Sulfur Mustard - Synthesis

Synthesis

Sulfur mustard is the organic compound with formula (Cl-CH2CH2)2S. In the Depretz method, sulfur mustard is synthesized by treating sulfur dichloride with ethylene:

SCl2 + 2 C2H4 → (Cl-CH2CH2)2S

In the Levinstein process, sulfur monochloride is used instead:

8 S2Cl2 + 16 C2H4 → 8 (Cl-CH2CH2)2S + S8

In the Meyer method, thiodiglycol is produced from chloroethanol and potassium sulfide and chlorinated with phosphorus trichloride:

3 (HO-CH2CH2)2S + 2 PCl3 → 3 (Cl-CH2CH2)2S + 2 P(OH)3

In the Meyer-Clarke method, concentrated hydrochloric acid (HCl) instead of PCl3 is used as the chlorinating agent:

(HO-CH2CH2)2S + 2 HCl → (Cl-CH2CH2)2S + 2 H2O

Thionyl chloride and phosgene have also been used as chlorinating agents.

It is a viscous liquid at normal temperatures. The pure compound has a melting point of 14 °C (57 °F) and decomposes before boiling at 218 °C (424.4 °F).

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