DE638486C - Process for the preparation of 3-chloro-2-nitrotoluene - Google Patents

Process for the preparation of 3-chloro-2-nitrotoluene

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Publication number
DE638486C
DE638486C DEI48569D DEI0048569D DE638486C DE 638486 C DE638486 C DE 638486C DE I48569 D DEI48569 D DE I48569D DE I0048569 D DEI0048569 D DE I0048569D DE 638486 C DE638486 C DE 638486C
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DE
Germany
Prior art keywords
chloro
nitrotoluene
preparation
parts
weight
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
DEI48569D
Other languages
German (de)
Inventor
Dr Adolf Sieglitz
Dr Konrad Stenger
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.)
IG Farbenindustrie AG
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
Priority to DEI48569D priority Critical patent/DE638486C/en
Application granted granted Critical
Publication of DE638486C publication Critical patent/DE638486C/en
Expired legal-status Critical Current

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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
    • C07C201/10—Preparation of nitro compounds by substitution of functional groups by nitro groups

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

Description

DEUTSCHES REICHGERMAN EMPIRE

AUSGEGEBEN AM
20. NOVEMBER 1936ISSUED ON
November 20, 1936

REICHSPATENTAMTREICH PATENT OFFICE

PATENTSCHRIFTPATENT LETTERING

KLASSE 12ο GRUPPE 2oiCLASS 12ο GROUP 2oi

I. G. Farbenindustrie Akt.-Ges. in Frankfurt a. M.*) Verfahren zur Herstellung von 3-Chlor-2-nitrotoluolI. G. Farbenindustrie Akt.-Ges. in Frankfurt a. M. *) Process for the preparation of 3-chloro-2-nitrotoluene

Patentiert im Deutschen Reiche vom 16. Dezember 1933 abPatented in the German Empire on December 16, 1933

3-Chlor-2-nitrotoluol war bisher nur auf umständlichen und technisch nicht brauchbaren Wegen zugänglich. Die in den Berichten der Deutschen chemischen Gesellschaft,. Bd. 40, S. 3332, beschriebene Methode zur Herstellung von 3-Chlor-2-nitrotoluol durch Entamidierung von 6-Amino-3-chlor-2-nitroi-methylbenzol verläuft nach den Angaben im Journal of the Chemical Society 1907, I, S. 970 ff., mit schlechten Ausbeuten. Auch die im Journal of the Chemical Society 1929, S. 2740 und 2741, angegebene Herstellungsweise von 3 - Chlor - 2 - nitrotoluol aus 2, 3-Dinitro-4-aminotoluol durch Entamidierung und Ersatz einer Nitrogruppe durch ein Chloratom verläuft nach den dort verzeichneten Angaben nur mit mäßiger Ausbeute.3-chloro-2-nitrotoluene was previously only cumbersome and technically unusable Paths accessible. Those in the reports of the German Chemical Society. Vol. 40, p. 3332, described method for the preparation of 3-chloro-2-nitrotoluene by Deamidation of 6-amino-3-chloro-2-nitroimethylbenzene runs according to the information in the Journal of the Chemical Society 1907, I, p. 970 ff., With poor yields. Also published in the Journal of the Chemical Society 1929, P. 2740 and 2741, the specified method of preparation of 3 - chloro - 2 - nitrotoluene 2,3-Dinitro-4-aminotoluene by deamidation and replacement of a nitro group by a According to the information given there, the chlorine atom proceeds only with moderate yield.

Es wurde nun gefunden, daß man mit aus-• gezeichneter Ausbeute in technisch leicht durchführbarer Reaktion 3-Clor-2-nitrotoluol aus 3-Chlor-2-toluidin erhalten kann, wenn man die Diazoverbindung dieses Amins mit dem unter der-Bezeichnung »Etardsches Salz« bekannten Cuprocuprisulfit und überschüs-It has now been found that with an excellent yield in technically easy feasible reaction 3-chloro-2-nitrotoluene can be obtained from 3-chloro-2-toluidine if the diazo compound of this amine with the under the name "Etardsches Salz" known cuprocuprisulphite and excess

sigem Alkalinitrit behandelt. Das roteKupfer-. komplexsalz läßt sich leicht nach den Angaben in Gmelin-Kraüt, Handbuch, der anorganischen Chemie, VII. Auflage, Bd. V,treated alkaline nitrite. The red copper. complex salt can easily be according to the information in Gmelin-Kraüt, manual, the inorganic Chemie, VIIth edition, Vol. V,

S. S25, durch Einleiten von schwefliger Säure in eine Kupferacetatlösung herstellen.S. S25, by introducing sulphurous acid into a copper acetate solution.

