Diimines and secondary diamines

A process for forming a secondary diamine, which process comprises mixing together at least one ketone or aldehyde, at least one acid ion exchange resin, at least one hydrogenation agent, and at least one primary diamine,

• I) wherein said primary diamine is an aromatic primary diamine in which at least one position ortho to each amino group has a hydrogen atom as a substituent, where said aromatic primary diamine is either in the form of one phenyl ring having two amino groups on the ring or in the form of two phenyl rings connected by an alkylene bridge and having one amino group on each ring, and wherein said hydrogenation agent is a hydride transfer agent, a dissolving metal reagent, a borane reductant, or hydrogen with a hydrogenation catalyst, wherein said hydrogenation catalyst is sulfided platinum on carbon, sulfided palladium on carbon, or a mixture thereof;
• or
• II) wherein said primary diamine is an aromatic primary diamine in which each position ortho to an amino group bears a hydrocarbyl group, and which aromatic primary diamine is either in the form of one phenyl ring having two amino groups on the ring, which amino groups are meta or para relative to each other or is in the form of two phenyl rings connected by an alkylene bridge and having one amino group on each ring, and wherein said hydrogenation agent is a dissolving metal reagent or hydrogen with a hydrogenation catalyst, where said hydrogenation catalyst is sulfided platinum on carbon, sulfided palladium on carbon, or is selected from the group consisting of palladium on carbon, platinum on carbon, and a mixture of both of these, when used with hydrogen sulfide or at least one strong acid;
• or
• III) wherein said primary diamine is an aliphatic primary diamine, and wherein said hydrogenation agent is a hydride transfer agent, a dissolving metal reagent, a borane reductant, or hydrogen with a hydrogenation catalyst, wherein said hydrogenation catalyst is sulfided platinum on carbon, sulfided palladium on carbon, or a mixture thereof;
• such that a secondary diamine is formed.

A process for forming a diimine, which process comprises mixing together at least one ketone or aldehyde, at least one acid ion exchange resin, and at least one primary diamine, wherein said primary diamine is

• I) an aromatic primary diamine in which at least one position ortho to each amino group has a hydrogen atom as a substituent, and which aromatic primary diamine is either in the form of one phenyl ring having two amino groups on the ring or in the form of two phenyl rings connected by an alkylene bridge and having one amino group on each ring, or
• II) an aromatic primary diamine in which each position ortho to an amino group bears a hydrocarbyl group, and which aromatic primary diamine is either in the form of one phenyl ring having two amino groups on the ring, which amino groups are meta or para relative to each other or is in the form of two phenyl rings connected by an alkylene bridge and having one amino group on each ring, or
• III) an aliphatic primary diamine,
• such that a diimine is formed.

A process for forming a secondary diamine, which process comprises mixing together at least one ketone or aldehyde, hydrogen, at least one primary diamine, and sulfided platinum on carbon, sulfided paladium on carbon, or a mixture thereof, wherein said primary diamine is

• I) an aromatic primary diamine in which at least one position ortho to each amino group has a hydrogen atom as a substituent, and which aromatic primary diamine is either in the form of one phenyl ring having two amino groups on the ring or in the form of two phenyl rings connected by an alkylene bridge and having one amino group on each ring, and wherein said process is conducted at a temperature in the range of about 20° C. to about 120° C. and at a hydrogen pressure in the range of about 14 to about 125 pounds per square inch, or
• II) an aromatic primary diamine in which each position ortho to an amino group bears a hydrocarbyl group, and which aromatic primary diamine is either in the form of one phenyl ring having two amino groups on the ring, which amino groups are meta or para relative to each other or is in the form of two phenyl rings connected by an alkylene bridge and having one amino group on each ring, and wherein said process is conducted at a temperature in the range of about 22° C. to about 140° C. and at a hydrogen pressure in the range of about 14 to about 150 pounds per square inch, or
• III) an aliphatic primary diamine, and wherein said process is conducted at a temperature in the range of about 20° C. to about 140° C. and at a hydrogen pressure in the range of about 14 to about 150 pounds per square inch,
• such that a secondary diamine is formed.