UA68398C2 - Method for preparing acetic acid or methyl acetate in presence of iridium and platinum - Google Patents
Method for preparing acetic acid or methyl acetate in presence of iridium and platinum Download PDFInfo
- Publication number
- UA68398C2 UA68398C2 UA2001053084A UA2001053084A UA68398C2 UA 68398 C2 UA68398 C2 UA 68398C2 UA 2001053084 A UA2001053084 A UA 2001053084A UA 2001053084 A UA2001053084 A UA 2001053084A UA 68398 C2 UA68398 C2 UA 68398C2
- Authority
- UA
- Ukraine
- Prior art keywords
- platinum
- iridium
- reaction
- fact
- carried out
- Prior art date
Links
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims abstract description 135
- 238000000034 method Methods 0.000 title claims abstract description 84
- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 74
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 73
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims abstract description 72
- 229910052697 platinum Inorganic materials 0.000 title claims abstract description 66
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 title claims abstract description 17
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 title claims abstract description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 75
- 238000005810 carbonylation reaction Methods 0.000 claims abstract description 41
- 230000003197 catalytic effect Effects 0.000 claims abstract description 41
- 230000006315 carbonylation Effects 0.000 claims abstract description 37
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 29
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 20
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 239000007791 liquid phase Substances 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 39
- 239000012429 reaction media Substances 0.000 claims description 36
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 34
- 229910052751 metal Inorganic materials 0.000 claims description 26
- 239000002184 metal Substances 0.000 claims description 26
- 229910052703 rhodium Inorganic materials 0.000 claims description 26
- 239000010948 rhodium Substances 0.000 claims description 26
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 26
- 150000004694 iodide salts Chemical class 0.000 claims description 22
- 239000011541 reaction mixture Substances 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 239000003446 ligand Substances 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 150000004696 coordination complex Chemical class 0.000 claims description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 6
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000003057 platinum Chemical class 0.000 claims description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims 1
- 229910003446 platinum oxide Inorganic materials 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- -1 methyl formiate Chemical compound 0.000 abstract description 12
- 150000001875 compounds Chemical class 0.000 description 27
- 238000002474 experimental method Methods 0.000 description 26
- 239000000203 mixture Substances 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 19
- 150000002739 metals Chemical class 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 239000011630 iodine Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 239000013067 intermediate product Substances 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- WUHYYTYYHCHUID-UHFFFAOYSA-K iridium(3+);triiodide Chemical compound [I-].[I-].[I-].[Ir+3] WUHYYTYYHCHUID-UHFFFAOYSA-K 0.000 description 4
- 150000003058 platinum compounds Chemical class 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- 150000002504 iridium compounds Chemical class 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229940071870 hydroiodic acid Drugs 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 150000002503 iridium Chemical class 0.000 description 2
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- ZXDJCKVQKCNWEI-UHFFFAOYSA-L platinum(2+);diiodide Chemical compound [I-].[I-].[Pt+2] ZXDJCKVQKCNWEI-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 102000010410 Nogo Proteins Human genes 0.000 description 1
- 108010077641 Nogo Proteins Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- YQMZQQYIHIXCHS-UHFFFAOYSA-N [Rh].[Rh].[Ir].[Rh] Chemical compound [Rh].[Rh].[Ir].[Rh] YQMZQQYIHIXCHS-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- LEKJTGQWLAUGQA-UHFFFAOYSA-N acetyl iodide Chemical compound CC(I)=O LEKJTGQWLAUGQA-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- SXRIPRHXGZHSNU-UHFFFAOYSA-N iridium rhodium Chemical compound [Rh].[Ir] SXRIPRHXGZHSNU-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- KXAHUXSHRWNTOD-UHFFFAOYSA-K rhodium(3+);triiodide Chemical compound [Rh+3].[I-].[I-].[I-] KXAHUXSHRWNTOD-UHFFFAOYSA-K 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
