618 Federal Register I VoL 54, No. 5 / Monday, January 9, 198t / Rules and Regulations

4OCFR Part 799 I. ITC Recommendation Testing under this negotiated testjr.~ In its Initial Report to EPA, published agreement (NTA) was suspended ~ [OPTS-42092A FRL-3503-7J in the Federal Register of October 4~ in August 1984, a suit brought against EPA by the Natural Resources Defe~ 1977 (42 FR 55028), the ITC Testing Consent Order on Atkyf Council (NRDC) resulted in the ru~ir.g Phtha(ates recommended that the alkyl chemical category be considered for that such negotiated testing prog~.~ were riot legal substitutes for a te5t rcle AOENCY~Environmental Protection environmental effects testing.. under section 4 of the ToxicSubsta~~ Agency IEPA). The recommended environmental Control Act (TSCA) [A’RDC cjpd ~ effects testing included chronic and ACT1ON Final rule. CXC) v. EPA,. 595 F Supp. 1255 (S.D~y reproductive effects testing with aquatic 1984)j, Furthermore, BBP wa~ SUMMARY: This document announces organisms, especially fish. EPA’s health specifically mandated for rulern~j~~ that EPA has signed an enforceable effects testing concerns for these for notice explaining why testing wa~ testing Consent Order with Aristech chemicals are being examined not necessary. As a result, the Ageacy Chemical Corporation (Aristech), BASF separately and are not addressed in this published a proposed rulefor BBP Corporation (BASF). Exxon Chemical notice. requiring environmental effectsand Company (Exxon), Eastman Kodak EPA responded to the ITCs chemical fate testing (50FR 3844e Company (Kodak), and Witco designation of the alkyl phthalates September 8, 1985). The proposed test~ Corporation, Humko Chemical Division category by issuing a notice in the for BBP was completed and submitte~i~ (Witco). These companies have agreed Federal Register (October 30, 1981; 46 FR EPA by Monsanto Company, andthe to perform certain chemical fate and 53775) announcing that it had decided Agency has issued a Federal Regists~ environmental effects tests on dimethyl not to require testing. EPA instead notice withdrawing the proposed rule accepted a testing program sponsored (DMP CAS No. 131—11—31, di- (52 FR 41593; 29 October, 1987). n-butyl phthalate (DnBP~CAS No. 84— by the Phthalate Eaters Program Panel Forthe remaining phthalate esters (PEPP) of the Chemical Manufacturers 74—2), dthexyl phthalate, (DHP~CAS No. recommended by the ITC, several of the Association (CMAJ. The program 68515—50-4 and 84—75—3), di—2— Phase II tests noted in the NTA are itili included testing for both health and needed; namely, earlylife stage testing ethyihexyl phthalate (DEFIP CAS No. environmental effects; however, in 117—81—7), di-(heptyl, nonyl, undecyl) with fish and sediment transport keeping with the subject of this notice, (adsorption). EPA, in this final rule, phthalate (D711P CAS No.88515-42—4), discussion will focus on the diisodecy) phthalate (DIDP CAS No. announces that these environmentaj and environmental effects portion. chemical fate testing needs are being 66515—49-1 and 26761-40-0), diundecyl CMA proposed phased testing for phthalate (DUP GAS No. 3648—20—2), addressed by consent order, Health environmentaleffects for 13 alkyl and ditridecylphthalate (DTDP~CAS effects testing for this chemical cate~ry phthalates identified as being annuafly will be the subject of a future notics~ No. 68515-47-9 and 119-06-2). These produced in quantities greaterthan ten chemicals are added to the list of testing million pounds, and for benzyl butyl IL Testing Consent OrderNegotiations Consent Orders in 40 CFR 799.5000 for phthalate (BBP}. CMA’s proposal In the Federal Register of December which the export notification included testing for aquatic toxicity; requirements of 40 CFR Part 707 apply. 24. 1986 (51 FR 46718), and in environmental transport and fate, and accordance with the procedures Depending on theresult.s of these biodegradation of the alkyl phthalates established In 40 CFR 790.28, EPA tests, two additional chemical and 881’. These were the environmental requested persons interested in substances, diethyl phthalate (DEP GAS testing areas of concern to the Agency participating in or monitoring testing No. 84-66-2) and diisononyl phthalate and to the ITC. negotiations on alkyl phthalates to (DINP GAS No.88515-48-0 and 28553-. The program was designed to contact the Agency. EPA held public 12—0), may also be tested, and if so complete testing in two phases. Phase 1 meetings with interestedparties on would also be made subject to export tests were performed to determine acute January 7, 1987, February 12, 1987, June notification requirements. toxicity to fish, aquatic invertebrates. 