DE2336798A1 - Verfahren zur herstellung von sesquiterpenketonen - Google Patents
Verfahren zur herstellung von sesquiterpenketonenInfo
- Publication number
- DE2336798A1 DE2336798A1 DE19732336798 DE2336798A DE2336798A1 DE 2336798 A1 DE2336798 A1 DE 2336798A1 DE 19732336798 DE19732336798 DE 19732336798 DE 2336798 A DE2336798 A DE 2336798A DE 2336798 A1 DE2336798 A1 DE 2336798A1
- Authority
- DE
- Germany
- Prior art keywords
- sesquiterpene
- formate
- ketones
- hydrogen peroxide
- alkyl formate
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- -1 sesquiterpene ketones Chemical class 0.000 claims description 28
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 24
- 229930004725 sesquiterpene Natural products 0.000 claims description 20
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical group CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 5
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 5
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- CQUAYTJDLQBXCQ-NHYWBVRUSA-N (-)-isolongifolene Chemical compound C([C@@H](C1)C2(C)C)C[C@]31C2=CCCC3(C)C CQUAYTJDLQBXCQ-NHYWBVRUSA-N 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- IRAQOCYXUMOFCW-CXTNEJHOSA-N cedrene Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@H]1C(C)=CC2 IRAQOCYXUMOFCW-CXTNEJHOSA-N 0.000 description 2
- AHXGRMIPHCAXFP-UHFFFAOYSA-L chromyl dichloride Chemical compound Cl[Cr](Cl)(=O)=O AHXGRMIPHCAXFP-UHFFFAOYSA-L 0.000 description 2
- IRAQOCYXUMOFCW-UHFFFAOYSA-N di-epi-alpha-cedrene Natural products C1C23C(C)CCC3C(C)(C)C1C(C)=CC2 IRAQOCYXUMOFCW-UHFFFAOYSA-N 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000004354 sesquiterpene derivatives Chemical class 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- NPNUFJAVOOONJE-ZIAGYGMSSA-N β-(E)-Caryophyllene Chemical compound C1CC(C)=CCCC(=C)[C@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-ZIAGYGMSSA-N 0.000 description 2
- WTOYNNBCKUYIKC-JMSVASOKSA-N (+)-nootkatone Chemical compound C1C[C@@H](C(C)=C)C[C@@]2(C)[C@H](C)CC(=O)C=C21 WTOYNNBCKUYIKC-JMSVASOKSA-N 0.000 description 1
- CAULGCQHVOVVRN-UHFFFAOYSA-N (3Z,9E)-Germacra-3,7(11),9-trien-6-on Natural products CC(C)=C1CC=C(C)CCC=C(C)CC1=O CAULGCQHVOVVRN-UHFFFAOYSA-N 0.000 description 1
- VCOCESNMLNDPLX-BTXGZQJSSA-N (3s,6s)-2,2,8,8-tetramethyl-octahydro-1h-2,4a-methanonapthalene-10-one Chemical compound O=C1CCC(C)(C)[C@@]2(C3)C1C(C)(C)[C@H]3CC2 VCOCESNMLNDPLX-BTXGZQJSSA-N 0.000 description 1
- CAULGCQHVOVVRN-SWZPTJTJSA-N (E,E)-germacrone Chemical compound CC(C)=C1C\C=C(C)\CC\C=C(C)\CC1=O CAULGCQHVOVVRN-SWZPTJTJSA-N 0.000 description 1
- JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- ZVSZHMFUICOVPY-UHFFFAOYSA-N Germacrone Natural products CC(=C)C1CC=C(/C)CCC=C(/C)CC1=O ZVSZHMFUICOVPY-UHFFFAOYSA-N 0.000 description 1
- 241000786363 Rhampholeon spectrum Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- NPNUFJAVOOONJE-UHFFFAOYSA-N beta-cariophyllene Natural products C1CC(C)=CCCC(=C)C2CC(C)(C)C21 NPNUFJAVOOONJE-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NPNUFJAVOOONJE-UONOGXRCSA-N caryophyllene Natural products C1CC(C)=CCCC(=C)[C@@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-UONOGXRCSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 150000002009 diols Chemical group 0.000 description 1
- WTOYNNBCKUYIKC-UHFFFAOYSA-N dl-nootkatone Natural products C1CC(C(C)=C)CC2(C)C(C)CC(=O)C=C21 WTOYNNBCKUYIKC-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical class [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 229930003658 monoterpene Natural products 0.000 description 1
- 150000002773 monoterpene derivatives Chemical class 0.000 description 1
- 235000002577 monoterpenes Nutrition 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/417—Saturated compounds containing a keto group being part of a ring polycyclic
