JP2003530378A5 - - Google Patents
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- JP2003530378A5 JP2003530378A5 JP2001575539A JP2001575539A JP2003530378A5 JP 2003530378 A5 JP2003530378 A5 JP 2003530378A5 JP 2001575539 A JP2001575539 A JP 2001575539A JP 2001575539 A JP2001575539 A JP 2001575539A JP 2003530378 A5 JP2003530378 A5 JP 2003530378A5
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- JP
- Japan
- Prior art keywords
- group
- mixtures
- metal
- catalyst
- supported
- 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.)
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- 238000000034 method Methods 0.000 description 30
- 239000000203 mixture Substances 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 229910052751 metal Inorganic materials 0.000 description 19
- 239000002184 metal Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 16
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 9
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 9
- 230000006315 carbonylation Effects 0.000 description 9
- 238000005810 carbonylation reaction Methods 0.000 description 9
- 239000011159 matrix material Substances 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Polymers C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- -1 alkane polyol Chemical class 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 229940102396 methyl bromide Drugs 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Polymers C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000005233 alkylalcohol group Chemical group 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 229910052741 iridium Inorganic materials 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 229910052762 osmium Inorganic materials 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 229910052703 rhodium Inorganic materials 0.000 description 4
- 239000010948 rhodium Substances 0.000 description 4
- 229910052707 ruthenium Inorganic materials 0.000 description 4
- 229910052718 tin Inorganic materials 0.000 description 4
- 239000011135 tin Substances 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 229910052735 hafnium Inorganic materials 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 229910052747 lanthanoid Inorganic materials 0.000 description 3
- 150000002602 lanthanoids Chemical class 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 229910052758 niobium Inorganic materials 0.000 description 3
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229910052702 rhenium Inorganic materials 0.000 description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
- 229910052715 tantalum Inorganic materials 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- 229910052721 tungsten Inorganic materials 0.000 description 3
- 229910052720 vanadium Inorganic materials 0.000 description 3
- 229910052726 zirconium Inorganic materials 0.000 description 3
- IQRUSQUYPCHEKN-UHFFFAOYSA-N 2-iodobutane Chemical compound CCC(C)I IQRUSQUYPCHEKN-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001503 aryl iodides Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229940071870 hydroiodic acid Drugs 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- XJTQJERLRPWUGL-UHFFFAOYSA-N iodomethylbenzene Chemical compound ICC1=CC=CC=C1 XJTQJERLRPWUGL-UHFFFAOYSA-N 0.000 description 2
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 2
- 229910052684 Cerium Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229910052777 Praseodymium Inorganic materials 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/544,639 US6452043B1 (en) | 2000-04-05 | 2000-04-05 | Carbonylation of lower alkyl alcohols and their derivatives using metals supported on carbonized polysulfonated divinylbenzene-styrene copolymers |
| US09/544,639 | 2000-04-05 | ||
| PCT/US2001/007729 WO2001077059A2 (en) | 2000-04-05 | 2001-03-12 | Carbonylation of lower alkyl alcohols and their derivatives using metals supported on carbonized polysulfonated divinylbenzene-styrene copolymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003530378A JP2003530378A (ja) | 2003-10-14 |
| JP2003530378A5 true JP2003530378A5 (enExample) | 2008-04-10 |
Family
ID=24172985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001575539A Pending JP2003530378A (ja) | 2000-04-05 | 2001-03-12 | 炭化ポリスルホン化ジビニルベンゼン−スチレンコポリマー上に支持されている金属を使用する低級アルキルアルコールおよびそれらの誘導体のカルボニル化 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6452043B1 (enExample) |
| EP (1) | EP1268392B1 (enExample) |
| JP (1) | JP2003530378A (enExample) |
| CN (1) | CN1232498C (enExample) |
| AT (1) | ATE267159T1 (enExample) |
| BR (1) | BR0109829A (enExample) |
| DE (1) | DE60103387T2 (enExample) |
| WO (1) | WO2001077059A2 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6235673B1 (en) * | 2000-04-05 | 2001-05-22 | Eastman Chemical Company | Carbonylation catalyst supported on a carbonized polysulfonated divinylbenzene-styrene copolymer |
