1,3-Dimethylimidazolium-2-carboxylate: a zwitterionic salt for the efficient synthesis of vicinal diols from cyclic carbonates
Sun, Jian; Yao, Xiaoqian; Cheng, Weiguo; Zhang, Suojiang
刊名GREEN CHEMISTRY
2014
卷号16期号:6页码:3297-3304
关键词FUNCTIONALIZED IONIC LIQUID N-HETEROCYCLIC CARBENE ETHYLENE-GLYCOL ASYMMETRIC-SYNTHESIS DIMETHYL CARBONATE MICHAEL ADDITION HIGHLY EFFICIENT CO2 HYDROGENATION 1 2-DIOLS
ISSN号1463-9262
其他题名Green Chem.
中文摘要The development of efficient, cheap and recyclable catalysts for reactions under mild reaction conditions is a very attractive topic in green chemistry. Herein, a series of basic ionic liquids (ILs) were investigated as catalysts for the synthesis of vicinal diols via the hydrolysis of cyclic carbonates in order to improve this kind of synthetic process. The effects of the IL structure, the molar ratio of cyclic carbonate to water, and various reaction parameters on the catalytic performance were investigated in detail. It was found that 1,3-dimethylimidazolium-2-carboxylate, a simple halogen-free zwitterionic catalyst, showed high activity (a space-time yield of 1086 h(-1)) and excellent selectivity for the preparation of ethylene glycol via the hydrolysis of ethylene carbonate. The catalyst could be reused over six times without obvious loss of catalytic activity. Also, it was applicable to a variety of cyclic carbonates for the production of their corresponding vicinal diols with high yields and selectivities. A possible catalytic cycle for this kind of catalytic process was proposed based on the experimental results, NMR spectroscopy and theoretical calculations. This reaction protocol opens a new possibility for chemical synthesis as a substitution for traditional base or basic ILs.
英文摘要The development of efficient, cheap and recyclable catalysts for reactions under mild reaction conditions is a very attractive topic in green chemistry. Herein, a series of basic ionic liquids (ILs) were investigated as catalysts for the synthesis of vicinal diols via the hydrolysis of cyclic carbonates in order to improve this kind of synthetic process. The effects of the IL structure, the molar ratio of cyclic carbonate to water, and various reaction parameters on the catalytic performance were investigated in detail. It was found that 1,3-dimethylimidazolium-2-carboxylate, a simple halogen-free zwitterionic catalyst, showed high activity (a space-time yield of 1086 h(-1)) and excellent selectivity for the preparation of ethylene glycol via the hydrolysis of ethylene carbonate. The catalyst could be reused over six times without obvious loss of catalytic activity. Also, it was applicable to a variety of cyclic carbonates for the production of their corresponding vicinal diols with high yields and selectivities. A possible catalytic cycle for this kind of catalytic process was proposed based on the experimental results, NMR spectroscopy and theoretical calculations. This reaction protocol opens a new possibility for chemical synthesis as a substitution for traditional base or basic ILs.
WOS标题词Science & Technology ; Physical Sciences
类目[WOS]Chemistry, Multidisciplinary
研究领域[WOS]Chemistry
关键词[WOS]FUNCTIONALIZED IONIC LIQUID ; N-HETEROCYCLIC CARBENE ; ETHYLENE-GLYCOL ; ASYMMETRIC-SYNTHESIS ; DIMETHYL CARBONATE ; MICHAEL ADDITION ; HIGHLY EFFICIENT ; CO2 ; HYDROGENATION ; 1,2-DIOLS
收录类别SCI ; CCR
原文出处://WOS:000336836100045
语种英语
WOS记录号WOS:000336836100045
公开日期2014-08-28
内容类型期刊论文
版本出版稿
源URL[http://ir.ipe.ac.cn/handle/122111/10962]  
专题过程工程研究所_研究所(批量导入)
作者单位Chinese Acad Sci, Beijing Key Lab Ion Liquids Clean Proc, Inst Proc Engn, State Key Lab Multiphase Complex Syst, Beijing 100190, Peoples R China
推荐引用方式
GB/T 7714
Sun, Jian,Yao, Xiaoqian,Cheng, Weiguo,et al. 1,3-Dimethylimidazolium-2-carboxylate: a zwitterionic salt for the efficient synthesis of vicinal diols from cyclic carbonates[J]. GREEN CHEMISTRY,2014,16(6):3297-3304.
APA Sun, Jian,Yao, Xiaoqian,Cheng, Weiguo,&Zhang, Suojiang.(2014).1,3-Dimethylimidazolium-2-carboxylate: a zwitterionic salt for the efficient synthesis of vicinal diols from cyclic carbonates.GREEN CHEMISTRY,16(6),3297-3304.
MLA Sun, Jian,et al."1,3-Dimethylimidazolium-2-carboxylate: a zwitterionic salt for the efficient synthesis of vicinal diols from cyclic carbonates".GREEN CHEMISTRY 16.6(2014):3297-3304.
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