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Low-Cost Polymer-Supported Quaternary Ammonium Salts as High-Efficiency Catalysts for Cycloaddition of CO2 to Epoxides

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Abstract

Polystyrene grafted with quaternary ammonium salts were obtained by direct quaternarization of chloromethylated polystyrene with N,N-dimethylethylamine, N,N-dimethylglycine (denoted as PS-QNS and PS-CQNS, respectively). These two polymer-supported ionic liquids were found to show high catalytic efficiency towards the cycloaddition of CO2 to epoxides. The effects of catalyst amount, reaction temperature, initial CO2 pressure, and reaction time on the yield of cyclic carbonates were investigated systematically. Under the optimal reaction conditions (150 °C, initial CO2 pressure 2.0 MPa and 5 h), propylene carbonate yield and selectivity in the cycloaddition of CO2 to propylene oxide over PS-CQNS were 96.2 and 99.3 % whereas those over PS-QNS were 97.9 and 99.5 %, respectively. It was observed that the reusability of PS-QNS was excellent. From the viewpoint of industrial application, PS-QNS is attractive in terms of catalytic efficiency, cost and simplicity in preparation.

Graphical Abstract

Polystyrene bearing quaternary ammonium salt ionic liquids (denoted as PS-QNS and PS-CQNS) were fabricated and evaluated for solventless synthesis of cyclic carbonates from CO2 and epoxides. The catalysts are low in cost and simple to prepare, and show good activity, selectivity, stability and reusability towards the cycloaddition reaction.

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Acknowledgments

This study was financially supported by the program for New Century Excellent Talents in Universities (NCET-10-0371), NSF of Hunan Province (10JJ1003), and the Fundamental Research Funds for the Central Universities. C. T. Au thanks the Hunan University for an adjunct professorship.

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Authors and Affiliations

  1. State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, Hunan, China

    Yuan-Yuan Zhang, Lang Chen, Shuang-Feng Yin, Sheng-Lian Luo & Chak-Tong Au

  2. Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong, China

    Chak-Tong Au

Authors
  1. Yuan-Yuan Zhang
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  2. Lang Chen
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  3. Shuang-Feng Yin
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  4. Sheng-Lian Luo
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  5. Chak-Tong Au
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Correspondence to Shuang-Feng Yin.

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Zhang, YY., Chen, L., Yin, SF. et al. Low-Cost Polymer-Supported Quaternary Ammonium Salts as High-Efficiency Catalysts for Cycloaddition of CO2 to Epoxides. Catal Lett 142, 1376–1381 (2012). https://doi.org/10.1007/s10562-012-0909-y

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  • DOI: https://doi.org/10.1007/s10562-012-0909-y

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