CH212334A - 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
CH212334A
CH212334A CH212334DA CH212334A CH 212334 A CH212334 A CH 212334A CH 212334D A CH212334D A CH 212334DA CH 212334 A CH212334 A CH 212334A
Authority
CH
Switzerland
Prior art keywords
nitrogen
mol
naphthalene derivative
production
containing naphthalene
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 CH212334A publication Critical patent/CH212334A/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16Amino-anthraquinones
    • C09B1/20Preparation from starting materials already containing the anthracene nucleus
    • C09B1/36Dyes with acylated amino groups
    • C09B1/42Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/24Dyes 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
    • C09B5/34Anthraquinone acridones or thioxanthrones
    • C09B5/36Amino acridones

Landscapes

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

Description

  

  Verfahren zur Herstellung eines stickstoffhaltigen     Naphthalinderivates.       Es wurde gefunden, dass ein stickstoff  haltiges     Naphthalinderivat    hergestellt werden  kann,     wenn    man 1     Mol        2,6-Dihalogennaph-          thalin    gleichzeitig mit 1     Mol        1-Amino-5-ben-          zoylaminoanthrachinon    und mit 1     Mol        1-          Amino-4-benzoylaminoanthrachinon    umsetzt.  



  Das neue Produkt ist ein     braunschwarzes,     kristallines Pulver, das bei<B>300'</B> noch nicht       schmilzt,    sich in konzentrierter Schwefelsäure  mit     grüner    Farbe löst und nicht     verküpt.    Es  stellt ein wertvolles Zwischenprodukt für die  Herstellung von     Küpenfarbstoffen    dar.  



  Als     2,6-Dihalogennaphthalin    kann bei  spielsweise     2,6-Dibromnaphthalin    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,    sowie  von     säurebindenden    Mitteln,     durchgeführt.     <I>Beispiel:

  </I>  4,3 Teile     2,6-Dibromnaphthalin    werden  mit 5,3 Teilen 1 -     Amino    - 5 -     benzoylamino-          anthrachinon,    5,3 Teilen 1-Amino-4-benzoyl-         aminoanthrachinon,    0,4 Teilen     Kupferchlorür,     4,5 Teilen wasserfreiem     Natriumcarbonat    und  4,5     Teilen        entwässertem        Natriumacetat    in 90  Teilen trockenem Nitrobenzol unter Rühren  zum Sieden erhitzt.

   Nach beendigter Reak  tion wird heiss     filtriert,    der Rückstand mit  Nitrobenzol, Benzol     und    Alkohol gewaschen,       mit        verdünnter    Salzsäure ausgekocht, fil  triert, gewaschen und getrocknet.



  Process for the production of a nitrogen-containing naphthalene derivative. It has been found that a nitrogen-containing naphthalene derivative can be produced if 1 mol of 2,6-dihalogenaphthalene is reacted simultaneously with 1 mol of 1-amino-5-benzoylaminoanthraquinone and with 1 mol of 1-amino-4-benzoylaminoanthraquinone.



  The new product is a brown-black, crystalline powder that does not melt at <B> 300 '</B>, dissolves in concentrated sulfuric acid with a green color and does not condense. It is a valuable intermediate for the manufacture of vat dyes.



  2,6-Dibromonaphthalene, for example, can be used as 2,6-dihalonaphthalene.



  The reaction is advantageously carried out by heating the components in solvents or diluents, such as. B. amyl alcohol, nitrobenzene or naphthalene, and conveniently carried out in the presence of catalysts such as copper or copper compounds, as well as acid-binding agents. <I> example:

  4.3 parts of 2,6-dibromonaphthalene are mixed with 5.3 parts of 1-amino-5-benzoylamino-anthraquinone, 5.3 parts of 1-amino-4-benzoyl-aminoanthraquinone, 0.4 parts of copper chloride, 4 , 5 parts of anhydrous sodium carbonate and 4.5 parts of dehydrated sodium acetate in 90 parts of dry nitrobenzene heated to the boil with stirring.

