[go: up one dir, main page]

DE478739C - Process for the production of derivatives of the alkylaminoanthraquinones - Google Patents

Process for the production of derivatives of the alkylaminoanthraquinones

Info

Publication number
DE478739C
DE478739C DEB134745D DEB0134745D DE478739C DE 478739 C DE478739 C DE 478739C DE B134745 D DEB134745 D DE B134745D DE B0134745 D DEB0134745 D DE B0134745D DE 478739 C DE478739 C DE 478739C
Authority
DE
Germany
Prior art keywords
derivatives
production
alkylaminoanthraquinones
sulfuric acid
reaction
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
DEB134745D
Other languages
German (de)
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.)
Imperial Chemical Industries Ltd
Original Assignee
British Dyestuffs Corp Ltd
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 British Dyestuffs Corp Ltd filed Critical British Dyestuffs Corp Ltd
Application granted granted Critical
Publication of DE478739C publication Critical patent/DE478739C/en
Expired legal-status Critical Current

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
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
    • C09B1/285—Dyes with no other substituents than the amino groups

Landscapes

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

Description

Die Erfindung betrifft die Herstellung von Anthrachinonderivaten, welche wertvolle Zwischenprodukte und Farbstoffe für Acetatseide sind. Es wurde gefunden, daß durch Erhitzen von i-4-Dialkylaminoanthrachinonen mit konzentrierter oder rauchender Schwefelsäure oder Schwefelsäuremonohydrat bei ziemlich hohen Temperaturen von etwa 150 bis 220 ° C eine Reaktion stattfindet, von welcher man zuerst annahm, daß sie in der Ausschaltung einer oder mehrerer Alkylaminogruppen und Ersatz derselben durch Hydroxylgruppen bestand. Indessen zeigte eine weitere Untersuchung, daß die Reaktion ein Verfahren zur Entalkylisierung ist, indem eine Alkylgruppe von jeder Dimethylaminogruppe verlorengeht.The invention relates to the production of anthraquinone derivatives, which are valuable intermediates and dyes for acetate silk. It has been found that by heating i-4-dialkylaminoanthraquinones with concentrated or fuming sulfuric acid or sulfuric acid monohydrate at fairly high temperatures of about 150 to 220 ° C Reaction takes place, which was at first thought to result in the elimination of an or several alkylamino groups and replacement of these with hydroxyl groups. In the meantime Further investigation showed that the reaction was a process for dealkylization is in that one alkyl group is lost from each dimethylamino group.

-CH3
CH3 -CH 3
CH 3

-NiT-NiT

CH3-I-CH3SO4H.CH 3 -I-CH 3 SO 4 H.

SO4H
HSO 4 H
H

Bei der Herstellung von Dialkylaminoanthrachinonen aus Leukodialkylaminoanthrachinonen durch Oxydation in Schwefelsäure, d. h. Umwandlung von Leuko-i'4-dimethylaminoanthrachinonen zu i^-Dimethylaminoanthrachinonen, kann das neue Verfahren ohne Abscheidung des Dialkylaminoanthrachinons ausgeführt werden, beispielsweise bloß durch Regelung der Säurestärke des Gemisches und weitere Erhitzung bei geeigneter Temperatur.In the production of dialkylaminoanthraquinones from leuco dialkylaminoanthraquinones by oxidation in sulfuric acid, d. H. Conversion of leuco-14-dimethylaminoanthraquinones to i ^ -Dimethylaminoanthraquinones, the new process can be used without deposition of the Dialkylaminoanthraquinones are carried out, for example, merely by controlling the acid strength of the mixture and further heating at a suitable temperature.

Beispielexample

10 Gewichtsteile von i-4-Dimethylaminoanthrachinon werden mit 100 Gewichtsteilen Schwefelsäure (100 %) gemischt und unter Umrühren eine Stunde lang bei 180 bis 220 ° C erhitzt. Die Farbe des Reaktionsgemisches geht von braun zu blau über, und die Reaktion wird als beendigt angesehen, wenn eine Probe bei Verdünnung mit einem Gemisch von Schwefelsäure und Borsäure eine Purpurfärbung erhält. Das Produkt wird aus dem Reaktionsgemisch durch Zusatz von 2000 Gewichtsteilen Wasser abgetrennt, abfiltriert und dann säurefrei" gewaschen. Wenn man 0,5 Gewichtsteile Borsäure zum ursprünglichen Gemisch hinzusetzt, so kann man die Reaktion bei 130 ° C durchführen.10 parts by weight of i-4-dimethylaminoanthraquinone are mixed with 100 parts by weight of sulfuric acid (100%) and under Stir heated at 180 to 220 ° C for one hour. The color of the reaction mixture goes from brown to blue over, and the reaction is considered complete when a sample is present Dilution with a mixture of sulfuric acid and boric acid gives a purple color. The product is made from the reaction mixture by adding 2000 parts by weight of water separated off, filtered off and then washed acid-free ". If you add 0.5 parts by weight of boric acid added to the original mixture, the reaction can be carried out at 130.degree.

