JP4188817B2 - タングステン促進第ｖｉｉｉ族触媒を用いた低級アルキルアルコールの気相カルボニル化 - Google Patents
タングステン促進第ｖｉｉｉ族触媒を用いた低級アルキルアルコールの気相カルボニル化 Download PDFInfo
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- JP4188817B2 JP4188817B2 JP2003506843A JP2003506843A JP4188817B2 JP 4188817 B2 JP4188817 B2 JP 4188817B2 JP 2003506843 A JP2003506843 A JP 2003506843A JP 2003506843 A JP2003506843 A JP 2003506843A JP 4188817 B2 JP4188817 B2 JP 4188817B2
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- catalyst
- carbonylation
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- 239000003054 catalyst Substances 0.000 title claims abstract description 151
- 238000005810 carbonylation reaction Methods 0.000 title claims abstract description 94
- 230000006315 carbonylation Effects 0.000 title claims abstract description 86
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 title claims abstract description 58
- 229910052721 tungsten Inorganic materials 0.000 title claims abstract description 50
- 239000010937 tungsten Substances 0.000 title claims abstract description 49
- 125000005233 alkylalcohol group Chemical group 0.000 title claims abstract description 20
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 81
- 238000000034 method Methods 0.000 claims abstract description 72
- 229910052751 metal Inorganic materials 0.000 claims abstract description 68
- 239000002184 metal Substances 0.000 claims abstract description 68
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 62
- 239000000203 mixture Substances 0.000 claims abstract description 56
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 38
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 31
- 239000000463 material Substances 0.000 claims abstract description 28
- 239000000376 reactant Substances 0.000 claims abstract description 23
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 69
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 23
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 21
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 12
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 11
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- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 8
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- 125000000217 alkyl group Chemical group 0.000 claims description 6
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- -1 alkane polyols Chemical class 0.000 claims description 5
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 5
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
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- 239000000919 ceramic Substances 0.000 claims description 4
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000395 magnesium oxide Substances 0.000 claims description 4
- 239000000391 magnesium silicate Substances 0.000 claims description 4
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- 235000019792 magnesium silicate Nutrition 0.000 claims description 4
- 239000008262 pumice Substances 0.000 claims description 4
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 4
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 4
- IQRUSQUYPCHEKN-UHFFFAOYSA-N 2-iodobutane Chemical compound CCC(C)I IQRUSQUYPCHEKN-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims description 3
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 claims description 3
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- 229910052570 clay Inorganic materials 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims description 3
- XJTQJERLRPWUGL-UHFFFAOYSA-N iodomethylbenzene Chemical compound ICC1=CC=CC=C1 XJTQJERLRPWUGL-UHFFFAOYSA-N 0.000 claims description 3
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- 150000001502 aryl halides Chemical class 0.000 claims description 2
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
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- 229920000570 polyether Polymers 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 30
- 150000001735 carboxylic acids Chemical class 0.000 abstract description 9
- 239000012808 vapor phase Substances 0.000 abstract description 7
- 230000000052 comparative effect Effects 0.000 description 34
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- 239000000243 solution Substances 0.000 description 22
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 20
- 229910052703 rhodium Inorganic materials 0.000 description 20
- 239000010948 rhodium Substances 0.000 description 20
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 14
- 229910052741 iridium Inorganic materials 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 239000010453 quartz Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 10
- 239000007791 liquid phase Substances 0.000 description 10
- 229910052759 nickel Inorganic materials 0.000 description 10
