Patent ID: 9035098
Filing Date: 2015-05-19
Classification: C07C

Abstract:
1. A process for conversion of aliphatic cyclic amines to aliphatic diamines comprising the steps of: selecting one or more bicyclic amines; contacting said one or more bicyclic amines selected from the group consisting of 3-azabicyclo[3.3.1]nonane and azabicyclo[3.3.1]non-2-ene with ammonia and hydrogen, optionally water, and optionally one or more alcohols in the presence of one or more heterogeneous metal based catalyst systems comprising a metal selected from the group consisting of Co, Ni, Ru, Fe, Cu, Re, Pd, oxides thereof, mixtures thereof, and combinations thereof at a temperature in the range of from 140° C. to about 250° C. and a pressure in the range of from 1540 to 1735 psig for a period in the range of at least one hour or more in one or more reactor systems, wherein the ammonia is present in in the range of from 79 to 88 mole equivalent; forming a product mixture comprising one or more aliphatic diamines, a portion of said one or more bicyclic amines, a portion of said ammonia, a portion of said hydrogen, optionally water, and a portion of said one or more solvents; removing said product mixture from the reactor system; removing at least a portion of said portion of ammonia, said portion of hydrogen, or mixture thereof from said product mixture via venting; removing at least a portion of said portion of water via distillation; removing at least a portion of said portion of one or more alcohols via distillation; removing at least a portion of said portion of one or more bicyclic amines; thereby separating said one or more aliphatic diamines from said product mixture; and thereby converting said one or more bicyclic amines selected from the group consisting of 3-azabicyclo[3.3.1]nonane and azabicyclo[3.3.1]non-2-ene to one or more aliphatic diamines selected from the group consisting of 1,3-bis(aminomethyl)cyclohexane and hexamethylene diamine.