US4260829A
Expired / Lapsed
US
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Preparation of carbonyl compounds
Assignee: BASF SE
•
Filing: 1979-08-17
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Granted: 1981-04-07
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Expires: 1999-08-17
Abstract
Abstract Carbonyl compounds R1-CHR2-CHR3-CR4O (I, R1=H or an organic radical; R2-R4=H or C1-C4-alkyl) are prepared by selective hydrogenation of the alpha , beta -unsaturated carbonyl compounds R1-CR2=CR3-CR4O (II) in the liquid phase by means of hydrogen in the presence of a palladium catalyst and of from 15 to 50% by weight, based on (II), of a tertiary amine.
Inventors
- 👤 Michael Horner
- 👤 Axel Nissen
- 👤 Peter R. Laurer
- 👤 Matthias Irgang
- 👤 Heinrich Pasedach
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 02:04
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/61; C07C45/62
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
143 words
In a process for the preparation of a carbonyl compound of the formula (I) ##STR4## where R 1 is alkyl or alkenyl of 1 to 20 carbon atoms and R 2 and R 3 are hydrogen or C 1 -C 4 -alkyl and R 4 is hydrogen, by the selective hydrogenation of the α,β-unsaturated carbonyl compound (II) ##STR5## with hydrogen in the presence of a palladium catalyst, an organic solvent and an organic base, in the liquid phase, the improvement which comprises: carrying out the hydrogenation in the presence of from 15 to 50% by weight, based on (II), of an aliphatic tertiary amine of 3 to 30 carbon atoms, wherein as solvent there is used between 25 and 150% by weight of (II) of methanol or ethanol and wherein the water concentration in the reaction mixture does not exceed 5% by weight.
Claim 2
Dependent Claim
143 words
In a process for the preparation of a carbonyl compound of the formula (I) ##STR4## where R 1 is alkyl or alkenyl of 1 to 20 carbon atoms and R 2 and R 3 are hydrogen or C 1 -C 4 -alkyl and R 4 is hydrogen, by the selective hydrogenation of the α,β-unsaturated carbonyl compound (II) ##STR5## with hydrogen in the presence of a palladium catalyst, an organic solvent and an organic base, in the liquid phase, the improvement which comprises: carrying out the hydrogenation in the presence of from 15 to 50% by weight, based on (II), of an aliphatic tertiary amine of 3 to 30 carbon atoms, wherein as solvent there is used between 25 and 150% by weight of (II) of methanol or ethanol and wherein the water concentration in the reaction mixture does not exceed 5% by weight.
Claim 3
Dependent Claim
67 words
The process of claim 1, wherein the catalyst used is a Pd/active charcoal supported catalyst which has a Pd content of from 0.1 to 50% by weight, a mean diameter of the Pd particles of from 8 to 50 Angstrom, a pore diameter distribution maximum at from 4 to 50 Angstrom, and a surface area, of the active charcoal, of from 600 to 1,000 m 2 /kg.
Claim 4
Dependent Claim
20 words
The process of claim 1 or 2, wherein trimethylamine is used as the tertiary amine and methanol is the solvent.
Claim 5
Dependent Claim
22 words
The process of claims 1 or 2, wherein citral is hydrogenated to citronellal and wherein trimethylamine is used as the tertiary amine.
References Cited (Backward Citations)
US3860657A
Cited
US3971830A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-04-06 | 1984-10-06 | 1985-04-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-04-06 | 1988-10-06 | 1989-04-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-04-06 | 1992-10-06 | 1993-04-07 | $7700.00 | Window Closed / Lapsed |