EP1322586A2 - Verfahren zur herstellung von benzylaceton - Google Patents
Verfahren zur herstellung von benzylacetonInfo
- Publication number
- EP1322586A2 EP1322586A2 EP01980276A EP01980276A EP1322586A2 EP 1322586 A2 EP1322586 A2 EP 1322586A2 EP 01980276 A EP01980276 A EP 01980276A EP 01980276 A EP01980276 A EP 01980276A EP 1322586 A2 EP1322586 A2 EP 1322586A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- catalyst
- palladium
- benzylacetone
- hydrogenation
- activated carbon
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
Definitions
- Benzylacetone is a valuable fragrance and aroma substance that is found in cocoa beans. Its smell is similar to that of jasmine and strawberry. Benzylacetone is used in fragrance compositions and flavors (Malasiewicz, Perfumery and Cosmetics, p. 211, 4/88, K. Bauer, A. Garbe, Common Fragrance and Flavor Materials, p. 73, VCH, Weinheim, 1985).
- nickel catalysts for hydrogenation with hydrogen, for example, nickel catalysts (Chem. Pharm. Bull., 1990, 38 (6), 1720), in particular Raney nickel (Ber. Dtsch. Chem. Ges. 56, 2174 (1923)) are used.
- PL 153267 describes an activated nickel catalyst on aluminum oxide, which can be used to produce benzylacetone in 82% yield from benzylidene acetone at 100-150 ° C.
- Precious metal catalysts such as platinum black are also known for the production of benzylacetone (Ann. Chim. 9, (1), 90, (1914)). It is also known to produce benzylacetone with a catalyst made of palladium on activated carbon in a solution of acetic acid-ammonium formate with a yield of 78% (Synth. Commun. (1998), 28 (22), 4193).
- a process for the preparation of benzylacetone by hydrogenation of benzylidene acetone has been found, which is characterized in that the hydrogenation is carried out in the presence of a palladium catalyst on activated carbon and / or a palladium catalyst on aluminum oxide.
- the process according to the invention is preferably carried out without a solvent. With the aid of the process according to the invention, benzylacetone can be produced economically in high yields.
- the handling of palladium as a catalyst is particularly advantageous since the catalyst is not a hazardous substance.
- the palladium catalyst can be used in the dry or moist (residual moisture in water) state for the process according to the invention.
- the proportion of palladium on the carrier material activated carbon or aluminum oxide can be 1 to 50% by weight, preferably 5 to
- the weight ratio of the catalyst used to benzylidene acetone is preferably 0.00001 to 0.01, in particular preferably 0.0001 to 0.001 to 1.
- the reaction temperature for the process according to the invention is preferably 20 to 100 ° C, particularly preferably 50-80 ° C.
- the hydrogen pressure is preferably 1 to 20 bar, particularly preferably 1 to 5 bar.
- the reaction time is preferably 1 to 20 hours, particularly preferably 6 to 15 hours.
- the method according to the invention can be carried out as follows:
- Benzylidene acetone and, for example, palladium on activated carbon 5% by weight are placed in a reaction vessel with a gassing stirrer. Hydrogenation is carried out at a hydrogen pressure of, for example, 1 bar. The crude product is filtered and distilled. It is surprising that the hydrogenation can be carried out in a high yield and selectively in the presence of a palladium catalyst on activated carbon and / or a palladium catalyst on aluminum oxide.
- Reaction product with the following composition 98.7% benzylacetone, 0.7% phenylbutanol.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10044400A DE10044400A1 (de) | 2000-09-08 | 2000-09-08 | Verfahren zur Herstellung von Benzylaceton |
| DE10044400 | 2000-09-08 | ||
| PCT/EP2001/009838 WO2002020450A2 (de) | 2000-09-08 | 2001-08-27 | Verfahren zur herstellung von benzylaceton |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1322586A2 true EP1322586A2 (de) | 2003-07-02 |
Family
ID=7655482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP01980276A Withdrawn EP1322586A2 (de) | 2000-09-08 | 2001-08-27 | Verfahren zur herstellung von benzylaceton |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6441242B1 (es) |
| EP (1) | EP1322586A2 (es) |
| AU (1) | AU2002212161A1 (es) |
| DE (1) | DE10044400A1 (es) |
| MX (1) | MXPA03001923A (es) |
| WO (1) | WO2002020450A2 (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2598537B1 (en) * | 2010-07-28 | 2017-05-03 | ARLANXEO Deutschland GmbH | Hydrogenation of diene-based polymers |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3860657A (en) | 1970-03-25 | 1975-01-14 | Givaudan Corp | Process for the preparation of citronellal |
| IT1085879B (it) | 1976-04-08 | 1985-05-28 | Basf Ag | Processo per la preparazione di chetoni superiori |
