AT49729B - Process for the oxidation of borneols and isoborneols to camphor. - Google Patents
Process for the oxidation of borneols and isoborneols to camphor.Info
- Publication number
- AT49729B AT49729B AT49729DA AT49729B AT 49729 B AT49729 B AT 49729B AT 49729D A AT49729D A AT 49729DA AT 49729 B AT49729 B AT 49729B
- Authority
- AT
- Austria
- Prior art keywords
- camphor
- oxidation
- isoborneols
- borneols
- anode
- Prior art date
Links
- 230000003647 oxidation Effects 0.000 title description 7
- 238000007254 oxidation reaction Methods 0.000 title description 7
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 title description 6
- 241000723346 Cinnamomum camphora Species 0.000 title description 6
- 229930008380 camphor Natural products 0.000 title description 6
- 229960000846 camphor Drugs 0.000 title description 6
- 238000000034 method Methods 0.000 title description 4
- 150000001637 borneol derivatives Chemical class 0.000 title description 3
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 8
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen 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
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 2
- LHXDLQBQYFFVNW-UHFFFAOYSA-N Fenchone Chemical compound C1CC2(C)C(=O)C(C)(C)C1C2 LHXDLQBQYFFVNW-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
- 229940116229 borneol Drugs 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- WQEVDHBJGNOKKO-UHFFFAOYSA-K vanadic acid Chemical compound O[V](O)(O)=O WQEVDHBJGNOKKO-UHFFFAOYSA-K 0.000 description 2
- LHXDLQBQYFFVNW-XCBNKYQSSA-N (+)-Fenchone Natural products C1C[C@]2(C)C(=O)C(C)(C)[C@H]1C2 LHXDLQBQYFFVNW-XCBNKYQSSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 229930006735 fenchone Natural products 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
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ölige Schicht in Kalkmilch gegossen und daraus der Kampfer mit Wasserdampf abgetrieben.
Der wässerige Rückstand kann zur Oxydation weiterer Borneolmengen dienen.
Das Vorfahren kann auch mit Vorteil bei Gemischen von Borneolen und Isoborneolen mit den Isofenchylalkoholen Anwendung finden, da der Isofenchylalkohol bei Gegenwart von Vanadinsäure glatt zu Fenchon oxydiert wird. Fenehon ist, da es Nitrozellulose löst, in der Zclluloidfabrikation als Beimischung zum Kampfer ohne Nachteil.
Das Verfahren lässt sich auch dahin abändern, dass Borneol und Isoborneole einer elektrolytischen Oxydation unterworfen werden, wobei Salpetersäure oder salpetersaure Salze als Elektrolyte dienen und wobei als Anode Vanadinpentoxyd verwendet wird. Hiebei ist in betracht zu ziehen,'dass das bestimmte Anodenpotential des Vanadinpentoxyds durch die spezielle Überspannung des an der Anode abgeschiedenen Sauerstoffs die gelinde Oxydation hervorruft, während bei dem ebenfalls die elektrolytische Oxydation der Borneol bezweckenden französischen Patente Nr. 387539, wie schon oben erwähnt, wegen der dabei zur Anwendung gelangenden Manganate bezw. Chromate sich ein anderes Oxydationspotential ergibt.
Bei Vanadinpentoxyd als Anoden- material ist die Stromdichte 0'06-0'6 Amp. pro c, die Temperatur die Zimmertemperatur.
Gleichzeitig kann während der Elektrolyse durch den Anodenraum Luft durehgeblasen werden.
Nach erfolgter Oxydation wird das kimpferhaltige Produkt, wie oben beschrieben, getrennt und der Kampfer mit Dampf abgetrieben.
PATENT-ANSPRÜCHE :
1. Verfahren zur Oxydation von Borneolen und Isoborneolen mit Luft oder Sauerstoff unter Verwendung von Kontaktsubstanzen zu Kampfer, dadurch gekennzeichnet, dass dieselben unter fortgesetztem Durchblascn von Sauerstoff oder Luft unter Verwendung von Vanadiaäure (Vanadiumpentoxyd) oder vnnadinsauren Salzen in Gegenwart von Salpetersäure zu Kampfer oxydiert werden, wobei die Temperatur des Reaktionsgemisches entweder durch Erhitzung oder Kühlung zwischen 30-550 ('konsta erhalten wird.
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oily layer poured into milk of lime and from it the camphor was driven off with steam.
The aqueous residue can be used to oxidize further amounts of borneol.
The procedure can also be used with advantage in mixtures of borneols and isoborneols with the isofenchyl alcohols, since the isofenchyl alcohol is oxidized to fenchone in the presence of vanadic acid. Fenehon, as it dissolves nitrocellulose, is not disadvantageous in the manufacture of clluloid as an admixture to camphor.
The process can also be modified so that borneol and isoborneol are subjected to electrolytic oxidation, with nitric acid or nitric acid salts serving as electrolytes and with vanadium pentoxide being used as the anode. It should be noted here that the specific anode potential of the vanadium pentoxide causes the mild oxidation due to the special overvoltage of the oxygen deposited at the anode, while in the case of the French patent No. 387539, which is also intended for the electrolytic oxidation of borneol, as already mentioned above, because of the resulting manganates respectively. Chromates have a different oxidation potential.
With vanadium pentoxide as the anode material, the current density is 0'06-0'6 Amp. Per c, and the temperature is room temperature.
At the same time, air can be blown through the anode compartment during electrolysis.
After oxidation has taken place, the product containing kimpfer is separated, as described above, and the camphor is driven off with steam.
PATENT CLAIMS:
1. A process for the oxidation of borneols and isoborneols with air or oxygen using contact substances to form camphor, characterized in that they are oxidized to camphor with continued bubbling of oxygen or air using vanadic acid (vanadium pentoxide) or vnadic acid salts in the presence of nitric acid , the temperature of the reaction mixture being obtained either by heating or cooling between 30-550 ('const.
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT49729T | 1908-09-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT49729B true AT49729B (en) | 1911-09-11 |
Family
ID=3570490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT49729D AT49729B (en) | 1908-09-21 | 1908-09-21 | Process for the oxidation of borneols and isoborneols to camphor. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT49729B (en) |
-
1908
- 1908-09-21 AT AT49729D patent/AT49729B/en active
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