Patent EP-0031089-A1 (EP)
Inventor: MOHR REINHARD DR
IPC: C07D295/02
Filed: 1980-12-11
Abstract: 1. Process for the preparation of N,N'-diaryl-alkylene-diamines and N,N',N"-triaryl-dialkylene-triamines of the general formula (1)  see diagramm : EP0031089,P22,F12  in which both A have meanings which are identical to one another or different from one another, and each is an optionally substituted aryl radical, R' and R" have meanings which are identical to one another or different from one another, and each is a hydrogen atom or a lower alkyl group, both R**1 have meanings which are identical to one another or different from one another, and each is a hydrogen atom or an optionally substituted alkyl, aralkyl, aryl or cycloalkyl radical, or one of the R**1 is a group of the general formula (2)  see diagramm : EP0031089,P23,F2  in which R', R" and A have the abovementioned meaning and R**2 is a hydrogen atom or an optionally substituted alkyl, aralkyl, aryl or cycloalkyl radical, R**2 having in formula (2) the same meaning as R**1 of formula (1) or having a meaning which is different from the meaning of R**1 in formula (1), and A having the same meaning to or a different meaning from both A in formula (1), or wherein both R**1 combined together represent a radical of the formula  see diagramm : EP0031089,P23,F6 or  see diagramm : EP0031089,P23,F7  in which R' and R" have the above meaning, in which process a) a beta-hydroxyalkyl-arylamine of the general formula (3)  see diagramm : EP0031089,P23,F9  in which A, R' and R" have the abovementioned meanings and R**3 is an optionally substituted alkyl, aralkyl, aryl or cycloalkyl radical, is reacted with an amine of the general formula (4)  see diagramm : EP0031089,P23,F10  in which A and R**1 have the abovementioned meanings, to form the compound (1) in which both A as well as R' and R" have the abovementioned meanings and one of R**1 is an optionally substituted alkyl, aralkyl, aryl or cycloalkyl radical and the other R**1 is a hydrogen atom or an optionally substituted alkyl, aralkyl, aryl or cycloalkyl radical, or b) a beta-hydroxyalkyl-arylamine of the general formula (3a)  see diagramm : EP0031089,P23,F11  in which A, R' and R" have the abovementioned meanings, is reacted with a beta-hydroxyalkyl-arylamine of the general formula (3b)  see diagramm : EP0031089,P23,F1  in which A, R' and R" have the abovementioned meanings, to form a compound of the formula (6a) or (6b)  see diagramm : EP0031089,P23,F3   see diagramm : EP0031089,P23,F4  in which both A as well as R' and R" have the abovementioned meanings, or c) an alkylene glycol compound of the general formula (5)  see diagramm : EP0031089,P23,F5  in which R' and R" have the abovementioned meanings, or an alkyleneoxide thereof is reacted with an amine of the general formula (4)  see diagramm : EP0031089,P23,F8 in which R**1 and A have the abovementioned meanings, or with two different amines of the formula (4), in which A or R**1 or both have different meanings, to form a compound (1) in which both A as well as R' and R" have the abovementioned meanings and both R**1 , being identical to or different from one another, each represents a hydrogen atom or an optionally substituted alkyl, aralkyl, aryl or cycloalkyl radical, or d) an amine of the above formula (3), in which R**3 represents a group of the above-defined formula (2) and A, R' and R" have the abovementioned meanings, is reacted with an amine of the above formula (4) in which R**1 is a hydrogen atom and A has the abovementioned meaning, to form a compound (1) in which both A as well as R' and R" have the abovementioned meanings, one of the R**1 represents the above-defined group of the formula (2) and the other R**1 is a hydrogen atom, or e) an amine of the above formula (3) in which R**3 is a group of the formula -CH(R')-CH(R")-OH and A, R' and R" have the abovementioned meanings, is reacted with an amine of the above formula (4) in which A and R**1 have the abovementioned meanings, to form a compound (1) in which both A as well as R', R" and one of the R**1 have the abovementioned meanings and the other R**1 represents a radical of the formula (2), or f) an amine of the above formula (3) in which A, R**3 , R' and R" have the abovementioned meanings, is reacted with an amine of the general formula (4) in which A has the abovementioned meaning and R**1 is a hydrogen atom, to form a compound (1) in which both A as well as R', R" and one of the R**1 have the herein mentioned meanings and the other R**1 is a radical of the formula (2), or g) a compound of the formula (4) in which A has the abovementioned meaning and R**1 is hydrogen atom, is reacted with a compound of the formula (5) in which R' and R" have the abovementioned meanings, to form a compound of the above-defined formulae (6a) or (6b) in which both A as well as R' and R" have the abovementioned meanings, or h) a compound of the above formula (3) in which R**3 is a group of the formula -CH(R')-CH(R")-OH and A, R' and R" have the abovementioned meanings, is reacted with a compound of the formula (4) in which A has the abovementioned meaning and R**1 is a hydrogen atom, to form a compound of the above-defined formula (6a) or (6b), characterized by that the reaction of the compounds is carried out in the presence of phosphoric acid or of phosphorous acid in an amount of at least 0.01 mole per mole compound (3) or (5) and at a temperature between 150 and 225 degrees C.