DE456859C - Process for the preparation of 1-diazoanthraquinone-2-carboxylic acids - Google Patents

Process for the preparation of 1-diazoanthraquinone-2-carboxylic acids

Info

Publication number
DE456859C
DE456859C DEB122956D DEB0122956D DE456859C DE 456859 C DE456859 C DE 456859C DE B122956 D DEB122956 D DE B122956D DE B0122956 D DEB0122956 D DE B0122956D DE 456859 C DE456859 C DE 456859C
Authority
DE
Germany
Prior art keywords
diazoanthraquinone
carboxylic acids
preparation
acid
solution
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
Application number
DEB122956D
Other languages
German (de)
Inventor
Dr Ludwig Eifflaender
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEB122956D priority Critical patent/DE456859C/en
Application granted granted Critical
Publication of DE456859C publication Critical patent/DE456859C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von 1-Diazoanthrachinon-2-carbonsäuren. Es wurde gefunden, daß man in einfacher Weise i-Diazoanthrachinon-2-carbonsäuren gewinnen kann, wenn man die aus i-Nitroa-methylanthrachinon oder dessen Kernsubstitutionsprodukten nach dem Verfahren der Patentschrift 360 427- erhältlichen stickstoffhaltigen Anthrachinonderivate mit salpetriger Säure behandelt. Die so hergestellten Diazoverbindungen können z. B. zur Herstellung von anderen in i-Stellung substituierten Anthrachinon-2-carbonsäuren, wie z. B. der technisch wichtigen i-Chloranthrachinon-2-carbonsäure, sowie von Azofarbstoffen Verwendung finden.Process for the preparation of 1-diazoanthraquinone-2-carboxylic acids. It has been found that i-diazoanthraquinone-2-carboxylic acids can be obtained in a simple manner if the nitrogen-containing anthraquinone derivatives obtainable from i-nitroamethylanthraquinone or its core substitution products by the process of patent 360 427 are treated with nitrous acid. The diazo compounds thus prepared can, for. B. for the preparation of other i-substituted anthraquinone-2-carboxylic acids, such as. B. the technically important i-chloroanthraquinone-2-carboxylic acid, as well as azo dyes are used.

Beispiel i.Example i.

io Teile des nach Beispiel i der Patentschrift 36042,2 erhältlichen Produktes werden in ioo Teilen konzentrierter Schwefelsäure bei etwa 50° gelöst. Man läßt zu dieser Lösung die äquivalente Menge Nitrosylschwefelsäure zulaufen und verdünnt unter Kühlung mit iooTeilen Wasser, wobei zweckmäßig eine Temperatur von ¢o bis 6o° eingehalten wird.io parts of that obtainable according to example i of patent specification 36042.2 Product are dissolved in 100 parts of concentrated sulfuric acid at about 50 °. The equivalent amount of nitrosylsulfuric acid is allowed to run into this solution and diluted with cooling with 100 parts of water, expediently a temperature of ¢ o to 6o ° is observed.

Man erhält eine goldgelbe Lösung, die erforderlichenfalls zur Befreiung von geringen Mengen eines unlöslichen Niederschlages filtriert werden kann. In der Lösung befindet sich das Sulfat der i-Diazoanthrachinon-2-carbonsäure in einer Ausbeute von mehr als 8o Prozent der Theorie. .A golden yellow solution is obtained, which, if necessary, is used for liberation can be filtered from small amounts of an insoluble precipitate. In the Solution is the sulfate of i-diazoanthraquinone-2-carboxylic acid in one yield of more than 80 percent of theory. .

Beispiele. io Teile des nach Beispiel?, der Patentschrift 36042,2 erhältlichen Produktes werden in ioo Teilen konzentrierter Schwefelsäure bei etwa 50° gelöst. Man läßt zu dieser Lösung die äquivalente Menge Nitrosylschwefelsäure zulaufen und verdünnt unter Kühlung mit 2ooTeilen Wasser, wobei zweckmäßig eine Temperatur von q.o bis 6o° eingehalten wird.Examples. io parts of the example ?, the patent 36042.2 available product in 100 parts of concentrated sulfuric acid at about 50 ° solved. The equivalent amount of nitrosylsulfuric acid is added to this solution run in and diluted with cooling with 2oo parts of water, expediently one Temperature of q.o to 6o ° is maintained.

