DE1056619B - Process for the preparation of 4-nitro-diarylamines - Google Patents

Process for the preparation of 4-nitro-diarylamines

Info

Publication number
DE1056619B
DE1056619B DEF21782A DEF0021782A DE1056619B DE 1056619 B DE1056619 B DE 1056619B DE F21782 A DEF21782 A DE F21782A DE F0021782 A DEF0021782 A DE F0021782A DE 1056619 B DE1056619 B DE 1056619B
Authority
DE
Germany
Prior art keywords
parts
nitrobenzene
mixture
hours
potassium carbonate
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.)
Pending
Application number
DEF21782A
Other languages
German (de)
Inventor
Dr Klaus Schwarzer
Dr Rudolf Stroh
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Priority to DEF21782A priority Critical patent/DE1056619B/en
Priority claimed from GB5482/59A external-priority patent/GB855719A/en
Publication of DE1056619B publication Critical patent/DE1056619B/en
Pending legal-status Critical Current

Links

Classifications

    • 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
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
    • C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
    • 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
    • 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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

DEUTSCHESGERMAN

Es ist bekannt, daß man p-Chlor-nitrobenzol mit Ammoniak oder aliphatischen Aminen zu p-Nitranilin oder N-substituierten p-Nitranilinen umsetzen kann (vgl. deutsche Patentschrift 148 749). Bei Verwendung von aromatischen Aminen werden jedoch technisch nicht zufriedenstellende Ausbeuten erzielt. Auch bei der in der deutschen Patentschrift 185 663 beschriebenen Verfahrensweise, bei der in Gegenwart von Kupferjodür oder Mischungen von Kupferpulver und" Jod gearbeitet wird, werden keine zufriedenstellenden Ausbeuten erhalten.It is known that p-chloro-nitrobenzene with Can convert ammonia or aliphatic amines to p-nitroaniline or N-substituted p-nitroanilines (see German patent specification 148 749). When using aromatic amines, however, technical unsatisfactory yields achieved. Also in the case of the one described in German patent specification 185 663 Procedure in which in the presence of copper iodine or mixtures of copper powder and "iodine is worked, satisfactory yields are not obtained.

Es wurde nun gefunden, daß man 4-Nitro-diarylamine mit guter Ausbeute erhält, wenn man gegebenenfalls substituierte p-Halogennitrobenzole mit gegebenenfalls substituierten, am Stickstoff acylierten Arylaminen umsetzt.It has now been found that 4-nitro-diarylamines obtained in good yield if optionally substituted p-halonitrobenzenes with optionally substituted arylamines acylated on nitrogen.

Für das erfindungsgemäße Verfahren geeignete p-Halogermitrobenzole sind z. B. p-Chlor-nitrobenzol, p-Bromnitrobenzol oder l,2-Dichlor-4-nitrobenzol. Geeignete Acylarylamine sind z. B. Formanilid, Acetanilid, Formyl-a-naphthalid und Formyl-p-toluidid.For the process according to the invention suitable p-Halogermitrobenzenes are, for. B. p-chloro-nitrobenzene, p-bromonitrobenzene or 1,2-dichloro-4-nitrobenzene. Suitable acylarylamines are, for. B. formanilide, acetanilide, Formyl-a-naphthalide and formyl-p-toluidide.

Die Durchführung des erfindungsgemäßen Verfahrens erfolgt zweckmäßigerweise bei erhöhter Temperatur, z. B. bei 150 bis 250° C, vorzugsweise 180 bis 2200C; jedoch können auch höhere oder tiefere Temperaturen angewandt werden. Im allgemeinen ist es vorteilhaft, wenn man in Gegenwart von Kupferpulver oder einer Kupferverbindung arbeitet. Um die bei der Reaktion entstehenden Halogenwasserstoffe zu binden, setzt man zweckmäßig säurebindende Verbindungen, z. B. Alkalicarbonate, Alkaliacetate oder Magnesiumoxyd, "zu. Im allgemeinen ist es nicht erforderlich, daß man ein Lösungsmittel verwendet, jedoch kann man auch, falls es gewünscht wird, in Gegenwart inerter Lösungsmittel arbeiten.The process according to the invention is expediently carried out at an elevated temperature, e.g. B. at 150 to 250 ° C, preferably 180 to 220 0 C; however, higher or lower temperatures can also be used. In general, it is advantageous to work in the presence of copper powder or a copper compound. In order to bind the hydrogen halides formed in the reaction, it is expedient to use acid-binding compounds, e.g. B. alkali carbonates, alkali acetates or magnesium oxide ". In general, it is not necessary to use a solvent, but it is also possible, if desired, to work in the presence of inert solvents.

