GB799871A - Hydrogenation catalysts and process - Google Patents
Hydrogenation catalysts and processInfo
- Publication number
- GB799871A GB799871A GB12826/56A GB1282656A GB799871A GB 799871 A GB799871 A GB 799871A GB 12826/56 A GB12826/56 A GB 12826/56A GB 1282656 A GB1282656 A GB 1282656A GB 799871 A GB799871 A GB 799871A
- Authority
- GB
- United Kingdom
- Prior art keywords
- palladium
- solution
- reduced
- chloride
- catalyst
- 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
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- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/42—Platinum
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Organic nitro compounds are reduced to amino compounds in the presence of a hydrogenation catalyst comprising 0.1 to 10 per cent by weight of platinum and/or palladium deposited on the surface of an oleophilic carbon support having an oil absorption factor of at least about 200 (see Group III). In examples: (a) an aqueous solution of 2,4-dinitrotoluene is reduced with hydrogen under pressure to 2,4-diaminotoluene in the presence of a palladium catalyst; (b) nitrobenzene is reduced at 140-160 DEG C. and a hydrogen pressure of 200-1000 p.s.i.g. to form aniline in the presence of a palladium or palladium-iron catalyst; (c) 2,6-dinitrotoluene is reduced by hydrogen to 2,6-diaminotoluene, using a water slurry of palladium-iron catalyst; (d) 2-nitropropane is reduced to 2-aminopropane at 75 DEG C. under hydrogen pressure of 500 p.s.i.g. in the presence of an aqueous slurry of palladium-iron catalyst; (e) nitrobenzene is reduced to aniline at above 170 DEG C. at a hydrogen pressure of 250 p.s.i.g. in the presence of a palladium-iron catalyst, the reaction mixture being maintained water-free; (f) nitrocyclohexane is reduced by hydrogen to cyclohexylamine at 70 DEG C. and 500 p.s.i.g. pressure in the presence of platinum-palladium-iron catalyst; (g) nitrocyclohexane is reduced by hydrogen to cyclohexylamine and cyclohexanone oxime at 125 DEG C. and 250 p.s.i.g. pressure in the presence of a palladium-iron catalyst; (h) 2,4-dinitrotoluene is reduced to 2,4-diaminotoluene at 125-150 DEG C. and a hydrogen pressure of 400 p.s.i.g. in the presence of a palladium-iron catalyst; (i) nitrobenzene is reduced by hydrogen to a mixture of p-aminophenol and aniline at 100 DEG C. in the presence of a platinum catalyst, C-cetyl betaine, and sulphuric acid; (j) trinitrotoluene is reduced with hydrogen at 25-30 DEG C. in the presence of a platinum-palladium-iron catalyst to form triaminotoluene. Other reductions referred to are b -nitronaphthalene to b -aminonaphthalene, p-nitroanisole to p-anisidine, the sodium salt of dinitrostilbene disulphonic acid to the corresponding diaminostilbene compound, the sodium salt of p-nitrobenzoic acid to p-aminobenzoic acid, and 5-nitroquinoline in methanol to 5-aminoquinoline.ALSO:A hydrogenation catalyst comprises 0.1 to 10 per cent by weight of platinum and/or palladium deposited on the surface of an oleophilic carbon support having an oil absorption factor of at least about 200. The catalyst may be activated with minor amounts of an oxide, hydroxide, or carbonate of iron, nickel, cobalt, magnesium, aluminium, manganese, chromium, vanadium or tungsten, or fluorides of boron and/or silicon. The carbon support is preferably non-porous, with a surface area of 20-100 square meters per gm.; acetylene black is suitable. In examples of the preparation of the catalyst, (a) a solution of sodium bicarbonate is added to an aqueous slurry of acetylene black, followed by a solution of palladium chloride or chloroplatinic acid; the mixture is heated to 95 DEG C., reduced with formaldehyde solution, cooled, filtered, and washed; (b) acetylene black, sodium bicarbonate, platinous potassium chloride, and water are stirred at 95 DEG C., and the paste is filtered and reduced with hydrogen; (c) a solution of ferric chloride is added to an aqueous