CH213188A - 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
CH213188A
CH213188A CH213188DA CH213188A CH 213188 A CH213188 A CH 213188A CH 213188D A CH213188D A CH 213188DA CH 213188 A CH213188 A CH 213188A
Authority
CH
Switzerland
Prior art keywords
nitrogen
production
naphthalene derivative
containing naphthalene
mol
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 CH213188A publication Critical patent/CH213188A/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
    • C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
    • C09B3/22—Dibenzanthrones; Isodibenzanthrones
    • C09B3/30—Preparation from starting materials already containing the dibenzanthrone or isodibenzanthrone nucleus
    • C09B3/38—Preparation from starting materials already containing the dibenzanthrone or isodibenzanthrone nucleus by introduction of hydrocarbon or acyl residues into amino groups
    • 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 Nr. 206427.    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     142o1        Aminodibenzanthron,     das durch     Mononitrieren    und Reduzieren  von     Dibenzanthron    erhältlich ist, umsetzt.  



  Das neue Produkt ist ein schwarzes Pul  ver, das bei 460   noch nicht schmilzt, sich  in konzentrierter Schwefelsäure mit gelb  grüner Farbe löst und Baumwolle aus blauer       Küpe    in graugrünen Tönen färbt. Es stellt  überdies 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.            Beispiel:

       14,3 Teile     2,6-Dibromnaphthalin    werden  mit 51 Teilen     Aminodibenzanthron,    erhalten  durch     Mononitrieren    und Reduzieren von       Dibenzanthron,        1.,3    Teilen     Kupferchlorür,     15 Teilen wasserfreiem     Natriumearbonat    und  15 Teilen entwässertem     Natriumacetat    in  480 Teilen trockenem     Nitrobenzol    unter Rüh  ren zum Sieden erhitzt. Nach beendigter  Reaktion wird heiss filtriert, der Rückstand  mit     Nitrobenzol,    Benzol und Alkohol gewa  schen, mit verdünnter Salzsäure ausgekocht,  filtriert, gewaschen und getrocknet.



  <B> Additional patent </B> to main patent no. 206427. 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 mole of 2,6-dihalogen naphthalene is reacted with 2 142o1 aminodibenzanthrone, which is obtainable by mononitrating and reducing dibenzanthrone.



  The new product is a black powder that does not yet melt at 460, dissolves in concentrated sulfuric acid with a yellow-green color and dyes cotton from a blue vat in gray-green tones. It is also a valuable intermediate product 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, and acid-binding agents. Example:

       14.3 parts of 2,6-dibromonaphthalene are heated to boiling with 51 parts of aminodibenzanthrone, obtained by mononitrating and reducing dibenzanthrone, 1., 3 parts of copper chloride, 15 parts of anhydrous sodium carbonate and 15 parts of dehydrated sodium acetate in 480 parts of dry nitrobenzene 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 mit 2 Mol Aminodibenz- anthron, das durch Mononitrieren und Redu zieren von Dibenzauthron erhältlich ist, um setzt. PATENT CLAIM: A process for the production of a nitrogen-containing naphthalene derivative, characterized in that 1 mol of 2,6-dihalogen naphthalene is reacted with 2 mol of aminodibenzanthrone, which can be obtained by mononitrating and reducing dibenzauthrone. Das neue Produkt ist ein schwarzes Pul ver, das bei 460' noch nicht schmilzt, sich in konzentrierter Schwefelsäure mit gelbgrüner Farbe löst und Baumwolle aus blauer Küpe in gradgrünen Tönen färbt. Es stellt über- dies ein wertvolles Zwischenprodukt für die Herstellung von Küpenfarbstoffen dar. The new product is a black powder that does not yet melt at 460 ', dissolves in concentrated sulfuric acid with a yellow-green color and dyes cotton from a blue vat in shades of green. It is also a valuable intermediate product for the manufacture of vat dyes.
CH213188D 1937-12-20 1937-12-20 Process for the production of a nitrogen-containing naphthalene derivative. CH213188A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH206427T 1937-12-20
CH213188T 1937-12-20

Publications (1)

Publication Number Publication Date
CH213188A true CH213188A (en) 1941-01-15

Family

ID=25724311

Family Applications (1)

Application Number Title Priority Date Filing Date
CH213188D CH213188A (en) 1937-12-20 1937-12-20 Process for the production of a nitrogen-containing naphthalene derivative.

Country Status (1)

Country Link
CH (1) CH213188A (en)

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