Patent GB-687949-A (GB)
Title: Improvements in and relating to fatty ester-amide sulfonates
IPC: C11D1/22
Filed: 1950-04-20
Abstract: The invention comprises the acid, and/or water-soluble salts of the acid, sulphonation products of compounds having the general formula <FORM:0687949/IV (b)/1> wherein R.CO represents acyl groups of saturated fatty acids having about 8 to about 22 carbon atoms or mixed fatty acids having about 8 to about 22 carbon atoms such that the iodine value of the equivalent fats is not above 20, n is an integer not greater than 5, X is hydrogen or an alkyl radical of not more than 4 carbon atoms and Y is an aryl, aralkyl or alkaryl radical of not more than 10 carbon atoms, the sulphonation taking place in the aryl portion of the molecule.  The products, which may be used as detergents (see Group III), may be prepared by sulphonating compounds of the above general formula with strong sulphonating agents such as 98-100 per cent sulphuric acid, oleum or sulphur trioxide at temperatures not exceeding about 60 DEG C. and, if desired, in the presence of inert organic diluents such as dioxane, carbon tetrachloride, ethylene dichloride, hexane and methyl or ethyl acetate.  Neutralization of the sulphonic acids is preferably effected at a temperature not above 50 DEG  C. to give a final pH of 5 to 8; suitable neutralizing agents are sodium hydroxide and alkaline sodium salts, other alkali metal bases, amines, ammonium hydroxide and substituted ammonium hydroxides. The ester-amides to be sulphonated may be prepared by esterifying hydroxy-amides of the general formula <FORM:0687949/IV (b)/2> wherein n, X and Y are as defined above, preferably with the chloride of the appropriate fatty acid generally in the presence of an acid-acceptor, e.g. pyridine, trimethylamine or triethylamine and, if desired, in presence of an inert neutral solvent, e.g. benzene, carbon tetrachloride or ethylene dichloride; alternatively, esterification may be effected with the free fatty acid, its anhydride or an ester thereof.  The fatty acids may be derived from animal or vegetable oils, fats and waxes of low iodine value or which have been hydrogenated or catalytically rearranged, or may be those prepared synthetically, e.g. by oxidation of petroleum hydrocarbons or the Fischer-Tropsch synthesis; the preferred acids are lauric and myristic acids or mixtures thereof as occur in vegetable seed oils or fats containing at least 50 per cent of these acids, typical of such oils being coconut oil, tangkallok kernel oil, ucuhuba nut oil, jaboty kernel oil, palm kernel oil and cohune nut oil, among others.  The hydroxy amides are obtained by amidifying amines of the formula <FORM:0687949/IV (b)/3> X and Y being as defined above, by heating the amine preferably with an ester of the appropriate hydroxy acid, e.g. a C1-4 aliphatic monohydric alcohol ester and distilling off the alcohol as it is liberated; alternatively, there may be used the free hydroxy acids, their anhydrides, lactides, lactones or other inner esters, and hydroxy ester acids or alkyl esters thereof, e.g. CH2OHCO.OCH2COOH or its methyl ester.  In examples: (1) methyl hydroxy acetate is reacted with aniline to form N-phenyl hydroxy acetamide which is acylated with lauroyl chloride and the product sulphonated and neutralized with caustic soda; in place of methyl hydroxy acetate, there may be used the free acid, glycollic anhydride, glycollide, the lactide of lactic acid, beta-propiolactone, gammavalerolactone, or the compound CH3CH.OH.COOCH.CH3.COOH (2) N-methyl aniline; and (3) N-ethyl aniline are substituted for the aniline of (1).  Other amines mentioned are N-propyl, N-isopropyl, N-butyl and N-isobutyl anilines, toluidine, N-methyl toluidine, xylidine, mesidine, naphthylamine, benzylamine, alphamethyl benzylamine and N-propyl benzylamine.  Further examples of hydroxy acids are alpha- and beta-hydroxy propionic acids, alpha-, beta- and gamma-hydroxy butyric acids, alpha-hydroxy isobutyric acid, alpha- and beta-hydroxy valeric and isovaleric acids, and alpha-hydroxy caproic and isocaproic acids.ALSO:Surface-active agents having wetting, sudsing and washing power comprise the acid, and/or water-soluble salts of the acid, sulphonation products of compounds having the general formula <FORM:0687949/IV (c)/1> wherein R.CO represents acyl groups of saturated fatty acids having about 8 to about 22 carbon atoms or mixtures of these acids such that the iodine value of the equivalent fats is not above 20, n is an integer not greater than 5, X is hydrogen or an alkyl radical of not more than 4 carbon atoms and Y is an aryl, aralkyl or alkaryl radical of not more than 10 carbon atoms, the sulphonation taking place in the aryl portion of the molecule. Salts of the alkali metals, amines, ammonia and substituted ammonium hydroxides are mentioned.  The acyl groups R.CO are preferably derived from lauric or myristic acid or mixtures thereof as occur in vegetable seed oils or fats containing at least 50 per cent of these acids.  The compositions may also contain soap, other anionic and non-ionic organic detergents, inorganic salts, e.g. sodium sulphate, sodium chloride, sodium bicarbonate, sodium silicate, sodium pyro-, tri-, tetra- or meta-phosphate, fluorescing agents, carboxymethyl-cellulose, starch, urea, high molecular aliphatic alcohols, fatty acid monoglycerides and fatty acid amides. The production of the sulphonic acids and their salts is described (see Group IV (b)). Compositions described in Examples comprise the sodium salt of the sulphonation product of (1) N-phenyl hydroxy acetamide laurate; (2) the N-methyl derivative thereof; or (3) the N-ethyl derivative thereof, and sodium sulphate and disodium hydrogen phosphate.ALSO:Detergent compositions comprise the acid sulphonation products of compounds having the general formula <FORM:0687949/III/1> wherein RCO represents an acyl group of a saturated fatty acid having about 8 to about 22 carbon atoms or a mixture of these acids such that the iodine value of the equivalent fat is not above 20, n is an integer not greater than 5, x is hydrogen or an alkyl radical of not more than 4 carbon atoms and y is an aryl, aralkyl or alkaryl radical of not more than 10 carbon atoms, the sulphonation taking place in the aryl portion of the molecule. Water-soluble salts of the sulphonation products may also be used, e.g. those derived from alkali metal compounds, amines, ammonia or substituted ammonium hydroxides.  The acyl group RCO is preferably derived from lauric or myristic acid or a mixture thereof such as occurs in vegetable seed oils or fats containing at least 50 per cent of these acids.  The compositions may also comprise soap, other anionic organic detergents e.g. alkyl sulphates and sulphonates, non-ionic organic detergents, e.g. alkyl ethers of polythylene glycol or alkyl phenol ethers or thio ethers, inorganic salts such as sodium sulphate, sodium chloride, sodium bicarbonate, sodium silicate or sodium pyro-, tri, tetra- or metaphosphate, fluorescing agents, carboxy methyl-cellulose, urea, starch, high molecular aliphatic alcohols, fatty acid monoglycerides and fatty acid amides.  The compositions may be prepared in bar, flake, granule, powder, paste, liquid or other form.  The production of the sulphonation products is described and numerous starting materials are mentioned (see Group IV(b)). Compositions disclosed in the examples comprise the sodium salt of the sulphonation product of (1) N-phenyl hydroxy acetamide laurate, (2) its N-methyl derivative or (3) its N-ethyl derivative, sodium sulphate and disodium hydrogen ortho phosphate.