Es ist weiterhin nicht erforderlich, daß man direkt die Acylderivate der Arylamine einsetzt, sondern man kann diese Verbindungen auch erst im Reaktionsgemisch aus den Ausgangskomponenten erzeugen. It is also not necessary to use the acyl derivatives of the arylamines directly, but rather one can also produce these compounds only in the reaction mixture from the starting components.

Ein besonderer Vorteil des erfindungsgemäßen Verfahrens liegt darin, daß die 4-Nitro-diarylamine in sehr reiner Form anfallen, so daß sie in vielen Fällen ohne λ orherige Isolierung weiterverarbeitet werden können. So kann das 4-Nitro-diphenylamin z. B. ohne vorherige Isolierung durch katalytische Hydrierung in 4-Amino-diphenylamin ü1>ergeführt werden.A particular advantage of the process according to the invention is that the 4-nitro-diarylamines in very in pure form, so that they can be processed further in many cases without prior isolation. So the 4-nitro-diphenylamine z. B. without prior Isolation by catalytic hydrogenation in 4-amino-diphenylamine can be performed.

Beispiel 1example 1

Eine Mischung aus 78 Teilen p-Chlor-nitrobenzol, 95 Teilen Formanilid, 40 Teilen Kaliumcarbonat undA mixture of 78 parts of p-chloro-nitrobenzene, 95 parts of formanilide, 40 parts of potassium carbonate and

1 Teil Kupferoxyd wird in einem Rührkolben1 part of copper oxide is poured into a stirred flask

2 Stunden auf 180° C, dann 1 Stunde auf 190° C und 2 Stunden auf 200° C erhitzt, dann auf 80° C abgekühlt, mit 150 Teilen Benzol verdünnt und noch heiß Verfahren zur Herstellung von 4-Nitro-diarylaminen2 hours at 180 ° C, then 1 hour at 190 ° C and Heated to 200 ° C. for 2 hours, then cooled to 80 ° C., diluted with 150 parts of benzene and while still hot Process for the preparation of 4-nitro-diarylamines

Anmelder:Applicant:

Farbenfabriken Bayer Aktiengesellschaft, Leverkusen-BayerwerkPaint factories Bayer Aktiengesellschaft, Leverkusen-Bayerwerk

Dr. Klaus Schwarzer, Koln-Flittard, und Dr. Rudolf Stroh, Leverkusen, sind als Erfinder genannt wordenDr. Klaus Schwarzer, Koln-Flittard, and Dr. Rudolf Stroh, Leverkusen, have been named as inventors

von den anorganischen Salzen abfiltriert. Beim Abkühlen der Lösung kristallisieren 53 Teile 4-Nitrodiphenylamin, Schmelzpunkt des Rohproduktes 127 bis 130° C. Durch Einengen der Mutterlauge kann die Ausbeute noch erhöht werden.filtered off from the inorganic salts. When the solution cools, 53 parts of 4-nitrodiphenylamine crystallize, Melting point of the crude product 127 to 130 ° C. By concentrating the mother liquor can the yield can still be increased.

Beispiel 2Example 2

Eine Mischung aus 78 Teilen p-Chlor-nitrobenzol, 95 Teilen Formanilid und 40 Teilen Kaliumcarbonat wird 5 Stunden auf 200° C erhitzt. Anschließend werden nicht umgesetztes p-Chlor-nitrobenzol und Formanilid mit Wasserdampf abgetrieben. Als Rückstand verbleiben 85 Teile 4-Nitro-diphenylamin. Schmelzpunkt des Rohproduktes: 125 bis 126° C.A mixture of 78 parts of p-chloro-nitrobenzene, 95 parts of formanilide and 40 parts of potassium carbonate is heated to 200 ° C for 5 hours. Then unreacted p-chloro-nitrobenzene and Formanilide stripped off with steam. 85 parts of 4-nitro-diphenylamine remain as residue. Melting point of the crude product: 125 to 126 ° C.

