)."Bulletinof EnvironmentalContamination and Toxicology,28:752-759 (1982).

(16) Sellstroem, U., and Jansson, B."Mass spectrometric determination oftris(1,3- dichloro-2-propyl)phosphate (TDCP) using NCl-technique." International Journal of Environmental AnalyticalChemistry.29:277- 287 (1987).

(17) Sprague, G.L., Sandvik. L.L, BrookinsHendricks. M.J. and Bickford, A.A. "Neurotoxicity oftwo organophosphorous ester flameretardants in hens." Journal of Toxicologyand 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 ofa two-year oral toxicity/carcinogenicity study ofFyrol 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 ofPesticides and Toxic Substances, U.S. Environmental Protection Agency (August 31, 1981).

(21) Williams, D.T., and Label, G.L. "A national survey oftri(haloalkyl)-, trialkyl-, and triarylphosphates inCanadian drinking water." Bulletinof Environmental Contamination andToxicology.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 ofmutagenic potential and organic contaminants ofGreat Lakes (Canada, USA) drinking water." Chemosphere.11-283-276 (1982).

2.3.c Tetrakis(2-chloroethyl)ethylene 

### diphosphate-Summary of recommendedstudies.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. Healtheffects. 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 2 

## CH 2

## O-P-OCH 2

## CH2

## O-P-OCHCH 2

## Cl 

# 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 InWater (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 forRecommendations

LExposure 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. TCEEPis 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 ofTCEEP.

B. Environmental release.It is likely thatmost ofthe TCEEPproduction is eventually released to the environment

as furniture, automobiles, construction materials, etc. are scrapped and disposed ofin dumps and landfills. Some TCEEPmay be released during thermal decomposition (in accidental fires and incinerators) but no information was found on thermal decomposition.

C. Evidence forenvironmental
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 ofenvironmental 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, iftrue, 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 of1.81 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. Ifthis 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 ofenvironmental media at low concentrations. There is a need for monitoring studies that look for TCEEP to determine ifit 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 TCEEPand to evaluate its biodegradability in natural waters.

III.Biological Effects ofConcern to Human Health

The Committee, at the conclusion of its Sixth Scoring Exercise, concluded that it would not review TCEEPfor health effects (52FR 10409, April 1, 1987). Therefore, no health effects studies are being recommended at this time. W. Ecological Effects ofConcern
A. Acute and subchronic (short-term) effects. No information was found.

B. Chronic(long-term)effects. No information was found.

C. Otherecological effects. No information was found.

D. Bioconcentration and food-chain transport. No information was found. E. Rationale forecological effects recommendations.It is likely that TCEEPhas 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 ofTCEEPto fish, aquatic invertebrates and algae.
References

(1)CHEMEST. "Aprogram for chemical property estimation [data base]." Washington, DC: U.S. Environmental Protection Agency, Office ofPesticides and Toxic Substances (1987).

(2)CLOGP. "Aprogram for the estimation ofoctanol/water partition coefficients [data base]." Washington, DC:U.S. Environmental Protection Agency, Office ofPesticides 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 byN.J. Barone of Olin Corporation (May 26,1987).

2.4 Chemicalsrecommendedwithoutbeing designated forresponsewithin12months-- 2.4.a Butyroldehyde-Summaryof recommended studies.It is recommended that butyraldehyde be tested for the following:

1. Chemicalfate. Monitoring in the vicinity ofmajor manufacturing and use sites.

2.Healtheffects.In depth toxicology evaluation ifwarranted 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 3 

## CHCH 2

## CHO

Empirical Formula

............................................................ C -O. Molecular Weight

................................................................ 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- (cal Vapor Density InAir (air=1)

............ 2.5 (Ref. 14, E DescriDIlon of Chemicals

.................. .... .. Cooaless liquidWindholz, 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 forRecommendations
1.

Exposure Information
A. Production/use/release to environment Butyraldehyde is produced and used in the U.S. at a rate in excess ofone billion pounds per year. SRI reported U.S. production of butyraldehyde in 1987 at 1.835billion pounds by five manufacturers at six sites spread across Texas (Ref.52, SRI International, 1987). Greater than90 percent of the production isused as a chemical intermediate to synthesize nbutanol and 2-ethylhexanol. Domestic production ofn-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 forsurface coatings and its combination with polyvinyl alcohol to form a resin inlaminated safety glass (Ref.8, CEH, 1985).

