KR920010519B1 - 디유기아인산염 리간드의 제조방법 - Google Patents

디유기아인산염 리간드의 제조방법 Download PDF

Info

Publication number
KR920010519B1
KR920010519B1 KR1019850700257A KR850700257A KR920010519B1 KR 920010519 B1 KR920010519 B1 KR 920010519B1 KR 1019850700257 A KR1019850700257 A KR 1019850700257A KR 850700257 A KR850700257 A KR 850700257A KR 920010519 B1 KR920010519 B1 KR 920010519B1
Authority
KR
South Korea
Prior art keywords
group
rhodium
ligand
reaction
hydroformylation
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
Application number
KR1019850700257A
Other languages
English (en)
Korean (ko)
Other versions
KR850700240A (ko
Inventor
빌리그 어네스트
조오지 아바트조글로우 안토니
로버트 브리안트 데이비드
오이젠 머레이 렉스
미카엘 마허 존
Original Assignee
유니온 카바이드 코포레이션
에드워드 지. 그라이어
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 유니온 카바이드 코포레이션, 에드워드 지. 그라이어 filed Critical 유니온 카바이드 코포레이션
Priority to KR1019910701996A priority Critical patent/KR920003119B1/ko
Publication of KR850700240A publication Critical patent/KR850700240A/ko
Application granted granted Critical
Publication of KR920010519B1 publication Critical patent/KR920010519B1/ko
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0073—Rhodium compounds
    • C07F15/008—Rhodium compounds without a metal-carbon linkage
    • 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
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
    • 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
    • C07F9/65744—Esters of oxyacids of phosphorus condensed with carbocyclic or heterocyclic rings or ring systems
    • 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
    • C07F9/6578—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 sulfur atoms with or without oxygen atoms, as ring hetero atoms
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Materials For Medical Uses (AREA)
  • Steroid Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
KR1019850700257A 1984-02-17 1985-02-15 디유기아인산염 리간드의 제조방법 Expired KR920010519B1 (ko)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1019910701996A KR920003119B1 (ko) 1984-02-17 1985-02-15 카보닐화 방법, 로듐 착화합물 촉매 및 촉매 전구체 조성물

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US58135284A 1984-02-17 1984-02-17
US581352 1984-02-17
US685025 1984-12-28
US06/685,025 US4599206A (en) 1984-02-17 1984-12-28 Transition metal complex catalyzed reactions
PCT/US1985/000231 WO1985003702A1 (en) 1984-02-17 1985-02-15 Transition metal complex catalyzed reactions

Related Child Applications (1)

Application Number Title Priority Date Filing Date
KR1019910701996A Division KR920003119B1 (ko) 1984-02-17 1985-02-15 카보닐화 방법, 로듐 착화합물 촉매 및 촉매 전구체 조성물

Publications (2)

Publication Number Publication Date
KR850700240A KR850700240A (ko) 1985-12-26
KR920010519B1 true KR920010519B1 (ko) 1992-12-04

Family

ID=27078299

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019850700257A Expired KR920010519B1 (ko) 1984-02-17 1985-02-15 디유기아인산염 리간드의 제조방법

Country Status (21)

Country Link
US (1) US4599206A (https=)
EP (1) EP0155508B1 (https=)
JP (1) JPH0645633B2 (https=)
KR (1) KR920010519B1 (https=)
AT (1) ATE83230T1 (https=)
AU (2) AU579144B2 (https=)
BR (1) BR8505278A (https=)
CA (1) CA1262915A1 (https=)
CS (1) CS271311B2 (https=)
DE (1) DE3586878T2 (https=)
DK (1) DK473485A (https=)
ES (3) ES8609185A1 (https=)
FI (1) FI88709C (https=)
HU (1) HU202176B (https=)
MX (1) MX164254B (https=)
NO (1) NO165915C (https=)
PL (2) PL251973A1 (https=)
RO (1) RO92321B (https=)
SG (1) SG32193G (https=)
WO (1) WO1985003702A1 (https=)
YU (1) YU44255B (https=)

