Patent GB-928548-A (GB)
Title: Process for the production of alkyl sulphonates and alkyl sulphonic acid esters from mineral oil fractions
IPC: C07C309/65
Filed: 1961-08-02
Abstract: Mineral oil fractions boiling within the range of 180 DEG  to 350 DEG C. (e.g. diesel oil fractions) are hydrogenated and then refined with concentrated sulphuric acid, fuming sulphuric acid, aluminium chloride, sulphur trioxide or sulphur trioxidecontaining gases (e.g. contact oven gases obtained in the production of sulphuric acid), preferably at a temperature between 0 DEG  and 120 DEG C.  The refining is optionally carried out in the presence of chlorine and/or hydrogen chloride, preferably in an amount of 50-200 volume per cent of the volume of oil used.  Small amounts of dissolved resins or acids remaining in the refined hydrogenated oil may be removed with adsorption agents such as fuller's earth and/or water.  The refined oil is then sulphochlorinated (see Group IV(b)).  Specification 878,845 is referred to.ALSO:Alkyl sulphonates and alkyl sulphonic acid esters of high stability and only slight colour are obtained from mineral oil fractions (b.p. 180-350 DEG .C.) by hydrogenating the mineral oil fractions, refining the product with concentrated sulphuric acid, fuming sulphuric acid, aluminium chloride, sulphur trioxide or sulphur trioxide-containing gases, possibly in the presence of chlorine and/or hydrogen chloride, sulphochlorinating the hydrocarbon mixture, so obtained, by the action of chlorine and sulphur dioxide in the presence of light to a maximum content of alkyl sulphochlorides of about 50%, refining the sulphochlorination product with concentrated sulphuric acid, fuming sulphuric acid, aluminium chloride, sulphur trioxide or sulphur trioxide-containing gases, and converting the refined product by hydrolysis or alcoholysis into the corresponding alkyl sulphonates or alkyl sulphonic acid esters.  The treatment of the hydrogenated mineral oil with the specified reagents is preferably carried out with intensive mixing between 0 DEG  and 120 DEG C.  If 98% sulphuric acid is used, the amount required is generally 10-30% by weight of the mineral oil; for fuming sulphuric acid less than 10% is sufficient.  As sulphur trioxide-containing gases, there may be used contact oven gases obtained in the production of sulphuric acid.  The refining treatment of the alkyl sulphochlorides can generally be carried out at room temperature or slightly elevated temperatures.  Generally 5-30% or refining agent, based on the weight of sulphochlorides, is sufficient.  The sulphochlorides can be freed from residual refining agents and resinous products by centrifuging or by treatment with adsorption agents, e.g. fuller's earth and/or water.  In the examples, diesel oil fractions, hydrogenated over a cobalt catalyst, are (1) treated with 100% sulphuric acid, sulphochlorinated (using irradiation from a tungsten lamp), and then treated twice with 98% sulphuric acid; (2) treated with contact oven gas (6.5% SO3), sulphochlorinated, and then treated three times with 98% sulphuric acid; (3) treated with aluminium chloride, sulphochlorinated, and treated twice with 98% sulphuric acid.  In Example (4) the non-sulphochlorinated oil from Example (1) was treated with aluminium chloride tar obtained from Example (3), and then sulphochlorinated and refined as in Example (1).  In all the examples, the sulphochlorides were converted partly to the corresponding sodium alkyl sulphonates, and partly to the phenyl and cresyl esters of the corresponding alkyl sulphonic acids. Specification 878,845 is referred to.