JP2004531576A5 - - Google Patents
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- Publication number
- JP2004531576A5 JP2004531576A5 JP2003506844A JP2003506844A JP2004531576A5 JP 2004531576 A5 JP2004531576 A5 JP 2004531576A5 JP 2003506844 A JP2003506844 A JP 2003506844A JP 2003506844 A JP2003506844 A JP 2003506844A JP 2004531576 A5 JP2004531576 A5 JP 2004531576A5
- Authority
- JP
- Japan
- Prior art keywords
- iodide
- catalyst
- carbonylation
- weight
- methyl
- 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
- 238000000034 method Methods 0.000 claims description 28
- 238000005810 carbonylation reaction Methods 0.000 claims description 20
- 230000006315 carbonylation Effects 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 229910052741 iridium Inorganic materials 0.000 claims description 11
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 11
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 9
- 150000004820 halides Chemical class 0.000 claims description 9
- 239000000376 reactant Substances 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 7
- -1 alkane polyols Chemical class 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 3
- 239000011949 solid catalyst Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 15
- 239000003054 catalyst Substances 0.000 claims 11
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 10
- 239000007789 gas Substances 0.000 claims 9
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 5
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 5
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims 5
- 229910000043 hydrogen iodide Inorganic materials 0.000 claims 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 229940102396 methyl bromide Drugs 0.000 claims 4
- IQRUSQUYPCHEKN-UHFFFAOYSA-N 2-iodobutane Chemical compound CCC(C)I IQRUSQUYPCHEKN-UHFFFAOYSA-N 0.000 claims 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 3
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 claims 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 3
- 229940071870 hydroiodic acid Drugs 0.000 claims 3
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims 3
- XJTQJERLRPWUGL-UHFFFAOYSA-N iodomethylbenzene Chemical compound ICC1=CC=CC=C1 XJTQJERLRPWUGL-UHFFFAOYSA-N 0.000 claims 3
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 239000008246 gaseous mixture Substances 0.000 claims 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 229920000570 polyether Polymers 0.000 claims 1
- 229920005862 polyol Polymers 0.000 claims 1
- 230000008016 vaporization Effects 0.000 claims 1
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000007598 dipping method Methods 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/885,403 US6617471B2 (en) | 2001-06-20 | 2001-06-20 | Method for carbonylation of lower aliphatic alcohols using tin promoted iridium catalyst |
| PCT/US2002/018992 WO2003000640A1 (en) | 2001-06-20 | 2002-06-17 | Vapor-phase carbonylation of lower aliphatic alcohols using tin promoted iridium catalyst |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004531576A JP2004531576A (ja) | 2004-10-14 |
| JP2004531576A5 true JP2004531576A5 (enExample) | 2006-01-05 |
| JP4242762B2 JP4242762B2 (ja) | 2009-03-25 |
Family
ID=25386824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003506844A Expired - Fee Related JP4242762B2 (ja) | 2001-06-20 | 2002-06-17 | 錫促進イリジウム触媒を用いた低級脂肪族アルコールの気相カルボニル化 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6617471B2 (enExample) |
| EP (1) | EP1397337B1 (enExample) |
| JP (1) | JP4242762B2 (enExample) |
| CN (1) | CN1321970C (enExample) |
| AT (1) | ATE390402T1 (enExample) |
| DE (1) | DE60225800T2 (enExample) |
| WO (1) | WO2003000640A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7198926B2 (en) | 2003-05-08 | 2007-04-03 | E. I. Du Pont De Nemours And Company | Preparation of (E)- and (Z)-2-methyl-2-butenoic acids |
| US7053241B1 (en) * | 2005-02-24 | 2006-05-30 | Celanese International Corporation | Acetic acid production methods incorporating at least one metal salt as a catalyst stabilizer |
| US8003822B2 (en) * | 2005-05-20 | 2011-08-23 | Wacker Chemie Ag | Process for continuous carbonylation by supported ionic liquid-phase catalysis |
| KR20080108605A (ko) * | 2006-04-05 | 2008-12-15 | 우드랜드 바이오퓨엘스 인크. | 합성 가스에 의해 바이오매스를 에탄올로 전환시키는 시스템 및 방법 |
| US8546486B2 (en) * | 2007-09-18 | 2013-10-01 | Ccp Composites Us Llc | Low VOC thermosetting polyester acrylic resin for gel coat |
| CN101428227B (zh) * | 2007-11-07 | 2012-05-23 | 中国科学院大连化学物理研究所 | 一种铱基双组分负载型催化剂及其制备和应用 |
| US8877963B2 (en) | 2010-09-28 | 2014-11-04 | Celanese International Corporation | Production of acetic acid with high conversion rate |
| US8394988B2 (en) | 2010-09-28 | 2013-03-12 | Celanese International Corporation | Production of acetic acid with high conversion rate |
| US9663437B2 (en) | 2011-09-13 | 2017-05-30 | Celanese International Corporation | Production of acetic acid with high conversion rate |
| US9421522B2 (en) * | 2011-12-28 | 2016-08-23 | Eastman Chemical Company | Iridium catalysts for carbonylation |
| BR112013007324B1 (pt) | 2012-02-08 | 2020-10-20 | Celanese International Corporation | produção de ácido acético com alta taxa de conversão |
| US12083504B2 (en) * | 2019-11-14 | 2024-09-10 | The Regents Of The University Of California | Catalysts and methods for gas phase carbonylation |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE364254B (enExample) | 1967-04-05 | 1974-02-18 | Monsanto Co | |
| US3597501A (en) | 1967-04-24 | 1971-08-03 | Toyo Rayon Co Ltd | Acrylic synthetic fibers having novel structure |
| GB1203174A (en) * | 1967-09-27 | 1970-08-26 | Ethyl Corp | Manufacture of carboxylic acid esters |
| 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 |
| US5144068A (en) | 1984-05-03 | 1992-09-01 | Hoechst Celanese Corporation | Methanol carbonylation process |
| EP0203286B1 (de) | 1985-03-27 | 1988-09-14 | Hoechst Aktiengesellschaft | Trägerkatalysator und Verfahren zur Herstellung von Monocarbonsäureanhydriden |
| 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 |
| US5414161A (en) | 1992-06-30 | 1995-05-09 | Korea Institute Of Science And Technology | Process for the preparation of ethanol from 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 |
| 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 |
| US6355837B1 (en) * | 1999-08-25 | 2002-03-12 | Eastman Chemical Company | Vapor phase carbonylation process using group 4 metal promoted iridium catalyst |
| US6353132B1 (en) * | 1999-08-25 | 2002-03-05 | Eastman Chemical Company | Vapor phase carbonylation process using group 5 metal promoted iridium catalyst |
-
2001
- 2001-06-20 US US09/885,403 patent/US6617471B2/en not_active Expired - Fee Related
-
2002
- 2002-06-17 AT AT02744362T patent/ATE390402T1/de not_active IP Right Cessation
- 2002-06-17 DE DE60225800T patent/DE60225800T2/de not_active Expired - Lifetime
- 2002-06-17 JP JP2003506844A patent/JP4242762B2/ja not_active Expired - Fee Related
- 2002-06-17 CN CNB028090888A patent/CN1321970C/zh not_active Expired - Fee Related
- 2002-06-17 EP EP02744362A patent/EP1397337B1/en not_active Expired - Lifetime
- 2002-06-17 WO PCT/US2002/018992 patent/WO2003000640A1/en not_active Ceased
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