Families Citing this family (161)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2710040A (en) * 1953-10-29 1955-06-07 Joseph L Boyd Bending machine
US4737588A (en) * 1984-12-28 1988-04-12 Union Carbide Corporation Transition metal complex catalyzed reactions
US4668651A (en) * 1985-09-05 1987-05-26 Union Carbide Corporation Transition metal complex catalyzed processes
US4748261A (en) 1985-09-05 1988-05-31 Union Carbide Corporation Bis-phosphite compounds
US4885401A (en) * 1985-09-05 1989-12-05 Union Carbide Corporation Bis-phosphite compounds
US4774361A (en) * 1986-05-20 1988-09-27 Union Carbide Corporation Transition metal complex catalyzed reactions
US4835299A (en) * 1987-03-31 1989-05-30 Union Carbide Corporation Process for purifying tertiary organophosphites
US5113022A (en) * 1988-08-05 1992-05-12 Union Carbide Chemicals & Plastics Technology Corporation Ionic phosphites used in homogeneous transition metal catalyzed processes
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
US5001274A (en) * 1989-06-23 1991-03-19 Union Carbide Chemicals And Plastics Company Inc. Hydroformylation process
US5210318A (en) * 1990-05-04 1993-05-11 Union Carbide Chemicals & Plastics Technology Corporation Catalysts and processes useful in producing 1,3-diols and/or 3-hydroxyldehydes
DE4026406A1 (de) * 1990-08-21 1992-02-27 Basf Ag Rhodiumhydroformylierungskatalysatoren mit bis-phosphit-liganden
JPH06503808A (ja) * 1990-08-31 1994-04-28 ザ　ガヴァナーズ　オヴ　ザ　ユニヴァーシティ　オヴ　アルバータ 新規の遷移金属触媒先駆物質を用いるメタノールのカルボニル化
US5087763A (en) * 1990-11-09 1992-02-11 Union Carbide Chemicals & Plastics Technology Corporation Hydroformylation process
JP2946790B2 (ja) * 1991-03-14 1999-09-06 三菱化学株式会社 アルデヒド類の製造法
US5177019A (en) * 1991-05-20 1993-01-05 Eastman Kodak Company Method of quantitative analysis of organophosphorus compounds
TW213465B (https=) * 1991-06-11 1993-09-21 Mitsubishi Chemicals Co Ltd
US5360938A (en) * 1991-08-21 1994-11-01 Union Carbide Chemicals & Plastics Technology Corporation Asymmetric syntheses
US5292785A (en) * 1992-05-05 1994-03-08 Ciba-Geigy Corporation Bis-phosphite stabilized compositions
US5312996A (en) * 1992-06-29 1994-05-17 Union Carbide Chemicals & Plastics Technology Corporation Hydroformylation process for producing 1,6-hexanedials
US5310889A (en) * 1992-07-22 1994-05-10 Ciba-Geigy Corporation Carbohydrate substituted dibenzo(d,f)(1,3,2)dioxaphosphepin stabilizers
US5310890A (en) * 1992-07-22 1994-05-10 Ciba-Geigy Corporation Carbohydrate substituted dibenzoi(d,g)(1,3,2)dioxaphosphocin stabilizers
US5364950A (en) * 1992-09-29 1994-11-15 Union Carbide Chimicals & Plastics Technology Corporation Process for stabilizing phosphite ligands in hydroformylation reaction mixtures
DE4242723A1 (de) * 1992-12-17 1994-06-23 Hoechst Ag Verfahren zur Herstellung von Aldehyden
DE69417961T2 (de) * 1993-07-22 1999-12-02 General Electric Co., Schenectady Neoalkyl Alkyliden-2,2'-Biphenyl und Bisnenyl Phosphit-Ester
EP0730574B1 (en) * 1993-11-23 1998-08-19 E.I. Du Pont De Nemours And Company Processes and catalyst compositions for hydrocyanation of monoolefins
EP0755302B1 (en) 1994-04-14 2000-10-04 E.I. Du Pont De Nemours And Company Bidentate phosphite and nickel catalyst compositions for hydrocyanation of monoolefins
US5512695A (en) * 1994-04-14 1996-04-30 E. I. Du Pont De Nemours And Company Bidentate phosphite and nickel catalyst compositions for hydrocyanation of monoolefins
US5543536A (en) * 1994-04-26 1996-08-06 E. I. Du Pont De Nemours And Company Monodentate phosphite and nickel catalyst composition for monoolefin hydrocyanation
SG44321A1 (en) * 1994-07-18 1997-12-19 Mitsubishi Chem Corp Method for dimerizing an olefin
US5756855A (en) * 1994-08-19 1998-05-26 Union Carbide Chemicals & Plastics Technology Corporation Stabilization of phosphite ligands in hydroformylation process
