Patent GB-435290-A (GB)
Title: Improvements in or relating to the manufacture of water soluble mineral acid derivatives of alkylamines of high molecular weight
Filed: 1934-08-20
Abstract: Products stated to have wetting, washing, emulsifying, foaming, and dispersing properties are prepared: (a) by treating glycols having at least six carbon atoms with hydrogen halide, converting one of the ester groups so introduced into a sulphonic group by means of a sulphite or a sulphide followed by oxidation and reacting the other ester group with ammonia or primary or secondary amines; (b) by treating glycols having at least six carbon atoms with polybasic oxygen containing mineral acids and reacting one of the ester groups so introduced with ammonia or primary or secondary amines including heterocyclic bases, e.g. piperidine; (c) by esterifying only one of the hydroxy groups of the higher glycols by means of hydrogen halide or polybasic oxygen containing mineral acids, reacting the ester group with ammonia or primary or secondary amines and esterifying the remaining hydroxy group with a polybasic oxygen containing mineral acid; (d) by treating the higher glycols as in (c) above, but instead of esterifying with polybasic oxygen containing mineral acids in the final step, esterifying with hydrogen halide and treating with sulphites or with sulphides followed by oxidation.  The amino esters which are produced may be acylated.  The higher glycols may be prepared by reducing aliphatic, aromatic-aliphatic or cycloaliphatic oxy or keto carboxylic acids or dicarboxylic acids. In examples: (1) 1 : 6-hexanediol or ricinoleic alcohol is esterified with hydrochloric acid, treated with diethylamine and the resulting amino alcohol converted into the sulphuric ester; (2) decanediol is converted into the bromhydrin with hydrobromic acid, esterified with sulphuric acid and reacted with sodium disulphide; the sulphuric ester group is then replaced by treating with butylamine and the sulphide group oxidized with nitric acid in the presence of vanadium pentoxide; finally the butylamino group may be acetylated; (3) 1 : 8-octanediol is treated with sulphuric acid, the o -oxyoctylsulphuric ester reacted with piperidine which replaces the sulphuric ester group, and the resulting o -piperidinooctylalcohol esterified with sulphuric acid; the latter has soap-like properties and may be converted with a true sulphonic acid by means of sulphurizing agents followed by oxidation.  The use of the products in the textile, paper, and leather industries is referred to.ALSO:Products stated to have emulsifying, and dispersing properties are prepared: (a) by treating glycols having at least six carbon atoms with hydrogen halide, converting one of the ester groups so introduced into a sulphonic group by means of a sulphite or a sulphide followed by oxidation and reacting the other ester group with ammonia or primary or secondary amines; (b) by treating glycols having at least six carbon atoms with polybasic oxygen containing mineral acids and reacting one of the ester groups so introduced with ammonia or primary or secondary amines including heterocyclic bases, e.g. piperidine; (c) by esterifying only one of the hydroxy groups of the higher glycols by means of hydrogen halide or polybasic oxygen containing mineral acids, reacting the ester group with ammonia or primary or secondary amines and esterifying the remaining hydroxy group with a polybasic oxygen containing mineral acid; (d) by treating the higher glycols as in (c) above but instead of esterifying with polybasic oxygen containing mineral acids in the final step, esterifying with hydrogen halide and treating with sulphites or with sulphides followed by oxidation.  The amino esters which are produced may be acylated.  In examples: (1) 1 : 6-hexanediol or ricinoleic alcohol is esterified with hydrochloric acid, treated with diethylamine and the resulting amino alcohol converted into the sulphuric ester; (2) decanediol is converted into the bromhydrin with hydrobromic acid, esterified with sulphuric acid and reacted with sodium disulphide; the sulphuric ester group is then replaced by treating with butylamine and the sulphide group oxidized with nitric acid in the presence of vanadium pentoxide; finally the butylamino group may be acetylated; (3) 1 : 8-octanediol is treated with sulphuric acid, the o -oxyoctylsulphuric ester reacted with piperidine which replaces the sulphuric ester group, and the resulting o -piperidinooctyl-alcohol esterified with sulphuric acid; the latter has soap like properties and may be converted into a true sulphonic acid by means of sulphurizing agents followed by oxidation.