Butyraldehyde occurs naturally in many plants, includingfruits 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 ofbutyraldehyde
to the environment will occurat 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 itsTexas plant ofabout 831,000 pounds with 90 percent ofthe emissions listed as fugitive emissions to air.Toxic chemical release inventory reporting forms submitted to theEPA in response to the Toxic Chemical Release Reporting rule (53FR 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 forhumanand environmentalexposure.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 tobutyraldehyde 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 ofGovernmental Industrial Hygienists or the Occupational Safety and Health Administration.

One company (Ref.14, Eastman, 1988) reported that the major points ofworker 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 ofn-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 ofproduction 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 ofthe 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 ofits 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 ofmonitoring data.

There are no monitoring data available showing general population
exposure to n-butyraldehyde. Exposures
may be significant forpopulations living

near major manufacturing sites since bvnonwms

............................................ .. 

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### 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 ofbutyraldehyde at the plant exceeded 106,000 pounds per year. Details ofthe sampling and other procedures used to determine this number were not reported.

Butyraldehyde was detected but not quantified in the respired air ofa heterogenous nonsmoking control population living in'Chicago and the surrounding suburbs; however,it was not detected in the respired air oftwo 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 ofthe 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 ofbutyraldehyde in the emissions from internal combustion engines and the involvement ofbutyraldehyde in smog formation. Grosjean et al. have conducted several ofthese 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 ofnorthern Russia. Little orno monitoring data were found

on the presence of butyraldehyde in the air near major manufacturing and use sites although toxicrelease information reveals substantial fugitive emissions at manufacturing and use sites.

Some monitoring studies have looked for butyraldehyde in surface, ground and drinking waters and ithas 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 findingbutyraldehyde 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 ofabout 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 forchemical 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 ofbutyraldehyde 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 thatrepresent

a balance between rates ofrelease and rates ofremoval by degradation
processes. It .isrecommended that monitoring studies be conducted to determine butyraldehyde concentrations in air and water in the vicinity ofthe 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 ofConcernto HumanHealth

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 ofwhich 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 of0.1
to 1 mM inhibits multiplication ofmouse

sarcoma cells in culture (Ref. 46, Pilotti
et al., 1975; Ref. 13, Curvall et al., 1984), and inhibits chemotaxis and reduces viability ofhuman polymorphonuclear leukocytes at 90 mM (Ref. 3, Bridges et al., 1977). Other in vitroeffects incliuded:, damage to the cell membranes ofhuman fibroblasts at 25mM (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 20mM (Ref.20, Giudicelli et al., 1973).

B. Acute andsubchronic(short-term) effects. The acute toxicity data for butyraldehyde are summarized in the following Table 3.

TABLE 3.-TOXICITY OF BUTYRALDEHYDE INLABORATORY 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 inmales oftwo



### mouse strains was defined by a 50 percent reduction in respiratory rate (RD50) following exposure of3or4 mice per dose (dose range not specified] for 10 minutes (Ref.53, Steinhagen and Barrow, 1984). An RD50 of1,532 ppm (4,518 mg/m3) was determined for 

### B6C3F 1 

### mice, and an RD50 of1,015ppm (2,993 mg/M) was determined for Swiss-Webster mice. An RD50 of5,572 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 ofthe 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 ofrats 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 ofbutyraldehyde
to rats at dose levels of0.075, 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 ofthese lesions was dose-related and affected 100 percent of the males and 90 percent offemales 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 ofthe 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 orno potential to produce dermal sensitization in guinea pigs (Ref. 26, Hoechst-Celanese, 1981). After a 3-week induction period consisting ofnine 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 of20 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 of59 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 30ug/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 ofchromosomes 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 ofDrosophilamelanogaster 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 forexposure 

### (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 ofn-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.Reproducitveanddevelopmental effects. A single intraperitoneal injection ofI 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 ofmale 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 ofbutyraldehyde 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 ofspermatozoa without

acrosomes in the vas deferens.