suspension of acetylene black, followed by a sodium carbonate solution to precipitate basic iron carbonate; sodium bicarbonate solution and palladium chloride solution are then added, and the mixture heated and reduced with formaldehyde; the ferric chloride and sodium carbonate solutions may be replaced by solutions of magnesium sulphate and sodium hydroxide to form a magnesium-containing catalyst; (d) ferric chloride solution and sodium bicarbonate solution are mixed to precipitate basic ferric carbonate and then a mixture of palladium chloride solution and sodium bicarbonate solution is added, followed by acetylene black; (e) sodium bicarbonate is added to a suspension of acetylene black, followed by solutions of palladium chloride and ferric chloride; (b) a solution containing palladium chloride and ferrous chloride is added to a mixture of acetylene black, sodium bicarbonate, and water; (g) palladium chloride is added to a solution of sodium chloride and stirred to form a chloropalladite solution; water, ferric chloride, and acetylene black are then added, followed by sodium bicarbonate; (h) acetylene black is stirred with sodium bicarbonate solution, and a solution of ferric or ferrous chloride added, followed by a solution of palladium chloride and chloroplatinic acid; (i) palladium chloride and chloroplatinic acid are added to a sodium chloride solution, followed by ferric chloride solution and carbon black; sodium bicarbonate is then added. Catalyst containing a smaller amount of active metal may be prepared by dilution of a concentrate with more of the carrier. Reducing agents other than formaldehyde and hydrogen which may be used are glucose, hydrazine, alcohol, and glycerine. The catalysts may be used in the reduction of organic nitro compounds to amino compounds (see Group IV (b)).
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US799871XA | 1955-05-10 | 1955-05-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB799871A true GB799871A (en) | 1958-08-13 |
Family
ID=22154073
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB12826/56A Expired GB799871A (en) | 1955-05-10 | 1956-04-26 | Hydrogenation catalysts and process |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB799871A (en) |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996036597A1 (en) * | 1995-05-19 | 1996-11-21 | Novartis Ag | Process for the catalytic hydrogenation of aromatic nitro compounds |
US5783514A (en) * | 1992-03-26 | 1998-07-21 | Henkel Kommanditgesellschaft Auf Aktien | Shell catalyst, a process for its production and its use |
US5962741A (en) * | 1996-11-19 | 1999-10-05 | Novartis Ag | Process for the production of aromatic halogen-amino compounds |
US6258982B1 (en) | 1996-09-23 | 2001-07-10 | Novartis Ag | Process for the preparation of substituted aromatic amino compounds |
CN101823972A (en) * | 2010-05-05 | 2010-09-08 | 江苏利田科技有限公司 | Process for cleanly producing o (p) - aminoanisole (phenetidine) by coupling simulated moving bed |
CN102952022A (en) * | 2012-09-13 | 2013-03-06 | 赛鼎工程有限公司 | Method for continuously preparing tolylenediamine by utilizing dinitrotoluene, catalyst used in method and preparation method of catalyst |
CN105237434A (en) * | 2015-10-29 | 2016-01-13 | 中石化南京工程有限公司 | Method for producing cyclohexanone oxime |
CN106699611A (en) * | 2016-12-30 | 2017-05-24 | 沈阳化工研究院有限公司 | Production method for preparing sodium m-aminobenzene sulfonate by means of continuous hydrogenation reduction |
CN106977406A (en) * | 2017-03-10 | 2017-07-25 | 江苏华达化工集团有限公司 | The method of continuous autoclave catalytic hydrogenation synthesizing amino naphthalene |
CN107986973A (en) * | 2017-12-08 | 2018-05-04 | 西安近代化学研究所 | A kind of preparation method of 2,4,6- triaminotoluenes hydrochloride |
CN110624571A (en) * | 2019-09-27 | 2019-12-31 | 西安凯立新材料股份有限公司 | Catalyst for synthesizing 3, 5-dichloroaniline and preparation method and application thereof |
