DE69917896T2 - Verfahren zur herstellung von essigsäureanhydrid - Google Patents
Verfahren zur herstellung von essigsäureanhydrid Download PDFInfo
- Publication number
- DE69917896T2 DE69917896T2 DE69917896T DE69917896T DE69917896T2 DE 69917896 T2 DE69917896 T2 DE 69917896T2 DE 69917896 T DE69917896 T DE 69917896T DE 69917896 T DE69917896 T DE 69917896T DE 69917896 T2 DE69917896 T2 DE 69917896T2
- Authority
- DE
- Germany
- Prior art keywords
- reaction zone
- reaction mixture
- acetic anhydride
- carbon monoxide
- liquid
- 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.)
- Expired - Lifetime
Links
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 title claims description 156
- 238000004519 manufacturing process Methods 0.000 title description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 104
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 95
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 82
- 238000006243 chemical reaction Methods 0.000 claims description 79
- 239000011541 reaction mixture Substances 0.000 claims description 56
- 239000007788 liquid Substances 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 35
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 34
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 30
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 25
- 239000010948 rhodium Substances 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 23
- 239000000376 reactant Substances 0.000 claims description 23
- 229910052703 rhodium Inorganic materials 0.000 claims description 22
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 21
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 21
- 239000007791 liquid phase Substances 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000012190 activator Substances 0.000 description 18
- 230000006315 carbonylation Effects 0.000 description 17
- 238000005810 carbonylation reaction Methods 0.000 description 17
- 239000007789 gas Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- -1 alkali metal salts Chemical class 0.000 description 8
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- LSMAIBOZUPTNBR-UHFFFAOYSA-N phosphanium;iodide Chemical class [PH4+].[I-] LSMAIBOZUPTNBR-UHFFFAOYSA-N 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 150000002496 iodine Chemical class 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- ARSMIBSHEYKMJT-UHFFFAOYSA-M 1,3-dimethylimidazolium iodide Chemical compound [I-].CN1C=C[N+](C)=C1 ARSMIBSHEYKMJT-UHFFFAOYSA-M 0.000 description 1
- BVUPLMFUPRCOEH-UHFFFAOYSA-M 1,3-dimethylpyridin-1-ium;iodide Chemical compound [I-].CC1=CC=C[N+](C)=C1 BVUPLMFUPRCOEH-UHFFFAOYSA-M 0.000 description 1
- OSNIIMCBVLBNGS-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-2-(dimethylamino)propan-1-one Chemical compound CN(C)C(C)C(=O)C1=CC=C2OCOC2=C1 OSNIIMCBVLBNGS-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- HLNJFEXZDGURGZ-UHFFFAOYSA-M 1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1 HLNJFEXZDGURGZ-UHFFFAOYSA-M 0.000 description 1
- PNYRDWUKTXFTPN-UHFFFAOYSA-M 1-methylquinolin-1-ium;iodide Chemical compound [I-].C1=CC=C2[N+](C)=CC=CC2=C1 PNYRDWUKTXFTPN-UHFFFAOYSA-M 0.000 description 1
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 1