B e i s ρ i e 1 3 35B e i s ρ i e 1 3 35

Eine Mischung aus 78 Teilen p-Chlor-nitrobenzol, 70 Teilen Anilin und 35 Teilen Ameisensäure (D = 1,22) wird in einem Rührkolben, der mit einem absteigenden Kühler versehen ist, erhitzt. Nachdem die Hauptmenge des Reaktionswassers abdestilliert ist, werden 60 Teile Kaliumcarbonat und 1 Teil Kupferoxyd eingetragen und dann 5 Stunden auf 200° C erhitzt. Anschließend werden nicht umgesetztes p-Chlor-nitrobenzol und Anilin bzw. Formanilid mit Wasserdampf abgetrieben. Als Rückstand verbleiben 91 Teile 4-Nitro-diphenylamin.A mixture of 78 parts of p-chloro-nitrobenzene, 70 parts of aniline and 35 parts of formic acid (D = 1.22) is heated in a stirred flask equipped with a descending condenser. After most of the water of reaction has distilled off, 60 parts of potassium carbonate and 1 part of copper oxide are added and the mixture is then heated to 200 ° C. for 5 hours. Unreacted p-chloro-nitrobenzene and aniline or formanilide are then driven off with steam. 91 parts of 4-nitro-diphenylamine remain as residue.

Beispiel 4Example 4

Eine Mischung aus 78 Teilen p-Chlor-nitrobenzol, 67,5 Teilen Acetanilid, 50 Teilen Kaliumacetat und 5 Teilen Kupferoxyd wird 5 Stunden auf 200° C erhitzt, dann mit Benzol verdünnt und noch heiß von den anorganischen Salzen abfiltriert. Beim Abkühlen kristallisiert aus der Lösung 4-Nitro-diphenylamin.A mixture of 78 parts of p-chloro-nitrobenzene, 67.5 parts of acetanilide, 50 parts of potassium acetate and 5 parts of copper oxide are heated to 200 ° C for 5 hours, then diluted with benzene and still hot from the inorganic salts filtered off. On cooling, 4-nitro-diphenylamine crystallizes from the solution.

909 509/436909 509/436

200° C erhitzt und die Lösung noch heiß filtriert. Aus dem Filtrat kristallisieren beim Abkühlen 62 Teile 2-Chlor-4-nitro-diphenylamin aus. Schmelzpunkt des Rohproduktes 107 bis 108° C (nach dem Umkristalliseren aus Alkohol F. 113° C;.Heated to 200 ° C and the solution filtered while still hot. Crystallize from the filtrate on cooling 62 parts of 2-chloro-4-nitro-diphenylamine from. Melting point of the crude product 107 to 108 ° C (according to the Recrystallize from alcohol. M.p. 113 ° C .;

Beispiel 9Example 9

Eine Mischung aus 78 Teilen p-Chlor-nitrobenzol, 95 Teilen Formanilid, 50 Teilen Kaliumcarbonat undA mixture of 78 parts of p-chloro-nitrobenzene, 95 parts of formanilide, 50 parts of potassium carbonate and

ίο \ Teil Kupferoxyd wird zusammen mit 80 Teilen Xylol 8 Stunden auf 180° C erhitzt. Dabei wird das während der Reaktion entstehende Wasser durch azeotrope Destillation laufend aus dem Reaktionsgemisch entfernt. Nach beendeter Reaktion werden das Lösungsmittel und nicht umgesetzte Ausgangsstoffe mit Wasserdampf abgetrieben. Es hinterbleiben 107 Teile 4-Nitro-diphenylamin.ίο \ part of copper oxide is heated to 180 ° C for 8 hours together with 80 parts of xylene. The water formed during the reaction is continuously removed from the reaction mixture by azeotropic distillation. After the reaction has ended, the solvent and unreacted starting materials are driven off with steam. 107 parts of 4-nitro-diphenylamine remain.

