功能化离子液体催化合成甘油单月桂酸酯

doi:10.11949/j.issn.0438-1157.20141423

化工学报 ›› 2015, Vol. 66 ›› Issue (S1): 209-215.DOI: 10.11949/j.issn.0438-1157.20141423

• 催化、动力学与反应器 • 上一篇下一篇

功能化离子液体催化合成甘油单月桂酸酯

王松, 张争艳, 常欠欠, 李三喜, 张林楠

沈阳工业大学理学院, 辽宁沈阳 110870

收稿日期:2014-09-22 修回日期:2014-09-27 出版日期:2015-06-30 发布日期:2015-06-30
通讯作者: 张争艳
基金资助:
辽宁省聚合物催化合成技术重点实验室专项基金项目(2012-36)。

Synthesis of glycerol monolaurate using functionalized ionic liquids catalysts

WANG Song, ZHANG Zhengyan, CHANG Qianqian, LI Sanxi, ZHANG Linnan

School of Science, Shenyang University of Technology, Shenyang 110870, Liaoning, China

Received:2014-09-22 Revised:2014-09-27 Online:2015-06-30 Published:2015-06-30
Supported by:
supported by the Key Laboratory for Catalyst Synthesis of Polymer of Liaoning Province (2012-36).

摘要/Abstract

摘要：

合成了由吡啶、N-甲基咪唑、N-甲基-2-吡咯烷酮提供有机阳离子, 磷钨酸、对甲苯磺酸提供阴离子的6种离子液体。使用NMR、FT-IR和TG对离子液体表征, 并考察它们催化甘油与月桂酸酯化的催化效果。结果表明, 这些离子液体都具有较好的热稳定性, 以1-(丁基-4-磺酸基)-3-甲基咪唑磷钨酸盐离子液体的热稳定性最好。在最佳条件使用离子液体催化甘油与月桂酸反应时, 阴离子的种类对月桂酸的转化率影响较大, 以对甲苯磺酸为阴离子的离子液体催化反应时, 月桂酸转化率较以磷钨酸为阴离子的离子液体的高;1-(丁基-4-磺酸基)-3-甲基咪唑对甲苯磺酸盐离子液体做催化剂时甘油单月桂酸酯的产率最高。催化剂重复使用性方面, 离子液体重复使用5次催化活性没有明显变化。

关键词: 甘油单月桂酸酯, 离子液体, 功能化, 酯化, 催化剂

Abstract:

Six ionic liquids based on pyridine (Py), 1-methylimidazole (MIM), N-methyl-2-pyrrolidinone(NMP) cations were prepared by coupling corresponding SO₃H-functionalized zwitterion ionic complex with different counterpart anions including H₃PW₁₂O₄₀ and p-toluenesulfonic acid (PTSA). The obtained ionic liquids were well characterized by FT-IR, TG, ¹H NMR, ¹³C NMR methods and then these ionic liquids were deployed in the esterification reaction of glycerol with lauric acid under the condition without organic solvent. The effects of various key reaction parameters including reaction temperature, glycerol/lauric acid molar ratio, molar ratio of ionic liquid to lauric acid and the type of catalysts on the acid conversion and yield of glycerol monolaurate were discussed. The results indicated that all the ionic liquids exhibit good thermal stability and compared with other ionic liquids, [MIMBS]₃PW₁₂O₄₀ ionic liquid has the best thermal stability. When [MIMBS][PTSA] ionic liquid was used to optimize esterification reaction parameters, the optimum reaction conditions were established as follows: glycerol/lauric acid ratio of 4, amount of catalyst of 1% molar to lauric acid, reaction time of 3 h at 130℃. When used under the optimized reaction condition, all the ionic liquids exhibit excellent catalytic activity, the acid conversions are all above 92% and the highest yield of glycerol monolaurate of 64.6% has been achieved. In addition, comparing the structure of the investigated ionic liquids, it can be found that under the condition of lauric acid being catalyzed by the ionic liquids with PTSA anion, the conversion is higher than that when lauric acid was catalyzed by ionic liquids with H₃PW₁₂O₄₀ anion. With respect to the yield of glycerol monolaurate, when the reaction was catalyzed by ionic liquids, [MIMBS][PTSA] gives the highest yield. As to the reusability behavior of these ionic liquids, the results indicated that all these catalysts can be reused up to five times without noticeable loss of catalytic activity.

Key words: glycerol monolaurate, ionic liquids, functionalization, esterification, catalyst

中图分类号:

O643.3

王松, 张争艳, 常欠欠, 李三喜, 张林楠. 功能化离子液体催化合成甘油单月桂酸酯[J]. 化工学报, 2015, 66(S1): 209-215.

WANG Song, ZHANG Zhengyan, CHANG Qianqian, LI Sanxi, ZHANG Linnan. Synthesis of glycerol monolaurate using functionalized ionic liquids catalysts[J]. CIESC Journal, 2015, 66(S1): 209-215.

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功能化离子液体催化合成甘油单月桂酸酯

Synthesis of glycerol monolaurate using functionalized ionic liquids catalysts

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