Preparation of sulfenamides by catalytic oxidation

Claim 1

The process for preparing a sulfenamide by reacting primary or secondary amine of the formula respectively RNH2 and where R and R'' independently are selected from the group consisting of alkyl of 1 to 12 carbon atoms, benzyl, cyclopentyl, cyclohexyl and methylcyclohexyl or taken with the NH, R and R'' together form a heterocycle selected from the group consisting of pyrrolidine, piperidine, methylpiperidine, 2-methyl-5-ethylpiperidine, 2-ethylpiperidine, morpholine, methylmorpholine, dimethylmorpholine, and hexamethylenimine and a compound selected from the group consisting of sodium salt of 2-mercaptobenzothiazole, 2-mercaptobenzothiazole, 2,2''-dithiobis(benzothiazole), alkali metal salt of N-substituted dithiocarbamic acid, N-substituted thiuram disulfide, the nitrogen substitutents of said alkali metal salt of dithiocarbamic acid and thiuram sulfide being selected from the group consisting of alkyl of one to 12 carbon atoms, benzyl, phenyl, tolyl, cyclopentyl, cyclohexyl and methylcyclohexyl or together with the nitrogen constitute a heterocyclic radical selected from the group consisting of piperidino, methylpiperidino, hexamethyleniminyl, morpholino, methylmorpholino, dimethylmorpholino, 2-methyl-5-ethylpiperidino, 2-ethylpiperidino and pyrrolidinyl, the reaction being conducted in reaction medium selected from the group consisting of aqueous, mixed and miscible organic-aqueous, organic and mixed and immiscible organic-aqueous, forming the sulfenamide in the presence of oxygen or air under a pressure of about 10 to 500 psi and an effective amount of cobalt phthalocyanine or cobalt phthalocyanine sulfonate catalyst at a temperature between the range of about 25* C. to about 100* C. and a pH between the range of about 7.5 to about 13.0.