ABSTRACT Oleic and linoleic acids are common fatty acids in commodity vegetable oils. Their modification into sulfur-containing molecules can be a route for producing biobased lubricants. We investigated modification of methyl oleate and methyl linoleate with thioacetic acid using UV-initiated thio-ene reaction to obtain methyl (acetylthio)stearates and methyl bis(acetylthio)stearates, respectively. Small amounts of acetyldithio derivatives were also detected. The products were characterized by Electron Impact Mass Spectrometry, High Resolution Mass Spectrometry, and 1- and 2-D NMR. The MS confirmed the anticipated molecular formulas. The fragmentation patterns can be explained with predominant breakage of carbon–sulfur bonds. The isomers of methyl bis(acetylthio)stearates were partially separated by chromatography, and some characteristic NMR peaks were identified and compared with the ones predicted by software. NMR showed distinct patterns of the quasi-meso- and quasi-rac- forms of the isomers. Most often thioacetates are used as protecting groups or intermediary of thiol groups. GRAPHICAL ABSTRACT

中文翻译：

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乙酰硫代硬脂酸酯 - 质谱和核磁共振表征*

摘要油酸和亚油酸是商品植物油中常见的脂肪酸。将它们改性为含硫分子可以成为生产生物基润滑剂的途径。我们研究了用硫代乙酸对油酸甲酯和亚油酸甲酯的改性，使用紫外线引发的硫烯反应分别获得（乙酰硫基）硬脂酸甲酯和双（乙酰硫基）硬脂酸甲酯。还检测到少量乙酰二硫代衍生物。产物通过电子冲击质谱、高分辨率质谱以及一维和二维核磁共振进行表征。MS 确认了预期的分子式。断裂模式可以用碳硫键的主要断裂来解释。双（乙酰硫基）硬脂酸甲酯的异构体通过色谱法部分分离，并对一些特征核磁共振峰进行了鉴定，并与软件预测的峰进行了比较。NMR 显示异构体的准内消旋和准外消旋形式的不同模式。最常使用硫代乙酸盐作为保护基团或硫醇基团的中间体。图形概要