DE1092025B - Process for the preparation of 4-nitro-2,6-di-tertiary-butylphenol - Google Patents

Process for the preparation of 4-nitro-2,6-di-tertiary-butylphenol

Info

Publication number
DE1092025B
DE1092025B DEF26260A DEF0026260A DE1092025B DE 1092025 B DE1092025 B DE 1092025B DE F26260 A DEF26260 A DE F26260A DE F0026260 A DEF0026260 A DE F0026260A DE 1092025 B DE1092025 B DE 1092025B
Authority
DE
Germany
Prior art keywords
butylphenol
tertiary
nitro
preparation
nitric acid
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
DEF26260A
Other languages
German (de)
Inventor
Dr Robert Seydel
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 DEF26260A priority Critical patent/DE1092025B/en
Priority to CH7538359A priority patent/CH387650A/en
Publication of DE1092025B publication Critical patent/DE1092025B/en
Pending 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
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • 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
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • 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
    • C07C201/16—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • 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
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
    • C07C205/20—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C07C205/21—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • 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

Landscapes

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

Description

DEUTSCHESGERMAN

Es ist bekannt, daß man 2,6-dialkylierte Phenole in konzentrierter Schwefelsäure mit Salpetersäure nitrieren kann, wobei man die entsprechenden 4-nitrosubstituierten Verbindungen erhält. Versucht man auf diese Weise jedoch, 2,6-di-tertiär-alkylierte Phenole zu nitrieren, so erhält man, wie aus der Literatur bekannt ist, nicht die entsprechenden 4-Nitroverbindungen, sondern an deren Stelle 2-tertiär-Alkyl-4,6-dinitrophenole. Es wird also eine tertiäre Alkylgruppe abgespalten und durch eine Nitrogruppe ersetzt. Dieselben 2-tertiär-Alkyl-4,6-dinitrophenole erhält man ebenfalls, wie aus der Literatur bekannt ist, aus den entsprechenden 2-tertiär-Alkylphenolen durch Nitrieren mit Salpetersäure.It is known that 2,6-dialkylated phenols in concentrated sulfuric acid can be nitrated with nitric acid, the corresponding 4-nitro-substituted Connections. If one tries in this way, however, to nitrate 2,6-di-tertiary-alkylated phenols, so As is known from the literature, one does not obtain the corresponding 4-nitro compounds, but different ones Place 2-tertiary-alkyl-4,6-dinitrophenols. So it is split off a tertiary alkyl group and replaced by a Nitro group replaced. The same 2-tertiary-alkyl-4,6-dinitrophenols are also obtained, as from the literature is known from the corresponding 2-tertiary-alkylphenols by nitrating with nitric acid.

Es wurde nun gefunden, daß man 4-Nitro-2,6-ditertiär-butylphenol dadurch herstellen kann, indem man 2,6-Di-tertiär-butylphenol in einem wasserunlöslichen organischen Lösungsmittel bei Temperaturen von 20 bis 60° C, vorzugsweise bei 50 bis 60° C, mit einer verdünnten wäßrigen Salpetersäure nitriert. Als wasserunlösliche organische Lösungsmittel werden besonders niedrig siedende aliphatische Kohlenwasserstoffe, wie Leichtbenzin oder Ligroin, verwendet. 4-Nitro-2,6-di-tertiärbutylphenol wird als Pflanzenschutzmittel und als Hilfsmittel in der Kautschukindustrie verwendet.It has now been found that 4-nitro-2,6-ditertiary-butylphenol can be prepared by 2,6-di-tert-butylphenol in a water-insoluble one organic solvent at temperatures of 20 to 60 ° C, preferably at 50 to 60 ° C, with a dilute aqueous nitric acid nitrated. As water-insoluble organic solvents are particularly low boiling aliphatic hydrocarbons, such as mineral spirits or ligroin, are used. 4-nitro-2,6-di-tertiary butylphenol is used as a pesticide and as an aid in the rubber industry.

Das folgende Beispiel erläutert das Verfahren der Erfindung.The following example illustrates the method of the invention.

Beispielexample

In einem Rührgefäß mit säurefester Auskleidung löst man 1648 Gewichtsteile 2,6-Di-tertiär-butylphenol in 1700 Volumteilen Leichtbenzin (Kp. = 60 bis 9O0C) und läßt zu dieser Lösung bei 50 bis 60° C unter anfänglichem Kühlen innerhalb von 3 Stunden 1940 Volumteile 30%ige Salpetersäure (Dichte bei 20°C = 1,185) fließen. Unter langsamem Abkühlen auf 20° C wird die Mischung noch 18 Stunden gerührt, und anschließend schleudert man das auskristallisierte Reaktionsprodukt ab, wäscht es Verfahren zur Herstellung
von 4-Nitro-2,6-ditertiär-butylphenolIn a stirred vessel with acid resistant lining 1648 parts by weight of 2,6-di-tert-butylphenol dissolved in 1,700 parts by volume of mineral spirits (Kp. = 60 to 9O 0 C) and allowed to this solution at 50 to 60 ° C under initial cooling within 3 Hours 1940 parts by volume of 30% nitric acid (density at 20 ° C = 1.185) flow. The mixture is stirred for a further 18 hours while slowly cooling to 20 ° C., and the reaction product which has crystallized out is then spun off and washed. Process for the preparation
of 4-nitro-2,6-di-tertiary-butylphenol

Anmelder:Applicant:

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

Dr. Robert Seydel, Köln-Dellbrück,
ist als Erfinder genannt wordenDr. Robert Seydel, Cologne-Dellbrück,
has been named as the inventor

mit Wasser aus und trocknet es an der Luft bei 80 bis 9O0C. Man erhält 1618 Gewichtsteile 4-Nitro-2,6-ditertiär-butylphenol vom F. = 1570C. Die Ausbeute beträgt 80,5% der Theorie.with water and dried in air at 80 to 9O 0 C. is obtained in 1618 parts by weight of 4-nitro-2,6-di-tertiary-butylphenol, mp = 157 0 C. The yield is 80.5% of theory.

