DE155287C - - Google Patents
Info
- Publication number
- DE155287C DE155287C DENDAT155287D DE155287DA DE155287C DE 155287 C DE155287 C DE 155287C DE NDAT155287 D DENDAT155287 D DE NDAT155287D DE 155287D A DE155287D A DE 155287DA DE 155287 C DE155287 C DE 155287C
- Authority
- DE
- Germany
- Prior art keywords
- percent
- alcohol
- geraniol
- oil
- nerol
- 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
- 239000000203 mixture Substances 0.000 claims description 4
- WUOACPNHFRMFPN-UHFFFAOYSA-N Terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- -1 fatty acid esters Chemical class 0.000 claims description 3
- 230000035943 smell Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000003205 fragrance Substances 0.000 claims 1
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 8
- 239000005792 Geraniol Substances 0.000 description 8
- 229930008393 geraniol Natural products 0.000 description 8
- 229940113087 geraniol Drugs 0.000 description 8
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 4
- HIGQPQRQIQDZMP-DHZHZOJOSA-N Neryl acetate Natural products CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- 239000001524 citrus aurantium oil Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 2
- UWKAYLJWKGQEPM-LBPRGKRZSA-N Linaloyl acetate Natural products CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating Effects 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 229930004021 citronellol Natural products 0.000 description 2
- 235000000484 citronellol Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000341 volatile oil Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- 244000003034 Arancio amaro Species 0.000 description 1
- 235000016840 Arancio amaro Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 235000009046 Convallaria majalis Nutrition 0.000 description 1
- 240000000798 Convallaria majalis Species 0.000 description 1
- 235000000836 Epigaea repens Nutrition 0.000 description 1
- 241001128140 Reseda Species 0.000 description 1
- 241000220317 Rosa Species 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
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000001772 cananga odorata hook. f. and thomas. oil Substances 0.000 description 1
- 229930007907 citral Natural products 0.000 description 1
- 229940043350 citral Drugs 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- WTEVQBCEXWBHNA-YFHOEESVSA-N neral Chemical compound CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
Description
fit Ο C;<") ( I ίfit Ο C ; <") (I ί
el idwi ι dah-ntov. λel idwi ι dah-ntov. λ
Ρ·· ι I Γ ΟΡ ·· ι I Γ Ο
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Bei der Untersuchung des ätherischen Öles der Blüten von Citrus bigaradia (Neroliöl) wurde ein neuer Alkohol C10 H18 O aufgefunden. Man erhält diesen neuen Alkohol, wenn man Neroliöl im Vakuum sorgfältig fraktioniert und die unter 25 mm Druck bei 120 bis 1400 C. siedende Fraktion verseift. Diese Fraktion enthält den Alkohol teils in freiem, teils in esterifiziertem Zustande. Das verseifte und gereinigte Öl wird in Benzollösung mit gleichen Teilen Phtalsäureanhydrid ι bis 1,5 Stunden erhitzt, die gebildeten sauren Phtalsäureester werden in verdünnter Sodalösung aufgenommen, durch Ausäthern von nicht angegriffenem Neroliöl befreit, mit Säuren ausgefällt und mit alkoholischem Kali verseift. Das so erhaltene Alkoholgemisch besteht im wesentlichen aus einem neuen, Nerol genannten Terpenalkohol und Geraniol.When the essential oil of the flowers of Citrus bigaradia (neroli oil) was examined, a new alcohol C 10 H 18 O was found. This new alcohol is obtained if neroli oil is carefully fractionated in vacuo and the fraction boiling at 120 to 140 ° C. under 25 mm pressure is saponified. This fraction contains the alcohol partly in the free, partly in the esterified state. The saponified and purified oil is heated in benzene solution with equal parts of phthalic anhydride for up to 1.5 hours, the acidic phthalic acid esters formed are taken up in dilute soda solution, freed from unaffected neroli oil by etherification, precipitated with acids and saponified with alcoholic potash. The alcohol mixture thus obtained consists essentially of a new terpene alcohol called nerol and geraniol.
