Patent GB-479835-A (GB)
Title: Manufacture of isocyclic compounds
IPC: C07C29/149
Filed: 1936-06-05
Abstract: Products stated to have wetting, foaming, dispersing, and cleansing properties are prepared by treating with polybasic mineral acids or their halides or anhydrides or with amidosulphonic acid, compounds having the formula R.X.Y in which R is a mononuclear or polynuclear aromatic or mononuclear hydroaromatic residue containing a nuclear aliphatic hydrocarbon residue with at least three carbon atoms, X is an alkyl residue united directly or by means of nitrogen or sulphur with R, in the chain of which there may be one or more oxygen atoms and Y is a hydroxy or mercapto group in end position or approximately end position of X.  The products may be used in conjunction with compounds having a cleansing effect, e.g. phosphoric acid salts and bleaching agents; with sodium chloride or sulphate permanent pulverulent products may be produced.  The following starting materials are mentioned: octylphenyloxyethylsulphide (prepared from ethylene oxide and octylthiophenol), hexylnaphthyl - 2 : 3 - dioxypropylsulphide, prepared from a -chlorhydrin and hexylthionaphthol), butyl - o - cresyldiglycolsulphide (prepared from ethyleneoxide and butyl-o-thiocresol), amyl phenyltriglycolsulphone (prepared by oxidation of the corresponding sulphide), dodecyldioxyethyl aniline, butylpolyoxyethyl-o-toluidine, butylphenylethylalcohol, butylcyclohexylbutylalcohol, hexylcyclohexylbutyl-alcohol and oxyalkylation and polyoxyalkylation products of the foregoing compounds.  Products obtained by treating alkylated aromatic amino compounds with ethylene sulphide may also be used.  In examples: (1) tributylphenylethylalcohol, prepared by reduction of tributylphenylacetic acid, is sulphonated in carbon tetrachloride; (2) hexyloxyethylaniline, prepared from hexylaniline and ethylenechlorhydrin, is sulphonated; (3) butylphenylhydroxypropylthioether, prepared from propylenechlorhydrin and the parent thiophenol is sulphonated in ether with chlorsulphonic acid or oleum; (4) octylphenylpentaglycolthioether, prepared from ethyleneoxide and the parent thiophenol is sulphonated; (5) 1 : 2-dibutyl-4-aminobenzene is condensed with propyleneoxide in the presence of sodium methylate and the product sulphonated; (6) decylnaphthyldibutanolamine, prepared by condensing a chlorinated petroleum with naphthalene, nitrating and reducing the condensation product and treating with 1 : 2-butyleneoxide is sulphonated; (7) octylphenylpolyglycolthioether, containing a chain of 20 ethylene oxide molecules is sulphonated; (8) butylnaphthylpolyglycolthioether, containing a chain of 40 ethyleneoxide molecules is treated with phosphoruspentoxide in ethylenechloride; (9) hexylphenyl ethyltriglycolether is sulphonated; (10) dodecylcyclohexyl butylalcohol (prepared by condensing lauric acid with benzene, reducing, further condensing with succinic anhydride, reducing the keto group while simultaneously hydrogenating the benzene ring, and reducing the carboxylic to the alcohol group, is sulphonated. Specification 475,867 is referred to.  A sample has been furnished under Sect. 2 (5) of a product obtained by reacting amidosulphonic acid with n-butylphenylbutanol.  The latter may be made by preparing butylbenzene by reducing the condensation product from benzene and butyric acid chloride, condensing it with succinic anhydride and reducing the product first to butylphenylbutyric acid and then to the alcohol.ALSO:Products stated to have dispersing properties are prepared by treating with polybasic mineral acids or their halides or anhydrides or with amidosulphonic acid, compounds having the formula R.X.Y. in which R is a mononuclear or polynuclear aromatic or mononuclear hydroaromatic residue containing a nuclear aliphatic hydrocarbon residue with at least three carbon atoms, X is an alkyl residue united directly or by means of nitrogen or sulphur with R, in the chain of which there may be one or more oxygen atoms and Y is a hydroxy or mercapto group in end position or approximately end position of X.  The products may be used in conjunction with compounds having a cleansing effect, e.g. phosphoric acid salts and bleaching agents.  The following starting materials are mentioned; octylphenyloxyethylsulphide; hexylnaphthyl - 2 : 3 - dioxypropylsulphide, butyl - o - cresyldiglycolsulphide, amyl phenyltriglycolsulphone, dodecyldioxyethyl aniline, butylpolyoxyethyl - o - toluidine, butylpyenylethylalcohol, butylcyclohexylbutylalcohol, hexylcyclohexylbutylalcohol and oxyalkylation and polyoxyalkylation products of the foregoing compounds.  In examples: (1) tributylphenylethylalcohol is sulphonated in carbon tetrachloride: (2) hexyloxyethylaniline is sulphonated; (3) butylphenylhydroxypropylthioether, is sulphonated, in ether with chlorsulphuric acid or oleum; (4) oxtylphenylpentaglycolthioether, is sulphonated; (5) 1 : 2-dibutyl-4-aminobenzene is condensed with propyleneoxide in the presence of sodium methylate and the product sulphonated; (6) decylnaphthyldibutanolamine, prepared by condensing a chlorinated petroleum with naphthalene, nitrating and reducing the condensation product and treating with 1 : 2-butyleneoxide is sulphonated; (7) octylphenylpolyglycolthioether, containing a chain of 20 ethylene oxide molecules is sulphonated; (8) butylnaphthylpolyglycolthioether, containing a chain of 40 ethyleneoxide molecules is treated with phosphoruspentoxide in ethylenechloride; (9) hexylphenylethyltriglycolether and dodecylcyclohexylbutylalcohol are sulphonated.