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dc.contributor.authorWilde, MJen
dc.contributor.authorWest, CEen
dc.contributor.authorScarlett, AGen
dc.contributor.authorJones, Den
dc.contributor.authorFrank, RAen
dc.contributor.authorHewitt, LMen
dc.contributor.authorRowland, SJen
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.issued2015-01-23en
dc.identifier.issn0021-9673en
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.

en
dc.format.extent74 - 87en
dc.languageengen
dc.language.isoengen
dc.publisherElsevieren
dc.relation.replaceshttp://hdl.handle.net/10026.1/4229
dc.relation.replaces10026.1/4229
dc.subjectBicyclicsen
dc.subjectGC×GC–MSen
dc.subjectNaphthenic acidsen
dc.subjectAlkanesen
dc.subjectCarboxylic Acidsen
dc.subjectEstersen
dc.subjectGas Chromatography-Mass Spectrometryen
dc.subjectOil and Gas Fieldsen
dc.subjectPetroleumen
dc.subjectWater Pollutants, Chemicalen
dc.titleBicyclic naphthenic acids in oil sands process water: identification by comprehensive multidimensional gas chromatography-mass spectrometry.en
dc.typeJournal Article
plymouth.author-urlhttp://www.ncbi.nlm.nih.gov/pubmed/25553910en
plymouth.volume1378en
plymouth.publication-statusPublisheden
plymouth.journalJournal of Chromatography Aen
dc.identifier.doi10.1016/j.chroma.2014.12.008en
plymouth.organisational-group/Plymouth
plymouth.organisational-group/Plymouth/Faculty of Science and Engineering
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/Professional Services staff
dc.publisher.placeNetherlandsen
dcterms.dateAccepted2014-01-03en
dc.rights.embargodate2017-01-24en
dc.identifier.eissn1873-3778en
dc.rights.embargoperiodNot knownen
rioxxterms.versionofrecord10.1016/j.chroma.2014.12.008en
rioxxterms.licenseref.urihttp://www.rioxx.net/licenses/all-rights-reserveden
rioxxterms.licenseref.startdate2015-01-23en
rioxxterms.typeJournal Article/Reviewen


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