US5512696A (en) * 1995-07-21 1996-04-30 E. I. Du Pont De Nemours And Company Hydrocyanation process and multidentate phosphite and nickel catalyst composition therefor
TW315370B (https=) * 1994-10-07 1997-09-11 Du Pont
US5672766A (en) * 1994-12-12 1997-09-30 Mitsubishi Chemical Corporation Method for producing aldehydes
US5516965A (en) * 1995-01-18 1996-05-14 Exxon Research And Engineering Company Unsaturates recovery and recycle process
US5675041A (en) * 1995-01-18 1997-10-07 Exxon Research & Engineering Company Direct hydroformylation of a multi-component synthesis gas containing carbon monoxide, hydrogen, ethylene, and acetylene
US5520722A (en) * 1995-01-18 1996-05-28 Exxon Research And Engineering Company Multiunsaturates removal process
IN187044B (https=) * 1995-01-27 2002-01-05 Du Pont
US5821378A (en) * 1995-01-27 1998-10-13 E. I. Du Pont De Nemours And Company Hydrocyanation of diolefins and isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles
JP3291421B2 (ja) 1995-08-18 2002-06-10 ユニオン・カーバイド・ケミカルズ・アンド・プラスティックス・テクノロジー・コーポレイション ヒドロホルミル化方法におけるホスフィットリガンドの安定化
US5763677A (en) * 1995-12-06 1998-06-09 Union Carbide Chemicals & Plastics Technology Corporation Hydroformylation processes
US5654455A (en) * 1995-12-21 1997-08-05 Ciba-Geigy Corporation Tris-phosphite ligands and their use in transitioin metal catalyzed processes
US5892119A (en) * 1996-11-26 1999-04-06 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
US5962744A (en) * 1998-03-27 1999-10-05 The Research Foundation Of State University Of New York Process for hydrocarbonylations in supercritical carbon dioxide
JP3847466B2 (ja) * 1998-09-01 2006-11-22 三菱化学株式会社 オレフィンのヒドロホルミル化反応方法
JP3921853B2 (ja) * 1998-12-10 2007-05-30 三菱化学株式会社 アルデヒド類及びアルコール類の製造方法
CN1163463C (zh) 1998-12-10 2004-08-25 三菱化学株式会社 醛的制备方法
JP3928315B2 (ja) * 1998-12-14 2007-06-13 三菱化学株式会社 アルデヒドの製造方法
US6610891B1 (en) 1999-12-03 2003-08-26 Mitsubishi Chemical Corporation Method of producing aldehydes
WO2001051441A1 (en) * 2000-01-12 2001-07-19 Eastman Chemical Company Hydroformylation method for making aldehydes from sterically hindered olefins
JP3864668B2 (ja) * 2000-05-01 2007-01-10 三菱化学株式会社 アルデヒド類の製造方法
DE10027505A1 (de) * 2000-06-06 2001-12-13 Studiengesellschaft Kohle Mbh Chirale Monophosphite als Liganden für die asymmetrische Übergangsmetall-katalysierte Hydrierung
GB0021715D0 (en) * 2000-09-05 2000-10-18 Ici Plc Recovery of metals
DE10058383A1 (de) 2000-11-24 2002-05-29 Oxeno Olefinchemie Gmbh Neue Phosphininverbindungen und deren Metallkomplexe
DE10140086A1 (de) 2001-08-16 2003-02-27 Oxeno Olefinchemie Gmbh Neue Phosphitverbindungen und neue Phosphitmetallkomplexe
DE10148551A1 (de) 2001-10-01 2003-04-10 Bayer Ag Chirale Monophosphorverbindungen
DE10149349A1 (de) * 2001-10-06 2003-04-17 Oxeno Olefinchemie Gmbh Verfahren zur Herstellung von 6-Methylheptan-2-on und dessen Verwendung
DE60304034T2 (de) * 2002-03-11 2006-10-12 Union Carbide Chemicals & Plastics Technology Corp., Danbury Bisphosphit-ligande für carbonylierungsverfahren
DE10220801A1 (de) 2002-05-10 2003-11-20 Oxeno Olefinchemie Gmbh Verfahren zur Rhodium-katalysierten Hydroformylierung von Olefinen unter Reduzierung der Rhodiumverluste
BR0313866A (pt) 2002-08-31 2005-07-05 Oxeno Olefinchemie Gmbh Processo para a hidroformilação de compostos olefinicamente insaturados, especialmente olefinas na presença de ésteres de ácido carbÈnico cìclicos
JP2006503086A (ja) * 2002-10-15 2006-01-26 ユニオン・カーバイド・ケミカルズ・アンド・プラスティックス・テクノロジー・コーポレイション ビス−キレート化配位子及びカルボニル化方法におけるその使用
KR20060096433A (ko) * 2003-10-21 2006-09-11 바스프 악티엔게젤샤프트 알데히드의 연속식 제조 방법
DE10349343A1 (de) * 2003-10-23 2005-06-02 Basf Ag Stabilisierung von Hydroformylierungskatalysatoren auf Basis von Phosphoramiditliganden
DE102004013514A1 (de) * 2004-03-19 2005-10-06 Oxeno Olefinchemie Gmbh Verfahren zur Hydroformylierung von Olefinen in Anwesenheit von neuen phosphororganischen Verbindungen
