Patent GB-452584-A (GB)
Title: Improvements in or relating to the manufacture of aminosulphonic acids
Filed: 1935-02-25
Abstract: Aminosulphonic acids are obtained by condensing carbonylsulphonic acids (or their salts) with ammonia or primary amines, and reducing the condensation products; the condensation and the reduction may be effected simultaneously or successively. Specified carbonylsulphonic acids are acetaldehydesulphonic acid, propionaldehydesulphonic acid, butyraldehydesulphonic acid, benzaldehydesulphonic acids, acetonesulphonic acid, 2-butanone-1-sulphonic acid (from chloromethylethyl ketone and sodium sulphite), 2-butanone-3-sulphonic acid (from a -chlorethylmethyl ketone and sodium sulphite), 3-pentanone-2-sulphonic acid (from ethyl-a -chlorethyl ketone and sodium sulphite), camphorsulphonic acid, cyclohexanonesulphonic acid (from o-chlorocyclohexanone and sodium sulphite), N-methyl-N-oxopropyltaurine (from monochloracetone and methyltaurine), oxopropyl sulphoethyl sulphide (CH3COCH2SCH2 CH2SO3H) (from chlorethanesulphonic acid and acetone mercaptan), and a product of the formula COOHCH2NCH3CH2COCH2NCH3CH2 CH2SO3H (prepared by treating sym. dichloracetone with a mixture of sarcosine and methyltaurine).  Specified primary amines are methylamine, ethylamine, butylamine, aniline, cyclohexylamine, benzylamine, ethylenediamine, 2 : 2<1>-diaminodiethyl ether, polyalkylene polyamines, dodecylamine, octadecylamine, octadecyleneamine, technical mixtures of higher amines, and amines corresponding to resin or naphthenic acids.  The condensation may be effected at a raised temperature in an aqueous or aqueous-organic medium, and the reduction may be effected with sodium amalgam, or with hydrogen in the presence of a copper or nickel catalyst and at a raised temperature and pressure.  The products obtained from amines containing eight or more carbon atoms may be used in processes for treating textiles, leather and like materials, e.g. in washing, wetting, bucking, bleaching, drumming, dyeing with vat, sulphur or azo dyes, after-treating or stripping dyeings, sizing, impregnating, dressing and finishing; they may also be used for preparing emulsions of fats, oils, fatty acids and waxes, including paraffin wax.  The products obtained from ammonia or amines containing less than eight carbon atoms are useful as intermediates; thus, they may be condensed with higher organic acids, e.g. higher fatty acids, to yield products useful for the purposes specified above.  The products may be used alone or mixed with one another or with other assistants in the textile and leather industries, e.g. soaps, turkey-red oils, alkylnaphthalenesulphonic acid, condensation products of higher carboxylic acids with hydroxyalkylsulphonic acids, sulphonates of fatty alcohols, glue, proteins or their degradation products, starch, soluble gums, vegetable mucilages, alcohols, ketones, hydrocarbons, and halogenated hydrocarbons.  In the examples: (1) sodium acetonesulphonate and aqueous ammonia are heated in hydrogen in the presence of a nickel-copper catalyst; sodium b -aminopropanesulphonate is obtained, and may be condensed with oleic acid chloride or the chlorides of coconut fatty acids; (2) sodium acetone sulphonate and methylamine in methyl alcohol are heated in hydrogen in the presence of nickel carbonate precipitated on fuller's earth; sodium b  - methylaminopropanesulphonate is obtained, and may be used for stabilizing diazo compounds; (3) sodium acetonesulphonate and dodecylamine are heated in ethyl alcohol, and the product is hydrogenated in methyl alcohol in the presence of a nickel-copper catalyst, or reduced with sodium or sodium amalgam; sodium b -dodecylaminopropanesulphonate is obtained; (4) the product of example 3 is obtained directly from sodium acetonesulphonate and dodecylamine as in example 2; (5) sodium acetonesulphonate and octadecylamine, treated as in example 2, yield sodium b  - octadecylaminopropanesulphonate, useful for dispersing calcium soaps and vat dyes; (6) butyraldehyde-3-sulphonic acid and ammonia similarly yield 1 - aminobutane - 3 - sulphonic acid, which may be condensed with oleic acid chloride; (7) benzaldehyde-2-sulphonic acid and n-butylamine, as in example 2, yield N - butylbenzylamine - 2 - sulphonic acid; (8) sodium 2 - butanone - 1 - sulphonate and ammonia similarly yield sodium 2-aminobutane-1-sulphonate, which may be condensed with oleic acid