CH233190A - Fragrance mixture. - Google Patents
Fragrance mixture.Info
- Publication number
- CH233190A CH233190A CH233190DA CH233190A CH 233190 A CH233190 A CH 233190A CH 233190D A CH233190D A CH 233190DA CH 233190 A CH233190 A CH 233190A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- parts
- fragrance mixture
- oil
- methyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 6
- 239000003205 fragrance Substances 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 6
- 230000035943 smell Effects 0.000 claims description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- 239000010671 sandalwood oil Substances 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 241000221035 Santalaceae Species 0.000 description 3
- 235000008632 Santalum album Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 3
- 229940117916 cinnamic aldehyde Drugs 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000001306 (7E,9E,11E,13E)-pentadeca-7,9,11,13-tetraen-1-ol Substances 0.000 description 1
- -1 2-oxo-3-methyl-6-cyclohexylhexane Chemical compound 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- 241000402754 Erythranthe moschata Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000010627 cedar oil Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010679 vetiver oil 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
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
-
- 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
- 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
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/105—Saturated compounds containing keto groups bound to acyclic carbon atoms containing rings
- C07C49/11—Saturated compounds containing keto groups bound to acyclic carbon atoms containing rings monocyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
Description
Riechstoffgemisch. Sandelholz wird aus den in den Tropen wachsenden Santalaoeen gewonnen. Sein Hauptbestandteil ist das in einer a- und ss Form vorkommende Santalol. Ein chemischer Aufbau dieser Verbindungen ist bisher nicht geglückt, so @dass man bei der Verwendung dieses für die Feinparfümerie wichtigen Stof fes nur auf das natürliche,Sandelholz ange wiesen ist.
Es wurde nun .gefunden, @dass man auf recht einfache Weise zu neuen Austausch stoffen für ,Sandelholzöl kommen kann, die zwar chemisch von den natürlichen Bestand teilen des Sandelholzöls weitgehend verschie den sind, jedoch geruchlich dies-en Natur stoffen sehr nahe kommen.
Man erhält die in Frage kommenden neuen Austauschstoffe, wenn man Zimtaldlehyd in saurem Medium mit Methyläthylli:eton bezw. einem höheren Homologen desselben kondensiert, das Kon- densationsprodukt vollständig hydriert und aus dem erhaltenen sekundären Alkohol das entsprechende Ketori bildet. Kondensiert ran Zimtaldehyd mit Methyläthylketon unter der Einwirkung eines.
sauren Agens"so erhält man 2-Oxo,-3-methyl-6-p@henyl-hexadien-(3,5) der Formel
EMI0001.0031
und dieses geton kann :durch Hydrierung in das 2-Oxy-3,-mathyl-6-cyclohexyl-hexan der Formel
EMI0001.0034
übergeführt werden. Wenn man aus diesem Alkohol dann durch Oxydation oder Dehy- drierung das entsprechende $eten :der Formel
EMI0002.0001
herstellt, so erhält man einen Körper, der einen ausgesprochenen, starken Geruch nach Saüdelholz besitzt.
Ganz ähnlich riechende Verbindungen können analog erhalten werden, wenn man Zimtaldehyd mit andern Ketonen konden siert, z. B. mit Diäthylketon.
Gegenstand des vorliegenden Patentes ist ein Riechstoffgemisch, welches dadurch ge kennzeichnet ist, dass es eine nach Sandelholz riechende Verbindung der allgemeinen Formel
EMI0002.0007
in welcher R einen niedrigen Alkylrest be- .deutet, enthält.
