Chem. J. Chinese Universities ›› 2009, Vol. 30 ›› Issue (9): 1798.

• Articles • Previous Articles     Next Articles

Synthesis of Diphenyl Carbonate from the Transesterification Catalyzed by Dibutyltin Sulfonates

DU Zhi-Ping1,2* , XIAO Yan-Hua2, WANG Gong-Ying1   

  1. 1. Chengdu Institute of Organic Chemistry, Chinese Academy of Science, Chengdu 610041, China;
    2. Hubei Key Laboratory of Novel Reactor & Green Chemical Technology, Key Laboratory for Green Chemical Process of Ministry of Education, Wuhan Institute of Technology, Wuhan 430073, China
  • Received:2008-11-07 Online:2009-09-10 Published:2009-09-10
  • Contact: DU Zhi-Ping. E-mail: dzpxyhry@126.com
  • Supported by:

    国家“八六三”计划(批准号: 2003AA321010)和绿色化工过程省部共建教育部重点实验室开放基金(批准号: GCP200804)资助.

Abstract:

Effect of different types of acid catalysts on the transesterification of dimethyl carbonate with phenol to diphenyl carbonate was investigated. The results show that the transesterification is the reaction of soft base(phenoxy) binding to hard acid(the carbonyl carbon in dimethyl carbonate), and hard Lewis acids exhibit higher transesterification selectivity than soft Lewis acids, border Lewis acids and Brönsted acids. When n-Bu2SnO was modified by different sulfonic acids, a series of hard Lewis acid catalysts [n-Bu2Sn(OH)OS•(O)2R(H2O)]2[R=p-NH2C6H4(Ⅰ), p-CH3C6H4(Ⅱ), C6H5(Ⅲ), p-ClC6H4(Ⅳ), Me(Ⅴ), CF3(Ⅵ)] were prepared. When they were used as the transesterification catalysts, their catalytic activities were higher than that of n-Bu2SnO because of the strong electron-withdrawing effect of sulfonic groups. And the stronger the electron-withdrawing effect of the substituent on the sulfonic group was, the greater the Lewis acidity of Sn in [n-Bu2Sn(OH)OS(O)2R(H2O)]2 was, the higher the catalytic activity was, but the excess electron-withdrawing effect of the substituent could decrease its transesterification selectivity.

Key words: Transesterification; Dimethyl carbonate; Diphenyl carbonate; Dibutyltin sulfonate

TrendMD: