CH143210A - Process for the preparation of a condensation product of the benzanthrone series. - Google Patents
Process for the preparation of a condensation product of the benzanthrone series.Info
- Publication number
- CH143210A CH143210A CH143210DA CH143210A CH 143210 A CH143210 A CH 143210A CH 143210D A CH143210D A CH 143210DA CH 143210 A CH143210 A CH 143210A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- condensation product
- yellow
- benzanthrone
- mixture
- Prior art date
Links
- HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical class C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 title claims description 8
- 239000007859 condensation product Substances 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 239000000984 vat dye Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- 239000003085 diluting agent Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Kondensationsproduktes der Benzanthronreihe. Im Hauptpatent ist ein Verfahren zur Darstellung eines neuen Kondensationspro duktes der Benzanthronreihe beschrieben, bei dem ein Gemisch von Benzanthron und Aceton mit alkalischen Kondensationsmitteln behandelt wird.
Es wurde nun gefunden, dass man eben falls ein wertvolles Kondensationsprodukt der Benzanthronreihe erhalten kann, wenn man ein Gemisch von Benzanthron und Acetonitril mit alkalischen Kondensationsmitteln be handelt. Man kann die Reaktion in Ver dünnungsmitteln, wie Benzol, Mono-, Di- und Trichlorbenzol, Pyridin usw., erfolgen lassen; sie lässt sich aber auch ohne Verdünnungs mittel, zum Beispiel mit einem Überschuss des angewandten Acetonitrils, ausführen.
Man kann unter Luftausschluss, zum Beispiel in einer Stickstoffatmosphäre, aber auch unter Luftzutritt, gewünschtenfalls auch in einem Luftstrom, arbeiten. Die Kondensation ver- läuft im allgemeinen glatt und mit guter Ausbeute.
Das Kondensationsprodukt kristallisiert in derben gelben Nadeln vom Fp. 19z-194 , gibt mit Alkalien salzartige Verbindungen, die sich in Alkohol intensiv gelbrot lösen, und löst sich in konzentrierter Schwefeläure orange mit gelbgrüner Fluoreszenz. Es soll als Zwischenprodukt bei der Darstellung von Küpenfarbstoffen verwendet werden.
Beispiel: In ein Gemisch von 100 Teilen Benzan- thron, 300 Teilen gepulvertem Ätzkali und 400 Teilen wasserfreiem Pyridin lässt man in einer Stickstoffatmosphäre bei zirka 25 bis 30 unter Rühren 100 Teile Acetonitril ein tropfen, hierauf rührt man noch zirka 4-5 Stunden lang weiter. Die Farbe des Gemisches geht von braungelb über grüngelb nach rot stichig violett über. Das Reaktionsgemisch wird alsdann mit zirka 1200 Teilen Alkohol verdünnt und die nunmehr gelbrote Lösung in ein Gemisch von überschüssiger Salzsäure und Eis eingetragen.
Das zunächst harzige Reaktionprodukt wird nach einiger Zeit fest und kann, nötigenfalls nach Behandlung mit Aceton zur Entfernung harziger Verunreini gungen, noch aus Benzol oder Eisessig um kristallisiert werden.
Process for the preparation of a condensation product of the benzanthrone series. The main patent describes a process for the preparation of a new condensation product of the benzanthrone series, in which a mixture of benzanthrone and acetone is treated with alkaline condensing agents.
It has now been found that a valuable condensation product of the benzanthrone series can also be obtained if a mixture of benzanthrone and acetonitrile is treated with alkaline condensing agents. The reaction can be carried out in diluents such as benzene, mono-, di- and trichlorobenzene, pyridine, etc .; but it can also be carried out without a diluent, for example with an excess of the acetonitrile used.
It is possible to work with exclusion of air, for example in a nitrogen atmosphere, but also with access to air, if desired also in an air stream. The condensation generally proceeds smoothly and with good yield.
The condensation product crystallizes in coarse yellow needles of melting point 19z-194, gives salt-like compounds with alkalis, which dissolve in alcohol in an intensely yellow-red color, and dissolves in concentrated sulfuric acid in orange with yellow-green fluorescence. It is intended to be used as an intermediate in the preparation of vat dyes.
Example: 100 parts of acetonitrile are added dropwise to a mixture of 100 parts of benzanthrone, 300 parts of powdered caustic potash and 400 parts of anhydrous pyridine in a nitrogen atmosphere at about 25 to 30 hours while stirring, and stirring is continued for about 4-5 hours . The color of the mixture changes from brownish-yellow to green-yellow to red and tinged violet. The reaction mixture is then diluted with about 1200 parts of alcohol and the now yellow-red solution is added to a mixture of excess hydrochloric acid and ice.
The initially resinous reaction product solidifies after a while and can, if necessary after treatment with acetone to remove resinous impurities, be crystallized from benzene or glacial acetic acid.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE143210X | 1928-02-21 | ||
| CH141309T | 1928-10-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH143210A true CH143210A (en) | 1930-10-31 |
Family
ID=25713659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH143210D CH143210A (en) | 1928-02-21 | 1928-12-28 | Process for the preparation of a condensation product of the benzanthrone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH143210A (en) |
-
1928
- 1928-12-28 CH CH143210D patent/CH143210A/en unknown
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