TWI455758B - 氨氧化觸媒及使用其之腈化合物之製法 - Google Patents
氨氧化觸媒及使用其之腈化合物之製法 Download PDFInfo
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- TWI455758B TWI455758B TW099118996A TW99118996A TWI455758B TW I455758 B TWI455758 B TW I455758B TW 099118996 A TW099118996 A TW 099118996A TW 99118996 A TW99118996 A TW 99118996A TW I455758 B TWI455758 B TW I455758B
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- oxide
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- oxidation catalyst
- ammonia oxidation
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 title claims 24
- 239000003054 catalyst Substances 0.000 title claims 14
- 229910021529 ammonia Inorganic materials 0.000 title claims 12
- -1 nitrile compound Chemical class 0.000 title claims 10
- 230000001590 oxidative effect Effects 0.000 title 1
- 230000003647 oxidation Effects 0.000 claims 10
- 238000007254 oxidation reaction Methods 0.000 claims 10
- 238000004519 manufacturing process Methods 0.000 claims 6
- 229910000420 cerium oxide Inorganic materials 0.000 claims 5
- 150000002894 organic compounds Chemical class 0.000 claims 5
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims 5
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 229910003460 diamond Inorganic materials 0.000 claims 4
- 239000010432 diamond Substances 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims 2
- 229910052810 boron oxide Inorganic materials 0.000 claims 2
- 229910000423 chromium oxide Inorganic materials 0.000 claims 2
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 claims 2
- 239000007789 gas Substances 0.000 claims 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims 2
- 229910000476 molybdenum oxide Inorganic materials 0.000 claims 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 2
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 claims 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims 2
- 229910001392 phosphorus oxide Inorganic materials 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 claims 2
- 229910001928 zirconium oxide Inorganic materials 0.000 claims 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 150000001717 carbocyclic compounds Chemical class 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000000919 ceramic Substances 0.000 claims 1
- 229910000428 cobalt oxide Inorganic materials 0.000 claims 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 229910052878 cordierite Inorganic materials 0.000 claims 1
- 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 claims 1
- KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-UHFFFAOYSA-N 0.000 claims 1
- 238000010574 gas phase reaction Methods 0.000 claims 1
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- NFFIWVVINABMKP-UHFFFAOYSA-N methylidynetantalum Chemical compound [Ta]#C NFFIWVVINABMKP-UHFFFAOYSA-N 0.000 claims 1
- 229910052863 mullite Inorganic materials 0.000 claims 1
- 229930014626 natural product Natural products 0.000 claims 1
- 229910000480 nickel oxide Inorganic materials 0.000 claims 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 claims 1
- 229940078552 o-xylene Drugs 0.000 claims 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052573 porcelain Inorganic materials 0.000 claims 1
- 229910003468 tantalcarbide Inorganic materials 0.000 claims 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims 1
- 229910001930 tungsten oxide Inorganic materials 0.000 claims 1
- 229910001935 vanadium oxide Inorganic materials 0.000 claims 1
Classifications
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- 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
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
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- 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
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/063—Titanium; Oxides or hydroxides thereof
-
- 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
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/20—Vanadium, niobium or tantalum
- B01J23/22—Vanadium
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- 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
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/26—Chromium
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- 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
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/28—Molybdenum
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- 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
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/32—Manganese, technetium or rhenium
- B01J23/34—Manganese
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- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
- B01J27/198—Vanadium
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- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/40—Catalysts, in general, characterised by their form or physical properties characterised by dimensions, e.g. grain size
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- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