G. Observationsin humans.Among 12 individuals ofOriental 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 forhealtheffects recommendations. Annual domestic production ofn-butyraldehyde is about 1.8 billion pounds by five manufacturers
at six sitesin 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 ofmanufacturing and use sites.

Structural analogues ofnbutyraldehyde including formaldehyde and acetaldehyde have shown carcinogenic effects in animals. IARC considers that there is sufficient evidence from animal studies forthe carcinogenicity offormaldehyde and acetaldehyde whereas the evidence in humans is limited orinadequate, 

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

respectively. TheNational Toxicology indicating impaired spermatogenesis in should be conducted ifwarranted 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 ofn/butyraldehyde developmental effects ofbutyraldehyde effects. Acute toxicity (LC50)values itself.The Committee notedthe data have been reported as shown below. Organism Endpoint Cocy(sl) Reference

Fathead minnow

...................................................................................................................... 96-hr LCS0 25.8 Ref. 12, Curtis and Ward, 1981. Golden Orfe

............................................................................................................................. 96-hr LC50 57 &114 Ref. 32, Juhnke and Ludemann, 1978. Aedes aegyp a larva

.................................................................................................................. 4-hr LC50 2,000 Ref. 33, Kramer et al., 1983.

B. Chronic(long-term)effects. No information was found.

C. Otherecologicaleffects. In a series ofarticles, Bringmann and Kuhn reported on minimum inhibitory concentrations for a large number of chemicals and a variety of aquatic organisms. The definition ofminimum inhibitory concentration varied according to the organism being tested. For daphnids it was described as the maximum tested concentration at which all ofthe 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 5percent 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 ofcell multiplication after 24hours exposure,

as determined by turbidity
measurements oftest 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 aeruginosaalgae

......... 19 Scenedesmusguadicauda algae.. 83 Entosohonsulcatumprotozoa 4.2 Urunerna parduczi protozoa

........... 98 Chilomonasparamaecium proto-

zoa

.......................................... 44 Daphniamagna

................................. 100 Pseudomonaspu&(da bacterium......

. 100

The butyraldehyde concentrations that inhibited the swimming capability of50 percent and 100 percent of Dcphniomagnapopulations 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 ofbacteria as an indication oftoxicity tofish, Curtis et al (Ref. 12,1981) reported a 5-minute EC50 of 16.4 mg/L forPhotobacterium phosphoreumexposed to butyraldehyde. D.Bioconcentration and food-chain transport. An examination offish in Japan revealed the presence of butyraldehyde at low concentrations (Ref. 29, Ito et al., 1980]. The significance ofthis information in unclear since butyraldehyde is produced naturally and is found in many food products. Based on itshigh water solubility and low octanol/water partitioning coefficient, butyraldehyde is not expected to bioconcentrate.

E.Rationale forecologicaleffects recommendations. Butyraldehyde is produced in very large annual quantities at several locations in Texas.There are reports ofsubstantial emissions of butyraldehyde toair atmanufacturing and use sites. There may be significant concentrations ofbutyraldehyde 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 ofbutyraldehyde 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 ofbiota if warranted by monitoring data.
References

(1)Babiuk, C., Steinhagen, W.H., and 

### Barow, C.S. "Sensory irritation response to inhaled aldehydes afterformaldehyde pretreatment." Toxicology and Applied Pharmacology. 79:143-149 (1985). (2)Brabec, M.J. "Aldehydes and acetals." in G.D. Clayton and F.E. Clayton (Eds.): 

### Patty's Industrial Hygienceand Toxicology. Volume 2A. Third Revised Edition. New York, NY: John Wiley and Sons. pp. 2629- 2069 (1981).

(3)Bridges, R.B., Kraal, J.H., Huang, L.J.T., and Chancellor, M.B. "Effects ofcigarette smoke on in vitro chemotaxis ofhuman polymorphonuclear leukocytes." Infection and Immunity. 16:240-248 (1977). (4) Bringmann, G., "Determination ofthe biological toxicity ofwaterbased substances towards protozoa. 1. Bacteriovorous flagellates (model organism: Entosiphon sulcatumStein." Z. WasserundAbwasser Forschung. 11:210-215 (1978). (5)Bringmann, G., and Kuhn, R., "Comparison ofthe toxicity thresholds of water pollutants to bacteria, algae and protozoa inthe cell multiplications inhibition test." Water Research. 14:231-241 (1980). (6) Bringmann, G., and Kuhn, R. "Comparison ofthe effect ofharmful substances on flagellates and ciliattes aswell

as on bacteriovorous and saprozoic protozoans." GWF,Gas-Wasserfoch: Wasser/Abwasser.122:308-313 (1981).

