Patent GB-453780-A (GB)
Title: Improvements in the manufacture and production of sulphoneethylamines
Filed: 1935-03-18
Abstract: Sulphone-ethylamines are manufactured by reacting acetylene at elevated temperatures with mixtures of sulphinic acids or their salts and compounds containing at least one nitrogen atom to which at least one hydrogen atom is directly attached, preferably in the presence of basic reacting or surface active substances as catalysts.  The sulphinic acids may be mono-basic or polybasic, aliphatic, aromatic, aliphatic-aromatic, cycloaliphatic, or heterocyclic, and may contain further substituents, e.g. halogen atoms, acid radicles, or alkyl, hydroxyalkyl, alkoxy, nitro or substituted amino groups.  As the nitrogen compounds may be employed ammonia, primary and secondary alkylamines and hydroxyalkylamines, e.g. ethylamine, propylamine, butylamine, octodecylamine, octodecenylamine and mono- and di-hydroxyethylamines, primary and secondary aromatic amines, e.g. aniline, phenylenediamine, naphthylamine and aminoanthraquinone, mono- or polyamines of other isocyclic and heterocyclic compounds, aralkylamines, e.g. phenylethylamine, cycloaliphatic amines, e.g. cyclohexylamine, and their mono-N-alkyl, hydroxyalkyl, aryl and aralkyl derivatives, also compounds having at least one NH-group in a ring, e.g. piperidine or carbazole.  These compounds may also contain halogen atoms, tertiary nitrogen atoms, or alkyl, hydroxyalkyl, nitro, hydroxy or carboxylic groups.  Suitable catalysts are the oxides, hydroxides, alcoholates, phenolates and naphtholates of the alkali metals, the oxides of zinc and cadmium, and the salts of the said metals with organic acids, e.g. their acetates, with or without mercury compounds, e.g. mercuric oxide, also active carbon, fuller's earth and silica gel.  The reaction may be carried out discontinuously or continuously at about 50--250 DEG  C., preferably at 100--180 DEG  C., preferably in the liquid phase, if desired in the presence of solvents or diluents, e.g. alcohols, ketones, ethers or hydrocarbons.  Atmospheric pressure, where possible, or, preferably, increased pressure may be employed, the acetylene being diluted, in the latter case, with inert gases, e.g. nitrogen or ethane.  The products may be used for the preparation of dyestuffs, in some cases as dyestuffs themselves, or as assistants in the textile and related industries.  In examples, acetylene, diluted with nitrogen, is reacted under pressure with: (1) p-toluene-sulphinic acid and diethylamine or monoethylaniline, in xylene or butanol solution, in the presence of zinc and cadmium oxides or of potassium hydroxide, or in the absence of catalysts; (2) p-toluenesulphinic acid and piperidine or ammonia, in xylene solution, in the presence of zinc and cadmium oxides; 93) p-toluenesulphinic acid ammonium salt and ammonia, in butanol solution, in the presence of potassium hydroxide; (4) p-toluenesulphinic acid phenylhydrazine salt and phenylhydrazine, in xylene solution, in the presence of potassium hydroxide and zinc and cadmium oxides; (5) 1 : 3-benzenedisulphinic acid or a -b -ethanedisulphinic acid diethylamine salts and diethylamine, in xylene solution in the presence of potassium hydroxide.