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

• Published in: ChemSusChem Vol. 5; no. 1; pp. 194 - 199
• Main Authors: Takenaka, Yasumasa, Kiyosu, Takahiro, Mori, Goro, Choi, Jun-Chul, Fukaya, Norihisa, Sakakura, Toshiyasu, Yasuda, Hiroyuki
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 09.01.2012; WILEY‐VCH Verlag
• Subjects: Amines - chemistry; Catalysis; Chemistry Techniques, Synthetic - methods; cycloaddition; Epoxy Compounds - chemistry; heterogeneous catalysis; immobilization; mesoporous materials; Quaternary Ammonium Compounds - chemistry; Silicon Dioxide - chemistry; Sulfites - chemical synthesis; Sulfites - chemistry; Sulfur Dioxide - chemistry; sulfur heterocycles
• ISSN: 1864-5631; 1864-564X
• DOI: 10.1002/cssc.201100492

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. Immobilized for crimes of pyrolysis: Quaternary ammonium‐ and amino‐functionalized silica catalysts promote the cycloaddition of sulfur dioxide to epoxides to produce cyclic sulfites in high yields (79–96 %) that are comparable to those with the homogeneous catalysts. Separation of the functionalized silica catalyst from the product solution by filtration avoids pyrolysis of the cyclic sulfites during purification by distillation.