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 PDF

Info

Publication number: UA68398C2
Authority: UA; Ukraine
Prior art keywords: platinum; iridium; reaction; fact; carried out
Prior art date: 1998-11-05

Application number

UA2001053084A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Acetex Chimie

Priority date (The priority date 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 date listed.)

1998-11-05

Filing date

1999-10-29

Publication date

2004-08-16

1999-10-29 Application filed by Acetex Chimie filed Critical Acetex Chimie

2004-08-16 Publication of UA68398C2 publication Critical patent/UA68398C2/uk

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)

UA2001053084A 1998-11-05 1999-10-29 Method for preparing acetic acid or methyl acetate in presence of iridium and platinum UA68398C2 (en)

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 (de)
EP (1)	EP1127042B1 (de)
JP (1)	JP4066305B2 (de)
KR (1)	KR100687510B1 (de)
CN (1)	CN1216845C (de)
AT (1)	ATE245619T1 (de)
AU (1)	AU6348499A (de)
CA (1)	CA2348472C (de)
DE (1)	DE69909816T2 (de)
ES (1)	ES2205888T3 (de)
FR (1)	FR2785606B1 (de)
ID (1)	ID28477A (de)
MY (1)	MY121111A (de)
RU (1)	RU2220129C2 (de)
TW (1)	TW522146B (de)
UA (1)	UA68398C2 (de)
WO (1)	WO2000027785A1 (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
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
US8088832B2 (en) *	2006-04-05	2012-01-03	Woodland Biofuels Inc.	System and method for converting biomass to ethanol via syngas
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 (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE364254B (de) *	1967-04-05	1974-02-18	Monsanto Co
ZA853339B (en) *	1984-05-03	1985-12-24	Celanese Corp	Methanol carbonylation process
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 DE DE69909816T patent/DE69909816T2/de not_active Expired - Lifetime
- 1999-10-29 RU RU2001111864/04A patent/RU2220129C2/ru not_active IP Right Cessation
- 1999-10-29 JP JP2000580967A patent/JP4066305B2/ja not_active Expired - Fee Related
- 1999-10-29 WO PCT/FR1999/002652 patent/WO2000027785A1/fr not_active Ceased
- 1999-10-29 CA CA002348472A patent/CA2348472C/en not_active Expired - Fee Related
- 1999-10-29 CN CN998128880A patent/CN1216845C/zh not_active Expired - Fee Related
- 1999-10-29 KR KR1020017005479A patent/KR100687510B1/ko not_active Expired - Fee Related
- 1999-10-29 ID IDW00200100993A patent/ID28477A/id unknown
- 1999-10-29 US US09/807,434 patent/US6916952B1/en not_active Expired - Lifetime
- 1999-10-29 EP EP99950883A patent/EP1127042B1/de not_active Expired - Lifetime
- 1999-10-29 ES ES99950883T patent/ES2205888T3/es not_active Expired - Lifetime
- 1999-10-29 AU AU63484/99A patent/AU6348499A/en not_active Abandoned
- 1999-10-29 UA UA2001053084A patent/UA68398C2/uk unknown
- 1999-10-29 AT AT99950883T patent/ATE245619T1/de not_active IP Right Cessation
- 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
EP1127042B1 (de)	2003-07-23
KR100687510B1 (ko)	2007-02-27
ES2205888T3 (es)	2004-05-01
ID28477A (id)	2001-05-31
TW522146B (en)	2003-03-01
FR2785606B1 (fr)	2001-01-26
FR2785606A1 (fr)	2000-05-12
JP2002529436A (ja)	2002-09-10
CA2348472A1 (en)	2000-05-18
CN1325374A (zh)	2001-12-05
AU6348499A (en)	2000-05-29
CA2348472C (en)	2009-03-31
DE69909816T2 (de)	2004-06-03
WO2000027785A1 (fr)	2000-05-18
US6916952B1 (en)	2005-07-12
RU2220129C2 (ru)	2003-12-27
EP1127042A1 (de)	2001-08-29
KR20010103633A (ko)	2001-11-23
MY121111A (en)	2005-12-30
ATE245619T1 (de)	2003-08-15
CN1216845C (zh)	2005-08-31
JP4066305B2 (ja)	2008-03-26
DE69909816D1 (de)	2003-08-28

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