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Mercaptobenzothiazole

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Mercaptobenzothiazole

Adams 2 mercaptobenzothiazole review


2-Mercaptobenzothiazole (MBT) is an organosulfur compound with the formula C6H4NSCSH. The molecule consists of a benzene ring fused to a 2-mercaptothiazole ring. It is used in the vulcanization of rubber.

Contents

Synthesis and reactions

It is produced by the reaction of 2-aminothiophenol and carbon disulfide:

C6H4(NH2)SH + CS2 → C6H4NSCSH + H2S

It oxidizes to give the disulfide called MBTS. Upon oxidation in the presence of secondary amines, it gives sulfenamide derivatives. One commercially useful example is 2-morpholinodithiobenzothiazole (MBSS), which is used as an accelerator in the vulcanization of rubber.

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 at Goodyear Tire & Rubber.

This compound is used as cooling tower biocide.

The compound has also been used in the past in the gold-mining industry to "float" the gold from ore residue as part of the extraction process.

Safety

Studies have identified it as a potiential human carcinogen. In 2016, it was identified by the World Health Organization as a human carcinogen.

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.

References

Mercaptobenzothiazole Wikipedia