GB786407A - Process for the catalytic hydrogenation of organic nitro compounds - Google Patents
Process for the catalytic hydrogenation of organic nitro compoundsInfo
- Publication number
- GB786407A GB786407A GB13152/56A GB1315256A GB786407A GB 786407 A GB786407 A GB 786407A GB 13152/56 A GB13152/56 A GB 13152/56A GB 1315256 A GB1315256 A GB 1315256A GB 786407 A GB786407 A GB 786407A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon
- diluted
- concentration
- noble metal
- per cent
- 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
- 150000002828 nitro derivatives Chemical class 0.000 title abstract 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 239000003054 catalyst Substances 0.000 abstract 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 6
- 229910052799 carbon Inorganic materials 0.000 abstract 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 4
- 229910000510 noble metal Inorganic materials 0.000 abstract 4
- -1 "Furnace Blacks Natural products 0.000 abstract 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 abstract 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 abstract 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 2
- 239000005909 Kieselgur Substances 0.000 abstract 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 238000010521 absorption reaction Methods 0.000 abstract 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 2
- 239000004411 aluminium Substances 0.000 abstract 2
- 229910052782 aluminium Inorganic materials 0.000 abstract 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 2
- 229910052796 boron Inorganic materials 0.000 abstract 2
- 229910052804 chromium Inorganic materials 0.000 abstract 2
- 239000011651 chromium Substances 0.000 abstract 2
- 229910017052 cobalt Inorganic materials 0.000 abstract 2
- 239000010941 cobalt Substances 0.000 abstract 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 2
- 150000002222 fluorine compounds Chemical class 0.000 abstract 2
- 150000004679 hydroxides Chemical class 0.000 abstract 2
- 229910052742 iron Inorganic materials 0.000 abstract 2
- 229910052749 magnesium Inorganic materials 0.000 abstract 2
- 239000011777 magnesium Substances 0.000 abstract 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 229910052759 nickel Inorganic materials 0.000 abstract 2
- 239000003921 oil Substances 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- 229910052710 silicon Inorganic materials 0.000 abstract 2
- 239000010703 silicon Substances 0.000 abstract 2
- 239000000377 silicon dioxide Substances 0.000 abstract 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 abstract 2
- 229910052721 tungsten Inorganic materials 0.000 abstract 2
- 239000010937 tungsten Substances 0.000 abstract 2
- 229910052720 vanadium Inorganic materials 0.000 abstract 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 abstract 2
- ZUTCJXFCHHDFJS-UHFFFAOYSA-N 1,5-dinitronaphthalene Chemical compound C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1[N+]([O-])=O ZUTCJXFCHHDFJS-UHFFFAOYSA-N 0.000 abstract 1
- QHLAKKDTFVJHAJ-UHFFFAOYSA-N 3-(1,2-dinitro-2-phenylethenyl)benzene-1,2-disulfonic acid Chemical compound [N+](=O)([O-])C(=C(C1=C(C(=CC=C1)S(=O)(=O)O)S(=O)(=O)O)[N+](=O)[O-])C1=CC=CC=C1 QHLAKKDTFVJHAJ-UHFFFAOYSA-N 0.000 abstract 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 abstract 1
- NDDZXHOCOKCNBM-UHFFFAOYSA-N 5-nitroquinoline Chemical compound C1=CC=C2C([N+](=O)[O-])=CC=CC2=N1 NDDZXHOCOKCNBM-UHFFFAOYSA-N 0.000 abstract 1
- BNUHAJGCKIQFGE-UHFFFAOYSA-N Nitroanisol Chemical compound COC1=CC=C([N+]([O-])=O)C=C1 BNUHAJGCKIQFGE-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229960004050 aminobenzoic acid Drugs 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 abstract 1
- NJNQUTDUIPVROZ-UHFFFAOYSA-N nitrocyclohexane Chemical compound [O-][N+](=O)C1CCCCC1 NJNQUTDUIPVROZ-UHFFFAOYSA-N 0.000 abstract 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- XMIAFAKRAAMSGX-UHFFFAOYSA-N quinolin-5-amine Chemical compound C1=CC=C2C(N)=CC=CC2=N1 XMIAFAKRAAMSGX-UHFFFAOYSA-N 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- UFLMJULGUPSTCY-UHFFFAOYSA-M sodium;4-nitrobenzoate Chemical compound [Na+].[O-]C(=O)C1=CC=C([N+]([O-])=O)C=C1 UFLMJULGUPSTCY-UHFFFAOYSA-M 0.000 abstract 1
