GB1056083A - A process for the manufacture of polyene ketones - Google Patents
A process for the manufacture of polyene ketonesInfo
- Publication number
- GB1056083A GB1056083A GB6595/65A GB659565A GB1056083A GB 1056083 A GB1056083 A GB 1056083A GB 6595/65 A GB6595/65 A GB 6595/65A GB 659565 A GB659565 A GB 659565A GB 1056083 A GB1056083 A GB 1056083A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ketone
- hydrocarbyl
- prepared
- acid catalyst
- ketones
- 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
- -1 polyene ketones Chemical class 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 239000003377 acid catalyst Substances 0.000 abstract 3
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 3
- 150000002576 ketones Chemical class 0.000 abstract 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 abstract 2
- 125000002070 alkenylidene group Chemical group 0.000 abstract 2
- 125000001118 alkylidene group Chemical group 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- RYJXPRUXQSAMQE-UHFFFAOYSA-N buta-1,2,3-trien-1-one Chemical compound C=C=C=C=O RYJXPRUXQSAMQE-UHFFFAOYSA-N 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- IBXNCJKFFQIKKY-UHFFFAOYSA-N 1-pentyne Chemical compound CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 abstract 1
- RSBYSUMSEPSFGX-UHFFFAOYSA-N 4,7-dimethyloct-1-en-3-ol Chemical compound OC(C=C)C(CCC(C)C)C RSBYSUMSEPSFGX-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 150000007514 bases Chemical class 0.000 abstract 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 abstract 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- IXBHYZXSUSMOPF-UHFFFAOYSA-N hexa-3,5-dienylbenzene Chemical compound C=CC=CCCC1=CC=CC=C1 IXBHYZXSUSMOPF-UHFFFAOYSA-N 0.000 abstract 1
- 150000002430 hydrocarbons Chemical group 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 239000002304 perfume Substances 0.000 abstract 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical group OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 abstract 1
- UARFKZSJGDQRLF-UHFFFAOYSA-N prop-2-ynylcyclohexane Chemical compound C#CCC1CCCCC1 UARFKZSJGDQRLF-UHFFFAOYSA-N 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 229930195735 unsaturated hydrocarbon Natural products 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (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 |
|---|---|---|---|
| CH229064A CH459982A (de) | 1964-02-25 | 1964-02-25 | Verfahren zur Herstellung von Polyenketonen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1056083A true GB1056083A (en) | 1967-01-25 |
Family
ID=4230308
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6595/65A Expired GB1056083A (en) | 1964-02-25 | 1965-02-16 | A process for the manufacture of polyene ketones |
| GB13333/66A Expired GB1056084A (en) | 1964-02-25 | 1965-02-16 | Novel ketals |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13333/66A Expired GB1056084A (en) | 1964-02-25 | 1965-02-16 | Novel ketals |
Country Status (9)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4806693A (en) * | 1985-09-27 | 1989-02-21 | Shell Oil Company | Process for the preparation of unsaturated ketones |
| CN108395380B (zh) * | 2018-04-04 | 2020-08-07 | 河南师范大学 | 一种1,3-环己二烯类化合物的合成方法 |
| CN112830957A (zh) * | 2021-01-07 | 2021-05-25 | 江西师范大学 | 一种高效制备卡非佐米的方法 |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH569684A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-03-10 | 1975-11-28 | Givaudan & Cie Sa | |
| US3886217A (en) * | 1973-02-01 | 1975-05-27 | Rhodia | Process for the preparation of alpha, beta-ethylenic ketones such as delta{hu 3{b -cis-pseudo ionones |
| US3886215A (en) * | 1973-02-01 | 1975-05-27 | Rhodia | Process using metal salt-amine complex catalysts for the preparation of alpha beta-ethylenic ketones such as delta-cis-pseudo ionones |
| US3886216A (en) * | 1973-02-01 | 1975-05-27 | Rhodia | Process for the preparation of alfa beta-ethylenic ketones |
