Patent US3880928A successfully refreshed from Google Patents.
US3880928A
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Catalytic hydrogenation of unsaturated dinitriles employing rhodium as catalytic agent
Assignee: Phillips Petroleum Co
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Filing: 1973-11-19
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Granted: 1975-04-29
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Expires: 1993-11-19
Abstract
Abstract The one-step catalytic hydrogenation of an unsaturated dinitrile reactant of the formula WHEREIN EACH R is an alkylene or an alkylidene radical, and each R'' is an alkyl radical, is carried out in the presence of NH3; hydrogen; a diluent selected from the group consisting of aliphatic alcohols having 2 to 12 carbon atoms, alkanes and cycloalkanes having from 4 to 12 carbon atoms, and unsubstituted acyclic and unsubstituted cyclic ethers having from 4 to 12 carbon atoms; and a catalyst selected from elemental rhodium, rhodium compounds which are reducible by hydrogen to elemental rhodium, and mixtures thereof.
Inventors
- 👤 Charles A Drake
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 20:04
CPC Classifications
C; C07; C07C; C07C209/00; C07C209/44; C07C209/48; B; B01; B01J; B01J23/00; B01J23/38; B01J23/40; B01J23/46; B01J23/464
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
21 words
A PROCESS FOR THE CATALYTIC HYDROGENERATION OF AN UNSATURATED DINITRILE FEEDSTOCK CONTAINING AT LEAST ONE UNSATURATED DINITRILE COMPOUND OF THE FORMULA:
Claim 2
Dependent Claim
21 words
A PROCESS FOR THE CATALYTIC HYDROGENERATION OF AN UNSATURATED DINITRILE FEEDSTOCK CONTAINING AT LEAST ONE UNSATURATED DINITRILE COMPOUND OF THE FORMULA:
Claim 3
Dependent Claim
142 words
A process in accordance with claim 1 wherein said suitable hydrogenation conditions comprise a weight ratio of rhodium 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 5,000 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 within the range of about 30*C to about 150*C, and a reaction time in the range of about 15 minutes to about 5 hours for a batch process and a liquid hourly space velocity in the range of about 0.1 to about 10 volumes of unsaturated dinitrile reactant plus diluent per volume of catalyst for a continuous process.
Claim 4
Dependent Claim
42 words
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 rhodium being in the range of about 0.5 to about 50 weight percent of said catalyst composition.
Claim 5
Dependent Claim
27 words
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
Dependent Claim
25 words
A process in accordance with claim 1 wherein said at least one unsaturated dinitrile compound comprises a mixture of 5-methyl-b 4-nonenedinitrile, 2,4dimethyl-4-octenedinitrile, 2,4-dimethyl-3-octenedinitrile, and 2,4,6-trimethyl-3-heptenedinitrile.
Claim 7
Dependent Claim
22 words
A process in accordance with claim 1 further comprising recovering a diamine product containing less than about 1 weight percent unsaturated diamines.
Claim 8
Dependent Claim
17 words
A process in accordance with claim 1 further comprising recovering a diamine product essentially free of unsaturation.
Claim 9
Dependent Claim
21 words
A process in accordance with claim 1, wherein said feedstock further comprises at least one unsaturated dinitrile reactant of the formula:
Claim 10
Dependent Claim
133 words
A process in accordance with claim 8 wherein said suitable hydrogenation conditions comprise a weight ratio of rhodium 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, and a temperature in the range of about 70*C. to about 120*C; 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 unsaturated dinitrile compound is converted primarily to a saturated diamine having the formula:
Claim 11
Dependent Claim
17 words
A process in accordance with claim 9 wherein the recovered diamine product is essentially free of unsaturation.
Claim 12
Dependent Claim
30 words
A process in accordance with claim 9 wherein each R and R'' has from 1 to 6 carbon atoms, and wherein each R'''' has from 1 to 7 carbon atoms.
Claim 13
Dependent Claim
18 words
A process in accordance with claim 9 wheRein said diluent is at least one of said unsubstituted alkanols.
Claim 14
Dependent Claim
19 words
A process in accordance with claim 9 wherein said diluent is at least one of said alkanes and cycloalkanes.
Claim 15
Dependent Claim
17 words
A process in accordance with claim 9 wherein said diluent is at least one of said ethers.
Claim 16
Dependent Claim
14 words
A process in accordance with claim 9 wherein said feedstock comprises 5-methylene-nonanedinitrile and 5-methyl-4-nonenedinitrile.
References Cited (Backward Citations)
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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) | 1978-04-28 | 1978-10-28 | 1979-04-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-04-28 | 1982-10-28 | 1983-04-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-04-28 | 1986-10-28 | 1987-04-29 | $7700.00 | Window Closed / Lapsed |