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1,3-Dimethylimidazolium-2-carboxylate: a zwitterionic salt for the efficient synthesis of vicinal diols from cyclic carbonates
Alternative TitleGreen Chem.
Sun, Jian; Yao, Xiaoqian; Cheng, Weiguo; Zhang, Suojiang
2014
Source PublicationGREEN CHEMISTRY
ISSN1463-9262
Volume16Issue:6Pages:3297-3304
AbstractThe 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.; 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.
KeywordFunctionalized Ionic Liquid N-heterocyclic Carbene Ethylene-glycol Asymmetric-synthesis Dimethyl Carbonate Michael Addition Highly Efficient Co2 Hydrogenation 1 2-diols
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
DOI10.1039/c4gc00279b
URL查看原文
Indexed BySCI ; CCR
Language英语
WOS KeywordFUNCTIONALIZED IONIC LIQUID ; N-HETEROCYCLIC CARBENE ; ETHYLENE-GLYCOL ; ASYMMETRIC-SYNTHESIS ; DIMETHYL CARBONATE ; MICHAEL ADDITION ; HIGHLY EFFICIENT ; CO2 ; HYDROGENATION ; 1,2-DIOLS
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000336836100045
Citation statistics
Cited Times:21[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Version出版稿
Identifierhttp://ir.ipe.ac.cn/handle/122111/10962
Collection研究所(批量导入)
AffiliationChinese Acad Sci, Beijing Key Lab Ion Liquids Clean Proc, Inst Proc Engn, State Key Lab Multiphase Complex Syst, Beijing 100190, Peoples R China
Recommended Citation
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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