Claims (3)

Patentansprüche. aoClaims. ao 1. Verfahren zur Herstellung von 4-Nitrodiarylaminen, dadurch gekennzeichnet, daß man gegebenenfalls substituierte p-Halogennitrobenzole mit gegebenenfalls substituierten, am Stickstoff acylierten Arylaminen umsetzt.1. Process for the preparation of 4-nitrodiarylamines, characterized in that one optionally substituted p-halonitrobenzenes with optionally substituted arylamines acylated on nitrogen. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man in Gegenwart von säurebindenden Mitteln arbeitet.2. The method according to claim 1, characterized in that one is in the presence of acid-binding Means works. 3. Ausführungsform des Verfahrens nach An-Spruch 1 und 2, dadurch gekennzeichnet, daß man die am Stickstoff acylierten Arylamine erst im Reaktionsgemisch erzeugt.3. embodiment of the method according to claim 1 and 2, characterized in that one the arylamines acylated on nitrogen are only generated in the reaction mixture. Die Bestimmung des anorganisch gebundenen Chlors ergab einen Umsatz von 55°/o der Theorie.The determination of the inorganically bound chlorine showed a conversion of 55% of theory. Beispiel 5Example 5 Eine Mischung aus 78 Teilen p-Chlor-nitrobenzol, 105 Teilen Form-p-toluidid, 40 Teilen Kaliumcarbonat und 1 Teil Kupferoxyd wird 5 Stunden auf 200° C erhitzt, nach dem Abkühlen auf 80° C mit 150 Teilen Benzol verdünnt und noch heiß filtriert. Aus der Lösung scheiden sich beim Abkühlen 55 Teile 4-Nitro-4'-methyl-diphenylamin ab. Ähnliche Ergebnisse werden bei Verwendung von Form-o-toluidid erzielt.A mixture of 78 parts of p-chloro-nitrobenzene, 105 parts of form-p-toluidide, 40 parts of potassium carbonate and 1 part of copper oxide is heated to 200 ° C for 5 hours, after cooling to 80 ° C with 150 parts Diluted benzene and filtered while hot. On cooling, 55 parts of 4-nitro-4'-methyl-diphenylamine separate from the solution away. Similar results are obtained using form-o-toluidide. Beispiel 6Example 6 Eine Mischung aus 78 Teilen p-Chlor-nitrobenzol, 128 Teilen Form-crnaphthalid, 40 Teilen Kaliumcarbonat und 1 Teil Kupferoxyd wird 5 Stunden auf 2000C erhitzt, nach dem Abkühlen auf 8O0C mit 150 Teilen Benzol verdünnt und noch heiß filtriert. Aus dem Filtrat kristallisieren 85 Teile N-(4-Nitrophenyl)-a-naphthylamin aus. F. 164 bis 167° C (nach dem Umkristallisieren aus Xylol F. 173 bis 174° C).A mixture of 78 parts of p-chloro-nitrobenzene, 128 parts of the form-crnaphthalid, 40 parts of potassium carbonate and 1 part of cupric oxide is heated for 5 hours at 200 0 C, after cooling to 8O 0 C diluted with 150 parts of benzene and filtered hot. 85 parts of N- (4-nitrophenyl) -a-naphthylamine crystallize out from the filtrate. Mp 164 to 167 ° C (after recrystallization from xylene mp 173 to 174 ° C). Beispiel 7Example 7 Eine Mischung aus 78 Teilen p-Chlor-nitrobenzol, 63 Teilen p-Nitroformanilid, 40 Teilen Kaliumcarbonat und 1 Teil Kupferoxyd wird in 250 Teilen Nitrobenzol 5 Stunden auf 200° C erhitzt und die Lösung dann noch heiß von den anorganischen Salzen abnitriert. Aus dem Filtrat kristallisieren beim Abkühlen 17 Teile 4,4'-Dinitro-diphenylamin.A mixture of 78 parts of p-chloro-nitrobenzene, 63 parts of p-nitroformanilide, 40 parts of potassium carbonate and 1 part of copper oxide is heated in 250 parts of nitrobenzene at 200 ° C for 5 hours and the The solution is then nitrated from the inorganic salts while it is still hot. Crystallize from the filtrate on cooling 17 parts of 4,4'-dinitro-diphenylamine. Beispiel 8Example 8 Eine Mischung aus 95 Teilen l,2-Dichlor-4-nitro- In Betracht gezogene Druckschriften:A mixture of 95 parts of 1,2-dichloro-4-nitro- Publications considered: benzol, 95 Teilen Formanilid, 40 Teilen Kaliumcar- 35 Beilstein, Handbuch der organischen Chemie, bonat und 1 Teil Kupferoxyd wird 5 Stunden auf 4. Auflage, Hptw. Bd. 12, S. 240.Benzene, 95 parts of formanilide, 40 parts of potassium carbonate 35 Beilstein, Handbuch der Organic Chemie, bonate and 1 part of copper oxide is 5 hours on 4th edition, Hptw. Vol. 12, p. 240. ® 909 509/436 4. 59® 909 509/436 4. 59
DEF21782A 1956-11-29 1956-11-29 Process for the preparation of 4-nitro-diarylamines Pending DE1056619B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF21782A DE1056619B (en) 1956-11-29 1956-11-29 Process for the preparation of 4-nitro-diarylamines

