CH91088A - Method for the preparation of vanillin from acetylisoeugenol. - Google Patents
Method for the preparation of vanillin from acetylisoeugenol.Info
- Publication number
- CH91088A CH91088A CH91088DA CH91088A CH 91088 A CH91088 A CH 91088A CH 91088D A CH91088D A CH 91088DA CH 91088 A CH91088 A CH 91088A
- Authority
- CH
- Switzerland
- Prior art keywords
- vanillin
- acetylisoeugenol
- weight
- parts
- preparation
- Prior art date
Links
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 title claims description 8
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 title claims description 8
- 235000012141 vanillin Nutrition 0.000 title claims description 8
- IUSBVFZKQJGVEP-SNAWJCMRSA-N isoeugenol acetate Chemical compound COC1=CC(\C=C\C)=CC=C1OC(C)=O IUSBVFZKQJGVEP-SNAWJCMRSA-N 0.000 title claims description 7
- IUSBVFZKQJGVEP-UHFFFAOYSA-N trans-isoeugenol acetate Natural products COC1=CC(C=CC)=CC=C1OC(C)=O IUSBVFZKQJGVEP-UHFFFAOYSA-N 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 230000003647 oxidation Effects 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- VATYWCRQDJIRAI-UHFFFAOYSA-N p-aminobenzaldehyde Chemical compound NC1=CC=C(C=O)C=C1 VATYWCRQDJIRAI-UHFFFAOYSA-N 0.000 claims description 4
- -1 aromatic amino aldehydes Chemical class 0.000 claims description 3
- 238000007127 saponification reaction Methods 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- IRAKVRJJLPZVGE-UHFFFAOYSA-L acetic acid;dihydroxy(dioxo)chromium Chemical compound CC(O)=O.O[Cr](O)(=O)=O IRAKVRJJLPZVGE-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/86—Ketones containing a keto group bound to a six-membered aromatic ring containing —CHO groups
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
-
- 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
- C07C45/673—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 change of size of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von Vanillin aus Acetylisoeugenol. Im Hauptpatent ist ein Verfahren zur Darstellung von Vanillin aus Acetylisoeugenol durch. Oxydation beschrieben, welches darauf beruht, dass man die Oxydation in Gegenwart von aromatischen Aminocarbonsäuren ausführt und das Vanillin durch Verseifung herstellt.
Es hat sich nun gezeigt, dass man anstatt die Aminocarbonsäuren auch die aromatischen Aminoaldehyde verwenden kann.
Werden zum Beispiel 100 Gewichtsteile Acetylisoeugenol in Cäegenwart von l'/2 bis zwei Gewichtsteilen Para-aininobetizaldebyd, welcher vorerst durch Lösen in der zur Oxydation notwendigen Säure, z. B. in 50o/oiger Schwefelsäure, depolymerisiert werden kann, um die nötige Wasserlöslichkeit zu erreichen, oxydiert, so erreicht man, was ohne diesen Zusatz nicht möglich ist, eine nahezu voll ständige Oxydation der Propenylgruppe zur Aldehydgruppe.
<I>Beispiel:</I> 240 Gewichtsteile Natriumbichromat wer den in 1000 Gewichtsteilen Wasser gelöst und darin 120 Gewichtsteile Acetylisoeugenol in Substanz oder in einem Lösungsmittel mittelst Rührwerk fein verteilt. Zu dieser Lösung lässt man bei 80" unter beständigem Rühren eine Auflösung von zwei Gewichts teilen Par@t-amiriobetizaldehyd in 500 Ge wichtsteilen 50o/oiger Schwefelsäure langsam zulaufen.
Nach beendeter Oxydation entzieht man das gebildete Acetylvanilliii mit einem Lösungsmittel dein Reaktionsgemisch. 3Iit Hilfe von Bistilfitlösung wird es dieser Lösung entzogen und dann nach Zersetzung der Bi- sulfitlösung mit Säuren mittelst Natronlauge verseift, mit Säure abgeschieden und in sehr reiner Form gewonnen.
Man- erhält nur 12 (Gewichtsteile unver ändertes Acetylisoeugeiiol und 68 Gewichts teile Vanillin, während man ohne den Zusatz von Para-aminobenzaldehyd 48 Gewichtsteile unverändertes Aoetylisoeugeriol und nur 35 Gewichtsteile Vanillin erhält.
Bei Verwendung von wässerigen oder essigsauren Chromsäurelösungen bleibt der Effekt derselbe.
Method for the preparation of vanillin from acetylisoeugenol. The main patent is a method for the preparation of vanillin from acetylisoeugenol by. Oxidation described, which is based on the fact that the oxidation is carried out in the presence of aromatic aminocarboxylic acids and the vanillin is produced by saponification.
It has now been shown that you can use the aromatic amino aldehydes instead of the aminocarboxylic acids.
If, for example, 100 parts by weight of acetylisoeugenol are present in the presence of l '/ 2 to two parts by weight of para-aininobetizaldebyd, which is initially obtained by dissolving in the acid necessary for oxidation, e.g. B. in 50% sulfuric acid, can be depolymerized in order to achieve the necessary solubility in water, oxidized, so what is not possible without this addition, almost complete oxidation of the propenyl group to the aldehyde group.
<I> Example: </I> 240 parts by weight of sodium dichromate are dissolved in 1000 parts by weight of water and 120 parts by weight of acetylisoeugenol in bulk or in a solvent are finely distributed using a stirrer. A dissolution of two parts by weight of para-amiriobetizaldehyde in 500 parts by weight of 50% sulfuric acid is slowly run into this solution at 80 "with constant stirring.
When the oxidation has ended, the acetylvanilla formed is removed from the reaction mixture using a solvent. It is removed from this solution with the help of bistilite solution and then, after the bisulfite solution has been decomposed with acids, saponified by means of caustic soda, separated with acid and obtained in a very pure form.
Only 12 parts by weight of unchanged acetylisoeugeriol and 68 parts by weight of vanillin are obtained, while 48 parts by weight of unchanged aoetylisoeugeriol and only 35 parts by weight of vanillin are obtained without the addition of para-aminobenzaldehyde.
When using aqueous or acetic acid chromic acid solutions, the effect remains the same.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH91088T | 1919-09-09 | ||
| CH89053T | 1919-09-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH91088A true CH91088A (en) | 1921-10-17 |
Family
ID=25703927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH91088D CH91088A (en) | 1919-09-09 | 1919-09-09 | Method for the preparation of vanillin from acetylisoeugenol. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH91088A (en) |
-
1919
- 1919-09-09 CH CH91088D patent/CH91088A/en unknown
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