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1、附录己外文文献及其译文外文文献：RemovalofPharmaceuticalsduringDrinkingWaterTreatmentTheeliminationofselectedpharmaceuticals(bezafibrate,clofibricacid,carbamazepine,diclofenac)duringdrinkingwatertreatmentprocesseswasinvestigatedatlabandpilotscaleandinrealwaterworks.Nosignificantremovalofpharmaceuticalswasobservedinb
2、atchexperimentswithsandundernaturalaerobicandanoxicconditions,thusindicatinglowsorptionpropertiesandhighpersistencewithnonadaptedmicroorganisms.TheseresultswereunderscoredbythepresenceofcarbamazepineinbankfiItratedwaterwithanaerobicconditionsinawaterworksarea.Flocculationusingiron(lll)chlorideinlab-
3、scaleexperiments(Jartest)andinvestigationsinwaterworksexhibitednosignificanteliminationoftheselectedtargetpharmaceuticals.However,ozonationwasinsomecasesveryeffectiveineliminatingthesepolarcompounds.Inlabscaleexperiments,0.5mg/Lozonewasshowntoreducetheconcentrationsofdiclofenacandcarbamazepinebymore
4、than90%,whilebezafibratewaseliminatedby50%witha1.5mg/Lozonedose.Clofibricacidwasstableevenat3mg/Lozone.Underwaterworksconditions,similarremovalefficiencieswereobserved.Inadditiontoozonation,filtrationwithgranularactivatedcarbon(GAC)wasveryeffectiveinremovingpharmaceuticals.Exceptforclofibricacid,GAC
5、inpilot-scaleexperimentsandwaterworksprovidedamajoreliminationofthepharmaceuticalsunderinvestigation.IntroductionInGermany,somepharmaceuticalsareusedinquantitiesofmorethan100t/yr(1).Pharmacokineticstudiesexhibitthatanappreciableproportionoftheadministeredpharmaceuticalsareexcretedviafecesandurine(2)
6、andthusarepresentinthedomesticwastewater.Afurthersourceforthecontaminationofwastewaterisassumedtobethedisposalof(expired)medicineviatoilets.However,thisportionisverydifficulttoestimatebecausereliabledataarenotavailable.Afterpassingthroughsewagetreatmentplants(STPs),pharmaceuticalresiduesenterreceivi
7、ngwaters.Pointdischargesfrompharmaceuticalmanufacturerscanalsocontributetocontaminationofriversandcreeks(3).Firstresultsconcerningenvironmentaloccurrenceofpharma-ceuticalsarereportedbyGarrisonetal.(4)andHigniteandAzarnoff(5),whodetectedclofibricacidinthelowermicrogramsperliterrangeintreatedsewageint
8、heUnitedStates.Furtherstudiesin1981inGreatBritainrevealedthatpharmaceuticalsarepresentinriversupto1ig/L(6).OnIonaIsland(Vancouver,Canada)Rogersetal.(7)identifiedthetwoantiphlogisticsibuprofenandnaproxeninwaste-water.Recentinvestigationsshowedtheexposureofawiderangeofpharmaceuticalsfrommanymedicinalc
9、lasses(e.g,betablockers,Sympathomimetics,antiphlogistics,lipidregulators,antiepileptics,antibiotics,vasodilators)toriversandcreeks.ReviewsfromHalling-SOrensenetal.(8),DaughtonandTemes(9),andJOrgensenetal.(10)summarizemostoftheliteratureinthisnewemergingfieldabouttheenviron-mentalrelevanceofpharmaceu
