Synthesis of Cyclic Sulfites from Epoxides and Sulfur Dioxide with Silica-Immobilized Homogeneous Catalysts

Authors

  • Dr. Yasumasa Takenaka,

    Corresponding author
    1. National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565 (Japan), Fax: (+81) 29-861-4559
    2. Current address: RIKEN, Biomass Engineering Program, 2-1 Hirosawa, Wako, Saitama 351-0198 (Japan)
    • National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565 (Japan), Fax: (+81) 29-861-4559
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  • Dr. Takahiro Kiyosu,

    1. Wako Pure Chemical Industries, Ltd. 1633 Matoba, Kawagoe, Saitama 350-1101 (Japan)
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  • Dr. Goro Mori,

    1. Wako Pure Chemical Industries, Ltd. 1633 Matoba, Kawagoe, Saitama 350-1101 (Japan)
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  • Dr. Jun-Chul Choi,

    1. National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565 (Japan), Fax: (+81) 29-861-4559
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  • Dr. Norihisa Fukaya,

    1. National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565 (Japan), Fax: (+81) 29-861-4559
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  • Prof. Toshiyasu Sakakura,

    1. National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565 (Japan), Fax: (+81) 29-861-4559
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  • Prof. Hiroyuki Yasuda

    Corresponding author
    1. National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565 (Japan), Fax: (+81) 29-861-4559
    • National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565 (Japan), Fax: (+81) 29-861-4559
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Abstract

Quaternary ammonium- and amino-functionalized silica catalysts have been prepared for the selective synthesis of cyclic sulfites from epoxides and sulfur dioxide, demonstrating the effects of immobilizing the homogeneous catalysts on silica. The cycloaddition of sulfur dioxide to various epoxides was conducted under solvent-free conditions at 100 °C. The quaternary ammonium- and amino-functionalized silica catalysts produced cyclic sulfites in high yields (79–96 %) that are comparable to those produced by the homogeneous catalysts. The functionalized silica catalysts could be separated from the product solution by filtration, thereby avoiding the catalytic decomposition of the cyclic sulfite products upon distillation of the product solution. Heterogenization of a homogeneous catalyst by immobilization can, therefore, improve the efficiency of the purification of crude reaction products. Despite a decrease in catalytic activity after each recycling step, the heterogeneous pyridine-functionalized silica catalyst provided high yields after as many as five recycling processes.

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