Assessing transformation products of chemicals by non-target and suspect screening : strategies and workflows v2

199 Pages·2016·4.853 MB·English

by  Drewes, Jörg E., Letzel, Thomas

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Drewes and Letzel; Assessing Transformation Products of Chemicals by Non-Target and Suspect Screening Strategies and ...
ACS Symposium Series; American Chemical Society: Washington, DC, 2016.
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Drewes and Letzel; Assessing Transformation Products of Chemicals by Non-Target and Suspect Screening Strategies and ...
ACS Symposium Series; American Chemical Society: Washington, DC, 2016.
1242
ACS SYMPOSIUM SERIES
Assessing Transformation
Products of Chemicals by Non-
Target and Suspect Screening −
Strategies and Workflows
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21/ Jör̈̈ g E. Drewes, Editor
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AmericanChemicalSociety,Washington,DC
DistributedinprintbyOxfordUniversityPress
Drewes and Letzel; Assessing Transformation Products of Chemicals by Non-Target and Suspect Screening Strategies and ...
ACS Symposium Series; American Chemical Society: Washington, DC, 2016.
LibraryofCongressCataloging-in-PublicationData
Names:Drewes,JörgE.,editor.|Letzel,Thomas,1970-editor.|American
ChemicalSociety.DivisionofEnvironmentalChemistry.
Title:Assessingtransformationproductsofchemicalsbynon-targetand
suspectscreening:strategiesandworkflows/JörgE.Drewes,editor,
TechnicalUniversityofMunich,Garching,Germany,ThomasLetzel,editor,
TechnicalUniversityofMunich,Garching,Germany;sponsoredbytheACS
DivisionofEnvironmentalChemistry.
1 Description:Washington,DC:AmericanChemicalSociety,[2016]-|Series:
0
0 ACSsymposiumseries;1242|Includesbibliographicalreferencesand
w
2.f index.
4 Identifiers:LCCN2016053208(print)|LCCN2016053607(ebook)|ISBN
2
6-1 9780841231955(v.2)|ISBN9780841231948(ebook)
01 Subjects:LCSH:Pollution.|Speciation(Chemistry)|
2
k- Pollutants--Biodegradation.|Ecologicalriskassessment.|Environmental
b
1/ chemistry.
2
0 Classification:LCCTD196.C45A872016(print)|LCCTD196.C45(ebook)|DDC
1
0. 628.1/68--dc23
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oi: LCrecordavailableathttps://lccn.loc.gov/2016053208
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Drewes and Letzel; Assessing Transformation Products of Chemicals by Non-Target and Suspect Screening Strategies and ...
ACS Symposium Series; American Chemical Society: Washington, DC, 2016.
Foreword
The ACS Symposium Series was first published in 1974 to provide a
mechanism for publishing symposia quickly in book form. The purpose of
the series is to publish timely, comprehensive books developed from the ACS
sponsoredsymposiabasedoncurrentscientificresearch. Occasionally,booksare
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0 forappropriateandcomprehensivecoverageandforinteresttotheaudience. Some
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bk- papersmaybeexcludedtobetterfocusthebook;othersmaybeaddedtoprovide
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2 comprehensiveness. When appropriate, overview or introductory chapters are
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Drewes and Letzel; Assessing Transformation Products of Chemicals by Non-Target and Suspect Screening Strategies and ...
ACS Symposium Series; American Chemical Society: Washington, DC, 2016.
Preface
Theidentificationandquantificationofthewidespreadoccurrenceoftraceorganic
chemicals at minute concentrations in the aqueous environment impacted by human
activitiesisaresultofrapidadvancesinenvironmentalanalyticalchemistry. Thebody
of knowledge regarding the characterization, fate and transport of these chemicals
1
0 of emerging concern (CECs) in the natural water environment and engineered water
0
2.pr treatmentprocesses,aswellastheirtoxicity,hasgrownsubstantiallyoverthelasttwo
4
2 decades. Recently, the focus in the environmental chemistry community has shifted
1
16- fromtheseCECparentcompoundstothefate,transport,andtoxicityoftransformation
0
k-2 products, which are generated through abiotic and biotic mechanisms in natural
1/b systemsandduringengineeredadvancedwatertreatmentprocesses.
2
0 This book evolved from a symposium presented at the 250th ACS National
1
10. Meeting&ExpositioninBoston, MAinAugust2015. Thesymposiumwasentitled
oi: “Assessing Transformation Products by Non-Target and Suspected Target Screening:
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6 | The New Frontier in Environmental Chemistry and Engineering,” and the topics
1
20 focused on featuring studies and recent advancements towards the development of
12, more harmonized strategies and workflows using non-target and suspects screening
ber methods, including suitable bioassay approaches to assess the overall relevance of
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e transformation products. Scientific research on the topic of transformation products
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D is rapidly growing, and we are glad that participants in the symposium and some
b): additional authors took time out of their busy schedules to prepare contributions for
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thisbookproject.
