DE574163C - Process for the preparation of condensation products of the anthraquinone series - Google Patents
Process for the preparation of condensation products of the anthraquinone seriesInfo
- Publication number
- DE574163C DE574163C DEI43485D DEI0043485D DE574163C DE 574163 C DE574163 C DE 574163C DE I43485 D DEI43485 D DE I43485D DE I0043485 D DEI0043485 D DE I0043485D DE 574163 C DE574163 C DE 574163C
- Authority
- DE
- Germany
- Prior art keywords
- condensation products
- preparation
- anthraquinone series
- amino
- replaced
- 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.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/48—Anthrimides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von Kondensationsprodukten der Anthrachinonreihe In dem Hauptpatent 536449, K1. I2q, ist ein Verfahren zur Darstellung von Kondensationsprodukten der Anthrachinonreihe beschrieben, welches darin besteht, daß man solche I-Amino-2-halogenanthrachinone, bei denen die Wasserstoffatome der Aminogruppe durch die Carbonylgruppen von o-Dicarbonsäuren ersetzt sind, mit α-Aminoanthrachinonen umsetzt.Process for the preparation of condensation products of the anthraquinone series In the main patent 536449, K1. I2q, is a method for the preparation of condensation products the anthraquinone series described, which consists in the fact that one such I-amino-2-halogenanthraquinones, in which the hydrogen atoms of the amino group are replaced by the carbonyl groups of o-dicarboxylic acids are replaced, reacted with α-aminoanthraquinones.
Es wurde nun gefunden, daß sich auch I-Amino-2-halogenanthrachinone, bei denen die beiden Wasserstoffatome der Aminogruppe durch die Carbonylgruppen von aliphatischen Dicarbonsäuren ersetzt sind, mit Aminen, insbesondere mit Aminoanthrachinonen, umsetzen lassen. Hierbei entstehen in nahezu quantitativer Aasbeute Verbindungen, in denen das Halogen des Ausgangsmaterials durch den Rest des verwendeten Amins ersetzt ist. Dies war nicht vorauszusehen, nachdem die Verwendung von Acylverbindungen mit einbasischen aliphatischen Säuren infolge gleichzeitiger Bildung von Oxazolen zu unbefriedigenden Resultaten führt. Analog verhalten sich Derivate und Substitutionsprodukte der erwähnten Ausgangsmaterialien.It has now been found that I-amino-2-halogenanthraquinones, where the two hydrogen atoms of the amino group through the carbonyl groups are replaced by aliphatic dicarboxylic acids, with amines, in particular with aminoanthraquinones, have it implemented. This results in almost quantitative scavenging compounds, in which the halogen of the starting material replaced by the remainder of the amine used is replaced. This was not foreseen after the use of acyl compounds with monobasic aliphatic acids as a result of the simultaneous formation of oxazoles leads to unsatisfactory results. Derivatives and substitution products behave analogously of the starting materials mentioned.
Die gemäß der Erfindung erhältlichen Kondensationsprodukte können z. B. als Ausgangsstoffe für die Darstellung von Farbstoffen Verwendung finden.The condensation products obtainable according to the invention can z. B. are used as starting materials for the representation of dyes.
Beispiel I I9 Teile I-Succinimino-2-bromanthrachinon, dargestellt z. B. durch Erhitzen von I-Amino-2-bromanthrachinon mit Bernsteinsäureanhydrid unter Zusatz geringer Mengen Eisenchlorid, werden mit II Teilen I-Aminoanthrachinon, 5 Teilen entwässertem Natriumacetat und o,2 Teilen Kupferacetat so lange in I2o Teilen siedendem Nitrobenzol erhitzt, bis praktisch kein I-Aminoanthrachinon sich mehr nachweisen läßt. Man läßt erkalten, saugt ab und entfernt aus dem Rückstand das Lösungsmittel und die anorganischen Bestandteile in der üblichen Weise. Man erhält das Reaktionsprodukt in guter Ausbeute in Form dunkelroter Kriställchen, es ist halogenfrei, löst sich in konzentrierter Schwefelsäure mit tiefblauer Farbe und stellt wahrscheinlich das I-Succinimino-2 ₧ I'-dianthrimid dar.Example I 19 parts of I-succinimino-2-bromoanthraquinone z. B. by heating I-amino-2-bromoanthraquinone with succinic anhydride under Addition of small amounts of iron chloride, with II parts of I-aminoanthraquinone, 5 Divide dehydrated sodium acetate and 0.2 parts copper acetate in I2o parts boiling nitrobenzene heated until practically no more I-aminoanthraquinone can be proven. It is allowed to cool, filtered off with suction and removed from the residue Solvent and the inorganic ingredients in the usual way. You get the reaction product in good yield in the form of dark red crystals, it is halogen-free, dissolves in concentrated sulfuric acid with a deep blue color and probably represents the I-succinimino-2 ₧ I'-dianthrimide.
Beispiel 2 38 Teile I-Succinimino-2-bromanthrachinon werden mit 25 Teilen i-Amino-3-cliloranthrachinon, i?, Teilen Natriumaeetat und o,5 Teilen Kupferacetat in 25o Teilen siedendem Nitrobenzol so lange erhitzt, bis das I-Succinimino-2-bromanthrachinon sich nicht mehr nachweisen läßt. Man läßt dann erkalten, saugt die abgeschiedenen schwer löslichen Kristalle ab und arbeitet in der üblichen Weise auf. Die so erhaltene Verbindung, wahrscheinlich das I-Succinimino-3'-chlor-2 ₧ I'-dianthrimid, löst sich in konzentrierter Schwefelsäure mit tiefblauer Farbe.Example 2 38 parts of I-succinimino-2-bromoanthraquinone are mixed with 25 Parts i-amino-3-cliloranthraquinone, i ?, parts sodium acetate and 0.5 share Copper acetate in 250 parts of boiling nitrobenzene is heated until the I-succinimino-2-bromoanthraquinone can no longer be proven. One then lets it cool down and sucks the separated off sparingly soluble crystals and works on in the usual way. The thus obtained Compound, probably the I-succinimino-3'-chloro-2 ₧ I'-dianthrimide, dissolves in concentrated sulfuric acid with a deep blue color.
In ähnlicher Weise erhält man bei Verwendung von I-Amino-3-methylanthrachinon an Stelle von I-Amino-3-chloranthrachinon das I-Succinimino-3'-methyl-2 ₧ I'-dianthrimid.Similarly, when using I-amino-3-methylanthraquinone, one obtains instead of I-amino-3-chloroanthraquinone, I-succinimino-3'-methyl-2 ₧ I'-dianthrimide.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEI43485D DE574163C (en) | 1932-01-16 | 1932-01-16 | Process for the preparation of condensation products of the anthraquinone series |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEI43485D DE574163C (en) | 1932-01-16 | 1932-01-16 | Process for the preparation of condensation products of the anthraquinone series |
Publications (1)
Publication Number | Publication Date |
---|---|
DE574163C true DE574163C (en) | 1933-04-10 |
Family
ID=7191047
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEI43485D Expired DE574163C (en) | 1932-01-16 | 1932-01-16 | Process for the preparation of condensation products of the anthraquinone series |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE574163C (en) |
-
1932
- 1932-01-16 DE DEI43485D patent/DE574163C/en not_active Expired
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