Patent GB-459746-A (GB)
Title: Improvements in the manufacture and production of amines containing two hydroxyalkylamino groups
IPC: B01J19/08
Filed: 1936-01-29
Abstract: Amines containing two hydroxyalkylamino groups are prepared by treating primary or secondary amines containing at least one hydroxyalkyl group with dihalogenated aliphatic compounds, the carbon chain of which may be interrupted by hetero atoms or groups, such as an oxygen atom or an imino group, or may be substituted by hetero atoms or groups containing them, except on the carbon atoms to which the halogen atoms are attached. Specified amines for use as starting materials are ethanolamine, isopropanolamine, butanolamine, dodecanolamine, octadecanolamine, diethanolamine, dipropanolamine, dibutanol amine, ethanolbutanolamine, methylethanolamine, ethylethanolamine, butylethanolamine, amylbutanolamine, dodecylethanolamine, octadecenylethanolamine, phenylpropanolamine, and cyclohexylethanolamine.  Specified dihalogenated aliphatic compounds are ethylene chloride and bromide, 2 : 2<1>-dichlorodiethylamine, 1 : 3-dibromopropane, 1 : 2-dichlorobutane, 2 : 2<1>-dichlorodiethyl ether, a , g -(or a , b -)dichlorhydrin and their homologues, and alkylene iodides and fluorides.  The reaction is preferably effected at 100--200 DEG  C. in the absence of water.  The bases are useful as emulsifying agents, and those of lower molecular weight are useful as absorbents for gases (cf. Specification 450,519); the salts of the bases are useful as wetting and washing agents in the textile, leather and paper industries, the salts with hydrochloric, sulphuric, nitric, acetic, oxalic and lauric acids being specified.  In the examples: (1) ethanolamine and ethylene chloride yield N : N<1>-di(hydroxyethyl)ethylenediamine; (2) methylethanolamine and ethylene chloride (or bromide) yield N : N<1>-dimethyl-N : N<1>-di(hydroxyethyl)ethylenediamine; (3) butylethanolamine and 2 : 2<1>-dichlorodiethyl ether yield N : N<1>-dibutyl-N : N<1>-di(hydroxyethyl)-2 : 2<1>-diaminodiethyl ether; (4) isopropanolamine and a , g -dichlorhydrin yield N : N<1>-di(2-hydroxypropyl) - 1 : 3 - diamino - 2 - hydroxypropane; similar products are obtainable from a , b -dichlorhydrin and ethanolamine, methylethanolamine and ethylethanolamine.  Reference is made also to the reaction of a dihalogenated aliphatic compound (as defined above) with two different alkylolamines.ALSO:Amines containing two hydroxyalkylamino groups are prepared by treating primary or secondary amines containing at least one hydroxyalkyl group with dihalogenated aliphatic compounds, the carbon chain of which may be interrupted by hetero atoms or groups, such as an oxygen atom or an imino group, or may be substituted by hetero atoms or groups containing them, except on the carbon atoms to which the halogen atoms are attached. Specified amines for use as starting materials are ethanolamine, isopropanolamine butanolamine, dodecanolamine, octadecanolamine, diethanolamine, dipropanolamine, dibutanolamine, ethanolbutanolamine, methylethanolamine, ethylethanolamine, butylethanolamine, amylbutanolamine, dodecylethanolamine, octadecenylethanolamine, phenylpropanolamine, and cyclohexylethanolamine.  Specified dihalogenated aliphatic compounds are ethylene chloride and bromide, 2 : 2<1>-dichlorodiethylamine, 1 : 3-dibromopropane, 1 : 2-dichlorobutane, 2 : 2<1>-dichlorodiethyl ether, a , g  - (or a , b -) dichlorhydrin and their homologues, and alkylene iodides and fluorides.  The bases are useful as emulsifying agents, and those of lower molecular weight are useful as absorbents for gases (cf. Specification 450,519).  In the examples, (1) ethanolamine and ethylene chloride yield N : N<1>-di(hydroxyethyl)ethylenediamine; (2) methylethanolamine and ethylene chloride (or bromide) yield N : N<1>-dimethyl-N : N<1>-di(hydroxyethyl)ethylenediamine; (3) butylethanolamine and 2 : 2<1>-dichlorodiethyl ether yield N : N<1>-dibutyl-N : N<1>-di(hydroxyethyl)-2 : 2<1>-diaminodiethyl ether; (4) isopropanolamine and a , g -dichlorhydrin yield N : N<1>-di(2-hydroxypropyl)-1 : 3-diamino-2-hydroxypropane; similar products are obtainable from a , b -dichlorhydrin and ethanolamine, methylethanolamine and ethylethanolamine.  Reference is made also to the reaction of a dihalogenated aliphatic compound (as defined above) with two different alkylolamines.