GB805249A - Catalytic reduction of aromatic dinitro compounds - Google Patents
Catalytic reduction of aromatic dinitro compoundsInfo
- Publication number
- GB805249A GB805249A GB2790/57A GB279057A GB805249A GB 805249 A GB805249 A GB 805249A GB 2790/57 A GB2790/57 A GB 2790/57A GB 279057 A GB279057 A GB 279057A GB 805249 A GB805249 A GB 805249A
- Authority
- GB
- United Kingdom
- Prior art keywords
- per cent
- palladized
- nickel
- charcoal
- dinitro
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Aromatic diamines are prepared by reducing the corresponding dinitro compounds with hydrogen in the presence of a nickel or platinum metal hydrogenation catalyst, the process being characterized in that a solution of the dinitro compound, liquid at reaction temperature and pressure, is introduced into the hydrogenation zone, the solvent being one that will dissolve all the products of the reaction also, i.e. the diamine and the water, so that there is only one liquid phase in the hydrogenation zone throughout the whole reaction, the diamine being recovered from the solution when it has been removed from the hydrogenation zone. Specified solvents are morpholine, N-alkyl morpholines, butyrolactone, ethylenediamine, piperidine, N-alkyl piperidines, pyridine, N:N-dialkylamides, pyrollidone, methyl pyrollidone lower alkyl ethers of ethylene glycol and diethylene glycol and an aqueous solution of the aromatic diamines which are formed in the reduction containing about 15 to about 50 per cent of water. The invention also includes the reduction of aromatic dinitro compounds to the corresponding mononitro monoamino compounds. The reaction is carried out under conventional conditions for such reductions, i.e. 20-100 DEG C. and 25-150 lb./sq. inch gauge pressure. Specified catalysts are platinum black, platinum oxide, "Raney" nickel (Registered Trade Mark), palladized charcoal, platinized charcoal, nickel on kieselguhr or platinum or palladium on alumina. The reduction may be carried out batchwise or continuously. In examples: (i) m-dinitrobenzene is dissolved in m-phenylenediamine and water and reduced in the presence of 5 per cent palladized charcoal; (ii) as (i) using dimethylformamide; (iii) as (ii) but using nickel or kieselguhr; (iv) as (i) using the methyl ether of ethylene glycol and 10 per cent palladized charcoal; (v) as (iv) using pyrollidone; (vi) as (i) using butyrolactone; (vii) as (i) using methyl pyrollidone; (viii) as (i) using pyridine; (ix) as (ii) using 0.3 per cent palladized silica gel; (x) as (ix) using 0.5 per cent palladized alumina; (xi) as (ii) using a mixture of dinitrotoluenes; (xii) as (xi) using the ethyl ether of ethylene glycol and 1 per cent palladized charcoal; (xiii) as (iv) using "Raney" nickel; (xiv) as (iv) using 2:4-dinitro toluene and 5 per cent palladized charcoal; (xv) as (xiv) using o-dinitrobenzene; (xvi) as (xv) using a mixture of dinitrotoluenes; (xvii) as (xvi) using 0.5 per cent platinized alumina; (xviii) as (xv) using dinitroethylbenzene; (xix) m-dinitro benzene is reduced to m-nitroaniline using the methyl ether of ethylene glycol as solvent and a 10 per cent palladized charcoal catalyst.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US805249XA | 1956-02-06 | 1956-02-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB805249A true GB805249A (en) | 1958-12-03 |
Family
ID=22157938
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2790/57A Expired GB805249A (en) | 1956-02-06 | 1957-01-25 | Catalytic reduction of aromatic dinitro compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB805249A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3145231A (en) * | 1962-04-09 | 1964-08-18 | Du Pont | Process for the reduction of halo nitro aromatic compounds |
EP1518600A1 (en) * | 2003-09-29 | 2005-03-30 | Council of Scientific and Industrial Research | Improved nickel catalyst, process for the preparation thereof, process for hydrogenation of m-dinitrobenzene to m-phenylene diamine |
CN108164425A (en) * | 2017-12-29 | 2018-06-15 | 烟台安诺其精细化工有限公司 | The preparation method of m-phenylene diamine (MPD) |
-
1957
- 1957-01-25 GB GB2790/57A patent/GB805249A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3145231A (en) * | 1962-04-09 | 1964-08-18 | Du Pont | Process for the reduction of halo nitro aromatic compounds |
EP1518600A1 (en) * | 2003-09-29 | 2005-03-30 | Council of Scientific and Industrial Research | Improved nickel catalyst, process for the preparation thereof, process for hydrogenation of m-dinitrobenzene to m-phenylene diamine |
CN108164425A (en) * | 2017-12-29 | 2018-06-15 | 烟台安诺其精细化工有限公司 | The preparation method of m-phenylene diamine (MPD) |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3989756A (en) | Process for the production of halogenated aromatic primary amines | |
KR900016106A (en) | Reductive Amination of Carbonylnitrile and Similar Compounds | |
CA1127185A (en) | Toluene diamine from non-washed dinitrotoluene | |
CA1111449A (en) | Process for the preparation of 2,2'-dichloro- hydrazobenzene | |
US2894036A (en) | Catalytic reduction of aromatic polynitro compounds | |
GB964166A (en) | Process for the preparation of halogen substituted aromatic amines | |
GB805249A (en) | Catalytic reduction of aromatic dinitro compounds | |
KR850004093A (en) | Method for preparing tertiary amine | |
GB942963A (en) | Purification of butynediol | |
US3884936A (en) | Preparation of 2-pyrrolidone | |
EP0380840B1 (en) | Method of preparing 2-phenylbenzotriazoles | |
GB1092027A (en) | Process of preparing cyclohexylhydroxylamine | |
US2109159A (en) | Process for preparing furfurylamines | |
Brown et al. | Hydrogenation of nitroaromatics in the presence of the new platinum metal and carbon-supported platinum metal catalysts | |
US3361818A (en) | Process for preparing aminated benzenes from aminated cyclohexanes | |
GB940305A (en) | Catalytic reduction of aromatic mononitro compounds | |
ES478478A1 (en) | Process for the preparation of p-amino-diphenylamine | |
US3019262A (en) | Nu-benzyl-n'-phenyl-p-phenylenediamine and its manufacture | |
US4069240A (en) | Nuclear hydrogenation of n-aryl carbamates | |
US3061644A (en) | Process for producing ethylenediamine or derivatives thereof | |
US3260750A (en) | Process for preparing hydrazobenzenes | |
US3150185A (en) | Hydrogenation of nitrohaloaromatic compounds | |
US3232989A (en) | Aromatic dinitro compounds | |
US3297769A (en) | Preparation of 1-nitroparaffins from 1-nitroolefins by catalytic hydrogenation | |
GB1009024A (en) | Process for preparing aminophenols |