10、ticals.Furthermore,Mohleetal.(11),Alderetal.(12),Temesetal.(3),andZuccatoetal.(13)havereportedtheidentificationofpharmaceuticalsintheaquaticenvironment.Contaminationisinfluencedbytherelativeportionsofrawandtreatedwastewater(14)suchthatevensmallriversandcreekscanbehighlycontaminated.Groundwateriscont
11、aminatedwithpharmaceuticalsprimarilybyinfiltrationofsurfacewatercontainingpharmaceuticalresiduesaswellasbyleaksinlandfillsitesandsewerdrains.Becauseofthewidespreadoccurrenceofpharmaceuticalsintheaquaticenvironmentandsometimesalsointherawwaterofwaterworks,afewcasessurfacedwherepharmaceuticalsweredete
12、ctedindrinkingwaterinthelowernanogramsperliterrange(15,16).Althoughuptonownoadversehealtheffectscanbeattributedtotheconsumptionofpharmaceuticalsattheselowconcentrationlevels,basedonprecautionaryprinciples,drinkingwatershouldbefreeofsuchanthro-pogeniccontaminants.Currently,fewpapershavebeenpublishedd
13、ealingwiththeremovalofpharmaceuticalsindrinkingwatertreatment.Ozonationandespeciallyadvancedoxidationprocessesseemtobeveryeffectiveinremovalofdiclofenac,whileclofibricacidandibuprofenwereoxidizedinlab-scaleexperimentsmainlybyozoneH2O2asshownbyZwienerandFrimmel(17).Hebereretal.(18)exhibitedthatrevers
14、eosmosisisappropriatetoremoveavarietyofdifferentpharmaceuticalsfromhighlycontaminatedsurfacewaters.Theobjectiveoftheworkpresentedherewastostudytheefficiencyofdifferenttreatmentstepstoremovetheanti-phlogisticdiclofenac,theantiepilepticcarbamazepine,andthelipidregulatorsclofibricacidandbezafibrateduri
15、ngdrinkingwatertreatment.Therefore,theprimaryeliminationoftheselectedpharmaceuticalswasinvestigatedunderlaboratory,pilot,andrealwaterworksconditions.Inadditiontoprocessessuchasbankfiltrationandartificialgroundwaterrecharge,widelyusedtechniquesforsurfacewatertreatmentsuchasactivatedcarbonfiltration,o
16、zonation,andfloccula-tionwereinvestigated.ThemonitoringresultsoftwoGermanwaterworksareextendedbylab-andpilot-scaleexperimentstoobtainmoregeneralizedresults.ExperimentalSectionSelectedpharmaceuticals.Foralllab-andpilot-scalespikingexperiments,fourrelevantpharmaceuticals(theantiphlo-gisticdiclofenac,t
17、heantiepilepticcarbamazepine,thelipidregulatorsclofibricacidandbezafibrate)havebeenselectedastargetcompounds.TheirmolecularstructuresareshowninTable1.ThesecompoundshavebeenchosenbecauseoftheirpredominantoccurrenceinGermanfeedingwatersforwaterworkssuchasrivers,bankfiltrates,andground-water(14,19).Add
18、itionally,theantiepilepticprimidonewasincludedinoxidationexperimentsandawaterworkssurvey.Primidone144-LI-6andepilepticTABLELSeIeCtedTargetPharmaCeUtiCaISNameCAS-numberChcmiculstructureAppJicationClofibrieacid4LS5M7-08睫-09-7crJJlipidr霏ImotITicLaboIiIcoflipidicgularorsclcfibrate.erofibme,theofibrateDk
19、kfenacCarbamazepine15307-86525M5-4HODt.1rfaniipMogiMKantiepilepticAnalyticalMethods.Thedeterminationofthepharma-ceuticalswasperformedusingdifferentanalyticalmethods(seeTable2).Allmethodswerebasedonasolid-phaseextractionoftheanalytesontoRP-CisorLichroluteENmaterial.Aftersolid-phaseextraction(SPE)anda
