DE564788C - Process for the preparation of derivatives of I, I'-dianthraquinonyl - Google Patents

Process for the preparation of derivatives of I, I'-dianthraquinonyl

Info

Publication number
DE564788C
DE564788C DEI42577D DEI0042577D DE564788C DE 564788 C DE564788 C DE 564788C DE I42577 D DEI42577 D DE I42577D DE I0042577 D DEI0042577 D DE I0042577D DE 564788 C DE564788 C DE 564788C
Authority
DE
Germany
Prior art keywords
dianthraquinonyl
derivatives
preparation
metals
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
Application number
DEI42577D
Other languages
German (de)
Inventor
Dr Paul Nawiasky
Dr Berthold Stein
Dr Anton Vilsmeier
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
Application granted granted Critical
Publication of DE564788C publication Critical patent/DE564788C/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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/24—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings
    • C07C225/26—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings
    • C07C225/32—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings of condensed quinone ring systems formed by at least three rings
    • C07C225/34—Amino anthraquinones
    • 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
    • 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
    • C09B1/36—Dyes with acylated amino groups
    • C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid

Landscapes

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

Description

Verfahren zur Darstellung von Derivaten des 1, 1'-Dianthrachinonyls Im Patent 558 -.74 ist ein Verfahren zur Darstellung von Derivaten des i, i'-Dianthracliinonvls beschrieben, welches darin besteht, daß man solche i-Halogen-2-aminoanthrachinone, bei denen die beiden Wasserstoffatome der Aminogruppe durch die Carbon.ylgruppen von Orthodicarbonsäuren ersetzt sind, mit -Metallen erhitzt.Process for the preparation of derivatives of 1,1'-dianthraquinonyl In patent 558-.74 there is a method for the preparation of derivatives of i, i'-dianthracliinonvls described, which consists in the fact that such i-halo-2-aminoanthraquinones, in which the two hydrogen atoms of the amino group are replaced by the carbonyl groups are replaced by orthodicarboxylic acids, heated with metals.

Es wurde nun gefunden:, daß man zu Produkten mit ähnlichen Eigenschaften gelangen kann, wenn man solche i-Halogen-2-aininoanthrachinone, bei denen die beiden Wasserstoffatome der Aminogruppe durch die Carbonylgruppen aliphatischer Dicarbonsäuren ersetzt sind, mit Metallen bei An- oder Abwesenheit von säurebindenden Mitteln oder auch Lösungs- oder Verdünnungsmitteln erhitzt. Die entstehenden Verbindungen sind im allgemeinen in organischen Mitteln schwer löslich. Sie sind vor allein wichtige Ausgangskörper für die Darstellung von Farbstoffen. Von den. -Metallen eignet sich vorzugsweise Kupfer für (las Verfahren. Beispiel io Gewichtsteile i-Chlor-2-succiniminoanthrachinon (erhältlich durch Erhitzen von Bernsteinsäureanhydrid und i-Chlor-2-aminoanthrachinon auf Zoo bis 5oo° und Absublimieren des überschüssigen Bernsteinsäureanhvdrids im Vakuum) werden mit 5 Teilen Kupferpulver gemischt und in 2o Teile siedendes Naphthalin eingetragen. Man hält dann so lange unter Rühren im Sieden, bis kein unverändertes i-Chlor-2-succiniminoanthrachinon praktisch mehr nachzuweisen ist. Man verdünnt mit Chlorbenzol, saugt ab und wäscht mit Chlorbenzol nach. Nach dem Entfernen der Beimengungen in der üblichen Weise hinterbleibt das Reaktionsprodukt in Form gelblicher Kristallkörner. Die erhaltene Verbindung, wahrscheinlich das 2 # 2'-Succinimino-i # i'-dianthrachinonyl, löst sich in konzentrierter Schwefelsäure gelb. Beim Erhitzen wird diese Lösung blaurot. Das Produkt ist chlorfrei und schmilzt oberhalb 300°.It has now been found that products with similar properties can be obtained can get if you have such i-halo-2-aininoanthraquinones, in which the two Hydrogen atoms of the amino group through the carbonyl groups of aliphatic dicarboxylic acids are replaced with metals in the presence or absence of acid-binding agents or also heated to solvents or thinners. The resulting connections are generally sparingly soluble in organic agents. You are important before alone Starting body for the representation of dyes. Of the. -Metals is suitable preferably copper for (the method. Example 10 parts by weight of i-chloro-2-succiniminoanthraquinone (obtainable by heating succinic anhydride and i-chloro-2-aminoanthraquinone on zoo up to 500 ° and subliming off the excess succinic acid anhydride in the Vacuum) are mixed with 5 parts of copper powder and 2o parts of boiling naphthalene registered. Then keep it at the boil, stirring, until nothing is unchanged i-chloro-2-succiniminoanthraquinone can be detected practically more. One dilutes with chlorobenzene, sucks off and washes with chlorobenzene. After removing the The reaction product remains in the form of yellowish additions in the usual way Crystal grains. The compound obtained, probably the 2 # 2'-succinimino-i # i'-dianthraquinonyl, dissolves yellow in concentrated sulfuric acid. When heated this solution becomes bluish red. The product is chlorine-free and melts above 300 °.

