US4051318A
Expired / Lapsed
US
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Process for preparing formate esters of alkyl-substituted aromatic hydroxy compounds
Assignee: Mitsubishi Gas Chemical Co Inc
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Filing: 1976-01-05
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Granted: 1977-09-27
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Expires: 1996-01-05
Abstract
Abstract Formate esters of the general formula HCOOAr wherein Ar is an aromatic hydrocarbon group containing an alkyl substituent are prepared by oxidizing alkyl aromatic aldehydes of the general formula ArCHO wherein Ar is the same as defined above with organic peroxy acids in the presence of hydrogen fluoride.
Inventors
- 👤 Takashi Suzuki
- 👤 Susumu Naito
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 04:04
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/50; C07C37/56; C07C67/00; C07C67/39
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
96 words
A process for preparing formate esters of the formula HCOOAr wherein Ar is an aromatic hydrocarbon group containing alkyl aromatic aldehyde of the general formula ArCHO wherein Ar is the same as defined above, with an organic peroxy acid in the presence of hydrogen fluoride in the presence or absence of a solvent under the conditions that (1) the molar ratio of the organic peroxy acid to the alkyl aromatic aldehyde is 1.0 to 1.5 : 1 and (2) the molar ratio of the hydrogen fluoride to all the oxygen-containing compounds is 0.5 to 4.0: 1.
Claim 2
Dependent Claim
96 words
A process for preparing formate esters of the formula HCOOAr wherein Ar is an aromatic hydrocarbon group containing alkyl aromatic aldehyde of the general formula ArCHO wherein Ar is the same as defined above, with an organic peroxy acid in the presence of hydrogen fluoride in the presence or absence of a solvent under the conditions that (1) the molar ratio of the organic peroxy acid to the alkyl aromatic aldehyde is 1.0 to 1.5 : 1 and (2) the molar ratio of the hydrogen fluoride to all the oxygen-containing compounds is 0.5 to 4.0: 1.
Claim 3
Dependent Claim
17 words
The process of claim 1 wherein the lower alkyl groups each contain 1 to 3 carbon atoms.
Claim 4
Dependent Claim
18 words
The process of claim 1 wherein the organic peroxy acid is p-peroxytoluic acid, peroxybenzoic acid or peroxyactic acid.
Claim 5
Dependent Claim
18 words
The process of claim 1 wherein the solvent is a lower aliphatic carboxylic acid, ester, ether or ketone.
Claim 6
Dependent Claim
35 words
The process of claim 1 wherein the oxidation reaction is carried out in a substantially anhydrous condition, and after the end of the oxidation the hydrogen fluoride is recovered singly or together with the solvent.
Claim 7
Dependent Claim
22 words
The process of claim 1 wherein the molar ratio of the hydrogen fluoride to the alkyl aromatic aldehyde is 3 to 20:1.
Claim 8
Dependent Claim
40 words
The process of claim 6 wherein a lower aliphat ic carboxylic acid, ester, ether or ketone is used in an amount such that the molar ratio of hydrogen fluoride to all the amount of oxygen-containing compounds becomes 0.5 to 4.0:1.
Claim 9
Dependent Claim
15 words
The process of claim 1 wherein the oxidation reaction temperature is -50° to +50° C.
Claim 10
Dependent Claim
16 words
The process of claim 1 wherein the oxidation reaction is carried out in the liquid phase.
Claim 11
Dependent Claim
18 words
The process of claim 1 wherein the organic peroxy acid is p-peroxytoluic acid obtained by autoxidation of p-tolualdehyde.
Claim 12
Dependent Claim
44 words
The process of claim 1 wherein Ar in the two formulae is an o-, m- or p-tolyl group, the organic peroxy acid is o-, m- or p-peroxytoluic acid, the solvent is acetone, and the oxidation reaction is carried out in a substantially anhydrous condition.
Claim 13
Dependent Claim
66 words
The process of claim 1 wherein Ar in the two formulae is an o-, m- or p-tolyl group, the organic peroxy acid is o-, m- or p-peroxytoluic acid, the solvent is acetone, and the oxidation is carried out in a substantially anhydrous condition while distilling off the acetone, and after the end of the oxidation reaction, a mixture of the hydrogen fluoride and acetone is recovered.
Claim 14
Dependent Claim
62 words
The process of claim 1 wherein Ar in the two formulae is a p-tolyl group, the organic peroxy acid is p-peroxytoluic acid obtained by autoxidation of p-tolualdehyde in acetone, the solvent is acetone, the molar ratio of the organic peroxy acid to the alkyl aromatic aldehyde is 1.0 to 1.3:1, and the oxidation reaction is carried out in a substantially anhydrous condition.
References Cited (Backward Citations)
JPS4925043A
Cited
US3976702A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-09-26 | 1981-03-28 | 1981-09-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-09-26 | 1985-03-28 | 1985-09-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-09-26 | 1989-03-28 | 1989-09-27 | $7700.00 | Window Closed / Lapsed |