(7)

Bringmann, G., and Kuhn, R. "Results of toxic action ofwater pollutants on Daphnia
magna Straus tested by an improved standardized procedure." Z. Wasserund AbwosserForschung. 15:1-6 (1982). (8) CEH. ChemicalEconomicsHandbook. Menlo Park, CA: SRI International. Section 682.7000D (1985).

(9) C&EN. "Production by the U.S. Chemical Industry." Chemical and Engineering News. 6640 (1988). (10) Chou, W.L Speece, R.E., Siddiqi, R.H., and McKeon, K."The effect ofpetrochemical structure on methane fermentation toxicity." Progress in Water Technology.10:545-558 (1978).

(11.) Corwin, J.F. "Volatile oxygencontaining organic compounds in sea water: Determination." Bulletinof MarineSciences. 19:504-509 (1989)..

(12) Curtis, M.W., and Ward, C.H. "Aquatic toxicity offorty industrial chemicals: Testing in support ofhazardous substance spill prevention regulation." Hydrology.51:359-367 (1981).

(13) Curvall, M., Enzell, C.R., and Pettersson. B."An evaluation ofthe utility of four in vitro short-term tests for predicting the cytotoxicity of individual compounds derived from tobacco smoke." CellBiology andToxicology.1:173-193 (1984).

(14) Eastman. Letter ofJuly 20, 1988 from R.D. Gerwe, Technical Associate, Eastman Kodak Co., Kingsport, TN., to R.H. Brink, Executive Secretary. TSCA Interagency Testing Committee.

(15) ENVIROFATE. Environmental Fate [data base]. Baltimore, MD: Chemical Information Systems, Inc. (1988).

(16) Ewing, B.B., Chian, E.S.K., Cook, J.C., Evans, C.A., Hopke, P.K., and Perkins, E.G. "Monitoring to detect previously unrecognized pollutants in surface waters.

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

Appendix: Organic analysis data." Washington, DC: U.S. Environmental Protection Agency EPA-560/6-77-015 75 pp. (1977).

(17) Fung, R., Swanson, R.D., and Grosjean, D. "Measurements ofaldehydes in ambient air." Proceeding ofthe 74thAnnualMeeting oftheAirPollutionControl Association. Philadelphia, PA. Paper 81-47.1, 14 pp.(1981).

(18) Gage, I.C. "The subacute inhalation toxicity of 109 industrial chemicals." British Journalof Industrial Medicine.27:1-18 (1970). (19) Galloway, S.M., Armstrong, M.J., Reuben, C., Colman, S., Brown, B., Cannon, C., Bloom, AD. Nakamura, F.. Ahmed, M., Duk, S., Rimpo, J., Margolin, B.H., Resnik, M.A., Anderson, B., and Zeiger, E. "Chromosome aberrations and sister chromatid exchanges in Chinese hamster
ovary cells: evaluation of 108 chemicals." Environmental and Molecular Mutagenisis. 10: (Supplement 10) 1-175 (1987).

(20)Giudicelli, Y., Nordmann, R., and Nordmann, J. "Action ofaldehydes on lipolysis and glucose metabolism inrat adipose tissue." Life Sciences.12:35-47 (1973).

(21) Grosjean. D. "Formaldehyde and other carbonyls in Los Angeles ambient air." EnvironmentalScienceand Technology. 16:254-262 (1982).

(22) Grosjean,D.. Swanson, R.D., and Ellis, C. "Carbonyls in Los Angeles air contribution ofdirect emissions and photochemistry." The Scienceofthe Total Environment.29:65-85 (1983).

(23) Grosjean, D., and Wright, B. "Carbonyls in urban fog, ice fog, cloudwater and rainwater," AtmosphericEnvironment. 17:2093-2096 (1983).

