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Efficient Solvent-Free Synthesis of Cyclic Carbonates from the Cycloaddition of Carbon Dioxide and Epoxides Catalyzed by New Imidazolinium Functionalized Metal Complexes Under 0.1 MPa

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Abstract

A series of imidazolinium functionalized metal complexes were prepared as efficient and recyclable homogeneous catalysts for the synthesis of cyclic carbonates via the coupling reaction of carbon dioxide and epoxides in the absence of co-catalysts and solvent. Due to the synergistic effect between the metal center as Lewis acid and the imidazolinium groups with halide anions as Lewis base, these catalysts exhibited excellent catalytic capability. Particularly, high turnover frequency (TOF) values of (1174, 1240 and 1262 h−1) for bifunctional catalysts (2c, 2i and 2j, respectively) were achieved via adjusting reaction parameters. These catalysts also showed excellent catalytic performances under atmospheric pressure. Recyclability test showed that this kind of bifunctional catalyst can be easily recovered and reused for at least five times without dramatic loss of activity and selectivity. The optimum reaction conditions were also screened as (120 °C, 1.0 MPa CO2 and 2 h). The catalyst could also be applied to a variety of substrates and be used for a long time with high catalytic activities. We also performed the Kinetic studies, which suggested that the activity of catalysts following the order I− > Br− > Cl−. Moreover, a plausible reaction mechanism by imidazolinium functionalized metal complexes was proposed.

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Acknowledgements

We acknowledge gratefully the financial support from National Natural Science Foundation of China (No. 51073175), Natural Science Foundation of Hubei province, P. R China (No. 2016CKB704) and the Fundamental Research Funds for the Central Universities, South-Central University for Nationalities (CZT19002). Authors are also grateful to the financial support of Beijing National Laboratory for Molecular Sciences (BNLMS201827).

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Author notes

  1. Peng Yu is a co-first author.

Authors and Affiliations

  1. Key Laboratory of Catalysis and Energy Materials Chemistry of Ministry of Education & Hubei Key Laboratory of Catalysis and Materials Science, Key Laboratory of Analytical Chemistry of the State Ethnic Affairs Commission, National Demonstration Center for Experimental Ethnopharmacology Education, College of Chemistry and Materials Science, South-Central University for Nationalities, Wuhan, 430074, People’s Republic of China

    Qian Zhang, Peng Yu, Bo Lei, Hai-Jian Yang, Juncheng Hu, Lihua Wang, Tengfei Zhou & Qingqing Jiang

  2. Hubei Key Laboratory of Biomass Fibers and Eco-Dyeing & Finishing, College of Chemistry and Chemical Engineering, Wuhan Textile University, Wuhan, 430200, People’s Republic of China

    Junjiang Zhu

  3. Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100049, People’s Republic of China

    Buxing Han

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  1. Qian Zhang
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Zhang, Q., Yu, P., Lei, B. et al. Efficient Solvent-Free Synthesis of Cyclic Carbonates from the Cycloaddition of Carbon Dioxide and Epoxides Catalyzed by New Imidazolinium Functionalized Metal Complexes Under 0.1 MPa. Catal Lett 150, 2537–2548 (2020). https://doi.org/10.1007/s10562-020-03163-6

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