Patent US6233222B1 successfully refreshed from Google Patents.
US4226809A
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Hydrogenation of unsaturated dinitriles using catalyst comprising reaction products of nickel compound and of a palladium compound each with an alkali metal borohydride
Assignee: Phillips Petroleum Co
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Filing: 1979-08-07
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Granted: 1980-10-07
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Expires: 1999-08-07
Abstract
Abstract A branched chain unsaturated aliphatic dinitrile, e.g., as contained in a reaction product of acrylonitrile with isobutylene is subjected to hydrogenation under hydrogenation conditions in the presence of a combination or composition of catalysts including essentially at least one component selected from the group consisting of reaction products of an alkali metal borohydride with a palladium compound which is reducible by hydrogen to the elemental form and another component selected from a group consisting of the reaction products of an alkali metal borohydride with a nickel compound which is reducible by hydrogen to the elemental form, the individual components being primarily active as follows: the nickel component to hydrogenate nitrile groups and the palladium component to hydrogenate the olefinic unsaturation in the particular compounds hydrogenated; the process being carried out as a one-step process when the components are in admixture and as a two-step process when the components are used separately, one of them in one step and the other in another step of a two-step process. Completely saturated branched aliphatic diamines are produced.
Inventors
- 👤 Tod K. Shioyama
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 23:46
CPC Classifications
C; C07; C07C; C07C209/00; C07C209/44; C07C209/48; B; B01; B01J; B01J23/00; B01J23/38; B01J23/40; B01J23/44; B01J23/70; B01J23/89; B01J23/892
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
71 words
A process for the catalytic hydrogenation of a branched, unsaturated aliphatic dinitrile which comprises subjecting the same under hydrogenation conditions to the presence of a catalytic material comprising a reaction product of an alkali metal borohydride with a palladium compound which is reducible by hydrogenation to the elemental form and a reaction product of an alkali metal borohydride with a nickel compound which is reducible by hydrogen to the elemental form.
Claim 2
Dependent Claim
71 words
A process for the catalytic hydrogenation of a branched, unsaturated aliphatic dinitrile which comprises subjecting the same under hydrogenation conditions to the presence of a catalytic material comprising a reaction product of an alkali metal borohydride with a palladium compound which is reducible by hydrogenation to the elemental form and a reaction product of an alkali metal borohydride with a nickel compound which is reducible by hydrogen to the elemental form.
Claim 3
Dependent Claim
20 words
A process according to claim 1 wherein the several components of catalytic material are in an admixture during a hydrogenation.
Claim 4
Dependent Claim
43 words
A process according to claim 1 wherein each of the catalytic components is separately used during a two-step hydrogenation process in which the compound or compounds to be hydrogenated are placed under hydrogenation conditions in the presence of each of the components sequentially.
Claim 5
Dependent Claim
40 words
A process according to claim 1 wherein the branched chain unsaturated aliphatic dinitrile is represented by the formula ##STR6## wherein each R is independently selected from an alkylene radical and an alkylidene radical and wherein R' is an alkyl radical.
Claim 6
Dependent Claim
35 words
A process according to claim 4 wherein R contains a number of carbon atoms in the range 1-15 and wherein the compound contains carbon atoms in the range 7-30 and R' has 1-6 carbon atoms.
Claim 7
Dependent Claim
19 words
A process according to claim 5 wherein the compound contains a number of carbon atoms in the range 8-16.
Claim 8
Dependent Claim
19 words
A process according to claim 5 wherein the compound contains a number of carbon atoms in the range 9-12.
Claim 9
Dependent Claim
39 words
A process according to claim 1 wherein the branched chain unsaturated aliphatic dinitrile is selected from the following: 4-methyl-3-hexenedinitrile, 4-ethyl-3-hexenedinitrile, 5-methyl-4-nonenedinitrile, 5-ethyl-4-decenedinitrile, 7-methyl-6-tridecenedinitrile, 7-methyl-6-pentadecenedinitrile, 12-methyl-12-tetracosenedinitrile, 10-hexyl-9-tetracosenedinitrile, 2,3-dimethyl-3-hexenedinitrile, 2,4,6-trimethyl-3-heptenedinitrile, 4-ethyl-6,7-dimethyl-3-octenedinitrile, 2,4,6-triethyl-3-octenedinitrile, 2-ethyl-4,6-dipropyl-3-octenedinitrile, 2-methyl-4,6,8,10-tetrapropyl-3-dodecenedinitrile, 2,4,7,9,11,13,15-heptaethyl-6-hexadecenedinitrile, and the like and mixtures thereof.
Claim 10
Dependent Claim
70 words
A process according to claim 4 where in addition to the unsaturated dinitriles, there is present at least one unsaturated dinitrile having the formula ##STR7## wherein each R" is independently selected from the following: an alkylene radical and an alkylidene radical, wherein each R" will have a number of carbon atoms in the range 1-15 and wherein the compound will contain a number of carbon atoms in the range 6-30.
Claim 11
Dependent Claim
32 words
A process according to claim 1 wherein the palladium component of the catalyst is produced employing an oxide, halide, nitrate, sulfate, oxalate, acetate, carbamate, propionate, tartrate, hydroxide of palladium and mixtures thereof.
Claim 12
Dependent Claim
32 words
A process according to claim 1 wherein the nickel component of the catalyst is produced employing an oxide, halide, nitrate, sulfate, oxalate, acetate, carbamate, propionate, tartrate, hydroxide of nickel, and mixtures thereof.
Claim 13
Dependent Claim
27 words
A process according to claim 1 wherein the alkali metal borohydride has the formula MBH 4 wherein M is selected from lithium, sodium, potassium, rubidium and cesium.
Claim 14
Dependent Claim
20 words
A process according to claim 1 wherein the alkali metal borohydride is at least one of sodium and potassium borohydrides.
Claim 15
Dependent Claim
19 words
A process according to claim 1 wherein the catalyst components are each of them separately prepared and then admixed.
Claim 16
Dependent Claim
40 words
A process according to claim 1 wherein the hydrogenation temperature is within approximate range of from about 50° C. to about 200° C. and the hydrogen pressure sufficient to hydrogenate both the olefinic unsaturation and the nitrile group is employed.
Claim 17
Dependent Claim
42 words
A process according to claim 1 wherein a reaction product of acrylonitrile, with isobutylene, essentially comprising a mixture of isomeric unsaturated dinitriles and including principally 5-methylenenonanedinitrile and 5-methyl-4-nonenedinitrile and relatively very small amounts of more highly branched isomers is subjected to hydrogenation.
Claim 18
Dependent Claim
18 words
A process according to claim 1 wherein the reaction is performed in the presence of a suitable diluent.
Claim 19
Dependent Claim
16 words
A process according to claim 17 wherein the diluent is a mixture of water and t-butanol.
Claim 20
Dependent Claim
12 words
A process according to claim 1 wherein an amines-formation suppressant is present.
Claim 21
Dependent Claim
11 words
A process according to claim 19 wherein the suppressant is ammonia.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-10-07 | 1984-04-07 | 1984-10-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-07 | 1988-04-07 | 1988-10-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-07 | 1992-04-07 | 1992-10-07 | $7700.00 | Window Closed / Lapsed |