GB768111A - Production of toluylene diamine - Google Patents
Production of toluylene diamineInfo
- 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
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.
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)
| 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 |
-
1954
- 1954-11-15 GB GB33032/54A patent/GB768111A/en not_active Expired
Cited By (4)
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1047101A (en) | Recovery of amines | |
| GB768111A (en) | Production of toluylene diamine | |
| GB1149251A (en) | Hydrogenation of nitrogenous carbon compounds | |
| GB821220A (en) | A process for the production of toluylene diamines | |
| Nishimura et al. | The ruthenium-catalyzed hydrogenation of aromatic amines promoted by lithium hydroxide | |
| GB924422A (en) | Production of hexamethylene diamine | |
| GB716239A (en) | Improvements in and relating to the production of amines | |
| GB568230A (en) | Improvements in or relating to the production of n.n -disecondary alkyl p-phenylene diamines | |
| GB729841A (en) | Elimination of colour-forming impurities from 1,4-butanediol | |
| GB1106088A (en) | Process for the preparation of phloroglucinol | |
| GB599016A (en) | Improvements in or relating to the production of ribitylaminobenzenes and triacyl derivatives thereof | |
| GB876013A (en) | Improvements in and relating to substituted tricyclodecanes | |
| US2175003A (en) | Process for the preparation of hexahydro-para-phenylene diamine | |
| ES251102A1 (en) | Process for preparing the amide of omega-aminocaprylic acid and amide product | |
| DE872343C (en) | Process for the production of n-propylamine | |
| DE954504C (en) | Process for the preparation of 1,2-diaminocyclohexane | |
| GB801534A (en) | A process for the preparation of an unsymmetrical dialkylhydrazine | |
| GB785108A (en) | Manufacture of hexahydrobenzylamine | |
| GB646594A (en) | Process for the preparation of dibenzylmethylamine and product obtained | |
| GB1095124A (en) | Bipiperidyl derivatives and processes for their preparation | |
| GB595459A (en) | Improvements in or relating to the preparation of olefinic alcohols from the corresponding acetylenic alcohols | |
| GB835643A (en) | N-aryl-n'-alicyclic-para-phenylene diamines | |
| GB742053A (en) | Production of heterocyclic compounds | |
| GB646750A (en) | Improvements in or relating to the preparation of ephedrine and salts thereof | |
| GB600426A (en) | Improvements in or relating to the production of p-methyl-amino-phenol |