FR2525591A1 - Catalyseur pour la preparation de mono-amines aromatiques - Google Patents
Catalyseur pour la preparation de mono-amines aromatiques Download PDFInfo
- Publication number
- FR2525591A1 FR2525591A1 FR8306956A FR8306956A FR2525591A1 FR 2525591 A1 FR2525591 A1 FR 2525591A1 FR 8306956 A FR8306956 A FR 8306956A FR 8306956 A FR8306956 A FR 8306956A FR 2525591 A1 FR2525591 A1 FR 2525591A1
- Authority
- FR
- France
- Prior art keywords
- catalyst
- silica
- magnesium
- support
- mass
- 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.)
- Granted
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 44
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 7
- 239000000377 silicon dioxide Substances 0.000 title claims abstract description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 title claims abstract description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims description 10
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 title claims description 8
- 239000000395 magnesium oxide Substances 0.000 title claims description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 title claims description 4
- 239000011787 zinc oxide Substances 0.000 title claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 title claims description 3
- 239000005751 Copper oxide Substances 0.000 title description 2
- 150000001412 amines Chemical class 0.000 title description 2
- 229910000431 copper oxide Inorganic materials 0.000 title description 2
- 229910052802 copper Inorganic materials 0.000 claims abstract description 10
- 230000003197 catalytic effect Effects 0.000 claims abstract description 9
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 9
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 3
- 239000010949 copper Substances 0.000 claims description 11
- 239000011777 magnesium Substances 0.000 claims description 4
- 150000002828 nitro derivatives Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract description 21
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 10
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 abstract description 5
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 239000007792 gaseous phase Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 229960004643 cupric oxide Drugs 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000000975 co-precipitation Methods 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GXDVEXJTVGRLNW-UHFFFAOYSA-N [Cr].[Cu] Chemical compound [Cr].[Cu] GXDVEXJTVGRLNW-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- -1 aromatic nitro compounds Chemical class 0.000 description 1
- 229910001593 boehmite Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical class [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 235000012254 magnesium hydroxide Nutrition 0.000 description 1
- 235000012243 magnesium silicates Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- WWNBZGLDODTKEM-UHFFFAOYSA-N sulfanylidenenickel Chemical compound [Ni]=S WWNBZGLDODTKEM-UHFFFAOYSA-N 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical class [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/80—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with zinc, cadmium or mercury
-
- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL1982236160A PL134577B1 (en) | 1982-04-27 | 1982-04-27 | Catalyst for manufacture of aromatic monoamines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2525591A1 true FR2525591A1 (fr) | 1983-10-28 |
| FR2525591B1 FR2525591B1 (enrdf_load_stackoverflow) | 1985-04-26 |
Family
ID=20012368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8306956A Granted FR2525591A1 (fr) | 1982-04-27 | 1983-04-27 | Catalyseur pour la preparation de mono-amines aromatiques |
Country Status (5)
| Country | Link |
|---|---|
| BG (1) | BG38636A3 (enrdf_load_stackoverflow) |
| FR (1) | FR2525591A1 (enrdf_load_stackoverflow) |
| IT (1) | IT1161240B (enrdf_load_stackoverflow) |
| PL (1) | PL134577B1 (enrdf_load_stackoverflow) |
| SU (1) | SU1356952A3 (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994014791A1 (en) * | 1992-12-23 | 1994-07-07 | Shell Internationale Research Maatschappij B.V. | Process for preparing 2-para-dioxanones |
| US6043394A (en) * | 1996-12-12 | 2000-03-28 | Bayer Aktiengesellschaft | Process for producing aromatic amines by gaseous phase hydrogenation |
| WO2015137301A1 (ja) * | 2014-03-11 | 2015-09-17 | 東ソー株式会社 | 芳香族ニトロ化合物用水素化触媒とその製造方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB191413149A (en) * | 1914-05-28 | 1915-05-28 | James Yate Johnson | Improvements in the Manufacture of Aromatic Amines, and Materials to be used in such Manufacture. |
| DE869052C (de) * | 1951-02-01 | 1953-03-02 | Basf Ag | Verfahren zur Herstellung von Katalysatoren fuer die Hydrierung organischer Verbindungen, insbesondere von Fettsaeuren, ihren Anhydriden und Estern zu Fettalkoholen |
| GB1281112A (en) * | 1970-03-06 | 1972-07-12 | Margarita Ivanovna Markina | A method of preparing catalysts |
| FR2210595A1 (en) * | 1972-12-18 | 1974-07-12 | Csr Ltd | Catalytic hydrogenation of sugar - eg invert sugar, to obtain increased yields of mannitol, using supported raney-nickel or nickel contg additives as catalyst |
| US4178310A (en) * | 1975-03-17 | 1979-12-11 | American Cyanamid Company | Catalyst for hydration of nitriles |
-
1982
- 1982-04-27 PL PL1982236160A patent/PL134577B1/pl unknown
-
1983
- 1983-04-25 SU SU833616351A patent/SU1356952A3/ru active
- 1983-04-26 BG BG060721A patent/BG38636A3/xx unknown
- 1983-04-27 FR FR8306956A patent/FR2525591A1/fr active Granted
- 1983-04-27 IT IT20798/83A patent/IT1161240B/it active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB191413149A (en) * | 1914-05-28 | 1915-05-28 | James Yate Johnson | Improvements in the Manufacture of Aromatic Amines, and Materials to be used in such Manufacture. |
| DE869052C (de) * | 1951-02-01 | 1953-03-02 | Basf Ag | Verfahren zur Herstellung von Katalysatoren fuer die Hydrierung organischer Verbindungen, insbesondere von Fettsaeuren, ihren Anhydriden und Estern zu Fettalkoholen |
| GB1281112A (en) * | 1970-03-06 | 1972-07-12 | Margarita Ivanovna Markina | A method of preparing catalysts |
| FR2210595A1 (en) * | 1972-12-18 | 1974-07-12 | Csr Ltd | Catalytic hydrogenation of sugar - eg invert sugar, to obtain increased yields of mannitol, using supported raney-nickel or nickel contg additives as catalyst |
| US4178310A (en) * | 1975-03-17 | 1979-12-11 | American Cyanamid Company | Catalyst for hydration of nitriles |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994014791A1 (en) * | 1992-12-23 | 1994-07-07 | Shell Internationale Research Maatschappij B.V. | Process for preparing 2-para-dioxanones |
| US6043394A (en) * | 1996-12-12 | 2000-03-28 | Bayer Aktiengesellschaft | Process for producing aromatic amines by gaseous phase hydrogenation |
| WO2015137301A1 (ja) * | 2014-03-11 | 2015-09-17 | 東ソー株式会社 | 芳香族ニトロ化合物用水素化触媒とその製造方法 |
| JP2015186796A (ja) * | 2014-03-11 | 2015-10-29 | 東ソー株式会社 | 芳香族ニトロ化合物用水素化触媒とその製造方法 |
| EP3117901A4 (en) * | 2014-03-11 | 2017-11-01 | Tosoh Corporation | Hydrogenation catalyst for aromatic nitro compound, and method for manufacturing same |
Also Published As
| Publication number | Publication date |
|---|---|
| PL236160A1 (en) | 1983-11-07 |
| IT1161240B (it) | 1987-03-18 |
| IT8320798A0 (it) | 1983-04-27 |
| FR2525591B1 (enrdf_load_stackoverflow) | 1985-04-26 |
| SU1356952A3 (ru) | 1987-11-30 |
| BG38636A3 (en) | 1986-01-15 |
| PL134577B1 (en) | 1985-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |