Document YqaZva70v6NogaEbGgjxG4pV

AbioticDegradationStu and photolysistudypla AbioticDegradation Studiesof PerfluorooctaneSulfonate PurposeofStudy: The purposeofthiisnvestigatiistoondeterminteheabiotidcegradation reactionsr,atesand productsofthepotassiumsaltofperfluorooctanseulfonate (PFOS or FC-95).These resultwsillbe used toaidinthedeterminatioonfthe environmentalfateofthiscompound. Significancoef Study When assessingenvironmentaflateofproductiocnhemistriest,herearefour main factortsakenintoaccount.The firsftactore,nvironmentaelnt[y,considers therateand media intowhichthesubstanceenterstheenvironment.The second factort,ransgb ofthecompound, concernsitsphysicaland chemical propertiessuch as solubilitvya,porpressureand sorptiotnosoiland sediments. These factorsw,hen takentogetherd,etermineitsmovement intheenvironment. Third,the rateoftransformatiodnue toenvironmentadlegradationviabiotiacnd abioticprocessesaretakenintoaccount,and lastsinks,placesinthe environmentwhere thecompound oritstransformedproductcollectsa,re considered.Computer models thencombine theinformatioannd areused to tracethe ratesofmovement, transformatioand distributiaomnong themedia of theenvironmentas a functioonftime.Realworldmeasurements ofthe degradationproductsand manufacturedchemistrieasre conductedand correlatewdithmodels. Onlywithafloftheabove informatiocnan a full environmentalassessment be conducted.The presentstudywillprovide informatioonn abiotidcegradationreactionsr,atesand productsso thatthe assessment willhave increasedreliabilaintdyexposureissueswillbe more completelyresolved. Objectives There are threeprimaryabiotidcegradationprocessintheenvironment: hydrolysisp,hotolysiasnd oxidation/reductiEoanc.h processwillbe studied individualilnycontrolleedxperimentstoidentifdyecompositionproductsand to evaluatethekineticsT.he resultosftheseexperimentsw,hen takenas a whole, willleadtoa more completepicturoeftheabiotidcegradationofPFOS inthe environment. Proposed Degradation Route and Products Itisproposedthatabiotidcegradationmay leadtodirectcleavageoftheC-S bond toproduce a C8Fl7radicalf,ollowedby subsequentrearrangementsto producea varietyofcompounds. Thus,theexpecteddegradationproductsmay includeperfluorooctanoaiccid(PFOA),perfluoronateCda olefinsa,nd mixed Ce hydridesT.histypeofmechanism isunknown inthescientifliicterature. Alternativtehleyremay be productioOfnS02 viaa suffoniitnetermediatTeh.is type ofmechanism isknown inthe literaturfeorboth hydrocarbon based sulfonamideand sulfanatechemistries1.-2This suggeststhatPFOS may undergo abioticdegradation. Protocol GLP Status One goal ofthisstudy isto givefast,accurateand reliabldeata to select members ofthe 3M community and to those individualpserforming environmentalfateand assessment determinations.A second goal isto present the resultsinpeer-reviewedjournalsforbroader distributiaonnd reviewofstudy integrityF.urther,thisdata willbe viewed by variousgovernment entities. However, these studiesare researchand an all-inclusipvreotocolcannot be written.VViththisnotableexception,the studieswillbe conducted incompliance withGLP-type regulations. Adsorption/Desorption Characteristicsand Recoveries A "preliminar"yadsorption/desorptiosntudy,demonstratingacceptable analyterecoveryforboth PFOS and PFOA willbe conducted per OECD Method 106,"Adsorption/Desorptio,,n3.A reportofthe findingswillbe includedinthe final report.Homologues of C8 materialswillbe assumed to behave ina similar manner tothe C8 compounds. Itisassumed thatpossiblevolatildeegradation