US4005129A
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Process for the oxidative carbonylation of alcohols and method for the reoxidation of reduced copper salts produced by the oxidation carbonylation
Assignee: Atlantic Richfield Co
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Filing: 1975-06-04
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Granted: 1977-01-25
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Expires: 1995-06-04
Abstract
Abstract A process for the oxidative carbonylation of alcohols with carbon monoxide using metal salt catalysts, an amine base, amine salts, and copper (II) oxidizing salts to produce a predominate amount of oxalate ester and the reoxidation of the reduced copper (II) oxidizing salts with an oxygen-containing gas under mild conditions in the presence of the amine salt. After removal of water by physical or chemical means the oxidative carbonylation reaction can be repeated without any loss of yield of the oxalate ester.
Inventors
- 👤 Lee R. Zehner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 15:31
CPC Classifications
C; C07; C07C; C07C69/00; C07C69/34; C07C69/36; C07C67/00; C07C67/36
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
284 words
A cyclic process for the oxidative carbonylation of an alcohol having from 1 to 20 carbon atoms which comprises the steps of reacting under substantially anhydrous conditions, a saturated monohydric aliphatic or alicyclic alcohol which may contain other substituents which do not interfere with the reaction or an aromatic alcohol selected from the group consisting of benzyl, chlorobenzyl and methoxy-benzyl alcohols with carbon monoxide at a pressure of between about 1 to 700 atmospheres and at a temperature in the range of about 50° C. to 250° C. in the presence of an effective amount of a catalyst selected from the group consisting of palladium (II), rhodium (III), platinum (II) and copper (I) or (II) salt compounds, at least a stoichiometric amount of an aliphatic, cycloaliphatic, aromatic or heterocyclic amine or ammonia, a stoichiometric quantity of a copper (II) oxalate, sulfate, acetate, or trifluroacetate oxidant salt compound, and an excess over that normally formed in the carbonylation reaction of an ammonium or substituted ammonium sulfate, acetate or trifluroacetate salt compound, to produce the desired oxalate ester; separating the oxalate ester by distillation leaving a distillation residue comprised of catalyst, amine, reduced oxidant salt and ammonium salt compound; dissolving the distillation residue in alcohol and purging the resulting solution with oxygen or an oxygen-containing gas at pressures above 0.2 atmospheres and at a temperature in the range of from 20° C. to 200° C. to reoxidize the reduced copper oxidant salt and form co-product water; removing the reoxidation co-product water by the addition of water scavengers or azeotropic distillation leaving a residue comprised of catalyst, amine, copper (II) oxidant salt and ammonium salt compound; and recovering said residue for reuse in an oxidative carbonylation process.
Claim 2
Dependent Claim
284 words
A cyclic process for the oxidative carbonylation of an alcohol having from 1 to 20 carbon atoms which comprises the steps of reacting under substantially anhydrous conditions, a saturated monohydric aliphatic or alicyclic alcohol which may contain other substituents which do not interfere with the reaction or an aromatic alcohol selected from the group consisting of benzyl, chlorobenzyl and methoxy-benzyl alcohols with carbon monoxide at a pressure of between about 1 to 700 atmospheres and at a temperature in the range of about 50° C. to 250° C. in the presence of an effective amount of a catalyst selected from the group consisting of palladium (II), rhodium (III), platinum (II) and copper (I) or (II) salt compounds, at least a stoichiometric amount of an aliphatic, cycloaliphatic, aromatic or heterocyclic amine or ammonia, a stoichiometric quantity of a copper (II) oxalate, sulfate, acetate, or trifluroacetate oxidant salt compound, and an excess over that normally formed in the carbonylation reaction of an ammonium or substituted ammonium sulfate, acetate or trifluroacetate salt compound, to produce the desired oxalate ester; separating the oxalate ester by distillation leaving a distillation residue comprised of catalyst, amine, reduced oxidant salt and ammonium salt compound; dissolving the distillation residue in alcohol and purging the resulting solution with oxygen or an oxygen-containing gas at pressures above 0.2 atmospheres and at a temperature in the range of from 20° C. to 200° C. to reoxidize the reduced copper oxidant salt and form co-product water; removing the reoxidation co-product water by the addition of water scavengers or azeotropic distillation leaving a residue comprised of catalyst, amine, copper (II) oxidant salt and ammonium salt compound; and recovering said residue for reuse in an oxidative carbonylation process.
