It is produced by the reaction of 2-aminothiophenol and carbon disulfide: This method was developed by the discoverer of the compound. Other routes developed by Hoffmann included the reactions of carbon disulfide with 2-aminophenol and of sodium hydrosulfide with chlorobenzothiazole. Further synthetic advances were reported in the 1920s that included demonstration that phenyldithiocarbamates pyrolyze to benzothiazole derivative. Oxidation gives the disulfide. This can react with amines to give sulfenamide derivatives such as DCBS and 2-morpholinodithiobenzothiazole. All of these compounds are important in sulphur vulcanization, where they act as accelerators.
Uses
Using MBT, rubber vulcanizes with less sulfur and at milder temperatures, both factors give a stronger product. This effect was reported in 1921 by workers at Pirelli and in 1920 by Lorin B. Sebrell at Goodyear Tire & Rubber. In polymerization, it finds use as a radical polymerization inhibitor, chain transfer agent, reforming agent, and additive for photoinitiators. The compound has also been used in the past in the gold-mining industry for the froth flotation of gold from ore residue as part of the extraction process. This compound is used as cooling towerbiocide. Sodium salt is used as a biocide and preservative in adhesives, paper, textiles. Often found together with sodium dimethyldithiocarbamate as e.g. Vancide 51. Zinc salt is used as a secondary accelerator in latex foam vulcanization. It can be added to oil-based hydraulic fluids, heat-transfer fluids, cutting fluids and other mixtures as a corrosion inhibitor, effective for copper and copper alloys. It is also used in veterinary dermatology. Here it is employed in topical preparations to treat acute moist dermatitis, "hot spots". In electroplating it is used as a brightener for copper sulfate baths, at about 50-100 milligrams/liter. Also can be added to silver cyanide baths.
Safety
Studies have identified it as a potiential human carcinogen. In 2016, it was identified by the World Health Organization as probably carcinogenic to humans. It causes allergic contact dermatitis. The derivative morpholinylmercaptobenzothiazole is a reported allergen in protective gloves, including latex, nitrile, and neoprene gloves. It becomes air-borne as a result of wear on car tires, and is able to be inhaled.