3, 1987, and September 29, 1987 to EFFECTIVE DATE: January 9~1989.. and algae, and chronic toxicity to discuss the testing appropriate for the aquatic invertebrates. Biodegradation alkyl phthalate chemicalcategory. On FOR FURTHER INFORMATIONCONTACT tests and tests to determinevapor November 11, 1988, EPA, Aristech. Michael M. Stahl, Acting Director, TSCA pressure, water solubiity and Koctanol/ BASF, Exxon, Kodak, and Witco signed Assistance Office (TS.-799), Office of water were also performed. Phase I of a testing Consent Order for certain alkyt Toxic Substances, Rrn. EB-44, 401 M St.. testing has been completed. All of the phthalate esters. A Consent Orderis ~ SW., Washington, DC 20460, (2021 554— data from these studies have been based on a formal finding and expeditel 1404, TDD (202) 554-0551. placed in the public file on alkyl testing, while retaining the same TSCA SUPPLEMENTARY fNFORMAT1OPC Under phthalates and BBP (OPTS-42005) and penalty provisions applicable under procedures described in 40 CFR Part 790, are available for public inspection. rulemaking. Under the Order, these Aristech, BASF, Exxon, Kodak, and In Phase 11 of the testing, more companies have agreed to conduct or Witco have entered into a testing advanced tests, including early life stage provide for the conduct of fish early iiie Consent Order with EPA in which they testing with fish, bioconcentration tests stage toxicity tests and adsorption have agreed to perform certain chemical with oysters, soil and water isotherm tests. The specific test fate and environmental effects tests for biodegradation tests, and tests of soil standards to be followed and the test;u~ DMP, DnBP, DHP, DEHP, D7I1P, D~DP, transport were to be performed, if the schedule for each test are includedin DUP, and DTDP. This rule amends 40 results of the Phase I tests Indicated a the Order. Procedures for submitting CFR 799.5000 by adding these eight need for further testing. The tests and study plans, modifying the Order, chemical substances to the list of chemicals selected for Phase 11 testing monitoring the testing and other chemical substances and mixtures were to be determined primarily by the provisions are also included in the subject to testing Consent Orders. results of the Phase I tests. Order. Federal Register / Vol. 54, No. 5 / Monday, January 9, 1989 I Rules and Regalations 619 m. u~and Exposure Phase I of the NTA and other available signatory manufacturers have therefore data to estimate the water solubility. agreed in this Consent Order to double The alkyl phthalatea are a chemical volatility and aerobic biodegradability (under the conditions described in the category consisting of alkyl diesters of of the phthalate esters and to test standard applicable to this Consent 1,2-benzenedicarboxylic acid. They sufficiently predict the acute toxicity of Order) the normal length of exposure to typically areformed by esterifying the phthalate esters to fish, the chemical substance in the early life anhydride with various invertebrates and algae and their stage toxicity test. Doing so will akohols. The compounds vary in size, chronic toxicity to aquatic invertebrates. strengthen any potential conclusion of depending on the alcohols used, from However, the Agency believes It has no toxic response for some or all of the the short chain compound dimethyl Insufficient data to predict chronic long-chain compounds. phthalate to long-chain compounds such toxicity of the phthalate esters to fish, as ditridecyl phthalate. Mixed alcohols Depending on the results of the testing and to reliably predict adsorption of of these five compounds, additional. may also be used in the esterification these chemicals to sediments. EPA process giving a combination of phthalate esters may be tested. Diethyl intends that testing be conducted under phthalate (DEP) may also be tested if its unsymmetrical alkyl diester compounds, this Consent Order to fill those data such as D711 phthalate, whose side toxicity cannot be reliably estimated deficiencies. EPA believes that these from the test data on DMP and DriB?. chains may consist of alkyl groups of 7, data will, with the earlier data on the 9, or 11 carbons. Furthermore, if D7IIP produces a toxic alkyl phthalates and BBP, be sufficient reponse. diisononyl phthalate (DINP) Phthalate esters are used as to reliably assess current risks that the in products at may be tested; positive results for DINP dialkyl and alkyl benzyl phthalates may may further lead to testing on diisodecyl different percentages depending on the present to the environment. The testing mutual compatibilities of each and the phthalate (DIDP). If DUP produces a will examine chronic toxicity to fish positive result, ditridecyl phthalate degree of flexibility desired in the (through early life stage toxicity testing (DTDP) may be tested. Testing of these plastic product (Ref. 1). The chain with rainbow trout) and adsorption of additional compounds (DEP, DIN?, lengths affect the properties of the these chemicals to sediments. EPA compounds in a fairly predictible way DIDP, and DTDP) would be indicated in intends to gatherdata by having a follow-up Federal Register noticefor a8 the chain gets longer, water solubility manufacturers test a subset of the 14 and vapor pressure decrease, and K.