BRPI0404434B1 - Processo para a preparação de aminas aromáticas mediante hidrogenação catalisada heterogeneamente - Google Patents
Processo para a preparação de aminas aromáticas mediante hidrogenação catalisada heterogeneamente Download PDFInfo
- Publication number
- BRPI0404434B1 BRPI0404434B1 BRPI0404434-7A BRPI0404434A BRPI0404434B1 BR PI0404434 B1 BRPI0404434 B1 BR PI0404434B1 BR PI0404434 A BRPI0404434 A BR PI0404434A BR PI0404434 B1 BRPI0404434 B1 BR PI0404434B1
- Authority
- BR
- Brazil
- Prior art keywords
- catalyst
- reactor
- catalytically active
- catalytic hydrogenation
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 43
- 238000002360 preparation method Methods 0.000 title claims description 17
- 150000004982 aromatic amines Chemical class 0.000 title claims description 12
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title claims description 11
- 239000003054 catalyst Substances 0.000 claims description 62
- 238000000576 coating method Methods 0.000 claims description 21
- 239000011248 coating agent Substances 0.000 claims description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 13
- 229910052763 palladium Inorganic materials 0.000 claims description 7
- -1 nitro aromatic compounds Chemical class 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 36
- 239000001257 hydrogen Substances 0.000 description 26
- 229910052739 hydrogen Inorganic materials 0.000 description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 238000005984 hydrogenation reaction Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000000969 carrier Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000007789 gas Substances 0.000 description 7
- 238000011068 loading method Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000010790 dilution Methods 0.000 description 6
- 239000012895 dilution Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000003618 dip coating Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 229910052878 cordierite Inorganic materials 0.000 description 2
- 229910052593 corundum Inorganic materials 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- JSKIRARMQDRGJZ-UHFFFAOYSA-N dimagnesium dioxido-bis[(1-oxido-3-oxo-2,4,6,8,9-pentaoxa-1,3-disila-5,7-dialuminabicyclo[3.3.1]nonan-7-yl)oxy]silane Chemical compound [Mg++].[Mg++].[O-][Si]([O-])(O[Al]1O[Al]2O[Si](=O)O[Si]([O-])(O1)O2)O[Al]1O[Al]2O[Si](=O)O[Si]([O-])(O1)O2 JSKIRARMQDRGJZ-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000009420 retrofitting Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 2
- 229910001845 yogo sapphire Inorganic materials 0.000 description 2
- 229910018404 Al2 O3 Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- VEFXTGTZJOWDOF-UHFFFAOYSA-N benzene;hydrate Chemical compound O.C1=CC=CC=C1 VEFXTGTZJOWDOF-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000001035 drying 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
- 239000006260 foam Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical class [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 239000010457 zeolite 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
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10347439A DE10347439A1 (de) | 2003-10-13 | 2003-10-13 | Verfahren zur Herstellung von aromatischen Aminen durch heterogen katalysierte Hydrierung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BRPI0404434A BRPI0404434A (pt) | 2005-06-21 |
| BRPI0404434B1 true BRPI0404434B1 (pt) | 2014-03-25 |
Family
ID=34353377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0404434-7A BRPI0404434B1 (pt) | 2003-10-13 | 2004-10-13 | Processo para a preparação de aminas aromáticas mediante hidrogenação catalisada heterogeneamente |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7193112B2 (enExample) |
| EP (1) | EP1524259B1 (enExample) |
| JP (1) | JP4745638B2 (enExample) |
| KR (1) | KR101117446B1 (enExample) |
| CN (1) | CN100415375C (enExample) |
| BR (1) | BRPI0404434B1 (enExample) |
| DE (1) | DE10347439A1 (enExample) |
| SG (1) | SG111261A1 (enExample) |
| TW (1) | TW200524841A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006011497A1 (de) * | 2006-03-14 | 2007-09-20 | Bayer Technology Services Gmbh | Verfahren und Vorrichtung zur Herstellung von aromatischen Aminen durch eine heterogen katalysierte Hydrierung |