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at Atotalof21chaptersareincludedinthisbook,withcontributionsfrommostofthe
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n speakersfromthesymposiumandadditionalresearchinstitutions, aswellasLC-MS
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ati vendors. For convenience, this book is divided into two volumes. Volume I covers
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bli therelevanceoftransformationproductsandinternationalstrategiestomanageCECs,
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P newmethodsforacomprehensiveassessmentoftransformationproducts,andthefate
andtransportoftransformationproductsinnaturalsystems. VolumeIIaddressesthe
fate and transport of transformation products in engineered systems, assessing their
toxicity,commercialstrategiesinnon-targetandsuspectsscreening,andconcludeswith
developments towards harmonized strategies and workflows. This book is ideal for
environmentalscientistsandengineers,particularlychemists,environmentalengineers,
publichealthofficials,regulators,otherchemistry-relatedprofessionals,andstudents.
We are very thankful to the chapter authors for their contributions, the many
reviewers assisting in the peer-review process, and Arlene Furman, Elizabeth
Hernandez,andBobHausermanattheeditorialofficeofACSBooksfortheirsupport.
Special thanks go to Chloe Tuck and Brennan Tapp for their efficient handling of
the manuscripts. Without the dedication and patience of these individuals, this book
wouldn’thavehappened.
ix
Drewes and Letzel; Assessing Transformation Products of Chemicals by Non-Target and Suspect Screening Strategies and ...
ACS Symposium Series; American Chemical Society: Washington, DC, 2016.
JörgE.Drewes
ChairofUrbanWaterSystemsEngineering
TechnicalUniversityofMunich
AmCoulombwall8,Garching85748
Germany
ThomasLetzel
ChairofUrbanWaterSystemsEngineering
TechnicalUniversityofMunich
AmCoulombwall3,Garching85748
Germany
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Drewes and Letzel; Assessing Transformation Products of Chemicals by Non-Target and Suspect Screening Strategies and ...
ACS Symposium Series; American Chemical Society: Washington, DC, 2016.
©2016AmericanChemicalSociety
arecloselyrelatedto60oxidizedtransformationproductsfrom
Kendrickmassanalysisrevealedthat99precursorcompounds
byproducts could be identified using the NTS approach.
transformation products (valsartan acid), specific ozonation
Among typical wastewater contaminants (carbamazepine) and
could not be removed in a subsequent biofiltration process.
havebeenformed,fromwhichthemostpart(242compounds)
completely removed during ozonation, while 277 compounds
compounds detected in wastewater, only 506 have been
standards. The data reveal for example that from 1796
mass fragmentation spectra from libraries and with authentic
Compound identification was based on matches with accurate
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00 data filtering, statistical analysis and visualization tools.
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4
2 ozonation and subsequent biofiltration. The workflow
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16- processes of MPs and other wastewater constituents during
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2 screening (NTS) approach to assess the transformation
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1/b wastewater effluent. Therefore, we applied a non-target
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0 impact on the complex compound mixture of a secondary
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10. trace organic contaminants, little is known about its overall
oi: treatment plants due to its demonstrated ability to react with
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6 | considered in order to upgrade conventional wastewater
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20 input into receiving waters. While ozonation is increasingly
12, ecosystemsandhumanhealthrequiremeasurestoreducetheir
ber The potential risks of micropollutants (MPs) for aquatic
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at Hoelderlinstrasse12,72074Tuebingen,Germany
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Wastewater Treatment Plant Effluents
Approaches for Ozonation By-Products in
Accurate Mass Screening and Data Evaluation
Chapter 1
Drewes and Letzel; Assessing Transformation Products of Chemicals by Non-Target and Suspect Screening Strategies and ...
ACS Symposium Series; American Chemical Society: Washington, DC, 2016.
4
thosepharmaceuticalswhichmayremainbiologicallyactive.
should also be considered as major environmental contaminants, particularly
such as insect repellents (7). Finally, the main metabolites of these compounds
perfluorinatedcompounds(PFCs)andflameretardants,orpersonalcareproducts
of wastewater also include a wide range of industrial compounds such as
the contaminants of concern released to the environment through the discharge
the development of microorganisms resistant to antibiotics (5, 6). Morevoer
particular concern as there occurrence in the environment could contribute to
ciprofloxacin, clarithromycin, clindamycin and sulfamethoxazole which are of
is also reflected in wastewater composition with the frequent detection of
antidepressants citalopram and fluoxetine. The large consumption of antibiotics
and antiarrhythmic diltiazem; the antihistamine diphenhydramine; and the
1 and ibuprofen; the blood lipid regulator gemfibrozil, the antihypertensive
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h0 gabapentin and primidone; the painkillers diclofenac, naproxen, tramadol
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2. in wastewater (4) and freshwater (3) include the antiepileptics carbamazepine,
4
2
1 freshwater ecosystems (3). Other common pharmaceuticals frequently detected
6-
1 contaminants which are also among the most frequently detected compounds in
0
2
k- Germany(2),thebetablockersmetoprololandatenololarecommonwastewater
b
1/ the most considered. For instance, with several tons prescribed per year in
2
0
1 densely populated areas. Among these compounds, pharmeceuticals are often
0.
oi: 1 in the range of µg/l to ng/L are found in surface waters in particular in
d As a consequence a considerably large number of micropollutants (MPs)
16 | quality.