compounds (e.g.olefinsh,ydddes etc.)willshow littaldesorptiontothe matrixor the container.Degradationproductsnot hereinpredictedwillnot be assessed for adsorption/desorptiopnropertiesifmass balanceforthatportionofthe study isin excess of85%. AnalyticalMethod(s)Validation Analyticamlethods willbe validatedforeach specifictargetmaterialon each piece ofanalyticailnstrumentationT.he methodology formethod validatiownill be includedinthe finalreport. Data Analysis An analysttrainedon softwarespecifitco thatinstrumenton which the data willbe collectedwillperformdata work-up. Kineticdeterminationsq,uantum yields,efficienccyalculationasnd mechanisticelucidatiownillbe performed by the lead investigatoartthe 3M EnvironmentalLaboratory.Alldata willbe reviewed internalliynthe environmentallab,extemallyby Dr.Robert Voyksner at the Research TriangleInstitutaend by Dr.Don Crosby-atthe Univ.ofCaliforni-a Davis. 2 QualitCyontrol An analysiwsilbledeemedacceptabwlheenthefollowiqnugalictoyntrol criteriaare met: The standarddeviationoftriplicaatnealysisislessthan8%. Spiked samples show greaterthan 80% recoveryforalltargetanalytes. Instrumentblanksand qualitycontrolblanksshow lessthan 10% ofthelowest quantitatiolneveldetermined-foerach targetintheanalysis.Curves used for quantationmust have a correlatiocnoefficienotf 0.99orgreater.Residualson the curve are lessthan20%. Internasltandardresponsemust show lessthanan 8% standarddeviation. Sample Purity NMR, GC\MS, HPLCXITMS, HPLCWS\TOFMS, IC\CD and ICP\MS willbe used toanalyzethePFOS used inthisinvestigatifoonrpuritypriorto use. Impuritiecsontainedinthe productionchemistrywillbe monitoredfor degradation.Allchemicalsused inthestudywillbe loggedintotheenvironmental laboratorychemicaltrackindgatabase. Hydrolysis Studies A studyof hydrolytirceactionsleadsto informatioonn thepersistencoefthe parentcompound as wellas informatioonn thestabiliotfypossiblereaction products.Inordertobe representativhey,drolysistudiesshouldbe carriedout atpH valuesnormallyfound intheenvironment(pH 4 to9),and under physiologicaclondition(spH 1 to2).A pH 11.0bufferwillbe added inthepresent studyto betterunderstandthebehaviorofFC-95 inbasicsolutionsT.wo types of solutionswillbe studied.The firssttudywillbe conductedinhomogeneous solutionswhich containonlythefullsyolvatedspeciesina buffer.The methodology forthisportionofthestudyisbased on thatused by the3M EnvironmentalLaboratoryand the U.S.EnvironmentalProtectioAngency4 with the exceptionthata totaolf eightseparatetimepointswillbe collecteodvera seven-week period.The second seriesoftestswillbe conductedinbuffered slurrie(sthreetypesofsoilcorrespondingtothose used inadsorption/desorption studieS3,each in5:1watersoilmixtures).Both serieswillbe runatelevated temperatures(50-70OC). Indilutesolutionst,heratelaw fora hydrolysirseactionisshown by the followinegquations.Itisimportantto notethatthe equationsmust be modifiedin solutionsthatare notdilute. -d(PFOS) d(t) khyd( PFOS) or (PFOS)T In = (PFOS)O 3 -k t hyd The half-lioffethe compound at a specificpH isrelatedto the rateofhydrolysis by: (0.693) tl/2 k Using the equationsabove, the concentratioonf PFOS inthe aqueous buffer-,, willbe monitoredto calculatethe hydrolysisrateconstantand half-lifIefa.ny loss of FC-95 isobserved the degradationproductswillbe determined.Ifthe calculatedhalf-liifselessthan fiveyears,a second study willbe initiateodver' multipletemperaturesand multiplepH's to determinethe kineticorderand rateof reaction. Aqueous samples willbe prepared