GB379260A - Improvements in and relating to the production of choline compounds - Google Patents

Abstract

Carbonates of choline and its homologues and substitution products, i.e. of quaternary ammonium bases with at least one hydroxyalkyl group, are manufactured by reacting tertiary organic bases with alkylene oxides in the presence of water and carbonic acid. The tertiary bases employed may be aliphatic, aromatic, hydroaromatic, heterocyclic or mixed tertiary nitrogen bases, e.g. trimethylamine, triethanolamine, triphenylamine, dimethylaniline, pyridine and quinoline. From the carbonates, the corresponding salts of other acids can be obtained by simple reaction with evolution of carbon dioxide. The acids which may be employed include halogen hydracids, sulphuric acid, cyanic acid, thiocyanic acid, aliphatic or aromatic acids, e.g. fatty acids, or the sulphonation products of these acids, e.g. sulpho-fatty or sulpho-aromatic acids. In some cases increased temperature is advantageous for this reaction. The products are useful as the basis for pharmaceutical and cosmetic salves, in the leather industry, and in the textile industry as additives for dyeing and sizing baths in consequence of their wetting properties. In examples: (1) ethylene oxide and carbonic acid are introduced into an aqueous solution of trimethylamine, yielding a solution of choline carbonate from which the salt may be obtained by evaporation; (2) ethylene oxide is passed into a solution of triethanolamine saturated with carbonic acid, producing a solution of tetraethanolammonium bicarbonate; (3) an aqueous solution of propylene oxide is added to an aqueous solution of pyridine with simultaneous introduction of carbonic acid, yielding a solution of an oxypropylpyridinium bicarbonate; (4) ethylene oxide and carbonic acid are introduced into an aqueous solution of quinoline to produce oxyethylquinolinium bicarbonate; (5) the solution obtained in (1) is decomposed with thiocyanic acid yielding choline thiocyanate; (6) the product of (2) is decomposed with salicylic acid to produce tetraethanolammonium salicylate; (7) a solution of oxyethylpyridinium bicarbonate (obtained by a process analogous to that of (2)) is decomposed with oleic acid producing the corresponding oleate; (8) dry trimethylethanolammonium carbonate is dissolved in amyl alcohol or xylene and heated with oleic acid.