Patent GB-586688-A (GB)
Title: Manufacture of quaternary ammonium compounds
IPC: C07D213/20
Filed: 1944-08-01
Abstract: Normal quaternary ammonium compounds are prepared by: treating a quaternary ammonium compound containing at least two hydroxyl groups with an acylating agent so as to acylate both groups with the residue of a carboxylic acid containing 5-10 carbon atoms in an uninterrupted series; by esterifying both carboxyl groups of a dicarboxylic acid containing a quaternary ammonium group with an alcohol containing 5-10 carbon atoms in an uninterrupted series; or by treating an ester containing a tertiary amino group and at least one residue of an alcohol or carboxylic acid having 5-10 carbon atoms in an uninterrupted series with the ester derived from a halogencarboxylic acid and an alcohol containing 5-10 carbon atoms in an uninterrupted series or from a halogen-alcohol and a carboxylic acid having 5-10 carbon atoms in an uninterrupted series.  Thus, a quaternary ammonium salt containing at least two hydroxyl groups, for example an addition product of a glycerin monohalohydrin and a tertiary amine, such as dihydroxypropyl - pyridinium, -trimethyl - ammonium or -dimethyl-cyclohexyl-ammonium or tri - (hydroxyethyl) - benzyl - ammonium chloride, may be acylated with a carboxylic acid of 5-10 carbon atoms, e.g. caproic, caprylic, capric, benzoic or a naphthenic acid, or a functional derivative thereof, as by treating with the acid chloride in the presence of pyridine or other acid-binding agent at about 100 DEG  C.; a dicarboxylic acid containing a quaternary ammonium group, for example an addition compound of a tertiary amine and a halogensuccinic acid such as monobrom-succinic acid, may be esterified with an alcohol of 5-10 carbon atoms such as amyl alcohol, 2-ethylbutanol-1, n-octyl alcohol or 2-ethylhexanol-1; or an ester of a halogen-carboxylic acid with an alcohol of 5-10 carbon atoms or of a halogenalcohol and a carboxylic acid of 5-10 carbon atoms, for example 2-ethylhexyl chloracetate or b -bromethyl caprylate, may be combined additively with an ester containing a tertiary amino group and at least one residue derived from an alcohol or acid of 5-10 carbon atoms, for example b -(diethylamino)-ethyl caprylate. Mixtures of the said alcohols or acids used as starting materials may be used, such as the first runnings of fatty acids obtained by oxidation of paraffin.  The products are wetting agents and are used as textile assistants, and disinfectants.  In examples: (1) a ,b -dihydroxypropyl-pyridinium chloride is treated in pyridine at 98 DEG C. with caprylic acid chloride to give a product forming a foaming solution with water; (2) caproic acid chloride replaces caprylic; (3) 2-ethylhexyl monochloracetate and b -(diethylamino)-ethyl caprylate are heated at 98 DEG  C. to give an oil forming a foaming solution with water; (4) an aqueous solution of the product of (1) is used for wetting wool yarn.  The Specification as open to inspection under Sect. 91 comprises also the following methods of preparation: treating with tertiary amines such as pyridine, trimethylamine or dimethylcyclohexylamine, esters of halogen-alcohols which are at least dihydric with the aforesaid carboxylic acids, e.g. dicapryl-glycerin-monobromhydrins; treating with an alkylating or aralkylating agent, e.g. dimethyl sulphate, an amino-ester containing a tertiary amino group and at least two hydroxyl groups esterified with the said carboxylic acids, e.g. the dicaprylic ester of 1-diethylamino-2,3-dihydroxy-propane; or esterifying a dicarboxylic acid containing a substituent, such as a halogen atom or tertiary amino group, convertible into a quaternary ammonium group, e.g. 2-diethylamino-succinic acid, with an alcohol of 5-10 carbon atoms, and converting the said convertible group.  This subject-matter does not appear in the Specification as accepted.