31804 Federal Register I Vol. 53, No. 161 I Friday, August 19, 1988 / Rules andRegulations

ENVIRONP~ENTALPROTECTIONAGENCY

40 CFR Part 799

[OPTS—42054B; FRL-3431-9l

Testing Consent Orders on Aniline andSeven Subatituted Anilines

AGENCY: EnvironmentalProtectionAgency)EPA).ACTION: Final rule.

SUMMARY: This documentannouncesthat EPA hassignedenforceabletestingconsentorders both with manufacturers(including importers)who haveagreedto performcertainhealthandenvironmentaleffects test5 on anilineandwith manufacturerswho haveagreedto performcertain healthand/orenvironmentaleffectstests on sevensubstitutedanilinesthattheymanufacture.Thesechemicalsubstancesweredesignatedby theInteragencyTestingCommittee(ITC) forpriority testing.Elsewherein this issueof the FederalRegister,the Agencyannouncesits decisionto terminaterulemakingfor certainother categorymembersfor healthandenvironmentaleffectsandchemicalfate.EFFECTIVE OATE Effective on August19,1988.FOR FURTHER INFORMATION CONTACT:Michael M. Stahl.Acting Director, TSCAAssistanceOffice (TS—799),Office ofToxic Substances,Room EB—44. 401 MStreet.SW., Washington.DC., (202) 554—1404.TIJD: (202) 554—0551.SUPPLEMENTARY INFORMAT1O4: This ruleaddsaniline (CAS No. 62.-53—3). 2-chloroaniline(CAS No. 95—51—2), 4-chloroaniline(C.AS No. 106—47—8), 3,4-dichloroaniline(CASNo. 95—78.-I). Z-nitroaniline (CASNo. 88—74—4),4-nitroaniline (CASNo. 100—01—06),2,4-dinitroaniline (CAS No. 97—02—9), and2.6-dichloro-4--nitroaniline(CAS Ni.. 99-.30—9) to thelist of chemicalsubstancesandmixtures(“chemicals”)subjecttotesting consentordersin 40 CFR799.5000.

I. ITC Recommendation

In its FourthReportto EPA, publishedin the FederalRegisterof June1. 1979 (44FR 31866),theITC recommendedthatall

chemicalsin the categorydefinedas“aniline andanilinessubstitutedin oneor morepositions with achloro. bromo.or nitro group.or anycombinationofoneor moreof thesesubstituentgroups”beconsideredfor healtheffects.chemicalfateandenvironmentaleffectstesting.TheITC recommendedtestingfor chronichealtheffectswith emphasison blood andnervoussystemdisorders,teratogenicity.carcincogenicity.mutageniceffects,andepidemiologystudies.TheITC also recommendedchemicalfateandenvironmentaleffectstesting.

In responseto theITC, EPA publishedan AdvanceNoticeof ProposedRulemaking(ANPR) for theanilinescategory(49 FR 108. January3, 1984).IntheANPR, EPA identified20 individualchemicalsin productionin 1982.rev)ewedthe availablehealthandenvironmentaleffectsinformation onthechemicals,indicatedtentativedatagapsin availablehealthandenvironmentaleffectsinformation,andrequestedpublic commentson a schemeto test representativecategorymembersratherthan all categorymembers.TheANPR namedsix subcategories(aniline.monochloroanilines,polychiorosnilines,mononitroanilines.polynitroanilines.andhalo-nitroanilines)andsevenrepresentativesubcategorymembers(aniline: 4-chloroanihine;3,4-dichioroaniline:4-nitroaniline:2.4-dinitroaniline; 2-chloro-4-nitroanihine.and2-bromo-4,8-dinitroaniline)forpossiblehealthandenvironmentaleffectstestingconsiderationundersection4(a)(1)(A) of TSCA. In responseto the ANPR, EPA receivedcommentsandnew informationfrom theAnilineAssociationandthe SubstitutedAnilines Task Force(SATF). an ind~s*rygrouporganizedasa specialprojectofthe SyntheticOrganicChemicalManufacturersAssociation.who~membersmanufactureor import oneormore of the substitutedanilines(Refs. Iand2). Commentswere also receivedfrom SodyecoInc.. EastmanKodak, andUplohn Company(Refs. 3 through5).TheAniline AssociationandSATFprovidedresultsof surveysofprocessorsto determinethe potentialforhumanexposureandenvironm~alrelease.The exposureandreleasedata

supplied by the SATF andsomeof thedatasuppliedby the AnilineAssociationweresubmittedasConfidential BusinessInformation [CBI)(Refs. 6 and7).

I!. TestingConsentOrderNegotiations

In the Federal Registerof .-\uaust ii.1986 (51 FR 23758) andin accordancewith the proceduresestablished:n 40CFR 790.28, EPA requestedthat porsocsinterestedin participatingIn ormonitoring testingnegotiationscitanilineandsevensubstitutedanwnescontactthe Agency. EPA held pubIcmeetingson August 12. 1986: October14.1986: January15. 1987; andFebruarytP,1987 to discusstesting appropriatefortheseeight chemicals.On or beforejuly7, 1988. five manufacturersof anilnaandfour manufacturersof subst;euteiianilinessignedeight separate‘Pest agConsentOrderswith EPA. Under oneOrder, the five manufacturersof ~n:Iinuagreedto conductor provide for theconductof the following tests:/n v:tomousemicronucleusassay.gramrnar:dacuteeffectstest,anddaphnidchroniceffects test. Under sevenseparateOrders,the manufacturersof the sevensubstitutedanilinesagreedto conductorprovidefor the conductof thefolln’.’.:natests for eachof the substitutedan:iirlestheymanufacture:Zn vivo cytogenet:cs(in vivo mousemicronucleusassay)for2-chloroaniline.4-chloroaniline.3,4~d.ichloroaniline.2-nitroaniline.4.nitroaniline,2.4-dinitroanuline:gammaridacuteeffects,daphnidchroniceffects,andrainbow trout acuteeffects(with triggerto rainbowtrout early-lifestage)for 2-chioroaniline:andalgaeacuteeffects.daphnidacuteeffects(with triggerto grammaridacuteariddaphnidchroniceffects),andrainbowtrout earlylife-stagetest for 2.6-dichloro-4-nitroariiline.The teststandardsto be followedand the testingschedulefor eachtestarespecifiedineachOrder.Proceduresfor submittingstudy plans,modifying the Order,monitoring the testing,andotherprovisionswere also includedin eachOrder.

Thefollowing tablepresentsthedispositionby EPA of the 20 antlines

Federal Re~istar/ Vol. 53, No. 161 I Friday, August 19, 1988 I Rules and Regulations

categorymembersreportedto be inproductionin 1982.

ANILINES CATEGORY MEMBERSDISPOSITION

CAS No. Chemicai name

62-53—3 An~ne —

95-51-2 2-Chl~’Oanthne i~ (~)t08-42-9 3.CNoroaniline (9106-47-8 4-Ch3ornan*~e (9608—27-5 2.3-Dichio,ovUne....... (2)

554—00—7 2,4-0~cnioroan4ine (2)

95—82-9 2,5.0ithIoro~nt~ne (995-76—1 3,4-Otchioroanitine 4 (9

634—93—5 2.4.6-Trctitoms~stine ) (3)

181 7—73—8 2’Bromo-4,6~rwb~oa,~ne...,,,j (8)

88-74-4 I 2-Nit,oanEne ~ (3)

99-09-2 3-Nitroaniiine ~ (9100-01—6 4-Ndroanitine.,.., (9

97—02-9 2.4.Otn,troecs5ne......,............... (‘)121—87—9 2.Ch1Oro-4a~tro~nthne..,... I (8)

6282-25—6 2-CNoo6*osntW~a.............I (3)

89—63—4 4-Chtoro-2-n8roenane.._,..,....1

(2)

635—22-3 4-ChIoro.3-nitroanliine (999-30—9 2,6.Dichtoro-4-nrtroan5ne C’)

827-9.4-1 2,6-Dibromo-4-nitroantk~e (9

Consent ~der: heaith and aquatic effects test.