EMI0002.0011
<I>Beispiel <SEP> 1:</I>
<tb> <I>Sandelholzöl <SEP> künstlich</I>
<tb> 2-Oxo-3-methyl-6-cyclolrexy <SEP> l-hexan <SEP> 50 <SEP> Teile
<tb> Cedernhalzöl <SEP> 47 <SEP> "
<tb> Rosenöl <SEP> künstlich <SEP> 3
<tb> 100 <SEP> Teile
<tb> <I>Beispiel <SEP> 2:</I>
<tb> <I>Chypre <SEP> Base</I>
<tb> Bergamotteöl <SEP> 39.7 <SEP> Teile
<tb> Vetiveröl <SEP> 6.8 <SEP> "
<tb> Eichenmoos <SEP> absolut <SEP> 10 <SEP> "
<tb> Patschouliöl <SEP> 10 <SEP> "
<tb> Cumarin <SEP> 20 <SEP> .,
<tb> Moschus <SEP> Ambrett'e <SEP> 3,5 <SEP> "
<tb> Sandelholzöl <SEP> künstlich <SEP> (s. <SEP> oben) <SEP> 10 <SEP> ,
<tb> 100 <SEP> Teile Den oben bezeichneten Austauschstoff für Sandelholzöl kann man z.
B. auf folgende Weise erhalten: Man leitet in 2000-3000 Teile 2-Oxobutan (Methyläthylketon) und 1000 Teile Zimt aldehyd bei 0-5 150 g Chlorwasserstoff ein und lässt 24 Stunden bei .gewöhnlicher Tem peratur stehen. Darauf gibt man unter Rüh ren 1000 Teile 15 % ige Natronlauge zu, de stilliert das überschüssige 2-Oxobutan ab und fraktioniert im Vakuum.
Man erhält das 2- Oxo-3-methyl-6-phenyl-hexadien-(3,5), einen mit schwach gelber Farbe kristallisierenden Körper vom Schmelzpunkt 65-69 und Kp. 165-170 bei 4-5 mm Druck, das mir einen schwachen wertlosen Geruch besitzt. 1000 Teile dieses Körpers werden zunächst mit einem der üblichen Katalysatoren zum gesättigten Keton bezw. Alkohol hydriert; hierauf werden nach Abtrennung des Kata lysators 40-50 Teile Nickel in hochaktiver Form, z.
B. als Skelettkatalysator, zugegeben, und bei Drucken von 20-50 Atm. und einer Temperatur von 150-200 wird die voll ständige Hydrierung durchgeführt. Man er hält so das 2-Oxy-3-methyl-6-cyclohexyl- hexan. Sel.bstvenständlich kann die Hydrie rung in Gegenwart eines hochaktiven Nickel- katalysators auch in einem Arbeitsgang durchgeführt werden.
Für die Herstellung des Ketons werden 900 Teile der genannten Verbindung mit 900 Teilen Eisessig und 900 Teilen Wasser verrührt und mit einer Lösung von 450 Tei- letl 1V@itriuml)ichromat in 1100 Teilen 50 % iger Sch#,N-efelsäirre innerhalb von 2 Stun- df>n versetzt.
Man rührt noch einige Zeit nach und erhält beim Aufarbeiten das 2-Oxo-3- methyl-6-cyc.lohexyl-hexan vom Kp. 118 bis 120 bei 3-4 mm Druck. Dieses Keton hat einen ausgesprochenen Sandelholzölgeruch.
Ähnlich riechende Verbindungen aus an- Jern Ketonen, z. B. Diäthylketon, sind in analog "er Weise erhältlich.
Fragrance mixture. Sandalwood is obtained from the Santalaoeen growing in the tropics. Its main component is santalol, which occurs in an a and ss form. A chemical structure of these compounds has not yet been successful, so that when using this substance, which is important for fine perfumery, one is only dependent on natural sandalwood.
It has now been found that new substitutes for sandalwood oil can be found in a very simple way, which are chemically largely different from the natural components of sandalwood oil, but which odor come very close to these natural substances.
The new substitutes in question are obtained if cinnamaldehyde is used in an acidic medium with Methyläthylli: eton or. condensed to a higher homologue of the same, the condensation product is completely hydrogenated and the corresponding ketori is formed from the secondary alcohol obtained. Cinnamaldehyde condenses with methyl ethyl ketone under the action of a.
acidic agent ", 2-oxo, -3-methyl-6-p @henyl-hexadiene- (3,5) of the formula is obtained
EMI0001.0031
and this can be done: by hydrogenation into the 2-oxy-3, -mathyl-6-cyclohexyl-hexane of the formula
EMI0001.0034
be transferred. If this alcohol is then oxidized or dehydrated to obtain the corresponding etene: the formula
EMI0002.0001
produces a body that has a pronounced, strong smell of Saüdelholz.
