DE19651688A1 - Verfahren zur Herstellung von aromatischen Aminen durch Gasphasenhydrierung - Google Patents
Verfahren zur Herstellung von aromatischen Aminen durch GasphasenhydrierungInfo
- Publication number
- DE19651688A1 DE19651688A1 DE19651688A DE19651688A DE19651688A1 DE 19651688 A1 DE19651688 A1 DE 19651688A1 DE 19651688 A DE19651688 A DE 19651688A DE 19651688 A DE19651688 A DE 19651688A DE 19651688 A1 DE19651688 A1 DE 19651688A1
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- approx
- hours
- preparation
- aromatic amines
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 38
- 150000004982 aromatic amines Chemical class 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims description 10
- 238000005984 hydrogenation reaction Methods 0.000 title description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 128
- 239000001257 hydrogen Substances 0.000 claims abstract description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000000919 ceramic Substances 0.000 claims abstract description 18
- 229910052751 metal Inorganic materials 0.000 claims abstract description 12
- 239000002184 metal Substances 0.000 claims abstract description 12
- 150000002739 metals Chemical class 0.000 claims abstract description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
- -1 aromatic nitro compounds Chemical class 0.000 claims abstract description 8
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 6
- 230000000737 periodic effect Effects 0.000 claims abstract description 4
- 230000003197 catalytic effect Effects 0.000 claims abstract description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 32
- 239000007789 gas Substances 0.000 claims description 17
- 229910052763 palladium Inorganic materials 0.000 claims description 17
- 238000012546 transfer Methods 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 229910002804 graphite Inorganic materials 0.000 claims description 11
- 239000010439 graphite Substances 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
- 238000011068 loading method Methods 0.000 claims description 5
- 238000012856 packing Methods 0.000 claims description 3
- 239000000571 coke Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims 1
- 239000000758 substrate Substances 0.000 abstract description 2
- 239000007792 gaseous phase Substances 0.000 abstract 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 34
- 239000003921 oil Substances 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 230000008929 regeneration Effects 0.000 description 11
- 238000011069 regeneration method Methods 0.000 description 11
- 239000012876 carrier material Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 229910052720 vanadium Inorganic materials 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 240000007313 Tilia cordata Species 0.000 description 4
- 229910052797 bismuth Inorganic materials 0.000 description 4
- 239000012159 carrier gas Substances 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 150000002828 nitro derivatives Chemical class 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000158147 Sator Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 229910052745 lead Inorganic materials 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 229910052758 niobium Inorganic materials 0.000 description 3
- 239000010955 niobium Substances 0.000 description 3
- 230000000630 rising effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 241000589614 Pseudomonas stutzeri Species 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 229910052732 germanium Inorganic materials 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 241001235534 Graphis <ascomycete fungus> Species 0.000 description 1
- 241001026509 Kata Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical class [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 1