IH. TechnicalSummary

.4. Manufacture,UseAndRelease

Aniline is producedby fivemanufacturers(DuPont,First MississippiCorp., Rubicon,Mobay ChemicalCorp.,andU.S.S.ChemicalCorp.) at fivelocationsin the UnitedStates.Productionwasabout790 millionpoundsin 1984 (Ref. 1). The productionvolumesfor substituted anilines rangefrom lessthan 1000pounds to 10 millionpounds.Themanufacturersof thesubstitutedanilineshaveprovidedEPA‘,vith exactproductionvolumesfor 1982as CBI (Ref. 8). TheTSCA section8(b)confidentialchemicalinventory updatereports that therehasnotbeenasignificantincreasein productionofthesechemicalsfrom levelsreportedin1982.

The manufacturersand processorsofaniline andsubstitutedanihinesreportthat thechemicalsare usedconsumptivelyas chemicalintermediates(Refs. 7 and9). Aniline isusedto produceisocyanates,rubberprocessingchemicals,dyes,andhvdroquinone,for drugmanufacture,andfor other uses including productionof herbicides,syntheticfibers,andphotographicchemicals.The primaryusefor most of thesubstitutedanilinesis as intermediatesin dyeandpigmentproduction.3,4-Dichloroanilineand2-chloroanilineareusedprimarily aspesticideintermediates,4-Nitro-aniline

and2-nitroanhhineareusedsolelyasintermediatesfor phenylenediamines.

Manufacturersof aniline report thatapproximately2.5million poundsweredisposedof by deepwell injection.2.5million poundswereincinerated.130.000poundswentto regulatedlandfills.49.500poundswere releasedto air, and14,700poundswerereleasedto water.Themanufacturersof aniline haveprovidedto EPA site-specificaquaticreleasevolumesfor 1984 as CBI (Ref.10). Total estimatedaquaticreleaseofaniline by processorswas85.155 poundsat 22 locationswith therangeoflocation-specificreleasebetween22.000pounds(3 locations)and1.000 poundsorless(14 locations)(Ref. 11). BothmanufacturersandprocessorsofsubstitutedanilineshaveprovidedEPA‘with releasevolumes for 1982as CBI.

B. HumanExposure1. Occupationalexposure—a.Aniline.

TheAniline AssociationhasprovidedEPA with informationon potentialoccupationalexposurefrom anilinemanufacturingandprocessingoperations(Refs. I and7). TheAssociationreportsthat thereis little orno occupationalexposureto anilinebecause:Few workersarepotentiallyexposedfor shortperiods:productionoccursin an enclosed,continuousprocessmostly in open-designplants(plantnot enclosedin abuilding); andrigorousworkplacecontrolsandindustrial hygienepracticesareusedtoprotectworkersfrom theknown acutetoxic effectsof aniline. Also, mostmanufacturersandprocessorsrequirethat employeeswearrubbersuits andglovesfor protectionin potentialexposuresituations suchas reactorentry, specialwork procedures,andsamplingandmaintenanceoperations,becausethe greatestpotential forexposureis throughdermalcontact(anilineis absorbedvery rapidlythroughtheskin). Air monitoring andmedical8urveillanceresultsshowcontrolpracticesareeffectivelypreventingexposuresto aniline(Ref. I).Aniline has excellentacute indicatorproperties;the olfactorydetectionlevelis 0.5 to I ppm. andacuteexposurecausescyanosis,a condition evidencedby bluish skin discolorationduetodeficientblood oxygenation.

TheAniline Associationsurveydatareportedthat487 workersinvolvedinmanufacturingarepotentiallyexposedto airborneanilineconcentrationlevelsbetween0.001 to 1.4 ppm, with 97percentof workersbelow 1 ppm.Anadditional1.524workersinvolvedininternalandoutsideprocessingofanilinearepotentiallyexposedto levelsrangingfrom 0.001 to 5 ppm with 99.9

31805

percentof total workerhoursatexposuresbelow2 ppm.TheOccupationalSafetyandHealthAdministration’s(OSHA) inspectionsummarydatatime-weightedaverages(TWA) were all below 0.25ppm andserveto supporttheAssociationsconclusions(Ref. 12). TheOSHApermissibleexposurelimit (PEL) foraniline is 5 ppm (Ref. 13). TheAmericanConferenceof GovernmentalIndustrialHygienists(ACGIH) T1vVArecommendedexposurelimit is 2 ppmfor aniline (Ref. 14).

b.Substitutedanilines.TheSATF hasprovidedEPA with confidentialinformationon potentialoccupationalexposurefrom manufacturingandprocessingoperationsof substitutedanilines(Refs.8 and8). TheSATF alsoreportsthatthereis little or nooccupationalexposureto the substitutedanilinescurrently in productionbecausevery fewemployeesarepotentiallyexposed.The SATF reports thatproductionoccursovershort timeperiodsin a closedcontinuousprocessduring which the chemicalis consumed:that workplacecontrolsandindustrialhygienepracticesareusedto protectworkers from the known or suspectedacutetoxic effectsof the substitutedartihines, and that air monitoringandmedicalsurveillanceresultsshowcontrolpracticesareeffectivelypreventingexposuresto the substitutedanilines.Somesubstitutedanilinesalsohaveexcellentacuteeffectsindicatorpropertieslike thoseof aniline.

A studyby onemanufacturer!processorto evaluatetheeffectsofpotentialairborneexposureofmanufacturingworkers to 4-chioroanilineon variousbiological(blood) parameters reported that: (1) AUthemethemoglobinlevelsmeasuredfallwithin what hasbeentraditionallyregardedasanormalrange,(2) a smallstatisticallysignificantelevationinmethemoglobinfollowing thework shiftwasobservedamongemployeesinvolvedin 4-chloroanihinemanufactureandthe matchedcomparisongroupsuggestingtheobservedincreaseinmethemoglobinamongworkersmay notbe work-related, and (3) therewasnocorrelationbetweenpost-exposuremethemoglobinand4-chioroanilineairsamplingdatawithin the narrowrangeof low level exposurestypical in thiswork setting (Ref. 15). A majormanufacturer/processorof chloro- andnitroanihinesreportsan averageof 3casesperyearor methemoglobinemia.definedas oxygensaturationbelow90percent.observedat the their main plantover the last 10 years)Ref. 16). Over the

Ing.Decision to terminate rulemak;ng found else-

where in th,~ssueof F.d,va~Registur.Consent Order: heattheffects testing.Consent Order: aquatic effects testing.

31806 Federal Regi.s~er/ Vol. 53, No. 161 / Friday, August 19, 1988 / Rules and Regulations

last 5 years,no methemoglobi~emiawasobserved.

2. Consumerexposure.Theleis noknown or suspectedconsumerexposureto anyof theaniline categorymembersasa resultof TSCA-coveredactivitiesbecausetheyarewholly consemedchemicalintermediates.

C. EnvimnrnentalExposure

Therearefew monitoringdataavailablefor aniline andthesubstitutedanilinesin wastewaterof sediment.Ewing et a!. in 1977sampledsurfacewatersfrom 204sitesnearheavilyindustrializedareasacrossthe U.S.Aniline andsubstitutedanilineswerenot detectedat concentrationsaboveIppb (Ref. 17). In anotherstudywastewater,receivingwatersandsedimentsneara plant manufacturingabroadrangeof chemicalswereanalyzedfor organicpollutants(Ref. 18). One

sampleof wastewatercontained0.02ppm of aniline. Aniline wasnot detectedin river wateror sediments.Chloroaniline(isomersunspecified)wasnot detectedin wastewateror riverwaterbut wasfoundin sedimentat 1 to2 ppm. Plantandsamplinglocationswerenot reported.

GamesandHites in 1977measuredorganiccompoundsin untreatedandtreatedeffluentoriginating from a dyemanufacturingplant(Ref. 19). Resultsshowedthe presenceof six anilinecompounds.Thecompoundsincludedaniline, chioroaniline,dichloroaniline,nitroaniline. tribromoanilineandbromodinitroaniline.Theconcentrationsrangedfrom 36 to 480ppb for rawwastewaterto 7 to 96 ppb for treatedeffluent.

