DE122851C - - Google Patents
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- Publication number
- DE122851C DE122851C DENDAT122851D DE122851DA DE122851C DE 122851 C DE122851 C DE 122851C DE NDAT122851 D DENDAT122851 D DE NDAT122851D DE 122851D A DE122851D A DE 122851DA DE 122851 C DE122851 C DE 122851C
- Authority
- DE
- Germany
- Prior art keywords
- protocatechualdehyde
- vanillin
- dimethyl sulfate
- added
- patent specification
- 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.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
PATENTAMT.PATENT OFFICE.
JV£ 122851 KLASSE 12 o.JV £ 122851 CLASS 12 o.
Die bis jetzt bekannten Methoden zur Darstellung von Vanillin durch oxydativen Abbau von Eugenol und dessen Derivaten liefern nur geringe Ausbeuten, und zwar infolge von Nebenreactionen, die sich nicht vermeiden lassen. Andererseits erhält man auch nach dem Verfahren der Patentschrift 63007, in welcher die Bildung von Vanillin durch Methylirung der Dimetallsalze des Protocatechualdehydes beschrieben ist, nur schlechte Ausbeuten. Die in der Patentschrift 63007 genannten Methylirungsmittel sind nicht geeignet, einen glatten Reactionsverlauf herbeizuführen. Es hat sich nun gezeigt, dafs sich Vanillin in weitaus besseren Ausbeuten und fast völliger Reinheit erhalten lä'fst, wenn man zur Methylirung von Protocatechualdehyd oder dessen Dimetallsalzen das Dimethylsulfat benutzt. Unterschiedlich vom Verfahren der Patentschrift 93187, in welcher die Bildung von Vanillin aus Protocatechualdehydkohlensäuremethylester beschrieben ist, wird hier also direct aus Protocatechualdehyd Vanillin erhalten.The methods known up to now for the preparation of vanillin by oxidative degradation of eugenol and its derivatives give only low yields, due to Side reactions that cannot be avoided. On the other hand, one also receives after the process of patent specification 63007, in which the formation of vanillin by methylation of the dimetallic salts of protocatechualdehyde is described, only poor yields. The methylating agents mentioned in the patent specification 63007 are not suitable, a bring about a smooth course of the reaction. It has now been shown that vanillin differs widely better yields and almost complete purity can be obtained if one for the methylation of Dimethyl sulfate uses protocatechualdehyde or its dimetallic salts. Different from Process of patent specification 93187, in which the formation of vanillin from protocatechualdehyde carbonic acid methyl ester is here thus obtained directly from protocatechualdehyde vanillin.
i. 14,2 kg Protocatechualdehyd werden in concentrirter Sodalösung gelöst und 12,6 kg Dimethylsulfat unter kräftigem Rühren zugesetzt. Nach einiger Zeit beginnt die Umsetzung, die nach mehrstündigem Erwärmen im Wasserbade beendet ist. Man säuert dann an, extrahirt mit Aether, dampft den Aether ab und zieht den Rückstand mit Chloroform aus, wobei das Vanillin in Lösung geht und durch Umkrystallisiren leicht gereinigt werden kann. Geringe Mengen von unangegriffenem Protocatechualdehyd bleiben zurück und können wieder in den Procefs zurückgeführt werden.i. 14.2 kg of protocatechualdehyde are in dissolved in concentrated soda solution and added 12.6 kg of dimethyl sulfate with vigorous stirring. After some time, the implementation begins, after several hours of warming in a water bath is finished. It is then acidified, extracted with ether, the ether is evaporated and drawn off the residue with chloroform, the vanillin going into solution and by Umkrystallisiren can be cleaned easily. Small amounts of unaffected protocatechualdehyde remain behind and can be returned to the processes.
2. Ί4,2 kg Protocatechualdehyd werden mit 11,2 kg Aetzkali in 100 kg Alkohol gelöst und 12,6 kg Dimethylsulfat hinzugegeben. Man erwärmt mehrere Stunden am Rückflufskühler, dampft den Alkohol ab, säuert an, extrahirt mit Chloroform und krystallisirt das Vanillin um.2. Ί4.2 kg of protocatechualdehyde are added 11.2 kg of caustic potash dissolved in 100 kg of alcohol and 12.6 kg of dimethyl sulfate added. Man warmed for several hours on the reflux condenser, evaporated the alcohol, acidified, extracted with it Chloroform and crystallizes the vanillin.
3. 14,2 kg Protocatechualdehyd werden mit 12,6 kg Dimethylsulfat gemischt und längere Zeit auf 1200 erhitzt. Das Reactionsproduct destillirt man im Vaccum; die Fraction zwischen 168° und 1720 bei 12 mm Druck wird umkrystallisirt.3. 14.2 kg protocatechuic be mixed with 12.6 kg of dimethyl sulfate and heated extended period to 120 0th The reaction product is distilled in a vacuum; the fraction between 168 ° and 172 0 mm at 12 pressure is recrystallized.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE122851C true DE122851C (en) |
Family
ID=391743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT122851D Active DE122851C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE122851C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2878292A (en) * | 1955-06-20 | 1959-03-17 | Crown Zellerbach Corp | Purification of bourbonal |
| FR2177693A1 (en) * | 1972-03-27 | 1973-11-09 | Hoffmann La Roche |
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0
- DE DENDAT122851D patent/DE122851C/de active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2878292A (en) * | 1955-06-20 | 1959-03-17 | Crown Zellerbach Corp | Purification of bourbonal |
| FR2177693A1 (en) * | 1972-03-27 | 1973-11-09 | Hoffmann La Roche |
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