CH147688A - Process for the preparation of an aminodiphenylamine derivative. - Google Patents

Process for the preparation of an aminodiphenylamine derivative.

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Publication number
CH147688A
CH147688A CH147688DA CH147688A CH 147688 A CH147688 A CH 147688A CH 147688D A CH147688D A CH 147688DA CH 147688 A CH147688 A CH 147688A
Authority
CH
Switzerland
Prior art keywords
aminodiphenylamine
derivative
preparation
base
parts
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
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
Publication of CH147688A publication Critical patent/CH147688A/en

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Description

  

  Verfahren zur Herstellung eines     Aminodiphenylaminderivates.       Vorliegendes Patent bezieht sich auf     eiii     Verfahren zur Herstellung eines,     Aminodi-          phenylaminderivates,    dadurch gekennzeichnet,  dass man     Nitrosobenzol    mit     o-Nitrosotoluol     kondensiert und das Kondensationsprodukt  mit einem Reduktionsmittel behandelt.  



  Die über das Chlorhydrat und durch Um  kristallisieren erhaltene, bisher nicht bekannte  Base besitzt den     Schmelzpunkt    70-71  .  Ihre     Acetylverbindung    schmilzt bei 147-148  .  



  Da die Base mit dem aus     p-Nitrochlor-          benzolsulfosäure    und     o-Toluidin    erhaltenen       4-Amino-2'-methyldiphenylamin,        vergl.    Be  richte der deutschen chemischen Gesellschaft,       Bd.        .11,    Seite 3750, nicht identisch ist, kommt  ihr die Konstitution eines     4-Amino-3-methyl-          diphenylamins    zu.  



  <I>Beispiel:</I>  Eine Lösung von     53;5    Teilen     Nitroso-          benzol    und 60,5 Teilen     o-Nitrosotoluol    in  300 Teilen Eisessig wird in 1100 Teile    Schwefelsäure 66       B6    bei     +    5   in ungefähr  2 Stunden eingetropft. Beim langsamen Ein  rühren der klaren schwefelsauren Lösung in  Eiswasser fallen gelbbraune Flocken aus, die  abgesaugt und säurefrei gewaschen werden.  Der Schmelzpunkt des gelbbraunen Körpers  ist 142  .

   Es wird noch feucht in 3000 Tei  len Nasser und 65 Teilen     Ätznatronlauge     von 38       Be    gelöst und bei 60   mit einer  Lösung von 175 Teilen     geschmolzenem          Schwefelnatrium    in Wasser versetzt und  eine halbe Stunde auf 80       erwärmt,    wobei  unter Hellfärbung der Lauge die Base als  helles 01 ausfällt, das beim Abkühlen er  starrt und dann abgesaugt und ausgewaschen  wird.



  Process for the preparation of an aminodiphenylamine derivative. The present patent relates to a process for the preparation of an aminodiphenylamine derivative, characterized in that nitrosobenzene is condensed with o-nitrosotoluene and the condensation product is treated with a reducing agent.



  The previously unknown base obtained via the chlorohydrate and by recrystallization has a melting point of 70-71. Your acetyl compound melts at 147-148.



  Since the base is not identical to the 4-amino-2'-methyldiphenylamine obtained from p-nitrochlorobenzenesulfonic acid and o-toluidine, cf. reports of the German Chemical Society, vol. 11, page 3750, the constitution comes from it a 4-amino-3-methyl-diphenylamine to.



  <I> Example: </I> A solution of 53; 5 parts of nitrosobenzene and 60.5 parts of o-nitrosotoluene in 300 parts of glacial acetic acid is added dropwise to 1100 parts of sulfuric acid 66 B6 at +5 in about 2 hours. When the clear sulfuric acid solution is slowly stirred into ice water, yellow-brown flakes precipitate, which are suctioned off and washed acid-free. The melting point of the yellow-brown body is 142.

   It is dissolved while still moist in 3000 parts of water and 65 parts of caustic soda solution of 38 Be and at 60 a solution of 175 parts of molten sodium sulphide in water is added and the mixture is heated to 80 for half an hour, the base precipitating as light 01 while the alkali turns light in color that stares as it cools and is then vacuumed and washed out.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Amino- diphenylaininderivates, dadurch gekennzeich net, dass man Nitrosobenzol mit o-Nitroso- toluol kondensiert und das Kondensations- Produkt mit einem Reduktionsmittel be handelt. Die über das Chlorhydrat und durch Um kristallisieren erhaltene Base besitzt den Schmelzpunkt 70-71 . Ihre Acetylverbin- dung schmilzt bei l47-148 . PATENT CLAIM: Process for the production of an aminodiphenylamine derivative, characterized in that nitrosobenzene is condensed with o-nitrosotoluene and the condensation product is treated with a reducing agent. The base obtained via the chlorohydrate and by recrystallizing has a melting point of 70-71. Its acetyl compound melts at 147-148. Da die Base mit dem aus p-Nitrochlor- benzolsulfosäure und o-Toluidin erhaltenen 4-Amino-2'-inethyldiplienylamin, - vergl. Be richte der deutschen chemischen Gesellschaft, Bd. 41, Seite 3750, nicht identisch ist, kommt ihr die Konstitution eines 4-Amiro- 3-inethyldiplienylainins zu. Since the base is not identical to the 4-amino-2'-ynethyldiplienylamine obtained from p-nitrochlorobenzenesulfonic acid and o-toluidine, - see reports of the German Chemical Society, Vol. 41, page 3750, the constitution comes from it of a 4-amiro-3-ynethyldiplienylainins.
CH147688D 1929-02-15 1929-09-20 Process for the preparation of an aminodiphenylamine derivative. CH147688A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE147688X 1929-02-15
CH145992T 1929-09-20

Publications (1)

Publication Number Publication Date
CH147688A true CH147688A (en) 1931-06-15

Family

ID=25714779

Family Applications (1)

Application Number Title Priority Date Filing Date
CH147688D CH147688A (en) 1929-02-15 1929-09-20 Process for the preparation of an aminodiphenylamine derivative.

Country Status (1)

Country Link
CH (1) CH147688A (en)

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