Patent GB-475170-A (GB)
Title: Manufacture of new derivatives of aliphatic acid amides
IPC: C07D215/10
Filed: 1936-05-13
Abstract: Quaternary ammonium salts are obtained by the reaction of an aliphatic carboxylic acid amide and formaldehyde with a salt of pyridine or of an alkylpyridine or quinoline or with an addition product of any of these amines with an inorganic acid anhydride, the reaction being effected in the presence of free pyridine, alkylpyridine, or quinoline.  The same products are obtainable also by reacting an aliphatic carboxylic acid hydroxymethylamide (obtainable from an aliphatic carboxylic acid amide and formaldehyde) with a salt of one of the specified tertiary amines or with an addition product thereof with an inorganic acid anhydride, this reaction also being effected in the presence of free tertiary amine, as specified above.  The reaction may be effected at 50--100 DEG  C. in the presence or absence of a diluent, which may be chloroform, benzene or toluene or a sufficient excess of free tertiary amine.  In place of formaldehyde, a polymer such as paraformaldehyde may be used.  Specified carboxylic acid amides are acetamide, propionamide, oleic amide, lauramide, stearamide, and amides of the acids of coconut oil, palm oil, cotton seed oil or tallow or of the acids obtainable from hydrogenated fats.  Suitable tertiary amine salts are the hydrochloride, hydrobromide, sulphate, nitrate, m-nitrobenzene sulphonate and p-toluenesulphonate of pyridine or of an alkylpyridine or quinoline; the addition products of pyridine with sulphur trioxide and sulphur dioxide may also be used.  As alkylpyridines picolines and lutidines are specified, or use may be made of technical pyridine bases.  The products are of the type RCONHCH2N­X, where RCO is the radicle of an aliphatic carboxylic acid, X is a monovalent anion, and N­ indicates a p  pyridine, alkylpyridine or quinoline molecule; they yield foaming aqueous solutions and are useful as textile assistants. Examples are given of the manufacture of products from (1) stearohydroxymethylamide and the addition product of pyridine and sulphur trioxide, free pyridine being present; (2) stearohydroxymethylamide, pyridine hydrochloride, and pyridine; (3) stearamide, paraformaldehyde, pyridine hydrochloride, hydrobromide, nitrate or m-nitrobenzene sulphonate, and pyridine; (4) lauramide (or the amides of coconut oil acids), paraformaldehyde, pyridine hydrochloride, and pyridine; (5) propionamide, paraformaldehyde, pyridine hydrochloride, and pyridine; (6) acetamide, paraformaldehyde, pyridine hydrochloride, and pyridine; (7) stearamide, paraformaldehyde, and the addition product of pyridine and sulphur trioxide, free pyridine being present; (8) oleic acid hydroxymethylamide, pyridine hydrochloride, and pyridine; (9) stearohydroxymethylamide, pyridine oxalate or p-toluenesulphonate, and pyridine; (10) stearohydroxymethylamide, quinoline hydrochloride, and quinoline; (11) propionohydroxymethylamide, pyridine hydrochloride, and pyridine; (12) stearohydroxymethylamide, pyridine nitrate, and pyridine.  Specification 317,736, [Class 2 (iii)], is referred to.  Stearohydroxymethylamide is obtainable by treating stearamide with paraformaldehyde at 50 DEG  C. in benzene in the presence of potassium carbonate.