Patent GB-488490-A (GB)
Title: The manufacture of organic nitrogenous base salts of sulphuric acid esters and products thereof
Filed: 1936-11-05
Abstract: Hydroxyalkylamine salts of compounds in which an aliphatic acyl radical containing at least four carbon atoms in a straight chain is linked to one or more sulphato groups through the residue of an aliphatic polyhydroxy compound of the class consisting of glycols, polyglycols, glycerols, polyglycerols, hydroxycarboxylic acids, sugars, sugar-alcohols and acid derivatives of sugars, are made by reacting a polyhydroxy compound of the class described with an aliphatic carboxylic acid containing at least four carbon atoms in a quantity insufficient to combine with all the hydroxy groups of the polyhydroxy compound, and with a sulphating agent, the resulting product being neutralized with a hydroxyalkylamine.  The fatty acids which may be used include caproic, capric, capryllic, valeric, butyric, melissic, hydroxystearic, palmitic, stearic, lauric, oleic, elaidic, myristic, ricinoleic and linoleic acids, as well as acids derived from animal and vegetable fats and oils, including fish oils, and hydrogenated vegetable oils.  Mixtures of acids, such as the mixture of coconut fatty acids obtained from coconut oil, may be used.  The polyhydroxy compounds include glycols and glycerols and their polymers, mucic, tartaric, saccharic, gluconic, glycuronic, gulonic, mannonic, trihydroxyglutaric and glyceric acids, hydroxy carboxylic oxidation products of polyglycerols, xylose, galactose, fructose, maltose, sucrose, glucose, diethylene glycol, sorbitol, dulcitol and arabitol.  As hydroxyalkylamines, mono-, di- and tri-ethanolamine are specified, and as sulphating agents concentrated or fuming sulphuric acid, chlorsulphonic acid, sulphuryl chloride, and sulphur trioxide, in the presence or absence of solvents such as pyridine.  The products may be used as wetting, emulsifying or anti-spattering agents, e.g. for preventing the spattering of margarine in frying.  Their effect may be enhanced by the addition of other agents, particularly of esters of the polyhydroxy compounds employed, e.g. mono - oleyl diethyleneglycol, mixed mono acid esters of diethylene glycol or glycerol with mixed coconut fatty acids, and monocaprylin.  In examples: (1) monostearin is treated with concentrated sulphuric acid and the product is washed and neutralized with hydroxyalkylamines; monolaurin and other mono fatty acid esters of glycerol may be similarly treated; (2) mono-lauryl diethyleneglycol is treated with chlorsulphonic acid in chloroform and the product neutralized with a hydroxyalkylamine; (3) the mono fatty acid esters of diethylene glycol obtained from mixed coconut oil fatty acids are treated with chlorsulphonic acid in ethylene dichloride and the product neutralized with monoethanolamine; and (4) stearic acid and glycerine are treated with chlorsulphonic acid and the product neutralized with triethanolamine.  Other products referred to are the monoethanolamine salts of myristyl propyleneglycol and dipalmitin sulphuric esters and the triethanolamine salt of mono-oleyl diethyleneglycol sulphuric ester. Specifications 364,107 and 368,812 are referred to.