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    Bicyclic naphthenic acids in oil sands process water: Identification by comprehensive multidimensional gas chromatography-mass spectrometry

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    Authors
    Wilde, M.
    West, C.
    Scarlett, Alan
    Jones, D.
    Frank, R.
    Hewitt, L.
    Rowland, S.
    Date
    2015
    Type
    Journal Article
    
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    Citation
    Wilde, M. and West, C. and Scarlett, A. and Jones, D. and Frank, R. and Hewitt, L. and Rowland, S. 2015. Bicyclic naphthenic acids in oil sands process water: Identification by comprehensive multidimensional gas chromatography-mass spectrometry. Journal of Chromatography A. 1378: pp. 74-87.
    Source Title
    Journal of Chromatography A
    DOI
    10.1016/j.chroma.2014.12.008
    ISSN
    0021-9673
    URI
    http://hdl.handle.net/20.500.11937/46644
    Collection
    • Curtin Research Publications
    Abstract

    © 2014 Elsevier B.V. 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.

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