DE876241C - Process for the production of fragrances from terpene phenols - Google Patents
Process for the production of fragrances from terpene phenolsInfo
- Publication number
- DE876241C DE876241C DEL3608D DEL0003608D DE876241C DE 876241 C DE876241 C DE 876241C DE L3608 D DEL3608 D DE L3608D DE L0003608 D DEL0003608 D DE L0003608D DE 876241 C DE876241 C DE 876241C
- Authority
- DE
- Germany
- Prior art keywords
- fragrances
- production
- terpene phenols
- terpene
- parts
- 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 terpene phenols Chemical class 0.000 title claims description 11
- 235000007586 terpenes Nutrition 0.000 title claims description 10
- 239000003205 fragrance Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 5
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 description 4
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 4
- 229930006739 camphene Natural products 0.000 description 4
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 4
- 239000010671 sandalwood oil Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 244000284012 Vetiveria zizanioides Species 0.000 description 2
- 235000007769 Vetiveria zizanioides Nutrition 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 2
- 229960001867 guaiacol Drugs 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-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
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DTGKSKDOIYIVQL-MRTMQBJTSA-N Isoborneol Natural products C1C[C@@]2(C)[C@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-MRTMQBJTSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229940116229 borneol Drugs 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
-
- 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
- C07C49/517—Saturated compounds containing a keto group being part of a ring containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Riechstoffen aus Terpenphenolen Wie im Patent 86o 946, dessen Anspruch lautet: Verfahren zur Herstellung von Riechstoffen aus Terpenphenolen, dadurch gekennzeichnet, daß man Terpenphenole katalytisch reduziert und gegebenenfalls die erhaltenen Terpencyclohexanole zu den entsprechenden Ketonen oxydiert, beschrieben ist, stellen die Hydrierungsprodukte von Terpenphenolen wertvolle Riechstoffe dar.Process for the production of fragrances from terpene phenols Like in patent 86o 946, whose claim reads: Process for the production of fragrances from terpene phenols, characterized in that terpene phenols are reduced catalytically and optionally the terpene cyclohexanols obtained to give the corresponding ketones oxidized, is described, the hydrogenation products of terpene phenols are valuable Odoriferous substances.
Wie nun weiter gefunden wurde, sind auch solche hydrierten Terpenphenole bzw. die entsprechenden Ketone für den gleichen Zweck verwendbar, in welchen die Oxygruppe des Cyclohexanrestes veräthert ist, ebenso wie solche, in welchen neben einer Alkoxygruppe noch eine zweite freie oder verätherte Oxygruppe vorhanden ist. Insbesondere haben sich die durch Kondensation von Guajakol und Guäthol und anschließende Hydrierung erhaltenen Verbindungen, nämlich das i-Oxy-2-methOxy-4-camphylcyclohexan und i-Oxy-2-äthoxy-4-camphylcyclohexan als außerordentlich wertvolle, trotz des hohen Siedepunktes stark riechende, dem natürlichen Sandelholzül weitgehend ähnliche Produkte erwiesen. Desgleichen sind die aus diesen Alkoholen erhältlichen Ketone wertvolle Produkte, deren Geruch mehr in Richtung Vetiver liegt.As has now been further found, such are also hydrogenated terpene phenols or the corresponding ketones can be used for the same purpose in which the Oxy group of the cyclohexane residue is etherified, as well as those in which beside an alkoxy group still has a second free or etherified oxy group. In particular, the condensation of guaiacol and guathol and subsequent Compounds obtained by hydrogenation, namely i-oxy-2-methOxy-4-camphylcyclohexane and i-oxy-2-ethoxy-4-camphylcyclohexane as extremely valuable, despite the has a strong smelling high boiling point and is largely similar to the natural sandalwood oil Products proven. So are the ketones obtainable from these alcohols valuable products, the smell of which is more towards the vetiver.
Beispiel i iooo Teile i-Oxy-2-methoxy-4-camphylbenzol vom Kp,.e = 205 bis 2i5° (erhältlich durch Kondensation von Guajakol mit Camphen mittels Borfluorid) werden mit 3o Teilen eines hochaktiven Nickelkatalysators bei q0 at und 18o bis 2oo° mehrere Stunden mit Wasserstoff behandelt. Man erhält 87o Teile z-Oxy-2-methoxy-q.-camphylcyclohexan vom Kp 7_8 = igo bis 1g5° als farblose viskose Flüssigkeit mit ausgezeichnetem Sandelholzölgerach.Example iooo parts of i-oxy-2-methoxy-4-camphylbenzene with a boiling point of .e = 205 to 2i5 ° (obtainable by condensation of guaiacol with camphene using boron fluoride) are mixed with 3o parts of a highly active nickel catalyst at q0 at and 18o to 2oo ° treated with hydrogen for several hours. 87o parts of z-oxy-2-methoxy-q.-camphylcyclohexane with a boiling point of 7-8 = igo to 1g5 ° are obtained as a colorless, viscous liquid with an excellent smell of sandalwood oil.
