Patent US260874A successfully refreshed from Google Patents.
Patent US4079075A successfully refreshed from Google Patents.
US4079075A
Expired / Lapsed
US
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Primary alkyl esters as mediums for oxidations by phase-transfer catalyzed hypohalites
Assignee: Dow Chemical Co
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Filing: 1977-03-28
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Granted: 1978-03-14
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Expires: 1997-03-28
Abstract
Abstract The process of oxidizing organic compounds by dissolving the organic compound in a water-immiscible, inert organic solvent and contacting same with an aqueous hypohalite ion in the presence of a catalytic amount of a quaternary onium salt is improved by employing a primary alkyl ester as the organic solvent. For example, cyclohexylmethylamine is oxidized under mild conditions to a high yield of cyclohexylnitrile by dissolving the amine in ethyl acetate and contacting same with aqueous hypochlorite and in the presence of a catalytic amount of tetra-n-butylammonium chloride.
Inventors
- 👤 George A. Lee
- 👤 Harold H. Freedman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 11:00
CPC Classifications
C; C07; C07C; C07C255/00; C07C45/00; C07C45/27; C07C45/30
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
118 words
In the process of oxidizing an organic compound selected from the group consisting of amines, amides, aldehydes, primary and secondary alcohols, and organic compounds containing an activated carbon-carbon double bond with aqueous hypohalite ion, the process comprising contacting: (a) a water-immiscible, liquid organic phase comprising the organic compound and a water-immiscible, organic solvent; with (b) an aqueous phase containing hypohalite ion; and (c) a catalytic amount of a quaternary ammonium salt and/or a quaternary phosphonium salt, the improvement wherein: The water-immiscible, organic solvent is a primary alkyl ester of the formula: ##STR3## wherein R' is alkyl, aryl or an inertly-substituted alkyl or aryl radical and R" is alkyl or inertly-substituted alkyl from 1 to about 10 carbon atoms.
Claim 2
Dependent Claim
118 words
In the process of oxidizing an organic compound selected from the group consisting of amines, amides, aldehydes, primary and secondary alcohols, and organic compounds containing an activated carbon-carbon double bond with aqueous hypohalite ion, the process comprising contacting: (a) a water-immiscible, liquid organic phase comprising the organic compound and a water-immiscible, organic solvent; with (b) an aqueous phase containing hypohalite ion; and (c) a catalytic amount of a quaternary ammonium salt and/or a quaternary phosphonium salt, the improvement wherein: The water-immiscible, organic solvent is a primary alkyl ester of the formula: ##STR3## wherein R' is alkyl, aryl or an inertly-substituted alkyl or aryl radical and R" is alkyl or inertly-substituted alkyl from 1 to about 10 carbon atoms.
Claim 3
Dependent Claim
9 words
The process of claim 1 wherein R' is alkyl.
Claim 4
Dependent Claim
17 words
The process of claim 1 wherein R" is an alkyl of from 1 to 4 carbon atoms.
Claim 5
Dependent Claim
13 words
The process of claim 1 wherein the primary alkyl ester is ethyl acetate.
References Cited (Backward Citations)
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GB1227144A
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US3992432A
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GB1324763A
Cited
US3941827A
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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) | 1981-03-13 | 1981-09-12 | 1982-03-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-03-13 | 1985-09-12 | 1986-03-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-03-13 | 1989-09-12 | 1990-03-14 | $7700.00 | Window Closed / Lapsed |