CH212331A - 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
CH212331A
CH212331A CH212331DA CH212331A CH 212331 A CH212331 A CH 212331A CH 212331D A CH212331D A CH 212331DA CH 212331 A CH212331 A CH 212331A
Authority
CH
Switzerland
Prior art keywords
production
nitrogen
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 CH212331A publication Critical patent/CH212331A/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

  

  Verfahren zur Herstellung eines stickstoffhaltigen     Naphthalinderivates.       Es wurde gefunden, dass     ein    stickstoff  haltiges     Naphthalinderivat    hergestellt wer  den kann, wenn man 1     Mol        2,6-Dihalogen-          naphthalin    mit 2     Mol        1-Amino-4-benzoyl-          aminoanthrachinon    umsetzt.  



  Das neue Produkt ist ein bräunlich  schwarzes, kristallines Pulver, das sich in  konzentrierter Schwefelsäure mit olivgrüner  Farbe löst, nicht     verküpt    und einen Schmelz  punkt über<B>350'</B> besitzt. Das erhaltene     Di-          (4'-benzoylamino-1'-anthrachinonyl)    -2,6     -di-          a.minonaphthalin    stellt ein wertvolles Zwi  schenprodukt für die Herstellung von     Küpen-          farbstoffen    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>    15 Teile wasserfreies     Natriumcarbonat     und 15 Teile entwässertes     Natriumacetat     werden in 500 Teilen Nitrobenzol so lange im  Sieden gehalten, bis 50 Teile Nitrobenzol ab  destilliert sind.

   Nach dem Abkühlen auf 200'  werden 14,3 Teile 2,6 -     Dibromnaphthalin,     35,2 Teile     1-Amino-4-benzoylaminoanthra-          chinon    und 1,3     Teile        Kupferchlorür    zuge  setzt und die Reaktionsmischung 24     Stunden     bei 195 bis 205   gerührt. Nun wird heiss  filtriert, mit Nitrobenzol sowie mit Benzol       und    Alkohol gewaschen, und das erhaltene  Produkt zur weiteren Reinigung mit verdünn  ter Salzsäure     ausgekocht,        abfiltriert,    ge  waschen 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 by reacting 1 mole of 2,6-dihalonaphthalene with 2 moles of 1-amino-4-benzoylaminoanthraquinone.



  The new product is a brownish black, crystalline powder that dissolves in concentrated sulfuric acid with an olive green color, does not condense and has a melting point of over <B> 350 '</B>. The di- (4'-benzoylamino-1'-anthraquinonyl) -2,6-di-a.minonaphthalene obtained is a valuable intermediate product for the production 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, and acid-binding agents. <I> Example: </I> 15 parts of anhydrous sodium carbonate and 15 parts of dehydrated sodium acetate are boiled in 500 parts of nitrobenzene until 50 parts of nitrobenzene have distilled off.

   After cooling to 200 ', 14.3 parts of 2,6-dibromonaphthalene, 35.2 parts of 1-amino-4-benzoylaminoanthraquinone and 1.3 parts of copper chloride are added and the reaction mixture is stirred at 195-205 for 24 hours. It is then filtered hot, washed with nitrobenzene and with benzene and alcohol, and the product obtained is boiled for further purification with dilute hydrochloric acid, filtered off, washed and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines stick stoffhaltigen Naphthalinderivates, dadurch gekennzeichnet, dass man 1 Mol 2,6-Dihalogen- naphthalin mit 2 Mol 1-Amino-4-benzoyl- aminoanthrachinon umsetzt. PATENT CLAIM: Process for the production of a nitrogen-containing naphthalene derivative, characterized in that 1 mole of 2,6-dihalogen naphthalene is reacted with 2 moles of 1-amino-4-benzoyl-aminoanthraquinone. Das neue Produkt ist ein kristallines Pulver, das sich in konzentrierter Schwefelsäure mit olivgrüner Farbe löst, nicht verküpt und einen Schmelz punkt über 350 besitzt. Das erhaltene Di- (4'-benzoylamino -1'-anthrachinonyl) - 2,6 - di- aminona.phthalin stellt ein wertvolles Zwi schenprodukt für die Herstellung von Küpen- farbstoffen dar. The new product is a crystalline powder that dissolves in concentrated sulfuric acid with an olive green color, does not vat and has a melting point of over 350. The resulting di- (4'-benzoylamino -1'-anthraquinonyl) - 2,6 - di-aminona.phthalin is a valuable intermediate product for the production of vat dyes.
CH212331D 1937-12-20 1937-12-20 Process for the production of a nitrogen-containing naphthalene derivative. CH212331A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH206427T 1937-12-20
CH212331T 1937-12-20

Publications (1)

Publication Number Publication Date
CH212331A true CH212331A (en) 1940-11-15

Family

ID=25724303

Family Applications (1)

Application Number Title Priority Date Filing Date
CH212331D CH212331A (en) 1937-12-20 1937-12-20 Process for the production of a nitrogen-containing naphthalene derivative.

Country Status (1)

Country Link
CH (1) CH212331A (en)

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