DE2202249C2 - Verfahren zur Gewinnung von α-Cedren aus der Kohlenwasserstoffraktion von Zedernholzöl - Google Patents
Verfahren zur Gewinnung von α-Cedren aus der Kohlenwasserstoffraktion von ZedernholzölInfo
- Publication number
- DE2202249C2 DE2202249C2 DE2202249A DE2202249A DE2202249C2 DE 2202249 C2 DE2202249 C2 DE 2202249C2 DE 2202249 A DE2202249 A DE 2202249A DE 2202249 A DE2202249 A DE 2202249A DE 2202249 C2 DE2202249 C2 DE 2202249C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- mixture
- cedrene
- hydrocarbon
- hydrocarbon fraction
- 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
- 229930195733 hydrocarbon Natural products 0.000 title claims description 42
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 41
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 26
- 239000010627 cedar oil Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- IRAQOCYXUMOFCW-OSFYFWSMSA-N cedr-8-ene Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1C(C)=CC2 IRAQOCYXUMOFCW-OSFYFWSMSA-N 0.000 title description 6
- IRAQOCYXUMOFCW-UHFFFAOYSA-N di-epi-alpha-cedrene Natural products C1C23C(C)CCC3C(C)(C)C1C(C)=CC2 IRAQOCYXUMOFCW-UHFFFAOYSA-N 0.000 title description 4
- 238000011084 recovery Methods 0.000 title description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 30
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 24
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 21
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 12
- 235000019253 formic acid Nutrition 0.000 claims description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 8
- 235000006408 oxalic acid Nutrition 0.000 claims description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- -1 alkane monocarboxylic acid Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 description 27
- 229960000583 acetic acid Drugs 0.000 description 14
- 238000006317 isomerization reaction Methods 0.000 description 14
- WXQGPFZDVCRBME-QEJZJMRPSA-N (-)-thujopsene Chemical compound C([C@@]1(C)CC=C2C)CCC(C)(C)[C@]11[C@H]2C1 WXQGPFZDVCRBME-QEJZJMRPSA-N 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- WXQGPFZDVCRBME-UHFFFAOYSA-N thujopsene Natural products CC1=CCC2(C)CCCC(C)(C)C22C1C2 WXQGPFZDVCRBME-UHFFFAOYSA-N 0.000 description 8
- WLNGPDPILFYWKF-OAHLLOKOSA-N (-)-beta-chamigrene Chemical compound C1CC(C)=CC[C@]21C(C)(C)CCCC2=C WLNGPDPILFYWKF-OAHLLOKOSA-N 0.000 description 7
- BDOIVSNOYYRVKL-UHFFFAOYSA-N 12(11-10)-Abeo-4-bromo-3-chloro-7,8-epxoy-11(13)-chamigren-l-ol Natural products C=C1C(C)CC2OC2(C)C21CC(Br)C(C)(Cl)CC2O BDOIVSNOYYRVKL-UHFFFAOYSA-N 0.000 description 7
- 229930002306 chamigrene Natural products 0.000 description 7
- 241000736890 Thujopsis Species 0.000 description 6
- SDTYFWAQLSIEBH-UHFFFAOYSA-N undec-3-ene Chemical compound CCCCCCCC=CCC SDTYFWAQLSIEBH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- DYLPEFGBWGEFBB-UHFFFAOYSA-N beta-Cedren Natural products C1C23C(C)CCC3C(C)(C)C1C(=C)CC2 DYLPEFGBWGEFBB-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/553—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/2206—Catalytic processes not covered by C07C5/23 - C07C5/31
- C07C5/2226—Catalytic processes not covered by C07C5/23 - C07C5/31 with inorganic acids; with salt or anhydrides of acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/29—Rearrangement of carbon atoms in the hydrocarbon skeleton changing the number of carbon atoms in a ring while maintaining the number of rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/31—Rearrangement of carbon atoms in the hydrocarbon skeleton changing the number of rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00107430A US3799987A (en) | 1971-01-18 | 1971-01-18 | 4-acetic-6,8a-ethano-1,1,6-trimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene, process for making same and compositions containing same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2202249A1 DE2202249A1 (de) | 1972-07-27 |
