Process for the reductive amination of aldehydes and ketones

A method for reductively aminating a starting aldehyde or ketone compound having at least two aldehyde or ketone groups per molecule to form a product amine compound, comprising

• a) mixing product amine compound and starting aldehyde or ketone compound at a molar ratio of at least about 1:1 and an alcohol solvent to form a liquid mixture, and maintaining the liquid mixture under non-reductive amination conditions sufficient to form an intermediate mixture containing reaction intermediates formed from the product amine compound and the starting aldehyde or ketone compound, which reaction intermediates consist predominantly of one or more macrocyclic polyimine compounds;
• and
• b) thereafter subjecting at least one of the macrocyclic polyimine compounds to reductive amination conditions in the presence of ammonia and hydrogen to convert the macrocyclic polyimine compound to the product amine compound.

A method for reductively aminating a starting aldehyde or ketone compound having at least two aldehyde or ketone groups per molecule to form a product amine compound, the method comprising:

• subjecting a liquid mixture containing one or more macrocyclic polyimine compounds and an alcohol solvent to reductive amination conditions in the presence of ammonia and hydrogen to convert the cyclic polyimine compound(s) to the product amine compound;
• wherein the macrocyclic polyimine compound(s) predominantly contains species of 450 to 1500 molecular weight.

A method for reductively aminating an alicyclic dialdehyde or alicyclic diketone compound in which the carbonyl carbons of the aldehyde or ketone groups are attached directly to an alicyclic ring structure, to form a product alicyclic diamine compound, the method comprising:

• a) mixing product alicyclic diamine compound and the starting alicyclic aldehyde or alicyclic ketone compound at a molar ratio of at least about 1:1 and an alcohol solvent to form a liquid mixture, and maintaining the liquid mixture at a temperature of about 0 to about 50° C. for a period of at least 5 minutes to form an intermediate mixture;
• and
• b) thereafter subjecting at least one component of the intermediate mixture to reductive amination conditions in the presence of ammonia and hydrogen to form the product alicyclic diamine compound.