USEPAdatain the STORET systemincludea total of 48datapoints orobservationson environmentallevelsof

aniline in streams,and42 datapointsorobservationson levelsof 2-nitroanil nein streams(Ref. 20)The meanresiduallevel of aniline was9.47 ppb. withmaximumandminimum valuesof 13and1 ppb, respectively;the STORETdatawere collectedbetweenAugust1978andAugust 1980.The meanresidual level for 2.nitroanilinewas0.39ppb with maximumandminimum valuesof 1.7 and0.1 ppb. respectively:theSTORETdatawerecollectedbetweenJanuary1983 andMay 1985.

D. Physicochez-aicalProperties

I. Watersolubility, vaporpressure.and octariol/waterpartition coe~/ci’enEPA hasestimatedwatersolubtlities,vaporpressures.andthe log octanol!waterpartitioncoefficients(log P~ofaniline andsix representativesubstitutedanilines.andthesedataarcpresentedin thefollowing table:

PHYSiCAL AND CHEMICAL PROPERTIES OF ANILINE AND Six SUBSTITUTED ANILIHES

Chemical

.+

Emp~ncalformuta Mo4ecr W tso~*~ty~

Logoct.anol/~

coefficient(L0gXOW)

s~~

(KOC)

,

Vapor p!essure Henrysa.’~,

An~ine .... 62—53—32-Chioroaniline 95—51—24-CNoroar8Une 106—47—83.4-Dictiloroanane - 95—76--i2-Nitroan~line 88—74—44-Nitroareline 100-01-62.6-Oichioro-4-NitroaM,ne 98-30—9

c.H,NC.H.C1NC,H,CSNC,H,C4,NC.,I-l,N,O,C,H,N

10,

C.H,C1,N~O2

93.13127.57127,57162.02138.t3138.13207.02

I 35,~3,900

‘ 3,900I 51

1,200800

49

10.901,911.832.691.691.39

2.45 to3.29

47 0.473 25’ C 0 17.’ t~J261 0.22 25’ C 095 . 10236 I g.s <to-’ 25~C 0 5.4 .

691 5.8x 10’ 25~C 024 . 10198 3.8x to-i 25~C 055 . 10136 2.9 ~10’ 25’ C 066. 1C

1,000 1,45x 10’ 25’ C Ott - 0~

= Measured value.

Experimentalvaluesof someparametersareavailablefor aniline.4-chloroaniline,and3,4-chloroaniline(Refs.21 through24). Thecalculatedandexperimentalvalue8indicatethat,underequilibrium conditions,aniline,thechloroanilines,andthenitroanilineswillremainin thewatercompartment,althoughotherdatasuggestthatanilineswill bind chemicallyto sediment(seeUnit IlI.D.3).

2. Soil mobility.Theadsorptionpropertiesof aniline andsomesubstitutedanilineshavebeenreportedandEPA hasestimatedsoil organic-carbonsorptioncoefficients(Koc) fromcalculatedlog P valuesusing equationsdevelopedby Kenaga,andKenagaandGoring (Refs.25 and26). (Seetable forthesevalues.)ThemeasuredandestimatedKoc valuesindicatethataniline andsubstitutedanilinesadsorbweakly to moderatelyto organicmatterin soil andsedimentandthereforecanbe consideredmoderatelyto highlymobile.However,thereareexperimentaldatato indicate that4-

chloroanilineand3,4-chloroanilineandotheraromaticainineschemicallybindto organicsin soil andsediment;thereforetheseandpossiblyothercategorymembersmaybe muchlessmobile in soil andsedimentthanpredictedby the Koc (Refs.27 through31).

3.Presistence.Chemicalfate dataonaniline indicatethat it is readilybiodergradableandoxidizable insurfacewaterandsewagesludge(Refs.32 through35). The overallexperimentaldegradationhalf-life in surfacewaterislessthanI day (Refs. 36 and43).

Dataon 2-chioroaniline,4-chloroaniline,and3,4-dichloroaniline(DCA) indicatethe majorreactionin soilis chemicalbindingwith thehumicacidfraction(Refs.27 through31). Afterbinding. thechloroanilinearenotextractableassuch.As theconcentrationof the chemicalsin thesoil increases.polymerizationof thesechemicalsalso occurs.The humicadsorptionpropertiesof thechioroanilinesarebelievedto correlate

with the organiccontentandpH of thesoil (Ref. 37). Microbial metabolismoccursslowly in soil becausethechloroanilinesbind to soil organics(Refs.38 through42). Thechloroanilineshaverelatively low log P valuesandarethereforenot likely to bioconcentrateinfatty tissueof aquaticorganisms.althoughtheir lower watersoluhilitiesandhigherlog P valuesindicate theyaremore likely to do so than aniline.

Photodegradationis likely to beaprimary routeof aquaticdegradationofthe chloroanilines(Refs.43 through41).The experimentalhalf-life of DCA indistilled water, naturalseawater,andInstantOceanis lessthan I day(Ref.43). Theratesof biodegradationofmonochloroanilinesareestimatedto beslowerthan aniline in the aquaticenvironment(Ref. 46). In aerobicenvironments4-chloroanilinebiodegradesfasterthanDCA. Inanaerobicenvironmentsthe reverseistrue (Ref. 47). Somemonochioroanilines

FederalRegisterI Vol. 53, No. 161 / Friday, August 19, 1968 I Rules and Regulations 31807

arereportedto be degradedin activatedsludge(Refs. 33 and47).

Availabledataon thechemical fate ofthenitroanilinesandhalogenatednitroanilinesarelimited. Insemicontinuousactivatedsludgetesting,4-nitroanilinehasbeendescribedasreadilydegradableand 2-nitroaniline asresistantto degradation(Ref. 48). 4-nitroanilineand2,8-dich1oro-~4-nitroaniline (DCNA) undergomicrobialdegradationin pureculture(Refs.49 and50). The relativelylow log P valuesindicatethe nitroanilinesandhalogenatednitroanilinesarenot likelyto bioconcentratein aquaticorganisms.Thenitroanilinesandhalogenatednitroanilinesmay,like otheraromaticamines,chemicallybind to organicsinsoilsandsediments,althoughtherearerio datato confirm this effect for thesechemicals.

IV. Testing Program

A. EnvironmentalEffects

In its FourthReport to the EPA,publishedin the FederalRegisterof June1. 1979 (44 FR 31866).the ITCrecommendedchemicalfatetestingbecauseof suspectedenvironmentaleffectsandalsobecausetherewereconflictingreportson the ability ofanimals,plants.andmicrobestometabolizeandtoleratethesechemica’ls~TheITC recommendedenvironmentaleffectstesting becausereportsofoccurrencesof residuesandtheirpersistencein waterandsoil suggesteda highly dispersivedischargeinto theenvironmentandavailabledataraisedaconcernthat categorymembersmayproduce adverseeffects.

UsingCBI suppliedby manufacturersandprocessorsandinformationfrom theopenliterature,EPA hascalculatedworst-caseaquaticpredictedenvironmentalconcentrations(PECs) foraniline, 2-chloroaniline.and2,6-dichloro-4-nitroaniline,which werethecategorymembersjudged to be releasedin significantamounts(Ref. 51). BecausetheAgencyhasfew dataon the fateofthe substitutedanilinesin theenvironment,calculationof their PEGswasbasedon theworst-cageassumptionthatnoneof thesubstitutedanilinesareaffectedby physicalorbiological processesotherthandilutionin the dischargeenvironment.Foraniline, PECswerecalculatedusingameasuredoveralldegradationhalf-lifeof 17.5 hours(% day) whichincludesbiodegradation.oxidation,photolysis,andhydrolysisin naturalwaters (Ref.52). In addition,theconcentrationin thedischargeenvironmentwasconservativelybasedon the lowest riverflow rate thatwould not be exceeded5

percentof the time. ThePECsfor anilineandthesubstitutedanilinesjudgedto bereleasedin significantamountsarenotdescribedherebecausetheyarederivedfrom CBI data.

The Agencyhas reviewedtheavailabledataon environmentaleffectsandthepotentialfor environmentalexposureto other anilines categorymemberscurrentlyin production(seeNoticeof Terminationof Rulemaking forCertain Anilines Category Membersappearingelsewherein this issueof theFederalRegister).The Agencyhasdeterminedthat,giventhelowanticipatedandobservedexposuretothesechemicalsandin thelight of theenvironmentaleffectsdataavailableforthis category,thesechemicalsdo notreachlevelsin theenvironmentthat‘raise a concernfor adverseeffects.