| DE2202249C2 true DE2202249C2 (de) | 1983-01-05 |
Family
ID=22316595
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2202249A Expired DE2202249C2 (de) | 1971-01-18 | 1972-01-18 | Verfahren zur Gewinnung von α-Cedren aus der Kohlenwasserstoffraktion von Zedernholzöl |
| DE2202248A Expired DE2202248C2 (de) | 1971-01-18 | 1972-01-18 | 4-Acetyl-6,8a-äthano-1,1,6-trimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalin, Verfahren zu dessen Herstellung und Riechstoffkompositionen mit einem Gehalt an dieser Substanz |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2202248A Expired DE2202248C2 (de) | 1971-01-18 | 1972-01-18 | 4-Acetyl-6,8a-äthano-1,1,6-trimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalin, Verfahren zu dessen Herstellung und Riechstoffkompositionen mit einem Gehalt an dieser Substanz |
Country Status (14)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3988366A (en) * | 1974-04-01 | 1976-10-26 | Takasago Perfumery Co., Ltd. | 5-Acetyl-1,2,6-trimethyltricyclo[5,3,2,02,7 ]dodeca-5-ene perfume composition |
| GB1519443A (en) * | 1974-08-09 | 1978-07-26 | Bush Boake Allen Ltd | Isolongifolene derivatives |
| US7348304B1 (en) | 2004-12-20 | 2008-03-25 | Cool Laurence G | Fragrance material |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2968660A (en) * | 1958-04-14 | 1961-01-17 | Givaudan Corp | Epoxy patchoulanes and method for preparing patchoulione therewith |
-
1971
- 1971-01-18 US US00107430A patent/US3799987A/en not_active Expired - Lifetime
- 1971-12-20 ZA ZA718499A patent/ZA718499B/xx unknown
- 1971-12-21 CH CH1881771A patent/CH565721A5/xx not_active IP Right Cessation
- 1971-12-22 AU AU37221/71A patent/AU3722171A/en not_active Expired
- 1971-12-29 CH CH59175A patent/CH577828A5/xx not_active IP Right Cessation
- 1971-12-29 CH CH1903871A patent/CH565731A5/xx not_active IP Right Cessation
- 1971-12-30 IT IT33158/71A patent/IT944597B/it active
-
1972
- 1972-01-04 ZA ZA720049A patent/ZA7249B/xx unknown
- 1972-01-06 NL NLAANVRAGE7200185,A patent/NL171439C/xx not_active IP Right Cessation
- 1972-01-06 AU AU37681/72A patent/AU3768172A/en not_active Expired
- 1972-01-07 IT IT19137/72A patent/IT946383B/it active
- 1972-01-14 BR BR211/72A patent/BR7200211D0/pt unknown
- 1972-01-17 SU SU1739340A patent/SU404218A3/ru active
- 1972-01-17 BR BR245/72A patent/BR7200245D0/pt unknown
- 1972-01-17 ES ES398921A patent/ES398921A1/es not_active Expired
- 1972-01-17 ES ES398922A patent/ES398922A1/es not_active Expired
- 1972-01-17 JP JP625272A patent/JPS5529971B1/ja active Pending
- 1972-01-18 BE BE778173A patent/BE778173A/xx unknown
- 1972-01-18 FR FR7201538A patent/FR2122926A5/fr not_active Expired
- 1972-01-18 BE BE778170A patent/BE778170A/xx unknown
- 1972-01-18 DE DE2202249A patent/DE2202249C2/de not_active Expired
- 1972-01-18 FR FR7201539A patent/FR2127006B1/fr not_active Expired
- 1972-01-18 GB GB240172A patent/GB1377803A/en not_active Expired
- 1972-01-18 JP JP719972A patent/JPS5736251B1/ja active Pending
- 1972-01-18 DE DE2202248A patent/DE2202248C2/de not_active Expired
- 1972-01-18 GB GB240272A patent/GB1343741A/en not_active Expired
- 1972-01-18 NL NL7200697A patent/NL7200697A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |