CH122731A - Process for the manufacture of synthetic camphor. - Google Patents
Process for the manufacture of synthetic camphor.Info
- Publication number
- CH122731A CH122731A CH122731DA CH122731A CH 122731 A CH122731 A CH 122731A CH 122731D A CH122731D A CH 122731DA CH 122731 A CH122731 A CH 122731A
- Authority
- CH
- Switzerland
- Prior art keywords
- manufacture
- mixture
- turpentine
- synthetic camphor
- reaction
- Prior art date
Links
- 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 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 229940085790 synthetic camphor Drugs 0.000 title claims description 4
- 239000000203 mixture Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- 241000779819 Syncarpia glomulifera Species 0.000 description 7
- 239000001739 pinus spp. Substances 0.000 description 7
- 229940036248 turpentine Drugs 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001247 metal acetylides Chemical class 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 4
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 3
- 229940116229 borneol Drugs 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
- 239000002253 acid Substances 0.000 description 2
- -1 bornyl oxalate Chemical compound 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001145 hydrido group Chemical group *[H] 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Procédé pour la fabrication du camphre synthétique. La revendication du brevet principal dé finit un procédé pour la fabrication du camphre synthétique, suivant lequel on chauffe un mé lange d'essence de térébenthine, d'un acide organique et d'un catalyseur liquide sous forme de composé non métallique à une tem pérature de 100 à 150 C pour faciliter et accélérer la réaction de la térébenthine avec l'acide employé, après quoi on saponifie le sel de bornyle obtenu et transforme le bornéol -séparé, par oxydation, en camphre.
Comme catalyseur on propose@dans le brevet principal des carbures halogénés, notamment un hydro- ,arbure tétrachloré.
La présente invention se rapporte à un mode de réalisation de ce procédé, dans le quel, au lieu d'employer des carbures halo- génés, on se sert comme catalyseur d'an moins un hydrocarbure aromatique non subs- 1-itué tel que le benzène, le toluène etc.
Bien que les réactions catalytiques obtenues avec un hydrocarbure aromatique non substitué tel que le benzène, le toluène etc. aient les dé fauts d'être moins rapides et de donner un bornéol moins pur, il n'en subsiste par moins que l'absence de chlore dans ces carbures présente un réel avantage vis-à-vis de l'em ploi de carbures chlorés.
La non possibilité de formation d'acide chlorhydrique évite l'iso- mération en dipentène d'une partie de la té rébenthine mise en couvre, qui est provoquée même par une trace de cet acide, d'où ré sulte un rendement supérieur en comptant sur la térébenthine mise en eeuvre. Enfin l'absence de l'acide chlorhydrique présente aussi un avantage au point de vue de l'appareillage.
Mais, les défauts inhérents à l'emploi des hydrocarbures aromatiques non substitués peuvent être corrigés en choisissant leur pro portion relative dans le mélange des composés mis en couvre, suffisamment élevée pour faire activer la réaction du mélange. Plus la pro portion de ces hydrocarbures est grande dans le mélange, plus la réaction se fait vivement et plus la quantité de térébenthine entrée en réaction est grande. Il va sans dire qu'au lieu d'un seul hydrocarbure aromatique non substitué, l'on peut employer, comme cataly- sera, un mélange d'hydrocarbures de ce genre.
L'emploi d'un mélange de ce genre petit pré- enter des avantages pour maintenir constante fa température de la réaction.
F,;rerrîpie: On chauffe ensemble à<B>110</B> C, pendant (3 à 8 heures, 1 partie d'acide oxalique sec, 3 à 4 parties de térébenthine et 8 parties d'un mélange toluérre-berrzène.
Une. fois la cuisson;'terminée, on lave avec de la soude faible pour -enlever l'acide oxa- lique non combiné.
L'huile restant composée d'un mélange de carbure terpénique et d'oxa- late de bornyle est facilement, par une rec tification fractionnée, séparée en ses consti tuants grâce à la différence de leurs points d'ébullition. L'oxalate de bornyle est sapo nifié au rnoy en de soude à la façon ordinaire et le bornéol produit est recueilli soit par en traînement à la vapeur, soit par filtration et lavage. L'acide oxalique petit être récupéré des eaux de saponification.
Avec le traitement indiqué ci-dessus le rendement se trouve notablement amélioré et petit dépasser<B>70</B> %) de la térébenthine mise en oeuvre ; l'acide oxalique non entré eu com binaison petit être récupéré intact.
Process for the manufacture of synthetic camphor. The main patent claim defines a process for the manufacture of synthetic camphor, wherein a mixture of turpentine, an organic acid and a liquid catalyst in the form of a non-metallic compound is heated to a temperature from 100 to 150 C to facilitate and accelerate the reaction of turpentine with the acid employed, after which the bornyl salt obtained is saponified and the separated borneol is transformed by oxidation into camphor.
As a catalyst, halogenated carbides, in particular a tetrachlorinated hydro-, arbide, are proposed in the main patent.
The present invention relates to an embodiment of this process, in which, instead of employing halogenated carbides, the catalyst of at least one non-substituted aromatic hydrocarbon such as benzene, toluene etc.
Although the catalytic reactions obtained with an unsubstituted aromatic hydrocarbon such as benzene, toluene etc. have the drawbacks of being slower and giving a less pure borneol, the fact remains that the absence of chlorine in these carbides has a real advantage over the use of chlorinated carbides .
The non-possibility of hydrochloric acid formation prevents the isomeration in dipentene of part of the turpentine covered, which is caused even by a trace of this acid, resulting in a higher yield by counting on the turpentine used. Finally, the absence of hydrochloric acid also presents an advantage from the point of view of the apparatus.
However, the defects inherent in the use of unsubstituted aromatic hydrocarbons can be corrected by choosing their relative proportion in the mixture of compounds covered, sufficiently high to activate the reaction of the mixture. The greater the proportion of these hydrocarbons in the mixture, the more vigorously the reaction and the greater the quantity of turpentine which has entered into the reaction. It goes without saying that instead of a single unsubstituted aromatic hydrocarbon, a mixture of such hydrocarbons may be employed as the catalyst.
The use of such a small mixture has advantages in keeping the reaction temperature constant.
F,; rerrîpie: We heat together at <B> 110 </B> C, for (3 to 8 hours, 1 part of dry oxalic acid, 3 to 4 parts of turpentine and 8 parts of a toluérre-berrzene mixture .
A. when cooking is complete, it is washed with weak soda to remove the uncombined oxalic acid.
The remaining oil composed of a mixture of terpene carbide and bornyl oxalate is easily, by fractional rectification, separated into its constituents by virtue of the difference in their boiling points. Bornyl oxalate is saponified with sodium hydroxide in the usual manner and the borneol produced is recovered either by steam dragging or by filtration and washing. Oxalic acid can be recovered from saponification water.
With the treatment indicated above, the yield is significantly improved and can exceed <B> 70 </B>%) of the turpentine used; oxalic acid not entered in the combination may be recovered intact.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR122731X | 1925-06-12 | ||
| CH98082T | 1926-06-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH122731A true CH122731A (en) | 1927-10-01 |
Family
ID=25705362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH122731D CH122731A (en) | 1925-06-12 | 1926-06-02 | Process for the manufacture of synthetic camphor. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH122731A (en) |
-
1926
- 1926-06-02 CH CH122731D patent/CH122731A/en unknown
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