CA2833042C - Methods to store transition metal organophosphorous ligand based catalysts - Google Patents

Methods to store transition metal organophosphorous ligand based catalysts Download PDF

Info

Publication number
CA2833042C
CA2833042C CA2833042A CA2833042A CA2833042C CA 2833042 C CA2833042 C CA 2833042C CA 2833042 A CA2833042 A CA 2833042A CA 2833042 A CA2833042 A CA 2833042A CA 2833042 C CA2833042 C CA 2833042C
Authority
CA
Canada
Prior art keywords
catalyst solution
radicals
catalyst
hydroformylation
ligand
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.)
Active
Application number
CA2833042A
Other languages
English (en)
French (fr)
Other versions
CA2833042A1 (en
Inventor
Thomas C. Eisenschmid
Michael C. Becker
Donald L. Campbell, Jr.
Michael A. Brammer
Glenn A. Miller
Edward Adrian LORD
Jens Rudolph
Hans-Rudiger Reeh
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.)
BASF SE
Dow Technology Investments LLC
Original Assignee
BASF SE
Dow Technology Investments LLC
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 BASF SE, Dow Technology Investments LLC filed Critical BASF SE
Publication of CA2833042A1 publication Critical patent/CA2833042A1/en
Application granted granted Critical
Publication of CA2833042C publication Critical patent/CA2833042C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • 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
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0255—Phosphorus containing compounds
    • 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
    • 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
    • B01J31/186—Mono- or diamide 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
    • 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
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
    • 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
    • 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
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered rings
    • 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
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered rings
    • C07F9/5728—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
    • 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
    • B01J2531/80—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)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Extraction Or Liquid Replacement (AREA)
CA2833042A 2011-04-18 2012-04-13 Methods to store transition metal organophosphorous ligand based catalysts Active CA2833042C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201161476593P 2011-04-18 2011-04-18
US61/476,593 2011-04-18
PCT/US2012/033528 WO2012145241A1 (en) 2011-04-18 2012-04-13 Methods to store transition metal organophosphorous ligand based catalysts

Publications (2)

Publication Number Publication Date
CA2833042A1 CA2833042A1 (en) 2012-10-26
CA2833042C true CA2833042C (en) 2020-05-12

Family

ID=46028157

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2833042A Active CA2833042C (en) 2011-04-18 2012-04-13 Methods to store transition metal organophosphorous ligand based catalysts

Country Status (15)

Country Link
US (1) US10478812B2 (enExample)
EP (1) EP2699350B1 (enExample)
JP (1) JP5990260B2 (enExample)
KR (1) KR101879013B1 (enExample)
CN (1) CN103702758B (enExample)
BR (1) BR112013026704B1 (enExample)
CA (1) CA2833042C (enExample)
ES (1) ES2753226T3 (enExample)
MX (1) MX363707B (enExample)
MY (1) MY170248A (enExample)
RU (1) RU2598386C2 (enExample)
SA (1) SA112330271B1 (enExample)
TW (1) TWI566834B (enExample)
WO (1) WO2012145241A1 (enExample)
ZA (1) ZA201307799B (enExample)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IN2015DN02639A (enExample) * 2012-09-25 2015-09-18 Dow Technology Investments Llc
US9006495B2 (en) 2012-11-30 2015-04-14 Basf Se Process for the catalytic aldol condensation of aldehydes
BR112016021934B1 (pt) * 2014-03-31 2021-10-13 Dow Technology Investments Llc Processo de hidroformilação
CN106660915B (zh) * 2014-05-14 2020-08-14 陶氏技术投资有限责任公司 稳定的有机磷化合物
EP3328818B1 (en) 2015-07-28 2020-06-03 Dow Technology Investments LLC Method for the preparation of a stabilized organophosphorous compound solution
TWI758353B (zh) * 2016-11-08 2022-03-21 美商陶氏科技投資有限公司 使去活化的氫甲醯化催化劑溶液再生的方法
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

