2015
DOI: 10.1016/j.chroma.2014.12.008
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Bicyclic naphthenic acids in oil sands process water: Identification by comprehensive multidimensional gas chromatography–mass spectrometry

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 numerou… Show more

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Cited by 49 publications
(30 citation statements)
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“…These included the tricyclic diamondoid carboxylic acids, adamantane‐1‐carboxylic acid (A1CA) and 3‐ethyl adamantane carboxylic acid (3EA), which were investigated in our study. Tricyclic (and bicyclic) diamondoid carboxylic acids are major components of OSPW, and unrefined oil sands bitumen are reported to contain 90% tricyclic acids (Rowland et al , ; Wilde et al , ). Both A1CA and 3EA exhibit chronic toxicity and specifically were found to disrupt human liver enzyme activity (Scarlett et al , ).…”
Section: Introductionmentioning
confidence: 99%
“…These included the tricyclic diamondoid carboxylic acids, adamantane‐1‐carboxylic acid (A1CA) and 3‐ethyl adamantane carboxylic acid (3EA), which were investigated in our study. Tricyclic (and bicyclic) diamondoid carboxylic acids are major components of OSPW, and unrefined oil sands bitumen are reported to contain 90% tricyclic acids (Rowland et al , ; Wilde et al , ). Both A1CA and 3EA exhibit chronic toxicity and specifically were found to disrupt human liver enzyme activity (Scarlett et al , ).…”
Section: Introductionmentioning
confidence: 99%
“…Some components of OSPW are well understood: trace elements including metals, semimetals, and metalloids (Nix and Martin ; Siwik et al ; Bicalho et al ; Donner et al ), salts and ammonia (COSIA ), and suspended solids (El‐Din et al ; COSIA ; McQueen, Hendrikse et al ). However, the complexity of the organics in OSPW creates a practical challenge for determining treatment methods (Headley et al ; Pereira et al 2013; Goff et al ; Brown and Ulrich ; Quinlan and Tam ; Wilde et al ; Ajaero et al ), in addition to estimating potential risks (West et al ; Huang et al ). The estimation of potential risk is further supported through an existing understanding of chemical properties such as the propensity for bioaccumulation (Zhang et al ; Morandi et al ).…”
Section: Workhop Frameworkmentioning
confidence: 99%
“…Another possibility is that bicyclic acids were generated from in situ microbial alteration of shale organic matter (Saint-Édouard) and petroleum (Gaspé), as was inferred for the POT2 seep sample from the Haldimand region ( Figure 2). For instance, Wilde et al (2015)…”
Section: Accepted Manuscriptmentioning
confidence: 99%