Das Produkt färbt Acetatseide hellblauviolett. Es kann aus Alkohol umkristallisiert werden und ist in heißer verdünnter Natronlauge mit purpurner Farbe löslich.The product dyes acetate silk light blue-violet. It can be recrystallized from alcohol and is soluble in hot, dilute caustic soda with a purple color.

Mit iooprozentiger Schwefelsäure gibt es eine braune Färbung, die bei Zusatz von Borsäure blaurot wird.With 100 percent sulfuric acid there is a brown color which turns bluish red when boric acid is added.

Claims (1)

Patentanspruch:Claim: Verfahren zur Herstellung von Abkömmlingen der Alkylaminoanthrachinone, dadurch gekennzeichnet, daß man 1 · 4-Di-" (alkyl- So amino-) anthrachinone mit hochkonzentrierter Schwefelsäure in An- oder Abwesenheit von Borsäure auf Temperaturen über 150 °, vorteilhaft über 180 bis 220 °, erhitzt.Process for the preparation of derivatives of the alkylaminoanthraquinones, thereby characterized in that 1 · 4-Di- "(alkyl So amino) anthraquinones with highly concentrated Sulfuric acid in the presence or absence of boric acid to temperatures above 150 °, advantageously above 180 to 220 °, heated.
DEB134745D 1926-12-13 1927-12-08 Process for the production of derivatives of the alkylaminoanthraquinones Expired DE478739C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3156726A GB291814A (en) 1926-12-13 1926-12-13 Manufacture of anthraquinone derivatives

Publications (1)

Publication Number Publication Date
DE478739C true DE478739C (en) 1929-07-03

Family

ID=10325044

Family Applications (1)

Application Number Title Priority Date Filing Date
DEB134745D Expired DE478739C (en) 1926-12-13 1927-12-08 Process for the production of derivatives of the alkylaminoanthraquinones

Country Status (3)

Country Link
DE (1) DE478739C (en)
FR (1) FR645999A (en)
GB (1) GB291814A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4096176A (en) 1972-12-12 1978-06-20 Sterling Drug Inc. Benzoylbenzoic acids

Also Published As

Publication number Publication date
FR645999A (en) 1928-11-06
GB291814A (en) 1928-06-13

Similar Documents

Publication Publication Date Title
DE478739C (en) Process for the production of derivatives of the alkylaminoanthraquinones
DE895041C (en) Process for the preparation of triphenylmethane dyes
DE451495C (en) Process for the production of Kuepen dyes of the anthraquinone series
DE1079762B (en) Process for the production of Kuepen dyes of the thiazole and oxazole series
DE581161C (en) Process for the production of water-soluble dyes of the anthraquinone series
DE638150C (en) Process for the preparation of dyes of the anthraquinone series
DE598154C (en) Process for the production of nitrogen-containing anthraquinone derivatives
US1898750A (en) Manufacture of anthraquinone derivatives
DE501232C (en) Process for the preparation of dyes of the anthraquinone series
DE402643C (en) Process for the preparation of related dyes
US1932594A (en) Condensation products of the anthraquinone series
DE490812C (en) Process for the production of 1íñ4-diaminoanthraquinone, its offshoots and substitution products
DE1164003B (en) Process for the preparation of anthraquinone dyes
DE495900C (en) Process for the preparation of azine dyes
DE638834C (en) Process for the preparation of 1-alkylamino-4-oxalkylaminoanthraquinones
DE491878C (en) Process for the preparation of 2-chloro-1, 4-dioxyanthraquinones
DE481617C (en) Process for the preparation of unsulfonated arylaminoanthraquinones
DE561494C (en) Process for the representation of dyes
DE620837C (en) Process for the production of colored lakes of the anthraquinone series
DE596340C (en) Process for the representation of dyes
DE568034C (en) Process for the production of condensation products
DE948347C (en) Process for the preparation of dyes of the dioxazine series
DE628232C (en) Process for the preparation of anthraquinone derivatives
DE1098651B (en) Process for the production of acidic chromating dyes of the antraquinone series
DE454427C (en) Process for the preparation of Kuepen dyes