US7291748B2 (en) 2005-07-28 2007-11-06 Basf Corporation C10/C7 ester mixtures based on 2-propylheptanol
DE102005042464A1 (de) 2005-09-07 2007-03-08 Oxeno Olefinchemie Gmbh Carbonylierungsverfahren unter Zusatz von sterisch gehinderten sekundären Aminen
DE102006034442A1 (de) * 2006-07-26 2008-01-31 Oxeno Olefinchemie Gmbh Katalysatorvorstufe für einen Rh-Komplexkatalysator
JP5266247B2 (ja) 2006-12-07 2013-08-21 ビーエーエスエフ ソシエタス・ヨーロピア 殺菌性トリアゾールおよびアルコキシル化アルコールを含む組成物およびキットならびにそれらの使用
DE102006058682A1 (de) 2006-12-13 2008-06-19 Evonik Oxeno Gmbh Bisphosphitliganden für die übergangsmetallkatalysierte Hydroformylierung
US7586010B2 (en) * 2006-12-21 2009-09-08 Eastman Chemical Company Phosphonite-containing catalysts for hydroformylation processes
CN101657407B (zh) * 2007-03-20 2014-02-12 陶氏技术投资有限公司 改善对产物同分异构体的控制的加氢甲酰基化方法
JP5298119B2 (ja) * 2007-04-09 2013-09-25 エルジー・ケム・リミテッド ホスファイト配位子を含む触媒組成物およびこれを用いたヒドロホルミル化方法
DE102007023514A1 (de) 2007-05-18 2008-11-20 Evonik Oxeno Gmbh Stabile Katalysatorvorstufe von Rh-Komplexkatalysatoren
WO2009035838A2 (en) 2007-09-07 2009-03-19 Dow Global Technologies Inc. Hydrogenation of aliphatic dialdehydes to aliphatic diols
US7872156B2 (en) * 2007-12-26 2011-01-18 Eastman Chemical Company Fluorophosphite containing catalysts for hydroformylation processes
US7872157B2 (en) * 2007-12-26 2011-01-18 Eastman Chemical Company Phosphonite containing catalysts for hydroformylation processes
US7708912B2 (en) * 2008-06-16 2010-05-04 Polytronics Technology Corporation Variable impedance composition
EP2257560B1 (en) * 2008-03-28 2013-07-17 Union Carbide Chemicals & Plastics Technology Llc (Formerly Union Carbide Chemicals & Plastics Technology Corporation) Slurry process for phosphoromonochloridite synthesis
MX2010014570A (es) 2008-07-03 2011-08-15 Dow Technology Investments Llc Proceso para controlar pesados en una corriente de catalizador de reciclado.
CN102123978B (zh) * 2008-08-19 2014-03-19 陶氏技术投资有限公司 用于改进对产物异构体的控制的使用对称的二亚磷酸酯配体的加氢甲酰化方法
WO2010042313A1 (en) * 2008-10-08 2010-04-15 Dow Technology Investments Llc Slurry process for synthesis of bisphosphites
US8921486B2 (en) 2008-11-14 2014-12-30 University Of Kansas Polymer-supported transition metal catalyst complexes and methods of use
DE102009001225A1 (de) 2009-02-27 2010-09-02 Evonik Oxeno Gmbh Verfahren zur Anreicherung eines Homogenkatalysators aus einem Prozessstrom
US7928267B1 (en) * 2009-06-22 2011-04-19 Eastman Chemical Company Phosphite containing catalysts for hydroformylation processes
DE102009029050A1 (de) 2009-08-31 2011-03-03 Evonik Oxeno Gmbh Organophosphorverbindungen basierend auf Tetraphenol(TP)-substituierten Strukturen
EP2488539B2 (en) 2009-10-16 2023-12-20 Dow Technology Investments LLC Gas phase hydroformylation process
KR20120099247A (ko) 2009-11-05 2012-09-07 바스프 에스이 2-프로필헵탄올 기재의 에스테르를 포함하는 접착제 및 실란트
EP2516371B2 (en) 2009-12-22 2022-08-17 Dow Technology Investments LLC Controlling the normal:iso aldehyde ratio in a mixed ligand hydroformylation process by controlling the olefin partial pressure
CA2784943C (en) 2009-12-22 2016-09-06 Dow Technology Investments Llc Controlling the normal:iso aldehyde ratio in a mixed ligand hydroformylation process by controlling the syngas partial pressure
CN102741210B (zh) 2009-12-22 2016-02-24 陶氏技术投资有限责任公司 控制混合配体加氢甲酰化工艺中的正构∶异构醛比率
JP5652052B2 (ja) * 2010-08-24 2015-01-14 三菱化学株式会社 アルデヒドの製造方法
CN103153462B (zh) 2010-10-05 2016-06-01 陶氏技术投资有限责任公司 加氢甲酰基化方法
SA112330271B1 (ar) 2011-04-18 2015-02-09 داو تكنولوجى انفستمنتس ال ال سى تخفيف التلوث في عمليات هيدروفورملة عن طريق إضافة الماء
CN102826974B (zh) * 2011-06-17 2015-11-25 中国石油化工股份有限公司 一种丙烯氢甲酰化反应制备丁醛的方法
JP6068482B2 (ja) 2011-09-30 2017-01-25 ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー 精製プロセス