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- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0215—Coating
- B01J37/0221—Coating of particles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/24—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons
- C07C253/28—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons containing six-membered aromatic rings, e.g. styrene
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- 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
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Claims (15)
- 一種氨氧化觸媒，其係含有氧化釩、氧化鈦及鑽石。
- 如申請專利範圍第1項之氨氧化觸媒，其中鑽石的粒徑係大於0μm、10μm以下。
- 如申請專利範圍第1項之氨氧化觸媒，其中鑽石係為天然品。
- 如申請專利範圍第1項之氨氧化觸媒，其係更進一步含有從由氧化鉻、氧化鉬、氧化鎢、氧化鋯、氧化鐵、氧化鈷、氧化鎳、氧化鈮、氧化硼、氧化鋁、氧化鍺、氧化磷、氧化銻及氧化鉍所構成之群組中選出一種以上的氧化物。
- 如申請專利範圍第1項之氨氧化觸媒，其係更進一步含有從由氧化鉻、氧化鉬、氧化鐵、氧化硼及氧化磷所構成之群組中選出一種以上的氧化物。
- 如申請專利範圍第1項之氨氧化觸媒，其中鑽石的含量，相對於氨氧化觸媒的重量，係佔0.1～70重量%。
- 如申請專利範圍第1項之氨氧化觸媒，其係被對反應不具活性的載體所載持。
- 如申請專利範圍第7項之氨氧化觸媒，其中載體係為含有由碳化矽、氧化鋁、二氧化矽、氧化鋯、滑石(steatite)、堇青石、莫來石、陶器及瓷器所構成之群組中選出至一種類之成型載體。
- 如申請專利範圍第7項之氨氧化觸媒，其中氨氧化觸媒的載持量，相對於氨氧化觸媒和載體的合計重量，係為0.1～20重量%的範圍。
- 一種腈化合物的製造方法，其係包含：在如申請專利範圍第1至9項中任一項之氨氧化觸媒存在的狀況下，有機化合物和含有氨氣及氧氣的混合氣體在氣相下反應的氨氧化反應步驟。
- 如申請專利範圍第10項之腈化合物的製造方法，其中有機化合物係為碳環化合物或雜環化合物。
- 如申請專利範圍第10項之腈化合物的製造方法，其中有機化合物的分子內係具有一個以上從由甲基、乙基、丙基、甲醯基、乙醯基、羥甲基及甲氧基羰基所構成之群組中選出的有機取代基。
- 如申請專利範圍第10項之腈化合物的製造方法，其中有機化合物的分子內係具有一個以上從由甲基、乙基、丙基、乙醯基及甲醯基所構成之群組中選出的有機取代基。
- 如申請專利範圍第10項之腈化合物的製造方法，其中有機化合物係為從鄰二甲苯、間二甲苯及對二甲苯之中選出一種以上者。
- 如申請專利範圍第10項之腈化合物的製造方法，其中氨氧化反應步驟之氣相反應係以固定床流通方式進行。
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009140196 | 2009-06-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201114485A TW201114485A (en) | 2011-05-01 |
| TWI455758B true TWI455758B (zh) | 2014-10-11 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW099118996A TWI455758B (zh) | 2009-06-11 | 2010-06-11 | 氨氧化觸媒及使用其之腈化合物之製法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20120149933A1 (zh) |
| EP (1) | EP2441514B1 (zh) |
| JP (1) | JP5626208B2 (zh) |
| KR (1) | KR101690351B1 (zh) |
| CN (1) | CN102458654B (zh) |
| TW (1) | TWI455758B (zh) |
| WO (1) | WO2010143690A1 (zh) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5509688B2 (ja) * | 2008-06-19 | 2014-06-04 | 三菱瓦斯化学株式会社 | 触媒及びこれを用いたカルボン酸又はカルボン酸無水物の製造方法 |
| EP2543435B1 (en) | 2010-03-04 | 2018-10-17 | Mitsubishi Gas Chemical Company, Inc. | Amide compound production catalyst, and process for production of amide compound |
| US9856149B2 (en) * | 2012-09-29 | 2018-01-02 | Nanjing Tech University | Vanadium-titanium compound material with high thermal stability and high activity and preparation method thereof |
| CN106111172B (zh) * | 2016-06-22 | 2018-06-15 | 徐州恒鼎生物科技有限公司 | 一种用于催化氨氧化反应制备3-氰基吡啶的催化剂及其制备方法 |
| CN116351434B (zh) * | 2023-02-17 | 2024-05-03 | 中南民族大学 | 用于制备2,4-二氯苯腈的催化剂及制备方法和用途 |
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| US6710011B2 (en) * | 2001-12-21 | 2004-03-23 | Saudi Basic Industries Corporatioin | Catalyst compositions for the ammoxidation of alkanes and olefins, methods of making and of using same |
| CN1697684A (zh) | 2002-10-16 | 2005-11-16 | 戴蒙得创新股份有限公司 | 硼掺杂的蓝色金刚石及其制备方法 |
| ITFI20030115A1 (it) | 2003-04-24 | 2004-10-25 | Fabio Perini | Dispositivo e metodo per movimentare logs in macchine troncatrici |
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2010
- 2010-06-10 JP JP2011518574A patent/JP5626208B2/ja active Active
- 2010-06-10 KR KR1020117029398A patent/KR101690351B1/ko active IP Right Grant
- 2010-06-10 US US13/377,626 patent/US20120149933A1/en not_active Abandoned
- 2010-06-10 CN CN201080025695.9A patent/CN102458654B/zh active Active
- 2010-06-10 WO PCT/JP2010/059850 patent/WO2010143690A1/ja active Application Filing
- 2010-06-10 EP EP10786221.1A patent/EP2441514B1/en active Active
- 2010-06-11 TW TW099118996A patent/TWI455758B/zh active
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH07285923A (ja) * | 1994-04-15 | 1995-10-31 | Nippon Shokubai Co Ltd | シアノナフタレン類の製造方法 |
| JPH1133399A (ja) * | 1997-07-10 | 1999-02-09 | Standard Oil Co:The | 改良されたバナジウムアンチモン酸化物ベースの酸化触媒およびアンモ酸化触媒の調製方法 |
| JPH11310562A (ja) * | 1998-03-26 | 1999-11-09 | Standard Oil Co:The | パラフィンの選択的アンモ酸化のためのモリブデン促進型バナジウムアンチモン酸化物をベ―スとした触媒 |
| JP2001062303A (ja) * | 1999-06-24 | 2001-03-13 | Nippon Shokubai Co Ltd | 芳香族化合物の気相酸化用触媒 |
| EP2135671A2 (en) * | 2008-06-19 | 2009-12-23 | Mitsubishi Gas Chemical Company, Inc. | Catalyst and method for producing carboxylic acid and/or carboxylic anhydride in the presence of the catalyst |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20120038933A (ko) | 2012-04-24 |
| EP2441514A4 (en) | 2013-01-09 |
| EP2441514A1 (en) | 2012-04-18 |
| JP5626208B2 (ja) | 2014-11-19 |
| EP2441514B1 (en) | 2014-04-09 |
| CN102458654B (zh) | 2014-12-31 |
| KR101690351B1 (ko) | 2016-12-27 |
| TW201114485A (en) | 2011-05-01 |
| CN102458654A (zh) | 2012-05-16 |
| US20120149933A1 (en) | 2012-06-14 |
| WO2010143690A1 (ja) | 2010-12-16 |
| JPWO2010143690A1 (ja) | 2012-11-29 |
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