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Zinc-Accelerated Cycloaddition of Carbon Dioxide to Styrene Oxide Catalyzed by Pyrrolidinopyridinium Iodides

Topics in Catalysis volume 57, pages 953–959 (2014)Cite this article

Abstract

The addition of ZnI2 drastically accelerated the cycloaddition of carbon dioxide to styrene oxide catalyzed by pyrrolidinopyridinium iodides. In the presence of ZnI2, the styrene carbonate yield reached up to 89 % in 7 h at 100 °C under 1 atm of CO2. The rate constant increased by greater than three-fold by the addition of ZnI2. Studies of reaction kinetics in addition to high resolution mass and NMR analysis demonstrated that the primary active species consists of two or more pyrrolidinopyridinium cations combined with ZnI4 2− anion.

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Acknowledgments

This work was supported by Advanced Catalytic Transformation program for Carbon utilization (ACT-C), a Grant-in-Aid for Young Scientists (A) (24686092), and The UBE Foundation. The authors thank Center for Advanced Materials Analysis (Suzukakedai), Technical Department, Tokyo Institute of Technology for high resolution mass analysis.

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Authors and Affiliations

  1. Department of Environmental Chemistry and Engineering, Interdisciplinary Graduate School of Science and Engineering, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, 226-8502, Japan

    Ken Motokura, Akimitsu Miyaji & Toshihide Baba

  2. Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, Japan

    Shintaro Itagaki

  3. Innovation Research Center for Fuel Cells, Department of Engineering Science, Graduate School of Information Engineering Science, The University of Electro-Communications, 1-5-1 Chofugaoka, Chofu, Japan

    Yasuhiro Iwasawa

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  1. Ken Motokura
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  2. Shintaro Itagaki
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  3. Yasuhiro Iwasawa
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  4. Akimitsu Miyaji
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  5. Toshihide Baba
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Correspondence to Ken Motokura.

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Motokura, K., Itagaki, S., Iwasawa, Y. et al. Zinc-Accelerated Cycloaddition of Carbon Dioxide to Styrene Oxide Catalyzed by Pyrrolidinopyridinium Iodides. Top Catal 57, 953–959 (2014). https://doi.org/10.1007/s11244-014-0257-9

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  • DOI: https://doi.org/10.1007/s11244-014-0257-9

Keywords

  • Cyclic carbonate
  • Carbon dioxide
  • Styrene oxide
  • Zinc salt
  • Pyrrolidinopyridinium iodide