MANUFACTURE OF 4-CHLOROPHENYLSULFONYL COMPOUND

Japanese Patent JPS59141556

A

1. A process for the preparation of 4-chlorophenylsulfonyl compounds of the general formula (1) see diagramm : EP0115328,P7,F2 wherein R represents a hydrogen or chlorine atom or an alkyl, oxalkyl or alkoxy group, a hydrazino group, a primary amino, a primary or secondary alkylamino, an aralkylamino or a phenylamino group, the phenyl group being optionally substituted by chlorine or bromine atoms, alkyl, alkoxy or phenoxy groups, or R represents a 4-chlorophenyl group, by reacting chlorobenzene with chlorosulfonic acid and thionyl chloride to give 4-chlorobenzenesulfochloride followed by a reaction of the latter with ammonia, hydrazine, primary or secondary aliphatic amine, aromatic amine, alkali metal sulfite or alkanol to give compounds of said formula (1), which comprises slowly reacting 1 mol of chlorobenzene with a mixture of 1.0 mol to 1.05 mol of chlorosulfonic acid and 1.0 mol to 1.25 mol of thionyl chloride at a temperature of about 20 to 90 degrees C, provided that the reaction mixture always remains liquid, optionally in the presence of a catalyst commonly used for the formation of sulfonic acid chloride by means of thionyl chloride, and subsequently reacting 4-chloro-benzene-sulfochloride thus obtained as a melt, preferably directly or after its separation from 4,4'-dichlorodiphenylsulfone obtained as a by-product, a) with an aqueous solution, suspension or emulsion of ammonia, hydrazine, a primary or secondary aliphatic amine or an aromatic amine of the benzene series, at a temperature of about 0 to about 100 degrees C to give the corresponding 4-chlorobenzenesulfonamides, or b) with an aqueous alkali metal sulfite solution, at a temperature of about 20 to about 90 degrees C at a pH-value of 6 to 9 to give the corresponding 4-chlorobenzenesulfinates followed by neutralization of the aqueous solution by an acid to give the free 4-chlorobenzenesulfinic acid or by a reaction with alkylation agents to give the corresponding 4-chlorophenylalkylsulfones, or c) with the at least stoichiometric quantity of an alkanol, at a temperature of about 20 to about 90 degrees C to give the corresponding 4-chlorobenzenesulfonic acid alkyl ester, or d) with the at least stoichiometric quantity of chlorobenzene in the presence of catalytic amounts of iron(III)-chloride at temperatures of from 120 to 160 degrees C to give 4,4'-dichlorodiphenylsulfone.

TEODOORU PAAPENFUUSU

JP1112084A

August 14, 1984

January 26, 1984

Click for automatic bibliography generation  

HOECHST AG

C07B61/00; B01J31/00; B01J31/02; C07C67/00; C07C301/00; C07C303/08; C07C303/12; C07C303/28; C07C303/38; C07C309/73; C07C309/78; C07C309/86; C07C311/15; C07C311/16; C07C311/21; C07C311/49; C07C313/00; C07C315/00; C07C317/14; (IPC1-7): B01J31/02; C07C139/00; C07C143/68; C07C143/78; C07C143/825; C07C147/06

JPS5321143A	1978-02-27
JP42017732A
JPS57116044A	1982-07-19

Ezaki Mitsuyoshi

Previous Patent: MANUFACTURE OF ANHYDROUS ALKANE SULFONIC ACID

Next Patent: FUNGICIDAL ORGANIC PHOSPHORUS DERIVATIVE SALT