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An alternative synthetic process of p-acetaminobenzenesulfonyl chloride through combined chlorosulfonation by HClSO3 and PCl5

Shiyu Tan, Yang Yang, Ziping Luo, Shuo Zhao, Dafu Huang, Jun Zhang, Lichun Dong, and Gang Wang

School of Chemistry and Chemical Engineering, Chongqing University, 400044 Chongqing, China

 

E-mail: lcdong72@gmail.com

Abstract: p-Aminobenzene sulfonamide (sulfanilamide, SN) is the simplest and most-used sulfonamide medicine. The key step of SN production via the commonly used chlorosulfonic acid routine is the synthesis of p-acetaminobenzenesulfonyl chloride (P-ASC). A large amount of HSO3Cl has to be used in the traditional process, which results in serious environmental problems. In this study, an alternative chlorosulfonic acid process to synthesize P-ASC was investigated by partially substituting HSO3Cl by PCl5 as the chlorination agent. Compared with the traditional process, the molar ratio of HSO3Cl to acetanilide (the main raw material) can be decreased from 4.96 to 2.1 using CCl4 as the diluent; also, addition of a small amount of NH4Cl was found to significantly increase the P-ASC yield. Operating conditions of the reaction were studied first by single-factor experiments and later by orthogonal experiments to obtain optimum operating conditions under which the P-ASC yield can reach as high as 86.3 %.

Keywords: p-aminobenzene sulfone chloride – chlorosulfonation process – HSO3Cl – PCl5 – p-aminobenzene sulfonamide

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-011-0026-1

 

Chemical Papers 65 (4) 510–518 (2011)

Tuesday, October 15, 2019

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