- 239000012153 distilled water Substances 0.000 description 8
- 239000002638 heterogeneous catalyst Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 7
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- 230000000694 effects Effects 0.000 description 5
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- 229910052723 transition metal Inorganic materials 0.000 description 5
- 150000003624 transition metals Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- 239000003446 ligand Substances 0.000 description 4
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- 239000000543 intermediate Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- YOLNUNVVUJULQZ-UHFFFAOYSA-J iridium;tetrachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Ir] YOLNUNVVUJULQZ-UHFFFAOYSA-J 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
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000000155 melt Substances 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
- 229940078487 nickel acetate tetrahydrate Drugs 0.000 description 1
- LJHGLTHLRNZONI-UHFFFAOYSA-J nickel(2+) tetraacetate tetrahydrate Chemical compound [Ni+2].O.O.O.O.C(C)(=O)[O-].[Ni+2].C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-] LJHGLTHLRNZONI-UHFFFAOYSA-J 0.000 description 1
- OINIXPNQKAZCRL-UHFFFAOYSA-L nickel(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Ni+2].CC([O-])=O.CC([O-])=O OINIXPNQKAZCRL-UHFFFAOYSA-L 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
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 1
- VVRQVWSVLMGPRN-UHFFFAOYSA-N oxotungsten Chemical class [W]=O VVRQVWSVLMGPRN-UHFFFAOYSA-N 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000013460 polyoxometalate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method 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
- 230000008707 rearrangement Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003284 rhodium compounds Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance 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
- 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
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/884,938 US6646154B2 (en) | 2001-06-20 | 2001-06-20 | Method for carbonylation of lower alkyl alcohols using tungsten promoted group VIII catalyst |
| PCT/US2002/018990 WO2003000639A1 (en) | 2001-06-20 | 2002-06-17 | Vapor-phase carbonylation of lower alkyl alcohols using tungsten promoted group viii catalyst |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004531575A JP2004531575A (ja) | 2004-10-14 |
| JP2004531575A5 JP2004531575A5 (enExample) | 2006-01-05 |
| JP4188817B2 true JP4188817B2 (ja) | 2008-12-03 |
Family
ID=25385766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003506843A Expired - Fee Related JP4188817B2 (ja) | 2001-06-20 | 2002-06-17 | タングステン促進第ｖｉｉｉ族触媒を用いた低級アルキルアルコールの気相カルボニル化 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6646154B2 (enExample) |
| EP (1) | EP1397338B1 (enExample) |
| JP (1) | JP4188817B2 (enExample) |
| CN (1) | CN1255373C (enExample) |
| AT (1) | ATE414684T1 (enExample) |
| DE (1) | DE60229937D1 (enExample) |
| WO (1) | WO2003000639A1 (enExample) |
Family Cites Families (26)
| 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 |
| US4625049A (en) | 1982-06-30 | 1986-11-25 | Chevron Research Company | Alcohol carbonylation process using a bimetallic nickel catalyst |
| 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 |
| WO1998033590A1 (en) | 1997-02-04 | 1998-08-06 | Eastman Chemical Company | Carbonylation catalyst |
| WO2000048979A1 (en) | 1999-02-16 | 2000-08-24 | Eastman Chemical Company | Catalyst having solid and vaporous component for the carbonylation of lower alkyl alcohols |
| US6160163A (en) | 1999-02-16 | 2000-12-12 | Eastman Chemical Company | Method for the vapor-phase carbonylation of lower aliphatic alcohols using a supported platinum catalyst and halide promoter |
-
2001
- 2001-06-20 US US09/884,938 patent/US6646154B2/en not_active Expired - Fee Related
-
2002
- 2002-06-17 CN CN02812378.6A patent/CN1255373C/zh not_active Expired - Fee Related
- 2002-06-17 AT AT02746543T patent/ATE414684T1/de not_active IP Right Cessation
- 2002-06-17 DE DE60229937T patent/DE60229937D1/de not_active Expired - Lifetime
- 2002-06-17 WO PCT/US2002/018990 patent/WO2003000639A1/en not_active Ceased
- 2002-06-17 EP EP02746543A patent/EP1397338B1/en not_active Expired - Lifetime
- 2002-06-17 JP JP2003506843A patent/JP4188817B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1518533A (zh) | 2004-08-04 |
| ATE414684T1 (de) | 2008-12-15 |
| DE60229937D1 (de) | 2009-01-02 |
| CN1255373C (zh) | 2006-05-10 |
| US6646154B2 (en) | 2003-11-11 |
| JP2004531575A (ja) | 2004-10-14 |
| WO2003000639A1 (en) | 2003-01-03 |
| EP1397338B1 (en) | 2008-11-19 |
| US20030060660A1 (en) | 2003-03-27 |
| EP1397338A1 (en) | 2004-03-17 |
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