inbuffersolutionsof pH = 1.5,5.0,7.0, 9.0,and 11.0accordi'n:gtopublishedEPA guidelinesT.he buffersselectedwillbe those publishedby EPA method, or used because they are acceptablebuffersfor HPLC/MS analysis.Five-mlaliquotsof PFOS atca. 2.00 @tg/miinaqueous buffer willbe added to40 mi VOA vials.One setofsamples foreach time pointand each pH willbe placed insidean orbitaslhaker held ata constanttemperatureof 500C. These willbe prepared intriplicawtiethone additionarleplicatfeorspike recoverydata. One setofblanks,containingonlythe bufferateach pH and for time point,butwithoutPFOS, willalso be includedforqualitycontrolA.t selected time intervalsa,setofsample vialswillbe pulledforanalysis.The samples will be dilutedwitheitherisopropylalcoholor methanol containinga suitableint' ernal standard,and analyzedby HPLC/MS forPFOS concentration. Slurrysamples willbe preparedby firswteftingeach ofthe threedriedand characterizedsoilswith0.01 M CaC12 (1:10soilto CaC12) in40 ml VOA vialsfor at least24 hours atroom temperature. Followingthis,the liquiwdillbe pored off and a volume ofbuffer(pH = 1.5,5.0,7.0,9.0,and 11.0)equal tothe amount of CaC12 removed willbe added. A 10 pL spikeof PFOS willthen be added ata predeterminedconcentrationsufficientto givea ca.2.00 pg/ml concentrationin aqueous buffer.One setof samples foreach time pointand each pH willbe placed insidean orbitaslhaker held ata constanttemperatureof500C. These willbe prepared intriplicawtieth one additionarleplicatfeorspikerecoverydata. One setofblanks,containingonlythe bufferedslurryateach pH and fortime point,,buwtithoutPFOS, willalsobe includedforqualitycontrolA.t selectedtime intervalsa,setofsample vialswillbe pulledforanalysis.The samples willbe dilutedwitheitherisopropylalcoholor methanol containinga suitableinternal standard,centrifugedand analyzed by HPLC/MS forPFOS concentration. The solventschosen fordilutioannd preparationof reagents(IPAand methanol,respectivelya)re water-solublesolventsinwhich the subjectmaterial being analyzedissoluble.Solutionswillbe degassed priortosample preparationB.iodegradationofthe analyteby microbialgrowth inthe buffered media should be excluded because ofthe study being conducted at 500C, a 4 temperaturethatisforbiddingformost mesophillicmicroorganisms (thetype found inlaboratorsyettings). IndirectPhotolysisStudies Due tominimallighatbsorptioninthe UV/visregionby many 3M fluorochemicalst,heindirecmtechanism ofphotolytidcecompositionwillbe studied.5-T8he indirecmtechanism can be definedas a chemicalor electronic excitatiotnransfefrrom a lighatbsorbingspeciesto thetargetspecieswhich inducessome typeofchemicalchange. Inthesestudiesp,hotonsfrom thelight sourcewillbe used to inducedtheformationofradicalfsrom hydrogen peroxide containedinthesolution.10-T1h6ese radicalsinturnreactedwiththe fluorochemicaltso produce thechemicalchanges discussedbelow. PFOS willbe exposed to simulatedsunlightinincreasinglmyore "dirtyo"r complex environments[waterspikedwithhydrogen peroxide,synthetihcumic water,naturallakewaterand soilslurrie(sthreetypesofsoil)T]h.ese exposures willtesthow each environmentaffectsthephotolytimcechanism. Achievingnear mass balanceby accountingforallparentand productspeciesisa necessary goal,so thatmeaningfulcomparisons between the resultsofeach photolytic exposure can be assessed. Itisexpected thatadsorptionofbothparentand productspeciesto particulataensd organicmaterialswillinducechanges inthe photo.lytbiechavioroverthepure water system. However, what theseeffectswill be