EPA has estimatedthe potential forreleasesof anilinescategorymemberstoadverselyaffect aquatic organismsbyexamining available aquatic toxicitydataandby comparingacutevertebrateand invertebrateLC5O’s to the site-specificPECs calculatedas describedinUnit IV.A.2.

EPA hasdeterminedthatconcentrationsof aniline. 2-chloroaniline,andDCNA in theaquaticenvironmentresultingfrommanufacturingand processingcouldreachlevelswhichmaybeharmful toaquaticorganisms(i.e., LC5A)’s ofsensitiveaquaticspeciesof anilIne, 2-chloroaniline,andDCNA arelikely tobe lessthanor equal to 1000 x thepredictedenvironmentalconcentrationsor lessthanor equal to 1 mg/L).Therefore,additional acutetoxicitytesting is neededto determinetheeffectsof: Aniline on daphnids,2-chloroanilineon gainmaridsandrainbowtrout, andDCNA on algaeanddaphnidswith triggerto gammarids.Testing to determinethechroniceffectsof anilineon dephanids,2-chioroanilinefrom acutetriggerto daphmd orgammaridand rainbow trout earlylifestage,andDCNA earlylife stageinrainbow trout is also neededto assessthe potentiallong-termhazardof thesechemicals to aquatic organisms.

The following is a summaryofavailableaquaticeffectsinformationtheAgencyhas consideredin its decision toissuea ConsentOrderfor aquaticeffectstestingof aniline, 2-chioroaniline,and2,8-dichloro-4-nit.roaniline.The96-hourEC5Ofor aniline in freshwateralgae(Selenastrumcapricomutom)is 19mg/L andthe48-hourEC5O for 2-chloroanilinein freshwateralgae(Scenedesmuspannonicus)is 32 mg/L(Refs.53 and54). The48-hourLCSO foraniline in Daphnia magna is 0.85mg/L

and the 48-hour EC5Ofor 2-chloroanilinein Daphniamagnais 0.48mg/L (Refs. 55and 54). The 96-hourLC5O’s for anilineand2-chloroanilinein fatheadminnowsare134 rng/L and5.8 mgJL. respectively(Ref. 58). The96-hourLC5O for aniline flrainbow trout is 8 mg/L (Ref. 57). The96-hourLC5O’s for 2,8-dichloro-4-nitroaniline in bluegill sunfish andrainbowtrout are1.08 mg/L and0.56mg/L. respectively(Refs. 58 and59).

B. HealthEffects

In its FourthReport44 FR 31866. theITC recommendedthatall chemicalsintheanulinescategorybe testedforchronichealtheffectswith emphasisonbloodandnervoussystemdisorders.teratogenicity,caricinogenicity.mutagenic effects,andepidemiologystudies.TheITC baseditsrecommendationsfor chronicheaitheffects(with emphasison blood andnervoussystemdisorders), forteratogeniceffectstesting, andforepidemiologystudieson the potent:al forsomecategorymembersto causemethemoglobinemiain humans.The ITCrecommendedmutagenic andcarcinogeniceffectstesting becausesomecategorymemberswere reportedto causemutagenicand/orcarcinogeniceffects,andtheresultsraisea tUSPtCiOfl

of theseeffectsin untestedmembers.TheAgencyin its ANPR for the anilinecategory,49 FR 108. proposedtesting forreproductiveeffectsbasedon thepotential for somecategory memberstocausemethemoglobinemiain humans.

TheAgencyhasreviewedtheavailabledataon healtheffectsandthepotential for humanexposureto thesevenanilinescategorymembersnamedin theConsentOrdersandtheotheranilinescategorymemberscurrently~nproduction (seeNotice of TerminationofRulemakingfor CertainAnilinesCategoryMembersappearingelsewherein this issueof theFederalRegister).TheAgencyhasdeterminedthat,giventhelow anticipatedandobservedexposureto thesechemicalsandin light of thehealtheffectsdataavailablefor thecategory,thesechemicalsdo not reachlevelsin the workplaceenvironmentthat raisea concernfor chronic,developmental,andreproductiveeffects.

However,potentialhumanexposureto aniline, 2-chloroaniline,4-chloroaniline,3,4-dichloroaniline.2-nitroaniline,4-nitroaniline,and2.4-dinitroaniline resultingfrommanufacturingandprocessingissufficient to raisea concernfor effectson humanhealththrough adverseheritablemutageniceffects.Thereforeadditional testingto character:zeth~

31808 Federal Register / Vol. 53, No. 161 / Friday, August 19, 1988 I Rules and Regulations

mutagenicityfor sevencategorymembersis necessary.

This additionaltestingis necessaryaspart of a tiered testingapproachwhichinvolves a programreview to follow thedevelopmentof thein vivo cytogeneticsdataandconsidersall availablemutagenicandhealtheffectsdatatodeterminethe needfor furthermutageniceffectsor other healtheffectstesting.EPA is deferringanydecisionasto the needfor carcinogenicitytesting ofthesubstitutedanilinesuntil it hasreceivedthe resultsfrom all themutagenicitytesting to be performedundertheConsentOrders.Dataon thecarcinogenicpotentialof aniline hasbeenevaluatedandjudgedto beadequate.TheAgencywill announceitsdecisionon furthermutagenicityorcarcinogenicitytestingneedsin aseparaterulemaking.

The following is a summaryofavailablehealtheffectsinformation theAgencyhasconsideredin its decisiontoissueConsentOrdersonly for mutageniceffectstestingof sevenanilinescategorymembers.

1. Acuteeffects.The primaryacuteeffect in mammalsassociatedwithexposureto aniline andsomesubstitutedanilinesis anincreaseinmethemoglobinlevelsin blood(Ref. 60).However,a recentstudysponsoredbyAmericanHoechstshowsthat not allsubstitutedanilinesreadily causeincreasedlevelsof methemoglobininrats(Ref. 61). Thestudy wasdesignedtorate themethemoglobin-inducingpotencyof categorymembersrelativetoaniline. usinghigh dosesto maximizethe amountof methemoglobinproduced.Doseswereequimolarto 100and400mg/kg of aniline. When testcompoundsinduced the formationof methemoglobinabovevehiclecontrolsin adose-dependentmannertheywereconsideredpositive.For compoundsclassifiedaspositive, theresultsof the100 mg/kgequimolardoesat 1 hourwere thenstatisticallycomparedwith the100mgIkg aniline resultsto determineif thetestcompoundwasmorepotent,equipotent,or lesspotentthan aniline. Testcompoundsthatfailed to inducemethemoglobinemiaat eithertime point(1 hourand6 hours)or dosewereconsiderednegative.

Only 3-chloroanilineand4-chloroanilineweresignificantly morepotentmethemoglobinproducersthananiline. Fourchemicalswereequipotentto aniline: 3-nitroaniline.4-nitroaniline,2,4-dinitroaniline,and3,4-dichloroaniline:andfour werelesspotentthan aniline: 2-chloroaniline.4-chloro-3-nitroaniline,2,3-dichloroaniline,and3,5-dichloroaniline.The otherelevenchemicalswerenegative.

Numerousreportsandstudiesdescribesecondaryeffectsfrom acutehumanandanimalexposureto aniline,4-chloroaniline,and4-nitroanilinerelatedto methemoglobinemiaandresultinganoxia(Ref. 62). Thesecondaryeffectsinclude cyanosis.andcentralnervoussystemsymptomswhich resultfrom the decreasedoxygen-carryingcapacityof rnethemoglobicblood.Changesin bloodchemistryanddevelopmentof Heinzbodiesalso occur.Removalfrom exposureusuallyallows anormalizationof hetnatologic conditions,followedby ameliorationof secondaryabnormalities.

2. Metabolism.Studieson thedispositionandmetabolismof aniline. 4-chloroaniline,4-nitroaniline,2,4-dinitroaniline.2-bromo-4.8-dinitroaniline.2,6-dichloro-4-nitroaniline.and4-chloro-2-nitroanilinein ratsindicatethesechemicalsarerapidlymetabolizedandexcreted(Refs.63 through88). For example,the wholebody half-lifeof thesechemicalsrangesfrom ito 7 hours:andwithin 2 to 3 days,clearanceof chemical-derivedradioactivity from the body wasalmostcomplete.

