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dc.contributor.authorWilde, Michael
dc.contributor.authorWest, CE
dc.contributor.authorScarlett, AG
dc.contributor.authorJones, D
dc.contributor.authorFrank, RA
dc.contributor.authorHewitt, LM
dc.contributor.authorRowland, Steven
dc.date.accessioned2016-01-26T10:52:27Z
dc.date.accessioned2016-01-26T15:19:11Z
dc.date.available2016-01-26T10:52:27Z
dc.date.available2016-01-26T15:19:11Z
dc.date.issued2015-01-23
dc.identifier.issn0021-9673
dc.identifier.issn1873-3778
dc.identifier.urihttp://hdl.handle.net/10026.1/4232
dc.description.abstract

Although bicyclic acids have been reported to be the major naphthenic acids in oil sands process-affected water (OSPW) and a well-accepted screening assay indicated that some bicyclics were the most acutely toxic acids tested, none have yet been identified. Here we show by comprehensive multidimensional gas chromatography-mass spectrometry (GC×GC-MS), that >100 C8-15 bicyclic acids are typically present in OSPW. Synthesis or purchase allowed us to establish the GC×GC retention times of methyl esters of numerous of these and the mass spectra and published spectra of some additional types, allowed us to identify bicyclo[2.2.1]heptane, bicyclo[3.2.1]octane, bicyclo[4.3.0]nonane, bicyclo[3.3.1]nonane and bicyclo[4.4.0]decane acids in OSPW and a bicyclo[2.2.2]octane acid in a commercial acid mixture. The retention positions of authentic bicyclo[3.3.0]octane and bicyclo[4.2.0]octane carboxylic acid methyl esters and published retention indices, showed these were also possibilities, as were bicyclo[3.1.1]heptane acids. Bicyclo[5.3.0]decane and cyclopentylcyclopentane carboxylic acids were ruled out in the samples analysed, on the basis that the corresponding alkanes eluted well after bicyclo[4.4.0]decane (latest eluting acids). Bicyclo[4.2.1]nonane, bicyclo[3.2.2]nonane, bicyclo[3.3.2]decane, bicyclo[4.2.2]decane and spiro[4.5]decane carboxylic acids could not be ruled out or in, as no authentic compounds or literature data were available. Mass spectra of the methyl esters of the higher bicyclic C12-15 acids suggested that many were simply analogues of the acids identified above, with longer alkanoate chains and/or alkyl substituents. Our hypothesis is that these acids represent the biotransformation products of the initially somewhat more bio-resistant bicyclanes of petroleum. Although remediation studies suggest that many bicyclic acids can be relatively quickly removed from suitably treated OSPW, examination by GC×GC-MS may show which isomers are affected most. Knowledge of the structures will allow the toxicity of any residual isomers to be calculated and measured.

dc.format.extent74-87
dc.format.mediumPrint-Electronic
dc.languageeng
dc.language.isoeng
dc.publisherElsevier
dc.relation.replaceshttp://hdl.handle.net/10026.1/4229
dc.relation.replaces10026.1/4229
dc.subjectBicyclics
dc.subjectGC×GC–MS
dc.subjectNaphthenic acids
dc.subjectAlkanes
dc.subjectCarboxylic Acids
dc.subjectEsters
dc.subjectGas Chromatography-Mass Spectrometry
dc.subjectOil and Gas Fields
dc.subjectPetroleum
dc.subjectWater Pollutants, Chemical
dc.titleBicyclic naphthenic acids in oil sands process water: identification by comprehensive multidimensional gas chromatography-mass spectrometry.
dc.typejournal-article
dc.typeArticle
plymouth.author-urlhttp://www.ncbi.nlm.nih.gov/pubmed/25553910
plymouth.volume1378
plymouth.publication-statusPublished
plymouth.journalJournal of Chromatography A
dc.identifier.doi10.1016/j.chroma.2014.12.008
plymouth.organisational-group/Plymouth
plymouth.organisational-group/Plymouth/Faculty of Science and Engineering
plymouth.organisational-group/Plymouth/Faculty of Science and Engineering/School of Geography, Earth and Environmental Sciences
plymouth.organisational-group/Plymouth/Research Groups
plymouth.organisational-group/Plymouth/Research Groups/Marine Institute
plymouth.organisational-group/Plymouth/Users by role
plymouth.organisational-group/Plymouth/Users by role/Academics
dc.publisher.placeNetherlands
dcterms.dateAccepted2014-01-03
dc.rights.embargodate2017-1-24
dc.identifier.eissn1873-3778
dc.rights.embargoperiodNot known
rioxxterms.versionofrecord10.1016/j.chroma.2014.12.008
rioxxterms.licenseref.urihttp://www.rioxx.net/licenses/all-rights-reserved
rioxxterms.licenseref.startdate2015-01-23
rioxxterms.typeJournal Article/Review


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