| CN100455559C (zh) * | 2006-11-08 | 2009-01-28 | 大连理工大学 | 芳香族硝基化合物还原制备芳胺的方法 |
| KR101770439B1 (ko) | 2010-01-14 | 2017-08-22 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 액체상에서 방향족 아민을 제조하는 방법 |
| US8809587B2 (en) * | 2010-12-30 | 2014-08-19 | Kellogg Brown & Root Llc | Systems and methods for producing aromatic amines and removing phenol therefrom |
| JP2014510030A (ja) | 2011-01-11 | 2014-04-24 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 芳香族アミンの製造方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3136818A (en) | 1960-01-15 | 1964-06-09 | Basf Ag | Production of aniline |
| GB1452466A (en) | 1975-04-04 | 1976-10-13 | Chemopetrol | Process for the production of aniline and apparatus therefor |
| DE2849002A1 (de) | 1978-11-11 | 1980-05-22 | Bayer Ag | Verfahren zur katalytischen hydrierung von nitrobenzol |
| DE4428018A1 (de) | 1994-08-08 | 1996-02-15 | Bayer Ag | Verfahren zur Herstellung von aromatischen Aminen |
| DE4428017A1 (de) * | 1994-08-08 | 1996-02-15 | Bayer Ag | Verfahren zur Herstellung von aromatischen Aminen |
| DE19651688A1 (de) | 1996-12-12 | 1998-06-18 | Bayer Ag | Verfahren zur Herstellung von aromatischen Aminen durch Gasphasenhydrierung |
| 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 |
| DE19931902A1 (de) | 1999-07-08 | 2001-01-18 | Consortium Elektrochem Ind | Verfahren zur Herstellung von monolithischen Oxidationskatalysatoren und deren Verwendung bei der Gasphasenoxidation von Kohlenwasserstoffen |
| DE19963443A1 (de) * | 1999-12-28 | 2001-07-05 | Basf Ag | Dünnschichtkatalysatoren auf Basis von Raney-Legierungen und Verfahren zu deren Herstellung |
| US20030036477A1 (en) | 2001-04-20 | 2003-02-20 | Nordquist Andrew Francis | Coated monolith substrate and monolith catalysts |
| US6479704B1 (en) | 2001-04-20 | 2002-11-12 | Air Products And Chemicals, Inc. | Hydrogenation with monolith reactor under conditions of immiscible liquid phases |
| US7109378B2 (en) * | 2001-08-30 | 2006-09-19 | Air Products And Chemicals, Inc. | Monolith catalytic reactor coupled to static mixer |
| US7074962B2 (en) | 2002-02-15 | 2006-07-11 | Air Products And Chemicals, Inc. | Catalyst holder and agitation system for converting stirred tank reactor to fixed bed reactor |
-
2003
- 2003-10-13 DE DE10347439A patent/DE10347439A1/de not_active Withdrawn
-
2004
- 2004-09-30 EP EP04023292.8A patent/EP1524259B1/de not_active Expired - Lifetime
- 2004-10-07 US US10/960,455 patent/US7193112B2/en not_active Expired - Fee Related
- 2004-10-12 KR KR1020040081209A patent/KR101117446B1/ko not_active Expired - Fee Related
- 2004-10-12 TW TW093130796A patent/TW200524841A/zh unknown
- 2004-10-12 SG SG200406199A patent/SG111261A1/en unknown
- 2004-10-13 CN CNB2004100835835A patent/CN100415375C/zh not_active Expired - Fee Related
- 2004-10-13 JP JP2004298640A patent/JP4745638B2/ja not_active Expired - Fee Related
- 2004-10-13 BR BRPI0404434-7A patent/BRPI0404434B1/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1524259A1 (de) | 2005-04-20 |
| US20050080293A1 (en) | 2005-04-14 |
| CN1621153A (zh) | 2005-06-01 |
| EP1524259B1 (de) | 2016-06-08 |
| BRPI0404434A (pt) | 2005-06-21 |
| KR20050035502A (ko) | 2005-04-18 |
| JP4745638B2 (ja) | 2011-08-10 |
| KR101117446B1 (ko) | 2012-03-20 |
| JP2005120087A (ja) | 2005-05-12 |
| SG111261A1 (en) | 2005-05-30 |
| US7193112B2 (en) | 2007-03-20 |
| CN100415375C (zh) | 2008-09-03 |
| DE10347439A1 (de) | 2005-05-04 |
| TW200524841A (en) | 2005-08-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B03H | Publication of an application: rectification [chapter 3.8 patent gazette] | ||
| B07A | Application suspended after technical examination (opinion) [chapter 7.1 patent gazette] | ||
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |
Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 13/10/2004, OBSERVADAS AS CONDICOES LEGAIS. |
|
| B21F | Lapse acc. art. 78, item iv - on non-payment of the annual fees in time | ||
| B24J | Lapse because of non-payment of annual fees (definitively: art 78 iv lpi, resolution 113/2013 art. 12) |