ishighlyspeculative. Samples forthepurewater portionofthisinvestigatiwoinllbe preparedas follows.Fivetotwentyml aliquotosf PFOS inwat'erata concentratioonfca.2.0 [Lglmlwillbe added to40 mi VOA vialsand spikedwith10 gL of a 30% H202 solutioninwater.Four setsof samples foreach time pointwillbe preparedin triplicawtiethtwo additionarleplicatefsorspikerecoverydata. Two setswillbe exposed to thelighstource,theothertwo willbe keptdarkbutheldatthesame temperature.Four setsofblanks,containingonlytheanalytebutwithoutthe H202willbe setup foreach timepoint.Again,two setswillbe exposed tothe lighstource;thetwo otherwillbe keptdark butheldatthesame temperature. Four setsof blanks,containingthe H202but withouttheanalytewillbe setup for each time point.Two sets willbe exposed tothe lightsource,the othertwo will be keptdarkbutheldatthesame temperatureT.he vialwsilble inverteadnd placedina customdesignedliquicdoolingbathcontaineidnthetestchamber of an AtlasSuntestCPS Pluslighsttabilicthyamber. A xenon-arclamp (simulated sunlightw)itha 330 nm - 800 nm notchfiltewrillbe turnedon foran exposure timeof68 -72 hourswiththe H202solutionbeingspikedineach appropriatveial at24 hour intervalsL.ightintensitwyillbe recordedusinga commercial radiometerinterfacetdo a personalcomputer.Samples willthenremoved and dividedforanalysisby dynamic purge and trapgas chromatography/mass spectrometry(GC/MS) forvolatildeegradationproducts.High performanceliquid chromatography/massspectrometry(HPLC/MS) willbe used fornon-volatialned 5 semi-volatialnealysis.Ionchromatography/conductividteytection(IC/CD)willbe used forsulfites,ulfates,ulfonamidiaccid,trifluoroaceatciicdand freefluoride analysis. Samples willbe preparedas followsforthesynthetichumic water portionof theinvestigatioSny.nthetichumic water willbe preparedas per EPA procedure.17 Fivetotwentymi aliquotosf PFOS insynthetichilmicwater ata concentrationofca.2.0@tg/miwillbe added to40 ml VOA. Four setsofsamples foreach timepointwillbe preparedintriplicawtiethtwo additionarleplicatefsor spikerecoverydata.Two setswillbe exposed to thelighstourcewhiletheother two willbe keptdarkbutheldatthesame temperature.Four setsof blanks, containingonlytheanalytebutwithoutthe synthetichumic water willbe setup foreach timepoint.Again,two setswillbe exposed to thelighstource;the two otherwillbe keptdark butheldatthesame temperature.Four setsofblanks, containingonlythesynthetihcumic water butwithouttheanalytewillbe setup foreach timepoint.Two setswillbe exposed tothe lighstource,theothertwo willbe keptdarkbutheldatthesame temperature.The vialswillbe invertedand placedina custom designedliquicdoolingbath containedinthetestchamber of a AtlasSuntestCPS Pluslighsttabilicthyamber. A xenon-arclamp (simulated sunlightw)itha 330 nm - 800 nm notchfiltewrillbe turnedon foran exposure timeof68 -71hours. Lightintensitwyillbe recordedusinga commerciallybuilt radiometerinterfacetdo a personalcomputer. Samples willthen removed and analyzedby dynamic purge and trapgas chromatography/mass spectrometry (GC/MS) forvolatildeegradationproducts.High performanceliquid chromatography/massspectrometry(HPLC/MS) willbe used fornon-volatilaend semi-volatialnealysis.Ionchromatography/conductividteytection(IC/CD)willbe used forsulfitseu,lfates,ulfonamidiaccid,trifluoroaceatciicdand freefluoride analysis. Samples forthelakewater portionofthisinvestigatiwoinllbe preparedas follows.Fivetotwentyml aliquotosfPFOS inlakewaterata concentratioonf ca.2.0gg/mlwillbe added to40 ml VOA vialsF.our setsofsamples foreach