GB516214A - Improvements in the manufacture and production of organic halogen-sulphonic acid chlorides - Google Patents

Abstract

516,214. Halogen sulphochlorides. JOHNSON, G. W. (I.G. Farbenindustrie Akt.-Ges.). July 28, 1938, No. 22501. [Class 2 (iii)] Halogenated sulphonic acid chlorides, which may contain more than one sulphochloride group, are prepared by acting with a mixture of sulphur dioxide and chlorine during irradiation with short-wave light, preferably shorter than 2,200 Angstrom units, in the liquid phase on halogen hydrocarbons containing in the molecule at least one carbon atom to which is attached at least one hydrogen atom but no halogen atom, preferably at temperatures below 50‹C., e.g., 0‹-20‹C. Initial materials specified are 1- or 2-monochlorpropane, 1- or 2-mono-chlor-normal-butane and its isomers such as monochlor-isobutanes, 1.2-dichlornormal-butane, dichlordodecane, monobromoctadecane and cyclic halogen hydrocarbons such as cyclohexylchloride; the halogenated hydrocarbons may also contain non-halogenated hydrocarbons and mixtures of different halogeen hydrocarbons may be used, e.g., halogenated hydrocarbons formed by the action of halogen on the hydrocarbons obtained by the catalytic hydrogenation of carbon monoxide at ordinary or moderately increased pressure. The reaction may be carried out under pressure, and, especially in the case of solid or very low boiling halogen hydrocarbons, in the presence of solvents such as halogen hydrocarbons containing one or more halogen atoms on every carbon atom, e.g., carbon tetrachloride or ethylene chloride. The mixture of chlorine and sulphur dioxide which may contain equal volumes of each or which may have an excess of sulphur dioxide, may be lead through dispersing means provided at the bottom of a vessel, e.g., of enamelled iron or ceramic material, in which the initial material is situated, while irradiating with short wave light, e.g, by using a mercury vapour lamp, or by passing the light through a window of quartz or of a glass permeable to ultra-violet light. In examples, (1) chlorbutane sulphonic acid chloride, along with some 1.2- and 1.3-dichlorbutane, is obtained by passing chlorine and sulphur dioxide into 1-chlor-normal-butane for 7 hours, (2) cyclohexane sulphonic acid chloride is obtained from cyclohexyl chloride by the method of example (1), (3) chlorinated hydrocarbons having an average chlorine content of 9.1 per cent. obtained by chlorinating a hydrocarbon mixture having a boiling range of 200‹-350‹C. is reacted in the manner described in example 1 ; 1:2 dichlor-normal-dodecane and' a chlorinated hydrocarbon prepared from a hydrocarbon oil having a boiling range of 200‹-350‹C., are similarly treated.