Family Cites Families (61)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3415906A (en) 1964-05-29 1968-12-10 Hooker Chemical Corp Phosphite phospholane and phosphorinane compounds
US3527809A (en) 1967-08-03 1970-09-08 Union Carbide Corp Hydroformylation process
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
US4169861A (en) 1977-08-19 1979-10-02 Celanese Corporation Hydroformylation process
GB8334359D0 (en) 1983-12-23 1984-02-01 Davy Mckee Ltd Process
US4599206A (en) * 1984-02-17 1986-07-08 Union Carbide Corporation Transition metal complex catalyzed reactions
US5110990A (en) 1984-03-30 1992-05-05 Union Carbide Chemicals & Plastics Technology Corporation Process for recovery of phosphorus ligand from vaporized aldehyde
US4567302A (en) 1984-07-20 1986-01-28 Angus Chemical Polymeric quaternary ammonium salts possessing antimicrobial activity and methods for preparation and use thereof
US4737588A (en) 1984-12-28 1988-04-12 Union Carbide Corporation Transition metal complex catalyzed reactions
US4593127A (en) 1985-01-11 1986-06-03 Union Carbide Corporation Hydroformylation process
US4748261A (en) 1985-09-05 1988-05-31 Union Carbide Corporation Bis-phosphite compounds
US4668651A (en) 1985-09-05 1987-05-26 Union Carbide Corporation Transition metal complex catalyzed processes
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
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
US5114473A (en) 1988-08-25 1992-05-19 Union Carbide Chemicals And Plastics Technology Corporation Transition metal recovery
US5277532A (en) 1989-07-31 1994-01-11 Cefin S.P.A. Mechanical acceleration device in can welding machines
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
US5179055A (en) 1990-09-24 1993-01-12 New York University Cationic rhodium bis(dioxaphosphorus heterocycle) complexes and their use in the branched product regioselective hydroformylation of olefins
US5102505A (en) 1990-11-09 1992-04-07 Union Carbide Chemicals & Plastics Technology Corporation Mixed aldehyde product separation by distillation
US5183943A (en) * 1991-03-18 1993-02-02 Union Carbide Chemicals & Plastics Technology Corporation Reactivation of hydroformylation catalysts
TW213465B (enExample) 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
DE4204808A1 (de) 1992-02-18 1993-08-19 Basf Ag Verfahren zur herstellung von (omega)-formylalkancarbonsaeureestern
US5312996A (en) 1992-06-29 1994-05-17 Union Carbide Chemicals & Plastics Technology Corporation Hydroformylation process for producing 1,6-hexanedials
US5288918A (en) 1992-09-29 1994-02-22 Union Carbide Chemicals & Plastics Technology Corporation Hydroformylation process
US5364950A (en) * 1992-09-29 1994-11-15 Union Carbide Chimicals & Plastics Technology Corporation Process for stabilizing phosphite ligands in hydroformylation reaction mixtures
US5560405A (en) 1994-03-31 1996-10-01 Eastman Kodak Company Flow control system and method
TW307785B (enExample) * 1994-04-05 1997-06-11 Ciba Sc Holding Ag
US5786517A (en) 1995-12-06 1998-07-28 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
US5767321A (en) * 1995-12-06 1998-06-16 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
US5741942A (en) * 1996-11-26 1998-04-21 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
SK68698A3 (en) 1995-12-06 1999-02-11 Union Carbide Chem Plastic Improved metal-ligand complex catalyzed processes
US5744650A (en) * 1995-12-06 1998-04-28 Union Carbide Chemicals & Plastics Technology Corporation Metal-Ligand complex catalyzed processes
US5731472A (en) 1995-12-06 1998-03-24 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
EP0839787A1 (en) 1996-11-04 1998-05-06 Dsm N.V. Process for the preparation of an aldehyde
US5710344A (en) 1996-11-08 1998-01-20 E. I. Du Pont De Nemours And Company Process to prepare a linear aldehyde
US5892119A (en) 1996-11-26 1999-04-06 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
US5874640A (en) 1996-11-26 1999-02-23 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
AU6518398A (en) 1997-03-27 1998-10-22 Mitsubishi Chemical Corporation Process for producing aldehydes
DE19810794A1 (de) 1998-03-12 1999-09-16 Basf Ag Katalysator, umfassend einen Komplex eines Metalls der VIII. Nebengruppe auf Basis eines Phosphonitliganden und Verfahren zur Hydroformylierung
US6090987A (en) 1998-07-06 2000-07-18 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
JP3059423B2 (ja) 1998-10-19 2000-07-04 松下電子工業株式会社 半導体装置の製造方法
US6294700B1 (en) 2000-03-15 2001-09-25 Union Carbide Chemicals & Plastics Technology Corporation Separation processes
CN1225444C (zh) 2001-03-08 2005-11-02 三菱化学株式会社 醛类的制备方法
US6693219B2 (en) 2001-06-02 2004-02-17 Eastman Chemical Company Epoxide stabilization of fluorophosphite-metal catalyst system in a hydroformylation process
DE10140083A1 (de) 2001-08-16 2003-02-27 Oxeno Olefinchemie Gmbh Neue Phosphitverbindungen und deren Metallkomplexe
DE60304034T2 (de) 2002-03-11 2006-10-12 Union Carbide Chemicals & Plastics Technology Corp., Danbury Bisphosphit-ligande für carbonylierungsverfahren
DE10242636A1 (de) 2002-09-13 2004-03-18 Basf Ag Verfahren zur Herstellung von Dialdehyden und/oder ethylenisch ungesättigten Monoaldehyden durch Hydroformylierung ethylenisch ungesättigter Verbindungen
ES2308230T3 (es) 2003-10-21 2008-12-01 Basf Se Metodo para la produccion continua de aldehidos.
FR2903687B1 (fr) 2006-07-13 2008-09-26 Inst Francais Du Petrole Procede d'hydroformylation mettant en oeuvre un catalyseur a base de cobalt dans un liquide ionique non-aqueux.
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
BRPI0808297B1 (pt) 2007-03-20 2017-02-07 Dow Technology Investments Llc processo de hidroformilação
TW200940494A (en) * 2007-12-19 2009-10-01 Shell Int Research Heterogeneous promotion of oxirane hydroformylation
US7872156B2 (en) 2007-12-26 2011-01-18 Eastman Chemical Company Fluorophosphite containing catalysts for hydroformylation processes
US7674937B2 (en) 2008-05-28 2010-03-09 Eastman Chemical Company Hydroformylation catalysts