| DE3006867C2 (de) * | 1980-02-23 | 1981-11-12 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von höheren gesättigten Ketonen |
| DE3151086A1 (de) * | 1981-06-02 | 1982-12-16 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur kontinuierlichen herstellung von n-butyraldehyd durch selektive hydrierung von crotonaldehyd in fluessiger phase in gegenwart eines palladium-aluminiumoxid-katalysators |
| US4450300A (en) | 1981-12-23 | 1984-05-22 | Chemische Werke Huels Aktiengesellschaft | Process for the continuous manufacture of n-butyraldehyde by selective hydrogenation of crotonaldehyde in the liquid phase in the presence of a palladium-aluminum oxide catalyst |
| PL153267B1 (pl) * | 1987-12-04 | 1991-03-29 | Inst Chemii Przemyslowej | Ciągły sposób wytwarzania benzyloacetonu do celów perfumeryjnych |
| DE19814879A1 (de) | 1998-04-02 | 1999-10-07 | Basf Ag | Verfahren zur selektiven Flüssigphasenhydrierung von alpha,beta-ungesättigten Carbonylverbindungen |
-
2000
- 2000-09-08 DE DE10044400A patent/DE10044400A1/de not_active Ceased
-
2001
- 2001-08-27 EP EP01980276A patent/EP1322586A2/de not_active Withdrawn
- 2001-08-27 AU AU2002212161A patent/AU2002212161A1/en not_active Abandoned
- 2001-08-27 MX MXPA03001923A patent/MXPA03001923A/es unknown
- 2001-08-27 WO PCT/EP2001/009838 patent/WO2002020450A2/de not_active Application Discontinuation
- 2001-09-05 US US09/948,026 patent/US6441242B1/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| See references of WO0220450A2 * |
Also Published As
| Publication number | Publication date |
|---|---|
| US6441242B1 (en) | 2002-08-27 |
| WO2002020450A3 (de) | 2002-05-23 |
| US20020055656A1 (en) | 2002-05-09 |
| WO2002020450A2 (de) | 2002-03-14 |
| AU2002212161A1 (en) | 2002-03-22 |
| MXPA03001923A (es) | 2004-09-10 |
| DE10044400A1 (de) | 2002-04-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0071787B1 (de) | Neue Ruthenium/Kohle-Hydrierkatalysatoren, deren Herstellung und Verwendung zur selektiven Hydrierung von ungesättigten Carbonylverbindungen | |
| DE1618528B1 (de) | Neue Alfa-Methylen-aldehyde | |
| EP0008741B1 (de) | Verfahren zur Herstellung von Carbonylverbindungen | |
| EP0024651B1 (de) | Verfahren zur Herstellung von olefinisch ungesättigten Carbonylverbindungen und Alkoholen | |
| WO2011067386A2 (de) | Verfahren zur herstellung von aliphatischen aldehyden | |
| EP1322586A2 (de) | Verfahren zur herstellung von benzylaceton | |
| DE68922130T2 (de) | Verwendung von 2-Methoxy-4-Propyl-1-Cyclohexanol als Duftstoff. | |
| EP0402743B1 (de) | Verfahren zur Herstellung von Di-(p-glycidoxicyclohexyl)-methan | |
| DE60114210T2 (de) | Verfahren zur umsetzung von cyclododecan-1,2 dion in cyclododecanon | |
| WO2002048080A2 (de) | Verfahren zur herstellung von 1-(2,2,6-trimethylcyclohexyl)-3-alkanolen | |
| EP1345875B1 (de) | Verfahren zur herstellung von cis-2-tertiär butylcyclohexanol durch katalytische hydrierung von 2-tertiär-butylphenol | |
| DD243021A1 (de) | Verfahren zur regioselektiven hydrierung von cycloalkenylvinylaldehyden | |
| EP1282608B1 (de) | Herstellung von 2-ethyl-3-methyl-1,4-diazin | |
| DE2661006C2 (es) | ||
| DE19613332A1 (de) | Verfahren zur Herstellung eines Gemisches von Aminomethylcyclohexanen und Diamino-methyl-cyclohexanen | |
| DE862016C (de) | Verfahren zur Herstellung von Tetrahydropyranderivaten | |
| DE102015000321A1 (de) | Verfahren zur Herstellung von 1,4-Butandiol durch Metathese von Allylalkohol | |
| EP1332140A1 (de) | Verfahren zur herstellung von mintlacton | |
| DE1643331C3 (de) | Verfahren zur Herstellung von 3-Isopropyl-bzw. 3,5-Diisopropyl-4-aminophenyl-dimethyl-ca rbinol | |
| DE851191C (de) | Verfahren zur Herstellung von hoehermolekularen Hydroxyl- und bzw. oder Carbonylgruppen enthaltenden Kondensationsprodukten aus Alkoholen und Ketonen | |
| DE1518281A1 (de) | Verfahren zur Herstellung von Riechstoffen vom Ambratyp | |
| DE1618528C (de) | Neue alpha Methylen aldehyde | |
| DD148769A5 (de) | Verfahren zur herstellung von 5-amino-1,2,3,4-tetrahydroanthrachinon | |
| DE2601144A1 (de) | 2,3-disubstituierte 1-methyl-1- cyclopenten-derivate | |
| EP1315711A1 (de) | Verfahren zur herstellung von dihydrocumarin durch hydrierung von cumarin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| 17P | Request for examination filed |
Effective date: 20030408 |
|
| AK | Designated contracting states |
Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR |
|
| AX | Request for extension of the european patent |
Extension state: AL LT LV MK RO SI |
|
| RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: SYMRISE GMBH & CO. KG |
|
| RBV | Designated contracting states (corrected) |
Designated state(s): CH DE ES FR GB LI NL |
|
| 17Q | First examination report despatched |
Effective date: 20040728 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
| 18D | Application deemed to be withdrawn |
Effective date: 20041208 |