Aniline andsomeof thesubstitutedmembersof the category(2-chloroaniline.3-chioroaniline,4-chloroaniline,2,3-dichlororaniline,2.4-dichloroaniline,3,4-dichloroaniline,3-nitroaniline,4-nitroaniline,and4-chloro-3-nitroaniline)arebiotransformedinratsandother mammalsintointermediateswhich initiate theformationof methemoglobinfromhemoglobin(Ref. 60). Therearetwometabolicpathwaysinvolvedin themetabolismof aniline andtheothermethemoglobin-formingmembers:(1)Thehydroxylationof thearomaticringcarbonsto produce phenolswhich arethe precursorsfor coniugatedproductsexcretedin urineor bile or (2) thehydroxylationof thenitrogenatom toform phenythydroxylamineandnitrosobenzenewhich converthemoglobinto anoxidizedform,methemoglobin.an irreversibleoxygencarrier.However, the sensitivity tomethemoglobin-forminganilinesvariesamong mammals. Cats are themostsensitiveandproducethehighestandmost sustained levelsof methemoglobin.Humans,dogs. rats, andrabbitsarelesssensitive(orderof decreasingsensitivities).Thevariationinsensitivitycould bedueto theextenttowhichthe chemicalis metabolizedtophenylhydroxylamineor to thedifferencesin the activities of enzymesthat~tutoote the reductionofmethemoglobinin the red cell backtohemoglobin.

3. Subchronicandchroniceffects.Resultsfrom prechronicor subchronicandchronic(oncogenicity)oral studiesin ratsor ratsandmice for threemethemoglobin.inducfngchemicals(aniline.4-chloroaniline.and4-nitroaniline)havebeenreported(Refs.69 through75). Somecommoneffectsthat resultfrom long term exposuretoaniline and4-chloroanilir.eat doses(10to 100mg/kg/day)that inducesignificantmethemoglobininclude:Anemia.red blood cell Heinz bodies,dose-relatedincreasein spleenweightandsize, dose-relatedcongestionofsplenicpulp, increasedred bloodcellturnoverrate,anddose-relatedincreasedpigment(hemosiderinengorgement)in spleenandin kidneyandliver at high doses(> 10 mg/kg!day).At higherdoses(30 to 100mg/kg!day), adose-dependentincreasedincidenceof primarysplenicsarcomas.principallyin male rats, wasreportedfor aniline and4-chioroaniline(Refs.69and75).

Resultsof achronicoralstudy in ratsusing 4-nitroanilineindicatetheadministrationof4-nitroanilineat levelsup to 9 mg/kg/dayfor 2 yearsdid notcauseanytreatment-relatedoncogeniceffects(Ref. 74). Thestudywasdesignedto determinewhetherchronicoroncogeniceffectsoccurfrom long-termexposureto 4-nitroanilineat dosesthatinduceincreasedlevelsofmethemoglobinin rats. Methemoglobinlevelswere increasedovercontrolsatmid (1.5 mg/kg/day)andhigh (9.0 mg/kg/day) dosagelevels. Slight anemiawasobservedmainly at the high dosagelevel. At the low (0.25 mg/kg/day)dosagelevel, the only treatment-relatedchangewasslight brownpigment insplenicreticuloendothelialcells.Theonly treatment-relatedchangeat the midandhigh dosagelevelswasaccumulationof brown pigment insinusoidalmacrophagesin the liver andin reticuloendothelialcells in the spleen.Resultsof an oral 90-daysubchronicstudy in mice using4-nitroanilinehavebeenreported.Effects in both sexesgiven30 and100mg/kg/dayinclude:Methemoglobinemia.Heinzbodies,increasedred bloodcell turn overrate,increasedspleenandliver weight.andpigmentdepositionwithin phagocyticcellsof spleen,bonemarrowandliver(Ref. 74). The NationalToxicologyProgram(NTP) is sponsoringan oralchroniceffects-oncogeriicitystudyof 4-nitroanilinein miceat doselevelsof 0. 3.30, and100mg/kg/day(Ref. 76).

Subchronicinhalation studiesusingratsandmicewith the methemoglobininducers3-chloroaniline.3.4-dichloroaniline.and4-nitroanilinereport

Federal Register / Vol. 53, No. 161 / Friday, August 19, 1988 / Rules and Regulations 31809

the sametypeof effectsthatoccuratlower dosesandover shorterexposureperiodsin oral studiesin ratsandmice(Refs. 77 through81). Subchronicoralexposureof ratsto 4-chloro-3-nitroaniline resultedin reducedtestes-weight-to-brain-weightratio at 18 mg/kg/day andtesticularatrophyalongwith other toxic effectsat 90 mg/kg/day(Ref. 82). No treatment-relatedeffectswereobservedat or below 100ppm inthe diet in two chronic/oncogenicitystudiesin ratsanddogs for 2,6-dichloro-4-nitroaniline(DCNA), which doesnotinducesignificantmethemoglobinemiain mammals(Ref. 83). An oncogenicitystudyof DCNA in mice is in progress(Ref. 84).

Becausethereis evidencefromstudieson themetabolismofmethemoglobin-producinganilinesfor anon-genotoxicmechanismfor theinductionof hemangio-andfibrosarcomasin the spleenof ratsfromdietaryexposureat high concentrations,andbecauseEPA wantsto reviewallrelevantdataon all the anilinesbeforemakinga determinationas to the needfor oncogenicitytesting. the Agencyisdeferringits decisionon the needforadditionaldataon oncogeniceffectsofsubstitutedanilinesuntil the resultsofthe in vivo mutagenicitytestsareavailable(Ref. 85). The availabledataon the oncogeniceffectsof aniline areadequatefor TSCA risk assessmentpurposes.

Also, afterreviewingtheavailablereportsandstudies on the acuteandchronichealtheffectsof theanilinescategorytheAgencyhasfound noevidenceof adversehematologicorcentralnervoussystemeffectsthatarenot likely to berelatedto the decreasedoxygen-carryingcapacityofmethemoglobicblood.Thedataprovideno basis to believethat thesechemicalsmaypresentanunreasonablerisk ofadversehematologicor centralnervoussystemeffectsat anticipated exposurelevelsas manufacturersandprocessorscontrol potentialhumanexposurebelowthe thresholdfor methemoglobinemia.Therefore,the Agencyhasconcludedthatadditional informationonhematologicor centralnervoussystemeffectsof aniline andsubstitutedanilinesis not necessaryat this time.

4. Developmentaltoxicity. Aniline, apotentmethemoglobinproducer,wasobservednot to bedevelopmentallytoxic in ratsat levels(100 mg/kg) thatproducedmaternalandfetal toxicitycommonlycausedbymethemoglobinemia(Ref. 86). Timedpregnantmice treatedwith aniline (500mg/kg/day)duringdays7 through14 ofgestationrevealedno apparenteffecton

numbersof litters produced;however,offspringviability throughthe first threepostpartumdayswassignificantly lowerthanfor the control group. Also,reductionsin birth weightandweightgainwereseenin aniline-treatedlitters(Ref. 87). No treatment-relatedmaternalor embryotoxicitywasobservedbelow125 mg/kg/day(oral administration)of4-nitroanilinein NewZealandrabbits(Ref. 88). 4-Nitroanilineadministeredbygastricintubationto pregnantratsat adoseof 25 mg/kg/dayfrom day 6 to 19of gestationwasnot maternallyordevelopmentallytoxic (Ref. 89). At 85mg/kg/daysomematernaltoxicity(increasedspleenweight) andfetotoxicity (reducedfetalweight) wereevident:however,no developmentallytoxic effectswereobserved.At 250mgikg/day,4-ni troaniline producedmaternaltoxicity. embryotoxicityandterata.No treatment-relatedmaternalordevelopmentaltoxicity wasobservedator below300mg/kg/dayof 2-nitroaniline to pregnantratsaftergavageadministrationon days6 to 15 ofgestation.Significantevidenceofmaternaltoxicity wasobservedat 2-nitroanilinedosagesof 600mg/kg with asingle malformation in one fetus eachfrom two litters at thatdosage(Ref. 90).Pregnantratsexposedto 1.1 and1.7 mgim3 of 2,4-dinitroanilinedevelopedmaternalandembryotoxicity,but nootherdevelopmentaltoxic effectswereobserved(Ref. 91). Pregnantrabbitsexposedto DCNA showedno maternaltoxicity or developmentaltoxicity at1.000ppm in diet (Ref. 92). A secondteratologystudyof DCNA in ratsis inprogress(Ref. 84).

