US4347387A
Expired / Lapsed
US
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Process for preparing hydroxycitronellal
Assignee: Takasago International Corp
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Filing: 1980-12-04
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Granted: 1982-08-31
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Expires: 2000-12-04
Abstract
Abstract A process as described for preparing hydroxycitronellal by isomerizing certain 7-hydroxygeranylamine compound or 7-hydroxynerylamine compounds using a catalyst comprising a divalent palladium compound and a phosphine compound.
Inventors
- 👤 Susumu Akutagawa
- 👤 Takanao Taketomi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 09:40
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/56; C07C45/51; C07C45/516; C07C45/562
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
146 words
A process for preparing hydroxycitronellal comprising isomerizing a 7-hydroxygeranylamine compound (I) or a 7-hydroxynerylamine compound (II), represented by formulae (I) and (II), respectively, ##STR11## wherein R 1 and R 2 each represents an alkyl group containing from 1 to 6 carbon atoms or a cycloalkyl group, or R 1 and R 2 may jointly form together with the adjacent nitrogen atom a 5- or 6-membered ring that may contain other heterocyclic atoms selected from nitrogen and oxygen, using a catalytically effective amount of a catalyst composed of a divalent palladium compound and a phosphine compound at a temperature of from about 140° to 180° C. for about 5 to 20 hours, to thereby convert the amine compound to a 7-hydroxyaldehydoenamine represented by formula (III) ##STR12## wherein R 1 and R 2 are the same as defined above, and then hydrolyzing the enamine using a dilute acid.
Claim 2
Dependent Claim
146 words
A process for preparing hydroxycitronellal comprising isomerizing a 7-hydroxygeranylamine compound (I) or a 7-hydroxynerylamine compound (II), represented by formulae (I) and (II), respectively, ##STR11## wherein R 1 and R 2 each represents an alkyl group containing from 1 to 6 carbon atoms or a cycloalkyl group, or R 1 and R 2 may jointly form together with the adjacent nitrogen atom a 5- or 6-membered ring that may contain other heterocyclic atoms selected from nitrogen and oxygen, using a catalytically effective amount of a catalyst composed of a divalent palladium compound and a phosphine compound at a temperature of from about 140° to 180° C. for about 5 to 20 hours, to thereby convert the amine compound to a 7-hydroxyaldehydoenamine represented by formula (III) ##STR12## wherein R 1 and R 2 are the same as defined above, and then hydrolyzing the enamine using a dilute acid.
Claim 3
Dependent Claim
53 words
A process as in claim 1, wherein said catalyst composed of a divalent palladium compound and a phosphine compound is that obtained by reacting, in relative amounts, 1 mol of palladium compound, from 1 to 2 mols of a trivalent organophosphorous compound, and from 1 to 5 mols of an alkali metal phenoxide.
Claim 4
Dependent Claim
80 words
A process as in claim 2, wherein said trivalent organophosphorous compound is a compound represented by formula (IV) ##STR13## wherein A represents an alkyl group containing from 1 to 6 carbon atoms, a cycloalkyl group, or an aryl group, and B and C each represents an alkyl group containing from 1 to 6 carbon atoms, a cycloalkyl group, or an aryl group, or B and C may jointly form together with the adjacent phosphorus atom a 5- or 6-membered ring.
Claim 5
Dependent Claim
35 words
A process as in claim 2, wherein said trivalent organophosphorous compound is an alkylenediphosphine in which two phosphorus atoms are connected to each other through a carbon chain containing from 1 to 4 carbon atoms.
Claim 6
Dependent Claim
24 words
A process as in claim 2, wherein said trivalent organophosphorous compound is a diphosphine compound in which two phosphorus atoms form a heterocyclic ring.
Claim 7
Dependent Claim
27 words
A process as in claim 2, wherein said trivalent organophosphorous compound is 1,1'-bis-phosphinoferrocene in which two phosphorus atoms are connected to each other through a ferrocenyl group.
Claim 8
Dependent Claim
20 words
A process as in claim 2, wherein said alkali metal phenoxide is derived from unsubstituted, mono-substituted, di-substituted, or tri-substituted phenol.
Claim 9
Dependent Claim
35 words
A process as in claim 1, 2, 3, 4, 5, 6, or 7, wherein the molar ratio of the compound according to formula (I) or (II) to the palladium compound is from 1000/l to 5,000/l.
Claim 10
Dependent Claim
68 words
A process as in claim 2, 3, 4, 5, 6, or 7, wherein the catalyst is obtained by reacting the organophosphorous compound and the palladium compound in a molar ratio of from 1/l to 2/l, and, after dissolving in a solvent to prepare a homogeneous solution, adding thereto 1 to 5 moles of alkali metal phenoxide while cooling to a temperature of from 0° C. to 10° C.
Claim 11
Dependent Claim
18 words
A process as in claim 1, wherein said dilute acid is a mineral acid or an organic acid.
Claim 12
Dependent Claim
25 words
A process as in claim 10, wherein said mineral acid is hydrochloric acid, sulfuric acid or phosphoric acid and said organic acid is acetic acid.
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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) | 1985-08-30 | 1986-03-01 | 1986-08-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-08-30 | 1990-03-01 | 1990-08-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-08-30 | 1994-03-01 | 1994-08-31 | $7700.00 | Window Closed / Lapsed |