   After the reaction has ended, the mixture is filtered hot, the residue is washed with nitrobenzene, benzene and alcohol, boiled with dilute hydrochloric acid, filtered, washed and dried.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines stick stoffhaltigen Naphthalinderivates, dadurch gekennzeichnet, dass man 1 Mol 2,6-Dihalo- gennaphthalin gleichzeitig mit 1 Mol 1 Amina-5-benzoylaminoanthrachinon und mit 1 Mol 1-Amino-4-benzoylaminoanthrachinon umsetzt. PATENT CLAIM: A process for producing a nitrogen-containing naphthalene derivative, characterized in that 1 mol of 2,6-dihalogen naphthalene is reacted simultaneously with 1 mol of 1 amine-5-benzoylaminoanthraquinone and with 1 mol of 1-amino-4-benzoylaminoanthraquinone. Das neue Produkt ist ein braunschwarzes, kristallines Pulver, das bei 300 noch nicht schmilzt, sich in konzentrierter Schwefel säure mit grüner Farbe löst und nicht ver- küpt. Es stellt ein wertvolles Zwischen produkt für die Herstellung von Küpenfarb- stoffen dar. The new product is a brown-black, crystalline powder that does not melt at 300, dissolves in concentrated sulfuric acid with a green color and does not condense. It is a valuable intermediate product for the manufacture of vat dyes.
CH212334D 1937-12-20 1937-12-20 Process for the production of a nitrogen-containing naphthalene derivative. CH212334A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH212334T 1937-12-20
CH206427T 1937-12-20

Publications (1)

Publication Number Publication Date
CH212334A true CH212334A (en) 1940-11-15

Family

ID=25724306

Family Applications (1)

Application Number Title Priority Date Filing Date
CH212334D CH212334A (en) 1937-12-20 1937-12-20 Process for the production of a nitrogen-containing naphthalene derivative.

Country Status (1)

Country Link
CH (1) CH212334A (en)

Similar Documents

Publication Publication Date Title
CH212334A (en) Process for the production of a nitrogen-containing naphthalene derivative.
CH212332A (en) Process for the production of a nitrogen-containing naphthalene derivative.
CH212340A (en) Process for the production of a nitrogen-containing naphthalene derivative.
CH213188A (en) Process for the production of a nitrogen-containing naphthalene derivative.
CH212343A (en) Process for the preparation of a nitrogen-containing naphthalene derivative.
CH212333A (en) Process for the production of a nitrogen-containing naphthalene derivative.
CH213187A (en) Process for the production of a nitrogen-containing naphthalene derivative.
CH211046A (en) Process for the production of a fluoranthene derivative.
CH211044A (en) Process for the production of a fluoranthene derivative.
CH212331A (en) Process for the production of a nitrogen-containing naphthalene derivative.
CH211429A (en) Process for the production of a chrysene derivative.
CH208953A (en) Process for the production of a fluoranthene derivative.
CH212335A (en) Process for the production of a nitrogen-containing naphthalene derivative.
CH211045A (en) Process for the production of a fluoranthene derivative.
CH211425A (en) Process for the production of a chrysene derivative.
CH211422A (en) Process for the production of a chrysene derivative.
CH211047A (en) Process for the production of a fluoranthene derivative.
CH211048A (en) Process for the production of a fluoranthene derivative.
CH211428A (en) Process for the production of a chrysene derivative.
CH211423A (en) Process for the production of a chrysene derivative.
CH206427A (en) Process for the production of a nitrogen-containing naphthalene derivative.
CH211049A (en) Process for the production of a fluoranthene derivative.
CH257947A (en) Process for the production of a vat dye.
CH212116A (en) Process for the production of a chrysene derivative.
CH211426A (en) Process for the production of a chrysene derivative.