20、nelutionstepwithmethanoloracetone,thecompoundswerederivatizedusingdifferentagents.Eitheramethylationwithdiazomethane(20)oraSilylationwithamixtureofN,O-bis(trimethylsilyl)acetamide(BSA)and5%trimethylchlo-rosilane(TMCS)(Fa.Fluka,Buchs,Schweiz)wereused(60minat120oC)(21).Carbamazepinewasdeterminedafters
21、ilylationeitherbyamixtureofMSTFATMSIDTE(N-methyl-N-(trimethylsilyl)trifluoroacetamide/trimethylsilylim-idazol/dithioerytrit;1000iL/2yfZ2ig)(22)orbyamixtureofBSA/TMCS.Forprimidone,anacetylationbyacetanhy-drideandethanolaminewasused(22).Inallcases,GC-MSwasusedforthedetectionoftheanalytes.Furtherdetail
22、softhemethodsarereportedinrefs19-22.Allmethodsenabletheprecisedeterminationofthetargetpharmaceuticalsinriverwateranddrinkingwater.Aninterlaboratorycomparisonexercise(ICE)betweenthethreeparticipatinglaboratoriesatthebeginningandtheendofthestudyconfirmedthequalityoftheanalyticalmethods.Groundwaterands
23、urfacewatersampleswerespikedwiththeselectedpharmaceuticalsandanalyzedbyallthreelaboratoriestoconfirmtherecoveriesoftheanalytesintherespectivematrixes.Themeanrecoveryofthespikedconcentrationsalwaysexceeded70%throughdifferentspikingIeVelS:0.40-0.90ig/Linsurfacewaterand0.030-0.20ig/Lindrinkingwater.The
24、relativestandarddeviationsbetweenthethreeparticipatinglaboratorieswereingeneralbelow25%.Thus,itcouldbeshownthat(i)thedifferenceoffoundconcentrationswasminorbetweentheIhreelaboratoriesand(ii)thespikedconcentrationcouldbedetectedinthegroundwaterandsurfacewateraccuratel.1.imitsofQuantification(LOQ)andC
25、alibration.TheLOQwascalculatedaccordingtotheGermanDIN32645(23)withaconfidenceintervalof99%usingthestandarddeviationofalinearregressioncurve.Calibrationrangesfrom0.005to0.050ig/Landfrom0.05to1ig/Lwereusedwithatleastsevenconcentrationlevelsbyspikinggroundwater.LOQisanothertermforlimitofdetermination(L
26、OD)mentionedinDIN32645.SincethecalculatedLOQvalueswerealwaysbetweenthefirstandthesecondcalibrationpoints,theLOQusedwassetasthesecondlowestcalibrationpointofthelinearcorrelationtoensureaprecisequantification.Hence,theLOQwereatleast20ng/Lfordiclofenac,carbamazepine,primidone,andclofibricacidanddownto5
27、0ng/Lforbezafibrate.However,withafinalvolumeof100亿insteadof1mL,LOQdownto2ng/Lwereachievedforclofibricacid,primidone,diclofenac,andcarbamazepineanddownto10ng/Lforbezafibrate.Thecalibrationwasperformedoverthewholeprocedureafterspikinggroundwaterwiththestandardmixtureoftheselectedpharmaceuticals.Thecal
28、culationoftheconcentrationsinnativesampleswascarriedoutusingsurrogatestandards(seeTable2)andalinear7-10pointcalibrationcurve.ReferenceStandards.Thereferencestandardsclofibricacid,bezafibrate,carbamazepine,diclofenac,andprimidoneaswellasthesurrogatestandardsmeclofenamicacidand2,3-dichlorophenoxyaceti