(24) Grosjean, D., and Fung, K. "Hydrocarbons and carbonyls in Los Angeles air." Journal of

AirPollutionControl 4ssociation. 34:537-543 (1984). (25) Hawley. Hawley's Condensed ChemicalDictionary.11th ed. Revised by Sax, N.I., and Lewis, R.J. ads. New York,NY: Van Nostrand Reinhold Company, p. 193 (1987).

(26) Hoechst-Celanese. Letter of June 21, 1988 with attachments from C.J. Schaefer, Manager, Product Safety, Hoechst-Celanese Co., Dallas,TX, to Roberta Wedge, Staff Scientist, Dynamac Corporation. Re: TSCA Interagency Testing Committee Information Request on n-Butyraldehyde.

(27) IARC. International Agency for Research on Cancer.IARCMonographson theEvaluationofCarcinogenic Risks to Humans.Lyon, France: World Health Organization. Supplement 7: p. 77, 211 (1987).

(28) Isidorov, V.A., Zenkevich, I.G., and loffe.B.V. "Volatile organic compounds in the atmosphere offorests." Atmospheric Environment.19:1-8 (1985).

(29) Ito, K., Nakayama, S., and Ishihuro, T., "Evaluation ofGC-MS analysis for the identification of chemical substances infish." NipponKankyo EiseiSentaShoho.7:91-98 (1980).

(30) Jones, G.L, and Teng, Y.S. "A chemical and enzymological account ofthe multiple forms ofhuman liver aldehyde dehydrogenase. Implications for ethnic differences in alcohol metabolism." BiochimicaetBiophsicoActa 745:162-174 (1983).

(31) Jonsson, A., Persson, K.A., and Grigoriadis, V. "Measurements of some low molecular-weight oxygenated, aromatic, and chlorinated hydrocarbons in ambient airand in vehicle emissions." Environment International. 11:383-392 (1985). (32)Juhnke, L,and Ludemann, D. "Results ofstudies on the acute toxicity to fish of200 chemical compounds with the golden orfe test." Z. Wasser undAbwasserForschung. 11:161-164 (1978).

(33) Kramer, V.C., Schnell, D.J., and Nickerson, K.W. "Relative toxicity oforganic solvents toAedes aegyptilarvae." Journalof InvertebratePathology. 42:285-287 (1983). (34) Krotoszynski, B.K., and O'Neill, H.J. "Involuntary bioaccumulation of environmental pollutants in nonsmoking heterogeneous human population." Journal of Environmental Scienceand Health.A17:855- 883 (1982).

(35) Mortelmans, K., Haworth, S., Lawlor, T., Speck, W., Tater,R., and Zeiger,E. "Salmonella mutagenicity tests: II.Results from the testing of270chemicals." Environmental Mutagenesis.8(Supplement 7): 1-119 

### (1988).

(36) Moutschen-Dahmen J.,MoutschenDahmen. M., Degrave, N., Houbrechts, N., and Colizzi, A. "Genetical hazards ofaldehydes from mouse experiments." Mutation Research.29:205 (1975).

(37) Moutschen-Dahmen 

### J., MoutschenDahmen, M., Houbrechts, N., Colizzi, A. "Cytotoxicity and mutagenicity oftwo aldehydes: crotonaldehyde and butyraldehyde in the mouse." Bulletinde la SocieteRoyaledes SciencesdeLiege.45:58- 72 (1976).

(38) NIOSH. "National Occupational Hazard Survey (1972-1974)" [data base]. Cincinnati, OH: Department ofHealth and Human Services, National Institute for Occupational Safety and Health (1976).

(39) NIOSH. "National Occupational Exposure Survey (1980-1983)" (database]. Cincinnati, OH: Department ofHealth and Human Services, National Institutes for Occupational Safety and Health (1984).

(40)NTP.National Toxicology Program. Personal communication from Dr.

### J.French, NIEHS, NC to S.Diwan, Dynamac on April 20.1988.

(41) NTP.National Toxicology Program. Personal communication from Dr. 

### J. French, NIEHS, NC to R. Platz,Dynamac Corporation

on October 14,1988.

