植物甾醇琥珀酸酯化反应及产物的重结晶分离研究

【作者】 邵强；

【导师】 许文林；

【作者基本信息】 扬州大学 ， 应用化学， 2006， 硕士

【摘要】 植物甾醇是一类重要的甾体化合物。通过植物甾醇与琥珀酸酐酯化反应后,可以提高植物甾醇的亲水能力,并且其酯化产物由于其特有的生理功能及理化性质,被广泛地应用于食品、医药和化妆品行业。本文以植物甾醇与琥珀酸酐的酯化反应及酯化产物的分离精制过程为研究体系,研究了β-谷甾醇和豆甾醇分别与琥珀酸酐酯化反应的工艺和动力学及植物甾醇琥珀酸单酯的合成工艺;应用溶剂结晶法分离植物甾醇琥珀酸单酯。为植物甾醇琥珀酸酯化反应过程和植物甾醇琥珀酸酯化产物的分离与精制过程的工业化提供理论指导和技术参数。本研究主要在以下各方面开展工作:1β-谷甾醇和豆甾醇与琥珀酸酐酯化反应工艺和动力学β-谷甾醇和豆甾醇分别与琥珀酸酐酯化反应的产物经元素分析法、核磁共振波谱法确定反应产物为β-谷甾醇琥珀酸单酯和豆甾醇琥珀酸单酯。以甲苯为溶剂,吡啶为催化剂,分别研究β-谷甾醇和豆甾醇与琥珀酸酐酯化反应工艺条件和动力学。探讨了反应物的物质的量、催化剂吡啶的用量、反应温度对酯化反应速率和酯化率的影响;在β-谷甾醇或豆甾醇与琥珀酸酐按摩尔比为1.0:1.6,1.5%的吡啶作为催化剂,回流下反应20h后,酯化反应趋于完全,甾醇的收率大于86%;在甲苯溶剂中,β-谷甾醇和豆甾醇与琥珀酸酐均相单酯化反应为二级反应,反应的活化能为84～85kJ·mol^-1。2植物甾醇与琥珀酸酐酯化反应研究了植物甾醇琥珀酸单酯的合成及分离精制过程。应用高效液相色谱对混合植物甾醇琥珀酸酯化产物中各组分的含量进行了分析测定。实验结果表明,各种植物甾醇琥珀酸单酯的分离效果较好,响应时间在10min左右,面积归一法能够快速准确地用于该过程的分析测试。3植物甾醇琥珀酸单酯的重结晶分离精制测定了室温下β-谷甾醇琥珀酸单酯和豆甾醇琥珀酸单酯在有机溶剂中的溶解度,利用β-谷甾醇琥珀酸单酯和豆甾醇琥珀酸单酯在环己酮的溶解度随温度变化更多还原

【Abstract】 Phytosterol is ond kind of important steroids. It has been reported that the hydrophilicity of phytosterol can be strengthened and the solubility in the water is also increased through modifying hydroxyl at C-3 position with succinic anhydride. Since phytosterol hemisuccinate are known to have a wide range of biological activility and physical properties, they are widely applied in the food, pharmaceutics and cosmetic industry. The hemisuccination process and kinetics ofβ-sitosterol and stigmasterol with succinic anhydride were studied, respectively. Synthesis of phytosterol hemisuccinate was also studied.The pure singleβ-sitosterol hemisuccinate and stigmasterol hemisuccinate were purified and separated from phytosterol hemisuccinate by crystallization method. The research results provide theorical basic and technological parameter for the industrialization of the process. The main research works were as follows:1. The hemisuccination process and kinetics ofβ-sitosterol and stigmasterol with succinic anhydrideThe reaction product ofβ-sitosterol and stigmasterol with succinic anhydride were characterized by elemental analysis, ¹H NMR and ¹³C NMR. It is confirmed thatβ-sitosterol hemisuccinate and stigmasterol hemisuccinate is the only reaction product, respectively.更多还原