GB1390465A - Production of alpha,beta-unsaturated ketones - Google Patents
Production of alpha,beta-unsaturated ketonesInfo
- Publication number
- GB1390465A GB1390465A GB4709072A GB4709072A GB1390465A GB 1390465 A GB1390465 A GB 1390465A GB 4709072 A GB4709072 A GB 4709072A GB 4709072 A GB4709072 A GB 4709072A GB 1390465 A GB1390465 A GB 1390465A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- hydrocarbon radical
- dimethyl
- unsaturated
- hexen
- 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.)
- Expired
Links
- 150000002576 ketones Chemical class 0.000 title abstract 4
- -1 hydrocarbon radical Chemical class 0.000 abstract 5
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- 229930195733 hydrocarbon Natural products 0.000 abstract 3
- IYMKNYVCXUEFJE-SNAWJCMRSA-N (e)-5-methylhex-3-en-2-one Chemical compound CC(C)\C=C\C(C)=O IYMKNYVCXUEFJE-SNAWJCMRSA-N 0.000 abstract 2
- JNSOSJJMBWJCEH-UHFFFAOYSA-N E-7-methyl-4-octen-3-one Natural products CCC(=O)C=CCC(C)C JNSOSJJMBWJCEH-UHFFFAOYSA-N 0.000 abstract 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- LABTWGUMFABVFG-ONEGZZNKSA-N (3E)-pent-3-en-2-one Chemical compound C\C=C\C(C)=O LABTWGUMFABVFG-ONEGZZNKSA-N 0.000 abstract 1
- KSKXSFZGARKWOW-GQCTYLIASA-N (3e)-6-methylhepta-3,5-dien-2-one Chemical compound CC(C)=C\C=C\C(C)=O KSKXSFZGARKWOW-GQCTYLIASA-N 0.000 abstract 1
- SWGLACWOVFCDQS-VNKDHWASSA-N (3e,5e)-hepta-3,5-dien-2-one Chemical compound C\C=C\C=C\C(C)=O SWGLACWOVFCDQS-VNKDHWASSA-N 0.000 abstract 1
- WRRZKDVBPZBNJN-ONEGZZNKSA-N (e)-4-(4-methoxyphenyl)but-3-en-2-one Chemical compound COC1=CC=C(\C=C\C(C)=O)C=C1 WRRZKDVBPZBNJN-ONEGZZNKSA-N 0.000 abstract 1
- LPCWMYHBLXLJJQ-SNAWJCMRSA-N (e)-hex-3-en-2-one Chemical compound CC\C=C\C(C)=O LPCWMYHBLXLJJQ-SNAWJCMRSA-N 0.000 abstract 1
- GUJXYUWVBKJWIB-UHFFFAOYSA-N 1-(4-bicyclo[2.2.1]heptanyl)-5-methylhexa-2,4-dien-1-one Chemical compound C1CC2CCC1(C(=O)C=CC=C(C)C)C2 GUJXYUWVBKJWIB-UHFFFAOYSA-N 0.000 abstract 1
- COWHHKVRSZYCQT-UHFFFAOYSA-N 2,10,14-trimethylpentadeca-1,7,9,13-tetraen-6-one Chemical compound CC(C)=CCCC(C)=CC=CC(=O)CCCC(C)=C COWHHKVRSZYCQT-UHFFFAOYSA-N 0.000 abstract 1
- YNZHVYSRBNOQCI-UHFFFAOYSA-N 2,10-dimethylundeca-1,7,9-trien-6-one Chemical compound CC(C)=CC=CC(=O)CCCC(C)=C YNZHVYSRBNOQCI-UHFFFAOYSA-N 0.000 abstract 1
- SGSOYEXWICWDPN-UHFFFAOYSA-N 2,10-dimethylundeca-2,4,7,9-tetraen-6-one Chemical compound CC(C)=CC=CC(C=CC=C(C)C)=O SGSOYEXWICWDPN-UHFFFAOYSA-N 0.000 abstract 1
- LJPRVFPTWDWRJD-UHFFFAOYSA-N 2,8-dimethylnona-2,5,7-trien-4-one Chemical compound CC(C)=CC=CC(=O)C=C(C)C LJPRVFPTWDWRJD-UHFFFAOYSA-N 0.000 abstract 1
- LPCWMYHBLXLJJQ-UHFFFAOYSA-N 3-Hexen-2-on Natural products CCC=CC(C)=O LPCWMYHBLXLJJQ-UHFFFAOYSA-N 0.000 abstract 1
- KSMHKGWMLSIYNG-UHFFFAOYSA-N 5-methyl-1-phenylhexa-2,4-dien-1-one Chemical compound CC(C)=CC=CC(=O)C1=CC=CC=C1 KSMHKGWMLSIYNG-UHFFFAOYSA-N 0.000 abstract 1
- RSNMTAYSENLHOW-GQCTYLIASA-N 6-Methyl-3-hepten-2-one, trans- Chemical compound CC(C)C\C=C\C(C)=O RSNMTAYSENLHOW-GQCTYLIASA-N 0.000 abstract 1
- SPHLZZZXIWUZNM-UHFFFAOYSA-N 7,11-dimethyldodeca-4,6,10-trien-3-one Chemical compound CCC(=O)C=CC=C(C)CCC=C(C)C SPHLZZZXIWUZNM-UHFFFAOYSA-N 0.000 abstract 1