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
-
- 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
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
-
- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Organic nitro compounds are catalytically hydrogenated in an aqueous system with the aid of a concentrated noble metal catalyst deposited on an inert support, which has been diluted with an oleophilic carbon having an oil absorption factor of at least 200. The noble metal may be deposited on the support at a concentration of at least 2 per cent by weight and then diluted with the oleophilic carbon to a concentration of 0.01-1 per cent. Suitable carbons are those prepared from e.g. acetylene, i.e. "Furnace Blacks," which are non-porous. Suitable inert catalyst supports are carbon, diatomaceous earth or silica. The catalysts may be activated with e.g. oxides or hydroxides of iron, nickel, cobalt, aluminium, magnesium, manganese, chromium, vanadium or tungsten, or fluorides of boron and silicon as well as mixtures of these. Specific preparations mentioned are cyclohexylamine from nitrocyclohexane, b -amino-naphthalene from b -nitro-naphthalene, 5-aminoquinoline from 5-nitroquinoline, 1,5-diaminonaphthalene from 1,5-dinitronaphthalene, p-anisidine from p-nitro anisole, the amine of dinitrostilbene disulphonic acid from the corresponding sodium salt, p-aminobenzoic acid from p-nitro benzoic acid sodium salt and p-aminophenol from p-nitrophenol.ALSO:Catalysts for the hydrogenation of organic nitro compounds comprise a concentrated noble metal catalyst, e.g. platinum or palladium deposited on an inert support, which has been diluted with an oleophilic carbon having an oil absorption factor of at least 200. The noble metal may be deposited on the support at a concentration of at least 2 per cent by weight and then diluted with the oleophilic carbon to a concentration of 0.01 to 1 per cent. Suitable carbons are those prepared from acetylene, i.e. "Furnace Blacks," which are non-porous. Suitable inert catalyst supports are carbon, diatomaceous earth or silica. The catalysts may be activated with oxides or hydroxides of iron, nickel, cobalt, aluminium, magnesium, manganese, chromium, vanadium or tungsten or fluorides of boron and silicon, as well as mixtures of these.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB13152/56A GB786407A (en) | 1956-04-30 | 1956-04-30 | Process for the catalytic hydrogenation of organic nitro compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB13152/56A GB786407A (en) | 1956-04-30 | 1956-04-30 | Process for the catalytic hydrogenation of organic nitro compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB786407A true GB786407A (en) | 1957-11-20 |
Family
ID=22145345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13152/56A Expired GB786407A (en) | 1956-04-30 | 1956-04-30 | Process for the catalytic hydrogenation of organic nitro compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB786407A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3132180A (en) * | 1961-03-29 | 1964-05-05 | Gen Aniline & Film Corp | Catalytic reduction of aromatic mononitro compounds |
| US3213141A (en) * | 1959-07-06 | 1965-10-19 | Gen Aniline & Film Corp | Catalytic reduction of aromatic dinitro compounds |
| RU2202537C2 (en) * | 1995-08-04 | 2003-04-20 | Байер Аг | Water-containing tolylenediamine useful for storage or transporting as liquid, method for its preparing and method for preparing tolylene di- isocyanate |
| RU2307120C2 (en) * | 2005-11-28 | 2007-09-27 | Александр Иванович Козлов | Production of 1,5-diaminonaphthalene |
| CN103739505A (en) * | 2014-01-14 | 2014-04-23 | 新泰昊原化工有限责任公司 | Process for preparing ortho-aminophenol by virtue of continuous catalytic hydrogenation |
| CN105126869A (en) * | 2015-08-26 | 2015-12-09 | 辽宁石油化工大学 | Method for preparing p-aminophenol by using Ni/Ag/Fe3O4 composite catalyst |
| CN105562005A (en) * | 2016-02-29 | 2016-05-11 | 复旦大学 | Nano composite material with carbon-coated Ni nano crystal particles loaded on graphene and preparation method of nano composite material |
| CN110711600A (en) * | 2019-10-15 | 2020-01-21 | 兰州大学 | Preparation of metal-supported catalyst with nitrogen-doped carbon base derived from soybean dregs as carrier and method for catalyzing the hydrodeoxygenation of p-nitrophenol |
