CH137740A - Process for the preparation of 1,4-dioxy-benzo-thiophanthrenequinone. - Google Patents
Process for the preparation of 1,4-dioxy-benzo-thiophanthrenequinone.Info
- Publication number
- CH137740A CH137740A CH137740DA CH137740A CH 137740 A CH137740 A CH 137740A CH 137740D A CH137740D A CH 137740DA CH 137740 A CH137740 A CH 137740A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- thiophanthrenequinone
- benzo
- dioxy
- weight
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000001875 compounds Chemical group 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- -1 diacetyl compound Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
Verfahren zur Darstellung von 1.4-Diogy-benzo-thiophanthrenehinon. Es wurde gefunden, dass man hydroxy- lierte Thiophantrenchinone erhält, wenn man Thiophen-2.8-dicarbonsäuren oder deren An- hydride mit Plrenolen der Einwirkung saurer Kondensationsmittel bei höherer Temperatur unterwirft.
Die Reaktion vollzieht sich zum Beispiel nach folgender Gleichung:
EMI0001.0010
Überraschend ist, dass man in einem Arbeits gang ohne wesentliche Zersetzung der lretero- cyklischen o-Dicarbonsäuren direkt zu den Chinonkörpern gelangt. Die neuen Verbin dungen sind wertvoll als Ausgangsmate rialien für die Herstellung von Farbstoffen.
Gegenstand dieses Patentes ist ein Ver fahren zur Darstellung von 1.4-Dioxybenzo- thiophanthrerrchinon der folgenden Formel:
EMI0001.0018
dadurch gekennzeichnet, dass man Thionapthen- 2. 3-dicarbonsäureanhydrid mit Hydrochinon in Gegenwart eines sauren Kondensationsmittels umsetzt.
Die erhaltene Verbindung soll zur Herstellung von Farbstoffen Verwendung finden. Beispiel: Ein Gemisch von 10 Gewichtsteilen Thio- naphten-2.3-dicarbonsäureanhydrid und 6 Gewichtsteilen Hydrochinon wird bei 180 in eine Schmelze von 10 Gewichtsteilen Koch salz und 50 Gewichtsteilen Aluminiumchlorid unter Rühren eingetragen, die Temperatur auf 190 gesteigert und während 5 Stunden gehalten. Dann wird mit Eis und Salzsäure zersetzt und aufgearbeitet.
Das entstandene 1. 4-Dioxy-benzo-thiopharithrenchinon
EMI0002.0002
kann über die Diacetylverbindung oder durch Umkristallisieren aus Pyridin gereinigt werden. Es bildet rote Blättchen vom Schmelzpunkt 253-2540.
Process for the preparation of 1,4-diogy-benzo-thiophanthrenehinone. It has been found that hydroxylated thiophantrenequinones are obtained if thiophene-2,8-dicarboxylic acids or their anhydrides with plrenols are subjected to the action of acidic condensing agents at a higher temperature.
The reaction takes place, for example, according to the following equation:
EMI0001.0010
It is surprising that the quinone bodies can be obtained directly in one operation without substantial decomposition of the heterocyclic o-dicarboxylic acids. The new compounds are valuable as starting materials for the production of dyes.
The subject of this patent is a process for the preparation of 1,4-Dioxybenzo- thiophanthrerrquinone of the following formula:
EMI0001.0018
characterized in that thionapthene-2. 3-dicarboxylic anhydride is reacted with hydroquinone in the presence of an acidic condensing agent.
The compound obtained is said to be used for the production of dyes. Example: A mixture of 10 parts by weight of thionaphthene-2,3-dicarboxylic anhydride and 6 parts by weight of hydroquinone is added at 180 to a melt of 10 parts by weight of common salt and 50 parts by weight of aluminum chloride with stirring, the temperature is increased to 190 and held for 5 hours. Then it is decomposed and worked up with ice and hydrochloric acid.
The resulting 1,4-dioxy-benzo-thiopharithrenequinone
EMI0002.0002
can be purified via the diacetyl compound or by recrystallization from pyridine. It forms red leaflets with a melting point of 253-2540.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE137740X | 1927-09-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH137740A true CH137740A (en) | 1930-01-31 |
Family
ID=5666972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH137740D CH137740A (en) | 1927-09-07 | 1928-08-16 | Process for the preparation of 1,4-dioxy-benzo-thiophanthrenequinone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH137740A (en) |
-
1928
- 1928-08-16 CH CH137740D patent/CH137740A/en unknown
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