10种脂肪酰乙醇胺制备工艺优化及其结构表征Process optimization of preparation of 10 fatty acid ethanolamines and its structural characterization

Abstract

为了优化脂肪酰乙醇胺的制备工艺，以油酸甲酯和乙醇胺为原料，采用无溶剂法制备油酰乙醇胺，采用单因素实验优化了反应条件。然后以10种脂肪酸甲酯为原料，考察了该反应方法的普适性，并对制备得到的10种脂肪酰乙醇胺的结构进行了表征。结果表明：制备油酰乙醇胺的最佳工艺条件为无溶剂、油酸甲酯与乙醇胺物质的量比1∶ 5、反应温度100 ℃、反应时间15 h，在此条件下油酰乙醇胺产率为76.52%；在最佳工艺条件下考察了反应底物的普适性，得到10种脂肪酰乙醇胺目标化合物，其产率在53%~87%之间，并通过核磁氢谱、碳谱以及高分辨质谱确证了目标化合物的结构。该方法反应条件绿色无污染，分离纯化成本低，操作简易，且可以获得克级以上的高纯度脂肪酰乙醇胺，可为以后开展脂肪酰乙醇胺生物活性研究提供足够的样品。 In order to optimize the process of preparation of fatty acid ethanolamine, with methyl oleate and ethanolamine as raw materials, n-oleoyl ethanolamine was prepared by solvent free method, and the reaction conditions were optimized by single factor experiment. Then 10 fatty acid methyl esters were used as raw materials, the universality of the method was investigated, and the structures of 10 fatty acid ethanolamines were characterized. The results showed that the optimal process conditions of preparation of n-oleoyl ethanolamine were obtained as follows:solvent free, molar ratio of methyl oleate to ethanolamine 1∶ 5, reaction temperature 100 ℃ and reaction time 15 h. Under these conditions, the yield of n-oleoyl ethanolamine was 76.52%. Under the optimal conditions, the universality of the substrate was investigated, and the yields of the 10 fatty acid ethanolamines(target compounds) were 53%-87%. The structures of the target compounds were further confirmed by 1H NMR, 13C NMR and high resolution mass spectrometry. The method has the advantages of no pollution, low cost, simple operation, and can obtain high-purity fatty acid ethanolamine above gram level, which can provide sufficient samples for the biological activity research of fatty acid ethanolamine in the future.

Keywords

• 脂肪酰乙醇胺；制备；结构表征
• fatty acid ethanolamine; preparation; structural characterization