Catalytic hydrogenation of unsaturated dinitriles employing palladium and ruthenium as catalyst

Claim 2

A PROCESS FOR THE CATALYTIC HYDROGENATION OF AN UNSATURATED DINITRILE FEEDSTOCK COMPRISING AT LEAST ONE UNSATURATED DINITRILE COMPOUND OF THE FORMULA:

Claim 3

A process in accordance with claim 1, wherein said feedstock further comprises at least one unsaturated dinitrile reactant of the formula:

Claim 4

A process in accordance with claim 1 wherein at least one of said catalyst components together with a solid catalyst support forms a catalyst composition, the content of the elemental metal in said catalyst composition being in the range of about 0.5 to about 50 weight percent of said catalyst composition.

Claim 5

A process in accordance with claim 1 wherein each of said alkylene radical, said alkylidene radical and said alkyl radical has from 1 to 15 carbon atoms, and wherein said diluent further comprises at least one material selected from the group consisting of unsubstituted alkanols having 2 to 12 carbon atoms per molecule, unsubstituted acyclic and unsubstituted cyclic ethers having 4 to 12 carbon atoms per molecule, and hydrocarbons having from 4 to 12 carbon atoms per molecule.

Claim 6

A process in accordance with claim 1 wherein said at least one unsaturated dinitrile compound comprises a mixture of 5-methyl-4-nonenedinitrile, 2,4-dimethyl-4-octenedinitrile, 2,4-dimethyl-3-octenedinitrile, and 2,4,6-trimethyl-3-heptenedinitrile.

Claim 7

A process in accordance with claim 1 wherein said hydrogenation conditions comprise a weight ratio of the total of a palladium and ruthenium present to the unsaturated dinitriles in the range of about 0.01:100 to about 30:100, a mol ratio of ammonia to cyano groups in the range of about 1:1 to about 25:1, a hydrogen pressure in the range of about 500 to about 5000 psig, a weight ratio of the unsaturated dinitriles to the diluent in the range of about 0.001:100 to about 15:100, a weight ratio of palladium to ruthenium in the range of about 0.1:10 to about 10: 1; a temperature in the range of about 80* C to about 250* C, and a reaction time in the range of about 15 minutes to about 5 hours if conducted as a batch process or a liquid hourly space velocity rate in the range of about 0.1 to about 10 volumes of unsaturated dinitrile plus diluent per volume of catalyst if conducted as a continuous process.

Claim 8

A process in accordance with claim 1 wherein said hydrogenation conditions comprise a weight ratio of the total of palladium and ruthenium present to the unsaturated dinitriles in the range of about 0.1:100 to about 10:100, a weight ratio of palladium to ruthenium in the range of about 1:1 to about 4:1, a mol ratio of ammonia to cyano groups in the range of about 7:1 to about 15:1, a hydrogen pressure in the range of about 1000 to about 3000 psig, a weight ratio of the unsaturated dinitriles to the diluent in the range of about 0.1:100 to about 12:100, a temperature in the range of about 100* C to about 250* C, and said diluent comprises at least 50 volume percent methanol.

Claim 9

A process in accordance with claim 7 wherein said feedstock further comprises at least one unsaturated dinitrile reactant of the formula:

Claim 10

A process in accordance with claim 8 wherein said first catalyst component is palladium on carbon, said second catalyst component is ruthenium on alumina, and said diluent is methanol.

Claim 11

A process in accordance with claim 8 wherein each of said alkylene radical, said alkylidene radical and said alkyl radical has from 1 to 6 carbon atoms.

Claim 12

A process in accordance with claim 1 further comprising recovering a diamine product containing less than about 1 weight percent unsaturated diamines.

Claim 13

A process in accordance with claim 1 further comprising recovering a diamine product essentially free of unsaturation.

Claim 14

A process in accordance with claim 2 wherein said feedstock comprises 5-methylene-nonanedinitrile and 5-methyl-4-nonenedinitrile.