| US6613938B2 (en) * | 2001-06-19 | 2003-09-02 | Eastman Chemical Company | Method for carbonylation of lower aliphatic alcohols using tin promoted platinum catalyst |
| WO2004024323A1 (ja) * | 2002-09-13 | 2004-03-25 | Wako Pure Chemical Industries, Ltd. | パラジウム触媒組成物 |
| US20050049434A1 (en) * | 2003-08-28 | 2005-03-03 | Tustin Gerald Charles | Fluidizable carbon catalysts |
| EP1966115B1 (en) * | 2005-12-21 | 2011-04-20 | BP Chemicals Limited | Carbonylation process |
| GB0601863D0 (en) * | 2006-01-30 | 2006-03-08 | Bp Chem Int Ltd | Process |
| US7737298B2 (en) * | 2006-06-09 | 2010-06-15 | Eastman Chemical Company | Production of acetic acid and mixtures of acetic acid and acetic anhydride |
| US7582792B2 (en) * | 2006-06-15 | 2009-09-01 | Eastman Chemical Company | Carbonylation process |
| US7253304B1 (en) | 2006-06-20 | 2007-08-07 | Eastman Chemical Company | Carbonylation process |
| US7629491B2 (en) * | 2006-06-26 | 2009-12-08 | Eastman Chemical Company | Hydrocarboxylation process |
| JP4800902B2 (ja) * | 2006-11-06 | 2011-10-26 | エヌ・イーケムキャット株式会社 | 選択的官能基還元性能を有するＰｄ担持ポリマー触媒 |
| US20090247783A1 (en) * | 2008-04-01 | 2009-10-01 | Eastman Chemical Company | Carbonylation process |
| US9012683B2 (en) | 2010-11-12 | 2015-04-21 | Eastman Chemical Company | Coproduction of acetic acid and acetic anhydride |
| CN106140156A (zh) * | 2015-04-20 | 2016-11-23 | 中国科学院大连化学物理研究所 | 一种活性炭负载的铑基催化剂及其制备方法和应用 |
| CN106807367A (zh) * | 2015-12-02 | 2017-06-09 | 中国科学院大连化学物理研究所 | 一种碳基材料负载的铱基催化剂及其制备方法和应用 |
| CN106807368A (zh) * | 2015-12-02 | 2017-06-09 | 中国科学院大连化学物理研究所 | 一种活性炭负载的铱基催化剂及其制备方法和应用 |
| CN111111775A (zh) * | 2018-11-01 | 2020-05-08 | 中国科学院大连化学物理研究所 | 有机含膦聚合物载体负载的Rh基催化剂及其制备和应用 |
| KR20220024166A (ko) * | 2019-05-28 | 2022-03-03 | 에너켐 인코포레이티드 | 기상 메탄올 카르보닐화 촉매 |
| WO2023035030A1 (en) * | 2021-09-07 | 2023-03-16 | Monash University | Process for producing an organic acid, and catalyst for same |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3717670A (en) | 1968-08-02 | 1973-02-20 | Monsanto Co | Production of carboxylic acids and esters |
| US3689533A (en) | 1971-03-15 | 1972-09-05 | Monsanto Co | Production of carboxylic acids and esters |
| US4323698A (en) * | 1978-12-04 | 1982-04-06 | Mobil Oil Corporation | Resin-metal compound complex for catalyzing chemical reactions |
| US4328125A (en) | 1979-05-14 | 1982-05-04 | University Of Illinois Foundation | Heterogeneous anionic transition metal catalysts |
| US4417077A (en) | 1980-10-01 | 1983-11-22 | University Of Illinois Foundation | Heterogeneous anionic transition metal catalysts |
| 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 |
| 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 |
| US5155261A (en) | 1987-02-05 | 1992-10-13 | Reilly Industries, Inc. | Process for acetic acid preparation and heterogenous catalyst for same |
| US4839311A (en) | 1987-08-14 | 1989-06-13 | National Semiconductor Corporation | Etch back detection |
| GB9013116D0 (en) | 1990-06-12 | 1990-08-01 | British Petroleum Co Plc | Carbonylation of methanol |
| DE4215907C2 (de) * | 1992-05-14 | 2003-02-13 | Mhb Filtration Gmbh & Co Kg | Katalysatoren auf Basis von karbonisierten Ionenaustauschern |
| 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 |
| GB9303770D0 (en) | 1993-02-25 | 1993-04-14 | Bp Chem Int Ltd | Process |
| US5364963A (en) | 1993-04-30 | 1994-11-15 | Chiyoda Corporation | Supported rhodium catalyst, method of preparing same and process of producing acetic acid by methanol carbonylation using same |
| US5488023A (en) * | 1994-08-12 | 1996-01-30 | Corning Incorporated | Method of making activated carbon having dispersed catalyst |
| US5510524A (en) | 1995-02-21 | 1996-04-23 | Bp Chemicals Limited | Process for the production of a carboxylic acid |
| GB9626317D0 (en) * | 1996-12-19 | 1997-02-05 | Bp Chem Int Ltd | Process |
| WO1998033590A1 (en) * | 1997-02-04 | 1998-08-06 | Eastman Chemical Company | Carbonylation catalyst |
| US5900505A (en) | 1997-02-04 | 1999-05-04 | Eastman Chemical Company | Heterogeneous vapor phase carbonylation process |
| US6235673B1 (en) * | 2000-04-05 | 2001-05-22 | Eastman Chemical Company | Carbonylation catalyst supported on a carbonized polysulfonated divinylbenzene-styrene copolymer |
-
2000
- 2000-04-05 US US09/544,639 patent/US6452043B1/en not_active Expired - Lifetime
-
2001
- 2001-03-12 EP EP01920289A patent/EP1268392B1/en not_active Expired - Lifetime
- 2001-03-12 BR BR0109829-2A patent/BR0109829A/pt not_active Application Discontinuation
- 2001-03-12 DE DE60103387T patent/DE60103387T2/de not_active Expired - Fee Related
- 2001-03-12 JP JP2001575539A patent/JP2003530378A/ja active Pending
- 2001-03-12 CN CNB018077285A patent/CN1232498C/zh not_active Expired - Fee Related
- 2001-03-12 WO PCT/US2001/007729 patent/WO2001077059A2/en not_active Ceased
- 2001-03-12 AT AT01920289T patent/ATE267159T1/de not_active IP Right Cessation
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