GB768111A - Production of toluylene diamine - Google Patents

Production of toluylene diamine

Info

Publication number
GB768111A
GB768111A GB33032/54A GB3303254A GB768111A GB 768111 A GB768111 A GB 768111A GB 33032/54 A GB33032/54 A GB 33032/54A GB 3303254 A GB3303254 A GB 3303254A GB 768111 A GB768111 A GB 768111A
Authority
GB
United Kingdom
Prior art keywords
dinitrotoluene
methanol
toluylene diamine
atmospheres
toluylene
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
GB33032/54A
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
Publication of GB768111A publication Critical patent/GB768111A/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

Landscapes

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

Abstract

2 : 4- and 2 : 6-toluylene diamines are prepared by hydrogenating 2 : 4- and/or 2 : 6-dinitrotoluene in a continuous manner in the liquid phase at a temperature of from 80 DEG to 120 DEG C. and at a pressure above 50 atmospheres in the presence of Raney nickel. Methanol or ethanol may be used as a diluent. In place of the dinitrotoluene starting material, a mixture of dinitrotoluene and toluylene diamine may be used. In an embodiment of the invention, a solution of dinitrotoluene in methanol containing Raney nickel is continuously pumped co-currently with hydrogen through a reactor at a pressure of about 200 atmospheres and a temperature of from 80 DEG to 120 DEG C., the unused hydrogen being recycled. The methanol solvent is removed and the residue worked up by distillation. In a further embodiment, a eutectic mixture consisting approximately of 76 per cent dinitrotoluene and 24 per cent toluylene diamine diluted with methanol is hydrogenated. Eutectic mixtures may be obtained by mixing a calculated quantity of fresh dinitrotoluene and methanol with a portion of the aqueous methanolic solution of toluylene diamine obtained from a previous hydrogenation. Examples illustrate the continuous hydrogenation at 150-200 atmospheres and 100 DEG C. of (1) dinitrotoluene in methanol; and (2) a mixture of dinitrotoluene and recycled toluylene diamine in aqueous methanol.
GB33032/54A 1953-11-13 1954-11-15 Production of toluylene diamine Expired GB768111A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE768111X 1953-11-13

Publications (1)

Publication Number Publication Date
GB768111A true GB768111A (en) 1957-02-13

Family

ID=6673616

Family Applications (1)

Application Number Title Priority Date Filing Date
GB33032/54A Expired GB768111A (en) 1953-11-13 1954-11-15 Production of toluylene diamine

Country Status (1)

Country Link
GB (1) GB768111A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3154584A (en) * 1960-01-01 1964-10-27 Ici Ltd Process for the catalytic reduction of dinitrotoluenes
US5563296A (en) * 1993-07-15 1996-10-08 Bayer Aktiengesellschaft Continuous process for preparing aromatic amines
US5728880A (en) * 1996-03-05 1998-03-17 Bayer Aktiengesellschaft Process for the separation of high-boiling materials from the reaction mixture generated during the production of diaminotoluene
US7575660B2 (en) 2004-06-01 2009-08-18 Bayer Materialscience Ag Process for the distillative separation of aqueous amine solutions

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3154584A (en) * 1960-01-01 1964-10-27 Ici Ltd Process for the catalytic reduction of dinitrotoluenes
US5563296A (en) * 1993-07-15 1996-10-08 Bayer Aktiengesellschaft Continuous process for preparing aromatic amines
US5728880A (en) * 1996-03-05 1998-03-17 Bayer Aktiengesellschaft Process for the separation of high-boiling materials from the reaction mixture generated during the production of diaminotoluene
US7575660B2 (en) 2004-06-01 2009-08-18 Bayer Materialscience Ag Process for the distillative separation of aqueous amine solutions

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