DE102011085883A1 (de) 2011-11-08 2013-05-08 Evonik Oxeno Gmbh Neue Organophosphorverbindungen auf Basis von Anthracentriol
CA2858351C (en) 2011-12-20 2016-11-22 Dow Technology Investments Llc A hydroformylation process
RU2634719C2 (ru) 2012-06-04 2017-11-03 Дау Текнолоджи Инвестментс Ллс Способ гидроформилирования
DE102012105878A1 (de) 2012-07-02 2014-01-02 Oxea Gmbh Verfahren zur Herstellung von Isopentanderivaten
US9539566B2 (en) 2012-08-29 2017-01-10 Dow Technology Investments Llc Catalyst preparation process
RU2639156C2 (ru) 2012-09-25 2017-12-20 Дау Текнолоджи Инвестментс Ллс Способ стабилизации фосфитного лиганда против деградации
DE102013219506A1 (de) 2012-10-12 2014-04-17 Evonik Degussa Gmbh Unsymmetrisches Bisphosphit
EP2906573B1 (de) 2012-10-12 2016-11-23 Evonik Degussa GmbH Gemisch von bisphosphiten und dessen verwendung als katalysatorgemisch in der hydroformylierung
DE102013219510A1 (de) 2012-10-12 2014-04-17 Evonik Degussa Gmbh Gemisch von Bisphosphiten und dessen Verwendung als Katalysatorgemisch in der Hydroformylierung
DE102013219512A1 (de) 2012-10-12 2014-04-17 Evonik Degussa Gmbh Gemisch aus verschiedenen unsymmetrischen Bisphosphiten und dessen Verwendung als Katalysatorgemisch in der Hydroformylierung
DE102013219508A1 (de) 2012-10-12 2014-04-17 Evonik Degussa Gmbh Gemische konstitutionsisomerer Bisphosphite
EP2928855A1 (en) 2012-12-06 2015-10-14 Dow Technology Investments LLC Hydroformylation process
RU2527455C1 (ru) * 2013-03-28 2014-08-27 Открытое акционерное общество "Нефтяная компания "Роснефть" Способ получения альдегидов
RU2536048C2 (ru) * 2013-03-28 2014-12-20 Открытое акционерное общество "Нефтяная компания "Роснефть" Способ региоселективного получения н-пентаналя
CN104248860A (zh) 2013-06-27 2014-12-31 陶氏技术投资有限责任公司 热管理方法
DE102013020323B3 (de) 2013-12-05 2015-01-08 Oxea Gmbh Verfahren zur Herstellung von isomeren Hexansäuren aus den bei der Herstellung von Pentanalen anfallenden Nebenströmen
DE102013020320B4 (de) 2013-12-05 2019-04-04 Oxea Gmbh Verfahren zur Herstellung von 2-Methylbuttersäure mit einem vermindertem Gehalt an 3-Methylbuttersäure aus den bei der Herstellung von Pentansäuren anfallenden Nebenströmen
DE102013020322B4 (de) 2013-12-05 2019-04-18 Oxea Gmbh Verfahren zur Gewinnung von 2-Methylbutanal aus den bei der Herstellung von Gemischen isomerer a,ß-ungesättigter Decenale anfallenden Nebenströmen
CN104725170B (zh) 2013-12-19 2019-08-23 陶氏技术投资有限责任公司 加氢甲酰化方法
JP2016540780A (ja) 2013-12-19 2016-12-28 ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー ヒドロホルミル化プロセス
US10131608B2 (en) 2014-03-31 2018-11-20 Dow Technology Investments Llc Hydroformylation process
US10501486B2 (en) 2014-05-14 2019-12-10 Dow Technology Investments Llc Stabilized organophosphorous compounds
DE102014209534A1 (de) 2014-05-20 2015-11-26 Evonik Degussa Gmbh Neue Monophosphitliganden mit einer Carbonat-Gruppe
DE102014209532A1 (de) 2014-05-20 2015-11-26 Evonik Degussa Gmbh Neue Monophosphitliganden mit einer tert-Butyloxycarbonyl-Gruppe
DE202014007140U1 (de) 2014-09-08 2014-10-22 Basf Se Öl-basierte Bohrflüssigkeiten mit Copolymeren aus Styrol, (Meth)acrylaten von C10-Alkoholgemischen und (Meth)acrylsäure
DE202014007136U1 (de) 2014-09-08 2014-10-16 Basf Se Härtbare Zusammensetzung, hergestellt mit einem aus (Meth)acrylaten von C10-Alkoholgemischen aufgebauten Copolymer
EP3031815B1 (de) * 2014-12-04 2019-02-20 Evonik Degussa GmbH Terphenyl-2-oxy-phosphite als liganden in hydroformylierungs-katalysatoren
ES2670039T3 (es) * 2014-12-04 2018-05-29 Evonik Degussa Gmbh Monofosfitos que presentan un componente biarilo asimétrico
MY184826A (en) 2014-12-04 2021-04-24 Dow Technology Investments Llc Hydroformylation process
EP3029052B1 (de) 2014-12-04 2018-02-28 Evonik Degussa GmbH 9-Anthrol-monophosphit Ester als Liganden für Hydroformylierungs-Katalysatoren