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEF21782A DE1056619B (en) 1956-11-29 1956-11-29 Process for the preparation of 4-nitro-diarylamines
GB5482/59A GB855719A (en) 1959-02-17 1959-02-17 Process for the production of 4-nitro-diarylamines

Publications (1)

Publication Number Publication Date
DE1056619B true DE1056619B (en) 1959-05-06

Family

ID=25973999

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF21782A Pending DE1056619B (en) 1956-11-29 1956-11-29 Process for the preparation of 4-nitro-diarylamines

Country Status (1)

Country Link
DE (1) DE1056619B (en)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4140716A (en) * 1978-01-05 1979-02-20 Monsanto Company Process for making an amide of formic acid and forming nitrodiarylamine therefrom
FR2409979A1 (en) * 1977-11-23 1979-06-22 Monsanto Co PROCESS FOR PREPARING NITRODIARYLAMINES AND NEW PRODUCTS THUS OBTAINED
DE2855762A1 (en) * 1977-12-27 1979-06-28 Monsanto Co METHOD OF PRODUCING NITRODIARYLAMINE USING A PROTON ABSTRACTOR AND A PROMOTOR
DE2855764A1 (en) * 1977-12-27 1979-06-28 Monsanto Co METHOD OF PRODUCING NITRODIARYLAMINE USING A PROMOTOR
FR2419277A1 (en) * 1978-03-08 1979-10-05 Goodyear Tire & Rubber PROCESS FOR PREPARING PARA-NITRODIPHENYLAMINES
US4196146A (en) * 1978-03-13 1980-04-01 Monsanto Company Making nitrodiarylamines from formyl derivatives of aromatic amines and nitrohaloarenes by admixing with certain aqueous salt solutions
US4228103A (en) * 1978-03-13 1980-10-14 Monsanto Company Effecting condensation of nitrohaloarene and formyl derivative of a primary aromatic amine with alkali metal hydroxide
DE3246151A1 (en) * 1982-12-14 1984-06-14 Bayer Ag, 5090 Leverkusen Process for the preparation of 4-nitrodiphenylamines
EP0203878A1 (en) * 1985-05-20 1986-12-03 The Goodyear Tire & Rubber Company Para-nitrodiphenylamine synthesis
US6462034B1 (en) 1998-04-03 2002-10-08 Theravance, Inc. Local anesthetic compounds and uses
US6576791B1 (en) * 1998-04-03 2003-06-10 Theravance, Inc. Local anesthetic compounds and uses
EP1593665A1 (en) * 2003-02-10 2005-11-09 Idemitsu Kosan Co., Ltd. Method for producing aromatic diamine derivative

