AT39460B - Process for the preparation of camphor from borneol, isoborneol or their esters. - Google Patents
Process for the preparation of camphor from borneol, isoborneol or their esters.Info
- Publication number
- AT39460B AT39460B AT39460DA AT39460B AT 39460 B AT39460 B AT 39460B AT 39460D A AT39460D A AT 39460DA AT 39460 B AT39460 B AT 39460B
- Authority
- AT
- Austria
- Prior art keywords
- camphor
- isoborneol
- borneol
- esters
- preparation
- Prior art date
Links
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 title claims description 10
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 title claims description 10
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 title claims description 10
- 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 claims description 8
- 241000723346 Cinnamomum camphora Species 0.000 title claims description 8
- 229930008380 camphor Natural products 0.000 title claims description 8
- 229960000846 camphor Drugs 0.000 title claims description 8
- DTGKSKDOIYIVQL-MRTMQBJTSA-N Isoborneol Natural products C1C[C@@]2(C)[C@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-MRTMQBJTSA-N 0.000 title claims description 6
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 title claims description 4
- 229940116229 borneol Drugs 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 150000002148 esters Chemical class 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical class [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 1
- WWJLCYHYLZZXBE-UHFFFAOYSA-N 5-chloro-1,3-dihydroindol-2-one Chemical compound ClC1=CC=C2NC(=O)CC2=C1 WWJLCYHYLZZXBE-UHFFFAOYSA-N 0.000 description 1
- KGEKLUUHTZCSIP-UHFFFAOYSA-N Isobornyl acetate Natural products C1CC2(C)C(OC(=O)C)CC1C2(C)C KGEKLUUHTZCSIP-UHFFFAOYSA-N 0.000 description 1
- 239000001940 [(1R,4S,6R)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Substances 0.000 description 1
- ICGLOTCMOYCOTB-UHFFFAOYSA-N [Cl].[Zn] Chemical compound [Cl].[Zn] ICGLOTCMOYCOTB-UHFFFAOYSA-N 0.000 description 1
- 235000012255 calcium oxide Nutrition 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Kampfer aus Borneol, Isoborneol oder deren Estern.
Isoborneol spaltet bekanntlich leicht Wasser ab Tinter Bildung von Kamphen. Nach Bertram und Walbaum ist zur Bewirkung dieser Spaltung Kochen mit verdünnter Schwefelsäure oder Erwärmen mit C'hlorzink erforderlich. Eigene Versuche zeigten, dass Isoborneol schon beim Erhitzen auf höhere Temperaturen mit oder ohne Wasser sich in Kamphen und Wasser spaltet.
Es musste demnach als ausgeschlossen gelten, bei höherer Temperatur Isoborneol in quantitativer Ausbeute
EMI1.1
Es wurde nun beobachtet, dass sich Isol) orneol in Gegenwart von Basen sehr hoch erhitzen lässt, ohne dass Spaltung eintritt. man kann dazu entweder die betreffenden Basen in Substanz
EMI1.2
EMI1.3
<Desc/Clms Page number 2>
EMI2.1
der gebildete Kampfer wie üblich isoliert.
Beispiel 5 : 25 kg Borneol werden mit 50 kg Nickeloxyd und 25 Ay gebrannten Kalk 10 Stunden auf etwa 250 erhitzt und der gebildete Kampfer wie üblich isoliert.
EMI2.2
Beispiel 7 : 25 kg Isobornylazetat werden mit 35 kg Natron und 50 kg Wasser und 50 kg Braunstein 10 Stunden auf 2500 erhitzt und der gebildete Kampfer wie üblich isoliert.
Die Bildung von Metallalkoholaten tritt bei dem Verfahren nicht ein.
EMI2.3
<Desc / Clms Page number 1>
Process for the preparation of camphor from borneol, isoborneol or their esters.
Isoborneol is known to easily split water from Tinter Formation of camphor. According to Bertram and Walbaum, cooking with dilute sulfuric acid or heating with chlorine zinc is required to effect this split. Our own tests have shown that isoborneol splits into camphor and water when heated to higher temperatures with or without water.
It had to be excluded, therefore, isoborneol in quantitative yield at higher temperatures
EMI1.1
It has now been observed that isol) orneol can be heated to a very high temperature in the presence of bases without cleavage occurring. you can either use the bases in question in substance
EMI1.2
EMI1.3
<Desc / Clms Page number 2>
EMI2.1
the formed camphor isolated as usual.
Example 5: 25 kg of borneol are heated with 50 kg of nickel oxide and 25 ay of quick lime for 10 hours to about 250 and the camphor formed is isolated as usual.
EMI2.2
Example 7: 25 kg of isobornyl acetate are heated to 2500 for 10 hours with 35 kg of sodium bicarbonate and 50 kg of water and 50 kg of manganese dioxide and the camphor formed is isolated as usual.
The formation of metal alcoholates does not occur in the process.
EMI2.3
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1907203792D DE203792C (en) | 1907-03-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT39460B true AT39460B (en) | 1909-10-25 |
Family
ID=5778424
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT39460D AT39460B (en) | 1907-03-12 | 1908-10-02 | Process for the preparation of camphor from borneol, isoborneol or their esters. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT39460B (en) |
-
1908
- 1908-10-02 AT AT39460D patent/AT39460B/en active
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