Catalytic hydrogenation of unsaturated dinitriles

Claim 2

A PROCESS FOR THE CATALYTIC HYDROGENATION OF AN UNSATURATED DINITRILE FEED STOCK CONTAINING AT LEAST ONE UNSATURATED DINITRILE COMPOUND OF THE FORMULA:

Claim 3

A process in accordance with claim 1 wherein said hydrogenation conditions comprise a weight ratio of the total of ruthenium and/or palladium, and cobalt and/or nickel 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 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 if conducted as a continuous process.

Claim 4

A process in accordance with claim 1 wherein said catalyst 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 one to 15 carbon atoms, and wherein said diluent further comprises at least one material selected from the group consisting of unsubstituted alkanols having two to 12 carbon atoms per molecule, unsubstituted acyclic and unsubstituted cyclic ethers having four to 12 carbon atoms per molecule, and hydrocarbons having from four to 12 carbon atoms per molecule.

Claim 6

A process in accordance with claim 2, 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 further comprising recovering a diamine product essentially free of unsaturation.

Claim 8

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

Claim 9

A process in accordance with claim 7 wherein said first catalyst component comprises ruthenium dioxide and said second catalyst component comprises Raney cobalt.

Claim 10

A process in accordance with claim 7 wherein said first catalyst component comprises palladium and said second catalyst component comprises Raney nickel.

Claim 11

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

Claim 12

A process in accordance with claim 10 wherein said hydrogenation conditions comprise a weight ratio of the total of ruthenium and/or palladium, and cobalt and/or nickel present to the unsaturated dinitriles in the range of about 0.1:100 to about 20:100, 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 1,000 to about 3,000 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 a reaction time 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 if conducted as a continuouS process; said at least one unsaturated dinitrile compound constituting at least 5 weight percent of the unsaturated dinitriles in said feedstock; wherein said at least one dinitrile compound is converted primarily to a saturated diamine having the formula:

Claim 13

A process in accordance with claim 11 wherein said first catalyst component is selected from the group consisting of elemental ruthenium, ruthenium compounds which are reducible by hydrogen to elemental ruthenium at said hydrogenation conditions, and mixtures thereof, and wherein the contacting step is carried out at a temperature in the range of about 100* to about 250* C.

Claim 14

A process in accordance with claim 12 wherein said second catalyst component is selected from the group consisting of elemental nickel, nickel compounds which are reducible by hydrogen to elemental nickel at said hydrogenation conditions, and mixtures thereof.

Claim 15

A process in accordance with claim 12 wherein said second catalyst component is selected from the group consisting of elemental cobalt, cobalt compounds which are reducible by hydrogen to elemental cobalt at said hydrogenation conditions, and mixtures thereof.

Claim 16

A process in accordance with claim 11 wherein said first catalyst component is selected from the group consisting of elemental palladium, palladium compounds which are reducible by hydrogen to elemental palladium at said hydrogenation conditions, and mixtures thereof, and wherein the contacting step is carried out at a temperature in the range of about 100* to about 250* C.

Claim 17

A process in accordance with claim 15 wherein said second catalyst component is selected from the group consisting of elemental nickel, nickel compounds which are reducible by hydrogen to elemental nickel at said hydrogenation conditions, and mixtures thereof.

Claim 18

A process in accordance with claim 15 wherein said second catalyst component is selected from the group consisting of elemental cobalt, cobalt compounds which are reducible by hydrogen to elemental cobalt at said hydrogenation conditions, and mixtures thereof.

Claim 19

A process in accordance with claim 11 wherein said feedstock comprises 5-methylenenonanedinitrile and 5-methyl-4-nonenedinitrile.