0
2, 2 waterbodiesandthereforeincreasethechallengetomaintainandimprovewater
er 1 change are further factors which may intensify pollutant burden of receiving
mb Growingpopulationdensityandvariationsinprecipitationeventsduetoclimate
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c bankfiltration is forced by groundwater abstraction for water supply near rivers.
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b): sewersystemsandbysurfacewater-groundwaterexchange,forexamplewhere
e into surface waters. Groundwater quality can be affected directly by leaking
W
e ( run-offandeffluentsfromwastewatertreatmentplantsaremajorsourcesofinput
Dat products,fromwhichapartisfinallyreleasedtotheenvironment. Surfacewater
on them are pesticides, industrial chemicals, pharmaceuticals and personal care
cati An estimated number of more than 30,000 compounds are in daily use. Among
ubli chemcials in the EC inventory of the Euorpean Chemicals Agency (ECHA) (1).
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protectionofwaterresourcesandecosystems. Todaywehavemorethan100,000
The use of synthetic organic compounds poses a big challenge for the
Introduction
treatment.
oxidation processes and which likely occur in wastewater
1,300 compounds with the potential to form N-oxides during
substructure search in a chemical database revealed more than
productsofcompoundswithatertiaryaminegroup. Afurther
which 27 could be assigned to N-oxides, typical oxidation
Drewes and Letzel; Assessing Transformation Products of Chemicals by Non-Target and Suspect Screening Strategies and ...
ACS Symposium Series; American Chemical Society: Washington, DC, 2016.
5
forfurtherreductionoftheinputofMPstotheaquaticenvironment. Measuresto
andhumanhealthfostersthescientificandpublicdiscussionandpoliticalaction
The increasing awareness of potential risks of MPs for aquatic ecosystems
AdvancedWastewaterTreatment
dataonchronicandinvivofishtoxicityofmostpharmaceuticals.
factor of 1000 lower. However, risk assessment is still hampered by the lack of
pharmaceuticalmixtures,eventhoughthecontributionofasinglecompoundisa
effluents have been modeled (12). The data clearly show potential risks from
toxicity concept ecotoxicological risks of pharmaceutical mixtures from WWTP
effluents contain MPs of ecotoxicological potential (11). With a classic mixture
rivers (10). With a set of five bioassays it has been demonstrated that WWTP
1 effects of EDCs have been shown in lake experiments (9) or exposed fish from
0
0
h mimic or interfere with the natural hormone system are an exception. Adverse
c
42. aquatic ecosystems (8). Endocrine disrupting compounds (EDCs) which can
2
6-1 changing composition makes it difficult to understand their effects on complex
01 numberintherangeofthousandsofcompoundsatlowconcentrationsandinever
2
k- Despite the ubiquitous occurrence of MPs in inland waters, their large
b
21/ fortheecosystemandforhumanhealth.
0
0.1 clearlydemonstratethatthesteadyinputofalargenumberofMPscanposearisk
1
oi: compounds which should be restricted in production and use. These examples
6 | d B of the Stockholm Convention on Persistent Organic Pollutants, which lists
1 chemicals are still produced in China. In 2009 PFOS was added to Annex
0
2
2, aphaseoutofPFOSproductionin2000bytheproducer. PFOSandPFOS-related
1
er investigationsoftheU.SEnvironmentalProtectionAgency(EPA)whichleadto
b
m itspersistence, bioaccumulationpotentialandtoxicity, PFOScameintofocusof
e
ec Union in 2008 based on its high toxicity to fish and other aquatic life. Due to
D
b): trifluralinwith30ng/L.Consequently,trifluralinhasbeenbannedintheEuropean
We surfactantperfluoroctanesulfonicacid(PFOS)with0.65ng/Lorfortheherbicide
e ( be rather low for some priority hazardous substances like for the perfluorinated
at
D substances. EQS for annual averages (AA-EQS) for inland surface waters can
n
o withtheaimtoprotecttheaquaticenvironmentfromadverseeffectsofchemicals
ati
blic 2008/105/EC)oftheEuropeanParliamentandtheCounciloftheEuropeanUnion
u substances by the Directive on Environmental Quality Standards (Directive
P

Environmental Quality Standards (EQS) have been defined for priority
pharmaceuticalhormone17-beta-estradiol(EE2).
theestrogenincontraceptives17-alpha-ethinylestradiol(E2)andthenaturaland
the macrolide antibiotics erythromycin, clarithromycin and azithromycin and
includespharmaceuticalslikethenonsteroidalanti-inflammatorydrugdiclofenac,
or of insufficient quality to assess the environmental risk. The Watch List also
other chemicals for which the available monitoring data are either insufficient
(Directive 2013/39/EC) introduced a new Watch List of emerging pollutants or
Commission (EC 2000/60/EC). The amended directive for priority substances
according to the Water Framewaork Directive (WFD) of the European
priority substances in the field of water policy, which have to be monitored
So far only a few of these compounds have been included into the list of
Drewes and Letzel; Assessing Transformation Products of Chemicals by Non-Target and Suspect Screening Strategies and ...
ACS Symposium Series; American Chemical Society: Washington, DC, 2016.