Die Hauptmenge des Geraniols wird entfernt durch Behandlung des Alkoholgemisches mit gleichen Teilen wasserfreien Chlorcalciums bei gewöhnlicher Temperatur, wobei nur das Geraniol eine feste, in Petroläther unlösliche Chlorcalciumverbindung eingeht. Dieselbe wird mit Petroläther ausgewaschen. Das nach dem Abdestillieren des Petroläthers zurückbleibende, noch geraniolhaltige Rohprodukt wird durch 12 stündiges Erhitzen mit Phtalsäureanhydrid auf dem Wasserbade, wodurch weitere Mengen Geraniol zerstört werden, von neuem in seinen sauren Phtalsäureester übergeführt, welcher in der oben beschriebenen Weise gereinigt und verseift wird. Der so gereinigte Alkohol wird schließlich im Vakuum oder mit Wasserdampf rektifiziert. Most of the geraniol is removed by treating the alcohol mixture with equal parts of anhydrous calcium chloride at ordinary temperature, with only that Geraniol forms a solid calcium chloride that is insoluble in petroleum ether. Same is washed out with petroleum ether. That after distilling off the petroleum ether remaining crude product still containing geraniol is obtained by heating for 12 hours with phthalic anhydride on the water bath, which destroys further quantities of geraniol are converted again into its acidic phthalic acid ester, which in the above described way is cleaned and saponified. The alcohol thus purified will eventually rectified in vacuo or with steam.
Dieser neue, Nerol genannte Terpenalkohol C10 H1H O, dem noch wenig Geraniol anhaftet, ist ein wasserhelles, bei 225 bis 226° C. unter 760 mm Druck und bei 1250 C. unter 25 mm Druck unzersetzt siedendes Öl, vom spez. Gewicht 0,880 bei 150, welches optisch inaktiv ist und mit Chlorcalcium unter gewöhnlichen Bedingungen keine feste Verbindung gibt. Zwecks Herstellung von Blumengerüchen wird dieser Alkohol entweder allein oder in Mischung mit seinen Fettsäureestern in Wasser, Alkohol, ätherischen Ölen, fetten Ölen oder anderen geeigneten Lösungsmitteln mit oder ohne Zusatz von anderen Riechstoffen gelöst.This new, nerol said terpene alcohol C 10 H 1 H O, which adheres little geraniol, is a water-white, undecomposed boiling at 225-226 ° C under 760 mm pressure and at 125 0 C. under 25 mm pressure oil of specific gravity. Weight 0.880 at 15 0 , which is optically inactive and does not give a solid connection with calcium chloride under normal conditions. In order to produce floral smells, this alcohol is dissolved either alone or in a mixture with its fatty acid esters in water, alcohol, essential oils, fatty oils or other suitable solvents with or without the addition of other odoriferous substances.
Charakteristisch unterschieden vom Geraniol und Citronellol wird der Alkohol durch seinen frischen und besonders in der Verdünnung außerordentlich feinen Rosengeruch, welcher ihn in hohem Grade zur Herstellung von Blumengerüchen geeignet erscheinen läßt. Auch seine Ester der niederen Fettsäuren riechen eigentümlich aromatisch und rosenartig und sollen daher, ebenso wie der Alkohol selbst, in der Parfümerie Verwendung finden.Alcohol is characteristically differentiated from geraniol and citronellol by its fresh and particularly fine rose scent, especially when diluted, which makes it appear highly suitable for the production of floral scents. Its esters of lower fatty acids also smell peculiarly aromatic and rose-like and, like alcohol itself, should therefore be used in perfumery.
i. Darstellung eines künstlichen Rosenöles. Geraniol 39 Prozent, Citronellol 30 Prozent, Nerol 25 Prozent, Nerylacetat 2 Prozent,i. Representation of an artificial rose oil. Geraniol 39 percent, citronellol 30 percent, Nerol 25 percent, neryl acetate 2 percent,
Nonylaldehyd ι Prozent, Citral J/2 Prozent, Phenyläthylalkohol 2 1J2 Prozent.Nonyl ι percent, citral J / 2 percent, phenylethyl 2 1 J 2 percent.
2. Darstellung einer Basis für Reseda. Benzylalkohol 50 Prozent, Geraniol 10 Prozent, Linalool 15 Prozent, Linalylacetat 5 Prozent, Nerol 20 Prozent.2. Representation of a base for Reseda. Benzyl alcohol 50 percent, geraniol 10 percent, Linalool 15 percent, linalyl acetate 5 percent, nerol 20 percent.
3. Darstellung einer Basis für Maiblumen. Nerol 20 Prozent, Nerylacetat 5 Prozent, Linaloeöl 40 Prozent, Canangaöl 10 Prozent, Bergamottöl 10 Prozent, Benzylalkohol 14Y2 Prozent, Moschus '/2 Prozent.3. Representation of a base for may flowers. Nerol 20 percent, neryl acetate 5 percent, linaloe oil 40 percent, cananga oil 10 percent, bergamot oil 10 percent, benzyl alcohol 14Y 2 percent, musk / 2 percent.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE155287C true DE155287C (en) |
Family
ID=421768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT155287D Active DE155287C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE155287C (en) |
-
0
- DE DENDAT155287D patent/DE155287C/de active Active
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