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Sterically controlling 2-carboxylated imidazolium salts for one-step efficient hydration of epoxides into 1,2-diols
Su, Qian1,2; Tan, Xin1,3; Yao, Xiaoqian1; Ying, Ting1; Dong, Li1,2; Fu, Mengqian1,3; Cheng, Weiguo1,2; Zhang, Suojiang1,2
2021-03-18
Source PublicationGREEN CHEMISTRY
ISSN1463-9262
Pages9
AbstractIn 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.
DOI10.1039/d1gc00788b
Language英语
Funding ProjectInnovation 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 Research AreaChemistry ; Science & Technology - Other Topics
WOS SubjectChemistry, Multidisciplinary ; Green & Sustainable Science & Technology
Funding OrganizationInnovation 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
WOS IDWOS:000637849300001
PublisherROYAL SOC CHEMISTRY
Citation statistics
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/48229
Collection中国科学院过程工程研究所
Corresponding AuthorCheng, Weiguo; Zhang, Suojiang
Affiliation1.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.Chinese Acad Sci, Innovat Acad Green Mfg, Beijing 100190, Peoples R China
3.Univ Chinese Acad Sci, Sch Chem & Chem Engn, Beijing 100049, Peoples R China
Recommended Citation
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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