mustard gas(redirected from 1 5-Dichloro-3-Thiapentane)
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Yperite (β, β′-dichlorodiethyl sulfide), a thio ether of the aliphatic series, S(CH2CH2C1)2; it is poisonous. Mustard gas was first used on July 12, 1917, by the Germans against Anglo-French troops near the Belgian town of Ypres (hence the name yperite).
Mustard gas is a colorless liquid. Melting point, 14.5°C; boiling point, 217°C (with partial decomposition); density, 1.280 g/cm3 (15°C); solubility in water, 0.05 percent. It is readily soluble in organic solvents. Industrial-grade mustard gas is a dark brown, almost black liquid with an unpleasant odor. Mustard gas is hydrolyzed very slowly by water; the rate of hydrolysis increases sharply in the presence of caustic alkalies or upon heating and mixing. It reacts vigorously with chlorinating and oxidizing agents. Since nontoxic products are formed in this case, the above reactions are used for decontamination. Mustard gas forms colored complexes with salts of heavy metals. This property is used for the detection of mustard gas.
Mustard gas is prepared by two methods: (1) from ethylene, CH2=CH2, and sulfur chlorides, such as S2C12 or SCl2; (2) from thiodiglycol, S(CH2CH2OH)2, and hydrochloric acid, HC1. It is a protoplasmic poison. It attacks the skin and eyes in the form of liquid drops, vapor, and mist. Inhalation of the vapor causes grave harm to the upper respiratory tract and the lungs. A characteristic property of mustard gas is the “latent period” (up to 12 hours or more).
Analogous physiological effects are produced by a group of materials of the type RN(CH2CH2C1)2, where R = CH3,C2H5, or CH2CH2C1, which are arbitrarily called nitrogen mustards. The nitrogen mustards are colorless, odorless high-boiling liquids. They are slowly hydrolyzed by water. The hydrolysis is accelerated in the presence of alkalies. The reaction of nitrogen mustards with chlorinating and oxidizing agents generates nontoxic products. These reactions are also used for decontamination. Nitrogen mustards are produced from tertiary β-hydroxyethylamines, RN(CH2CH2OH)2, where R = CH3,C2H5, or CH2CH2OH, by replacing the hydroxyl groups with chlorine atoms. A characteristic feature of nitrogen mustards is their inhibiting action on cell division, in connection with which some nitrogen mustards, as well as their derivatives (such as Embichin and Endoxan), have come to be used in the treatment of malignant tumors.
Gas masks and special protective clothing are used for the protection of the respiratory organs and the skin, respectively.
REFERENCESSoborovskii, L. Z., and G. Iu. Epshtein. Khimiia i tekhnologiia boevykh otravliaiushchikh veshchestv. Moscow, 1938.
Sartori, M. “Novoe v khimii boevykh otravliaiushchikh veshchestv.” Uspekhi khimii, 1954, vol. 21, part 1, p. 62.
R. N. STERLIN