DE2215170A1 - METHOD FOR PRODUCING M-THYMOL - Google Patents
METHOD FOR PRODUCING M-THYMOLInfo
- Publication number
- DE2215170A1 DE2215170A1 DE19722215170 DE2215170A DE2215170A1 DE 2215170 A1 DE2215170 A1 DE 2215170A1 DE 19722215170 DE19722215170 DE 19722215170 DE 2215170 A DE2215170 A DE 2215170A DE 2215170 A1 DE2215170 A1 DE 2215170A1
- Authority
- DE
- Germany
- Prior art keywords
- thymol
- production
- mixture
- dichloroethane
- isomers
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/18—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving halogen atoms of halogenated compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patentanwälte Dipl.-Ing. F. Weickmann, 221.5170 Patent attorneys Dipl.-Ing. F. Weickmann, 221.5170
Dipl.-Ing. H."Weickmann, DiPl1-PhYS. Dr. K. Fincke Dipl.-Ing. F. A."Weickmann, Dipl.-Chem. B. HuberDipl.-Ing. H. "Weickmann, DiPl 1 -PhYS. Dr. K. Fincke Dipl.-Ing. FA" Weickmann, Dipl.-Chem. B. Huber
8 MÜNCHEN 27, DEN8 MUNICH 27, DEN
MÖHLSTRASSE 22, RUFNUMMER 48 39 21/22MÖHLSTRASSE 22, NUMBER 48 39 21/22
CASE: 71.23157CASE: 71.23157
CHRYSA ε?. a.r. 1., 29, Qua i Jeän-Bap^iste Steos Fontaines-Sur-Saone / FrankreichCHRYSA ε ?. a.r. 1., 29, Qua i Jeän-Bap ^ iste Steos Fontaines-sur-Saone / France
"Verfahren zur Herstellung von m-Thymol""Process for the production of m-thymol"
Die Erfindung betrifft ein Verfahren zur Herstellung von m-Thy~ inol.The invention relates to a process for the production of m-thynol.
Gemäß einem aus der deutschen Patentschrift (Patentanmeldung P 21 01 014.0 vom 11. Januar 1971) bekannten Verfahren erhält man m-Thymol,. ausgehend von einem Thymol oder einer Mischung von Thymol-Isomer en ,indem man dieses Thymol oder diese Mischung von Thymol-Isomeren in 1,2-Dichioräthan in Anwesenheit von wasserfreiem Aluminiumchlorid erhitzt.According to one from the German patent specification (patent application P 21 01 014.0 of January 11, 1971) known method m-thymol is obtained. starting from a thymol or a mixture of thymol isomers by adding this thymol or this mixture of thymol isomers in 1,2-dichloroethane in the presence heated by anhydrous aluminum chloride.
Die Ausgangsprodukte sind somit entweder ein Thymol oder eine Mischung von isomeren Thymolen. Die Herstellung von m-Thymol, ausgehend von Thymol, ist jedoch auf grund-des hohen Preises von Thymol unwirtschaftlich. :The starting products are therefore either a thymol or a mixture of isomeric thymols. The production of m-thymol, based on thymol, however, is due to the high price of Thymol uneconomical. :
Ähnlich ist es, wenn das Ausgangsprodukt aus einer Mischung von Thymolisomeren besteht. Da die Thymolisomeren Nebenprodukte der Herstellung von Thymol sind, sind sie nur in relativ geringen Mengen erMl blich, wodurch eine Herstellung von m-Thymol in großen Mengen nicht möglich ist.It is similar when the starting product consists of a mixture of thymic isomers. Since the thymic isomers by-products of the Production of thymol, they are only available in relatively small quantities, which means that m-thymol can be produced in large quantities is not possible.
209884/1322209884/1322
Das oben genannte Verfahren gestattet somit keine wirtschaftliche Herstellung von großen Tlengen von m-Thymol. Aufgabe der Erfindung ist es daher, ein Verfahren bereitzustellen, "bei dem als Ausgangsprodukte andere Materialien als Thymol oder eine Mischung von Thymolisomeren verwendet wird.The above-mentioned process thus does not permit the economical production of large amounts of m-thymol. The object of the invention is therefore to provide a process "in which materials other than thymol or a mixture of thymol isomers are used as starting materials.
Die Erfindung betrifft somit ein Verfahren zur Herstellung von m-Thymol, das dadurch gekennzeichnet ist, daß man das Produkt der Reaktion von m-Kresol mit mindestens einem Alkylierungsroittel in Λ v2~Dichioräthan in Anwesenheit von wasserfreiein Aluminiumchlorid erhitzt.The invention thus relates to a process for the preparation of m-thymol, which is characterized in that the product of the reaction of m-cresol with at least one alkylating agent is heated in Λ v 2-dichloroethane in the presence of anhydrous aluminum chloride.
,Als Alkylierungsmittel können insbesondere Isopropylalkohol und IsopropylChlorid verwendet werden., Isopropyl alcohol and, in particular, can be used as alkylating agents Isopropyl chloride can be used.
Das folgende Beispiel soll die Erfindung weiter erläutern ohne sie jedoch zu beschränken.The following example is intended to explain the invention further without, however, restricting it.
Zu 400 g 1,2-Dichloräthan gibt raan 300 g Aluminiumchlorid und nach und nach 108 g m-Kresol. Währenddem man die Temperatur bei 500C hält, gibt man unter Rühren 60 g Isopropylalkohol zu. Nach Ablauf von 4 Stunden wird die Reaktionsmischung in Wasser gegossen, das bei niedriger Temperatur gehalten wird. Die Phenolschicht wird dekantiert, mit carbonathaltigem Wasser neutralisiert und destilliert. Die Ausbeute an m-Thymol beträgt 80 %, während das 1,2-Dichloräthan recyclisiert werden kann.300 g of aluminum chloride are added to 400 g of 1,2-dichloroethane and gradually 108 g of m-cresol. While the temperature is kept at 50 ° C., 60 g of isopropyl alcohol are added with stirring. After 4 hours, the reaction mixture is poured into water kept at low temperature. The phenolic layer is decanted, neutralized with carbonate-containing water and distilled. The m-thymol yield is 80%, while the 1,2-dichloroethane can be recycled.
Wie oben bereits angegeben, kann die Reaktion auch mit anderen Alkylierungsmitteln, insbesondere mit Isopropylchlorid durchgeführt werden,wobei jedoch die Konzentration und die Temperaturen anders liegen müssen als die in dem obigen Beispiel angegebenen.As already indicated above, the reaction can also be carried out with other alkylating agents, in particular with isopropyl chloride however, the concentration and the temperatures must be different from those given in the example above.
20988A/13Z220988A / 13Z2
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7123157A FR2142777A1 (en) | 1971-06-21 | 1971-06-21 | M-thymol prepn - from m-cresol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2215170A1 true DE2215170A1 (en) | 1973-01-25 |
Family
ID=9079289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722215170 Pending DE2215170A1 (en) | 1971-06-21 | 1972-03-28 | METHOD FOR PRODUCING M-THYMOL |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE2215170A1 (en) |
| FR (1) | FR2142777A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4731492A (en) * | 1987-03-04 | 1988-03-15 | Ethyl Corporation | Phenol alkylation process |
-
1971
- 1971-06-21 FR FR7123157A patent/FR2142777A1/en active Granted
-
1972
- 1972-03-28 DE DE19722215170 patent/DE2215170A1/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4731492A (en) * | 1987-03-04 | 1988-03-15 | Ethyl Corporation | Phenol alkylation process |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2142777B1 (en) | 1973-06-29 |
| FR2142777A1 (en) | 1973-02-02 |
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