CH212335A - Process for the production of a nitrogen-containing naphthalene derivative. - Google Patents

Process for the production of a nitrogen-containing naphthalene derivative.

Info

Publication number
CH212335A
CH212335A CH212335DA CH212335A CH 212335 A CH212335 A CH 212335A CH 212335D A CH212335D A CH 212335DA CH 212335 A CH212335 A CH 212335A
Authority
CH
Switzerland
Prior art keywords
nitrogen
production
naphthalene derivative
containing naphthalene
parts
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH212335A publication Critical patent/CH212335A/en

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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
    • C09B1/36—Dyes with acylated amino groups
    • C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
    • 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
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
    • C09B5/34—Anthraquinone acridones or thioxanthrones
    • C09B5/36—Amino acridones

Landscapes

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

Description

  

  <B>Zusatzpatent</B> zum     Hauptpatent    NT. 206427.    Verfahren zur Herstellung eines     stickstoffhaltigen        Naphthalinderivates.       Es wurde gefunden, dass ein stickstoff  haltiges     Naphthalinderivat    hergestellt werden  kann, wenn man 1     Mol        1,6-Dihalogen-2-me-          thogynaphthalin    mit 2     Mol        1-Amino-5-ben-          zoylaminoanthrachinon    umsetzt.  



  Das neue Produkt ist ein     dunkelbraunes     Pulver, das sich in konzentrierter Schwefel  säure mit     .olivgrüner,    nach     rotbraum        weeh-          selnder    Farbe löst, bei<B>300'</B> noch nicht  schmilzt und mit brauner Farbe     verküpt.     Es stellt ein wertvolles Zwischenprodukt für  die Herstellung von     Küpenfarbstoffen    dar.  



  Als     1,6-Dihalogen-2-methogynaphthalin     kann beispielsweise     1,6-Dibrom-2-methogy-          naphthalin    verwendet werden.  



  Die Umsetzung     wird    vorteilhaft durch  Erhitzen der Komponenten in     Lösungs-    oder  Verdünnungsmitteln, wie z. B.     Amylalkohol,          Nitrobenzol    oder     Naphthalin,    und zweck  mässig in Anwesenheit von     Katalysatoren,     wie Kupfer oder     Kupferverbindungen,    so  wie von säurebindenden Mitteln, durchge  führt.    <I>Beispiel:</I>  18     Teile    entwässertes     Natriumacetat    und  18 Teile wasserfreies     Natriumcarbonat    wer  den mit 480 Teilen Nitrobenzol so lange im  Sieden gehalten, bis 48 Teile Nitrobenzol ab  destilliert sind.

   Nach dem Abkühlen auf 190  bis 200       (Ölbadtemperatur)    werden 19,1       Teile        1,6-Dibrom-2-methogynaphthalin,    43,5  Teile     1-Amino-5-benzoylaminoanthrachinon     und 1,8 Teile     Kupferchlorür    zugefügt und  40     Stunden    bei 193 bis 203   gerührt. Nun  wird heiss filtriert, der Rückstand mit     Nitro-          benzol    sowie Benzol und Alkohol gewaschen  und zur Reinigung mit     verdünnter    Salzsäure  ausgekocht,     filtriert,    der Rückstand ausge  waschen und getrocknet.



  <B> Additional patent </B> to the main NT patent. 206427. Process for the production of a nitrogen-containing naphthalene derivative. It has been found that a nitrogen-containing naphthalene derivative can be prepared if 1 mole of 1,6-dihalo-2-methogynaphthalene is reacted with 2 moles of 1-amino-5-benzoylaminoanthraquinone.



  The new product is a dark brown powder that dissolves in concentrated sulfuric acid with an olive-green color that changes to reddish-brown, does not yet melt at <B> 300 '</B> and becomes brown in color. It is a valuable intermediate for the manufacture of vat dyes.



  As 1,6-dihalo-2-methogynaphthalene, for example 1,6-dibromo-2-methogynaphthalene can be used.



  The reaction is advantageously carried out by heating the components in solvents or diluents, such as. B. amyl alcohol, nitrobenzene or naphthalene, and conveniently in the presence of catalysts such as copper or copper compounds, as well as acid-binding agents, Runaway leads. <I> Example: </I> 18 parts of dehydrated sodium acetate and 18 parts of anhydrous sodium carbonate are kept boiling with 480 parts of nitrobenzene until 48 parts of nitrobenzene have distilled off.

   After cooling to 190 to 200 (oil bath temperature), 19.1 parts of 1,6-dibromo-2-methogynaphthalene, 43.5 parts of 1-amino-5-benzoylaminoanthraquinone and 1.8 parts of copper chloride are added and at 193-203 for 40 hours touched. It is then filtered hot, the residue is washed with nitrobenzene, benzene and alcohol and, for cleaning, boiled with dilute hydrochloric acid, filtered, the residue is washed out and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines stick stoffhaltigen Naphthalinderivates, dadurch gekennzeichnet, dass man 1 Mol 1,6 Dihalo- gen-2-methogynaphthalin mit 2 Mol 1-Amino- 5-benzoylaminoanthrachinon umsetzt. PATENT CLAIM: Process for the production of a nitrogen-containing naphthalene derivative, characterized in that 1 mol of 1,6-dihalogen-2-methogynaphthalene is reacted with 2 mol of 1-amino-5-benzoylaminoanthraquinone. Das neue Produkt ist ein dunkelbraunes Pulver, das sich in konzentrierter Schwefel säure mit olivgrüner, nach rotbraun wech selnder Farbe löst, bei<B>300'</B> noch nicht schmilzt und mit brauner Farbe verküpt. Es stellt ein wertvolles Zwischenprodukt für die Herstellung von Küpenfarbstoffen dar. The new product is a dark brown powder that dissolves in concentrated sulfuric acid with an olive green color that changes to reddish brown, does not yet melt at <B> 300 '</B> and becomes brown in color. It is a valuable intermediate for the manufacture of vat dyes.
CH212335D 1937-12-20 1937-12-20 Process for the production of a nitrogen-containing naphthalene derivative. CH212335A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH206427T 1937-12-20
CH212335T 1937-12-20

Publications (1)

Publication Number Publication Date
CH212335A true CH212335A (en) 1940-11-15

Family

ID=25724307

Family Applications (1)

Application Number Title Priority Date Filing Date
CH212335D CH212335A (en) 1937-12-20 1937-12-20 Process for the production of a nitrogen-containing naphthalene derivative.

Country Status (1)

Country Link
CH (1) CH212335A (en)

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