- CWUPRFQRNWZZJM-UHFFFAOYSA-N 7-methylocta-4,6-dien-3-one Chemical compound CCC(=O)C=CC=C(C)C CWUPRFQRNWZZJM-UHFFFAOYSA-N 0.000 abstract 1
- BWHOZHOGCMHOBV-UHFFFAOYSA-N Benzalacetone Natural products CC(=O)C=CC1=CC=CC=C1 BWHOZHOGCMHOBV-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclo-pentanone Natural products O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 abstract 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- HNZUNIKWNYHEJJ-UHFFFAOYSA-N geranyl acetone Natural products CC(C)=CCCC(C)=CCCC(C)=O HNZUNIKWNYHEJJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- KSKXSFZGARKWOW-UHFFFAOYSA-N methylheptadienone Natural products CC(C)=CC=CC(C)=O KSKXSFZGARKWOW-UHFFFAOYSA-N 0.000 abstract 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 abstract 1
- JXJIQCXXJGRKRJ-KOOBJXAQSA-N pseudoionone Chemical compound CC(C)=CCC\C(C)=C\C=C\C(C)=O JXJIQCXXJGRKRJ-KOOBJXAQSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 abstract 1
- 239000011787 zinc oxide Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/14—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms
- C07C403/16—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms not being part of —CHO groups
-
- 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
- C07C45/67—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 isomerisation; by change of size of the carbon skeleton
- C07C45/68—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712150992 DE2150992C3 (de) | 1971-10-13 | Verfahren zur Herstellung von a, ß-ungesättigten Ketonen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1390465A true GB1390465A (en) | 1975-04-16 |
Family
ID=5822222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4709072A Expired GB1390465A (en) | 1971-10-13 | 1972-10-12 | Production of alpha,beta-unsaturated ketones |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4005147A (cg-RX-API-DMAC7.html) |
| BE (1) | BE789849A (cg-RX-API-DMAC7.html) |
| CH (1) | CH603520A5 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2156246B1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1390465A (cg-RX-API-DMAC7.html) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4165339A (en) * | 1976-02-12 | 1979-08-21 | Union Carbide Corporation | Catalytic aldol condensations |
| IT1085879B (it) * | 1976-04-08 | 1985-05-28 | Basf Ag | Processo per la preparazione di chetoni superiori |
| DE2625541A1 (de) * | 1976-06-05 | 1977-12-22 | Basf Ag | Verfahren zur herstellung einer zink und nickel oder kobalt enthaltenden kontaktmasse |
| US4169109A (en) * | 1978-08-10 | 1979-09-25 | International Flavors & Fragrances Inc. | Process for preparing ketones using zinc acetate condensation catalysts, products produced thereby and organoleptic uses of same |
| JPS58174339A (ja) * | 1982-04-07 | 1983-10-13 | Mitsubishi Chem Ind Ltd | ２，２−ジハロ−６−ハロ−６−（１−ハロイソブチル）シクロヘキサノン |
| US4476324A (en) * | 1982-06-02 | 1984-10-09 | Union Carbide Corporation | Catalyzed aldol condensations |
| US4521629A (en) * | 1984-06-29 | 1985-06-04 | American Cyanamid Company | Method for the preparation of 1,5-bis-aryl-1,4-pentadien-3-ones |
| US5026919A (en) * | 1985-12-20 | 1991-06-25 | Mobil Oil Corporation | Base-catalyzed reactions using zeolite catalysts |