-
- 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 |
|---|---|---|---|
| FR9813954A FR2785606B1 (fr) | 1998-11-05 | 1998-11-05 | Preparation d'acide acetique et/ou d'acetate de methyle en presence d'iridium et de platine |
| PCT/FR1999/002652 WO2000027785A1 (fr) | 1998-11-05 | 1999-10-29 | Preparation d'acide acetique et/ou d'acetate de methyle en presence d'iridium et de platine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA68398C2 true UA68398C2 (en) | 2004-08-16 |
Family
ID=9532421
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2001053084A UA68398C2 (en) | 1998-11-05 | 1999-10-29 | Method for preparing acetic acid or methyl acetate in presence of iridium and platinum |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6916952B1 (id) |
| EP (1) | EP1127042B1 (id) |
| JP (1) | JP4066305B2 (id) |
| KR (1) | KR100687510B1 (id) |
| CN (1) | CN1216845C (id) |
| AT (1) | ATE245619T1 (id) |
| AU (1) | AU6348499A (id) |
| CA (1) | CA2348472C (id) |
| DE (1) | DE69909816T2 (id) |
| ES (1) | ES2205888T3 (id) |
| FR (1) | FR2785606B1 (id) |
| ID (1) | ID28477A (id) |
| MY (1) | MY121111A (id) |
| RU (1) | RU2220129C2 (id) |
| TW (1) | TW522146B (id) |
| UA (1) | UA68398C2 (id) |
| WO (1) | WO2000027785A1 (id) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2820422B1 (fr) * | 2001-02-08 | 2003-04-25 | Acetex Chimie | Modification du systeme catalytique dans un procede industriel de fabrication d'acide acetique et/ou d'acetate de methyle |
| CA2496839A1 (en) | 2004-07-19 | 2006-01-19 | Woodland Chemical Systems Inc. | Process for producing ethanol from synthesis gas rich in carbon monoxide |
| KR20080108605A (ko) | 2006-04-05 | 2008-12-15 | 우드랜드 바이오퓨엘스 인크. | 합성 가스에 의해 바이오매스를 에탄올로 전환시키는 시스템 및 방법 |
| CN102442897B (zh) * | 2010-10-13 | 2014-05-28 | 中国石油化工股份有限公司 | 一种羰基化反应制备乙酸的方法 |
| CN102366724B (zh) * | 2011-12-01 | 2013-05-15 | 重庆大学 | 一种甲醇羰基化合成醋酸的催化剂体系及应用 |
| CN110642698A (zh) * | 2019-10-31 | 2020-01-03 | 江苏润普食品科技股份有限公司 | 山梨酸聚酯酸解制备山梨酸的生产方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE364254B (id) * | 1967-04-05 | 1974-02-18 | Monsanto Co | |
| FR2746795B1 (fr) * | 1996-03-27 | 1998-06-19 | Rhone Poulenc Chimie | Procede de preparation d'acide acetique et/ou d'acetate de methyle par isomerisation et carbonylation |
| FR2750985B1 (fr) * | 1996-07-10 | 1998-11-06 | Rhone Poulenc Chimie | Procede de preparation d'acide acetique et/ou d'acetate de methyle par carbonylation en presence d'iridium et de rhodium |
| US5900505A (en) * | 1997-02-04 | 1999-05-04 | Eastman Chemical Company | Heterogeneous vapor phase carbonylation process |
-
1998
- 1998-11-05 FR FR9813954A patent/FR2785606B1/fr not_active Expired - Fee Related
-
1999
- 1999-10-29 AT AT99950883T patent/ATE245619T1/de not_active IP Right Cessation
- 1999-10-29 DE DE69909816T patent/DE69909816T2/de not_active Expired - Lifetime
- 1999-10-29 ES ES99950883T patent/ES2205888T3/es not_active Expired - Lifetime
- 1999-10-29 JP JP2000580967A patent/JP4066305B2/ja not_active Expired - Fee Related
- 1999-10-29 CN CN998128880A patent/CN1216845C/zh not_active Expired - Fee Related
- 1999-10-29 EP EP99950883A patent/EP1127042B1/fr not_active Expired - Lifetime
- 1999-10-29 KR KR1020017005479A patent/KR100687510B1/ko not_active IP Right Cessation
- 1999-10-29 CA CA002348472A patent/CA2348472C/en not_active Expired - Fee Related
- 1999-10-29 RU RU2001111864/04A patent/RU2220129C2/ru not_active IP Right Cessation
- 1999-10-29 US US09/807,434 patent/US6916952B1/en not_active Expired - Lifetime
- 1999-10-29 UA UA2001053084A patent/UA68398C2/uk unknown
- 1999-10-29 AU AU63484/99A patent/AU6348499A/en not_active Abandoned
- 1999-10-29 WO PCT/FR1999/002652 patent/WO2000027785A1/fr active IP Right Grant
- 1999-10-29 ID IDW00200100993A patent/ID28477A/id unknown
- 1999-11-03 MY MYPI99004766A patent/MY121111A/en unknown
- 1999-11-05 TW TW088119347A patent/TW522146B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US6916952B1 (en) | 2005-07-12 |
| CA2348472A1 (en) | 2000-05-18 |
| EP1127042A1 (fr) | 2001-08-29 |
| FR2785606A1 (fr) | 2000-05-12 |
| FR2785606B1 (fr) | 2001-01-26 |
| EP1127042B1 (fr) | 2003-07-23 |
| MY121111A (en) | 2005-12-30 |
| ATE245619T1 (de) | 2003-08-15 |
| JP2002529436A (ja) | 2002-09-10 |
| KR20010103633A (ko) | 2001-11-23 |
| WO2000027785A1 (fr) | 2000-05-18 |
| CN1216845C (zh) | 2005-08-31 |
| CA2348472C (en) | 2009-03-31 |
| DE69909816D1 (de) | 2003-08-28 |
| KR100687510B1 (ko) | 2007-02-27 |
| DE69909816T2 (de) | 2004-06-03 |
| CN1325374A (zh) | 2001-12-05 |
| AU6348499A (en) | 2000-05-29 |
| ID28477A (id) | 2001-05-31 |
| ES2205888T3 (es) | 2004-05-01 |
| RU2220129C2 (ru) | 2003-12-27 |
| JP4066305B2 (ja) | 2008-03-26 |
| TW522146B (en) | 2003-03-01 |
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