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Sterically controlling 2-carboxylated imidazolium salts for one-step efficient hydration of epoxides into 1,2-diols

文献类型：期刊论文

作者Su, Qian1,3; Tan, Xin1,2; Yao, Xiaoqian1; Ying, Ting1; Dong, Li1,3; Fu, Mengqian1,2; Cheng, Weiguo1,3; Zhang, Suojiang1,3
刊名GREEN CHEMISTRY
出版日期2021-03-18
页码9
ISSN号1463-9262
DOI10.1039/d1gc00788b
英文摘要In order to overcome the disadvantages of excessive water and many byproducts in the conventional process of epoxide hydration into 1,2-diols, 2-carboxylated imidazolium salts were first adopted as efficient catalysts for one-step hydration of epoxides into 1,2-diols. By regulating the cation chain lengths, different steric structures of 2-carboxylated imidazolium salts with chain lengths from C1 to C4 were prepared. The salt with the shortest substituent chain (DMIC) exhibited better thermal stability and catalytic performance for hydration, achieving nearly 100% ethylene oxide (EO) conversion and 100% ethylene glycol (EG) selectivity at 120 degrees C, 0.5 h with just 5 times molar ratio of H2O to EO. Such a tendency is further confirmed and explained by both XPS analysis and DFT calculations. Compared with other salts with longer chains, DMIC has stronger interaction of CO2- anions and imidazolium cations, exhibiting a lower tendency to release CO2- and form HO-CO2-, which can nucleophilically attack and synergistically activate ring-opening of epoxides with imidazolium cations. The strong huge sterically dynamic structure ring-opening transition state slows down the side reaction, and both cations and anions stabilized the transition state imidazolium-EG-HO-CO2-, both of which could avoid excessive hydration into byproducts, explaining the high 1,2-diol yield. Based on this, the cation-anion synergistic mechanism is then proposed.
资助项目Innovation Academy for Green Manufacture, Chinese Academy of Sciences[IAGM-2019-A01] ; Transformational Technologies for Clean Energy and Demonstration, Strategic Priority Research Program of the Chinese Academy of Sciences[XDA 21030500] ; National Natural Science Foundation of China[21890763] ; National Natural Science Foundation of China[21908226] ; National Natural Science Foundation of China[22078329]
WOS研究方向Chemistry ; Science & Technology - Other Topics
语种英语
WOS记录号WOS:000637849300001
出版者ROYAL SOC CHEMISTRY
资助机构Innovation Academy for Green Manufacture, Chinese Academy of Sciences ; Transformational Technologies for Clean Energy and Demonstration, Strategic Priority Research Program of the Chinese Academy of Sciences ; National Natural Science Foundation of China
源URL[http://ir.ipe.ac.cn/handle/122111/48228]  
专题中国科学院过程工程研究所
通讯作者Cheng, Weiguo; Zhang, Suojiang
作者单位1.Chinese Acad Sci, Beijing Key Lab Ionic Liquids Clean Proc, State Key Lab Multiphase Complex Syst, Key Lab Green Proc & Engn,Inst Proc Engn, Beijing 100190, Peoples R China
2.Univ Chinese Acad Sci, Sch Chem & Chem Engn, Beijing 100049, Peoples R China
3.Chinese Acad Sci, Innovat Acad Green Mfg, Beijing 100190, Peoples R China
推荐引用方式
GB/T 7714		 Su, Qian,Tan, Xin,Yao, Xiaoqian,et al. Sterically controlling 2-carboxylated imidazolium salts for one-step efficient hydration of epoxides into 1,2-diols[J]. GREEN CHEMISTRY,2021:9.
APA Su, Qian.,Tan, Xin.,Yao, Xiaoqian.,Ying, Ting.,Dong, Li.,...&Zhang, Suojiang.(2021).Sterically controlling 2-carboxylated imidazolium salts for one-step efficient hydration of epoxides into 1,2-diols.GREEN CHEMISTRY,9.
MLA Su, Qian,et al."Sterically controlling 2-carboxylated imidazolium salts for one-step efficient hydration of epoxides into 1,2-diols".GREEN CHEMISTRY (2021):9.

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来源：过程工程研究所

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