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GB716239A - Improvements in and relating to the production of amines - Google Patents

Improvements in and relating to the production of amines

Info

Publication number
GB716239A
GB716239A GB1623/51A GB162351A GB716239A GB 716239 A GB716239 A GB 716239A GB 1623/51 A GB1623/51 A GB 1623/51A GB 162351 A GB162351 A GB 162351A GB 716239 A GB716239 A GB 716239A
Authority
GB
United Kingdom
Prior art keywords
water
sec
butyl
ketone
under pressure
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
GB1623/51A
Inventor
Stanley Ward
Sidney Arthur Lamb
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 GB1623/51A priority Critical patent/GB716239A/en
Publication of GB716239A publication Critical patent/GB716239A/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
    • C07C209/82—Purification; Separation; Stabilisation; Use of additives
    • C07C209/84—Purification
    • 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
    • C07C211/45—Monoamines
    • C07C211/46—Aniline
    • 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
    • C07C211/49—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 having at least two amino groups bound to the carbon skeleton
    • C07C211/50—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 having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton

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)

Abstract

The invention comprises a process for the preparation of N-alkylated aromatic amines by reaction of an aromatic amino-, nitro- or nitroamino-compound with a di-alkyl ketone containing at least four carbon atoms, and hydrogen, characterized in that there is recycled to the feed an aqueous distillation cut from the final product comprising the water/ketone azeotrope. The reductive alkylation is conducted at elevated temperature and preferably under pressure using a hydrogenation catalyst, and is particularly applicable for preparing N : N1-di-alkyl phenylene diamines. In examples: (1) p-nitraniline is dissolved in methyl ethyl ketone/water azeotrope, water layer separated and other layer pressure hydrogenated using palladium catalyst to yield N : N1-di-sec.-butyl-p-phenylene diamine; (2) the organic layer as in (1) is treated with recycled material and passed with hydrogen over copper chromite under pressure. The product upon distillation yields N : N1 - di - sec. - butyl p - phenylene diamine. m-Dinitrobenzene and p-phenylenediamine are also specified as starting materials. Specifications 621,749 and 712,100 are referred to.
GB1623/51A 1951-01-22 1951-01-22 Improvements in and relating to the production of amines Expired GB716239A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1623/51A GB716239A (en) 1951-01-22 1951-01-22 Improvements in and relating to the production of amines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1623/51A GB716239A (en) 1951-01-22 1951-01-22 Improvements in and relating to the production of amines

Publications (1)

Publication Number Publication Date
GB716239A true GB716239A (en) 1954-09-29

Family

ID=9725161

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1623/51A Expired GB716239A (en) 1951-01-22 1951-01-22 Improvements in and relating to the production of amines

Country Status (1)

Country Link
GB (1) GB716239A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3014967A (en) * 1957-01-11 1961-12-26 Monsanto Chemicals Preparation and hydrogenation of schiff's bases

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3014967A (en) * 1957-01-11 1961-12-26 Monsanto Chemicals Preparation and hydrogenation of schiff's bases

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