Man erhält eine rot gefärbte Lösung, die erforderlichenfalls zur Befreiung von geringen Mengen eines unlöslichen Niederschlages filtriert werden kann. In der Lösung befindet sich das Sulfat der i-Diazo-5-nitroanthrachinon-2-carbonsäure, das sich beim Abkühlen in gelbroten Blättchen abscheidet.A red colored solution is obtained, which, if necessary, is used for liberation can be filtered from small amounts of an insoluble precipitate. In the Solution is the sulfate of i-diazo-5-nitroanthraquinone-2-carboxylic acid, the separates in yellow-red leaflets on cooling.

Behandelt man die Lösung mit einer stark salzsauren Kupferchlorürlösung, so erhält man die bisher unbekannte i-Chlor-5-nitroanthrachinon-2-carbonsäure. Durch Umsetzung über das Magnesiumsalz und Umkristallisieren aus Nitrobenzol erhält man die reine Säure in fahlgelben Nadeln vom F. 301 '. Beispiel 3.If the solution is treated with a strong hydrochloric acid copper chloride solution, this gives the previously unknown i-chloro-5-nitroanthraquinone-2-carboxylic acid. By Reaction via the magnesium salt and recrystallization from nitrobenzene is obtained the pure acid in pale yellow needles from F. 301 '. Example 3.

io Teile des nach Beispiel i der Patentschrift 36o422 erhältlichen Produktes werden in ioo Teilen konzentrierter Salzsäure suspendiert, worauf man bei 6o° nitrose Gase in die Suspension einleitet. Nach Beendigung der Reaktion saugt man vom Ungelösten ab; in der Lösung ist das Chlorhydrat der i-Diazoanthrachinon-2-carbontsäure enthalten.io parts of that obtainable according to example i of patent specification 36o422 Product are suspended in 100 parts of concentrated hydrochloric acid, whereupon introduces nitrous gases into the suspension at 60 °. After the reaction is finished, it sucks one detached from the unsolved; i-diazoanthraquinone-2-carbonic acid hydrochloride is in the solution contain.

Man kann auch den Ausgangsstoff in einer wäBrigen Nitritlösung suspendieren und unter gutem Rühren konzentrierte Salzsäure zulaufen lassen. Die Behandlung mit salpetriger Säure kann auch in einem anderen geeigneten Medium erfolgen.The starting material can also be suspended in an aqueous nitrite solution and run in concentrated hydrochloric acid with thorough stirring. Treatment with nitrous acid can also be carried out in another suitable medium.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von i-Diazoanthrachinon-2-carbonsäuren, dadurch gekennzeichnet, daß man auf die nach dem Verfahren des Patents 360 q:22 aus i-Nitro-2-methylanthrachinon oder dessen Kernsubstitutionsprodukten erhältlichen stickstoffhaltigen Anthrachinonderivate salpetrige Säure oder diese entwickelnde Verbindungen einwirken lä13t.PATENT CLAIM: Process for the preparation of i-diazoanthraquinone-2-carboxylic acids, characterized in that nitrous acid or compounds developing these nitrogen-containing anthraquinone derivatives, obtainable by the process of patent 360 q: 22 from i-nitro-2-methylanthraquinone or its core substitution products, are used can have an effect.
DEB122956D 1925-11-28 1925-11-29 Process for the preparation of 1-diazoanthraquinone-2-carboxylic acids Expired DE456859C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEB122956D DE456859C (en) 1925-11-28 1925-11-29 Process for the preparation of 1-diazoanthraquinone-2-carboxylic acids

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE262119X 1925-11-28
DEB122956D DE456859C (en) 1925-11-28 1925-11-29 Process for the preparation of 1-diazoanthraquinone-2-carboxylic acids

Publications (1)

Publication Number Publication Date
DE456859C true DE456859C (en) 1928-03-02

Family

ID=25770452

Family Applications (1)

Application Number Title Priority Date Filing Date
DEB122956D Expired DE456859C (en) 1925-11-28 1925-11-29 Process for the preparation of 1-diazoanthraquinone-2-carboxylic acids

Country Status (1)

Country Link
DE (1) DE456859C (en)

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