JP4523214B2 - 促進イリジウム触媒を用いる気相カルボニル化方法 - Google Patents
促進イリジウム触媒を用いる気相カルボニル化方法 Download PDFInfo
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- JP4523214B2 JP4523214B2 JP2001518399A JP2001518399A JP4523214B2 JP 4523214 B2 JP4523214 B2 JP 4523214B2 JP 2001518399 A JP2001518399 A JP 2001518399A JP 2001518399 A JP2001518399 A JP 2001518399A JP 4523214 B2 JP4523214 B2 JP 4523214B2
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- 239000003054 catalyst Substances 0.000 title claims description 117
- 238000005810 carbonylation reaction Methods 0.000 title claims description 70
- 230000006315 carbonylation Effects 0.000 title claims description 63
- 238000000034 method Methods 0.000 title claims description 58
- 229910052741 iridium Inorganic materials 0.000 title claims description 50
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims description 44
- 239000012808 vapor phase Substances 0.000 title description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 132
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 81
- 229910052751 metal Inorganic materials 0.000 claims description 62
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 30
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- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 25
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 23
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- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 13
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- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 4
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- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 claims description 3
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- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 229910000457 iridium oxide Inorganic materials 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052680 mordenite Inorganic materials 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000013460 polyoxometalate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- WWNBZGLDODTKEM-UHFFFAOYSA-N sulfanylidenenickel Chemical compound [Ni]=S WWNBZGLDODTKEM-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910052715 tantalum 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical class Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
- C07C67/37—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by reaction of ethers with carbon monoxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/12—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on an oxygen-containing group in organic compounds, e.g. alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/383,124 US6355837B1 (en) | 1999-08-25 | 1999-08-25 | Vapor phase carbonylation process using group 4 metal promoted iridium catalyst |
| US09/383,124 | 1999-08-25 | ||
| PCT/US2000/022133 WO2001014306A1 (en) | 1999-08-25 | 2000-08-11 | Vapor phase carbonylation process using promoted iridium catalyst |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003507446A JP2003507446A (ja) | 2003-02-25 |
| JP2003507446A5 JP2003507446A5 (enExample) | 2007-09-06 |
| JP4523214B2 true JP4523214B2 (ja) | 2010-08-11 |
Family
ID=23511827
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001518399A Expired - Fee Related JP4523214B2 (ja) | 1999-08-25 | 2000-08-11 | 促進イリジウム触媒を用いる気相カルボニル化方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6355837B1 (enExample) |
| EP (1) | EP1206434B1 (enExample) |
| JP (1) | JP4523214B2 (enExample) |
| CN (1) | CN1192010C (enExample) |
| BR (1) | BR0013520A (enExample) |
| DE (1) | DE60011099T2 (enExample) |
| WO (1) | WO2001014306A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6617471B2 (en) * | 2001-06-20 | 2003-09-09 | Eastman Chemical Company | Method for carbonylation of lower aliphatic alcohols using tin promoted iridium catalyst |
| CA2496839A1 (en) | 2004-07-19 | 2006-01-19 | Woodland Chemical Systems Inc. | Process for producing ethanol from synthesis gas rich in carbon monoxide |
| US20060252959A1 (en) * | 2005-05-05 | 2006-11-09 | The Regents Of The University Of California | Process for carbonylation of alkyl ethers |
| US7465822B2 (en) | 2005-05-05 | 2008-12-16 | Bp Chemicals Ltd. | Process for carbonylation of alkyl ethers |
| KR20080108605A (ko) * | 2006-04-05 | 2008-12-15 | 우드랜드 바이오퓨엘스 인크. | 합성 가스에 의해 바이오매스를 에탄올로 전환시키는 시스템 및 방법 |
| US7507855B2 (en) * | 2006-12-15 | 2009-03-24 | The Regents Of The University Of California | Process for carbonylation of aliphatic alcohols and/or ester derivatives thereof |
