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

LAN Chunbo1,QIN Lulu1,SU Youxue2,ZHAO Jingchan1   

  1. 1Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education,College of Chemistry & Materials Science,Northwest University,Xi’an 710069,Shaanxi,China; 2 Shaanxi Special Rubber Products Co.,LTD,Xi’an 710069,Shaanxi,China
  • Online:2013-03-05 Published:2013-03-05

桐油制备3-正丁基-6-(1-癸烯酸基)-4-环己烯二酸

蓝春波1,秦露露1 ,苏有学2 ,赵景婵1   

  1. 1西北大学化学与材料科学学院,西北大学合成与天然功能分子化学教育部重点实验室,陕西 西安 710069; 2陕西特种橡胶制品有限公司,陕西 西安 710069

Abstract: 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-IR spectroscopy,MS and 1H NMR. The optimal reaction condition was determined by orthogonal experiment,as follows:α-eleostearic acid methyl ester and maleic anhydride feed ratio of 1∶1.2,reaction temperature 160 ℃,reaction time is 2 hours.

Key words: tung oil, maleic anhydride, Diels-Alder reaction, C22 tricarboxylic acid

摘要: 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。

关键词: 桐油, 马来酸酐, Diels-Alder反应, C22三元羧酸

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