JP2003509515A - 多座ホスファイト配位子を用いるヒドロホルミル化 - Google Patents

多座ホスファイト配位子を用いるヒドロホルミル化

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Publication number
JP2003509515A
JP2003509515A JP2001525002A JP2001525002A JP2003509515A JP 2003509515 A JP2003509515 A JP 2003509515A JP 2001525002 A JP2001525002 A JP 2001525002A JP 2001525002 A JP2001525002 A JP 2001525002A JP 2003509515 A JP2003509515 A JP 2003509515A
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JP
Japan
Prior art keywords
independently
alkyl
aryl
formula
cho
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.)
Pending
Application number
JP2001525002A
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English (en)
Japanese (ja)
Other versions
JP2003509515A5 (enExample
Inventor
イー．ブネル エミリオ
エス．エム．ルー ヘレン
ジーン モロイ ケネス
エイチ．フィリップス ショーン
イー．シュワイバート キャスリン
タム ウィルソン
ラデュ ノーラ
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of JP2003509515A publication Critical patent/JP2003509515A/ja
Publication of JP2003509515A5 publication Critical patent/JP2003509515A5/ja
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/40—Introducing phosphorus atoms or phosphorus-containing groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
    • B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/117—Esters of phosphoric acids with cycloaliphatic alcohols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/141—Esters of phosphorous acids
    • C07F9/145—Esters of phosphorous acids with hydroxyaryl compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/6574—Esters of oxyacids of phosphorus
    • C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0261—Complexes comprising ligands with non-tetrahedral chirality
    • B01J2531/0266—Axially chiral or atropisomeric ligands, e.g. bulky biaryls such as donor-substituted binaphthalenes, e.g. "BINAP" or "BINOL"
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/822—Rhodium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/824—Palladium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/827—Iridium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/828—Platinum
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/845—Cobalt
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
    • B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
JP2001525002A 1999-09-20 2000-09-14 多座ホスファイト配位子を用いるヒドロホルミル化 Pending JP2003509515A (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/399,252 US6307107B1 (en) 1999-09-20 1999-09-20 Hydroformylation of acyclic monoethylenically unsaturated compounds to corresponding terminal aldehydes
US09/399,252 1999-09-20
PCT/US2000/025122 WO2001021627A1 (en) 1999-09-20 2000-09-14 Hydroformylation using multidentate phosphite ligands

Publications (2)

Publication Number Publication Date
JP2003509515A true JP2003509515A (ja) 2003-03-11
JP2003509515A5 JP2003509515A5 (enExample) 2007-10-04

Family

ID=23578804

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2001525002A Pending JP2003509515A (ja) 1999-09-20 2000-09-14 多座ホスファイト配位子を用いるヒドロホルミル化

Country Status (15)

Country Link
US (2) US6307107B1 (enExample)
EP (1) EP1216252B1 (enExample)
JP (1) JP2003509515A (enExample)
KR (1) KR100644303B1 (enExample)
CN (1) CN1145633C (enExample)
AU (1) AU7378200A (enExample)
BR (1) BR0014572A (enExample)
CA (1) CA2380626C (enExample)
CZ (1) CZ2002955A3 (enExample)
DE (1) DE60006561T2 (enExample)
MX (1) MXPA02002988A (enExample)
PL (1) PL202488B1 (enExample)
SK (1) SK3932002A3 (enExample)
TW (1) TW581769B (enExample)
WO (1) WO2001021627A1 (enExample)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004513950A (ja) * 2000-11-17 2004-05-13 ザ　ペン　ステイト　リサーチ　ファンデーション オルト置換キラルホスフィンおよびホスフィナイトならびに非対称触媒反応でのその使用
JP2004149460A (ja) * 2002-10-30 2004-05-27 Mitsubishi Chemicals Corp 固体担持有機リン化合物、遷移金属錯体、及び触媒反応方法
JP2016511282A (ja) * 2013-03-14 2016-04-14 ユニバーシティ オブ マカオＵｎｉｖｅｒｓｉｔｙ Ｏｆ Ｍａｃａｕ ヤクチ（益智（ａｌｐｉｎｉａｅｏｘｙｐｈｙｌｌａｅｆｒｕｃｔｕｓ））およびその全合成から単離される新規な抗神経変性天然化合物