~ notification purposes, but is considered alkyl phthalates tested under Phase I of part of this Consent Order. increases (Ref~1). the negotiated testing agreement. Many of thealkyl phthalates are EPA and representatives of the EPA will use the data to determine a industry signatories will consult in a produced in large volume, with some quantitative structure-activity individual compounds having annual good faith effort to reach agreement on relationship (QSAR) that It can apply to the interpretation of the data and the production volumes well In excess of untested members of the alkyl phthalate 100 million pounds. The alkyl phthalates necessity of testing these additional ester chemical class. EPA believes, from compounds. Should EPA and the are primarily used as plasticizers ia a available data, that this chemical wide variety of plastic products category Is amenable to a QSAR industry signatories ultimately disagree on the interpretation of the results, then (although a few, such as dietbyl approach. However, if the data phthalate, are used in such products as developed under this Consent Order EPA reserves its right to issue a section 4 test rule to obtain the necessary data. cosmetics), and releases into the indicate such is not the case, then the environment may occur through waste Agency reserves its right to re-examine The process for review of the results is described in more detail in the Consent streams from manufacturing facilities or the testing needs for this chemical from use and disposal ofend products. category. Also, the use of QSAR Order. The 14 phthalate esters selected for estimation does not mean that estimated Adsorption isotherm testing In testing in Phase I of the NTA were values take precedence overvalid sediments shall be first conducted on selected because they have individual experimental data, where the twodiffer. DI-EP, DEHP. DIDP and DTDP (Group I); annual production volumes of Therefore, should manufacturers of and if necessary, also on D711P and approximately 10 million pounde or untested or new phthalate ester DIN? (Group If). The compounds greater. The chemicals selected for compounds wish, they could develop selected for Group I cover a range with additional testing in this Consent Order experimental data, which EPA would respect to the physical/chemical represent a subset of those 14. then consider in any risk estimation or properties expected to affect the regulatory context. sorptive behavior of phthalstes. Testing IV. Testing Program; Chemical Fateand Under the Consent Order, DMP, DnBP, of this group should provide useful Environmental Effects DM1’, D71IP and DUP will all be tested information about the effects of With regard to untested phthalate in the fish early life stage toxicity test in structure and associated properties on esters, EPA believes tKat it can, for risk accordance with the schedulesand test adsorption. Compounds from Group I assessment purposes, reliably predict protocols specified in the Order. These are C-..6 to C—13 linear and branched values for most of the environmental five phthalate eaters are characterized phthalate esters. Their selectionwill effects endpoints and chemical fate by having low, medium, or high numbers complement the existing adsorption processes identified as being of concern of carbons in their alkyl side chains (n isotherm data on DNBP, DNOP, and in the NTA. Bioconcentration potential = I to II). In a more limited way, these DEHP. The inclusion of DEHP in Group I of the phthalate esters can be predicted five compounds also cover an array of will provide an internal standard for the from studies performed on a number of chemicals having an odd or even new set of chemicals to be tested. these compounds with a variety of fish number of carbons in the alkyl side Testing of these chemicals will also and aquatic invertebrates. These data chains and having either branched or provide a small data set for the indicate bioconcentration values of 112 unbranched side chains. Based on development of new, or use of existing to 856 in fish and 116 to about 4,000 in available data, phthalate esters of side structure-activity relationships, to invertebrates (Refs. 2 through 11). chain lengths of more than six carbons attempt to predict the sorptive behavior Furthermore, EPA has sufficient data may not be toxic at the chemical’s limit of the compounds in Group II. Testing based on studies completed during of water solubility. EPA and the for 1)711? and DIN?, if necessary. would 620 Federal Register / Vol. 54, No. 5 / Monday, January 9, 1989 / Rules and Regulations

