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dc.contributor.authorRowland, SJ
dc.contributor.authorPereira, AS
dc.contributor.authorMartin, JW
dc.contributor.authorScarlett, AG
dc.contributor.authorWest, CE
dc.contributor.authorLengger, SK
dc.contributor.authorWilde, MJ
dc.contributor.authorPureveen, J
dc.contributor.authorTegelaar, EW
dc.contributor.authorFrank, RA
dc.contributor.authorHewitt, LM
dc.date.accessioned2016-04-14T09:23:13Z
dc.date.available2016-04-14T09:23:13Z
dc.date.issued2014-11-15
dc.identifier.issn0951-4198
dc.identifier.issn1097-0231
dc.identifier.urihttp://hdl.handle.net/10026.1/4500
dc.description.abstract

RATIONALE: Characterising complex mixtures of organic compounds in polar fractions of heavy petroleum is challenging, but is important for pollution studies and for exploration and production geochemistry. Oil sands process-affected water (OSPW) stored in large tailings ponds by Canadian oil sands industries contains such mixtures. METHODS: A polar OSPW fraction was obtained by silver ion solid-phase extraction with methanol elution. This was examined by numerous methods, including electrospray ionisation (ESI) Fourier transform ion cyclotron resonance mass spectrometry (FTICRMS) and ultra-high-pressure liquid chromatography (uHPLC)/Orbitrap MS, in multiple ionisation and MS/MS modes. Compounds were also synthesised for comparison. RESULTS: The major ESI ionisable compounds detected (+ion mode) were C15-28 SO3 species with 3-7 double bond equivalents (DBE) and C27-28 SO5 species with 5 DBE. ESI-MS/MS collision-induced losses were due to water, methanol, water plus methanol and water plus methyl formate, typical of methyl esters of hydroxy acids. Once the fraction was re-saponified, species originally detected by positive ion MS, could be detected only by negative ion MS, consistent with their assignment as sulphur-containing hydroxy carboxylic acids. The free acid of a keto dibenzothiophene alkanoic acid was added to an unesterified acid extract of OSPW in known concentrations as a putative internal standard, but attempted quantification in this way proved unreliable. CONCLUSIONS: The results suggest the more polar acidic organic SO3 constituents of OSPW include C15-28  S-containing, alicyclic and aromatic hydroxy carboxylic acids. SO5 species are possibly sulphone analogues of these. The origin of such compounds is probably via further biotransformation (hydroxylation) of the related S-containing carboxylic acids identified previously in a less polar OSPW fraction. The environmental risks, corrosivity and oil flow assurance effects should be easier to assess, given that partial structures are now known, although further identification is still needed.

dc.format.extent2352-2362
dc.format.mediumPrint
dc.languageen
dc.language.isoen
dc.publisherWiley
dc.subjectChromatography, High Pressure Liquid
dc.subjectEsters
dc.subjectOil and Gas Fields
dc.subjectOrganic Chemicals
dc.subjectSolid Phase Extraction
dc.subjectSpectrometry, Mass, Electrospray Ionization
dc.subjectSulfur Compounds
dc.titleMass spectral characterisation of a polar, esterified fraction of an organic extract of an oil sands process water.
dc.typejournal-article
dc.typeArticle
plymouth.author-urlhttp://www.ncbi.nlm.nih.gov/pubmed/25279749
plymouth.issue21
plymouth.volume28
plymouth.publisher-urlhttp://dx.doi.org/10.1002/rcm.7024
plymouth.publication-statusPublished
plymouth.journalRapid Commun Mass Spectrom
dc.identifier.doi10.1002/rcm.7024
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/REF 2021 Researchers by UoA
plymouth.organisational-group/Plymouth/REF 2021 Researchers by UoA/UoA07 Earth Systems 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.placeEngland
dcterms.dateAccepted2014-11-13
dc.rights.embargodate2016-11-16
dc.identifier.eissn1097-0231
dc.rights.embargoperiod12 months
rioxxterms.versionofrecord10.1002/rcm.7024
rioxxterms.licenseref.urihttp://www.rioxx.net/licenses/under-embargo-all-rights-reserved
rioxxterms.licenseref.startdate2014-11-15
rioxxterms.typeJournal Article/Review


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