中华医学超声杂志

应用化学 ›› 2011, Vol. 28 ›› Issue (06): 662-666.DOI: 10.3724/SP.J.1095.2011.00435

• 研究论文 • 上一篇    下一篇

离子液体对H2O2氧化环己烯制备反-1,2-环己二醇的催化作用

高飞1,贾颖萍1,崔颖娜1,李长平1,尹静梅1,2*   

  1. (1.大连大学环境与化学工程学院 大连 116622；2.大连大学生物有机省重点实验室 大连 116622)
  • 收稿日期:2010-07-29 修回日期:2010-12-01 出版日期:2011-06-10 发布日期:2011-06-10
  • 通讯作者: 尹静梅，教授; Tel:0411-87402436; Fax:0411-87402499; E-mail:jingmeiyin@yeah.net; 研究方向：有机合成和有机光化学
  • 基金资助:
    国家自然科学基金（21006007）资助项目

Catalytic Oxidation of Cyclohexene to Trans-1,2-cyclohexanediol by H2O2 with the Presence of Ionic Liquids

GAO Fei1, JIA Yingping1, CUI Yingna1, LI Changping1, YIN Jingmei1,2*   

  1. (1.College of Environment and Chemical Engineering,Dalian University,Dalian 116622;
    2.Liaoning Key Laboratory of Bio-Organic Chemistry,Dalian University,Dalian 116622)
  • Received:2010-07-29 Revised:2010-12-01 Published:2011-06-10 Online:2011-06-10
  • Contact: Yin

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摘要：

以H2O2为氧化剂，研究了离子液体为催化剂和溶剂，环己烯氧化生成反-1,2-环己二醇的反应。 考察了不同咪唑型离子液体、反应时间、反应温度和H2O2用量等对产率和选择性的影响， 实验结果表明，在7种咪唑型离子液体催化体系中，阳离子为咪唑环上含有1或2个羧基，阴离子为[PF6]的离子液体催化效果较好。 反应温度为100 ℃，n(H2O2)∶n(Cyclohexene)＝1.1∶1，反应5 h时，离子液体c（0.60 g，2.1 mmol）催化生成的反-1,2-环己二醇的产率和选择性分别为95%和97%，而离子液体f（0.20 g，0.6 mmol）催化生成的反-1,2-环己二醇的产率和选择性分别为84%和90%，从离子液体的用量来看，含2个羧基的离子液体f的催化效率更高。

关键词: 离子液体, 环己烯, 过氧化氢, 反环己二醇

Abstract:

Trans-1,2-cyclohexanediol was synthesized by the oxidation of cyclohexene using H2O2 as the oxidant and ionic liquids(ILs) as the catalyst and solvent. The effects of different imidazolium ionic liquids, reaction time, reaction temperature and the amount of H2O2 on the yield and selectivity of trans-1,2-cyclohexanediol were investigated. The experimental results showed that ionic liquids based on imidazolium cations containing 1~2 carboxyl groups and [PF6] anion exhibited the highest catalytic activities among the seven imidazolium ionic liquids. Under optimized conditions: reaction temperature 100 ℃, n(H2O2)∶n(cyclohexene)=1.1∶1, and reaction time 5 h, the yield and selectivity of trans-1,2-cyclohexanediol were 95% and 97% with IL c(0.60 g, 2.1 mmol) as the catalyst, and 84% and 90% with IL f(0.20 g, 0.6 mmol) as the catalyst, respectively. From the dosage of ionic liquid, it can be seen the catalytic efficiency of IL f containing two carboxyl groups was higher.

Key words: ionic liquids, cyclohexene, Peroxide, trans-cyclohexanediol

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