桐油制备3-正丁基-6-(1-癸烯酸基)-4-环己烯二酸

Synthesis 3-n-butyl-6-(1-decyl olefinic acid base)-4-cyclohexene diacid from tung oil

以桐油为原料制备3-正丁基-6-(1-癸烯酸基)-4-环己烯二酸,分子式为C22H34O6(C22三元羧酸)。首先通过酯交换反应得到桐油酸甲酯,桐油酸甲酯与马来酸酐经过Diels-Alder反应制备3-正丁基-6-(1-癸烯酸甲酯基)-4-环己烯二酸,再经过皂化、酸化和分离等过程得到C22三元羧酸。用FT-IR、MS及1H NMR对其结构进行表征。采用正交试验考察Diels-Alder反应的最佳反应条件为:桐油酸甲酯与马来酸酐投料比为1∶1.2,反应温度为160℃,反应时间为2 h。

3-n-butyl-6-（1-decyl olefinic acid base）-4-cyclohexene diacid （C22 tricarboxylic acid） was prepared with tung oil as raw material through the steps of transesterification reaction with methanol, Diels-Alder reaction with maleic anhydride, saponification and acidification sequentially. The structure of the C22 tricarboxylic acid was characterized by FT-1R spectroscopy, MS and IH NMR. The optimal reaction condition was determined by orthogonal experiment, as follows： a-eleostearic acid methyl ester and maleic anhydride feed ratio of 1 ： 1.2, reaction temperature 160 ℃, reaction time is 2 hours.