SG10201806584VA - Ferrocene-based compounds and palladium catalysts based thereon for the alkoxycarbonylation of ethylenically unsaturated compounds - Google Patents

Ferrocene-based compounds and palladium catalysts based thereon for the alkoxycarbonylation of ethylenically unsaturated compounds

Info

Publication number
SG10201806584VA
SG10201806584VA SG10201806584VA SG10201806584VA SG10201806584VA SG 10201806584V A SG10201806584V A SG 10201806584VA SG 10201806584V A SG10201806584V A SG 10201806584VA SG 10201806584V A SG10201806584V A SG 10201806584VA SG 10201806584V A SG10201806584V A SG 10201806584VA
Authority
SG
Singapore
Prior art keywords
alkyl
cycloalkyl
compounds
aryl
alkoxycarbonylation
Prior art date
Application number
SG10201806584VA
Inventor
Kaiwu Dong Dr
Helfried Neumann Dr
Ralf Jackstell Dr
Dr Matthias Beller Prof
Dr Robert Franke Prof
Dieter Hess Dr
Katrin Marie Dyballa Dr
Fridag Dirk
Frank Geilen Dr
Original Assignee
Evonik Degussa Gmbh
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 Evonik Degussa Gmbh filed Critical Evonik Degussa Gmbh
Publication of SG10201806584VA publication Critical patent/SG10201806584VA/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/50Organo-phosphines
    • C07F9/5022Aromatic phosphines (P-C aromatic linkage)
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/12Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2282Unsaturated compounds used as ligands
    • B01J31/2295Cyclic compounds, e.g. cyclopentadienyls
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2409Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/36Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
    • C07C67/38Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by addition to an unsaturated carbon-to-carbon bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/006Palladium compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F17/00Metallocenes
    • C07F17/02Metallocenes of metals of Groups 8, 9 or 10 of the Periodic System
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/50Organo-phosphines
    • C07F9/5027Polyphosphines
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/50Organo-phosphines
    • C07F9/5045Complexes or chelates of phosphines with metallic compounds or metals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/50Organo-phosphines
    • C07F9/505Preparation; Separation; Purification; Stabilisation
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572Five-membered rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576Six-membered rings
    • C07F9/58Pyridine rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6503Five-membered rings
    • C07F9/6506Five-membered rings having the nitrogen atoms in positions 1 and 3
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/65515Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6553Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
    • C07F9/655345Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/78Preparation processes
    • C08G63/82Preparation processes characterised by the catalyst used
    • C08G63/826Metals not provided for in groups C08G63/83 - C08G63/86
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32Addition reactions to C=C or C-C triple bonds
    • B01J2231/321Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/49Esterification or transesterification
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0202Polynuclearity
    • B01J2531/0208Bimetallic complexes, i.e. comprising one or more units of two metals, with metal-metal bonds but no all-metal (M)n rings, e.g. Cr2(OAc)4
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0213Complexes without C-metal linkages
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0238Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
    • B01J2531/0241Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82Metals of the platinum group
    • B01J2531/824Palladium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84Metals of the iron group
    • B01J2531/842Iron

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)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Inorganic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Epoxy Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Peptides Or Proteins (AREA)

