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DE767072C - Verfahren zur Darstellung von 3-Nitro-4-aminotoluol - Google Patents

Verfahren zur Darstellung von 3-Nitro-4-aminotoluol

Info

Publication number
DE767072C
DE767072C DES147519D DES0147519D DE767072C DE 767072 C DE767072 C DE 767072C DE S147519 D DES147519 D DE S147519D DE S0147519 D DES0147519 D DE S0147519D DE 767072 C DE767072 C DE 767072C
Authority
DE
Germany
Prior art keywords
nitro
aminotoluene
preparation
toluidine
water
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
DES147519D
Other languages
English (en)
Inventor
Adolf Dr Schwarz
Rolf Dr Koenig
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Siegle & Co G GmbH
Original Assignee
Siegle & Co G GmbH
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 Siegle & Co G GmbH filed Critical Siegle & Co G GmbH
Priority to DES147519D priority Critical patent/DE767072C/de
Application granted granted Critical
Publication of DE767072C publication Critical patent/DE767072C/de
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
    • C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
    • C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
    • C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
    • C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
    • C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups

Landscapes

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

Description

  • Verfahren zur Darstellung von 3-Nitro-4-aminotoluol Die technische Darstellung des 3-Nitro-4-aminotoluols erfolgt durch Nitrierung des aus Essigsäure und p-Toluidin entstehenden Acet-p-toluidids und Verseifung des gebildeten 3-Nitro-4-acetaminotoluols durch Kochen mit alkoholischer Kalilauge oder konzentrierter Salzsäure. Auf alle Fälle sind zur Darstellung der Nitrobase nach diesem Verfahren drei Stufen nötig: Acetylieren des p-Toluidins, Nitrieren der Acetylverbindüng, Verseifen der gebildeten Nit#o-acetamino-Verbindung.
  • Es wurde nun die überraschende Beobachtung gemacht, daß, wenn man statt der Acetylverbindung die, Formylverbindung des p-Toluidins zur Nitrierung benutzt, man beim Eingießen der Nitrierflüssigkeit in Wasser unmittelbar das 3-Nitro-4-aminotoluol erhält. Dies war um so überraschender, als nach den Literaturangaben (Beilsteins Handbuch der organischen Chemie, 4. Aufl., z2. Bd., S.:231, 718) sich beim Nitrieren des Formanilids und Eintragen des Nitriergemisches in Wasser sich das 4-Nitroformanilid abscheidet, das genau so wie die Acetylverbindung erst verseift werden muß, um die freie Base zu erhalten. Nach vorliegendem Verfahren sind also zur Darstellung der Base nur noch zwei Stufen nötig: Formylieren des p-Toluidins, Nitrieren und Verseifen gehen in einer Stufe vor sich. Das neue Verfahren stellt also gegenüber dem bekannten Verfahren einen technischen Fortschritt dar.
  • Beispiel 87,5 Gewichtsteile Form-p-toluidid werden bei 2o bis 30° in ein Gemisch von 13o Raumteilen Salpetersäure (6a°/oig) und 69 Raumteilen konzentrierter Schwefelsäure eingetragen und r Stunde bei Zimmertemperatur gerührt. Beim Eingießen in Wasser fällt das 3--N itro--t-aminotoluol aus, das abgesaugt, gewaschen und getrocknet wird.

Claims (1)

  1. PATENTANSPRUCH: Verfahren zur Darstellung von 3-1 itro-4-aminotoluol, dadurch gekennzeichnet, daß man Form-p-toluidid bei Zimmertemperatur nitriert und das -Nitriergemisch in Wasser eingießt.
DES147519D 1941-11-01 1941-11-01 Verfahren zur Darstellung von 3-Nitro-4-aminotoluol Expired DE767072C (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DES147519D DE767072C (de) 1941-11-01 1941-11-01 Verfahren zur Darstellung von 3-Nitro-4-aminotoluol

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DES147519D DE767072C (de) 1941-11-01 1941-11-01 Verfahren zur Darstellung von 3-Nitro-4-aminotoluol

Publications (1)

Publication Number Publication Date
DE767072C true DE767072C (de) 1951-08-23

Family

ID=7542478

Family Applications (1)

Application Number Title Priority Date Filing Date
DES147519D Expired DE767072C (de) 1941-11-01 1941-11-01 Verfahren zur Darstellung von 3-Nitro-4-aminotoluol

Country Status (1)

Country Link
DE (1) DE767072C (de)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0027658A1 (de) * 1979-10-23 1981-04-29 Bayer Ag Verfahren zur Herstellung von 3-Nitro-4-aminotoluol
EP0047337A1 (de) * 1980-09-09 1982-03-17 Bayer Ag Verfahren zur Herstellung von 3-Nitro-4-aminotoluol
US4600797A (en) * 1979-10-23 1986-07-15 Bayer Aktiengesellschaft Process for the preparation of nitroaminobenzenes

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0027658A1 (de) * 1979-10-23 1981-04-29 Bayer Ag Verfahren zur Herstellung von 3-Nitro-4-aminotoluol
US4600797A (en) * 1979-10-23 1986-07-15 Bayer Aktiengesellschaft Process for the preparation of nitroaminobenzenes
EP0047337A1 (de) * 1980-09-09 1982-03-17 Bayer Ag Verfahren zur Herstellung von 3-Nitro-4-aminotoluol

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