Das 3-Chlor-2-nitrotoluol stellt ein wertvolles Zwischenprodukt zur Herstellung von Farbstoffen dar, das sich durch große Reaktionsfähigkeit auszeichnet, da sich das Chlor leicht durch die verschiedensten Reste ersetzen läßt. Man kann die Verbindung z. B. mit Natriumalkylaten, Natriumphenolaten, sulfinsäuren Salzen, Ammoniak oder Aminen umsetzen und dadurch zu einer ganzen Reihe bisher unzugänglicher Körper gelangen.The 3-chloro-2-nitrotoluene is a valuable intermediate for the production of Dyes, which are characterized by great reactivity, as the Chlorine can easily be replaced by a wide variety of residues. You can make the connection z. B. with sodium alkoxides, sodium phenates, sulfinic acid salts, ammonia or convert amines and thereby to a whole series of previously inaccessible bodies reach.

Beispielexample

44 Gewichtsteile 3-Chlor-2-toluidin werden in 3-1,5 Gewichtsteilen konzentrierter Schwefelsäure und etwa 250 Gewichtsteilen Wasser gelöst und mit einer Lösung von 23,3 Gewichtsteilen Natriumnitrit in Wasser diazotiert. Die Diazolösung fließt unter Rühren zu einem Gemisch von 50 Gewichtsteilen Cuprocuprisulfit und 150 Gewichtsteilen 50· Natriumnitrit in etwa 800 Gewichtsteilen Wasser.44 parts by weight of 3-chloro-2-toluidine are dissolved in 3-1.5 parts by weight of concentrated sulfuric acid and about 250 parts by weight of water and dissolved with a solution of 23.3 parts by weight Sodium nitrite diazotized in water. The diazo solution flows to a mixture of 50 parts by weight with stirring Cuprocuprisulfite and 150 parts by weight of 50 x sodium nitrite in about 800 parts by weight Water.

Unter Schäumen färbt sich das Reaktionsgemisch gelbgrün, und es tritt der charakteristische ,Geruch der Nitrokörper auf. Man läßt noch etwa 2 Stunden bei gewöhnlicherThe reaction mixture turns yellow-green with foaming, and the characteristic one occurs , Smell the nitro bodies on. It is left at the normal for about 2 hours

*) Von dem Patentsucher sind als die Erfinder angegeben worden:*) The patent seeker indicated the following as the inventors:

Dr. Adolf Steglitz in Frankfurt a. M.-Höchst und Dr. Konrad Stenger in Frankfurt a. M.Dr. Adolf Steglitz in Frankfurt a. M.-Höchst and Dr. Konrad Stenger in Frankfurt a. M.

Temperatur rühren und destilliert den Nitrokörper mit Wasserdampf · ab, wobei er als helles öl übergeht, das "beim Abkühlen erstarrt. Das 3-ChIor-2-nitrotoluol siedet unter einem Druck von io mm bei in bis 1120. Die Ausbeute beträgt etwa 75 % an reinem; Nitrokörper.Temperature stirring and distilling the nitro compound with steam · from where it passes as a light oil, the "solidifies on cooling. The 3-chloro-2-nitrotoluene boils under a pressure of io mm in to 112 0th The yield is about 75 % of pure; nitro bodies.

Claims (1)

Patentanspruch:Claim: Verfahren zur Herstellung von 3-Chlor-2-nitrotoluol, dadurch gekennzeichnet, daß man die Diazoverbindung des 3-Clor-2-toluidins mit Cuprocuprisulnt und überschüssigem Alkalinitrit behandelt.Process for the preparation of 3-chloro-2-nitrotoluene, characterized in that the diazo compound of 3-chloro-2-toluidine treated with cuprocuprisulnt and excess alkali nitrite.
DEI48569D 1933-12-16 1933-12-16 Process for the preparation of 3-chloro-2-nitrotoluene Expired DE638486C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI48569D DE638486C (en) 1933-12-16 1933-12-16 Process for the preparation of 3-chloro-2-nitrotoluene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI48569D DE638486C (en) 1933-12-16 1933-12-16 Process for the preparation of 3-chloro-2-nitrotoluene

Publications (1)

Publication Number Publication Date
DE638486C true DE638486C (en) 1936-11-20

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Family Applications (1)

Application Number Title Priority Date Filing Date
DEI48569D Expired DE638486C (en) 1933-12-16 1933-12-16 Process for the preparation of 3-chloro-2-nitrotoluene

Country Status (1)

Country Link
DE (1) DE638486C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105189447A (en) * 2013-06-25 2015-12-23 庵原化学工业株式会社 Method for manufacturing nitrobenzene compound

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105189447A (en) * 2013-06-25 2015-12-23 庵原化学工业株式会社 Method for manufacturing nitrobenzene compound
EP3015451A4 (en) * 2013-06-25 2017-03-01 Ihara Chemical Industry Co., Ltd. Method for manufacturing nitrobenzene compound
CN105189447B (en) * 2013-06-25 2017-12-05 组合化学工业株式会社 The method for manufacturing nitrobenzene compound

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