DE102015207870A1 (de) 2015-04-29 2016-11-03 Evonik Degussa Gmbh Neue Monophosphitverbindungen mit einer Sulfonatgruppe
DE102015207860A1 (de) 2015-04-29 2016-11-03 Evonik Degussa Gmbh Neue Monophosphitverbindungen mit einer Methylgruppe
DE102015207864A1 (de) 2015-04-29 2016-11-03 Evonik Degussa Gmbh Neue Monophosphitverbindungen mit einer Ethergruppe
DE102015207866A1 (de) 2015-04-29 2016-11-03 Evonik Degussa Gmbh Neue Monophosphitverbindungen mit einer Estergruppe
EP3147290A1 (de) * 2015-09-22 2017-03-29 Evonik Degussa GmbH Monophosphite, die ein binol-derivat aufweisen
EP3147289B1 (de) 2015-09-22 2017-11-22 Evonik Degussa GmbH Monophosphite, die ein teilhydriertes binol-derivat aufweisen
EP3147288A1 (de) 2015-09-22 2017-03-29 Evonik Degussa GmbH Monophosphite, die ein cyclododecanol aufweisen
TWI709566B (zh) * 2015-09-30 2020-11-11 美商陶氏科技投資公司 用於製造有機磷化合物的方法
TWI709568B (zh) 2015-09-30 2020-11-11 美商陶氏科技投資公司 用於製造有機磷化合物的方法
KR102743230B1 (ko) 2015-11-10 2024-12-17 다우 테크놀로지 인베스트먼츠 엘엘씨. 알데하이드를 생산하는 방법
MX2018009690A (es) 2016-02-11 2018-09-11 Dow Technology Investments Llc Procesos para convertir olefinas en alcoholes, eteres o combinaciones de los mismos.
DE102016205883A1 (de) 2016-04-08 2017-10-12 Evonik Degussa Gmbh Pinakolester von Antracen-9-yloxy substituierten Dioxaphospholanen
EP3296303A1 (de) * 2016-09-16 2018-03-21 Evonik Degussa GmbH Monophosphite mit methylenverbrücktem diphenol und diphenylphenylrest
TWI788364B (zh) 2017-06-23 2023-01-01 美商陶氏科技投資有限公司 氫甲醯化反應製程
CN111212826B (zh) 2017-10-25 2023-05-23 陶氏技术投资有限责任公司 减少在加氢甲酰化过程中形成的包含醛化合物的溶液中重物质形成的方法
JP7269238B2 (ja) 2017-11-13 2023-05-08 ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー ヒドロホルミル化プロセスからロジウムを回収するためのプロセス
TWI793216B (zh) 2017-12-07 2023-02-21 美商陶氏科技投資公司 氫甲醯化方法
CA3120660A1 (en) 2018-11-29 2020-06-04 Dow Technology Investments Llc Hydroformylation process
US10538472B1 (en) 2019-02-14 2020-01-21 Dairen Chemical Corporation Extraction process for high-boiling aldehyde product separation and catalyst recovery
US20220143590A1 (en) 2019-06-27 2022-05-12 Dow Technology Investments Llc Process to prepare solution from hydroformylation process for precious metal recovery
KR102686720B1 (ko) * 2019-07-04 2024-07-18 주식회사 엘지화학 하이드로포밀화 반응용 촉매 조성물 및 이를 이용한 알데히드의 제조방법
KR102768893B1 (ko) * 2019-09-27 2025-02-14 주식회사 엘지화학 인계 리간드를 포함하는 하이드로포밀화 반응용 촉매 조성물 및 이를 이용한 하이드로포밀화 방법
TWI874467B (zh) 2019-11-05 2025-03-01 美商陶氏科技投資有限公司 用於自ｃ６或更高碳數烯烴氫甲醯化製程之催化劑淨化流回收銠之方法
US11976017B2 (en) 2019-12-19 2024-05-07 Dow Technology Investments Llc Processes for preparing isoprene and mono-olefins comprising at least six carbon atoms
CN116635362A (zh) 2020-12-14 2023-08-22 陶氏技术投资有限责任公司 改进加氢甲酰化方法中的催化金属可计量性的方法
US20230406802A1 (en) 2020-12-22 2023-12-21 Dow Technology Investments Llc Hydroformylation reaction processes
US20250137091A1 (en) 2021-11-11 2025-05-01 Dow Technology Investments Llc Processes for recovering rhodium from hydroformylation processes
JPWO2023095907A1 (https=) 2021-11-29 2023-06-01
WO2023112762A1 (ja) 2021-12-14 2023-06-22 三菱ケミカル株式会社 アルデヒドの製造方法及びアルコールの製造方法、並びに触媒組成物
CN118317834A (zh) 2021-12-16 2024-07-09 陶氏技术投资有限责任公司 化合物、包含此类化合物的过渡金属络合物加氢甲酰化催化剂前体组合物和加氢甲酰化方法
PL4448171T3 (pl) 2021-12-16 2025-10-20 Dow Technology Investments Llc Kompozycje prekursora katalitycznego do hydroformylowania kompleksu metalu przejściowego zawierające takie związki i procesy hydroformylowania
WO2024228768A1 (en) 2023-05-04 2024-11-07 Dow Technology Investments Llc Hydroformylation process
GB202307175D0 (en) 2023-05-15 2023-06-28 Johnson Matthey Davy Technologies Ltd Process for hydrogenating a substrate
KR20260045840A (ko) 2023-08-03 2026-04-03 다우 테크놀로지 인베스트먼츠 엘엘씨. 하이드로포르밀화 공정
CN121532373A (zh) 2023-08-03 2026-02-13 陶氏技术投资有限责任公司 用于改善基于铑/亚磷酸酯的均相加氢甲酰化催化剂活性的方法
GB202404300D0 (en) 2024-03-26 2024-05-08 Johnson Matthey Davy Technologies Ltd Process for the production of 2-alkylalkanol