-
1956
- 1956-04-30 GB GB13152/56A patent/GB786407A/en not_active Expired
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3213141A (en) * | 1959-07-06 | 1965-10-19 | Gen Aniline & Film Corp | Catalytic reduction of aromatic dinitro compounds |
| US3132180A (en) * | 1961-03-29 | 1964-05-05 | Gen Aniline & Film Corp | Catalytic reduction of aromatic mononitro compounds |
| RU2202537C2 (en) * | 1995-08-04 | 2003-04-20 | Байер Аг | Water-containing tolylenediamine useful for storage or transporting as liquid, method for its preparing and method for preparing tolylene di- isocyanate |
| RU2307120C2 (en) * | 2005-11-28 | 2007-09-27 | Александр Иванович Козлов | Production of 1,5-diaminonaphthalene |
| CN103739505A (en) * | 2014-01-14 | 2014-04-23 | 新泰昊原化工有限责任公司 | Process for preparing ortho-aminophenol by virtue of continuous catalytic hydrogenation |
| CN103739505B (en) * | 2014-01-14 | 2016-02-24 | 新泰昊原化工有限责任公司 | A kind of continuous catalytic hydrogenation prepares the technique of Ortho-Aminophenol |
| CN105126869A (en) * | 2015-08-26 | 2015-12-09 | 辽宁石油化工大学 | Method for preparing p-aminophenol by using Ni/Ag/Fe3O4 composite catalyst |
| CN105562005A (en) * | 2016-02-29 | 2016-05-11 | 复旦大学 | Nano composite material with carbon-coated Ni nano crystal particles loaded on graphene and preparation method of nano composite material |
| CN105562005B (en) * | 2016-02-29 | 2019-05-31 | 复旦大学 | Carbon package Ni nano-crystalline granule is supported on nanocomposite on graphene and preparation method thereof |
| CN110711600A (en) * | 2019-10-15 | 2020-01-21 | 兰州大学 | Preparation of metal-supported catalyst with nitrogen-doped carbon base derived from soybean dregs as carrier and method for catalyzing the hydrodeoxygenation of p-nitrophenol |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3666813A (en) | Process for preparing aromatic haloamines from aromatic nitroamines | |
| GB1018373A (en) | Hydrogenation catalysts | |
| GB786407A (en) | Process for the catalytic hydrogenation of organic nitro compounds | |
| CA1127185A (en) | Toluene diamine from non-washed dinitrotoluene | |
| GB959507A (en) | Catalytic hydrogenation of nitrophenol | |
| Nishimura | Hydrogenation and Hydrogenolysis. III. Rhodium-Platinum Oxide as a Catalyst for the Hydrogenation of the Aromatic Nucleus | |
| US3194839A (en) | Catalytic hydrogenation of nitroaromatic compounds to aromatic amines | |
| Huang et al. | Selective reduction of nitroarenes with molybdenum disulfide | |
| Harrod et al. | Catalytic activation of molecular hydrogen in solution by chlororhodate (III) complexes | |
| GB1338268A (en) | Selective hydrogenation of alkynes | |
| Samuelsen et al. | The Hydrogenation of Nitro Compounds with Raney Nickel Treated with Chloroplatinic Acid and with Alkali1 | |
| GB990617A (en) | Process for the selective hydrogenation of hydrocarbon mixtures | |
| ES311270A1 (en) | The continuous procedure for the catalytic hydrogenation of an aromatic polynitro compound. (Machine-translation by Google Translate, not legally binding) | |
| JP2001354598A (en) | Adamantane manufacturing method | |
| ES310402A1 (en) | A continuous procedure for the catalytic hydrogenation of an aromatic polynitro compound. (Machine-translation by Google Translate, not legally binding) | |
| US3350452A (en) | Process for preparing aromatic primary haloamines | |
| US3427355A (en) | Process for preparing aniline and alkyl aniline | |
| Nishimura | Hydrogenation and Hydrogenolysis. II. Selective Hydrogenation of Benzyl Alcohol, Methylphenylcarbinol and Benzohydrol to the Corresponding Saturated Carbinols | |
| GB802100A (en) | Selective hydrogenation of acetylene in ethylene | |
| GB1126169A (en) | Process for the conversion of hydrocarbons | |
| US5646085A (en) | Material based on tungsten carbide(s), catalyst and process useful for the hydrogenation of an aromatic nitro or nitroso derivative employing this catalyst | |
| GB856366A (en) | Process for the production of p-aminophenol from nitrobenzene | |
| GB832153A (en) | Catalytic hydrogenation of the dinitro derivatives of toluene | |
| GB1289221A (en) | ||
| CN100457710C (en) | Metal salt catalyzed benzene nitrating to prepare nitrobenzene |