- GOKCJCODOLGYQD-UHFFFAOYSA-N 4,6-dichloro-2-imidazol-1-ylpyrimidine Chemical compound ClC1=CC(Cl)=NC(N2C=NC=C2)=N1 GOKCJCODOLGYQD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021604 Rhodium(III) chloride Inorganic materials 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- UKFWSNCTAHXBQN-UHFFFAOYSA-N ammonium iodide Chemical class [NH4+].[I-] UKFWSNCTAHXBQN-UHFFFAOYSA-N 0.000 description 1
- 229940107816 ammonium iodide Drugs 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910001505 inorganic iodide Inorganic materials 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- JNMIXMFEVJHFNY-UHFFFAOYSA-M methyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 JNMIXMFEVJHFNY-UHFFFAOYSA-M 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- MWZNPHHDRLXXHO-UHFFFAOYSA-N rhodium;hydrate Chemical compound O.[Rh] MWZNPHHDRLXXHO-UHFFFAOYSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- CCIYPTIBRAUPLQ-UHFFFAOYSA-M tetrabutylphosphanium;iodide Chemical compound [I-].CCCC[P+](CCCC)(CCCC)CCCC CCIYPTIBRAUPLQ-UHFFFAOYSA-M 0.000 description 1
- JTFPRVNRGNKAAV-UHFFFAOYSA-M tetraoctylphosphanium;iodide Chemical compound [I-].CCCCCCCC[P+](CCCCCCCC)(CCCCCCCC)CCCCCCCC JTFPRVNRGNKAAV-UHFFFAOYSA-M 0.000 description 1
- AEFPPQGZJFTXDR-UHFFFAOYSA-M tetraphenylphosphanium;iodide Chemical compound [I-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AEFPPQGZJFTXDR-UHFFFAOYSA-M 0.000 description 1
- DXJLCRNXYNRGRA-UHFFFAOYSA-M tributyl(methyl)azanium;iodide Chemical compound [I-].CCCC[N+](C)(CCCC)CCCC DXJLCRNXYNRGRA-UHFFFAOYSA-M 0.000 description 1
- RLZMYANQLOCZOB-UHFFFAOYSA-M tributyl(methyl)phosphanium;iodide Chemical compound [I-].CCCC[P+](C)(CCCC)CCCC RLZMYANQLOCZOB-UHFFFAOYSA-M 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- WRTMQOHKMFDUKX-UHFFFAOYSA-N triiodide Chemical compound I[I-]I WRTMQOHKMFDUKX-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
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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66985 | 1998-04-24 | ||
| US09/066,985 US5922911A (en) | 1998-04-24 | 1998-04-24 | Process for the manufacture of acetic anhydride |
| PCT/US1999/008026 WO1999055658A1 (en) | 1998-04-24 | 1999-04-13 | Process for the manufacture of acetic anhydride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69917896D1 DE69917896D1 (de) | 2004-07-15 |
| DE69917896T2 true DE69917896T2 (de) | 2004-10-28 |
Family
ID=22073004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69917896T Expired - Lifetime DE69917896T2 (de) | 1998-04-24 | 1999-04-13 | Verfahren zur herstellung von essigsäureanhydrid |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5922911A (enExample) |
| EP (1) | EP1073619B1 (enExample) |
| JP (1) | JP4662624B2 (enExample) |
| CN (1) | CN1135212C (enExample) |
| BR (1) | BR9909840B1 (enExample) |
| DE (1) | DE69917896T2 (enExample) |
| WO (1) | WO1999055658A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6222070B1 (en) | 1999-09-07 | 2001-04-24 | Eastman Chemical Company | Method for reducing EDA in acetic anhydride production |
| US6596781B1 (en) | 2002-05-02 | 2003-07-22 | Chevron U.S.A. Inc. | Integrated process for preparing Fischer-Tropsch products and acetic acid from synthesis gas |
| WO2004031315A1 (ja) * | 2002-10-04 | 2004-04-15 | Nok Corporation | シール材料 |
| 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 |
| 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 |
| CN103180285B (zh) | 2010-11-12 | 2016-02-03 | 伊士曼化工公司 | 粗乙酰基混合物的精制方法 |
