Preparation of N-alkylbis(3-aminopropyl)amines by the catalytic hydrogenation of N-alkylbis(cyanoethyl)amines.
An improved process for the preparation of N-alkylbis(3-aminopropyl)amines is described. These triamines are of interest as monomers for the condensation polymerization with esterified carbohydrate diacids (aldaric acids) to generate the corresponding poly(4-alkyl-4-azaheptamethylene aldaramides). The triamine synthesis is comprised of two efficient steps and requires no chromatographic purification. Bisconjugate addition of alkylamines to acrylonitrile followed by catalytic hydrogenation of the N-alkylbis(cyanoethyl)amines over Raney nickel yields the target N-alkylbis(3-aminopropyl)amines. Much less solvent was used in the bisconjugate addition step then previously reported, and in the second step, a relatively low-pressure catalytic hydrogenation (50 psi of hydrogen) was employed using Raney nickel as the catalyst in a 7 N methanolic ammonia solvent system to afford the N-alkylbis(3-aminopropyl)amines of high purity in nearly quantitative yield.
Denton
Travis T
TT
Shafizadeh Rocky Mountain Center for Wood and Carbohydrate Chemistry, University of Montana, Missoula, Montana 59812, USA.
Joyce
Abigail S
AS
Kiely
Donald E
DE
D000478:Alkylation; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003486:Cyanides / Q000737:chemistry*; D005030:Ethylenes / Q000737:chemistry*; D006865:Hydrogenation; D015394:Molecular Structure; D011407:Propane / Q000737:chemistry*
D000588:Amines; D003486:Cyanides; D005030:Ethylenes; C036216:ethylene; D011407:Propane