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Bisimidazolium Tungstate Ionic Liquids: Highly Efficient Catalysts for the Synthesis of Linear Organic Carbonates by the Reaction of Ethylene Carbonate with Alcohols

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Abstract

A series of bisimidazolium tungstate ionic liquids were synthesized and applied to catalyze the reaction of ethylene carbonate (EC) with alcohols. A detailed investigation was carried out on the relationship between catalyst structures and catalytic activities. The result showed that 1-butyl-3-methyl-bisimidazolium tungstate ([Bmim]2WO4) containing double C2–H in bisimidazolium and WO42− had more effectively catalytic performance than other bisimidazolium tungstate and conventional imidazolium salt (OAc−, Cl−, Br−). Under the optimized conditions of 1:15 molar ratio of EC and ethanol, 5 mol% [Bmim]2WO4, 85 °C and 0.5 h, the yield of diethyl carbonate (DEC) was nearly 100%. The detailed DFT calculations and NMR spectroscopy indicated that the high catalytic activity of [Bmim]2WO4 was not only because the strong nucleophilic ability of WO42− could activate ethanol, but also the special structure of double C2–H in bisimidazolium could cooperatively activate EC. The reaction was catalyzed by synergistic effect in double C2–H and WO42− of [Bmim]2WO4. In addition, [Bmim]2WO4 could be used seven times without significant loss of catalytic activity.

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Acknowledgements

We thank the National Natural Science Foundation of China (22169017), Applied Basic Research Program of Shangrao City (2021F001) and Project of Shangrao Normal University (202130) for financial support.

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Authors and Affiliations

  1. Shangrao Key Laboratory of Ecotoxicology, School of Chemistry and Environmental Science, Shangrao Normal University, Shangrao, 334001, China

    Shi Wu, Jie Huang, Yingting Wang, Huilin Tao & Zhongliang Yu

  2. State Key Laboratory of Photocatalysis On Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou, 350116, Fujian, China

    Yongfan Zhang

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  1. Shi Wu
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  2. Jie Huang
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  4. Huilin Tao
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Correspondence to Shi Wu.

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Wu, S., Huang, J., Wang, Y. et al. Bisimidazolium Tungstate Ionic Liquids: Highly Efficient Catalysts for the Synthesis of Linear Organic Carbonates by the Reaction of Ethylene Carbonate with Alcohols. Catal Lett 153, 62–73 (2023). https://doi.org/10.1007/s10562-022-03969-6

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