- OGUCKKLSDGRKSH-UHFFFAOYSA-N oxalic acid oxovanadium Chemical compound [V].[O].C(C(=O)O)(=O)O OGUCKKLSDGRKSH-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- ABKQFSYGIHQQLS-UHFFFAOYSA-J sodium tetrachloropalladate Chemical compound [Na+].[Na+].Cl[Pd+2](Cl)(Cl)Cl ABKQFSYGIHQQLS-UHFFFAOYSA-J 0.000 description 1
- RCVIHORGZULVTN-YGJXXQMASA-M sodium;(1r,4as,10ar)-1,4a-dimethyl-7-propan-2-yl-6-sulfo-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate Chemical compound [Na+].OC(=O)[C@@](C)([C@@H]1CC2)CCC[C@]1(C)C1=C2C=C(C(C)C)C(S([O-])(=O)=O)=C1 RCVIHORGZULVTN-YGJXXQMASA-M 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 229910052566 spinel group Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 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
-
- 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
- B01J23/54—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
- B01J23/648—Vanadium, niobium or tantalum or polonium
- B01J23/6482—Vanadium
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)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19651688A DE19651688A1 (de) | 1996-12-12 | 1996-12-12 | Verfahren zur Herstellung von aromatischen Aminen durch Gasphasenhydrierung |
| PL97333927A PL188179B1 (pl) | 1996-12-12 | 1997-12-01 | Sposób wytwarzania aromatycznych amin przez uwodornianie w fazie gazowej |
| DE59708143T DE59708143D1 (de) | 1996-12-12 | 1997-12-01 | Verfahren zur herstellung von aromatischen aminen durch gasphasenhydrierung |
| ES97952849T ES2182144T3 (es) | 1996-12-12 | 1997-12-01 | Procedimiento para producir aminas aromaticas mediante hidrogenacion en fase gaseosa. |
| KR10-1999-7005217A KR100530553B1 (ko) | 1996-12-12 | 1997-12-01 | 가스상 수소화 반응에 의한 방향족 아민의 제조 방법 |
| PCT/EP1997/006730 WO1998025881A2 (de) | 1996-12-12 | 1997-12-01 | Verfahren zur herstellung von aromatischen aminen durch gasphasenhydrierung |
| CN97180499A CN1128784C (zh) | 1996-12-12 | 1997-12-01 | 气相氢化法生产芳香胺类的方法 |
| HK00103876.3A HK1024467B (en) | 1996-12-12 | 1997-12-01 | Process for producing aromatic amines by gaseous phase hydrogenation |
| PT97952849T PT944578E (pt) | 1996-12-12 | 1997-12-01 | Processo para a preparacao de aminas aromaticas por hidrogenacao em fase gasosa |
| US09/319,486 US6043394A (en) | 1996-12-12 | 1997-12-01 | Process for producing aromatic amines by gaseous phase hydrogenation |
| CZ992111A CZ211199A3 (cs) | 1996-12-12 | 1997-12-01 | Způsob výroby aromatických aminů hydrogenací v plynné fázi |
| HU0000541A HU224698B1 (en) | 1996-12-12 | 1997-12-01 | Process for producing aromatic amines by gaseous phase hydrogenation |
| JP52617098A JP4108132B2 (ja) | 1996-12-12 | 1997-12-01 | 気相水素化による芳香族アミンの製造方法 |
| EP97952849A EP0944578B1 (de) | 1996-12-12 | 1997-12-01 | Verfahren zur herstellung von aromatischen aminen durch gasphasenhydrierung |
| RU99115098/04A RU2200150C2 (ru) | 1996-12-12 | 1997-12-01 | Способ получения ароматических аминов путем газофазного гидрирования |
| AU56582/98A AU5658298A (en) | 1996-12-12 | 1997-12-01 | Process for producing aromatic amines by gaseous phase hydrogenation |
| BR9713703-0A BR9713703A (pt) | 1996-12-12 | 1997-12-01 | Processo para preparação de aminas aromáticas por hidrogenação em fase gasosa |
| TW086118215A TW436473B (en) | 1996-12-12 | 1997-12-04 | Process for the production of aromatic amines by gas phase hydrogenation |
| BG103473A BG64123B1 (bg) | 1996-12-12 | 1999-06-08 | Метод за получаване на ароматни амини чрез хидрогениране в газова среда |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19651688A DE19651688A1 (de) | 1996-12-12 | 1996-12-12 | Verfahren zur Herstellung von aromatischen Aminen durch Gasphasenhydrierung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19651688A1 true DE19651688A1 (de) | 1998-06-18 |
Family
ID=7814480
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651688A Withdrawn DE19651688A1 (de) | 1996-12-12 | 1996-12-12 | Verfahren zur Herstellung von aromatischen Aminen durch Gasphasenhydrierung |