timepointwillbe preparedintriplicawtiethtwo additionarleplicatefsorspike recoverydata.Two setswillbe exposed t-othe lighstource,theothertwo willbe keptdark butheldatthesame temperature.Four setsof blanks,containingonly the analytewillbe setup foreach timepoint.Again,two setswillbe exposed to the lighstource;thetwo otherwillbe keptdark butheldatthesame temperature. Foursetsofblanksc,ontainitnhgelakewaterbutwithouttheanalytweilble set up foreach timepoint.Two setswillbe exposed tothelightsource,the other two willbe keptdarkbutheldatthesame temperature.The vialswillbe inverted and placedina custom designedliquicdoolingbath containedinthetest chamber ofa AtlasSuntestCPS Plus lighsttabilicthyamber. A xenon-arclamp (simulatedsunlightw)itha 330 nm - 800 nm notchfiltewrillbe turnedon foran exposure timeof68 -72 hours.Lightintensitwyillbe recordedusinga commercialradiometerinterfacetdo a personalcomputer.Samples willthen removed and analyzedby dynamic purge and trapgas chromatography/mass 6 spectrometry(GCIMS) forvolatildeegradationproducts.High performanceliquid chromatography/massspectrometry(HPLC/MS) willbe used fornon-volatilaend semi-volatia(nealysis.Ionchromatography/conductivdiettyection(IC/CD)wilble used forsulfites,ulfates,ulfonamidiaccid,trifluoroaceatciicdand freefluoride analysis. Slurrysamples willbe preparedby firswteftingeach ofthethreedriedand characterizesdoilswith0.01 M CaC12 (1:10 soiltoCaC12)in40 mi VOA vialsfor atleast24 hoursatroom temperature.Followingthist,he liquiwdillbe pored off and a volume ofwaterequaltotheamount ofCaC12 removed willbe added.A 10 liLspikeof PFOS willthen be added ata predeterminedconcentratiosnufficient to givea ca.2.00@Lg/miconcentrationinwater. The vialswillthen be spikedwith 10 @LLof a 30% H202solutioninwater.Foursetsofsamples foreach timepoint willbe prepared intriplicawtiethtwo additionarleplicatefsorspikerecoverydata. Two setswillbe expo16dtothe lightsource,the othertwo willbe keptdarkbut heldat thesame temperature.Four setsofblanks,containingonlytheanalyte willbe setup foreach timepoint.Again,two setswillbe exposed tothe light source;thetwo otherwillbe keptdark butheldatthesame temperature.Four setsofblanks,containingonlythesoilswillbe setup foreach timepoint.Again, two setswillbe exposed tothe lighstource;thetwo otherwillbe keptdarkbut heldatthesame temperature.Four setsofblanks,containingonlywaterwillbe setup foreach timepoint.Two setswillbe exposed tothelighstource,the other two willbe keptdark butheldatthesame temperature.The vialswillbe inverted and placedina custom designed liquicdoolingbathcontainedinthetest , chamber of a AtlasSuntestCPS Plus lighsttabilicthyamber. A xenon-arclamp (simulatedsunlightw)itha 330 nm - 800 nm notchfiltewrillbe turnedon foran exposure timeof68 -72 hours. Samples, blanksa'nd controlswillbe spikedwith an additiona1l0 @tLaliquotofa 30% H202solutioninwater where app ropfiate every 24 hours.Lightintensitwyillbe recordedusinga commercialradiometer interfacetdo a personalcomputer.Samples willthen removed and analyzedby dynamic purge and trapgas chromatography/massspectrometry(GC/MS) for volatildeegradationproducts.The samples fornon-volatilaenalysiswillbe dilutedwitheitherisopropyallcoholor methanol containinga suitablienternal standard,centrifugeadnd analyzedby highperformanceliquicdhromatography/ mass spectrometry(HPLC/MS). Ionchromatography/conductividteytection (IC/CD)willbe used forsulfitseu,lfates,ulfonamidiaccid,trifluoroaceatciicdand freefluoridaenalysis. Oxidation/ReductionStudies Oxidation/reductimoenchanisms are wellknown tooccur intheabiotic degradationof many classesof compounds. 