CN112076745A (en) * | 2020-09-21 | 2020-12-15 | 中北大学 | High-efficiency palladium-carbon catalyst and preparation method thereof |
CN113145112A (en) * | 2021-04-30 | 2021-07-23 | 福州大学 | Preparation method of Pd-Pt/C catalyst for selective hydrogenation of dinitrotoluene |
CN114471544A (en) * | 2022-02-25 | 2022-05-13 | 天脊煤化工集团股份有限公司 | Catalyst and application thereof in aniline preparation |
CN115501886A (en) * | 2022-03-31 | 2022-12-23 | 西南民族大学 | Preparation method of catalyst for synthesizing aniline by hydrogenation of nitrobenzene at low temperature |
-
1956
- 1956-04-26 GB GB12826/56A patent/GB799871A/en not_active Expired
Cited By (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5783514A (en) * | 1992-03-26 | 1998-07-21 | Henkel Kommanditgesellschaft Auf Aktien | Shell catalyst, a process for its production and its use |
WO1996036597A1 (en) * | 1995-05-19 | 1996-11-21 | Novartis Ag | Process for the catalytic hydrogenation of aromatic nitro compounds |
US6096924A (en) * | 1995-05-19 | 2000-08-01 | Novartis Ag | Process for the catalytic hydrogeneration of aromatic nitro compounds |
US6258982B1 (en) | 1996-09-23 | 2001-07-10 | Novartis Ag | Process for the preparation of substituted aromatic amino compounds |
US5962741A (en) * | 1996-11-19 | 1999-10-05 | Novartis Ag | Process for the production of aromatic halogen-amino compounds |
US6197716B1 (en) | 1996-11-19 | 2001-03-06 | Novartis Ag | Process for the production of aromatic halogen-amino compounds |
CN101823972A (en) * | 2010-05-05 | 2010-09-08 | 江苏利田科技有限公司 | Process for cleanly producing o (p) - aminoanisole (phenetidine) by coupling simulated moving bed |
CN101823972B (en) * | 2010-05-05 | 2015-03-25 | 江苏利田科技股份有限公司 | Process for cleanly producing o (p) - aminoanisole (phenetidine) by coupling simulated moving bed |
CN102952022A (en) * | 2012-09-13 | 2013-03-06 | 赛鼎工程有限公司 | Method for continuously preparing tolylenediamine by utilizing dinitrotoluene, catalyst used in method and preparation method of catalyst |
CN102952022B (en) * | 2012-09-13 | 2014-04-09 | 赛鼎工程有限公司 | Method for continuously preparing tolylenediamine by utilizing dinitrotoluene, catalyst used in method and preparation method of catalyst |
CN105237434A (en) * | 2015-10-29 | 2016-01-13 | 中石化南京工程有限公司 | Method for producing cyclohexanone oxime |
CN106699611A (en) * | 2016-12-30 | 2017-05-24 | 沈阳化工研究院有限公司 | Production method for preparing sodium m-aminobenzene sulfonate by means of continuous hydrogenation reduction |
CN106977406A (en) * | 2017-03-10 | 2017-07-25 | 江苏华达化工集团有限公司 | The method of continuous autoclave catalytic hydrogenation synthesizing amino naphthalene |
CN107986973A (en) * | 2017-12-08 | 2018-05-04 | 西安近代化学研究所 | A kind of preparation method of 2,4,6- triaminotoluenes hydrochloride |
CN110624571A (en) * | 2019-09-27 | 2019-12-31 | 西安凯立新材料股份有限公司 | Catalyst for synthesizing 3, 5-dichloroaniline and preparation method and application thereof |
CN110624571B (en) * | 2019-09-27 | 2022-07-05 | 西安凯立新材料股份有限公司 | Catalyst for synthesizing 3, 5-dichloroaniline and preparation method and application thereof |
CN112076745A (en) * | 2020-09-21 | 2020-12-15 | 中北大学 | High-efficiency palladium-carbon catalyst and preparation method thereof |
CN112076745B (en) * | 2020-09-21 | 2023-03-03 | 中北大学 | High-efficiency palladium-carbon catalyst and preparation method thereof |
CN113145112A (en) * | 2021-04-30 | 2021-07-23 | 福州大学 | Preparation method of Pd-Pt/C catalyst for selective hydrogenation of dinitrotoluene |
CN114471544A (en) * | 2022-02-25 | 2022-05-13 | 天脊煤化工集团股份有限公司 | Catalyst and application thereof in aniline preparation |
CN115501886A (en) * | 2022-03-31 | 2022-12-23 | 西南民族大学 | Preparation method of catalyst for synthesizing aniline by hydrogenation of nitrobenzene at low temperature |
CN115501886B (en) * | 2022-03-31 | 2023-10-24 | 西南民族大学 | Preparation method of catalyst for synthesizing aniline by hydrogenating nitrobenzene at low temperature |
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