The dataprovide no basisto believethatthesechemicalsmay presentanunreasonablerisk of adversedevelopmentaleffectsat anticipatedexposurelevels, as availabledatashowno developmentaleffectsthatoccuratexposurelevelsat whichsomecategorymemberscausemethemoglobinemiaandmanufacturersandprocessorscontrolpotential human exposurebelow thethresholdfor methemoglobinemia.Therefore,theAgencyhasconcludedthatadditional information on thedevelopmentaleffectsof aniline andthesubstitutedanilineg is not necessaryforrisk assessmentpurposesat this time.

5. Reproductiveeffects.Anilineadministeredsubcutaneouslyin femalerats(averageweight150grams)forsevendaysat 50 mg/day causedalterationsin steroidalhormonelevelsof the corporaluteum (Ref. 93). 4-Nitroaniline administeredby gastricintubationat doselevelsof 0.25, 1.5 and9.0 mg/kg/dayto the FO andFlgenerationof male andfemalerats

duringpre-matinggrowthandthroughensuingmating. gestation.andlactationintervalsshowedno significantadverseeffect on mortality ratesor body weightsin the FO andFl generations(Ref. 94). inthe FO generation,the male fertilityindexandpregnancyrate for the highdosegroupwere lower thancontroldata:however,only for the pregnancyratewas this differencefrom the controlgroupstatisticallysignificant. In the Flgeneration.mating. pregnancy.andfertility indiceswere comparablebetweencontrolandtreatedgroups.~oadverseeffectsof treatmentwereindicatedduring eithergenerationinparturitionor litter sizedata,pupweightdate,pup survival, or sexdistributiondataor deadpup observations.Likewise, grossandhistopathologicalevaluationof selectedtissuesfrom FtandF2 pups or adultsto include testes~epididyrnidesof Fo males(highdosegroup)did not revealan adverseeffect.Therecentchronicstudyusing anilinehasno mentionof long-termeffectsonreproductiveorgans(Ref. 69). Chronicstudieson 4-chloroanilineand4-riitroaniline haveno mentionof effectson reproductiveorgans(Ref. 70 and74).4-Chloro-3-nitroaniiinecausedtesticulareffectsin ratsafter subchronicoralexposureat 90 mg/kg/day.but theanimalsshowedothertoxicities as well(Ref. 82). TheNOEL wasreportedascloseto but below3.8 mg/kg/day.The3.8 mg/kg/daydoseproduceda minimaltoxic response.A spermmorphologyvaginal cytology (SMVCE) study of 4-nitroaniline reportedno effectsof thechemicalon mouseestrouscyclesbutreducedspermmotility in miceat 100mg/kg/day(Ref. 95). An SMVCE studyof 4-chloro-2-nitroanilinereportednoeffectson reproductiveparametersinmale rats: however,the chemicalappearedto interferewith the relativefrequencyof estrousstages(600 and1.200mg/kg/day)(Ref. 96). This effect islikely to becausedby alterationinhormonalactivity. A threegenerationreproductivestudyof DCNA reportednoeffectson reproductiveparametersinmaleor femaleratsat 100 ppm and10ppm in diet (Ref. 97).

Thedataprovide no basisto believethatthesechemicalsmaypresentanunreasonablerisk of adversereproductiveeffectsat anticipatedexposurelevels,as availablereproductiveeffectsdatashownoreproductiveeffectsthatoccuratexposurelevelsat which somecategorymemberscausemethemoglobinemiaandmanufacturersandprocessorscontrolpotentialhumanexposurebelowthethresholdfor methemoglobinemia.Therefore,the Agencyhas concluded

31810 Federal Register I Vol. 53, No. 161 I Friday, August 19, 1988 / Rules and Regulations

that additional informationon thereproductive effects of aniline and thesubstitutedanilines is notnecessaryforrisk assessmentpurposesat this time.

6. Mutageniceffects.The followingdatawereconsideredby EPA forevaluatingthe risk of mutagenicinjuryto humanhealthfrom exposureto sevencategorymembers.

a. Aniline is reportedto havenegativeresultsin the following genemutationassays:Salmonella,E. co/i, WP2 uvr A,andAspergillus(Refs.98 through101).Aniline is positive for theL5178YTK, ±mouselymphomagenemutationassayandnegativefor theDrosophila sexlinked recessivelethal assay(SLRL)(Refs. 102 through104). Aniline isnegativefor sisterchromatidexchangein humanlymphocytes,andnegativeforchromosomalaberrations in culturedChinesehamsterovary cells(Refa. 105and106).Aniline causedan increasedfrequencyof sisterchromatidexchange(SCE) in vivo in mousebonemarrowcells andin vitro with Chinesehamsterovary cells (Refs.107and108).Anilinealsocauseda slight increaseinfrequencyof SCE’s in culturedhumanfibroblasts(Ref. 109). EPA believesthatan in vivocytogeneticstest is necessaryfor risk assessmentpurposes,andmanufacturershave agreedto performthetesting(mousemicronucleus).

b. 2-Chloroanilineis negativein theSalmonellagenemutation assay,andthere are no data oncytogeneticeffectsof 2-chloroaniline(Ref. 110). EPAbelievesthatan in vivocytogeneticstestis necessaryfor risk assessmentpurposes,andmanufacturershaveagreedto performthetesting(mousemicronucleus).

c. 4-Chloroanilineis reportedto havepositiveresultsin the following genemutation assays;Salmonella,S.coil polA, AspergillisandLSI7BY TKI±mouselymphoma(Refs.101 and111 through113). 4-Chloroanilineis positive forsister chromatid exchangeandchromosomalaberrationeffectsin vitro(Ref. 114).EPA believesthat an in vivacytogeneticstest is necessaryfor riskassessmentpurposes,andmanufacturers have agreedto performthe testing(mousemicronucleus).

d. 3,4-Dichioroaniline is reported tohavenegativeresultsin theSalmonellagenemutationassayandpositive resultsin the Aspergillusgenemutation assay(Refs. 99 and 115). There areno data onthecytogeneticeffectsof 3.4-dichloroaniline.EPA believesthat an inviva cytogeneticstestis necessaryforrisk assessmentpurposes,andmanufacturershaveagreedto performthe testing (mousemicronucleus).

e. 2-Nitroanilineis reportedto havepositive resultsin theSalmonellagene

mutation assay;thereareno dataavailable on the cytogeneticeffects of 2-nitroaniline (Ref. 118and118). EPAbelievesthatan in vivacytogeneticstestis necessaryfor risk assessmentpurposes,andmanufacturershaveagreedto performthe testing(mousemicronucleus).

f. 4-Nitroanilineis reportedto havepositiveresultsin the SalmonellaandL5178YTK±mouselymphomaassaysandnegativeresultsin theDrosophilaSLRL assay(Refs. 117, 119and122).4-Nitroaniline is weakly positive for sisterchromatidexchangeandchromosomalaberration effectsin vitro (Ref.120).EPA believesthatan in vivacytogeneticstestis necessaryfor riskassessmentpurposes.andmanufacturers haveagreedto perform~he testing (mousemicronucleus).

g. 2.4-Dinitroanilineis reportedtohave positive effectsin the Salmonellagenemutation assayandis negativeintheDrosophilaSLRL assay(Refs.116,121,and123). 2.4-Dinitroaniline is alsobeing testedfor in vitro cytogeneticseffects(Ref. 120). EPA believesthatanin viva cytogeneticstestis necessaryforrisk assessmentpurposes,andmanufacturershave agreedto performthetesting (mousemicronucleus).

