Perchloromethyl mercaptan

Of the chloro-compounds, perchloromethyl mercaptan and its less chlorinated derivative, thiophosgene, have been used as war gases. Although the latter cannot be considered as a mercaptan, it is described in this chapter because of its close relationship to perchloromethyl mercaptan. 

This substance was employed by the French in September, 1915, but with little success owing to its low offensive powers. 

It was prepared in 1873 by Rathke and later by others, by the action of chlorine on carbon disulphide  

The temperature of the reaction should not be allowed to rise above 50° C., otherwise more highly chlorinated compounds will be formed, especially in the presence of an excess of chlorine. 

Perchloromethyl mercaptan may also be obtained by the action of chlorine on methyl thiocyanate or on thiophosgene.  

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Physical Properties. Trichloromethanesulfenyl chloride [594-42-3] (perchloromethyl mercaptan, a misnomer but used as the common commercial name), CCl SCl, is a strongly acrid, pale yellow Hquid, boiling at 149°C with some decomposition at atmospheric pressure, 68°C at 6.93 kPa (52... 

If bromine is used in equation 8, carbon tetrabromide [558-13-4] is formed. With a minor amount of iodine present, and in the absence of iron catalyst, carbon disulfide and chlorine react to form trichioromethanesulfenyl chloride (perchloromethyl mercaptan [594-42-3]), CCI3SCI, which can be reduced with staimous chloride or tin, and hydrochloric acid to form thiophosgene (thiocarbonyl chloride [463-71-8], CSCI2, an intermediate in the synthesis of many organic compounds (see Sulfurcompounds). 

Perchloromethyl mercaptan Perchloryl fluoride Petroleum distillates (naphtha)... 

Perchlorocyclopentadiene Perchloromethyl Chloroformate Perchloromethyl Mercaptan Perdesiekte... 

The 2003 ACGIH threshold limit value-time-weighted average (TLV-TWA) for perchloromethyl mercaptan is 0.1 ppm (0.76 mg/m ). 

Toxicology. Perchloromethyl mercaptan is a severe pulmonary irritant and lacrimating agent fatal exposure has also caused liver and kidney injury. 

Of three chemical workers who were observed after accidental exposures to perchloromethyl mercaptan, two survived episodes of pulmonary edema, and the third died after 36 hours. The fatality resulted from a spill of the liquid on the clothing and floor with exposure to the vapor. At autopsy, there was necrotizing tracheitis, massive hemorrhagic pulmonary edema, marked toxic nephrosis, and vacuolization of centrilobular hepatic cells. 

Althoff H Tbdliche Perchlormethylmercap-tan-intoxikation (fatal perchloromethyl mercaptan intoxication). Arch Toxikol 31 121-135, 1973... 

ACGIH Perchloromethyl mercaptan. Documentation of the TLVs and BEls, 6th ed, pp 1195-1196. Cincinnati, OH, American Conference of Governmental Industrial... 

Knapp HF, MacAskill SM, Axicker GM, et al Effects in rats of repeated inhalation exposure to perchloromethyl mercaptan. Toxicologist 7 191 (Abst 762) 1987... 

Compound Name Hexachlorocyclopentadiene Tetrachloroethylene Carbon Tetrachloride Perchloromethyl Mercaptan T etrachloroethylene Urea Peroxide Decahydronaphthalene Tetrachloroethylene Hydrogen Peroxide Peracetic Acid... 

Perchloromethyl mercaptan 5-(l-Ethylpentyl)hydantoin sodium salt... 

Thus the conception of this discovery the gestation in the early period was difficult and troubled. In the beginning of this century, perchloromethyl mercaptan was considered (and had been given a brief trial as) a war gas. There was little experience with its use by industry. The cost projections and the... 

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