18-21 Thisinvestigatiwoinllfocuson one specifitcype-oxidationby ferriocxide,a reactionwellknown tooccur in naturalsystems. Thisreactionhas been shown to occur inboththepresence and absence ofsunligh(tcatalytoixcidatioannd indirecpthotolysis2)2-.23 Observationsfrom theseexperimentsmay helpinelucidatioonf resultfsrom both 7 hydrolytiacnd photolytisclurrystudies,as the variousoxides may be presentin differincgoncentrationsinthe soils.Oxidationby T102 under the same conditionswillserve as a controlexperiment.24-27 Samples forthisportionofthe investigatiownillbe prepared as follows.Five totwenty ml aliquotsofPFOS inwater ata concentrationofca. 10.0@Lg/miand a metal oxide concentrationof 100 gg/ml willbe added to40 ml VOA vials.This givesapproximately50:1 molar excess of metal oxidestoensure sufficient concentrationto induceany possibleabioticdegradation.One-halfofthe vials willbe spiked with 10 gL ofa 30% H202 solutioninwater. Sixteensets of samples foreach time pointwillbe prepared intriplicawtiethtwo additional replicatefsorspikerecoverydata (eightwiththe ironoxides,fourofwhich will have H202 added and eightwithTi02, fourofwhich willhave H202 added). Eight setswillbe exposed tothe lightsource,the othereightwillbe kept dark but held atthe same temperatute.Sixteensetsof blanks,containingthe H202 and metal oxide withoutthe analytewillbe set up foreach bme point(eightwiththe iron oxides,fourofwhich willhave H202 added and eightwithTi02, fourofwhich will have H202 added). Eightsetswillbe exposed tothe lighstource,the othereight willbe kept dark butheldatthe same temperature.The vialswillbe invertedand placed ina custom designed liquidcoolingbath containedinthe testchamber of a AtlasSuntestCPS Plus lightstabilicthyamber. A xenon-arclamp (simulated sunlightw)itha 330 nm - 800 nm notchfiltewrillbe turnedon foran exposure time of 160-168 hourswiththe H202 solutionbeingspikedinthe appropriatevials at24 hour intervalL.ightintensitwyillbe recordedusinga commercial radiometerinterfacetdoa personalcomputer.Samples willthen be removed and analyzed by dynamic purge and trapgas chromatography/mass spectrometry (GC/MS) forvolatildeegradationproducts.High performanceliquid chromatography/mass spectrometry(HPLC/MS) willbe used forno.n-volatialned semi-volatilaenalysis.Ionchromatography/conductivitdyetection(IC/CD)willbe used forsulfites,ulfates,ulfonamidicacid,tdfluoroacetaicid and freefluoride analysis. Timeline The study willbe conducted inthe 3M EnvironmentalLaboratory.Select portionsofthisinvestigatiohnave been carriedout,althougha complete data and kineticwork up has not been finishedor reviewed. Each major portionofthe investigatiownillhave an individuaplreliminaryreportissued. A finalreport, which willtiethe separateportionstogether,willbe issuedpriorto September 1, 2000. References: 1. Art,J.F.;Kestermont,J.P.;SoumillionJ,.P. Photodetosylationof Sulfonamides Initiatebdy ElectronTransferfrom an Anionic Sensitizer.TetrahedronLettersV.olume 32,Number 11,Pages 1425-1428, 1991. 2. Arnould,J.C.;Cossy, J.;P&te,J.P. Photolysisof 2(N-Alkyl-Arylsulfonylamido) Cyclohexenone and Unusual and UsefulDesulfonation Reaction.TetrahedronLettersN.umber 43,Pages 3919-3922,1976. 3. OrganizationforEconomic and CooperativeDevelopment (OECD) GuidelineforTestingofChemicals,Number 106,Adsorption/Desorption, 1981. 