Patent GB-693086-A (GB)
Title: Improvements relating to the preparation of alkylolamides
IPC: C07C233/16
Filed: 1951-09-21
Abstract: Alkylolamides are prepared by condensing a carboxylic halide with an alkylolamine in an aqueous solution containing a stable water-immiscible solvent for the alkylolamide to be produced and an acceptor for the liberated hydrogen halide and separating the alkylolamide from the aqueous mass and from the solvent. Suitable solvents are, for example, benzene, toluene, octane, iso-octane, heptane, carbon tetrachloride, chloroform, ethyl ether, isopropyl ether, n-butyl ether, amyl ether, dipropyl ketone, diisopropyl ketone, dibutyl ketone and diisobutyl ketone. Suitable acceptors for the hydrogen halide are potassium hydroxide, sodium hydroxide, lithium hydroxide, potassium carbonate, sodium carbonate, lithium carbonate, sodium bicarbonate, potassium bicarbonate, lithium bicarbonate, magnesium hydroxide and organic amines having a non-replaceable hydrogen atom, e.g. triethylamine and trimethylamine. Alkylolamine compounds suitable for amidation are, for example, monoethanolamine, diethanolamine, monopropanolamine, dipropanolamine, dibutanolamine, monobutanolamine, monoisobutanolamine, mono- and di-pentanolamine, mono- and di, hexanolamine, mono- and di-octanolaminemono - laurylolamine, mono - hexadecylolamine, mono - ethyl ethanolamine, monooctadecylolamine, mono - butyl ethanolamine, arylalkylolamines, cyclohexyl ethanolamine, ethanolaniline, 2 - methyl - amino - propanediol - 1,3, 1 - phenyl - amino - propanediol-2,3, 1 - hydroxy - ethyl - amino - 2 - methoxypropan-ol-3, diglycerol monoamine and diglyceroldiamine.  The carboxylic acid halides may be derived from cyclic and acyclic, saturated and unsaturated acids.  The condensation reaction between the alkylolamine and the carboxylic acid halide is preferably carried out at a pH of about 8.5 to 9, and at a temperature in the range 15-30 DEG  C.  In the examples (a) lauroyl chloride is prepared from lauric acid and phosphorus trichloride and added to a mixture of diethanolamine dissolved in water and ethylene dichloride; caustic potash is added and lauric diethanolamide with small amounts of lauric acid and diethanolamic ester are obtained; (b) phosphorus trichloride is reacted with coconut oil fatty acid to give the acid chloride which is condensed with diethanolamine in the presence of an aqueous p  solution of potassium hydroxide and ethylene dichloride; coconut oil diethanolamide with small amounts of coconut oil fatty acid and diethanolamine ester are obtained.ALSO:Alkylolamides obtained by condensing a carboxylic acid halide with an alkylolamine may be used as wetting agents in the p  laundering, textile, cosmetic, plastic and leather industries. The term "alkylolamines" covers simple alkylolamines, arylalkylolamines and cycloalkylolamines.  The carboxylic acid halides may be the halides of cyclic, acyclic, saturated and unsaturated carboxylic acids or of a mixture of these or of a mixture with higher fatty acids derived from oils such as coconut, palm kernel, palm, olive, cottonseed, corn and peanut oils.  In an example, coconut oil diethanolamide, containing a little coconut oil fatty acid and diethanolamine ester as byproducts, is stated to be suitable for incorporation into a detergent composition.