V. Export Notification

Theissuanceof theseConsentOrderssubjectanypersonwho exportsorintendsto exportaniline, 2-chloroaniline, 4-chloroaniline,3,4-dichloroaniline,2-nitroaniline,4-nitroaniline,2,4-dinitroaniline.and2,8-dichloro-4-nitro-anilineto theexportnotificationrequirementsof section124b)of TSCA. Thespecificrequirementsarelistedin 40 CFR Part707.EPA addedandreservedsubpartCof 40 CFR 799.5000for a list of testingconsentordersissuedby EPA. Thislisting servesasnotificationto persons,who exportor whointendto exportchemicalsubstancesor mixtures whicharethe subjectof testingconsentorders,that 40 CFR Part 707 applies.

VI. RulemakingRecord

EPA hasestablisheda recordfortheseConsentOrders (docketnumberOPTS-42054B).This recordcontainsthebasic informationconsideredby theAgencyin developingtheseTestingConsentOrders.

A. SupportingDoc~imentation(1) TestingConsentOrdersbetweenthe

five manufactur himpertsrsof anilineandtheAgency.

(2) TestingConsentOrders betweenthefour manufacturers/importersofsevensubstitutedanilinesandtheAgency.

(3) FederalRegisternottcespertainingtothis noticeconsistingof

(a) Notice containingthedesignationof theAnilines Categoryto the Priority List (44 FR107: June1. 1979).

(b) Advance Notice of ProposedRulemakingfor theAnilines Category(49 FR108: January3. 3984).

(c) Noticesoliciting interestedpartiesfordevelopingaConsentOrderfor Aniline andSevenSubstitutedAnilines (51 FR 28758;August 11. 1986).

(dl Notice of interim final rule onproceduresfor developingenforcedbleconsentagreements(51 FR 23706; June301986).

(4) Communicationsconsistingof:(a) Written letters.(b) Contactreportstelephone

conversations.(c)Meetingsummaries.(5) Reports—publishedandunpublished

factualmaterials.

B. References(1) LaRoe,Winn andMoerman.Counselfor

Aniline Association.Commentsof theAniline Associationon theAdvanceNoticeof ProposedRulemakingon theNeed forAdditionalTestingof Aniline Undersection4ofTSCA. (1984).

(2) Cleary,Gottlieb, SteenandHamilton,Counselfor SubstitutedAnilines TaskForce.Commentson AdvanceNotice ofProposedRulemakingfor Chloro-, Bromo-. and/orNitroanilines,for theSubstitutedAnilinesTaskForceof SyntheticOrganicChemicalManufacturersAssociation.(1984).

(3) SodyecoInc.Commentsof SodyecoInc.on the Advance Notice of ProposedRulemakingon the Needfor AdditionalTestingofAnilines Undersection4 of TSCA.Letterof March 2. 1984 from B.W. Drum toTSCA Public Information Office.

(4) EastmanKodakCompany.CommentsofEastmanKodak on theAdvanceNoticeofProposedRulemakingon the NeedforAdditional Testingof Aniline Undersection4of TSCA. LetterofMarch 2. 1984 from R.F.Brothersto TSCA Public InformationOffIce.

(5) Upjohn Company. Aniline and Chloro-,Bromo- and/or Nitroanilines: Responseto theInteragencyTestingCommitteeby UpjohnCompany. Letter of February28. 1984 fromJ.S. Mehringto TSCA Public InformationOffice.

(8) Cleary, Gottlieb, Steenand Hamilton.Commentson AdvanceNoticeof ProposedRulemakingfor Chioro-,Bromo-. and/orNitroanilines (Appendix A. ConfidentialBusinessInformation)for theSubstitutedAnilines TaskForceof the SyntheticOrganicChemicalManufacturersAssociation~(19841.

(7) LaRne.WinnandMoerman.Commentzof theAniline Associationon theneedforadditionaltestingof aniline undersection4ofTSCA. From:Aniline Association, August26. 1983.

(8) Cleary.Gottlieb.SteenandHamilton.Informationrelevantto EPA’sdeterminationof whetherto requireaddiiional healthorenvironmentaleffectstestingof thesubstitutedaniltnesunder section4 of TSCA.From: SubstitutedAnibnesTaskForceof theSyntheticOrganicChemicalManufacturersAssociation.July 18. 1983. (AppendixA.ConfidentialBusinessInforrnaiion).

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(9) Cleary,Gottlieb. SteenandHamilton,Informationrelevantto EPA’s determinationof whetherto requireadditionalhealthorenvironmentaleffectstestingof thesubstitutedanilinesundersection4 of TSCA.From: SubstitutedAnilines TaskForceof theSyntheticOrganicChemicalManufacturersAssociation.July 18. 1983

(10) SOCMA. SyntheticOrganicChemicalManufacturersAssociation.Letter from A.Rautio of SyntheticOrganicChemicalManufacturersAssociationto M. McCommas,Office of Toxic Substances.USEPA.(ConfidentialBusinessInformation). (1985).

(11) SOCMA. Letter from A. Rautio ofSyntheticOrganicChemicalManufacturersAssociationto M. McCommas.Office ofToxic Substances.USEPA. (1985).

(12) OSHA. OccupationalSafetyandHealthAdministration.OI-IDS-.4HealthSamplingReportfor Aniline (SubstanceCode0220) for PeriodJune1979 throughMay 1983.U.S. Departmentof Labor, Washington.DC.(1983).

(13) OSHA. U.S. Departmentof Labor.‘OccupationalHealthGuidelinesforAniline.” (1978).

(14) ACGIH. American ConferenceofGovernmentalIndustrialHygienists.“TLVs:Thresholdlimit valuesfor chemicalsubstancesandphysicalagentsin the workenvironmentwith intendedchanges.”HygienicGuideSeries:Aniline. (1980).

(15) Monsanto.MonsantoCompany.“Evaluationof blood methemoglobinlevelsfor workers involved in productionof parc-chloroaniline.”Unpublishedcompanydata.(3986).

(16) DuPont.Letter from T. Lewisof DuPontandCompanyto M. McCommas,Office ofToxic Substances,USEPA. (1984).

(17) Ewing.B.B. andChian.E.S.K.“Monitoring to detectpreviouslyunrecognizedpollutantsin surfacewater.”EPA ReportNo. 560/6—77—015performedbyUniversityof Illinois for Office of ToxicSubstances,USEPA.(1977).

(18) )ungclaua.GA.. Lopez-Avila,V.. andHites.R.A. “Organic compoundsin anindustrial wastewater:A casestudyof theirenvironmentalimpact.” EnvironmentalScienceTechnology.32:88—96.(1978).

(19) Games.L.A.. andHites,R.A.,Composition,treatmentefficiency,and

environmentalsignificanceof dyemanufacturingplant effluents.”AnalyticalChemistry.49:1433—1440,(1977).

(20) USEPA. U.S.EnvironmentalProtectionAgency. ‘Retrievalof dataon anilinescategoryfrom EPA’s STORETSystem.”Office of Toxic Substances,USEPA. (1985).

(21) Kirk-Othmer. Northcott, J. “Aniline andits derivatives.’ In: Kirk-Qthrner Encylopediaof ChemicalTechnology.3rd ed. Vol. 2. NewYork: Wiley-Interscience,pp. 309—321. (1978).

(22) Monsanto,“Aqueoussolubility of 4-chloroaniline.” Conductedby MonsantoIndustrialChemicalsCompany,St. Louis.MO. (1982).

(23( Beard. R.R..and Noe. ).T. In: Patty’sIndustrialHygieneand Toxicology.NewYork. NY: JohnWiley andSons,Vol. Ha.(1981).

(24) Konemann.H.. Zelle. R., andBusser,F.‘Determinationof log P valuesof chioro-substitutedbenzenes.toluertes.andanilines

by HPLC on ODS—silica.”JournalofChromatography178:559—565.(1979).

(25) Kenaga.E.E. andGoring. CAl.‘Relationship betweenwatersoluhility. soilsorption,octanol-waterpartitioning, andConcentrationof chemicalsin biota,” ASTI.!SpecialTechnicalPublicationSTP.707:78—115,(1980).

(26) Kenaga.E.E. “Predictedbioconcentrationandsoil sorptioncoefficientsof pesticidesandotherchemicals,”EcotaxicologyandEnvironmentalSafety.4:25—38. (3980).

(27) Bollag, J.M.. Minard, RD., andLiu, S.V.“Cross-linkagebetweenanilinesand phenolichumusconstituents.”EnvironmentalScienceand Technology17:72—80.(1983).

