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US4346240A
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Hydrogenation of esters using alkali doped heterogeneous group VIII transition metal catalysts
Assignee: Honeywell International Inc
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Filing: 1981-09-29
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Granted: 1982-08-24
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Expires: 2001-09-29
Abstract
Abstract A novel class of heterogeneous catalysts, containing Group VIII transition metals in combination with alkali organic compounds is prepared, such as potassium naphthalene on ruthenium on carbon. The catalysts are useful as heterogeneous catalysts in the hydrogenation of carboxylic acid esters. A process for producing the materials is described. The catalysts permit the process of the hydrogenation of carboxylic acid esters to primary alcohols to be conducted with the ester in the liquid phase at a temperature not exceeding about 150° C. with high selectivity. Catalysts of Group VIII transition metals and alkali metal on carbon are also useful in such processes.
Inventors
- 👤 Roger A. Grey
- 👤 Guido P. Pez
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 15:53
CPC Classifications
B; B01; B01J; B01J31/00; B01J31/02; B01J31/0201; B01J31/0204; B01J23/00; B01J23/38; B01J23/54; B01J23/56; B01J23/58; B01J31/0211; B01J31/0212; B01J31/12; B01J31/122; B01J31/26; B01J31/28; B01J31/30; C; C07; C07C; C07C29/00; C07C29/132; C07C29/136; C07C29/147; C07C29/149; B01J21/00; B01J21/18; B01J2231/00; B01J2231/60; B01J2231/64; B01J2231/641; B01J31/16; B01J31/1616; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/52
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
119 words
A process for hydrogenating a monoester to the alcohols corresponding to the acid and alcohol portions of the monoester which comprises reacting hydrogen with the monoester in the liquid phase in the presence of solid catalyst composition at a temperature not exceeding about 150° C., said solid catalyst composition consisting essentially of about 0.1 to about 15 weight percent of at least one group VIII transition metal, about 1 to about 50 weight percent of at least one alkali metal cation, about 2 to about 50 weight percent of an anion radical selected from the group consisting of arene radical anions, ketyls, aliphatic alkoxide anions and mixtures thereof, and the balance of a support comprising high surface area carbon.
Claim 2
Dependent Claim
119 words
A process for hydrogenating a monoester to the alcohols corresponding to the acid and alcohol portions of the monoester which comprises reacting hydrogen with the monoester in the liquid phase in the presence of solid catalyst composition at a temperature not exceeding about 150° C., said solid catalyst composition consisting essentially of about 0.1 to about 15 weight percent of at least one group VIII transition metal, about 1 to about 50 weight percent of at least one alkali metal cation, about 2 to about 50 weight percent of an anion radical selected from the group consisting of arene radical anions, ketyls, aliphatic alkoxide anions and mixtures thereof, and the balance of a support comprising high surface area carbon.
Claim 3
Dependent Claim
16 words
The process of claim 1 wherein the acid portion of the ester includes an aromatic ring.
Claim 4
Dependent Claim
18 words
The process of claim 1 or 14 or 15 wherein the acid portion of the ester is trifluoroacetyl.
Claim 5
Dependent Claim
11 words
The process of claim 3 wherein the ester is trifluoroethyl trifluoroacetate.
Claim 6
Dependent Claim
13 words
The process of claim 1 wherein the ester is in an inert solvent.
Claim 7
Dependent Claim
13 words
The process of claim 5 wherein the inert solvent is a polar ether.
Claim 8
Dependent Claim
11 words
The process of claim 6 wherein the inert solvent is tetrahydrofuran.
Claim 9
Dependent Claim
17 words
The process of claim 1 wherein the group VIII transition metal is ruthenium, rhodium, platinum or palladium.
Claim 10
Dependent Claim
35 words
The process of claim 1 wherein the radical anion is an arene radical anion selected from the group consisting of unsubstituted arene radical anions and arene radical anions substituted with alkyl, ether, dialkylamine or aryl.
Claim 11
Dependent Claim
16 words
The process of claim 9 wherein the arene radical anion is an unsubstituted arene radical anion.