29、cacid(2,3-D)werepurchasedfromSigma,Germany;dihydrocarbamazepinewaspurchasedfromAlltech,Germany.Allstandardsweredissolvedinmethanol(1mgmL)anddilutedwithmethanoltothefinalstocksolutionof10igmL.TreatmentProcessesUsedinWaterworks.(a)StudyofBiodegradationinBatchExperimentswithNativeSurfaceWater,Groundwat
30、er,andDifferentFilterMaterials.Bio-degradationisoneofthecrucialfactorsthatdeterminetheeliminationoforganiccompoundsduringartificialground-waterrechargeandbankfiltration.Toassessthegeneralbiodegradabilityofpharmaceuticalsinaquaticenvironmentalmatrixes,batchexperimentswerecarriedoutaccordingtotheOECDg
31、uidelinesfortestingchemicals(24).Theinoc-culumusedconsistedof400mLofsurfacewaterand400mLofgroundwatermixedwith2LofMITIbasalmedium.TheMITIbasalmediumwaspreparedbymixing1Lofsteriledeionizedwaterwith3mLofsterilizedsolutionsA-D.SolutionAwasasolutionof21.75gofK2HPO4,8.5gofKH2PO4,44.6gofNa2HpO4A12H2O,and1
32、.7gofNH4C1ini000mLofdeionizedwateratpH7.2.SolutionsB-Dweresolutionsof22.5gofMgSO4A7H2O,27.5gofCaC12,and0.25gofFeCh,respectively,in1000mLofdeionizedwater.ThegroundwaterwastakenfromaGermanwatercatchmentareawithartificialgroundwaterrechargeusingslowsandfiltrationandbankfiltration.Theindividualconcentra
33、tionsofbezafibrate,carbamazepine,clofibricacid,diclofenac,andibuprofenwereinthebatchexperimentsadjustedto0.1and100ig/L.Thebatchexperimentswereexposedtoeitherindividualoramixtureoftheselectedpharmaceuticals.Instocksolutionswithethanol,theconcentrationsofthetestedpharmaceuticalswere0.5mg/mLor0.5igmL,r
34、espectively.Afterbeingdiluted(480Lofstocksolutionin2.4Lofculturesolution),theconcentrationofethanolinbatchcultureswas0.02%(v:v).Thecultureswerealwaysincubatedinthedarkfor28dat14(insitutemperature).Foranoxicconditions,25mg/Lnitratewasaddedasanalternativeelectronacceptor.Thebottlesusedweregastight.For
35、aerobicsorptionexperi-ments,400gofsandor400gofgraveltakenfromtheundergroundofagroundwatercatchmentareawasusedasinocculumandmixedwith2LofMITIbasalmedium(solidphase/liquidphase)1:5).Sandthatisalsousedfortheslowsandfiltersofawaterworksconsistsofameangrainsizerangeof0.2-0.6mm.Thisfiltermaterialshowedamo
36、deratepermeabilitywithaK/coefficientof4.3IO4ms.Thegravel(naturalaquifersediment)wasveryheterogeneouswithapredominantfractionof2-10mmgrainsizeandaKjcoefficientof2.9103ms.Sterilecontrols(sterilizationfor1h)werepreparedtodifferentiatebetweensorptionandmicrobialdegradation.Thesandcontains3.2mg/gironand0
37、.056mg/gmanganese.Coatingswithironandmanganesehydroxidesweredetectedinthegravelbutwerenotquanti-fied.Esteraseactivitiesweremeasuredtocontrolthephysi-ologicalstatusofmicrobialcommunitiesduringtheincuba-tionofbatchcultures.Thehydrolysisoffluoresceindiacetate(FDA)byesteraseenzymeswasdeterminedaccording
38、totheprocedureofSchnurerandRosswall(25).A20-iLvolumeofFDAsolution(20mg/10mLacetone,storedat-18)wasmixedwith3mLofsampleand0.5mLofHEPESbuffer(0.1MN-2-Hydroxyethylpiperazine-NC-2-ethansulfonicacidso-diumsaltindeionizedwater,adjustedtopH7.5;Merck).Afterbeingincubated(sterileconditions,90minat20oC,darkne
