GB839420A - Improvements in process for preparing substituted diphenylamines - Google Patents

Improvements in process for preparing substituted diphenylamines

Info

Publication number
GB839420A
GB839420A GB27762/58A GB2776258A GB839420A GB 839420 A GB839420 A GB 839420A GB 27762/58 A GB27762/58 A GB 27762/58A GB 2776258 A GB2776258 A GB 2776258A GB 839420 A GB839420 A GB 839420A
Authority
GB
United Kingdom
Prior art keywords
nitrochlorobenzene
mols
mol
hours
hydrochloric 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.)
Expired
Application number
GB27762/58A
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.)
Uniroyal Inc
Original Assignee
United States Rubber Co
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 United States Rubber Co filed Critical United States Rubber Co
Publication of GB839420A publication Critical patent/GB839420A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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

Landscapes

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

Abstract

Compounds of the formula <FORM:0839420/IV (b)/1> where R2 represents hydrogen or an alkyl group and R1 represents hydrogen or an alkyl, alkoxy, aryloxy, halogen or nitro group, are prepared by reacting 1 mol. of p-nitrochlorobenzene with 1 to 9 mols. of a compound of the formula <FORM:0839420/IV (b)/2> in the presence of 1/2 to 1 mol. of potassium carbonate as the hydrochloric acid acceptor and a catalytic amount of a copper salt while maintaining the reaction mixture in an anhydrous condition by continuously distilling off all water present including that formed by the neutralization of the liberated hydrochloric acid by the potassium carbonate, the reaction being promoted by the addition of 1/20 to 2 mols. of dimethyl formamide or hexamethyl phosphoramide. The addition of the amide promotor is said to reduce the reaction time from 27 hours to as little as 3 hours. In the examples in which dimethyl formamide or hexamethyl phosphoramide are used with cuprous iodide as catalyst p-nitrochlorobenzene is condensed with aniline, p-toluidine, p-cumidine and p-nitroaniline. Specification 798,148 is referred to.
GB27762/58A 1957-11-05 1958-08-29 Improvements in process for preparing substituted diphenylamines Expired GB839420A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US839420XA 1957-11-05 1957-11-05

Publications (1)

Publication Number Publication Date
GB839420A true GB839420A (en) 1960-06-29

Family

ID=22181645

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27762/58A Expired GB839420A (en) 1957-11-05 1958-08-29 Improvements in process for preparing substituted diphenylamines

Country Status (1)

Country Link
GB (1) GB839420A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3270084A (en) * 1961-05-19 1966-08-30 Exxon Research Engineering Co Method of isomerizing olefins
US3313854A (en) * 1961-11-20 1967-04-11 Universal Oil Prod Co Preparation of para-nitrodiphenylamines utilizing a copper oxide catalyst
US4990673A (en) * 1988-11-18 1991-02-05 Hoechst Aktiengesellschaft Process for the preparation of 4,4'-dinitrodiphenylamine

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3270084A (en) * 1961-05-19 1966-08-30 Exxon Research Engineering Co Method of isomerizing olefins
US3313854A (en) * 1961-11-20 1967-04-11 Universal Oil Prod Co Preparation of para-nitrodiphenylamines utilizing a copper oxide catalyst
US4990673A (en) * 1988-11-18 1991-02-05 Hoechst Aktiengesellschaft Process for the preparation of 4,4'-dinitrodiphenylamine

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