CH122242A - Process for the preparation of Bz-2-methylbenzanthrone. - Google Patents
Process for the preparation of Bz-2-methylbenzanthrone.Info
- Publication number
- CH122242A CH122242A CH122242DA CH122242A CH 122242 A CH122242 A CH 122242A CH 122242D A CH122242D A CH 122242DA CH 122242 A CH122242 A CH 122242A
- Authority
- CH
- Switzerland
- Prior art keywords
- methylbenzanthrone
- preparation
- aluminum chloride
- benzanthrone
- crotonaldehyde
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical compound C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 claims description 3
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 claims description 3
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 claims description 3
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000446 fuel Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- ZSFZQNSWHYVSDP-UHFFFAOYSA-G dialuminum;sodium;heptachloride Chemical compound [Na+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-] ZSFZQNSWHYVSDP-UHFFFAOYSA-G 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von Bz-2-IETethylbenzanthron. Es wurde nun gefunden, dass man zu Bz-2-Methylbenzanthron gelangt, wenn man aus Anthron und Crotonaldehyd unter An wendung eines Kondensationsmittels ein Zwischenprodukt bildet und dieses ohne Ver wendung oxydierender Stoffe mit Aluminium chlorid behandelt.
Das entstehende Bz-2-Methylbenzanthron ist ein wichtiges Zwischenprodukt zur Her stellung von Farbstoffen. Nach dem Um kristallisieren aus Methylalkohol ist das Produkt rein. Es bildet gelbe Nadeln vom Schmelzpuunkt 168 .
Die Lösungsfarbe und Fluoreszenz in konzentrierter Schwefelsäure entspricht der des gewöhnlichen Benzanthrons.- Beispiel: 10 Teile des nach Beispiel 3 des Haupt patents erhaltenen Kondensationszwischen produktes aus Anthron und Crotonaldehyd werden mit 70 Teilen Aluminiumchlorid oder Natrium-Aluminiumchlorid innig gemischt und kurze Zeit langsam ansteigend auf 80-150 erhitzt. Man zersetzt die Schmelze mit Salz säure und Wasser, zieht sie mit Salzsäure gründlich aus und trocknet. Hierauf wird mit Sprit ausgezogen und die Lösung mit Wasser gefällt.
Nach dem Entfernen beige mengten Anthrachinons durch Ausküpen de stilliert man den Rückstand, wie in Beispiel 1 des Hauptpatents angegeben, mit überhitztem Wasserdampf und erhält nach dem Umlösen aus Sprit-Benzol ein Bz-2-Methylbenzanthron vom Scbmelzpunkt 168 , dessen Lösungsfarbe der des gewöhnlichen Benzanthrons entspricht.
Process for the preparation of Bz-2-IETethylbenzanthrone. It has now been found that Bz-2-methylbenzanthrone is obtained if an intermediate product is formed from anthrone and crotonaldehyde using a condensing agent and this is treated with aluminum chloride without using oxidizing substances.
The resulting Bz-2-methylbenzanthrone is an important intermediate for the manufacture of dyes. After recrystallizing from methyl alcohol, the product is pure. It forms yellow needles with a melting point of 168.
The solution color and fluorescence in concentrated sulfuric acid corresponds to that of the usual benzanthrone.- Example: 10 parts of the intermediate condensation product of anthrone and crotonaldehyde obtained according to Example 3 of the main patent are intimately mixed with 70 parts of aluminum chloride or sodium aluminum chloride and slowly increasing to 80 for a short time -150 heated. The melt is decomposed with hydrochloric acid and water, extracted thoroughly with hydrochloric acid and dried. Then it is extracted with fuel and the solution is precipitated with water.
After removing the added anthraquinone by exhaustion, the residue is distilled, as indicated in Example 1 of the main patent, with superheated steam and, after dissolving from fuel benzene, a Bz-2-methylbenzanthrone melting point 168, the solution color of which is that of the ordinary benzanthrone corresponds.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH120516T | 1925-12-03 | ||
| DE122242X | 1929-03-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH122242A true CH122242A (en) | 1927-09-01 |
Family
ID=25709451
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH122242D CH122242A (en) | 1925-12-03 | 1925-12-03 | Process for the preparation of Bz-2-methylbenzanthrone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH122242A (en) |
-
1925
- 1925-12-03 CH CH122242D patent/CH122242A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH122242A (en) | Process for the preparation of Bz-2-methylbenzanthrone. | |
| DE575362C (en) | Process for the preparation of acidic wool dyes of the anthraquinone series | |
| DE579393C (en) | Process for the preparation of a condensation product from two amines | |
| DE515680C (en) | Process for the preparation of pyrazolanthrone-2-carboxylic acid | |
| DE330550C (en) | Process for the preparation of methylene anthraquinone and its substitution products | |
| CH157657A (en) | Process for the production of a new condensation product. | |
| DE523626C (en) | Process for the preparation of brown Kuepen dyes of the anthraquinone series | |
| CH116078A (en) | Process for the preparation of a vat dye of the anthraquinone series. | |
| CH144304A (en) | Process for the production of a yellow-orange vat dye. | |
| CH112540A (en) | Process for the preparation of a condensation product of the anthraquinone series. | |
| CH108198A (en) | Process for the production of a new intermediate product in the tar color industry. | |
| CH128117A (en) | Process for the preparation of Bz1-ethyl-Bz2-methylbenzanthrone. | |
| CH106452A (en) | Process for the production of a new indigoid dye. | |
| CH128127A (en) | Process for the preparation of Bz1-oxybenzanthrone. | |
| CH104931A (en) | Process for the production of an indigoid dye. | |
| CH106435A (en) | Process for the production of a new indigoid dye. | |
| CH120257A (en) | Process for the preparation of a new oxynaphthalene carboxylic acid. | |
| CH107340A (en) | Process for the production of a new vat dye. | |
| CH106434A (en) | Process for the production of a new indigoid dye. | |
| CH133704A (en) | Process for the preparation of a new product which can be used as a dye. | |
| CH149697A (en) | Process for the preparation of 6'-chloro-6-methylnaphthalene tetrahydride-1.2.3.4. | |
| CH119148A (en) | Process for the preparation of an anthracene derivative. | |
| CH159851A (en) | Process for the preparation of carbazole-2,7-disulfonic acid. | |
| CH197477A (en) | Process for the preparation of a polymethine dye. | |
| CH143236A (en) | Process for the preparation of a compound with a hydrogenated ring system. |