US4766249A
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Method of catalytically hydrolyzing alpha, beta-unsaturated carbonyl compounds
Assignee: Givaudan Flavors Corp
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Filing: 1986-12-24
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Granted: 1988-08-23
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Expires: 2006-12-24
Abstract
Abstract Alpha, beta-unsaturated carbonyl compounds are hydrolyzed under alkaline conditions in the presence of water to produce additional carbonyl-containing compounds. High yields are obtained when the alkaline catalyst contains hydroxide ion and the pH is maintained in the range of about 11 to about 13.
Inventors
- 👤 Keith T. Buck
- 👤 Anthony J. Boeing
- 👤 Joseph E. Dolfini
- 👤 Jerome Glinka
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 10:42
CPC Classifications
C; C07; C07C; C07C47/00; C07C47/52; C07C47/54; C07C45/00; C07C45/78; C07C45/81; C07C45/82; C07C45/27; C07C45/28; C07C45/51; C07C45/54; C07C45/61; C07C45/67; C07C45/673
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
126 words
A method of producing a carbonyl-containing compound which comprises hydrolyzing by dispersing in water an alpha, beta-unsaturated carbonyl compound of the formula ##STR3## to produce a carbonyl-containing compound and by-product according to the following formulas ##STR4## wherein R' and R" are hydrogen, aliphatic or aromatic hydrocarbon groups or substituted derivatives thereof, and R"' is an aliphatic or aromatic aldehyde- or ketone-containing group having the carbon to oxygen double bond of said aldehyde or ketone conjugated with the alpha, beta double bond between C and R"' of alpha, beta-unsaturated alpha,beta-unsaturated carbonyl compound, and conducting said hydrolysis of the alpha, beta-unsaturated carbonyl compound under the action of heat in the presence of a catalytic amount of hydroxide ion and at a pH of about 11 to about 13.
Claim 2
Independent Claim
126 words
A method of producing a carbonyl-containing compound which comprises hydrolyzing by dispersing in water an alpha, beta-unsaturated carbonyl compound of the formula ##STR3## to produce a carbonyl-containing compound and by-product according to the following formulas ##STR4## wherein R' and R" are hydrogen, aliphatic or aromatic hydrocarbon groups or substituted derivatives thereof, and R"' is an aliphatic or aromatic aldehyde- or ketone-containing group having the carbon to oxygen double bond of said aldehyde or ketone conjugated with the alpha, beta double bond between C and R"' of alpha, beta-unsaturated alpha,beta-unsaturated carbonyl compound, and conducting said hydrolysis of the alpha, beta-unsaturated carbonyl compound under the action of heat in the presence of a catalytic amount of hydroxide ion and at a pH of about 11 to about 13.
Claim 3
Dependent Claim
20 words
The method of claim 1 which is conducted at a pH in the range of about 12 to about 12.5.
Claim 4
Dependent Claim
24 words
The method of claim 1 wherein the individual carbonyl-containing compounds obtained from said hydrolysis reaction are fractionally distilled for separation in substantially pure form.
Claim 5
Dependent Claim
15 words
The method of claim 1 conducted in the presence of an anionic or non-ionic surfactant.
Claim 6
Dependent Claim
22 words
The method of claim 1 conducted under shearing agitation to facilitate the dispersion of the alpha, beta-unsaturated carbonyl compound in the water.
Claim 7
Dependent Claim
22 words
The method of claim 1 wherein said alpha, beta-unsaturated carbonyl compound is citral and the carbonyl-containing compounds produced are 6-methyl-5-hepten-2-one and acetaldehyde.
Claim 8
Dependent Claim
22 words
The method of claim 1 wherein said alpha, beta-unsaturated carbonyl compound is pulegone and the carbonyl-containing compounds produced are acetone and 3-methylcyclohexanone.
Claim 9
Independent Claim
136 words
A method of producing a carbonyl-containing compound which comprises hydrolyzing by dispersing in water under shearing agitation in the presence of an anionic surfactant an alpha, beta-unsaturated carbonyl compound of the formula ##STR5## to produce a carbonyl-containing compound and by-product according to the following formulas ##STR6## wherein R' and R" are hydrogen, aliphatic or aromatic hydrocarbon groups or substituted derivatives thereof, and R"' is an aliphatic or aromatic aldehyde- or ketone-containing group having the carbon to oxygen double bond of said aldehyde or ketone conjugated with the alpha, beta double bond between C and R"' of said alpha, beta-unsaturated carbonyl compound, and conducting said hydrolysis of the alpha, beta-unsaturated carbonyl compound under the action of heat in the presence of a catalytic amount of hydroxide ion and at a pH of about 12 to about 12.5.
Claim 10
Independent Claim
136 words
A method of producing a carbonyl-containing compound which comprises hydrolyzing by dispersing in water under shearing agitation in the presence of an anionic surfactant an alpha, beta-unsaturated carbonyl compound of the formula ##STR5## to produce a carbonyl-containing compound and by-product according to the following formulas ##STR6## wherein R' and R" are hydrogen, aliphatic or aromatic hydrocarbon groups or substituted derivatives thereof, and R"' is an aliphatic or aromatic aldehyde- or ketone-containing group having the carbon to oxygen double bond of said aldehyde or ketone conjugated with the alpha, beta double bond between C and R"' of said alpha, beta-unsaturated carbonyl compound, and conducting said hydrolysis of the alpha, beta-unsaturated carbonyl compound under the action of heat in the presence of a catalytic amount of hydroxide ion and at a pH of about 12 to about 12.5.
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) | 1991-08-23 | 1992-02-22 | 1992-08-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-08-23 | 1996-02-22 | 1996-08-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-08-23 | 2000-02-22 | 2000-08-23 | $7700.00 | Window Closed / Lapsed |