Completely similar-smelling compounds can be obtained analogously if you condense cinnamaldehyde with other ketones, z. B. with diethyl ketone.
The subject of the present patent is a fragrance mixture which is characterized in that it is a compound of the general formula that smells of sandalwood
EMI0002.0007
in which R denotes a lower alkyl radical, contains.
EMI0002.0011
<I> Example <SEP> 1: </I>
<tb> <I> Sandalwood oil <SEP> artificial </I>
<tb> 2-Oxo-3-methyl-6-cyclolrexy <SEP> 1-hexane <SEP> 50 <SEP> parts
<tb> Cedar wood oil <SEP> 47 <SEP> "
<tb> rose oil <SEP> artificial <SEP> 3
<tb> 100 <SEP> parts
<tb> <I> Example <SEP> 2: </I>
<tb> <I> Chypre <SEP> Base </I>
<tb> Bergamot Oil <SEP> 39.7 <SEP> parts
<tb> Vetiver oil <SEP> 6.8 <SEP> "
<tb> Oak moss <SEP> absolute <SEP> 10 <SEP> "
<tb> Patchouli oil <SEP> 10 <SEP> "
<tb> Coumarin <SEP> 20 <SEP>.,
<tb> Musk <SEP> Ambrett'e <SEP> 3,5 <SEP> "
<tb> sandalwood oil <SEP> artificial <SEP> (see <SEP> above) <SEP> 10 <SEP>,
<tb> 100 <SEP> parts The substitute for sandalwood oil mentioned above can be used e.g.
B. obtained in the following manner: One passes in 2000-3000 parts of 2-oxobutane (methyl ethyl ketone) and 1000 parts of cinnamon aldehyde at 0-5 150 g of hydrogen chloride and allowed to stand for 24 hours at .gewöhnlicher Tem temperature. Then 1000 parts of 15% sodium hydroxide solution are added with stirring, the excess 2-oxobutane is distilled off and fractionated in vacuo.
The 2-oxo-3-methyl-6-phenyl-hexadiene- (3.5) is obtained, a body which crystallizes with a pale yellow color and has a melting point of 65-69 and a boiling point of 165-170 at 4-5 mm pressure has a faint worthless odor. 1000 parts of this body are first BEZW with one of the usual catalysts to saturated ketone. Hydrogenated alcohol; thereupon 40-50 parts of nickel in highly active form, z.
B. as a skeletal catalyst, added, and at pressures of 20-50 atm. and a temperature of 150-200 the complete hydrogenation is carried out. So he keeps the 2-oxy-3-methyl-6-cyclohexyl hexane. Of course, the hydrogenation can also be carried out in one operation in the presence of a highly active nickel catalyst.
For the production of the ketone, 900 parts of the compound mentioned are stirred with 900 parts of glacial acetic acid and 900 parts of water and treated with a solution of 450 parts of 1V @ itriuml) ichromate in 1100 parts of 50% sodium sulfate within 2 hours - df> n offset.
The mixture is stirred for a while and 2-oxo-3-methyl-6-cyclohexylhexane with a boiling point of 118 to 120 is obtained at 3-4 mm pressure. This ketone has a pronounced sandalwood oil odor.
Similar-smelling compounds from other ketones, e.g. B. diethyl ketone are available in an analogous manner.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE233190X | 1942-02-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH233190A true CH233190A (en) | 1944-07-15 |
Family
ID=5884841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH233190D CH233190A (en) | 1942-02-07 | 1942-12-05 | Fragrance mixture. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH233190A (en) |
-
1942
- 1942-12-05 CH CH233190D patent/CH233190A/en unknown
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