Alkyl alkanethiolsulfonates have been prepared by electrochemical oxidation of the corresponding alkyl disulfide (CA 101:110070j (1984), abstract Machion et al., An. Simo. Bras. Electroquim. Electroanal., 4th, 289-292 (1984)) and electrochemical reduction of the corresponding sulfonyl chloride and sodium salt of the sulfonic acid (CA 100:87666b (1984), abstracting Polish PL 117,553).
Various oxidizing agents have been employed in the preparation of alkyl alkanethiolsulfonates from the corresponding disulfides. These include, m-chloroperbenzoic acid (Bhattacharya et al., J. Org. Chem. 43(13) 2728-2730 (1978)); organic hydroperoxide in the presence of a Mo(VI)-containing catalyst (U.S. Pat. No. 3,670,002); air in the presence of various transition metal halides and oxyhalides (CA 76:3397q (1972), abstracting French Patent No. 2,044,265); and nitrogen dioxide (U.S. Pat. No. 3,153,078).
U.S. Pat. No. 3,365,480 describes the preparation of various nitrogen-containing thiolsulfonates by the oxidation of the acid salts of the corresponding disulfide with hydrogen peroxide in a polar solvent such as an alcohol or an organic acid. Propyl propanethiolsulfonate has been identified by thin layer chromatography in the product mixture resulting from the oxidation of dipropyl disulfide by hydrogen peroxide in acetic acid solution (Nogami et al., Chem. Pharm. Bull. 19(12), 2472-77 (1971)). In cases where an organic solvent such as acetic acid is employed in conjunction with hydrogen peroxide, the de facto oxidizing agent is likely to be the corresponding peracid. In such instances, and, in general, when an organic solvent is employed, there is a need to recover and recycle the solvent to make the process economic.
In other prior art processes, exotic and expensive oxidizing agents such as m-chloroperbenzoic acid, sodium metaperiodate, and the like are utilized. Commercial application of such processes is questionable.
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