| US4694108A (en) * | 1986-08-01 | 1987-09-15 | Phillips Petroleum Company | Synthesis of higher ketones |
| US5072051A (en) * | 1989-06-19 | 1991-12-10 | Aristech Chemical Corporation | Preparation of methyl isopropenyl ketone |
| US5004839A (en) * | 1989-10-23 | 1991-04-02 | Aristech Chemical Corporation | Preparation of unsaturated ketones from acetone and paraformaldehyde (II) |
| US5372995A (en) * | 1994-04-15 | 1994-12-13 | International Flavors & Fragrances Inc. | Reduced reaction product of protonic acid catalyzed reaction of methyl ethyl ketone and benzaldehyde and perfume uses thereof |
| US5583263A (en) * | 1995-08-30 | 1996-12-10 | Shell Oil Company | Process of making ketones |
| US5637774A (en) * | 1995-09-29 | 1997-06-10 | Eastman Chemical Company | Process for the production of vinyl carbonyls |
| US5955636A (en) * | 1996-07-05 | 1999-09-21 | Kuraray Co., Ltd. | Process for producing 6-methyl-3-hepten-2-one and 6-methyl-2-heptanone analogues, and process for producing phyton or isophytol |
| DE10044390A1 (de) * | 2000-09-08 | 2002-03-21 | Degussa | Verfahren zur Herstellung von 6-Methylheptanon |
| DE10111071A1 (de) | 2001-03-08 | 2002-09-19 | Degussa | Verfahren zur Herstellung von Methylketonen |
| DE10112099A1 (de) | 2001-03-14 | 2002-09-19 | Degussa | Verbessertes Verfahren zur Herstellung von 6-Methylheptanon |
| EP2109597A1 (en) * | 2007-01-30 | 2009-10-21 | DSM IP Assets B.V. | Process for preparing dienones |
| EP2805935B1 (en) * | 2013-05-21 | 2018-08-29 | International Flavors & Fragrances, Inc. | Green process for producing 3-methyl-3-pentene-2-one |
| IN2013MU02838A (cg-RX-API-DMAC7.html) * | 2013-08-30 | 2015-07-03 | Godavari Biorefineries Ltd | |
| WO2017098050A1 (en) * | 2015-12-11 | 2017-06-15 | Dsm Ip Assets B.V. | Process for the manufacture of 6,10,14-trimethylpentadecan-2-one, isophytol and alpha-tocopherol |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2549508A (en) * | 1948-10-15 | 1951-04-17 | Standard Oil Dev Co | Preparation of unsaturated ketones and aldehydes |
| GB909941A (en) * | 1959-09-15 | 1962-11-07 | Exxon Research Engineering Co | Condensation of ketones to prepare higher molecular weight ketones |
| US3316303A (en) * | 1961-06-12 | 1967-04-25 | Exxon Research Engineering Co | Synthesis of higher ketones |
| GB1010695A (en) * | 1961-12-22 | 1965-11-24 | Exxon Research Engineering Co | Process for the production of alpha, beta unsaturated carbonyl compounds |
-
0
- BE BE789849D patent/BE789849A/xx not_active IP Right Cessation
-
1972
- 1972-10-10 US US05/295,959 patent/US4005147A/en not_active Expired - Lifetime
- 1972-10-11 FR FR7235982A patent/FR2156246B1/fr not_active Expired
- 1972-10-12 GB GB4709072A patent/GB1390465A/en not_active Expired
- 1972-10-12 CH CH1492972A patent/CH603520A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH603520A5 (cg-RX-API-DMAC7.html) | 1978-08-15 |
| DE2150992A1 (de) | 1973-04-19 |
| US4005147A (en) | 1977-01-25 |
| FR2156246A1 (cg-RX-API-DMAC7.html) | 1973-05-25 |
| FR2156246B1 (cg-RX-API-DMAC7.html) | 1976-01-30 |
| DE2150992B2 (de) | 1977-02-24 |
| BE789849A (fr) | 1973-04-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |