DE624581C - Process for the preparation of anthraquinone derivatives - Google Patents

Process for the preparation of anthraquinone derivatives

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Publication number
DE624581C
DE624581C DEI49548D DEI0049548D DE624581C DE 624581 C DE624581 C DE 624581C DE I49548 D DEI49548 D DE I49548D DE I0049548 D DEI0049548 D DE I0049548D DE 624581 C DE624581 C DE 624581C
Authority
DE
Germany
Prior art keywords
preparation
anthraquinone derivatives
amino
acid
sulfuric acid
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
DEI49548D
Other languages
German (de)
Inventor
Dr Curt Bamberger
Dr Claus Weinand
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 DEI49548D priority Critical patent/DE624581C/en
Application granted granted Critical
Publication of DE624581C publication Critical patent/DE624581C/en
Expired legal-status Critical Current

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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
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
    • C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
    • C09B1/343—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated only sulfonated in the anthracene nucleus

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

Description

Verfahren zur Darstellung von Anthrachinonderivaten Es wurde gefunden, daß neue wertvolle Anthrachinonderivate erbalten werden, wenn man i Amino-4-arylaminaanthrachnon-2-sulfonsäuren in Gegenwart von konzentrierter Schwefelsäure und Formaldehyd oder einem Polymexen desselben mit nitrierenden Mitteln behandelt. Die Reaktion wird zweckmäßig bei Temperaturen von etwa 5 bis i o' durchgeführt. Der Zusatz von Farmaldehyd schützt die Aminogruppe und vermeidet Bildung von Nitramin3ver'bindungen. Dementsprechend werden nach dem neuen Verfahren einheitliche Körper erhalten. Beispielsweise erhält man für den Fall, daß .die Arylgruppe einen Benzolrestdarstellt, Farbstoffe, welche Wolle grün oder, für den Fall daß die Arylgruppe .einen Toluolrest darstellt, rotstichigblau anfärben.Process for the preparation of anthraquinone derivatives It was found that new valuable anthraquinone derivatives are inherited if one i amino-4-arylaminaanthraquinone-2-sulfonic acids in the presence of concentrated sulfuric acid and formaldehyde or a polymexen the same treated with nitrating agents. The reaction is conveniently carried out at temperatures carried out from about 5 to i o '. The addition of farmaldehyde protects the amino group and avoids the formation of nitramine compounds. Accordingly, after the new procedures to obtain uniform bodies. For example, for the In the event that the aryl group represents a benzene residue, dyes which wool green or, in the event that the aryl group represents a toluene radical, reddish-tinged blue stain.