39、ss),thefluoresceinformationwasimmediatelymea-suredwithaPerkin-ElmerfluorescencespectrometerLC(excitationat480nm,emissionat505nm).(b)Flocculation.ForflocculationexperimentsinIab-Scaleexperiments,anoncontinualprocedure,theso-calledJartest1*,wasperformed.Spikingconcentrations,stirringvandreactiontimesw
40、ereselectedaccordingtoparametersofthetwowaterworksmonitoredinparallel.Thelabdeviceusedconsistsofglassbeakers(v)2L)withstator,astirrerwithstandardizedstirrergeometry,anddefinedsubmergedstirringdepths.Thestirringvelocitywasadjustedaccordingtothemeanvelocitygradient(Gvalue),whichisproportionaltotheintr
41、oducedenergyandthustotheaggregationofcolloids(26).Understirring(rpm:400min1),0.1mLofiron(l11)chloridesolution(40%)wasaddedto1.8Lofrawwater(spikedwith1ig/Lpharmaceuticals).Afterastirringtimeof1min,pH7.5wasattainedbyaddingCa(OH)2(lmolL).Then,theaggregationtomicroflocswasachievedbystirringslowlyfor20mi
42、nunder30minl.Aftersedimentationfor20min,asamplewastakenfromunderthewatersurface,andtheturbiditywasmeasured.Thesemeasurementsshowedthattheturbiditywasalwaysbelow1.5turbidityunitsofIbrmazine(TU/F).TABLE工AnalyticalMethodsUsedIcrDetenninationoftheTargetPharmaceuticalsmethodASCidmpotidsMhodBcarbamazepine
43、meUhudCacid8moLndSAcarbamazepinenwthDdDprimidonesamplevol(IL)1111filtrationglassfibers(=1tm)gldssfibers(1glassfibers(1rm)glassfibers(1rmpH2.07.5io7.5SPEmalcrhlCL5gofRP-Ce(ilsolut)1gofRP-iSeC(Baker)1gofRPC18(IS0.5gofEN(Merck)elulon3mLofmehanol1AmLofmethanol4mLofAiCeIOnewaporatlon4mLofmrelhanol,evapor
44、ationIodryness,additionot1mLofMhexaneevaporationIodrynesstodrynessWaporatlofitodrynessCierivatlzabofiaddHlonOfdiaZOmelhane50,trLofSllylationmixtureA?(fj也口mlnat1204OIDOjLofsllyhUonrnlxlijfeB-(fui&0mlrtat1120aC)16O.hLacetk:anhydrtJe/Emity怕m21：1Sunogalcstandardmeclofenamkcacidd1hydrocarDamaztpine2r3-dl
45、chIorophenoxyacelic3cW(5.3-D)dIhydrocaftama2cpl30CrlC10mln)scanmode*51MSIMHullscan(rangemfiBO-400)-SIMliterature20222722(C)ActivatedcarbonAdsorption.AdsorptionIsothermsTorthedeterminationoftheadsorptionisotherms,thefollowingparametershavebeenused:(i)200mLofdeionizedwalerorgroundwaterspikedwithinitia
46、lconcentrationsof100ig/Lofthepharmaceuticalsunderinvestigation,(ii)pulverizedgranularactivatedcarbonbasedoncoal,(iii)quantitiesofactivatedcarbonvariedtoachieveafinalconcentrationofthepharmaceuticalsinthesolutionthatisatleast2ordersofmagnitudessmallerthantheinitialone,(iv)smallportionsofactivatedcarb
47、on(0.2gL)addedassuspension,(v)batcheswithactivatedcarbontumbledin250-mLflasksfor24h,(vi)finallyallsampleswerefilteredwith0.45-iinpolycarbonatefilterandanalyzedaccordingtotheanalyticalmethoddescribedbefore.Evaluationoftheisothermswasperformedindoublelogarithmicscaleac-cordingtoFreundlich(27,28).Forasinglecompound,theFreundlichequationq)Kcndescribestherelationbetweentheloadingqoftheactiva
