The Chemistry of Vinylsulfonic Acid

Vinylsulfonic acid and its derivatives can be prepared from β‐chloroethanesulfonyl chloride or carbyl sulfate (β‐hydroxysulfonyloxyethanesulfonic anhydride). The chemistry of vinylsulfonic acid has assumed industrial importance since the discovery of a simple synthesis of β‐chloroethanesulfonyl chloride from chloroethane or ethane, sulfur dioxide, and chlorine by the Reed process. Carbyl sulfate is as important a starting material as β‐chloroethanesulfonyl chloride, and surpasses the latter in some respects, e.g. on account of the low price of its components ethylene and sulfur trioxide. Vinylsulfonates undergo addition reactions with alcohols, phenols, thiols, sulfinic acids, carboxylic acids, amides, imides, and hydrazides, as well as with amines, ureas, diazonium salts, and nitroparaffins. Furthermore, they undergo halogenation, nitration, olefination, and the Diels‐Adler reaction. – Methods for the preparation of the free vinylsulfonic acid are described. Alkyl vinylsulfonates are excellent alkylating agents. The derivatives of vinylsulfonic acid are used e.g. as plasticizers, emulsifiers, and fungicides.