Family Cites Families (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3213155A (en) * 1961-05-19 1965-10-19 Exxon Research Engineering Co Monoolefin isomerization process
US3476699A (en) * 1961-12-18 1969-11-04 Argus Chem Polyvinyl chloride and olefin polymer compositions having improved resistance to deterioration comprising an organic phosphite ester having at least one aromatic polycarbocyclic group
NL297350A (https=) * 1962-08-31
US3297631A (en) * 1965-10-24 1967-01-10 Exxon Research Engineering Co Novel phenolic phosphorus stabilizers for polyolefins
US3437720A (en) * 1966-08-03 1969-04-08 Weston Chemical Corp Carboxylated hydroxy phosphites
US3527809A (en) * 1967-08-03 1970-09-08 Union Carbide Corp Hydroformylation process
US3491024A (en) * 1967-09-15 1970-01-20 Hooker Chemical Corp 2,6-disubstituted primary aryl phosphites,their salts and phosphorodihalidites and processes for the manufacture thereof
US3655832A (en) * 1969-02-18 1972-04-11 Argus Chem Polycarbocyclic phenolic phosphites
JPS4510729Y1 (https=) * 1969-06-02 1970-05-15
JPS4840326B1 (https=) * 1970-12-15 1973-11-30
US4148830A (en) * 1975-03-07 1979-04-10 Union Carbide Corporation Hydroformylation of olefins
US4247486A (en) * 1977-03-11 1981-01-27 Union Carbide Corporation Cyclic hydroformylation process
US4094855A (en) * 1976-07-30 1978-06-13 Ciba-Geigy Corporation Hindered phenyl phosphites
US4148430A (en) 1977-05-25 1979-04-10 Innovative Business Forms, Inc. Business form
CA1104587A (en) * 1977-06-21 1981-07-07 Peter J. Davidson Catalytic hydroformylation of internal olefins
US4351759A (en) * 1978-01-03 1982-09-28 Ciba-Geigy Corporation Alkylated 2,2'-biphenylene phosphites and stabilized compositions
US4288391A (en) * 1978-01-03 1981-09-08 Ciba-Geigy Corporation Alkylated 2,2'-biphenylene phosphites
US4196117A (en) * 1978-01-03 1980-04-01 Ciba-Geigy Corporation Alkylated 1,1'-biphenyl-2,2'-diyl phosphites and stabilized compositions
DE2837027A1 (de) * 1978-08-24 1980-03-06 Bayer Ag Neue phosphorigsaeureester und ihre verwendung zur stabilisierung von polyamiden
US4298541A (en) * 1979-02-12 1981-11-03 Exxon Research & Engineering Co. Trihydrocarbyl silyl-substituted alkyl diaryl phosphine transition metal complexes and their use as homogeneous catalysts
DE2965157D1 (en) * 1979-03-21 1983-05-11 Davy Mckee London Process for the production of aldehydes by hydroformylation of alkenes
DE2965158D1 (en) * 1979-03-21 1983-05-11 Davy Mckee London Hydroformylation process
US4283562A (en) * 1979-10-26 1981-08-11 Union Carbide Corporation Hydroformylation process using stable rhodium catalyst
JPS5699246A (en) * 1980-01-10 1981-08-10 Adeka Argus Chem Co Ltd Stabilized synthetic resin composition
US4330678A (en) * 1980-02-04 1982-05-18 Shell Oil Company Process for the hydroformylation of olefins
GB2068377B (en) * 1980-02-04 1983-09-28 Shell Int Research Process for the hydroformylation of olefins
US4374219A (en) * 1980-11-24 1983-02-15 Ciba-Geigy Corporation Alkanolamine ester of 1,1-biphenyl-2,2-diyl-and alkylidene-1,1-biphenyl-2,2-diyl-cyclic phosphites
US4318845A (en) * 1980-11-24 1982-03-09 Ciba-Geigy Corporation Alkanolamine esters of 1,1'-biphenyl-2,2'-diyl-and alkylidene-1,1'-biphenyl-2,2'-diyl-cyclic phosphites
EP0054986A1 (en) * 1980-12-22 1982-06-30 Shell Internationale Researchmaatschappij B.V. A process for the hydroformylation of olefins
CA1186342A (en) * 1981-03-12 1985-04-30 Anthony G. Abatjoglou Process for removing hydroperoxides and aldehydes from allyl-alkyl ether
US4388476A (en) * 1981-05-01 1983-06-14 Eastman Kodak Company Hydroformylation process with rhodium catalyst and oxygen stabilization thereof
US4400548A (en) * 1981-08-17 1983-08-23 Union Carbide Corporation Hydroformylation process using bisphosphine monooxide ligands
ATE16475T1 (de) * 1982-06-11 1985-11-15 Davy Mckee London Hydroformylierungsverfahren.
ATE28183T1 (de) * 1982-06-11 1987-07-15 Davy Mckee London Hydroformylierungsverfahren.
DE3371067D1 (en) * 1982-06-11 1987-05-27 Davy Mckee London Hydroformylation process
DE3234701A1 (de) * 1982-09-18 1984-04-05 Ruhrchemie Ag, 4200 Oberhausen Verfahren zur herstellung von aldehyden
DE3341035A1 (de) * 1983-11-12 1985-05-23 Ruhrchemie Ag, 4200 Oberhausen Verfahren zur herstellung von aldehyden
GB8334359D0 (en) * 1983-12-23 1984-02-01 Davy Mckee Ltd Process
CA1259331A (en) * 1984-03-30 1989-09-12 Gregory J. Dembowski Process for recovery of phosphorus ligand from vaporized aldehyde
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

