US4281174A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Oxidative carbonylation of alcohols to produce dialkyl oxalates
Assignee: Chevron USA Inc
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Filing: 1980-04-21
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Granted: 1981-07-28
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Expires: 2000-04-21
Abstract
Abstract Preparation of dialkyl oxalates by the oxidative carbonylation of alcohols which comprises reacting a mixture of carbon monoxide and air with an alcohol in the presence of a catalytic amount of a catalyst comprising palladium in complex combination with a ligand, a small amount of a quinone, and a redox agent. Advantageously the reaction is carried out in the presence of a solvent.
Inventors
- 👤 Steven P. Current
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 15:34
CPC Classifications
C; C07; C07C; C07C67/00; C07C67/36
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
110 words
A process for preparing dialkyl oxalates by the oxidative carbonylation reaction which comprises contacting a normally liquid monohydric saturated aliphatic or alicyclic alcohol containing from 1 to 20 carbon atoms with a mixture of carbon monoxide and oxygen in the presence of a catalytic amount of a mixture comprising (1) palladium in complex combination with a neutral or negatively charged ligand, (2) a quinone, and (3) a redox agent comprising a compound of cobalt, manganese, copper, iron or vanadium, said contacting being conducted at a reaction temperature in the range of about 50° C.-100° C. and a carbon monoxide partial pressure in about the range 500 psi to 1500 psi.
Claim 2
Dependent Claim
110 words
A process for preparing dialkyl oxalates by the oxidative carbonylation reaction which comprises contacting a normally liquid monohydric saturated aliphatic or alicyclic alcohol containing from 1 to 20 carbon atoms with a mixture of carbon monoxide and oxygen in the presence of a catalytic amount of a mixture comprising (1) palladium in complex combination with a neutral or negatively charged ligand, (2) a quinone, and (3) a redox agent comprising a compound of cobalt, manganese, copper, iron or vanadium, said contacting being conducted at a reaction temperature in the range of about 50° C.-100° C. and a carbon monoxide partial pressure in about the range 500 psi to 1500 psi.
Claim 3
Dependent Claim
65 words
A process according to claim 1, wherein the palladium and quinone are present in molar ratios of palladium to quinone in about the range 0.1 to 1, the palladium and redox agent in molar ratios of palladium to redox agent metal in about the range 0.1 to 10, the oxygen being present in an amount of about 3-6% by volume of the carbon monoxide-oxygen mixture.
Claim 4
Dependent Claim
15 words
A process according to claim 1, wherein the alcohol contains 1 to 6 carbon atoms.
Claim 5
Dependent Claim
26 words
A process according to claim 1, wherein the reaction is carried out in the presence of a solvent inert to the components of the reaction system.
Claim 6
Dependent Claim
28 words
A process according to claim 4, wherein the palladium and solvent are present in an amount of about 0.001 to 1 weight percent palladium based on the two.
Claim 7
Dependent Claim
11 words
A process according to claim 5, wherein the solvent is acetonitrile.
Claim 8
Dependent Claim
14 words
A process according to claim 1, wherein the redox agent is a cobalt compound.
Claim 9
Dependent Claim
14 words
A process according to claim 7, wherein the cobalt redox agent is cobalt acetate.
Claim 10
Dependent Claim
85 words
A process according to claim 1, wherein the palladium and quinone are present in molar ratios of palladium to quinone in about the range 0.2 to 0.5, the palladium and redox agent in molar ratios of palladium metal to redox agent metal in the range 0.2 to 0.5, the reaction temperature is in the range 80°-90° C., the carbon monoxide partial pressure is in about the range 750-1250 psi, the oxygen being present in an amount of 3-6% volume percent of the carbon monoxide-oxygen mixture.
Claim 11
Dependent Claim
46 words
The process according to claim 9, wherein the reaction is carried out in the presence of a solvent inert to the components of the reaction mixture, the amount of palladium and solvent being present in an amount of about 0.1 weight percent based on the two.
Claim 12
Dependent Claim
20 words
A process according to claim 10, wherein the solvent is acetonitrile and the alcohol has 1 to 6 carbon atoms.
Claim 13
Dependent Claim
23 words
A process according to claim 1, wherein the palladium is in complex combination with a triorgano compound of phosphorus, arsenic, antimony or nitrogen.
Claim 14
Dependent Claim
24 words
A process according to claim 12, wherein the molar ratio of palladium metal to triorgano compound is in about the range 0.1 to 1.
Claim 15
Dependent Claim
88 words
A process according to claim 13, wherein the palladium and quinone are present in molar ratios of palladium to quinone in about the range 0.1 to 1, the palladium and redox agent in molar ratios of palladium to redox agent metal in about the range 0.1 to 10, the reaction temperature is in the range about 50° C.-100° C., the carbon monoxide partial pressure is about the range 500 psi to 1500 psi, the oxygen being present in an amount about 3-6% volume of the carbon monoxide-oxygen mixture.
Claim 16
Dependent Claim
14 words
Process according to claim 14, wherein the alcohol contains 1 to 6 carbon atoms.
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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) | 1984-07-27 | 1985-01-26 | 1985-07-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-07-27 | 1989-01-26 | 1989-07-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-07-27 | 1993-01-26 | 1993-07-28 | $7700.00 | Window Closed / Lapsed |