Patent GB-454183-A (GB)
Title: A process of producing nucleus-substituted aliphatic-aromatic sulphonic acids
IPC: C07B45/02
Filed: 1935-07-09
Abstract: Water-soluble products are obtained by the joint condensation and sulphonation of a polynuclear hydrocarbon or a substitution product thereof, a fatty acid having ten or more carbon atoms or a derivative thereof, and an alcohol corresponding to the acid of a natural fat, or a sulphuric ester of such an alcohol.  Specified polynuclear hydrocarbons and substitution products are naphthalene, tetrahydronaphthalene, octahydroanthracene, and their alkyl, halogen, hydroxy and amino derivatives.  Specified fatty acids are dodecylic, tetradecylic, hexadecylic, octadecylic and octadecenylic acids and mixtures thereof; the anhydrides or chlorides of such acids, or their esters with monohydric or polyhydric alcohols, may also be used, castor oil and olive oil being specified.  Specified alcohols corresponding to the acids of natural fats are dodecyl, hexadecyl and octadecenyl alcohols.  The reaction mixture may include also an alcohol having six or less carbon atoms, an aralkyl alcohol or halide, a phenol, or cyclohexanol.  Sulphonation may precede or follow condensation or be concurrent therewith.  Both the condensation and the sulphonation may be effected with sulphuric acid, oleum or chlorsulphonic acid.  The acids obtained may be converted into their alkali or ammonium salts or into salts with organic bases, e.g. ethanolamine, triethanolamine, or pyridine.  The products are useful (a) as wetting and cleansing agents in the textile and allied industries, e.g. in the manufacture of leather, (b) as emulsifiers for oils, fats and waxes, and (c) as fat-splitting catalysts.  In the examples: (1) a melt of cetyl alcohol and naphthalene is treated with oleum, and castor oil and additional oleum are then added; the neutralized product is useful as a fat-splitting agent; (2) cetyl sulphuric ester and naphthalene are treated with oleum, and castor oil and chlorsulphonic acid are added; the product is neutralized partly with soda lye and partly with pyridine to yield an assistant for through-dyeing processes; (3) a mixture of naphthalene, olive oil, benzyl chloride and octadecenol is treated in turn with oleum and chlorsulphonic acid; (4) a mixture of naphthalene and castor oil is treated with oleum, and the product is treated with alcohols obtained by reducing coconut oil fatty acids, butyl alcohol, and chlorsulphonic acid; (5) a mixture of tetrahydronaphthalene, castor oil and cetyl alcohol is treated with oleum; the neutralized product is useful as a witting agent. Specifications 364,107 and 374,866 are referred to.  Samples have been filed, under Sect. 2 (5), of products prepared as follows: (1) a mixture of b -naphthol and cetyl alcohol is treated with oleum, and castor oil and additional oleum are then added and the product is neutralized; (2) b -naphthylamine is heated with sulphuric acid and then treated with olein alcohol and oleum; castor oil and chlorsulphonic acid are then added, and the product is neutralized and boiled with alcohol to remove residual salts.  The Specification as open to inspection under Sect. 91 defines the alcohols to be used in the process as aliphatic alcohols having more than six carbon atoms.  This definition does not appear in the Specification as accepted.ALSO:Water-soluble products are obtained by the joint condensation and sulphonation of a polynuclear hydrocarbon or a substitution product thereof, a fatty acid having ten or more carbon atoms or a derivative thereof, and an alcohol corresponding to the acid of a natural fat, or a sulphuric ester of such an alcohol. Specified polynuclear hydrocarbons and substitution products are naphthalene, tetrahydronaphthalene, octahydroanthracene, and their alkyl, halogen, hydroxy and amino derivatives.  Specified fatty acids are dodecylic, tetradecylic, hexadecylic, octadecylic and octadecenylic acids and mixtures thereof; the anhydrides or chlorides of such acids, or their esters with monohydric or polyhydric alcohols, may also be used, castor oil and olive oil being specified. Specified alcohols corresponding to the acids of natural fats are dodecyl, hexadecyl and octadecenyl alcohols.  The reaction mixture may include also an alcohol having six or less carbon atoms, an aralkyl alcohol or halide, a phenol, or cyclohexanol.  The acids obtained may be converted into their alkali or ammonium salts or into salts with organic bases, e.g. ethanolamine, triethanolamine, or pyridine.  The products are useful as emulsifiers for oils, fats and waxes and as fat-splitting catalysts.  In the examples: (1) a melt of cetyl alcohol and naphthalene is treated with oleum, and castor oil and additional oleum are then added; the neutralized product is useful as a fat-splitting agent; (2) cetyl sulphuric ester and naphthalene are treated with oleum, and castor oil and chlorsulphonic acid are added; the product is neutralized partly with soda lye and partly with pyridine; (3) a mixture of naphthalene, olive oil, benzyl chloride and octadecenol is treated in turn with oleum and chlorsulphonic acid; (4) a mixture of naphthalene and castor oil is treated with oleum, and the product is treated with alcohols obtained by reducing coconut oil fatty acids, butyl alcohol, and chlorsulphonic acid; (5) a mixture of tetrahydronaphthalene, castor oil and cetyl alcohol is treated with oleum.  Specifications 364,107 and 374,866 are referred to.  Samples have been filed, under Sect. 2 (5) of products prepared as follows: (1) a mixture of b -naphthol and cetyl alcohol is treated with oleum, and castor oil and additional oleum are then added and the product is neutralized; (2) b -naphthylamine is heated with sulphuric acid and then treated with olein alcohol and oleum; castor oil and chlorsulphonic acid are then added, and the product is neutralized and boiled with alcohol to remove residual salts.  The Specification as open to inspection under Sect. 91 defines the alcohols to be used in the process as aliphatic alcohols having more than six carbon atoms.  This definition does not appear in the Specification as accepted.