4. United States EnvironmentalProtectionAgency. OPPTS 835.2110 Hydrolysis as a Function of pH. Prevention,Pesticidesand Toxic Substances: Fate,Transportand TransformationTestGuidelines.EPA 712C-98-057, Pages 1-16,1998. 5. Lunak, S.;Sediak,P. PhotoinitiatedReactions of Hydrogen-Peroxide in the Liquid-Phase. Joumal ofPhotochemistryand PhotobiologyA Chemistry.Volume 68, Number 1,Pages 1-33,1992. 6. Haag, W. R.;Hoigne,J. Photo-SensitizedOxidation inNatural-Watervia OH- Radicals. Chemoshpere. Volume 14, Number 11-1,Pages 16591671,1985. 7. Ruzo, L.0.;Casida,J.E. Photochemistry of Thlocarbamate HerbicidesOxidativeand Free-RadicalProcesses of Thlobencarb and Diallate. Joumal ofAgriculturalnd Food Chemistry.Volume 33,Number 2, Pages 272-276, 1989. 8. Draper,W.M.; Crosby,D.G. Hydrogen-Peroxide and Hydroxyl Radical Intermediatesin IndirectPhotolysis Reactions inWater. Joumal of Agriculturaalnd Food Chemistry.Volume 29, Number 4, Pages 699-702, 1981. 9. Lunak, S;Sediak,P. Photoinitiaterdeactionsof hydrogen peroxide in the liquidphase. J.Photochem. PhotobiolA.: Chem. Volume 68, Number 1,Pages 1-33,1992. 10. Armbrust,K.L. Photochemical Processes InfluencingPesticide Degradation inRice Paddles. Joumal ofPesticideScience.Volume 24, 9 Number 1,Pages 69-73, 1999. 11. Draper,W.M.; Crosby,D.G. Photochemistry and Volatilitoyf Drepamon inWater. Joumal ofAgriculturalnd Food Chemistfy.Volume 32,Number 4, Pages 728-733, 1984. 12. Draper,W.M.; Crosby,D.G. So!arPhotooxidation of Pesticidesin Dilute Hydrogen Peroxide.JournalofAgriculturaalnd Food Chemistry.Volume 32, Number 2, Pages231-237, 1984. 13. Draper,W.M.; Crosby, D.G. PestL*IciPdheotodecomposition in Dilute Hydrogen Peroxide Solution. 17e Ameiican Chemical SocietyNational Meeting,1978. 14. Benitez,F. J.;B61tranherediaJ,.;Gonzalez, T.;Real,F. Photooxidation of Carbofuran by a Polychromatic UV Irradiatiownithoutand with Hydrogen-Peroxide. Industrianld EngineetingChemistryResearch. Volume 34,Number 11,Pages 4099-4105,1995. 15. Mabury, S. A.;Crosby,D.G. PesticideReactivityToward Hydroxyl and itsRelationshipto FieldPersistence.Joumal ofagdgculturaland Food Chemistry.Volume 44, Number 7,Pages 1920-1924,1996. 16. Aires,P.;Gal, E.;Chamarro, E.;Esplugas,S. Photochemical Degradation of Malathion inAqueous-Solutions. Joumal of Photochemistryand PhotobiologyA-Chemistiy. Volume 68, Number 1, Pages 121-129,1992. 17. UnitedStatesEnvironmentalProtectionAgency. OPPTS 835.5170 Indirect PhotolysisScreening Test.Prevention,Pesticidesand ToxicSubstances: Tate,Transportand Transfoi7natioTnest Guidelines.EPA 712-C-98-099, Pages 1-16, 1998. 18. Pankratov, A. Khim. Vys. Energ. Volume 4, Pages 126-, 1970. 19. Shub, D; Tyurikov, G.; Veselovskii,V. Zh. Fiz.Khim. Volume 34, Pages 2245-,1960. 20. Sviridov,V.; Schevchenko, G. Vestn.Beloruss.Univ. Volume 2, Pages 13,1969. 21. Chang, I.;Zaleiko,N. Proc. 36th IndustrialWaste Conf, Purdue, IN. Pages 814-,1981. 22. Behar, B; Stein,G. Science. Volume 154, Pages 1012-, 1966. 10 23. KoziovJ,.;NadhezdinA,.;PurmalA,. IntJ.Chem.KinetVolume6,Pages 383-,1974. 24. Augugliaro,V.;Davi,E.;Paimisano,L;Schiavello,M; SclafaniA,. Appl. CataL Volume 65, Pages 101-, 1990. 25. Salvader,P.;Gutierrez,C. J.Phys. Chem. Volume 88, Pages 3696-,.198& 26. Salvader,P. J.Phys. Chem. Volume 89, Pages 3863-, 1989. 27. Gutierrez,C; Salvader,P. J.Electrochem.Soc. Volume 133, Pages 924-, 1986. STABILITY IN WATER TEST SUBSTANCE Identity:Perfluorooctanesulfonamtaey; alsobe referredtoas PFOS or FC-95. (1-Octanesulfoniacid,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8heptadecafluoro-p,otassiumsalt,CAS 2795-39-3) Remarks: Testingisinprogress.