GB935303A - Improved process for the manufacture of 4-aminodiphenylamine - Google Patents

Improved process for the manufacture of 4-aminodiphenylamine

Info

Publication number
GB935303A
GB935303A GB253/61A GB25361A GB935303A GB 935303 A GB935303 A GB 935303A GB 253/61 A GB253/61 A GB 253/61A GB 25361 A GB25361 A GB 25361A GB 935303 A GB935303 A GB 935303A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
solvent
reaction
pressure
added
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
GB253/61A
Inventor
Cyril Gardner
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB253/61A priority Critical patent/GB935303A/en
Publication of GB935303A publication Critical patent/GB935303A/en
Expired 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
    • 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
    • C07C211/54—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 two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups

Landscapes

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

Abstract

4-Aminodiphenylamine is produced by the reduction of 4-nitrosodiphenylamine with hydrogen in the presence of a catalyst suspended in an organic solvent, the 4-nitrosodiphenylamine being added to the hydrogenation vessel at such a rate that it is never in excess of the amount of it that will completely dissolve in the reaction mixture present in the hydrogenation vessel. It is desirable that further solvent is added to the vessel as the p reaction proceeds to prevent unduly high concentrations of nitroso and amino compounds occurring in the reaction mixture. The solvent may be methanol, ethanol, isopropanol, n-butanol, benzene, toluene or dioxan. The reaction is carried out at a temperature between 15 DEG -110 DEG C.; preferably between 60 DEG -90 DEG C. Catalysts specified are nickel, cobalt, platinum and palladium, either in powder form or deposited on alumina, kieselguhr or carbon. The pressure of hydrogen used may be from atmospheric pressure upwards, and hydrogen is added throughout the reaction to maintain the chosen pressure. One example is given illustrating the process, using isopropanol as the solvent, palladium on carbon as the catalyst, a temperature of 80 DEG C., and hydrogen at a pressure of 40 p.s.i.
GB253/61A 1961-01-03 1961-01-03 Improved process for the manufacture of 4-aminodiphenylamine Expired GB935303A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB253/61A GB935303A (en) 1961-01-03 1961-01-03 Improved process for the manufacture of 4-aminodiphenylamine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB253/61A GB935303A (en) 1961-01-03 1961-01-03 Improved process for the manufacture of 4-aminodiphenylamine

Publications (1)

Publication Number Publication Date
GB935303A true GB935303A (en) 1963-08-28

Family

ID=9701129

Family Applications (1)

Application Number Title Priority Date Filing Date
GB253/61A Expired GB935303A (en) 1961-01-03 1961-01-03 Improved process for the manufacture of 4-aminodiphenylamine

Country Status (1)

Country Link
GB (1) GB935303A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4313002A (en) * 1980-10-29 1982-01-26 Uop Inc. Preparation of p-aminodiphenylamines
EP0590053B2 (en) † 1991-06-21 2006-04-12 Flexsys America L.P. Method of preparing 4-aminodiphenylamine

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4313002A (en) * 1980-10-29 1982-01-26 Uop Inc. Preparation of p-aminodiphenylamines
EP0590053B2 (en) † 1991-06-21 2006-04-12 Flexsys America L.P. Method of preparing 4-aminodiphenylamine

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