Claims (1)

PATENTANSPRUCH: Weiterbildung des Verfahrens des Patents 55847-1 zur Darstellung von Derivaten des i, i'-Dianthrachinonyls, dadurch gekennzeichnet, daß man solche i-Halogen-2-aminoanthrachinone, bei denen die beiden Wasserstoffatome der Aminogruppe durch die Carbonylgruppen aliphatischer Dicarbonsäuren ersetzt sind, mit Metallen erhitzt.PATENT CLAIM: Further development of the method of patent 55847-1 for the preparation of derivatives of i, i'-dianthraquinonyl, characterized in that i-halogen-2-aminoanthraquinones in which the two hydrogen atoms of the amino group are replaced by the carbonyl groups of aliphatic dicarboxylic acids , heated with metals.
DEI42577D 1930-12-12 1931-03-01 Process for the preparation of derivatives of I, I'-dianthraquinonyl Expired DE564788C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE1930I0027430 DE558474C (en) 1930-12-12 1930-12-12 Process for the preparation of derivatives of 1,1-dianthraquinonyl
DEI42542D DE567755C (en) 1930-12-12 1931-09-11 Process for the preparation of anthraquinone derivatives
GB32686/31A GB389568A (en) 1930-12-12 1931-11-25 Process for the manufacture and production of intermediates and dyestuffs of the anthraquinone series

Publications (1)

Publication Number Publication Date
DE564788C true DE564788C (en) 1932-11-23

Family

ID=10342479

Family Applications (3)

Application Number Title Priority Date Filing Date
DE1930I0027430 Expired DE558474C (en) 1930-12-12 1930-12-12 Process for the preparation of derivatives of 1,1-dianthraquinonyl
DEI42577D Expired DE564788C (en) 1930-12-12 1931-03-01 Process for the preparation of derivatives of I, I'-dianthraquinonyl
DEI42542D Expired DE567755C (en) 1930-12-12 1931-09-11 Process for the preparation of anthraquinone derivatives

Family Applications Before (1)

Application Number Title Priority Date Filing Date
DE1930I0027430 Expired DE558474C (en) 1930-12-12 1930-12-12 Process for the preparation of derivatives of 1,1-dianthraquinonyl

Family Applications After (1)

Application Number Title Priority Date Filing Date
DEI42542D Expired DE567755C (en) 1930-12-12 1931-09-11 Process for the preparation of anthraquinone derivatives

Country Status (3)

Country Link
DE (3) DE558474C (en)
FR (1) FR729575A (en)
GB (1) GB389568A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL113986C (en) * 1958-11-14 1900-01-01
DE1241015B (en) * 1961-02-20 1967-05-24 Durand & Huguenin Ag Process for the preparation of water-soluble leuco-sulfuric acid ester salts of the anthraquinone series

Also Published As

Publication number Publication date
DE558474C (en) 1932-09-07
DE567755C (en) 1933-01-09
GB389568A (en) 1933-03-23
FR729575A (en) 1932-07-26

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