Ethers of alpha-glycerylamine
Номер патента: GB747189A
Опубликовано: 28-03-1956
Автор(ы):
Принадлежит: Union Carbide and Carbon Corp
Опубликовано: 28-03-1956
Автор(ы):
Принадлежит: Union Carbide and Carbon Corp
Реферат: The invention comprises as new products gamma alkoxy ethers of alpha-glycerylamine having the formula <F> in which R is a hydrogen atom or a methyl group and n is 1 or 2. They may be prepared by reacting in the liquid phase an alkoxy glycidyl ether having the formula <FORM:0747189/IV(a)/1> with ammonia, R being as defined above. The ether is generally added slowly to an aqueous solution of ammonia although any other solvent for the ammonia may be used. The reaction is preferably carried out at 10 DEG to 60 DEG C. In another method the corresponding alpha glyceryl chlorhydrin (CH3(OC2H3R)nOCH2CHOHCH2Cl) instead of the glycidyl ether is reacted with ammonia in the liquid phase. In examples: (1) the gamma-(methoxyethyl) ether of alpha-glycerylamine is obtained by adding the glycidyl ether of methoxy ethanol to aqueous ammonia, cooling to maintain the temperature at not more than 35 DEG C. and when the reaction is complete heating to expel unreacted ammonia, removing water by distillation in a fractionating column at reduced pressure and then fractionally distilling the residue to yield the glycerlamine ether; (2) the same product is obtained as in (1) by heating a mixture of gamma-(methoxyethyl) ether of alpha-glycerylchlorhydrin and an aqueous solution of ammonia to 60 DEG C. for three hours, cooling, adding an aqueous concentrate of sodium hydroxide, removing unreacted ammonia and water as in (1), filtering to remove salt, and then fractionally distilling the product to yield the glycerylamine ether; (3) gamma-(methoxyethoxyethyl) ether of alpha-glycerylamine is obtained by reacting methoxyethoxyethyl glycidyl ether with aqueous ammonia by a procedure similar to (1); (4) and (5) gamma-(2-methoxypropyl) ether of alpha-glycerylamine and gamma - (2 - methoxy - 2 - propoxypropyl) ether of alpha-glycerylamine respectively are obtained by reacting (2-methoxypropyl) ether of glyceryl amine (mixed isomers) and the glycidyl ether of dipropylene glycol monomethyl ether (mixed isomers) respectively with aqueous ammonia by a procedure similar to (1). It is stated that some secondary amine may also be formed in (3) and (4). The products are stated to be useful as soap formers in cosmetic compositions and the amide derivatives formed by reacting the products with stearic, lauric, palmitic, or oleic acid exhibit surface-active properties and are useful as non-ionic detergents, dispersants and emulsifying agents. The alkoxy glycidyl ethers used as starting materials may be prepared by adding a monomethyl ether of a glycol to epichlorhydrin at a temperature not above 80 DEG C. for about two hours to form the glyceryl chlorhydrin ether of the glycol ether which is then reacted with caustic soda to form the corresponding glycidyl ether; thus epichlorhydrin and methoxy ethanol react to give the glyceryl chlorhydrin ether of methoxy ethanol which on treatment with caustic soda yields the glycidyl ether of methoxy ethanol.
Process for the preparation of aminoalkyl ethers of alcohols of the aromatic-aliphatic series
Номер патента: DE853164C. Автор: Henry Dr Martin,Karl Dr Gaetzi,Adolf Dr Grob,Franz Dr Hoefliger. Владелец: Parke Davis and Co LLC. Дата публикации: 1952-10-23.