(28) Saxena,A.. andBartha.R. “Binding of3.4-dichioroanilineby humic acid andsoil:mechanismandexchangeability.”SoilScience136(2):l11—116. (1983).

(29) Saxena, A. andBartha.R. “Modelingofthecovalentattachmentof chloroanilineresiduesto quinoidalsitesof soil humus.”Bulletin ofEnvironmentalContaminationToxicology3th485-491.(1983).

(30) Parris,G.E. “Covalent bindingofaromaticaminesto humate.1-Reactionswithcarbonylsandquinones.”EnvironmentalScienceand Technology14:1099—1106.(1980).

(33) You, I—S. Jones,R.A.. andBartha,R.“Evaluationof a chemically definedmodelfor theattachmentof 3,4-dichloroanilinetohumus.”Bulletin of EnvironmentalContaminationToxicology29:476—482.(1982).

(32) Malaney,G.W. “Oxidative abilitiesofaniline-acclimatedactivatedsludge.”Journalof the WaterPollution Control Federation32:1300—1311.(1960).

(33) Pitter, P. “Determinationofbiologicaldegradabilityof organicsubstances.”WaterResearch10:231—235. (1978).

(34) OECDChemicalsTesting Programme—Degradation/AccumulationGroup. “Ring testprogramme1981—1982.Assessmentofbiodegradabilityof chemicalsby manometricrespirometry.”Commissionof theEuropeanCommunitiesreportNo. EUR 8631 EN. (1983).

(35) Lyons, C.D.. Katz. S., andBartha,R.“Mechanismsandpathwaysof anilineelimination from aquaticenvironments.”AppliedandEnvironmentalMicrobiology48:491—496.(1984).

(36) Falco, J.W.,Mulkey, L.A.. and Swank,R.R. “A screeningprocedure for assessingthetransportand degradationof solid wasteconstituentsin sub-surfaceandsurfacewaters.No. 23: Aniline.” Proceedingsof the1st AnnualMeetingfor theSocietyofEnvironmentalToxicologyandChemistry,Washington,DC. (1980).

(37) Rippen.C.. Ilgenstein,M.. Klopffer, W..andPorenski,H.J. “Screeningof theadsorptionbehaviorof new chemicals:Natural soils andmodeladsorbents.”Ecotoxico/ogyandEnvironmentalSafety6:236—245. (1982).

(381 Bordeleau,L.M., andBartha,R.“Biochemical transformationsof herbicide-derivedanilinesin culturemedium and insoil.” CanadianJournalof Microbiology18:1857—1864.(1972).

(39) Bollag, J.M.. Blattman. P.. andLaanio,T. “Adsorptionand transformationof foursubstitutedanilinesin soil:’ Journalof,-tyr/cultural andFoodChemistry.28:1302—1306. (1978).

(40) Kearney.P.C.andPlimmer, JR.“Metabolismof 3,4-dichioroanilinein soils.’Journalof Agriculturaland FoodChemistry20:584—585.(1972).

141) Hsu.T.S. and Bartha, R. “Hydrolyzableandnonhydrolyzable3.4-dichloroanilinehumuscomplexesandtheir respectiveratesof biodegradation.’Journalof Agriculturaland FoodC’hemistry. 24:118—122.(1976).

(42) Freitag,D.. Scheunert.I.. Klein. W . ~ndKorte. F. “Long-term fate of 4-chloroaniline-14C in sodandplantsunderoutdoorconditions.A contributionto terrestrialecotoxicologyof chemicals,”JournalofAgricultural andFoodChemistry.32:203—207(3984).

(43) MillIe, M.J.. andCrosby,0 C.“Pentachiorophenoland3,4-dichloroanilir.casmodelsfor photochemicalreactions nseawater.”Marine Chemistry.14:111—120.(1983).

(44) Miller. CC.. and Crosby,D.C.“Photooxidationof 4-chioroanilineand \.(4chloropheny~-benzenesulfonamideto ni rosaandnitro products.” Chemosphere12)9(.t217—1227. (1983).

(45) Wolff, C.J.M.. and Crossland.N 0.“Fate andeffectsuf 3.4-dichloroaniline ri helaboratoryandin ou~doorionds: I. Fate.’EnvironmentalToxicologyandChernistr;4:481-487,(1985).

(46) Falco,J.W..Mulkey. L.A.. and Swank,R.R. “A screeningprocedurefor assessinghetransportanddegradationof solid wasteconstituentsin sub-surfaceandsurfacewaters: No. 49: Chloroaniline.’ Proceedingsif

the1st AnnualMeetingfor the SocietyofEnvironmentalToxicologyand Chemistry.Washington,DC (1980).

(47) Lyons, C., Bartha,R., andKatz. S.“Chlorine substitutionsandbiodegradabilit.of anilinesin aerobicandanaerobictestsystems.”In: Abstractsof the annualmeetings,New Brunswick,NJ: RutgersUniversity,pp. 271—285. (1983).

(48) Monsanto.“Biodegradationtesting of2-nitroanilineand4-nitro-aniline.”Unpublishedcompanydata.(1975).

(49) Zeyer, J. and Kearney.P. C. “Microbialmetabolismof 14C nitro.anilinesto ~4Ccarbondioxide.”Journalof AgriculturalandFoodChemistry31:304—308. (1983).

(50) Van Alfen, N.K. andKosuge.T.“Microbial metabolismof thefungicide 2.8-dichloro-4-nitroaniline.”JournalofAgricultural andFoodChemistry22:221—224.(1974).

(51) USEPA.“Predictedenvironmentalconcentrationsfor selectedsubstitutedanilines.” ConfidentialBusinessInformation.preparedby M. McCommas,TestRulesDevelopmentBranch, Office of ToxicSubstances.(1985).

(52) USEPA. Memo: SurfaceWaterConcentrationsof Aniline from P. Harrigan.DesignandDevelopmentBranch.Office ofToxic Substancesto M. McCommas,TestRulesDevelopmentBranch,Office of ToxicSubstances.USEPA. ConfidentialBusinessInformation. (1985).

(531 Calamari.0.. Da Casso,F.. Cslsss:.SProvini, A. and Vighi. M. “Biodegradat:unand toxicity of selectedamineaon squstorganisms.”Chemosphere9:733—752 )1Q5(~.

31812 Federal Register / Vol. 53, r’~z~.161 / Friday, August 19, 1988 / Rules and Regulations

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Confid~tialBusinessInformation,while part of the record,is not availablefor p~sblicreview.A public versionofthe record, from whichCBI has beendelete~is availablefor inspectionin theTSCA Public Docket Office, Room. NE—C004.401 M Street~SW., Washington.

31813

DC from 8 am. to 4 p.m..Mondaythrough Friday, exceptlegal holidays.

List of Subjects in 40 CFR Part799

Testing. Hazardoussubstances,Chemicals,Recordkeepingandreportingrequirements.

Dated:August 8.1988.(A. Moore,Assistant,4drninist-at~rfat’ Pest:cidesandToxicSubstances.

Therefore.40 CFR Part 799 isamendedasfollows:

PART 40—4AMENDEDI

1. ‘The authoritycitation continuestoread as follows:

Authority: 15 U.S.C.2603. 2811. 2625.2. Section799.5000is amendedby

addingthe following chemicalsubstancesin ChemicalAbstractService(CAS) RegistryNumber order tothetable,to readas follows:

* 79L5000 Tudn~cons.ntorders.

CAS No. andsubstance~ mcslure Thsang

name

FederatRegisteroration

82-53-3Ans&se ... .~Heattheffects,..

Ertwonmentaieffects.

(meanFRdstet

Do

58-74--4 2- Heatth~tect5... Do.Nitroanitine.

95—51-2 2- Healtheffects... Do.CNoroaMine. Environmental

eftects.Do

95—78-1 3.4- l4eailt, effects... Do.~c8~o~

97-02-9 2,4-. Healtheffects.. Dci,D~nitroanitin.~

99-30-9 2,8’ Et~iconmentai Do.0~o~4-~ ~xaniline.

100-01-8 4. Healtheffects... Do.N~oan~ne.

106-47-a 4- H.~ltheffects.. Do.Ctsloioanilvw.

[FR Doc. 88-18727FlIed 8-13-88:8:45am)SILtiNG COOS 5550—50-s