Two stage catalytic hydrogenation of unsaturated dinitriles employing ruthenium, nickel or mixture thereof as catalytic agent

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 the catalyst in each reaction zone together with a solid catalyst support forms a catalyst composition, the content of the elemental ruthenium and/or elemental nickel 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.

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 the weight ratios of the total of nickel and ruthenium present in each of said first and second stage reaction zones to the unsaturated dinitriles in the feedstock charged to said first stage reaction zone are in the range of about 0.01:100 to about 30:100, the mol ratio of ammonia to cyano groups in the first stage reaction zone is in the range of about 1:1 to about 25:1, the amount of ammonia in the second stage reaction zone is less than 5 weight percent of the unsaturated dinitriles in the feedstock charged to the first reaction zone, the hydrogen pressure in each of said first and second stage reaction zones is in the range of about 500 to about 5000 psig, the weight ratios of the unsaturated dinitriles in the feedstock charged to said first stage reaction zone to the diluent in each reaction zone are in the range of about 0.001:100 to about 15:100, wherein the temperature in said first stage reaction zone is in the range of about 30*C to about 200*C, wherein the temperature in said second stage reaction zone is in the range of about 100*C to about 250*C, and wherein the reaction time for each of said first and second stage reaction zones in a batch process is in the range of about 15 minutes to about 5 hours and the liquid hourly space velocity rate in said first stage reaction zone in a continuous process is in the range of about 0.1 to about 10 volumes of unsaturated dinitrile plus diluent per volume of catalyst.

Claim 8

A process in accordance with claim 1 wherein the weight ratio of the total of nickel and ruthenium present in each of said first and second stage reaction zones to the unsaturated dinitriles in the feedstock charged to said first stage reaction zone are in the range of about 0.1:100 to about 20:100, the mol ratio of ammonia to cyano groups in the first stage reaction zone is in the range of 7:1 to about 15:1, the amount of ammonia in the second stage reaction zone is less than 1 weight percent of the unsaturated dinitriles in the feedstock charged to the first reaction zone, the hydrogen pressure in each of said first and second stage reaction zones is in the range of about 1000 to about 3000 psig, the weight ratios of the unsaturated dinitriles in the feedstock charged to said first stage reaction zone to the diluent in each reaction zone are in the range of about 0.1:100 to about 12:100, wherein the temperature in said first stage reaction zone is in the range of about 70*C to about 150*C, and wherein the temperature in said second stage reaction zone is in the range of about 125*C to about 200*C.

Claim 9

A process in accordance with claim 7 wherein the catalyst employed in said first stage reaction zone and said second stage reaction zone is selected from the group consisting of elemental ruthenium, ruthenium compounds which are reducible by hydrogen to elemental ruthenium under the hydrogenation conditions employed in said first stage reaction zone, and mixtures thereof.

Claim 10

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 11

A process in accordance with claim 9 wherein said catalyst is ruthenium dioxide and said diluent is methanol.

Claim 12

A process in accordance with claim 7 wherein the catalyst employed in said first stage reaction zone and said second stage reaction zone is selected from the group consisting of elemental nickel, nickel compounds which are reducible by hydrogen to elemental nickel under the hydrogenation conditions employed in said first stage reaction zone, and mixtures thereof.

Claim 13

A process in accordance with claim 11 wherein each of said alkylene radical, said alkylidene radical and said alkyl radical has from 1 to 6 carbon atoms.

Claim 14

A process in accordance with claim 12 wherein said catalyst is Raney nickel and said diluent is t-butyl alcohol.

Claim 15

A process in accordance with claim 7 wherein the catalyst employed in said first stage reaction zone is selected from the group consisting of elemental nickel, nickel compounds which are reducible by hydrogen to elemental nickel under the hydrogenation conditions employed in said first stage reaction zone, and mixtures thereof; and wherein the catalyst employed in said second stage reaction zone is selected from the group consisting of elemental ruthenium, ruthenium compounds which are reducible by hydrogen to elemental ruthenium under the hydrogenation conditions employed in said second stage reaction zone, and mixtures thereof.

Claim 16

A process in accordance with claim 14 wherein the catalyst employed in said first stage reaction zone comprises Raney nickel and the catalyst employed in said second stage reaction zone comprises ruthenium dioxide.

Claim 17

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

Claim 18

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

Claim 19

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