THE SULFONIUM SALT OF MUSTARD GAS: BIS-ß-[BIS(ß-HYDROXYETHYL) SULFONIUM] ETHYLSULFIDE DICHLORIDE (H·2TDG)

Abstract

1. The sulfonium salt H·2TDG is formed when H is mixed with even dilute solutions of TDG. Crystalline H·2TDG was isolated from such a reaction mixture. A simple method of preparation of this salt is outlined. 2. A material which differs from H·2TDG in that it hydrolyzes faster, is formed when H hydrolyzes in water. This material is probably H·1TDG but it was not isolated. Approximately 5 to 8 per cent of the original H is converted to this sulfonium salt. 3. The hydrolysis constant of M/100 H·2TDG has been determined at 20°, 25.5°, 37°, 75°, and 100°C., a temperature coefficient, Q10, of 3–4 was obtained. The effect of temperature is in agreement with that predicted by the Arrhenius equation. An activation energy of 26,000 calories was calculated.