DE165895C - - Google Patents
Info
- Publication number
- DE165895C DE165895C DENDAT165895D DE165895DA DE165895C DE 165895 C DE165895 C DE 165895C DE NDAT165895 D DENDAT165895 D DE NDAT165895D DE 165895D A DE165895D A DE 165895DA DE 165895 C DE165895 C DE 165895C
- Authority
- DE
- Germany
- Prior art keywords
- linalool
- nerol
- esters
- percent
- contain
- 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.)
- Active
Links
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 claims description 12
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 claims description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- 229930007744 linalool Natural products 0.000 claims description 6
- 229960000583 Acetic Acid Drugs 0.000 claims description 4
- 239000000341 volatile oil Substances 0.000 claims description 3
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- WUOACPNHFRMFPN-UHFFFAOYSA-N Terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 claims 1
- UWKAYLJWKGQEPM-LBPRGKRZSA-N Linaloyl acetate Natural products CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 3
- KRVSOGSZCMJSLX-UHFFFAOYSA-L Chromic acid Chemical compound O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 2
- CDOSHBSSFJOMGT-SNVBAGLBSA-N Linalool Chemical compound CC(C)=CCC[C@](C)(O)C=C CDOSHBSSFJOMGT-SNVBAGLBSA-N 0.000 description 2
- 239000001111 citrus aurantium l. leaf oil Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VFNGKCDDZUSWLR-UHFFFAOYSA-N Disulfuric acid Chemical compound OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- BFBPISPWJZMWJN-UHFFFAOYSA-N methyl 2-[(7-hydroxy-3,7-dimethyloctylidene)amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1N=CCC(C)CCCC(C)(C)O BFBPISPWJZMWJN-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- -1 unsaturated aliphatic terpene alcohols Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
JVl 165895 KLASSE 12 o. JVl 165895 CLASS 12 o.
Nach dem Verfahren des Patents 165894 wird durch Einwirkung von Eisessig und Schwefelsäure oder von Essigsäureanhydrid auf Linalool oder solches enthaltende ätherische Öle Nerol erhalten, das man mittels Phtalsäureanhydrid oder der Anhydride anderer zweibasischer Säuren aus dem Reaktionsprodukt isolieren kann. Es hat sich nun gezeigt, daß an Stelle von Linalool auch dessen Ester mit Essigsäure und anderen Fettsäuren bezw. Öle, welche, wie z. B. Petitgrainöl, diesen Alkohol und dessen Ester enthalten, zur Gewinnung des Nerols verwendet werden können, wobei unter Linalool alle diejenigen ungesättigten aliphatischen Terpenalkohole C10 Ti18 O zu verstehen sind, welche bei etwa 195 bis 200° C. sieden und bei der Oxydation mit Chromsäuregemisch Citrale geben, also auch Coriandrol, Nerolol, Lavendol, Aurantiol und andere.According to the method of patent 165894, nerol is obtained by the action of glacial acetic acid and sulfuric acid or acetic anhydride on linalool or essential oils containing such, which can be isolated from the reaction product by means of phthalic anhydride or the anhydrides of other dibasic acids. It has now been shown that instead of linalool its esters with acetic acid and other fatty acids BEZW. Oils which, e.g. B. petitgrain oil, this alcohol and its ester, can be used to obtain the nerol, under linalool all those unsaturated aliphatic terpene alcohols C 10 Ti 18 O are to be understood, which boil at about 195 to 200 ° C. and during oxidation give citrale with chromic acid mixture, also Coriandrol, Nerolol, Lavendol, Aurantiol and others.
Die Darstellung des Nerols aus den Estern des Linalools sowie den diese Verbindungen enthaltenden ätherischen Ölen erfolgt in analoger Weise wie bei dem Verfahren des Patents 165894.The representation of nerol from the esters of linalool and these compounds containing essential oils is carried out in a manner analogous to the method of Patent 165894.
i. 2 kg technisches Linalylacetat (etwa 80 Prozent Ester enthaltend) werden mit ι Y2 kg Essigsäure etwa 8 Stunden am Rückflußkühler zum Kochen erhitzt. Das miti. 2 kg of technical grade linalyl acetate (containing about 80 percent ester) are heated to boiling for about 8 hours on a reflux condenser with ι Y 2 kg of acetic acid. That with
Wasser ausgefällte Reaktionsprodukt wird mit alkoholischem Kali, analog dem Beispiel ι in der Beschreibung des Patents 165894, verseift und in gleicher Weise, wie dort beschrieben, auf Nerol weiter verarbeitet. Die Ausbeute beträgt etwa 15 Prozent.The reaction product precipitated in water is treated with alcoholic potash, analogously to the example in the description of patent 165894, saponified and in the same way as described there, further processed on nerol. The yield is about 15 percent.
2. 2 kg Petitgrainöl (rohes oder rektifiziertes bezw. fraktioniertes) werden mit 1 1J2 kg Essigsäureanhydrid etwa 7 Stunden am Rückflußkühler gekocht. Die weitere Verarbeitung des mit Wasser ausgefällten Reaktipnsproduktes erfolgt nach Beispiel 1. Ausbeute 10 bis 20 Prozent.2. 2 kg of petitgrain oil (crude or rectified or fractionated) are refluxed with 1 1 J 2 kg of acetic anhydride for about 7 hours. The further processing of the reaction product precipitated with water takes place according to Example 1. Yield 10 to 20 percent.
3. An Stelle des Linalools in Beispiel 1 der Beschreibung des Patents 165894 werden 2 kg technisches Linalylacetat (etwa 80 Prozent Ester enthaltend) angewandt; im übrigen wird wie dort angegeben verfahren. Ausbeute 5 bis 10 Prozent.3. In place of the linalool in example 1, the description of patent 165894 will be used 2 kg of technical grade linalyl acetate (containing about 80 percent ester) used; Furthermore proceed as indicated there. Yield 5 to 10 percent.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE165895C true DE165895C (en) |
Family
ID=431344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT165895D Active DE165895C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE165895C (en) |
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0
- DE DENDAT165895D patent/DE165895C/de active Active
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