Families Citing this family (25)

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US6984604B2 (en) 2001-11-26 2006-01-10 Invista North America S.A.R.L. Supported bis(phosphorus) ligands and their use in the catalysis
US6750362B2 (en) * 2002-03-12 2004-06-15 E. I. Du Pont De Nemours And Company Process for making 5-formylvaleronitrile using reactivated catalyst
MXPA05002283A (es) 2002-08-31 2005-06-08 Oxeno Olefinchemie Gmbh Procedimiento para la hidroformilacion de compuestos olefinicamente insaturados, en particular olefinas, en presencia de esteres de acido carbonico ciclicos.
US6906218B2 (en) 2002-12-18 2005-06-14 Invista North America S.A.R.L. Cyclohexane derivatives and methods for their preparation
FR2849027B1 (fr) * 2002-12-23 2005-01-21 Rhodia Polyamide Intermediates Procede de synthese de composes comprenant des fonctions nitriles a partir de composes a insaturations ethyleniques
US6936171B2 (en) * 2003-01-08 2005-08-30 Invista North America S.A.R.L. Process for catalyst recovery from hydrocyanation product mixtures
US6897329B2 (en) * 2003-01-14 2005-05-24 Invista North America S.A.R.L. Process for the preparation of nickel/phosphorous ligand catalyst for olefin hydrocyanation
FR2850966B1 (fr) 2003-02-10 2005-03-18 Rhodia Polyamide Intermediates Procede de fabrication de composes dinitriles
US6844289B2 (en) * 2003-04-08 2005-01-18 Invista North America S.A.R.L. Process for the preparation of a nickel/phosphorous ligand catalyst
FR2854892B1 (fr) * 2003-05-12 2005-06-24 Rhodia Polyamide Intermediates Procede de fabrication de dinitriles
FR2854891B1 (fr) 2003-05-12 2006-07-07 Rhodia Polyamide Intermediates Procede de preparation de dinitriles
JP2007505123A (ja) 2003-09-11 2007-03-08 インヴィスタ テクノロジー エスアエルエル 不飽和カルボン酸誘導体のヒドロシアン化方法
US8119829B2 (en) * 2004-09-08 2012-02-21 Invista North America S.A.R.L. Process of hydrocyanation of unsaturated carboxylic acid derivatives
CZ2008547A3 (cs) * 2006-03-17 2009-06-10 Invista Technologies S. A. R. L. Zpusob purifikace triorganofosfitu ošetrením bazickým aditivem
CA2647396C (en) 2006-03-17 2014-01-07 University Of Kansas Tuning product selectivity in catalytic hydroformylation reactions with carbon dioxide expanded liquids
US7709674B2 (en) * 2006-07-14 2010-05-04 Invista North America S.A R.L Hydrocyanation process with reduced yield losses
US7586010B2 (en) * 2006-12-21 2009-09-08 Eastman Chemical Company Phosphonite-containing catalysts for hydroformylation processes
JP5670909B2 (ja) 2008-11-14 2015-02-18 ユニバーシティ・オブ・カンザス ポリマーに担持された遷移金属触媒錯体、及びその使用方法
CN103547349B (zh) 2011-12-21 2016-03-16 因温斯特北美公司 用于减少稳定乳液的萃取溶剂控制
KR20140127220A (ko) 2011-12-21 2014-11-03 인비스타 테크놀러지스 에스.에이 알.엘. 안정한 에멀젼을 감소시키기 위한 추출 용매 제어
EP2794045B1 (en) 2011-12-21 2016-12-21 Invista Technologies S.à.r.l. Extraction solvent control for reducing stable emulsions
US9133223B2 (en) 2011-12-21 2015-09-15 Invista North America S.A.R.L. Extraction solvent control for reducing stable emulsions
DE102014201756A1 (de) * 2014-01-31 2015-08-06 Evonik Degussa Gmbh Reinigung chlorverschmutzter Organophosphorverbindungen
WO2015200630A1 (en) 2014-06-27 2015-12-30 Invista North America S.A R.L. Integrated process for nitrile manufacture with enhanced liquid-liquid extraction
WO2015200597A1 (en) 2014-06-27 2015-12-30 Invista North America S.A R.L. Enhanced extraction of impurities from mixture comprising nitriles