Also Published As

Publication number Publication date
CN103702758B (zh) 2016-07-06
EP2699350B1 (en) 2019-08-07
JP2014512266A (ja) 2014-05-22
KR20140027263A (ko) 2014-03-06
RU2598386C2 (ru) 2016-09-27
JP5990260B2 (ja) 2016-09-07
CA2833042A1 (en) 2012-10-26
ES2753226T3 (es) 2020-04-07
MX2013012191A (es) 2014-06-23
RU2013151001A (ru) 2015-05-27
SA112330271B1 (ar) 2015-02-09
TWI566834B (zh) 2017-01-21
EP2699350A1 (en) 2014-02-26
KR101879013B1 (ko) 2018-07-16
WO2012145241A1 (en) 2012-10-26
US20140051568A1 (en) 2014-02-20
BR112013026704B1 (pt) 2020-10-20
MY170248A (en) 2019-07-12
TW201302306A (zh) 2013-01-16
ZA201307799B (en) 2015-01-28
CN103702758A (zh) 2014-04-02
US10478812B2 (en) 2019-11-19
MX363707B (es) 2019-03-29

Similar Documents

Publication Publication Date Title
EP3230248B1 (en) Hydroformylation process
EP2516371B1 (en) Controlling the normal:iso aldehyde ratio in a mixed ligand hydroformylation process by controlling the olefin partial pressure
EP2516373B1 (en) Controlling the normal : iso aldehyde ratio in a mixed ligand hydroformylation process
CA2784943C (en) Controlling the normal:iso aldehyde ratio in a mixed ligand hydroformylation process by controlling the syngas partial pressure
EP2699350B1 (en) Methods to store transition metal organophosphorous ligand based catalysts
MX2011010379A (es) Proceso de hidroformilacion con un ligando de biosfosfito doblemente de extremo abierto.
CN111278560A (zh) 从氢甲酰化方法回收铑的方法
US20220143590A1 (en) Process to prepare solution from hydroformylation process for precious metal recovery

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20170330

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 13TH ANNIV.) - STANDARD

Year of fee payment: 13

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20250305

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT DETERMINED COMPLIANT

Effective date: 20250305

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20250305

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 14TH ANNIV.) - STANDARD

Year of fee payment: 14

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20260303

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20260303