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2409979A1 (en) * 1977-11-23 1979-06-22 Monsanto Co PROCESS FOR PREPARING NITRODIARYLAMINES AND NEW PRODUCTS THUS OBTAINED
US4209463A (en) * 1977-12-27 1980-06-24 Monsanto Company Promoting the formation of nitrodiarylamines from nitrohaloarenes, activated aryl amines and sodium carbonates
DE2855762A1 (en) * 1977-12-27 1979-06-28 Monsanto Co METHOD OF PRODUCING NITRODIARYLAMINE USING A PROTON ABSTRACTOR AND A PROMOTOR
DE2855764A1 (en) * 1977-12-27 1979-06-28 Monsanto Co METHOD OF PRODUCING NITRODIARYLAMINE USING A PROMOTOR
US4187249A (en) * 1977-12-27 1980-02-05 Monsanto Company Promoting the reaction of sodium salts of formyl derivatives of aromatic amines to form nitrodiarylamines
US4140716A (en) * 1978-01-05 1979-02-20 Monsanto Company Process for making an amide of formic acid and forming nitrodiarylamine therefrom
FR2419277A1 (en) * 1978-03-08 1979-10-05 Goodyear Tire & Rubber PROCESS FOR PREPARING PARA-NITRODIPHENYLAMINES
US4196146A (en) * 1978-03-13 1980-04-01 Monsanto Company Making nitrodiarylamines from formyl derivatives of aromatic amines and nitrohaloarenes by admixing with certain aqueous salt solutions
US4228103A (en) * 1978-03-13 1980-10-14 Monsanto Company Effecting condensation of nitrohaloarene and formyl derivative of a primary aromatic amine with alkali metal hydroxide
DE3246151A1 (en) * 1982-12-14 1984-06-14 Bayer Ag, 5090 Leverkusen Process for the preparation of 4-nitrodiphenylamines
EP0203878A1 (en) * 1985-05-20 1986-12-03 The Goodyear Tire & Rubber Company Para-nitrodiphenylamine synthesis
US6462034B1 (en) 1998-04-03 2002-10-08 Theravance, Inc. Local anesthetic compounds and uses
US6576791B1 (en) * 1998-04-03 2003-06-10 Theravance, Inc. Local anesthetic compounds and uses
EP1593665A1 (en) * 2003-02-10 2005-11-09 Idemitsu Kosan Co., Ltd. Method for producing aromatic diamine derivative
EP1593665A4 (en) * 2003-02-10 2007-04-04 Idemitsu Kosan Co Method for producing aromatic diamine derivative

Similar Documents

Publication Publication Date Title
DE1056619B (en) Process for the preparation of 4-nitro-diarylamines
DE1518307B1 (en) Process for the preparation of nitrodiarylamines
EP0057871B1 (en) Process for the preparation of optionally p-chloro-substituted 2,6-diamino toluene
DE2232446C3 (en) Process for the preparation of pure 1-nitroanthraquinone
DE3501698A1 (en) METHOD FOR PRODUCING 4-NITRODIPHENYLAMINE
DE2453529A1 (en) PROCESS FOR THE MANUFACTURING OF NITRONAPHTHALINES
EP0075174A1 (en) Process for the preparation of 4-nitrodiphenyl amines
DE3836175A1 (en) FLUOR CONTAINING PHENOLES
EP0057889B1 (en) Process for preparing 1-alkyl-2-chloro-5-nitro-benzene-4-sulphonic acids
DE2558517C2 (en) Process for the preparation of isopropyl 4-methyl-imidazole-5-carboxylate
EP0057861A2 (en) Process for the preparation of nitroanilines
DE3246151C2 (en)
EP0481316B1 (en) Process for the preparation of 2,2,-bis(aminophenyl)-propane
US4506089A (en) Preparation of methyl m-nitrobenzoate
DE2349708C2 (en) Process for the preparation of aminoanthraquinones
DE1643329B2 (en) PROCESS FOR THE PRODUCTION OF NITROAMINODIARYLAETHERS
EP0128453A2 (en) Process for preparing fluorophthalic-acid imides
DE3605197A1 (en) METHOD FOR PRODUCING 4-NITRODIPHENYLAMINE
EP0173202A2 (en) Process for the preparation of chloro-o-nitroanilines
DE2117050C3 (en) Process for the preparation of 1- (5-nitrothiazol-2-yl) -2-oxotetrahydroimidazole
DE1090225B (en) Process for the preparation of p-nitrodiphenylamines
US2765348A (en) Process for the separation of 2, 6-dinitrotoluene from its admixture with 2, 4-dinitrotoluene
DE953069C (en) Process for the preparation of aliphatic, cycloaliphatic and araliphatic nitroso compounds
EP0129615B1 (en) Process for the preparation of bromoanthraquinones
EP0046859A1 (en) Process for the preparation of 1-bromo-3,5-dichlorobenzene