Also Published As

Publication number Publication date
ES8609185A1 (es) 1986-09-01
YU44255B (en) 1990-04-30
PL151491B1 (en) 1990-09-28
ES540439A0 (es) 1986-09-01
CA1262915A1 (en) 1989-11-14
FI854059A0 (fi) 1985-10-17
FI854059L (fi) 1985-10-17
CA1264055C (https=) 1989-12-27
NO165915B (no) 1991-01-21
RO92321B (ro) 1987-09-01
CS109185A2 (en) 1990-02-12
RO92321A (ro) 1987-08-31
MX164254B (es) 1992-07-27
WO1985003702A1 (en) 1985-08-29
NO854113L (no) 1985-10-16
NO165915C (no) 1991-05-02
EP0155508A1 (en) 1985-09-25
ES8706480A1 (es) 1987-07-01
ATE83230T1 (de) 1992-12-15
HUT41724A (en) 1987-05-28
AU579144B2 (en) 1988-11-17
DE3586878D1 (de) 1993-01-21
US4599206A (en) 1986-07-08
AU617362B2 (en) 1991-11-28
DK473485D0 (da) 1985-10-16
HU202176B (en) 1991-02-28
PL251973A1 (en) 1986-07-29
BR8505278A (pt) 1986-02-18
DE3586878T2 (de) 1993-06-24
ES8701140A1 (es) 1986-11-16
DK473485A (da) 1985-12-11
SG32193G (en) 1993-05-21
ES549717A0 (es) 1986-11-16
AU2278888A (en) 1989-01-19
KR850700240A (ko) 1985-12-26
FI88709C (fi) 1993-06-28
FI88709B (fi) 1993-03-15
YU22585A (en) 1988-02-29
JPS61501268A (ja) 1986-06-26
JPH0645633B2 (ja) 1994-06-15
AU3997085A (en) 1985-09-10
EP0155508B1 (en) 1992-12-09
CS271311B2 (en) 1990-09-12
ES554326A0 (es) 1987-07-01

Similar Documents

Publication Publication Date Title
KR920010519B1 (ko) 디유기아인산염 리간드의 제조방법
US4737588A (en) Transition metal complex catalyzed reactions
US4769498A (en) Transition metal complex catalyzed processes
US4748261A (en) Bis-phosphite compounds
US4885401A (en) Bis-phosphite compounds
EP0590613B1 (en) Improved hydroformylation process
EP1485392B1 (en) Bisphosphite ligands for carbonylation processes
US4789753A (en) Phosphite ligands
EA001502B1 (ru) Усовершенствованные способы, катализируемые комплексом металл-лиганд
EP1008581B1 (en) Process for producing aldehyde
KR20210015839A (ko) 하이드로포밀화 공정의 제어 방법
KR920003119B1 (ko) 카보닐화 방법, 로듐 착화합물 촉매 및 촉매 전구체 조성물
JP3956559B2 (ja) アルデヒドの製造方法
NO174622B (no) Fremgangsmaate for karbonylering

Legal Events

Date Code Title Description
PA0105 International application

St.27 status event code: A-0-1-A10-A15-nap-PA0105

R17-X000 Change to representative recorded

St.27 status event code: A-3-3-R10-R17-oth-X000

PG1501 Laying open of application

St.27 status event code: A-1-1-Q10-Q12-nap-PG1501

A201 Request for examination
P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

PA0201 Request for examination

St.27 status event code: A-1-2-D10-D11-exm-PA0201

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

St.27 status event code: A-1-2-D10-D21-exm-PE0902

T11-X000 Administrative time limit extension requested

St.27 status event code: U-3-3-T10-T11-oth-X000

T11-X000 Administrative time limit extension requested

St.27 status event code: U-3-3-T10-T11-oth-X000

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

St.27 status event code: A-1-2-D10-D21-exm-PE0902

T11-X000 Administrative time limit extension requested

St.27 status event code: U-3-3-T10-T11-oth-X000

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

G160 Decision to publish patent application
PG1605 Publication of application before grant of patent

St.27 status event code: A-2-2-Q10-Q13-nap-PG1605

E701 Decision to grant or registration of patent right
PE0701 Decision of registration

St.27 status event code: A-1-2-D10-D22-exm-PE0701

GRNT Written decision to grant
PR0701 Registration of establishment

St.27 status event code: A-2-4-F10-F11-exm-PR0701

PR1002 Payment of registration fee

St.27 status event code: A-2-2-U10-U12-oth-PR1002

Fee payment year number: 1

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 4

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 5

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 6

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 7

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 8

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 9

FPAY Annual fee payment

Payment date: 20010926

Year of fee payment: 10

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 10

LAPS Lapse due to unpaid annual fee
PC1903 Unpaid annual fee

St.27 status event code: A-4-4-U10-U13-oth-PC1903

Not in force date: 20021205

Payment event data comment text: Termination Category : DEFAULT_OF_REGISTRATION_FEE

PC1903 Unpaid annual fee

St.27 status event code: N-4-6-H10-H13-oth-PC1903

Ip right cessation event data comment text: Termination Category : DEFAULT_OF_REGISTRATION_FEE

Not in force date: 20021205

R18-X000 Changes to party contact information recorded

St.27 status event code: A-5-5-R10-R18-oth-X000

R18-X000 Changes to party contact information recorded

St.27 status event code: A-5-5-R10-R18-oth-X000

P22-X000 Classification modified

St.27 status event code: A-4-4-P10-P22-nap-X000

R18-X000 Changes to party contact information recorded

St.27 status event code: A-5-5-R10-R18-oth-X000