US3992452A
Expired / Lapsed
US
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Method for the production of alkoxycyclohexanones
Assignee: Unilever Bestfoods North America
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Filing: 1974-04-26
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Granted: 1976-11-16
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Expires: 1994-04-26
Abstract
Abstract Alkoxy phenols such as o-methoxyphenol (guaiacol) and o-ethoxyphenol are prepared from substituted cycloaliphatic ketones by dehydrogenation thereof in the presence of a Group VIII noble metal catalyst, preferably palladium supported on carbon, at a temperature of 150° to 250° C. The reaction is carried out neat or in the liquid phase using an alicyclic ester reaction solvent having a boiling point ranging from about 150° to 250° C. The substituted cycloaliphatic ketone reactant, such as 2-chlorocyclohexanone is prepared by chlorination of cyclohexanone with subsequent conversion of the 2-chlorocyclohexanone to the alkoxy-cyclohexanone compound which is dehydrogenated.
Inventors
- 👤 Allan B. McKague
- 👤 William DEWaal
- 👤 Carl E. Van Winckel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 21:16
CPC Classifications
C; C07; C07C; C07C41/00; C07C41/01; C07C41/18; C07C41/26
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
80 words
A process for the preparation of an alkoxycyclohexanone selected from the group consisting of 2-methoxy and 2-ethoxycyclohexanone in high yield, comprising: heating a reaction mass consisting essentially of 2-chlorocyclohexanone dissolved in an excess of a monohydric alkyl alcohol having 1 or 2 carbon atoms in a closed vessel to a temperature of from 110° to 200° C. to yield the corresponding alkoxycyclohexanone and hydrogen chloride, removing excess alcohol from the reaction mass, and recovering the alkoxycyclohexanone from the reaction mass.
Claim 2
Dependent Claim
80 words
A process for the preparation of an alkoxycyclohexanone selected from the group consisting of 2-methoxy and 2-ethoxycyclohexanone in high yield, comprising: heating a reaction mass consisting essentially of 2-chlorocyclohexanone dissolved in an excess of a monohydric alkyl alcohol having 1 or 2 carbon atoms in a closed vessel to a temperature of from 110° to 200° C. to yield the corresponding alkoxycyclohexanone and hydrogen chloride, removing excess alcohol from the reaction mass, and recovering the alkoxycyclohexanone from the reaction mass.
Claim 3
Dependent Claim
16 words
The process of claim 1 wherein 2-20 moles of alcohol are used per mole of 2-chlorocyclohexanone.
Claim 4
Dependent Claim
50 words
The process of claim 1 wherein the reaction mass includes a basic substance selected from the group consisting of tertiary amines, alkali and alkaline earth oxides having a pH ranging from 7-11, the basic substance reacting with the hydrogen chloride as it is formed to form the corresponding chloride salt.
Claim 5
Dependent Claim
14 words
The process of claim 3 wherein the basic substance is an organic tertiary amine.
Claim 6
Dependent Claim
16 words
The process of claim 3 wherein the basic substance is an alkali or alkaline earth carbonate.
Claim 7
Dependent Claim
14 words
The process of claim 3 wherein the basic substance is an alkaline earth oxide.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-11-16 | 1980-05-17 | 1980-11-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-11-16 | 1984-05-17 | 1984-11-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-11-16 | 1988-05-17 | 1988-11-16 | $7700.00 | Window Closed / Lapsed |