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Abundant naphthenic acids in oil sands process-affected water: studies by synthesis, derivatisation and two-dimensional gas chromatography/high-resolution mass spectrometry.
MedLine Citation:
PMID:  23239384     Owner:  NLM     Status:  In-Data-Review    
Abstract/OtherAbstract:
RATIONALE: The large volumes of 'supercomplex' mixtures of reputedly toxic organic compounds in acidic extracts of oil sands process-affected waters (OSPW) represent a challenging goal for complete characterisation. To date, comprehensive two-dimensional gas chromatography/time-of-flight mass spectrometry (GCxGC/TOFMS) has allowed the acquisition and interpretation of numerous electron ionisation mass spectra including many of those confirmed to be tricyclic and pentacyclic carboxylic acids by reference to the spectra and retention positions of authentic or synthetic compounds. This has allowed the toxicities of some of the identified acids to be determined and their environmental significance to be better assessed.
METHODS: Synthesis, derivatisation (methyl, trideuteriomethyl and trimethylsilyl esters) and GCxGC/TOFMS with nominal mass and higher mass accuracy (ca. 5 ppm) were used to study three abundant unknown acids present in OSPW samples from two different industrial suppliers.
RESULTS: GCxGC/TOFMS with nominal mass accuracy, of methyl, trideuteriomethyl and trimethylsilyl esters of three abundant acids in two OSPW samples, produced mass spectra consistent with their assignment as either C(16) tetracyclic acids or as isobaric pentacyclic C(15) hydroxy acids ('O(3) ') or sulfur-containing ('SO(2) ') species. The synthesis of several isomeric pentacyclic C(15) hydroxy acids and examination of the GCxGC retention times and mass spectra (nominal mass) of their derivatives suggested that the unknown OSPW acids were not hydroxy acids, and GCxGC/TOFMS with higher mass accuracy ruled out the possibility. The possibility that they were isobaric 'SO(2) ' species could also be dismissed as this was inconsistent with accurate masses, the derivatisation reactions observed, the fragmentation patterns and the isotope distributions, which excluded the presence of sulphur.
CONCLUSIONS: The data support the contention that the three abundant unknowns were indeed C(16) tetracyclic acids. An equally rigorous approach will be necessary to characterise further acids in such mixtures. This is important so that chemistry can be used to guide the search for toxic modes of action. Copyright © 2012 John Wiley & Sons, Ltd.
Authors:
Charles E West; Alan G Scarlett; Jos Pureveen; Erik W Tegelaar; Steven J Rowland
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Rapid communications in mass spectrometry : RCM     Volume:  27     ISSN:  1097-0231     ISO Abbreviation:  Rapid Commun. Mass Spectrom.     Publication Date:  2013 Jan 
Date Detail:
Created Date:  2012-12-14     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8802365     Medline TA:  Rapid Commun Mass Spectrom     Country:  England    
Other Details:
Languages:  eng     Pagination:  357-65     Citation Subset:  IM    
Copyright Information:
Copyright © 2012 John Wiley & Sons, Ltd.
Affiliation:
Petroleum and Environmental Geochemistry Group, Biogeochemistry Research Centre, University of Plymouth, Drake Circus, Plymouth, PL4 8AA, UK.
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