Levinstein process

What is Levinstein process?

The Levinstein process is a chemical method used to produce bis(2-chloroethyl)sulfide, commonly known as mustard gas or sulfur mustard. The process involves bubbling dry ethylene gas through sulfur monochloride at a temperature of 35 °C, followed by the distillation of the remaining material.

Research has revealed that ethylene does not readily react with pure sulfenyl chloride S2Cl2. However, when the reaction is carried out in carbon tetrachloride CCl4, it proceeds at an extremely fast rate, possibly due to the low solubility of ethylene in sulfenyl chloride. The yield of mustard gas, also known as bis(2-chloroethyl)sulfide, is strongly influenced by the reaction temperature.

Levinstein process - mustard gas - sulfur mustard synthesis - general reaction scheme - bis(2-chloroethyl)sulfide
Levinstein process

There are alternative methods for synthesizing mustard gas, one of which involves the chlorination of thiodiglycol. The date and references for the first synthesis of sulfur mustard are uncertain. However, in the early 19th century, the Belgian-French chemist César-Mansuète Despretz reported on the formation of a chemical compound resulting from the reaction between sulfur dichloride S2Cl2 and ethylene.

As the Levinstein process has been employed in the production of mustard gas for military purposes, and since it is mainly intended for the industrial production of this substance, no details of laboratory preparation is given here.

References

Fuson, R. C., Price, C. C., Bauman, R. A., Bullitt, O. H. Jr., Hatchard, W. R., and Maynert, E. W. (1946). Levinstein Mustard Gas. I. 2-Haloalkylsulfenyl Halides. The Journal of Organic Chemistry, 11(5), 469-474. https://doi.org/10.1021/jo01175a007

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