盐酸-三氯化铁催化芝麻素差向异构化合成细辛素及机理探讨

doi:10.11949/j.issn.0438-1157.20151447

化工学报 ›› 2015, Vol. 66 ›› Issue (S2): 455-460.DOI: 10.11949/j.issn.0438-1157.20151447

• 材料化学工程与纳米技术 • 上一篇下一篇

盐酸-三氯化铁催化芝麻素差向异构化合成细辛素及机理探讨

汪学德^1,4, 黄雪², 刘帅⁴, 崔英德^1,3

1. 广东工业大学轻工化工学院, 广东广州 510006;
2. 仲恺农业工程学院化学化工学院, 广东广州 510225;
3. 广州科技职业技术学院, 广东广州 510550;
4. 河南工业大学粮油食品学院, 河南郑州 450001

收稿日期:2015-07-14 修回日期:2015-07-16 出版日期:2015-08-31 发布日期:2015-08-31
通讯作者: 崔英德
基金资助:
国家自然科学基金项目(31271884,31401526);现代农业产业技术体系建设项目(CARS15-1-10)。

Catalytic epimerization of hydrochloric acid-ferric chloride of sesamin to synthesis of asarinin and its mechanism

WANG Xuede^1,4, HUANG Xue², LIU Shuai⁴, CUI Yingde^1,3

1. School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, Guangdong, China;
2. College of Chemistry and Chemical Engineering, Zhongkai University of Agriculture and Engineering, Guangzhou 510225, Guangdong, China;
3. Guangzhou Vocational College of Science and Technology, Guangzhou 510550, Guangdong, China;
4. College of Food Science and Technology, Henan University of Technology, Zhengzhou 450001, Henan, China

Received:2015-07-14 Revised:2015-07-16 Online:2015-08-31 Published:2015-08-31
Supported by:
supported by the National Natural Science Foundation of China(31271884,31401526),Modern Agricultural Industry Technology System Construction Project(CARS15-1-10).

摘要/Abstract

摘要：

分别以盐酸、三氯化铁、盐酸-三氯化铁作为催化剂,研究芝麻素差向异构化合成细辛素的条件并探讨差向异构化机理,采用NMR、MS方法对合成物进行结构鉴定。结果显示:单独使用盐酸作为催化剂,盐酸体积分数为20%时催化反应达到平衡;单独使用三氯化铁作为催化剂,会发生水解反应,致使催化反应终止;以盐酸-三氯化铁作为联合催化剂,使用较少的量(质量分数0.05%~0.5%),反应温度控制在体系中乙醇沸点之上,10 min内就能够达到很好的催化效果。联合催化剂可降低反应体系的活化能,加快了芝麻素异构化为细辛素的进程。

关键词: 芝麻素, 细辛素, 化学反应, 合成, 差向异构化, 催化剂, 催化机理

Abstract:

Using hydrochloric acid,ferric chloride and hydrochloric acid-ferric trichloride as catalyst,the epimerization of sesamin and asarinin were preliminary investigated and attempt to probe into the possible mechanism.The structure of the composite was identified by NMR and MS.The results showed that the reaction reach to equilibrium with 20% hydrochloric acid;it didn't work with only ferric trichloride as catalyst which was easy to hydrolysis; Using hydrochloric acid-ferric chloride as catalyst,use less quantity(the mass fraction of 0.05%-0.5%)can achieve better catalytic effect,reaction temperature should be above the boiling point of the reaction system of ethanol,reaction can be completed within 10 min.Combined catalyst to reduce the activation energy of the reaction system,accelerate the sesamin isomerization process for asarinin.

Key words: sesamin, asarinin, chemical reaction, synthesis, epimerization, catalyst, catalytic mechanism

中图分类号:

汪学德, 黄雪, 刘帅, 崔英德. 盐酸-三氯化铁催化芝麻素差向异构化合成细辛素及机理探讨[J]. 化工学报, 2015, 66(S2): 455-460.

WANG Xuede, HUANG Xue, LIU Shuai, CUI Yingde. Catalytic epimerization of hydrochloric acid-ferric chloride of sesamin to synthesis of asarinin and its mechanism[J]. CIESC Journal, 2015, 66(S2): 455-460.

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盐酸-三氯化铁催化芝麻素差向异构化合成细辛素及机理探讨

Catalytic epimerization of hydrochloric acid-ferric chloride of sesamin to synthesis of asarinin and its mechanism

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