be indicated in a follow-up notice in the consent agreements (51 FR 23706; June (9) Streufert. J. M.. 5. R. Jones, and H. 0. Federal Register for notification 30, 1986). Sanders. ‘Toxicity and biological effects of purposes. (3) Communications consisting ofi phthalate esters on nudges (Chironornus (a) Written letters. plumosus).” Transactions of the .~vfissouri V. Export Notification (b) Contact reports of telephone Academy of Science 14: 33—40 (1980). The issuance of the Consent Order conversations. (10) Perez, K. T.. E. W. Davey, N. F. Lackie, subjects any person who exports or (c) Meeting summaries. C. E. Morrison, P. G. Murphy, A. & Soper, and D. L Winslow. “Environmental intends to export DMP, DnBP, DEHP, (4) Reports—published and assessment of a phthalate ester, di-(2- D7I1P, DIDP, DTDP and DUP to the unpublished factual materials. ethylhexylJ phthaiate (DEHP), derived from a export notification requirements of B. References marinemicrocosm.” Zn:“Aquatic Toxicology section 12(b) of TSCA. The specific and Hazard Assessment: Sixth Symposium, requirements are listed in 40 CFR Part (1) Hirzy, (. W., W. J. Adams, W. E. ASTM STP 80~”W. E. Bishop. R. El. 707. In the June 30, 1986 (51 FR 23706), Gledhill, and J. P. Mieure. “Phthalate esters: Cardwell, and B. B. Heidoiph, eds. American Interim Rule establishing the Testing The environmental issues.” Seminar Society for Testing and Materials, Consent Order process, EPA added and presented to USEPA National Water Quality Philadelphia, Pennsylvania. pp. 100—191. Laboratory—Duluth. (October 16, 1978). reserved Subpart C of Part 799 for listing (1984). (2) Karara. A. H. and W. L Hayton. (11) Brown, D.. C. Poels, 3. B. Scheubel, and of chemical substances subject to testing “Pharmacokinetic model for the uptake and consent orders issued by EPA. This H. Wellens. “An as8essment of the disposition of di-2-ethythexyl phthalate in occurrence and effects of dialkyl listing serves as notification to persons sheepshead minnow Cyprinodon variegatus” orthophthalates in the environment,” who export or intend to export chemical Aquatic Toxicology 5:181—195 (1984). ECE’FOC Technical Report No. 19. L. Turner, substances or mixtures which are the (3) Mehrle. P. M.. and F. L. Mayer. “1)1-2- ed. European Chemical IndustryEcology and subject of testing consent orders, that 40 ethyihexyl phthalate: residue dynamics and Toxicology Center. Brussels, Belgium, 64 pp. CFR Part 707 applies. biological effectsin rainbow trout and (May 22, 1985). fathead minnows.” Zn;“Trace substances in VI. Rulemaldng Record Environmental Health—X. A Symposium”, EL Confidential Business Information EPA has established a record for this 1). Hemphil. ed. University ofMissouri. (CBI), while part of the record, is not Columbia, Missouri. pp. 519—524. (1978). available for public review. A public rule and the Consent Order (docket (4) Macek. K. J., S. R. Petrocelli, and B. H. number OPTS-42092A). This record version of the record, from which CDI Sleight IlL “Considerations in assessing the has been deleted, is available for contains the basic information potential for, and significance of considered by the Agency in developing biomagnification of chemical residues in inspection in the TSCA Public Docket this rule and the testing Consent Order. aquatic food chains.” In: “Aquatic Office, Rin. NE-G004, 401 M St. SW., This record includes the following Toxicology. ASTM STP 667.” L. I.. Marking Washington, DC, from 8 a.m. to 4p.m., information: and R. A. Kimerle, eds. American Society for Monday through Friday. except legal A. Supporting Documentation Testing and Materials, Philadelphia, holidays. Pennsylvania. pp. 251—268. (1979). (1) Testing Consent Order between List of Subjects in 40 CFR Part 799 Aristech. Exxon, Kodak, BASF, and (5) Gledhill, W. E., R. C. Kaley, W. J. Adams, 0. Hicks, P. R. Michael, and V. W. Witco and the Agency. Saeger. “An environmental safety assessment Test procedures, Environmental (2) Federal Register notices pertaining of butyl benzyl phthalate.” Environmental protection, Hazardous substances, to this notice consisting of: Science and Technololgy 14(3): 301—305 Chemicals, Chemical export. (a) Notice containing the LTC (1980). Recordkeeping and reporting recommendation of alkyl phthalates to (6) Gloss. S. P. and G. R. Biddinger. requirements. the Priority List (October 12, 1977; 42 FR “Comparison of system design and Dated: December 27, 1988. 55026). reproducibility to estimate bioconcentration of di-n-hexylphthalate by Daphnia magna. Susan F. Vogt, (b) Notice containing the ITC Acting Assistant Administratorfor Pesticides recommendation of BBP to thePriority “In: “Aquatic Toxicology and Hazard Assessment” Seventh Symposium, ASTM and Toxic Substances. List (November 25, 1980; 45 FR 78432). STP 854.” R 1). Cardwell, R. Purdy and R. (c) Notice containing the Agency’s Therefore, 40 CFR Part 799 is Comotto. eds. American Society for Testing amended as follows: response to the Interagency Testing and Materials, Philadelphia. Pennsylvania. Committee for thealkyl phthalates and pp. 202—213 (1985). PART 799—4AMENDEOJ (October 30, 1981; (73 Brown. D. and R. S. Thompson 46 FR 53775). “Phthalatesand the aquatic environment: I. The authority citation for Part 799 (d) Notice of proposed rulemaking for Part I of the effect of di-2-ethylhexyl continues to read as follows: BBP (September 6, 1985; 50 FR 36446). phthalate (DEL-lIP) and di-isodecyl phthalate (e) Notice of withdrawal of proposed (DIDP) on the reproduction of Daphnia Authority: 15 U.S.C. 2603, 2611, 2625. rulemaking for BBP (October 29, 1987; 52 magna and observations on their 2, Section 799.5000 is amended by FR 41593). bioconceritration.” Chemosphere 11(4):417— 428 (1982). adding the following chemical (f) Notice soliciting interestedparties (8) Brown, El. and R. S. Thompson. substances in Chemical Abstract for developing a consent order for the “Phthalates and theaquatic environment: Service (CAS) Registry Number order to alkyl phthalates (December 24, 1988; 51 Part II the bioconcentration and depuration of the table, to read as follows: FR 46718). di-2-ethylhexyl phthalate(DEHP) and di- (g) Notice of interim final rule on isodecyl phthalate (D~DP)in mussels (Mytilus § 799.5000 Testing consent o~’ders. procedures for developing enforceable edulis). Chemosphere 11(4): 427—435 (1982). * * . 0 *