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JPH0977713A (ja) * 1995-09-19 1997-03-25 Mitsubishi Chem Corp アルデヒド類の製造方法
JP2003509487A (ja) * 1999-09-20 2003-03-11 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 多座ホスファイト配位子、前記配位子を含有する触媒組成物および前記触媒組成物を用いた触媒方法

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US5059710A (en) 1988-08-05 1991-10-22 Union Carbide Chemicals And Plastics Technology Corporation Ionic phosphites and their use in homogeneous transition metal catalyzed processes
US5113022A (en) 1988-08-05 1992-05-12 Union Carbide Chemicals & Plastics Technology Corporation Ionic phosphites used in homogeneous transition metal catalyzed processes
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US5360938A (en) 1991-08-21 1994-11-01 Union Carbide Chemicals & Plastics Technology Corporation Asymmetric syntheses
DE4204808A1 (de) 1992-02-18 1993-08-19 Basf Ag Verfahren zur herstellung von (omega)-formylalkancarbonsaeureestern
BE1007944A3 (nl) 1993-12-30 1995-11-21 Dsm Nv Werkwijze voor de bereiding van 5-formylvaleriaanzuur en -ester.
TW343195B (en) * 1996-03-15 1998-10-21 Dsm Nv Process to prepare a terminal aldehyde
US5874641A (en) * 1996-03-15 1999-02-23 Dsm N.V. Process to prepare a terminal aldehyde
EP0839787A1 (en) * 1996-11-04 1998-05-06 Dsm N.V. Process for the preparation of an aldehyde
DE19717359B4 (de) 1996-04-30 2014-10-30 Mitsubishi Chemical Corp. Bisphosphitverbindungen und Verfahren zu deren Herstellung
ZA986369B (en) * 1997-07-29 2000-01-17 Du Pont Hydrocyanation of diolefins and isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles.
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Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
JPH0977713A (ja) * 1995-09-19 1997-03-25 Mitsubishi Chem Corp アルデヒド類の製造方法
JP2003509487A (ja) * 1999-09-20 2003-03-11 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 多座ホスファイト配位子、前記配位子を含有する触媒組成物および前記触媒組成物を用いた触媒方法

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004513950A (ja) * 2000-11-17 2004-05-13 ザ　ペン　ステイト　リサーチ　ファンデーション オルト置換キラルホスフィンおよびホスフィナイトならびに非対称触媒反応でのその使用
JP2004149460A (ja) * 2002-10-30 2004-05-27 Mitsubishi Chemicals Corp 固体担持有機リン化合物、遷移金属錯体、及び触媒反応方法
JP2016511282A (ja) * 2013-03-14 2016-04-14 ユニバーシティ オブ マカオＵｎｉｖｅｒｓｉｔｙ Ｏｆ Ｍａｃａｕ ヤクチ（益智（ａｌｐｉｎｉａｅｏｘｙｐｈｙｌｌａｅｆｒｕｃｔｕｓ））およびその全合成から単離される新規な抗神経変性天然化合物
US10011555B2 (en) 2013-03-14 2018-07-03 University Of Macau Methods of treating Parkinson's disease

Also Published As

Publication number Publication date
PL202488B1 (pl) 2009-06-30
CA2380626C (en) 2009-12-15
TW581769B (en) 2004-04-01
BR0014572A (pt) 2002-06-18
PL354967A1 (en) 2004-03-22
EP1216252A1 (en) 2002-06-26
DE60006561T2 (de) 2004-09-16
CN1145633C (zh) 2004-04-14
KR100644303B1 (ko) 2006-11-10
US6307107B1 (en) 2001-10-23
WO2001021627A1 (en) 2001-03-29
KR20020032600A (ko) 2002-05-03
EP1216252B1 (en) 2003-11-12
US20020013503A1 (en) 2002-01-31
MXPA02002988A (es) 2002-10-23
DE60006561D1 (de) 2003-12-18
CA2380626A1 (en) 2001-03-29
SK3932002A3 (en) 2002-07-02
AU7378200A (en) 2001-04-24
CZ2002955A3 (cs) 2002-06-12
CN1374965A (zh) 2002-10-16
US6399534B2 (en) 2002-06-04

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