- C07C49/423—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system
- C07C49/453—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system having three rings
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)
- Fats And Perfumes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3396072A GB1434035A (en) | 1972-07-20 | 1972-07-20 | Process for the preparation of sesquiterpene ketones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2336798A1 true DE2336798A1 (de) | 1974-01-31 |
Family
ID=10359605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732336798 Ceased DE2336798A1 (de) | 1972-07-20 | 1973-07-17 | Verfahren zur herstellung von sesquiterpenketonen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3887622A (enrdf_load_stackoverflow) |
| JP (1) | JPS5735170B2 (enrdf_load_stackoverflow) |
| CH (1) | CH582121A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2336798A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2193808B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1434035A (enrdf_load_stackoverflow) |
| IN (1) | IN138032B (enrdf_load_stackoverflow) |
| NL (1) | NL154493B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0543470A1 (de) * | 1991-11-19 | 1993-05-26 | Dragoco Gerberding & Co Aktiengesellschaft | Cyclische Isolongifolanon-Ketale, ihre Herstellung und ihre Verwendung |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1519443A (en) * | 1974-08-09 | 1978-07-26 | Bush Boake Allen Ltd | Isolongifolene derivatives |
| IL121437A (en) * | 1995-12-18 | 2000-10-31 | Firmenich & Cie | Process for the preparation of nootkatone or nootkatol or of mixtures of these compounds |
| ES2573810T3 (es) | 2012-03-27 | 2016-06-10 | International Flavors & Fragrances Inc. | Nuevos derivados de quinazolina y su uso en composiciones de perfume |
| CN111499502B (zh) * | 2020-05-15 | 2021-06-22 | 南京林业大学 | 一种罗汉柏木烷酮的合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2555927A (en) * | 1949-05-25 | 1951-06-05 | Phillips Petroleum Co | Hydroxylation of unsaturated compounds |
| GB1256535A (enrdf_load_stackoverflow) * | 1968-09-27 | 1971-12-08 | ||
| US3718698A (en) * | 1969-11-24 | 1973-02-27 | Int Flavors & Fragrances Inc | Isolongifolene processes and product |
-
1972
- 1972-07-20 GB GB3396072A patent/GB1434035A/en not_active Expired
-
1973
- 1973-07-10 NL NL737309628A patent/NL154493B/xx not_active IP Right Cessation
- 1973-07-17 US US380054A patent/US3887622A/en not_active Expired - Lifetime
- 1973-07-17 DE DE19732336798 patent/DE2336798A1/de not_active Ceased
- 1973-07-18 IN IN1683/CAL/73A patent/IN138032B/en unknown
- 1973-07-19 FR FR7326513A patent/FR2193808B1/fr not_active Expired
- 1973-07-20 CH CH1069573A patent/CH582121A5/xx not_active IP Right Cessation
- 1973-07-20 JP JP8079573A patent/JPS5735170B2/ja not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0543470A1 (de) * | 1991-11-19 | 1993-05-26 | Dragoco Gerberding & Co Aktiengesellschaft | Cyclische Isolongifolanon-Ketale, ihre Herstellung und ihre Verwendung |
| US5260459A (en) * | 1991-11-19 | 1993-11-09 | Brunke Ernst Joachim | Cyclic isolongifolanone-ketals - their manufacture and their application |
Also Published As
| Publication number | Publication date |
|---|---|
| IN138032B (enrdf_load_stackoverflow) | 1975-11-22 |
| FR2193808A1 (enrdf_load_stackoverflow) | 1974-02-22 |
| JPS5735170B2 (enrdf_load_stackoverflow) | 1982-07-27 |
| US3887622A (en) | 1975-06-03 |
| JPS4980057A (enrdf_load_stackoverflow) | 1974-08-02 |
| FR2193808B1 (enrdf_load_stackoverflow) | 1977-08-12 |
| NL154493B (nl) | 1977-09-15 |
| GB1434035A (en) | 1976-04-28 |
| CH582121A5 (enrdf_load_stackoverflow) | 1976-11-30 |
| NL7309628A (enrdf_load_stackoverflow) | 1974-01-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8131 | Rejection |