| DE59708143T Expired - Lifetime DE59708143D1 (de) | 1996-12-12 | 1997-12-01 | Verfahren zur herstellung von aromatischen aminen durch gasphasenhydrierung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59708143T Expired - Lifetime DE59708143D1 (de) | 1996-12-12 | 1997-12-01 | Verfahren zur herstellung von aromatischen aminen durch gasphasenhydrierung |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6043394A (enExample) |
| EP (1) | EP0944578B1 (enExample) |
| JP (1) | JP4108132B2 (enExample) |
| KR (1) | KR100530553B1 (enExample) |
| CN (1) | CN1128784C (enExample) |
| AU (1) | AU5658298A (enExample) |
| BG (1) | BG64123B1 (enExample) |
| BR (1) | BR9713703A (enExample) |
| CZ (1) | CZ211199A3 (enExample) |
| DE (2) | DE19651688A1 (enExample) |
| ES (1) | ES2182144T3 (enExample) |
| HU (1) | HU224698B1 (enExample) |
| PL (1) | PL188179B1 (enExample) |
| PT (1) | PT944578E (enExample) |
| RU (1) | RU2200150C2 (enExample) |
| TW (1) | TW436473B (enExample) |
| WO (1) | WO1998025881A2 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10061016A1 (de) * | 2000-12-08 | 2002-07-04 | Degussa | Aluminiumoxid-Germaniumdioxid-Siliziumdioxid-Mischoxid |
| EP2246320A1 (de) | 2009-04-29 | 2010-11-03 | Bayer MaterialScience AG | Verfahren zur Herstellung von aromatischen Aminen |
| WO2012095356A1 (de) | 2011-01-11 | 2012-07-19 | Bayer Materialscience Ag | Verfahren zur herstellung aromatischer amine |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6005143A (en) * | 1998-08-07 | 1999-12-21 | Air Products And Chemicals, Inc. | Use of a monolith catalyst for the hydrogenation of dinitrotoluene to toluenediamine |
| US6521791B1 (en) | 2001-11-09 | 2003-02-18 | Air Products And Chemicals, Inc. | Process for regenerating a monolith hydrogenation catalytic reactor |
| JP4260531B2 (ja) * | 2002-04-26 | 2009-04-30 | 住友精化株式会社 | 硫化水素の製造方法 |
| DE602004010234T2 (de) * | 2003-07-04 | 2008-10-02 | Sinorgchem Co., Shandong | Verfahren zur herstellung von 4-aminodiphenylamin |
| ES2373720T3 (es) * | 2003-07-04 | 2012-02-08 | Jiangsu Sinorgchem Technology Co., Ltd | Método para la producción de 4-aminodifenilamina. |
| US8486223B2 (en) * | 2003-07-04 | 2013-07-16 | Jiangsu Sinorgchem Technology Co., Ltd. | Falling film evaporator |
| US8686188B2 (en) | 2003-07-04 | 2014-04-01 | Jiangsu Sinorgchem Technology Co., Ltd. | Process for preparing 4-aminodiphenylamine |
| DE10347439A1 (de) * | 2003-10-13 | 2005-05-04 | Bayer Materialscience Ag | Verfahren zur Herstellung von aromatischen Aminen durch heterogen katalysierte Hydrierung |
| CN102259029B (zh) | 2010-05-24 | 2014-12-10 | 江苏圣奥化学科技有限公司 | 固体碱催化剂 |
| CN103068483B (zh) | 2010-07-30 | 2015-04-01 | 拜耳知识产权有限责任公司 | 恢复催化剂活性的方法 |
| DE102011081897A1 (de) | 2011-08-31 | 2013-02-28 | Bayer Materialscience Aktiengesellschaft | Katalysator und Verfahren zur Herstellung von aromatischen Aminen in der Gasphase |
| EP2641892A1 (de) | 2012-03-23 | 2013-09-25 | Bayer MaterialScience AG | Verfahren zur Reinigung von Anilin aus Gasphasenhydrierungen |
| EP2653462A1 (de) | 2012-04-16 | 2013-10-23 | Bayer MaterialScience AG | Verfahren zum verbesserten Anfahren der Reaktion bei der Herstellung von aromatischen Aminen aus Nitroaromaten |
| EP2653461A1 (de) | 2012-04-16 | 2013-10-23 | Bayer MaterialScience AG | Verfahren zum verbesserten Abfahren der Reaktion bei der Herstellung von aromatischen Aminen aus Nitroaromaten |
| JP6165844B2 (ja) | 2012-05-04 | 2017-07-19 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトＣｏｖｅｓｔｒｏ Ｄｅｕｔｓｃｈｌａｎｄ Ａｇ | 芳香族アミンを含む物質混合物、特に粗製アニリンの物質混合物の処理方法 |
| HUE060286T2 (hu) | 2014-06-24 | 2023-02-28 | Covestro Intellectual Property Gmbh & Co Kg | Eljárás kémiai termékek elõállítására az eljárás megszakítása mellett |
| EP3500553B1 (de) | 2016-08-17 | 2021-05-12 | Covestro Intellectual Property GmbH & Co. KG | Verfahren zur herstellung eines isocyanats und mindestens eines weiteren chemischen produkts in einem produktionsverbund |