Beispiel i 5o g i-amino-4,anilido:anthrachinOn-2-sulfonsaures Natrium werden in 36o g 96o!oiger Schwefelsäure gelöst. Der Lösung werden 2o g Trioxymethylen zugegeben. Man rührt eine halbe Stunde lang und läßt bei Temperaturen zwischen 5 bis io° i Mol Salpetersäure innerhalb, einer halben Stunde zutropfen. Nach zwei- bis dreistündigem Rühren gibt man die Mischung .auf Eis, wobei sich das Nitroderivat ausscheidet. Man saugt dann ab, wäscht neutral, löst in Wasser und salzt den erhaltenen Farbstoff mittels Kochsalzes oder Chlorkaliums bei 6o bis 70 aus. Der Farbstoff- bildet grüne Kristalle, die sich in Wasser mit grüner Farbe, in Schwefelsäure mit blauer Farbe lösen und Wolle .aus saurem Bade in grünen Tönen anfärben. Das Produkt stellt wahrscheinlich die i-Amino-4-p'-nitroanilidoanthrachinon-2-stllfonsäure dar. Die Konstitution ergibt sich daraus., daß beim Reduzieren mit Schwefelnatrium ein Aminoderivat erhalten wird, welches identisch ist mit dem bekannten Kondensationsprodukt aus i -Ainino-4-bromanthrachznon- 2 -sulf ansäure mit p-Phenylendiamin. Beispiele i-Amino -4 - P-toluidoanthrachino!n-2-sulfönsäure wird unter denselben Bedingungen und in denselben Mengenverhältnissen wie in Beispiel i angegeben mit Schwefelsäure, Ti-ioxymethylen und Salpetersäure behandelt. Die Aufarbeitung erfolgt ebenfalls wie in Beispiel i beschrieben. Der neue Farbstoff löst sich in Wasser mit rotstichigblauer, in Schwefelsäure mit grünstichigblauer Farbe und färbt Wolle aus saurem Bade rotstichigblau, während das Ausgangsprodukt grünstichgblau färbt.Example i 50 g i-amino-4, anilido: anthraquinOn-2-sulfonic acid sodium are dissolved in 36o g 96o% sulfuric acid. 20 g of trioxymethylene are added to the solution admitted. The mixture is stirred for half an hour and left at temperatures between 5 Add dropwise to 10 ° 1 mol of nitric acid within half an hour. After two- The mixture is stirred for up to three hours. On ice, the nitro derivative ruled out. It is then filtered off with suction, washed neutral, dissolved in water and the resulting salt is salted Dye using table salt or potassium chloride at 6o to 70. The dye forms green crystals, which in water turn green in color, in sulfuric acid with Loosen the blue color and dye wool from an acidic bath in green tones. The product probably represents i-amino-4-p'-nitroanilidoanthraquinone-2-stifonic acid. The constitution results from the fact that when reducing with sodium sulphide a Amino derivative is obtained which is identical to the known condensation product from i -Ainino-4-bromanthrachznon- 2-sulfanic acid with p-phenylenediamine. Examples i-Amino -4 - P-toluidoanthraquinone! n-2-sulfonic acid is produced under the same conditions and in the same proportions as given in example i with sulfuric acid, Ti-ioxymethylene and nitric acid treated. The work-up also takes place as described in example i. The new dye dissolves in water with a reddish-tinged blue, in sulfuric acid with a green-tinged blue color and dyes wool from acid baths a red-tinged blue, while the starting product turns greenish blue.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von Anthrachinonderivaten, dadurch gekennzeichnet, daß man i - Amino - 4 - arylaminaanthrachinCrn-2-sulfonsäuren in Gegenwart von konzentrierter Schwefelsäure und Formaldehyd oder einem Polymeren desselben mit nitrierenden Mitteln behandelt.PATENT CLAIM: Process for the preparation of anthraquinone derivatives, characterized in that i - amino - 4 - arylaminaanthraquinine-2-sulfonic acids in the presence of concentrated sulfuric acid and formaldehyde or a polymer the same treated with nitrating agents.
DEI49548D 1934-04-20 1934-04-20 Process for the preparation of anthraquinone derivatives Expired DE624581C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI49548D DE624581C (en) 1934-04-20 1934-04-20 Process for the preparation of anthraquinone derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI49548D DE624581C (en) 1934-04-20 1934-04-20 Process for the preparation of anthraquinone derivatives

Publications (1)

Publication Number Publication Date
DE624581C true DE624581C (en) 1936-01-24

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
DEI49548D Expired DE624581C (en) 1934-04-20 1934-04-20 Process for the preparation of anthraquinone derivatives

Country Status (1)

Country Link
DE (1) DE624581C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2485121A (en) * 1946-09-06 1949-10-18 Gen Aniline & Film Corp 1-amino-4-(nitro-2'-hydroxy)-anilinoanthraquinone-2-sulfonic acids, the salts thereof and their chrome derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2485121A (en) * 1946-09-06 1949-10-18 Gen Aniline & Film Corp 1-amino-4-(nitro-2'-hydroxy)-anilinoanthraquinone-2-sulfonic acids, the salts thereof and their chrome derivatives

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