Werden 3oo Teile mit 6oo Teilen Eisessig und 15o Teilen Wasser verrührt und in i bis il/, Stunden i2o Teile Natriumbichromat, in 36o Teilen 500/"iger Schwefelsäure gelöst, bei : 2o bis 25° zugesetzt und noch i Stunde nachgerührt, so erhält man nach Verdünnen mit Wasser, Abtrennen des Öles und fraktionierter Destillation im Vakuum 225 Teile des bei i7ö bis i75° unter q. bis 5 mm Druck siedenden i-Oxo-2-methoxy-q.-camphylcyclohexans mit angenehmem, in Richtung Vetiver gehendem Sandelholzölgeruch.300 parts are stirred with 600 parts of glacial acetic acid and 150 parts of water and in one to one and a half hours I20 parts of sodium dichromate, in 36o parts of 500% sulfuric acid dissolved, added at: 20 to 25 ° and stirred for a further hour, this gives after dilution with water, separation of the oil and fractional distillation in Vacuum 225 parts of that at i7ö to i75 ° below q. i-Oxo-2-methoxy-q.-camphylcyclohexane boiling up to 5 mm pressure with a pleasant smell of sandalwood oil, tending towards vetiver.
In gleicher Weise läßt sich durch Kondensation von Camphen mit Guäthol das i-Oxy-2-äthoxy-4.-camphylbenzol vom Kp" = 215 bis 225° herstellen. Durch Hydrierung erhält man daraus das i-Oxy-2-äthoxy-4-camphylcyclohexan vom Kp4_5 = 2io bis 2i5° mit feinem, starkem Sandelholzölgeruch. Dieses läßt sich in das entsprechende Keton überführen. Ferner lassen sich ähnliche, wenn auch etwas schwächer riechende Verbindungen erhalten, wenn man das Camphen mit Resorcinmonomethyläther, Hydrochinonmonomethyläther, Anisol und Veratrol kondensiert und das Kondensationsprcdukt hydriert und gegebenenfalls zum Keton oxydiert.In the same way, by condensation of camphene with Guäthol the i-oxy-2-ethoxy-4.-camphylbenzene with b.p. "= 215 to 225 °. By hydrogenation the i-oxy-2-ethoxy-4-camphylcyclohexane is obtained therefrom with a boiling point of 4_5 = 2io to 2i5 ° with a fine, strong smell of sandalwood oil. This can be converted into the corresponding ketone convict. Furthermore, similar, albeit somewhat weaker-smelling compounds can be found obtained if the camphene with resorcinol monomethyl ether, hydroquinone monomethyl ether, Anisole and veratrole condensed and the condensation product hydrogenated and optionally oxidized to the ketone.
An Stelle von Camphen können auch Terpene, wie Pinen und Dipenten, zur Verwendung kcrrrren. Es können ferner an Stelle der Terpene Alkohole, z. B. Borneol oder Isoborneol, unter Erhitzen in Gegen#"iart von Aktiverde zur Kondensation mit den gerannten Phenoläthern verwendet werden.Instead of camphene, terpenes such as pinene and dipentene, kcrrrren for use. It can also be used instead of the terpenes alcohols such. B. Borneol or isoborneol, with heating in the form of active earth for condensation be used with the raced phenolic ethers.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEL3608D DE876241C (en) | 1943-04-07 | 1943-04-07 | Process for the production of fragrances from terpene phenols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEL3608D DE876241C (en) | 1943-04-07 | 1943-04-07 | Process for the production of fragrances from terpene phenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE876241C true DE876241C (en) | 1953-05-11 |
Family
ID=7256265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEL3608D Expired DE876241C (en) | 1943-04-07 | 1943-04-07 | Process for the production of fragrances from terpene phenols |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE876241C (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3499937A (en) * | 1961-06-09 | 1970-03-10 | Givaudan Corp | Polycyclic alcohol,compositions containing same and process therefor |
| US4014944A (en) * | 1976-03-01 | 1977-03-29 | International Flavors & Fragrances Inc. | Process and product produced by said process |
| US4131557A (en) * | 1976-12-22 | 1978-12-26 | International Flavors & Fragrances Inc. | Soap composition |
| DE1184757B (en) * | 1962-11-28 | 1981-06-04 | PROCESS FOR THE PREPARATION OF REACTION PRODUCTS FROM 3,4-DIMETHYLPHENOL | |
| JP2013511511A (en) * | 2009-11-19 | 2013-04-04 | イッサム・リサーチ・ディベロップメント・カンパニー・オブ・ザ・ヘブルー・ユニバーシティ・オブ・エルサレム・リミテッド | Novel arylated camphene, process for its production and use thereof |
-
1943
- 1943-04-07 DE DEL3608D patent/DE876241C/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3499937A (en) * | 1961-06-09 | 1970-03-10 | Givaudan Corp | Polycyclic alcohol,compositions containing same and process therefor |
| DE1184757B (en) * | 1962-11-28 | 1981-06-04 | PROCESS FOR THE PREPARATION OF REACTION PRODUCTS FROM 3,4-DIMETHYLPHENOL | |
| US4014944A (en) * | 1976-03-01 | 1977-03-29 | International Flavors & Fragrances Inc. | Process and product produced by said process |
| US4061686A (en) * | 1976-03-01 | 1977-12-06 | International Flavors & Fragrances Inc. | Cyclohexane diol composition |
| US4131557A (en) * | 1976-12-22 | 1978-12-26 | International Flavors & Fragrances Inc. | Soap composition |
| US4131555A (en) * | 1976-12-22 | 1978-12-26 | International Flavors & Fragrances Inc. | Detergent composition |
| JP2013511511A (en) * | 2009-11-19 | 2013-04-04 | イッサム・リサーチ・ディベロップメント・カンパニー・オブ・ザ・ヘブルー・ユニバーシティ・オブ・エルサレム・リミテッド | Novel arylated camphene, process for its production and use thereof |
| US9365534B2 (en) | 2009-11-19 | 2016-06-14 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Arylated camphenes, processes for their preparation and uses thereof |
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