| KR20220053569A (ko) | 2019-08-30 | 2022-04-29 | 코베스트로 도이칠란트 아게 | 방향족 니트로 화합물의 수소화 방법 |
| WO2025244748A1 (en) | 2024-05-23 | 2025-11-27 | Covestro Llc | Method for recovering o-aminophenol |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2135155A1 (de) * | 1971-07-14 | 1973-02-22 | Bayer Ag | Katalysator zur reduktion von nitroverbindungen |
| DE2244401A1 (de) * | 1972-09-09 | 1974-05-16 | Bayer Ag | Katalysator und verwendung des katalysators zur reduktion von nitrobenzol |
| BE793860A (fr) * | 1972-03-23 | 1973-07-10 | Bayer Ag | Catalyseur utilisable notamment pour la reduction de nitrobenzene |
| DE2849002A1 (de) * | 1978-11-11 | 1980-05-22 | Bayer Ag | Verfahren zur katalytischen hydrierung von nitrobenzol |
| PL134577B1 (en) * | 1982-04-27 | 1985-08-31 | Instytut Chemii Przemyslowej | Catalyst for manufacture of aromatic monoamines |
| DE4039026A1 (de) * | 1990-12-07 | 1992-06-11 | Bayer Ag | Verfahren zur herstellung von anilin |
-
1996
- 1996-12-12 DE DE19651688A patent/DE19651688A1/de not_active Withdrawn
-
1997
- 1997-12-01 HU HU0000541A patent/HU224698B1/hu not_active IP Right Cessation
- 1997-12-01 BR BR9713703-0A patent/BR9713703A/pt not_active IP Right Cessation
- 1997-12-01 PT PT97952849T patent/PT944578E/pt unknown
- 1997-12-01 CZ CZ992111A patent/CZ211199A3/cs unknown
- 1997-12-01 EP EP97952849A patent/EP0944578B1/de not_active Expired - Lifetime
- 1997-12-01 AU AU56582/98A patent/AU5658298A/en not_active Abandoned
- 1997-12-01 CN CN97180499A patent/CN1128784C/zh not_active Expired - Fee Related
- 1997-12-01 ES ES97952849T patent/ES2182144T3/es not_active Expired - Lifetime
- 1997-12-01 RU RU99115098/04A patent/RU2200150C2/ru not_active IP Right Cessation
- 1997-12-01 KR KR10-1999-7005217A patent/KR100530553B1/ko not_active Expired - Fee Related
- 1997-12-01 JP JP52617098A patent/JP4108132B2/ja not_active Expired - Fee Related
- 1997-12-01 PL PL97333927A patent/PL188179B1/pl not_active IP Right Cessation
- 1997-12-01 US US09/319,486 patent/US6043394A/en not_active Expired - Fee Related
- 1997-12-01 DE DE59708143T patent/DE59708143D1/de not_active Expired - Lifetime
- 1997-12-01 WO PCT/EP1997/006730 patent/WO1998025881A2/de not_active Ceased
- 1997-12-04 TW TW086118215A patent/TW436473B/zh not_active IP Right Cessation
-
1999
- 1999-06-08 BG BG103473A patent/BG64123B1/bg unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10061016A1 (de) * | 2000-12-08 | 2002-07-04 | Degussa | Aluminiumoxid-Germaniumdioxid-Siliziumdioxid-Mischoxid |
| EP2246320A1 (de) | 2009-04-29 | 2010-11-03 | Bayer MaterialScience AG | Verfahren zur Herstellung von aromatischen Aminen |
| DE102009019436A1 (de) | 2009-04-29 | 2010-11-04 | Bayer Materialscience Ag | Verfahren zur Herstellung von aromatischen Aminen |
| WO2012095356A1 (de) | 2011-01-11 | 2012-07-19 | Bayer Materialscience Ag | Verfahren zur herstellung aromatischer amine |
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0000541A3 (en) | 2000-11-28 |
| WO1998025881A2 (de) | 1998-06-18 |
| EP0944578A2 (de) | 1999-09-29 |
| BG64123B1 (bg) | 2004-01-30 |
| PL188179B1 (pl) | 2004-12-31 |
| WO1998025881A3 (de) | 1998-07-30 |
| HU224698B1 (en) | 2006-01-30 |
| AU5658298A (en) | 1998-07-03 |
| CN1128784C (zh) | 2003-11-26 |
| US6043394A (en) | 2000-03-28 |
| TW436473B (en) | 2001-05-28 |
| KR100530553B1 (ko) | 2005-11-23 |
| CN1239945A (zh) | 1999-12-29 |
| KR20000069430A (ko) | 2000-11-25 |
| CZ211199A3 (cs) | 1999-11-17 |
| RU2200150C2 (ru) | 2003-03-10 |
| BR9713703A (pt) | 2000-05-09 |
| DE59708143D1 (de) | 2002-10-10 |
| BG103473A (en) | 2000-03-31 |
| HK1024467A1 (en) | 2000-10-13 |
| JP4108132B2 (ja) | 2008-06-25 |
| EP0944578B1 (de) | 2002-09-04 |
| PL333927A1 (en) | 2000-01-31 |
| HUP0000541A2 (en) | 2000-07-28 |
| JP2001505893A (ja) | 2001-05-08 |
| ES2182144T3 (es) | 2003-03-01 |
| PT944578E (pt) | 2002-12-31 |
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