| JP6671177B2 (ja) * | 2013-03-07 | 2020-03-25 | ビーピー ケミカルズ リミテッドＢｐ Ｃｈｅｍｉｃａｌｓ Ｌｉｍｉｔｅｄ | プロセス |
| US8975450B2 (en) * | 2013-03-15 | 2015-03-10 | Celanese International Corporation | Ethanol and ethyl acetate production using an acetic acid and acetic anhydride mixed feed |
| CN104276939B (zh) * | 2013-07-09 | 2016-09-07 | 上海华谊工程有限公司 | 一种醋酐的生产工艺 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3927078A (en) * | 1972-08-21 | 1975-12-16 | Chevron Res | Methylene and oxymethylene bis-ester production |
| US4559183A (en) * | 1973-09-04 | 1985-12-17 | The Halcon Sd Group, Inc. | Preparation of carboxylic acid anhydrides |
| DE2450965C2 (de) * | 1974-10-26 | 1983-06-09 | Hoechst Ag, 6230 Frankfurt | Verfahren zur Herstellung von Essigsäureanhydrid |
| US4115444A (en) * | 1975-03-10 | 1978-09-19 | Halcon International, Inc. | Process for preparing carboxylic acid anhydrides |
| DE2836084A1 (de) * | 1978-08-17 | 1980-03-06 | Hoechst Ag | Verfahren zur herstellung von essigsaeureanhydrid |
| US4252741A (en) * | 1978-10-06 | 1981-02-24 | Halcon Research & Development Corp. | Carbonylation with Group VIII noble metal catalysts |
| US4374070A (en) * | 1980-11-21 | 1983-02-15 | Eastman Kodak Company | Preparation of acetic anhydride |
| NZ203225A (en) * | 1982-02-13 | 1985-01-31 | Bp Chem Int Ltd | Coproduction of monocarboxylic acids and anhydrides |
| NZ203226A (en) * | 1982-02-13 | 1985-08-30 | Bp Chemical Ltd | Production of acetic anhydride from methanol and carbon monoxide |
| US5003104A (en) * | 1987-03-03 | 1991-03-26 | Bp Chemicals Limited | Carbonylation process and catalyst |
| ES2070626T3 (es) * | 1990-12-20 | 1995-06-01 | Eastman Chem Co | Procedimiento continuo para la preparacion de anhidrido acetico o de mezclas de anhidrido acetico y acido acetico. |
| US5648531A (en) * | 1993-08-18 | 1997-07-15 | Daicel Chemical Industries, Ltd. | Process for producing acetic anhydride alone or acetic anhydride and acetic acid |
| JPH07324055A (ja) * | 1994-04-04 | 1995-12-12 | Daicel Chem Ind Ltd | 無水酢酸及び酢酸の製造法 |
| JP3308392B2 (ja) * | 1994-06-02 | 2002-07-29 | ダイセル化学工業株式会社 | カルボニル化反応方法 |
| FR2750984B1 (fr) * | 1996-07-10 | 1998-11-06 | Rhone Poulenc Chimie | Preparation d'acide acetique et/ou d'acetate de methyle par une reaction de carbonylation |
| GB9625335D0 (en) * | 1996-12-05 | 1997-01-22 | Bp Chem Int Ltd | Process |
-
1998
- 1998-04-24 US US09/066,985 patent/US5922911A/en not_active Expired - Lifetime
-
1999
- 1999-04-13 EP EP99916651A patent/EP1073619B1/en not_active Expired - Lifetime
- 1999-04-13 WO PCT/US1999/008026 patent/WO1999055658A1/en not_active Ceased
- 1999-04-13 CN CNB998053821A patent/CN1135212C/zh not_active Expired - Lifetime
- 1999-04-13 BR BRPI9909840-7A patent/BR9909840B1/pt not_active IP Right Cessation
- 1999-04-13 JP JP2000545819A patent/JP4662624B2/ja not_active Expired - Lifetime
- 1999-04-13 DE DE69917896T patent/DE69917896T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69917896D1 (de) | 2004-07-15 |
| BR9909840B1 (pt) | 2011-11-01 |
| EP1073619B1 (en) | 2004-06-09 |
| JP2002512995A (ja) | 2002-05-08 |
| BR9909840A (pt) | 2000-12-19 |
| CN1135212C (zh) | 2004-01-21 |
| US5922911A (en) | 1999-07-13 |
| CN1298380A (zh) | 2001-06-06 |
| EP1073619A1 (en) | 2001-02-07 |
| JP4662624B2 (ja) | 2011-03-30 |
| WO1999055658A1 (en) | 1999-11-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |