GB869921A - Making chloro-substituted organic sulphonyl fluorides - Google Patents

Abstract

In a process for making chloro-substituted organic sulphonyl fluorides sulphuryl chlorofluoride is reacted in the presence of a free radical initiator with an olefinic compound copolymerisable with sulphur dioxide. The products of the process include compounds having the general formula: <FORM:0869921/IV (b)/1> in which R, R1 and R11 represent hydrogen or alkyl radicals and n is an integer from 1-15. Free radical-initiators specified include actinic radiation such as untraviolet light, an organic peroxide, e.g. di-tertiary butyl and benzoyl peroxide, or hydroperoxide or an aliphatic azo compound. Among the many olefinic starting materials specified are included ethylene, propylene, butene, vinyl chloride and bromide, alkyl chloride, cyclohexene, cyclopentene, 1,3-dienes, undecylenic acid and the methyl ester thereof, undecylenic alcohol, allyl acetic acid, N-allyl acetamide, methyl allyl ether, ethyl allyl ether, phenyl allyl ether, diallyl ether, styrene, ortho-allyl anisole, orotho-allyl phenol and para-bromo-allyl benzene. In examples the following olefines are reacted with sulphonyl chlorofluoride: Ethylene, propylene, isobutylene, butene-1, octene-1, octadecene-1, undecenyl and allyl chlorides, diallyl ether. With the latter starting material a substituted tetrahydropyran is obtained. The products of the examples may be converted to the corresponding sulphonic acids, metal and ammonium salts, acid chlorides and sulphonamides. The corresponding sulphonic acids may be obtained by hydrolysis of the sulphonyl fluoride in hot alkali solution and decomposing the salt formed with strong sulphuric acid solution. The metal and ammonium salts may be obtained by reacting the sulphonic acids with the metal or metal oxide and ammonium hydroxide. The sulphonyl chlorides may be obtained by reacting the sulphonic acids with PCl5 or the salts with the PCl,2ZnCl2 complex. The sulphonamides can be prepared by reacting the sulphonyl fluoridesor chlorides with liquid ammonia. The chloro-alkane sulphonyl fluorides may be employed in the preparation of surface active agents, water repellant impregnants and coatings and epoxy resin curing agents. Specifications 758,467 and 869,922 are referred to.