Claim 3
Dependent Claim
38 words
A process according to claim 1 wherein the catalyst is selected from the group consisting of palladium (II) chloride, palladium (II) iodide, copper (I) iodide, copper (II) chloride, rhodium (III) chloride, palladium (II) acetate and palladium (II) sulfate.
Claim 4
Dependent Claim
13 words
A process according to claim 2 wherein the catalyst is palladium (II) chloride.
Claim 5
Dependent Claim
13 words
A process according to claim 2 wherein the catalyst is palladium (II) iodide.
Claim 6
Dependent Claim
13 words
A process according to claim 2 wherein the catalyst is copper (I) iodide.
Claim 7
Dependent Claim
22 words
A process according to claim 1 wherein the amine is selected from the group consisting of triethylamine, ammonia, tri n-butylamine and diethylamine.
Claim 8
Dependent Claim
11 words
A process according to claim 6 wherein the amine is triethylamine.
Claim 9
Dependent Claim
16 words
A process according to claim 1 wherein the copper (II) oxidant salt is copper (II) sulfate.
Claim 10
Dependent Claim
16 words
A process according to claim 1 wherein the copper (II) oxidant salt is copper (II) oxalate.
Claim 11
Dependent Claim
42 words
A process according to claim 1 wherein the reaction is carried out in the presence of a co-catalytic amount of an organic mono- or poly-dentate ligand selected from the group consisting of alkyl, aryl and halogen substituted phosphines, arsines, stibines and iodides.
Claim 12
Dependent Claim
22 words
A process according to claim 10 wherein the ligand is selected from the group consisting of triethylphosphine, triphenylphosine, triphenylarsine and lithium iodide.
Claim 13
Dependent Claim
23 words
A process according to claim 1 wherein the alcohol is selected from the group consisting of ethyl alcohol, isopropyl alcohol and tert-butyl alcohol.
Claim 14
Dependent Claim
12 words
A process according to claim 12 wherein the alcohol is isopropyl alcohol.
Claim 15
Dependent Claim
30 words
A process according to claim 1 wherein the pressure is between about 100 and 200 atmospheres and the temperature is in the range of about 100° C. to 135° C.
Claim 16
Dependent Claim
30 words
A process according to claim 1 wherein the ammonium or substituted ammonium salt compound is selected from the group consisting of triethyl ammonium sulfate, ammonium sulfate and triethyl ammonium acetate.
Claim 17
Dependent Claim
14 words
A process according to claim 15 wherein the ammonium salt compound is triethylammonium sulfate.
Claim 18
Dependent Claim
36 words
A process according to claim 1 wherein the ammonium salt or substituted ammonium salt compounds are employed in molar concentrations or from about 0.25 to 2 moles of said salt based on stoichiometric amount of amine.
Claim 19
Dependent Claim
24 words
A process according to claim 1 wherein the ammonium salt or substituted ammonium salt is formed in situ upon the addition of an acid.
Claim 20
Dependent Claim
12 words
A process according to claim 18 wherein said acid is sulfuric acid.
Claim 21
Dependent Claim
12 words
A process according to claim 18 wherein the acid is acetic acid.
Claim 22
Dependent Claim
37 words
A process according to claim 1 wherein the alcohol is isopropyl alcohol, the catalyst is palladium (II) iodide, the amine is triethylamine, the oxidant salt is copper (II) sulfate and the substituted ammonium sait is triethylammonium sulfate.
Claim 23
Dependent Claim
37 words
A process according to claim 1 wherein the alcohol is isopropyl alcohol, the catalyst is copper (I) iodide, the amine is triethylamine, the oxidant salt is copper (II) sulfate and the substituted ammonium salt is triethylammonium sulfate.
References Cited (Backward Citations)
US3393136A
Cited
DE2213435A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-01-25 | 1980-07-26 | 1981-01-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-01-25 | 1984-07-26 | 1985-01-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-01-25 | 1988-07-26 | 1989-01-25 | $7700.00 | Window Closed / Lapsed |