chloride; (9) sodium 2-butanone-3-sulphonate and ammonia similarly yield sodium 2 - aminobutane - 3 - sulphonate; (10) sodium 3 - pentanone - 2 - sulphonate and ammonia similarly yield sodium 3 - aminopentane-2-sulphonate, which may be condensed with oleic acid chloride; (11) camphorsulphonic acid and ammonia, as in example 2, yield bornylaminesulphonic acid; (12) benzaldehyde-2-sulphonic acid and aniline, as in example 2, yield N-(o-sulphobenzyl)aniline; (13) benzaldehyde-2-sulphonic acid and cyclohexylamine similarly yield N-(o-sulphobenzyl)cyclohexylamine; (14) sodium acetonesulphonate and benzylamine similarly yield sodium b -benzylaminopropanesulphonate. The Provisional Specification describes the treatment of the product of example 2 with oleic acid chloride.  It refers also to Specification 341,053.ALSO:Aminosulphonic acids are obtained by condensing carbonylsulphonic acids (or their salts) with ammonia or primary amines, and reducing the condensation products; the condensation and the reduction may be effected simultaneously or successively. Specified carbonylsulphonic acids are acetaldehydesulphonic acid, propionaldehydesulphonic acid, butyraldehydesulphonic acids, benzaldehydesulphonic acids, acetonesulphonic acid, 2-butanone-1-sulphonic acid, 2-butanone-3-sulphonic acid, 3 - pentanone - 2 - sulphonic acid, camphorsulphonic acid, cyclohexanonesulphonic acid, N-methyl-N-oxopropyltaurine, oxopropyl sulphoethyl sulphide (CH3COCH2SCH2CH2SO3H) and a product of the formula COOHCH2NCH3CH2 COCH2NCH3CH2CH2SO3H.  Specified primary amines are methylamine, ethylamine, butylamine, aniline, cyclohexylamine, benzylamine, ethylenediamine, 2 : 2<1>-diaminodiethyl ether, polyalkylenepolyamines, dodecylamine, octadecylamine, octadecyleneamine, technical mixtures of higher amines, and amines corresponding to resin or naphthenic acids.  The products obtained from amines containing eight or more carbon atoms may be used in processes for treating textiles, leather and like materials, e.g. in washing; they may also be used for preparing emulsions of fats, oils, fatty acids and waxes, including paraffin wax.  The products obtained from ammonia or amines containing less than eight carbon atoms are useful as intermediates; thus, they may be condensed with higher organic acids, e.g. higher fatty acids, to yield products useful for the purposes specified above.  The products may be used alone or mixed with one another or with other assistants in the textile and leather industries, e.g. soaps, turkey-red oils, p alkylnaphthalenesulphonic acids, condensation products of higher carboxylic acids with hydroxyalkylsulphonic acids, sulphonates of fatty alcohols, glue, proteins or their degradation products, starch, soluble gums, vegetable mucilages, alcohols, ketones, hydrocarbons, and halogenated hydrocarbons.  In the examples: (1) sodium acetonesulphonate and aqueous ammonia yield sodium b -aminopropanesulphonate, which may be condensed with oleic acid chloride or the chlorides of coconut fatty acids; (2) sodium acetonesulphonate and methylamine yield sodium b -methylaminopropanesulphonate; (3) sodium acetonesulphonate and dodecylamine yield sodium b -dodecylaminopropanesulphonate; (4) sodium acetonesulphonate and octadecylamine yield sodium b -octadecylaminopropanesulphonate, useful for dispersing calcium soaps and vat dyes; (5) butyraldehyde-3-sulphonic acid and ammonia yield 1-aminobutane-3-sulphonic acid, which may be condensed with oleic acid chloride; (6) benzaldehyde-2-sulphonic acid and n-butylamine yield N-butylbenzylamino-2-sulphonic acid; (7) sodium 2-butanone-1-sulphonate and ammonia yield sodium 2-aminobutane-1-sulphonate, which may be condensed with oleic acid chloride; (8) sodium 2-butanone-3-sulphonate and ammonia yield sodium 2-aminobutane-3-sulphonate; (9) sodium 3-pentanone-2-sulphonate and ammonia yield sodium 3-aminopentane-2-sulphonate, which may be condensed with oleic acid chloride; (10) camphorsulphonic acid and ammonia yield bornylaminesulphonic acid; (11) sodium benzaldehyde-2-sulphonate and aniline yield the sodium salt of N-(o-sulphobenzyl)aniline; (12) benzaldehyde-2-sulphonic acid and cyclohexylamine yield N - (o - sulphobenzy)cyclohexylamine; (13) sodium acetonesulphonate and benzylamine yield sodium b -benzylaminopropanesulphonate. The Provisional Specification describes the treatment of the product of example 2 with oleic acid chloride and refers to Specification 341,053.