US4356318A
Expired / Lapsed
US
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Toluic acid
Assignee: EIDP Inc
•
Filing: 1980-12-15
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Granted: 1982-10-26
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Expires: 2000-12-15
Abstract
Abstract Process for oxidatively carbonylating toluene to toluic acid, at least 50 mol % of the toluic acid being the p-isomer, said process comprising contacting and reacting, at 110°-250° C., at a pressure of at least 500 psi (3.45 MPa), toluene, carbon monoxide, oxygen and the catalyst ingredients consisting essentially of (a) a compound of rhodium, iridium, ruthenium, platinum, palladium or osmium; (b) a sulfur oxy-acid or a Group Ia or IIa metal salt of a sulfur oxy-acid; and (c) an acid or acid mixture having a Hammett acidity value (-H o ) of greater than 7.0, said catalyst ingredients containing 0.5-30 mol % of (a) and 70-99.5 mol % of (b+c), with the molar ratios of (b/a) and (c/a) each being at least 2, and recovering toluic acid.
Inventors
- 👤 Francis J. Waller
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 07:33
CPC Classifications
B; B01; B01J; B01J31/00; B01J31/16; B01J31/165; B01J31/02; B01J31/06; B01J31/08; B01J31/10; C; C07; C07C; C07C51/00; C07C51/10
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
128 words
Process for oxidatively carbonylating toluene to toluic acid, at least 50 mol % of the toluic acid being the p-isomer, said process comprising contacting and reacting, at 110°-250° C., at a pressure of at least 500 psi (3.45 MPa), toluene, carbon monoxide, oxygen and the catalyst ingredients consisting essentially of (a) a compound of rhodium, iridium, ruthenium, platinum, palladium or osmium; (b) a sulfur oxy-acid or a Group Ia or IIa metal salt of a sulfur oxy-acid; and (c) an acid or acid mixture having a Hammett acidity value (--H o ) of greater than 7.0, said catalyst ingredients containing 0.5-30 mol % of (a) and 70-99.5 mol % of (b+c), with the molar ratios of (b/a) and (c/a) each being at least 2, and recovering toluic acid.
Claim 2
Dependent Claim
128 words
Process for oxidatively carbonylating toluene to toluic acid, at least 50 mol % of the toluic acid being the p-isomer, said process comprising contacting and reacting, at 110°-250° C., at a pressure of at least 500 psi (3.45 MPa), toluene, carbon monoxide, oxygen and the catalyst ingredients consisting essentially of (a) a compound of rhodium, iridium, ruthenium, platinum, palladium or osmium; (b) a sulfur oxy-acid or a Group Ia or IIa metal salt of a sulfur oxy-acid; and (c) an acid or acid mixture having a Hammett acidity value (--H o ) of greater than 7.0, said catalyst ingredients containing 0.5-30 mol % of (a) and 70-99.5 mol % of (b+c), with the molar ratios of (b/a) and (c/a) each being at least 2, and recovering toluic acid.
Claim 3
Dependent Claim
29 words
The process of claim 1 wherein at least 70 mol % of the toluic acid is p-isomer and catalyst ingredient (a) is a compound of rhodium, iridium, or ruthenium.
Claim 4
Dependent Claim
49 words
The process of claim 1 wherein at least 85 mol % of the toluic acid is p-isomer, catalyst ingredient (a) is a compound of rhodium or iridium, and catalyst ingredients (b) and (c) are the same and consist of a sulfur oxy-acid having an --H o greater than 7.0.
Claim 5
Dependent Claim
17 words
The process of claim 1 wherein the molar ratios (b/a) and (c/a) are each at least 3.
Claim 6
Dependent Claim
17 words
The process of claim 1 wherein the molar ratios (b/a) and (c/a) are each at least 4.
Claim 7
Dependent Claim
11 words
Process of claim 1 wherein the catalyst is a homogeneous catalyst.
Claim 8
Dependent Claim
13 words
Process of claim 6 wherein (b) and (c) are sulfuric acid or oleum.
Claim 9
Dependent Claim
11 words
Process of claim 6 wherein (b) and (c) are fluorosulfonic acid.
Claim 10
Dependent Claim
11 words
Process of claim 6 wherein (b) and (c) are trifluoromethanesulfonic acid.
Claim 11
Dependent Claim
11 words
Process of claim 6 wherein (b) and (c) are benzenesulfonic acid.
Claim 12
Dependent Claim
11 words
Process of claim 6 wherein (b) and (c) are perfluorooctanesulfonic acid.
Claim 13
Dependent Claim
11 words
Process of claim 6 wherein (b) and (c) are perfluoro-4-methyl-3,6-dioxaoctanesulfonic acid.
Claim 14
Dependent Claim
11 words
Process of claim 6 wherein (b) and (c) are p-toluenesulfonic acid.
Claim 15
Dependent Claim
27 words
Process of claim 6 wherein (b) is an α-fluorosulfonic acid and (c) is an acid or acid mixture having a Hammett acidity value of greater than 7.0.
Claim 16
Dependent Claim
19 words
Process of claim 6 wherein (b) is a Group Ia or IIa metal salt and (c) is hydrofluoric acid.
Claim 17
Dependent Claim
11 words
Process of claim 1 wherein the catalyst is a heterogeneous catalyst.
Claim 18
Dependent Claim
14 words
Process of claim 16 wherein (b) and (c) are a perfluorinated polymeric sulfonic acid.
Claim 19
Dependent Claim
9 words
Process of claim 1 wherein (a) is rhodium chloride.
Claim 20
Dependent Claim
9 words
Process of claim 1 wherein (a) is rhodium nitrate.
Claim 21
Dependent Claim
12 words
Process of claim 1 wherein (a) is Rh 6 (CO) 16 .
Claim 22
Dependent Claim
9 words
Process of claim 1 wherein (a) is iridium chloride.
Claim 23
Dependent Claim
9 words
Process of claim 1 wherein (a) is ruthenium chloride.
Claim 24
Dependent Claim
9 words
Process of claim 1 wherein (a) is platinum chloride.
Claim 25
Dependent Claim
9 words
Process of claim 1 wherein (a) is palladium nitrate.
Claim 26
Dependent Claim
10 words
Process of claim 1 wherein the temperature is 130°-200° C.
Claim 27
Dependent Claim
48 words
Catalytic process for oxidatively carbonylating toluene to toluic acid using the perfluorinated polymeric sulfonic acid having, based on the sulfonic acid grops, 50 to 98.5 mol % of hydrogen ions and 1.5 to 50 mol % of rhodium, iridium, ruthenium, platinum, palladium or osmium ions as a catalyst.
Claim 28
Dependent Claim
48 words
Catalytic process for oxidatively carbonylating toluene to toluic acid using the perfluorinated polymeric sulfonic acid having, based on the sulfonic acid grops, 50 to 98.5 mol % of hydrogen ions and 1.5 to 50 mol % of rhodium, iridium, ruthenium, platinum, palladium or osmium ions as a catalyst.
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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) | 1985-10-25 | 1986-04-26 | 1986-10-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-10-25 | 1990-04-26 | 1990-10-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-10-25 | 1994-04-26 | 1994-10-26 | $7700.00 | Window Closed / Lapsed |