Pyrolysis of p-Toluenesulfonamide

Abstract

Upon heating p-toluenesulfonamide [1] at 240 260°C for 48 h, di-p-toly1 disulfide [2] S-(p-toly1) p-toluenethiosulfonate [3], di-p-tolyl sulfide [4], p-sulfamoylbenzoic acid [5], ammonium p-toluenesulfonate [7], and ammonium sulfate [8] were obtained as a result of thermal decomposition. p-Toluenthiol [6], toluene [9], and ammonia were also detected. Mechanism for predominant formation of [2] was described. Owing to relatively high stability of [1], extent of pyrolysis was less than 28% under the present reaction conditions. No thermal decomposition occurred below 200°C.