Abstract Concerns over the toxicity associated with ‘naphthenic’ acids (NA) within oil produced waters and oil sands process waters (OSPW), whether justified or not, have increased the need for the structural elucidation of NA. Certainly, oil sands mining operations, such as those in Alberta, Canada, result in the production of large volumes of OSPW contaminated with NA. Monitoring NA, predicting the toxicities and accounting for the toxicity of residual NA after clean-up treatments, have all been hindered by the lack of NA identifications. Recently, a method involving the conversion of the esters of petroleum NA to the corresponding hydrocarbons before analysis by comprehensive two-dimensional gas chromatography-mass spectrometry (GC × GC–MS), resulted in the most comprehensive study of bicyclic NA from petroleum to date. Here, we present results of the analysis by GC × GC–MS of NA extracted from OSPW after conversion of the acids or ester derivatives to the corresponding hydrocarbons. The identifications presented include novel alicyclic, aromatic and sulfur-containing hydrocarbons and thus, by inference, of the corresponding acids. This supports and significantly extends, previous identifications of OSPW NA as their methyl esters and can now be used to better inform environmental monitoring programs and toxicity studies.

中文翻译：

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油砂工艺水中的环烷酸：通过酸或酯转化为碳氢化合物进行鉴定

摘要 对与采油水和油砂工艺用水 (OSPW) 中“环烷”酸 (NA) 相关的毒性的担忧，无论是否合理，都增加了对 NA 结构阐明的需求。当然，油砂开采作业（例如在加拿大艾伯塔省的作业）会导致生产大量被 NA 污染的 OSPW。由于缺乏 NA 鉴定，监测 NA、预测毒性和解释清理处理后残留 NA 的毒性都受到阻碍。最近，一种在综合二维气相色谱 - 质谱 (GC × GC-MS) 分析之前将石油 NA 的酯转化为相应烃的方法，导致了迄今为止对石油中双环 NA 的最全面研究. 这里，我们展示了在将酸或酯衍生物转化为相应的碳氢化合物后，从 OSPW 中提取的 NA 的 GC × GC-MS 分析结果。所提供的鉴定包括新的脂环族、芳香族和含硫烃，因此推断出相应的酸。这支持并显着扩展了先前将 OSPW NA 鉴定为它们的甲酯，现在可用于更好地为环境监测计划和毒性研究提供信息。