Diaromatic sulphur-containing ‘naphthenic’ acids in process waters

West, Charles E.; Scarlett, Alan G.; Tonkin, Andrew; O'Carroll-Fitzpatrick, Devon; Pureveen, J.; Tegelaar, Erik; Gieleciak, Rafał; Hager, Darcy; Petersen, Karen Koefoed; Tollefsen, Knut-Erik; Rowland, Steven J.

doi:10.1016/j.watres.2013.10.058

Cited by 40 publications

(38 citation statements)

References 34 publications

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“…In this context we note that tentative structures of sulfur‐containing naphthenic acids have been proposed in a recent study . However, this is the first study in which structures of thiophene acids have been established by comparison with reference standards.…”

Section: Resultsmentioning

confidence: 79%

Identification of individual thiophene-, indane-, tetralin-, cyclohexane-, and adamantane-type carboxylic acids in composite tailings pore water from Alberta oil sands

Bowman

Slater

Warren

et al. 2014

Rapid Commun. Mass Spectrom.

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Section: Resultsmentioning

confidence: 79%

Identification of individual thiophene-, indane-, tetralin-, cyclohexane-, and adamantane-type carboxylic acids in composite tailings pore water from Alberta oil sands

Bowman

Slater

Warren

et al. 2014

Rapid Commun. Mass Spectrom.

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“…and the unknowns may well be diacid analogues of compounds similar to the latter. Such non‐heteroatom‐containing acids have been widely reported in OSPW and petroleum (e.g …”

Section: Resultsmentioning

confidence: 99%

“…Recently, use of modern coupled chromatographic and mass spectrometric techniques has allowed some components to be assigned, or at least delimited (e.g …”

mentioning

confidence: 99%

“…Jones et al . had already examined hexane, and hexane/ether, and West et al ., ether and Ag + SPE eluates, of this OSPW extract (methylated) and they identified alicyclic, naphthenoaromatic and heteroaromatic carboxylic acids in the methylated fractions. Minor aromatic sulphur‐containing acids were also present as methyl esters .…”

mentioning

confidence: 99%

“…had already examined hexane, and hexane/ether, and West et al ., ether and Ag + SPE eluates, of this OSPW extract (methylated) and they identified alicyclic, naphthenoaromatic and heteroaromatic carboxylic acids in the methylated fractions. Minor aromatic sulphur‐containing acids were also present as methyl esters . However, a remaining methanol eluate, probably containing more polar compounds, was not examined as these compounds were probably less amenable to GC‐based methods.…”

mentioning

confidence: 99%

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Mass spectral characterisation of a polar, esterified fraction of an organic extract of an oil sands process water

Rowland

Pereira

Martin

et al. 2014

Rapid Comm Mass Spectrometry

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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.

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Effects of dibenzothiophene, a sulfur‐containing heterocyclic aromatic hydrocarbon, and its alkylated congener, 2,4,7‐trimethyldibenzothiophene, on placental trophoblast cell function

Raez-Villanueva

Perono

Jamshed

et al. 2020

J of Applied Toxicology

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Worldwide demand for petroleum products has resulted in increased oil and gas activities in many countries. Conventional and unconventional oil and gas extraction, production, and transport lead to increased levels of petroleum‐derived polycyclic aromatic hydrocarbons (PAHs) in the environment. PAH exposure has profound effects on reproduction by affecting pathways involved in placental trophoblast cell function and impairing normal placental development and function—key contributors to reproductive success. However, other components found in petroleum and wastewaters from oil and gas extraction, including the sulfur‐containing heterocyclic aromatic compounds such as dibenzothiophene (DBT) and its alkylated derivatives, may also impact reproductive success. The goal of this study was to examine the effect of exposure to DBT, a compound commonly detected in the environment, and one of its alkylated analogues, 2,4,7‐trimethyldibenzothiophene (2,4,7‐DBT), on steroidogenic and angiogenic pathways critical for mammalian development in placental trophoblast cells (HTR‐8/SVneo cells). 2,4,7‐DBT but not DBT increased estradiol output in association with increased tube‐like formation (surrogate for angiogenesis). These changes in angiogenesis did not appear to be related to altered expression of the key placental angiogenic gene targets (ANGPTL4, VEGFA, and PGF). Neither compound showed a concentration related effect on progesterone synthesis or its receptor expression. Our results suggest that 2,4,7‐DBT can disrupt key pathways important for placental trophoblast function and highlight the importance of determining the impact of exposure to both parent and alkylated compounds. Further, these data suggest that exposure to sulfur‐containing heterocyclic aromatic compounds may lead to placental dysfunction and impact reproductive success at environmentally relevant levels.

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Diaromatic sulphur-containing ‘naphthenic’ acids in process waters

Cited by 40 publications

References 34 publications

Identification of individual thiophene-, indane-, tetralin-, cyclohexane-, and adamantane-type carboxylic acids in composite tailings pore water from Alberta oil sands

Identification of individual thiophene-, indane-, tetralin-, cyclohexane-, and adamantane-type carboxylic acids in composite tailings pore water from Alberta oil sands

Mass spectral characterisation of a polar, esterified fraction of an organic extract of an oil sands process water

Effects of dibenzothiophene, a sulfur‐containing heterocyclic aromatic hydrocarbon, and its alkylated congener, 2,4,7‐trimethyldibenzothiophene, on placental trophoblast cell function

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