| DE3013565A1 (de) | 1980-04-09 | 1981-10-15 | Consortium für elektrochemische Industrie GmbH, 8000 München | Neue (beta) - a -ungesaettigte ketone und isoprenoide 2,6-dienone, verfahren zu deren herstellung und ihre verwendung als geruchs- und geschmacksstoffe |
| DE3128271A1 (de) * | 1981-07-17 | 1983-02-03 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 1,1'-diacetalen |
| US4420411A (en) * | 1982-06-04 | 1983-12-13 | International Flavors & Fragrances Inc. | Process for augmenting or enhancing the aroma of detergents using unsaturated branch chain ketones |
| US4613706A (en) * | 1984-04-20 | 1986-09-23 | International Flavors & Fragrances Inc. | Isomer-directed process for producing asymmetric ketones using catalytic Claisen rearrangement of allylic ethers, intermediates, and uses of products and intermediates of process in perfumery |
| US4616095A (en) * | 1984-04-20 | 1986-10-07 | International Flavors & Fragrances Inc. | Isomer-directed process for producing asymmetric ketones using catalytic claisen rearrangement of allylic ethers, intermediates, and uses of products and intermediates of process in perfumery |
| US4594464A (en) * | 1984-05-11 | 1986-06-10 | International Flavors & Fragrances Inc. | Methyl phenethyl acetal of 2-butynal |
| FR2710911B1 (fr) * | 1993-10-07 | 1995-12-01 | Rhone Poulenc Nutrition Animal | Nouveaux intermédiaires de préparation de la vitamine A et des caroténoïdes et leur procédé de préparation. |
| DE19949796A1 (de) | 1999-10-15 | 2001-04-19 | Degussa | Verfahren zur Herstellung von ungesättigten 4,5-Allenketonen, 3,5-Dienketonen und den entsprechenden gesättigten Ketonen |
| DE10121058A1 (de) | 2001-04-28 | 2002-10-31 | Degussa | Neues Verfahren zur Herstellung von ungesättigten Ketonen |
| EP1327620A1 (en) * | 2002-01-14 | 2003-07-16 | Aventis Animal Nutrition S.A. | Process for the preparation of phytone |
| WO2008092655A1 (en) * | 2007-01-30 | 2008-08-07 | Dsm Ip Assets B.V. | Process for preparing dienones |
| EP1953134A1 (en) * | 2007-01-30 | 2008-08-06 | DSM IP Assets B.V. | Process for preparing dienones |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3029287A (en) * | 1958-08-01 | 1962-04-10 | Hoffmann La Roche | Preparation of unsaturated ketones |
| US3337634A (en) * | 1963-05-07 | 1967-08-22 | Eastman Kodak Co | Allenic ketones and process for their preparation |
-
1964
- 1964-02-25 CH CH229064A patent/CH459982A/de unknown
-
1965
- 1965-01-27 DE DEH54971A patent/DE1230783B/de active Pending
- 1965-02-08 US US431175A patent/US3456015A/en not_active Expired - Lifetime
- 1965-02-11 NL NL6501697A patent/NL6501697A/xx unknown
- 1965-02-16 GB GB6595/65A patent/GB1056083A/en not_active Expired
- 1965-02-16 GB GB13333/66A patent/GB1056084A/en not_active Expired
- 1965-02-19 FR FR6183A patent/FR1428150A/fr not_active Expired
- 1965-02-22 BR BR167373/65A patent/BR6567373D0/pt unknown
- 1965-02-23 BE BE660099D patent/BE660099A/xx unknown
- 1965-02-24 ES ES0309779A patent/ES309779A1/es not_active Expired
-
1969
- 1969-02-27 US US803046*A patent/US3632860A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4806693A (en) * | 1985-09-27 | 1989-02-21 | Shell Oil Company | Process for the preparation of unsaturated ketones |
| CN108395380B (zh) * | 2018-04-04 | 2020-08-07 | 河南师范大学 | 一种1,3-环己二烯类化合物的合成方法 |
| CN112830957A (zh) * | 2021-01-07 | 2021-05-25 | 江西师范大学 | 一种高效制备卡非佐米的方法 |
| CN112830957B (zh) * | 2021-01-07 | 2022-07-22 | 江西师范大学 | 一种制备卡非佐米的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1056084A (en) | 1967-01-25 |
| NL6501697A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-08-26 |
| ES309779A1 (es) | 1966-01-16 |
| FR1428150A (fr) | 1966-02-11 |
| US3632860A (en) | 1972-01-04 |
| DE1230783B (de) | 1966-12-22 |
| BR6567373D0 (pt) | 1973-08-16 |
| BE660099A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-08-23 |
| CH459982A (de) | 1968-07-31 |
| US3456015A (en) | 1969-07-15 |
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