(42) Obe, G., and Beak, B."Mutagenic activity ofaldehydes." Drugand Alcohol Dependence. 4:91-94 (1979). (43) Ogawa, L,and Fritz, J.S. "Determination oflow concentrations oflowmolecular-weight aldehyde and ketones in aqueous samples."Journal of Chromatography. 329:81-89 (1985). (44) Opdyke, D.LJ. "Monographs on fragrance raw materials, n-Butyraldehyde." FoodCosmeticsandToxicology.17 (Supplement): 731-734 (1979).

(45) Pellizzari, E.D., Hartwell, T.D., Harris, B.S., Waddell, R.D., Whitaker, D.A., and Erickson, M.D. "Purgeable organic compounds in mother's milk." Bulletinof Environmental Contamination and

- Toxicology.28:322-328 (1982).

(46)Pilotti, A., Ancher, K., Arrhenius,E.,
and Enzell, C. "Effects oftobacco and tobacco smoke constituents on cell multiplication invitro." Toxicology.5:49-62 (1975). (47) Poli, G., Biasi, F.,Chiarpotto, E., Carini, R., Cecchini, G., Ramenghi, U.,and Dianzani, M.U. "Pro-hemolytic effect ofaldehydic products oflipid peroxidation." FreeRadical ResearchCommunications.3:279-284 (1987).

(48) RTECS. "Registry oftoxic effects of chemical substances" [data base]. Cincinnati, OH: National Institute for Occupational Safety and Health (1987).

(491 Sim,V.M., and Pattle, R.E. "Effects of possible smog irritants on human subjects." JournaloftheAmericanMedical Association.165:1908-1913 (1957).

(50) Skog, E. "Atoxicological investigation oflower aliphatic aldehydes. I.Toxicity of formaldehyde, acetaldehyde, propionaldehyde and butyraldehyde; as well

as acrolein and crotonaldehyde." Acta Pharmacologica. 6:299-318 (1950). (51) Smyth, Jr. H.F., Carpenter, D.P., and Weil,C.S. "Range-finding toxicity data: List IV." AMA Archives of Industrial Hygiene andOccupational Medicine.4:119-122 (1951). (52) SRI International. "Directory of chemical producers, United States, 1987." Menlo Park, CA:SRI International, p. 508-509 (1987).

(53) Steinhagen, W.H., andBarrow, C.S. "Sensory irritation structure-activity study of inhaled aldehydes in B6C3Ft and SwissWebster mice." Toxicologyand Applied Pharmacology. 72:495-503 (1984). (54) Thelestam, M., Curvall, M.,and Enzell, C.R. "Effects oftobacco smoke compounds on the plasma membrane of cultured human lung fibroblasts." Toxicology. 15:203-217 (1980).

(55) USEPA. Memorandum and copies of Form R submissions from Shirley Leacraft, Information Management Division, Office of Toxic Substances, U.S.Environmental Protection Agency, to Robert Brink, TSCA Interagency Testing Committee (October 4, 1988).

(56) USITC.U.S. International Trade Commission. "Synthetic organic chemicals, United States production and sales, 1982." Publication No. 1422. Washington, DC:U.S. International Trade Commission p. 259,282 (1983).

(57) Valencia, R., Mason, J.M., Woodruff, R.C., and Zimmering, S. "Chemical mutagenesis testing in Drosophila. IIl. Results of48 coded compounds tested for the National Toxicology Program." Environmental Mutagenesis.7:325-348 (1985). (58)Viar. "Statistical Data Base." Alexandria. VA: Viar and Company/U.S. Environmental Protection Agency (1986).

(59) Weiner, H. "Aldehydes Oxidizing Enzymes." In:EnzymaticBasisof Detaxication. Vol. 1,New York, NY: Academic Press,Inc., pp. 261-280 (1980).

(60) Wilkin, J.K., and Fortner, G. "Cutaneous vascular sensitivity to lower aliphatic alcohols and aldehydes in orientals." Alcoholism: Clinical and Experimental Research.9:522-525 (1985). (81) Windholz, M. TheMerckIndex.10th ed. Rahway,NJ: Merck &Co., Inc., p. 220 (1983).

(62) Zlatakis, A., Poole,C.F., and Brazeli,R. "Volatile and metabolites in sera ofnormal and diabetic patients." Journal of Chromatography. 182:137-145 (1980).
IFR Doc. 88-26300 Filed 11-15-88; 8:45am]

BILLING CODE 600-50-M 

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