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

Claim 2

A SINGLE STAGE REACTION PROCESS FOR THE CATALYTIC HYDROGENNATION 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 said catalyst 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 said hydrogenation conditions comprise a weight ratio of the total of nickel 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 temperature in the range of about 30* 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 and 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 further comprising recovering a diamine product containing less than about 1 weight percent unsaturated diamines.

Claim 9

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

Claim 10

A process in accordance with claim 2 wherein said hydrogenation conditions comprise a weight ratio of the total of nickel and ruthenium 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 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 250* C and a reaction time in the range of about 15 minutes to about 5 hours when conducted as a batch process and 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 when conducted as a continuous process; wherein said at least one unsaturated dinitrile compound constitutes at least 5 weight percent of the unsaturated dinitriles in said feedstock; wherein said at least one unsaturated dinitrile compound is converted primarily to a saturated diamine having the formula:

Claim 11

A process in accordance with claim 9 wherein said catalyst 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 12

A process in accordance with claim 10 wherein said diluent consists essentially of at least one of said tertiary alkanols and said saturated hydrocarbons.

Claim 13

A process in accordance with claim 10 wherein each of said alkylene radical, said alkylidene radical and said alkyl radical has from 1 to 6 carbon atoms; and wherein said diluent consists essentially of at least one of said tertiary alkanols.

Claim 14

A process in accordance with claim 10 wherein each of said alkylene radical, said alkylidene radical and said alkyl radical has from 1 to 6 carbon atoms; and whereiin said diluent consists essentially of at least one of said saturated hydrocarbons.

Claim 15

A process in accordance with claim 9 wherein said catalyst 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, and wherein the contacting step is carried out at a temperature in the range of about 100* to about 200* C.

Claim 16

A process in accordance with claim 13 wherein each of said alkylene radical, said alkylidene radical and said alkyl radical has from 1 to 6 carbon atoms; and wherein said diluent consists essentially of at least one of said ethers.

Claim 17

A process in accordance with claim 9 wherein said feedstock comprises 5-methylenenonanedinitrile and 5-methyl-4-nonenedinitrile.