Claims (1)

Patentanspruch:Claim: Verfahren zur Herstellung von 4-Nitro-2,6-ditertiär-butylphenol, dadurch gekennzeichnet, daß man 2,6-Di-tertiär-butylphenol in einem wasserunlöslichen organischen Lösungsmittel, besonders in einem aliphatischen Kohlenwasserstoff, bei Temperaturen von 20 bis 60° C, vorzugsweise bei 50 bis 60° C, mit einer verdünnten wäßrigen, vorzugsweise mit einer 30°/0igen Salpetersäure nitriert.Process for the preparation of 4-nitro-2,6-ditertiary-butylphenol, characterized in that 2,6-di-tertiary-butylphenol is mixed in a water-insoluble organic solvent, especially in an aliphatic hydrocarbon, at temperatures of 20 to 60 ° C , preferably nitrided at 50 to 60 ° C, with a dilute aqueous, preferably with a 30 ° / 0 nitric acid. In Betracht gezogene Druckschriften:Considered publications: USA.-Patentschrift Nr. 2 802 883;U.S. Patent No. 2,802,883; Journal of the Organic Chemistry, Bd. 21,1956, S. 1201 bis 1210;Journal of the Organic Chemistry, Vol. 21, 1956, p. 1201 to 1210; Journal of the American Chemical Society, Bd. 73,1951, S. 3179.Journal of the American Chemical Society, Vol. 73, 1951, P. 3179.
DEF26260A 1958-07-26 1958-07-26 Process for the preparation of 4-nitro-2,6-di-tertiary-butylphenol Pending DE1092025B (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DEF26260A DE1092025B (en) 1958-07-26 1958-07-26 Process for the preparation of 4-nitro-2,6-di-tertiary-butylphenol
CH7538359A CH387650A (en) 1958-07-26 1959-07-06 Process for making new pesticides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF26260A DE1092025B (en) 1958-07-26 1958-07-26 Process for the preparation of 4-nitro-2,6-di-tertiary-butylphenol

Publications (1)

Publication Number Publication Date
DE1092025B true DE1092025B (en) 1960-11-03

Family

ID=7091955

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF26260A Pending DE1092025B (en) 1958-07-26 1958-07-26 Process for the preparation of 4-nitro-2,6-di-tertiary-butylphenol

Country Status (1)

Country Link
DE (1) DE1092025B (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2802883A (en) * 1956-03-22 1957-08-13 Dow Chemical Co Preparation of 2-tertiary-alkyl-4, 6-dinitrophenols

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2802883A (en) * 1956-03-22 1957-08-13 Dow Chemical Co Preparation of 2-tertiary-alkyl-4, 6-dinitrophenols

Similar Documents

Publication Publication Date Title
EP0597361A1 (en) Process for the preparation of dinitrotoluene
DE2349753A1 (en) PROCESS FOR NITRATING AROMATIC COMPOUNDS
DE2400164C3 (en) Process for the separation of 1,5-dinitroanthraquinone and 1,8-dinitroanthraquinone from dinitro-anthraquinone mixtures
DE1056619B (en) Process for the preparation of 4-nitro-diarylamines
DE2234328A1 (en) PROCESS FOR NITRATING AROMATIC COMPOUNDS WITH AT LEAST ONE ORTHOPARA-ORIENTING SUBSTITUENT
DE1092025B (en) Process for the preparation of 4-nitro-2,6-di-tertiary-butylphenol
DE2453529A1 (en) PROCESS FOR THE MANUFACTURING OF NITRONAPHTHALINES
DE1016701B (en) Process for the preparation of cycloaliphatic nitrates
DE1150965B (en) Process for the continuous production of 1,5 and 1,8-dinitronaphthalene
DE954873C (en) Process for the preparation of Diaethylisonitrosomalonate
CH628019A5 (en) Process for preparing dichloronitroanilines
DE2557501C2 (en)
US1349802A (en) Process of manufacture of picric acid
DE4033099A1 (en) 2,2-Bis:(aminophenyl)-propane prodn. - by nitration of 2,2-di:phenyl-propane and redn. of resulting 2,2-bis:(nitrophenyl)-propane
DE1290531B (en) Process for the preparation of mixtures of isomeric mononitrotoluene with a relatively large proportion of p-nitrotoluene
DE1618109C (en) Method for the separation of 1.5 and 1.8 dinitronaphtha
DE2103360C (en)
DE1167843B (en) Process for the production of ª ‡ -nitrolactams
AT224649B (en) Process for the preparation of thiuram monosulfides
DE977654C (en) Process for the production of nitric acid esters of polyvinyl alcohol
DE875201C (en) Process for the preparation of substituted aryl vinyl sulfones
DE2438210A1 (en) METHOD OF NITRATING ANTHRAQUINONE AND ITS DERIVATIVES
DE939027C (en) Process for the preparation of N, N'-Dinitroso-N, N'-dialkylamides of aromatic dicarboxylic acids
AT213388B (en) Process for the preparation of new 3-nitro-azacyclo-alkanone-2-N-carbochlorides
AT162164B (en) Process for the preparation of α, α-di (nitrophenyl) -β, β, β-trichloroethanes.