Claim 12
Dependent Claim
15 words
The process of claim 9 wherein the arene radical anion is the naphthalene radical anion.
Claim 13
Dependent Claim
15 words
The process of claim 9 wherein the arene radical anion is the biphenyl radical anion.
Claim 14
Dependent Claim
25 words
The process of claim 9 wherein the arene radical anion is selected from the group consisting of the naphthalene, biphenyl, anthracene and phenanthrene radical anions.
Claim 15
Dependent Claim
15 words
The process of claim 1 wherein the radical anion is an aliphatic alkoxide radical anion.
Claim 16
Dependent Claim
23 words
The process of claim 14 wherein the aliphatic alkoxide anion has at most two carbons and is unsubstituted or substituted by fluorine only.
Claim 17
Dependent Claim
12 words
The process of claim 1 wherein the radical anion is a ketyl.
Claim 18
Dependent Claim
11 words
The process of claim 16 wherein the ketyl is diaryl ketyl.
Claim 19
Dependent Claim
11 words
The process of claim 16 wherein the ketyl is diphenyl ketyl.
Claim 20
Dependent Claim
32 words
The process of claim 1 wherein the alkali metal cation is about 2 to about 20 weight percent sodium or potassium cation or about 1 to about 5 weight percent lithium cation.
Claim 21
Dependent Claim
13 words
The process of claim 8 wherein the alkali metal cation is potassium cation.
Claim 22
Dependent Claim
87 words
A process for hydrogenating a monoester to the alcohols corresponding to the acid and alcohol portions of the monoester which comprises reacting hydrogen with the monoester in the liquid phase at a temperature not exceeding about 150° C. in the presence of a solid catalyst consisting essentially of about 0.1 to about 25 weight percent of at least one group VIII transition metal, about 0.5 to about 60 weight percent of at least one alkali metal and the balance an inert support comprising high surface area carbon.
Claim 23
Dependent Claim
87 words
A process for hydrogenating a monoester to the alcohols corresponding to the acid and alcohol portions of the monoester which comprises reacting hydrogen with the monoester in the liquid phase at a temperature not exceeding about 150° C. in the presence of a solid catalyst consisting essentially of about 0.1 to about 25 weight percent of at least one group VIII transition metal, about 0.5 to about 60 weight percent of at least one alkali metal and the balance an inert support comprising high surface area carbon.
Claim 24
Dependent Claim
17 words
The process of claim 21 wherein the group VIII transition metal is ruthenium, rhodium, platinum, or palladium.
Claim 25
Dependent Claim
13 words
The process of claim 22 wherein the group VIII transition metal is ruthenium.
Claim 26
Dependent Claim
13 words
The process of claim 22 wherein the group VIII transition metal is rhodium.
Claim 27
Dependent Claim
29 words
The process of claim 21 wherein the alkali metal is about 1 to about 5 weight percent lithium or about 2 to about 25 weight percent sodium or potassium.
Claim 28
Dependent Claim
11 words
The process of claim 25 wherein the alkali metal is potassium.
Claim 29
Dependent Claim
16 words
The process of claim 21 wherein the acid portion of the ester includes an aromatic ring.
Claim 30
Dependent Claim
14 words
The process of claim 21 wherein the acid portion of the ester is trifluoroacetyl.
Claim 31
Dependent Claim
11 words
The process of claim 28 wherein the ester is trifluoroethyl trifluoroacetate.
Claim 32
Dependent Claim
13 words
The process of claim 21 wherein the ester is in an inert solvent.
Claim 33
Dependent Claim
13 words
The process of claim 30 wherein the inert solvent is a polar ether.
Claim 34
Dependent Claim
11 words
The process of claim 31 wherein the inert solvent is tetrahydrofuran.
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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) | 1985-08-23 | 1986-02-22 | 1986-08-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-08-23 | 1990-02-22 | 1990-08-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-08-23 | 1994-02-22 | 1994-08-24 | $7700.00 | Window Closed / Lapsed |