GB676849A - Production of salts of basic ethers - Google Patents

Abstract

The invention comprises arylsulphonates of asymmetrical basic ethers, of the general formul Ar2CH . O . CH2CH2 . NHR2 . SO3Ar1 (wherein R represents hydrogen, methyl or ethyl, Ar1 phenyl or tolyl and Ar phenyl, tolyl, anisyl or halogenated phenyl), and R1.O.CH2CH2.NHR2.SO3Ar (wherein R represents hydrogen, methyl or ethyl, Ar phenyl or tolyl and R1 an alkyl group of more than 5 carbon atoms); and the manufacture of these and other salts of asymmetrical basic ethers and salts of symmetrical basic ethers by heating, with removal of water, one or more strong acid salts of a primary or secondary alcohol containing at least one basic group, alone or with one or more neutral primary or secondary alcohols having more than 5 carbon atoms. The reaction may be effected in a solvent (e.g. o-dichlorobenzene, trichlorobenzene or symm.-tetrachloroethane, or mixtures of the last-named with a solvent capable of entraining the liberated water by azeotropic distillation, such as carbon tetrachloride, benzene or toluene), but in some cases the presence of a solvent is unnecessary. It may also be advantageous to use a dehydration catalyst (e.g. a strong acid, advantageously excess of the acid used to form a salt with the basic alcohol), and to pass a current of inert gas through the reaction mixture or to apply reduced pressure thereto. Specified starting materials, some of which are employed in examples, are: salts of basic alcohols: salts of ethanolamine, 1-amino-3-hydroxypropane, 1-amino - 5 - hydroxypentane, tropeine, N - hydroxyethylpiperidine, N - hydroxyethylmorpholine, pseudotropeine, b -dialkylaminoethanols (e.g. diethylaminoethanol), dialkylaminoisopropanols (e.g. dimethylaminoisopropanol), N - butylethanolamine, N - diethylleucinol, 2 - methyloliminazoline, N - methylpiperidol - 4, 2 - methyl - 2 - butylaminopropanol and a -pyridylphenylcarbinol, with sulphonic acids (e.g. methane-, ethane-, benzene-, toluene- and naphthalene-sulphonic acids and ethane-1 : 2-disulphonic acid) and inorganic acids (e.g. hydrochloric, hydrofluoric, hydrobromic, sulphuric and perchloric acids), also quaternary ammonium salts containing a primary or secondary alcohol group (e.g. trimethylhydroxyethylammonium benzenesulphonate or p-toluenesulphonate, and dimethyl-n-octylhydroxyethylammonium bromide); neutral alcohols: fatty alcohols (e.g. hexyl, iso-octyl, dodecyl, cetyl and octadecyl alcohols), p-chlorobenzyl alcohol, benzhydrol and its nuclear halogen, lower alkyl or lower alkoxy substitution products (e.g. p-chloro-, p-methyl-, p-methoxy- and p : p1-dimethyl-benzhydrol). Specifications 605,915, 605,916, 606,317 and 607,258 and U.S.A. Specifications 2,421,714, 2,427,878, 2,437,711, 2,453,729, 2,454,092 and 2,455,949 are referred to.