GAS Substance or mixture name Tes8ng Fsaiast. REGISTER Number cItaao~

84—74—2 0$-n-buty~ EnvWonmentai effects —..--.- (~~Se~1FR date) Federal Register / Vol. 54, No. 5 / Monday, January 9, 1989 / Rules and ReRulations ij~ — — —_ —

C.&S Substance or mixture name Testing FEDERAL REGISTER t~umDer citation

84-75-3 D~-n-hexyIphthatate...... ~.. .. Enviconmentai effects (Ins~FR date) Chemical fate (Insert FR date)

117—81-7 Di.2-ethylhexyl pbthatate . Chemical fate (Insect FR date) 119-06—2 Ditricecyl ~ . - ~ Chemical fate __-.. (fr~ffFR dale) 131-11-3 Dimethly phthatate — .. ~ Environmental effects ~..... (Insert FR date)

3648-20-2 Diundecyl phthafate . ~ . .~ Environmental etfects,...... -.. (Insert FR date) 26761-40-0 Dwsodecyi phtliaJate ....~ .~... _._... Chemical fate .._._. (trisect FR data) 68515-42-4 0 (heotyl, nonyl, undecyl ptittialate (mised isomers) ~. ... Environmental effects (Insert FR date) 68515-47-9 Ditridecyl phthalate )m~sedisomers) - .... Chemical fate (Insert FR date) 68515—49-1 Ditsooecyi pfltriaate (mixed isomers) - Chemical fate (tnsert FR date) 685’ 5-50-4 Dihexyl pflthalate (mixed isomers) .. - ...... ~ ..._. Envsonmental effects (Insert FR date) Chemical fate __~__ _. (Insert FR date)

[FR Doc. 89-299 Filed 1—6--89~8.45 am) BILUNG CODE 6560—5O-M