pH-Dependence of the Aqueous Phase Room Temperature Brønsted Acid-Catalyzed Chemoselective Oxidation of Sulfides with H₂O₂

Hai-Min Shen; Wen-Jie Zhou; Xin Ma; Hong-Ke Wu; Wu-Bin Yu; Ning Ai; Hong-Bing Ji; Hong-Xin Shi; Yuan-Bin She

doi:10.3390/molecules200916709

pH-Dependence of the Aqueous Phase Room Temperature Brønsted Acid-Catalyzed Chemoselective Oxidation of Sulfides with H₂O₂

Molecules. 2015 Sep 14;20(9):16709-22. doi: 10.3390/molecules200916709.

Authors

Hai-Min Shen¹, Wen-Jie Zhou², Xin Ma³, Hong-Ke Wu⁴, Wu-Bin Yu⁵, Ning Ai⁶, Hong-Bing Ji⁷, Hong-Xin Shi⁸, Yuan-Bin She⁹

Affiliations

¹ College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China. haimshen@zjut.edu.cn.
² College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China. zhouwj0716@163.com.
³ College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China. shm190726@hotmail.com.
⁴ College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China. wuhongke@zjut.edu.cn.
⁵ College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China. yuwb@zjut.edu.cn.
⁶ College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China. aining@zjut.edu.cn.
⁷ School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, China. jihb@mail.sysu.edu.cn.
⁸ College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China. shihxin@zjut.edu.cn.
⁹ College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China. sheyb@zjut.edu.cn.

Abstract

A pH-dependence of the Brønsted acid-catalyzed oxidation of sulfides to the corresponding sulfoxides with H₂O₂ is reported for the first time based on our systematic investigation of the catalytic performance of a series of Brønsted acids. For all of the Brønsted acids investigated, the catalytic performances do not depend on the catalyst loading (mol ratio of Brønsted acid to substrate), but rather depend on the pH value of the aqueous reaction solution. All of them can give more than 98% conversion and selectivity in their aqueous solution at pH 1.30, no matter how much the catalyst loading is and what the Brønsted acid is. This pH-dependence principle is a very novel perspective to understand the Brønsted-acid catalysis system compared with our common understanding of the subject.

Keywords: Brønsted acid; oxidation; pH-dependence; sulfide; sulfoxide.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acids / chemistry*
Catalysis
Hydrogen Peroxide / chemistry*
Hydrogen-Ion Concentration
Oxidants / chemistry*
Oxidation-Reduction
Sulfides / chemistry*
Temperature
Water / chemistry*

Substances

Acids
Oxidants
Sulfides
Water
Hydrogen Peroxide