| EP1985362A1 (en) * | 2007-04-26 | 2008-10-29 | BP Chemicals Limited | Process for the carbonylation of dimethyl ether |
| US9421522B2 (en) | 2011-12-28 | 2016-08-23 | Eastman Chemical Company | Iridium catalysts for carbonylation |
| CN108067222B (zh) * | 2016-11-15 | 2020-09-22 | 中国科学院大连化学物理研究所 | 活性炭载体负载的硫促进的铱基催化剂及其制备和应用 |
| CN116716633B (zh) * | 2023-08-08 | 2023-12-22 | 四川大学 | 一种碳基氧化铪负载铱团簇的电催化剂及其制备和用途 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3717670A (en) * | 1968-08-02 | 1973-02-20 | Monsanto Co | Production of carboxylic acids and esters |
| US3772380A (en) | 1970-03-12 | 1973-11-13 | Monsanto Co | Production of carboxylic acids and esters |
| US3689533A (en) | 1971-03-15 | 1972-09-05 | Monsanto Co | Production of carboxylic acids and esters |
| US4417077A (en) | 1980-10-01 | 1983-11-22 | University Of Illinois Foundation | Heterogeneous anionic transition metal catalysts |
| US4612387A (en) | 1982-01-04 | 1986-09-16 | Air Products And Chemicals, Inc. | Production of carboxylic acids and esters |
| DE3463257D1 (en) | 1983-03-25 | 1987-05-27 | Texaco Development Corp | A process for producing carboxylic acids by carbonylation of alkanols over a carbon catalyst |
| US4625050A (en) | 1983-06-23 | 1986-11-25 | Chevron Research Company | Ether homologation to esters and alcohols using a heterogeneous sulfided catalyst |
| DE3323654A1 (de) | 1983-07-01 | 1985-01-03 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von essigsaeure und methylacetat |
| JPS60214756A (ja) * | 1984-04-05 | 1985-10-28 | Daicel Chem Ind Ltd | 酢酸の製造方法 |
| US5144068A (en) | 1984-05-03 | 1992-09-01 | Hoechst Celanese Corporation | Methanol carbonylation process |
| DE3429179A1 (de) * | 1984-08-08 | 1986-02-20 | Hoechst Ag, 6230 Frankfurt | Verfahren zur gemeinsamen herstellung von carbonsaeuren und carbonsaeureanhydriden sowie ggf. carbonsaeureestern |
| EP0203286B1 (de) * | 1985-03-27 | 1988-09-14 | Hoechst Aktiengesellschaft | Trägerkatalysator und Verfahren zur Herstellung von Monocarbonsäureanhydriden |
| GB8618710D0 (en) * | 1986-07-31 | 1986-09-10 | Bp Chem Int Ltd | Recovering metals |
| DE3643894A1 (de) | 1986-12-22 | 1988-06-23 | Degussa | Rhodium-haltige organopolysiloxan-ammoniumverbindungen, verfahren zu ihrer herstellung und verwendung |
| US5185462A (en) | 1987-01-08 | 1993-02-09 | Bp Chemicals Limited | Production of carboxylic acids and esters thereof |
| GB8807284D0 (en) | 1988-03-26 | 1988-04-27 | Bp Chem Int Ltd | Chemical process |
| US5218140A (en) * | 1988-08-02 | 1993-06-08 | Union Carbide Chemicals & Plastics Technology Corporation | Carbonylation reaction and catalyst therefor |
| GB9013116D0 (en) | 1990-06-12 | 1990-08-01 | British Petroleum Co Plc | Carbonylation of methanol |
| US5488143A (en) | 1992-06-30 | 1996-01-30 | Korea Institute Of Science And Technology | Processes for the carbonylation of methanol to form acetic acid, methyl acetate and acetic anhydride |
| GB9223170D0 (en) | 1992-11-05 | 1992-12-16 | British Petroleum Co Plc | Process for preparing carboxylic acids |
| KR960006546B1 (ko) * | 1993-07-28 | 1996-05-17 | 한국과학기술연구원 | 초산에스테르의 제조 방법 |
| US5510524A (en) | 1995-02-21 | 1996-04-23 | Bp Chemicals Limited | Process for the production of a carboxylic acid |
| US5696284A (en) | 1995-06-21 | 1997-12-09 | Bp Chemicals Limited | Process for the carbonylation of alkyl alcohols and/or reactive derivatives thereof |
| GB9517184D0 (en) | 1995-08-22 | 1995-10-25 | Bp Chem Int Ltd | Process |
| US5900505A (en) | 1997-02-04 | 1999-05-04 | Eastman Chemical Company | Heterogeneous vapor phase carbonylation process |
-
1999
- 1999-08-25 US US09/383,124 patent/US6355837B1/en not_active Expired - Lifetime
-
2000
- 2000-08-11 WO PCT/US2000/022133 patent/WO2001014306A1/en not_active Ceased
- 2000-08-11 JP JP2001518399A patent/JP4523214B2/ja not_active Expired - Fee Related
- 2000-08-11 EP EP00954018A patent/EP1206434B1/en not_active Expired - Lifetime
- 2000-08-11 DE DE60011099T patent/DE60011099T2/de not_active Expired - Lifetime
- 2000-08-11 CN CNB008120064A patent/CN1192010C/zh not_active Expired - Fee Related
- 2000-08-11 BR BR0013520-8A patent/BR0013520A/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1192010C (zh) | 2005-03-09 |
| DE60011099D1 (de) | 2004-07-01 |
| JP2003507446A (ja) | 2003-02-25 |
| CN1371349A (zh) | 2002-09-25 |
| DE60011099T2 (de) | 2004-10-14 |
| EP1206434A1 (en) | 2002-05-22 |
| EP1206434B1 (en) | 2004-05-26 |
| US6355837B1 (en) | 2002-03-12 |
| BR0013520A (pt) | 2002-05-07 |
| WO2001014306A1 (en) | 2001-03-01 |
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