Bicyclic naphthenic acids in oil sands process water: identification by comprehensive multidimensional gas chromatography-mass spectrometry.
dc.contributor.author | Wilde, Michael | |
dc.contributor.author | West, CE | |
dc.contributor.author | Scarlett, AG | |
dc.contributor.author | Jones, D | |
dc.contributor.author | Frank, RA | |
dc.contributor.author | Hewitt, LM | |
dc.contributor.author | Rowland, Steven | |
dc.date.accessioned | 2016-01-26T10:52:27Z | |
dc.date.accessioned | 2016-01-26T15:19:11Z | |
dc.date.available | 2016-01-26T10:52:27Z | |
dc.date.available | 2016-01-26T15:19:11Z | |
dc.date.issued | 2015-01-23 | |
dc.identifier.issn | 0021-9673 | |
dc.identifier.issn | 1873-3778 | |
dc.identifier.uri | http://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.extent | 74-87 | |
dc.format.medium | Print-Electronic | |
dc.language | eng | |
dc.language.iso | eng | |
dc.publisher | Elsevier | |
dc.relation.replaces | http://hdl.handle.net/10026.1/4229 | |
dc.relation.replaces | 10026.1/4229 | |
dc.subject | Bicyclics | |
dc.subject | GC×GC–MS | |
dc.subject | Naphthenic acids | |
dc.subject | Alkanes | |
dc.subject | Carboxylic Acids | |
dc.subject | Esters | |
dc.subject | Gas Chromatography-Mass Spectrometry | |
dc.subject | Oil and Gas Fields | |
dc.subject | Petroleum | |
dc.subject | Water Pollutants, Chemical | |
dc.title | Bicyclic naphthenic acids in oil sands process water: identification by comprehensive multidimensional gas chromatography-mass spectrometry. | |
dc.type | journal-article | |
dc.type | Article | |
plymouth.author-url | http://www.ncbi.nlm.nih.gov/pubmed/25553910 | |
plymouth.volume | 1378 | |
plymouth.publication-status | Published | |
plymouth.journal | Journal of Chromatography A | |
dc.identifier.doi | 10.1016/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.place | Netherlands | |
dcterms.dateAccepted | 2014-01-03 | |
dc.rights.embargodate | 2017-1-24 | |
dc.identifier.eissn | 1873-3778 | |
dc.rights.embargoperiod | Not known | |
rioxxterms.versionofrecord | 10.1016/j.chroma.2014.12.008 | |
rioxxterms.licenseref.uri | http://www.rioxx.net/licenses/all-rights-reserved | |
rioxxterms.licenseref.startdate | 2015-01-23 | |
rioxxterms.type | Journal Article/Review |