Abstract

RPN R2 Fe a ,R 3 P 14 R (I) where R1 , R2 , R3 , R4 are each independently selected from -(C1 -C1 2)-alkyl, -(C3 -Ci2)-cycloalkyl, -(C 3 - 10 C12 )-heterocycloalkyl, -(C6-C20)-aryl, -(C 3 -C20 )-heteroaryl; at least one of the R 1 , R2 , R 3 , R4 radicals is a -(C6-C20)-heteroaryl radical having at least six ring atoms; and R1 , R2 , R3 , R4 , if they are -(C 1 -C12 )-alkyl, -(C3 -Ci 2)-cycloalkyl, -(C3 -C1 2)-heterocycloalkyl, -(C 6 - 15 C20 )-aryl, -(C3 -C20)-heteroaryl or -(C6-C20)-heteroaryl, may each independently be substituted by one or more substituents selected from -(C1 -C12 )-alkyl, -(C3 -C12 )-cycloalkyl, -(C3-Ci2)-heterocycloalkyl, -0-(C1 -C12)-alkyl, -0-(C1-C12)- alkyl-(C6-C20)-aryl, -0-(C3-C12)-cycloalkyl, -S-(C 1 -C12)-alkyl, -S-(C3 -C12)-cycloalkyl, -000-(Ci- C1 2)-alkyl, -000-(C3-C12)-cycloalkyl, -CONH-(C1-C12)-alkyl, -CONH-(C 3 -C12 )-cycloalkyl, -CO- 20 (C1-C12)-alkyl, -00-(C3-C12)-cycloalkyl, -N-[(C1 -C12 )-alkyl]2, -(C6-C20)-aryl, -(C6 -C20 )-aryl-(C1 - C12 )-alkyl, -(C6-C20)-aryl-0-(C1-C12)-alkyl, -(C3 -C20)-heteroaryl, -(C3-C20)-heteroary1-(Ci-Ci 2)- alkyl, -(C3 -C20 )-heteroary1-0-(C1 -C1 2)-alkyl, -COOH, -OH, -SO 3 H, -NH2, halogen. The invention further relates to precursors for preparation of the compound according to the 25 invention, to Pd complexes comprising the compound according to the invention and to the use thereof in alkoxycarbonylation. (No drawing to be published)
SG10201806584VA 2015-07-23 2016-07-19 Ferrocene-based compounds and palladium catalysts based thereon for the alkoxycarbonylation of ethylenically unsaturated compounds SG10201806584VA (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE102015213918 2015-07-23

Publications (1)

Publication Number Publication Date
SG10201806584VA true SG10201806584VA (en) 2018-09-27

Family

ID=56497599

Family Applications (3)

Application Number Title Priority Date Filing Date
SG10201605918UA SG10201605918UA (en) 2015-07-23 2016-07-19 Benzene-based diphosphine ligands for alkoxycarbonylation
SG10201806584VA SG10201806584VA (en) 2015-07-23 2016-07-19 Ferrocene-based compounds and palladium catalysts based thereon for the alkoxycarbonylation of ethylenically unsaturated compounds
SG10201605921SA SG10201605921SA (en) 2015-07-23 2016-07-19 Ferrocene-based compounds and palladium catalysts based thereon for the alkoxycarbonylation of ethylenically unsaturated compounds

Family Applications Before (1)

Application Number Title Priority Date Filing Date
SG10201605918UA SG10201605918UA (en) 2015-07-23 2016-07-19 Benzene-based diphosphine ligands for alkoxycarbonylation

Family Applications After (1)

Application Number Title Priority Date Filing Date
SG10201605921SA SG10201605921SA (en) 2015-07-23 2016-07-19 Ferrocene-based compounds and palladium catalysts based thereon for the alkoxycarbonylation of ethylenically unsaturated compounds

Country Status (15)

Country Link
US (8) US9725398B2 (en)
EP (6) EP3121185B1 (en)
JP (2) JP6714459B2 (en)
KR (2) KR101828687B1 (en)
CN (7) CN106632509B (en)
AR (2) AR105389A1 (en)
BR (2) BR102016016724B1 (en)
CA (2) CA2936724C (en)
ES (6) ES2711749T3 (en)
MX (2) MX2016009397A (en)
MY (1) MY172677A (en)
PL (3) PL3121181T4 (en)
SG (3) SG10201605918UA (en)
TW (2) TWI634947B (en)
ZA (2) ZA201605001B (en)

Families Citing this family (51)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106632509B (en) 2015-07-23 2020-07-07 赢创运营有限公司 Phosphine ligands and palladium catalysts based thereon for the alkoxycarbonylation of ethylenically unsaturated compounds
PL3272732T3 (en) 2016-07-19 2020-03-31 Evonik Degussa Gmbh Method for the alcoxy carbonylation of ethylenically unsaturated compounds with monophosphin ligands
ES2718747T3 (en) 2016-07-19 2019-07-04 Evonik Degussa Gmbh Procedure for alkoxycarbonylation of ethers
EP3272759B1 (en) 2016-07-19 2019-05-08 Evonik Degussa GmbH 1,1 -bis (phosphino) ferrocene ligands for alkoxycarbonylation
EP3272728B1 (en) 2016-07-19 2019-06-19 Evonik Degussa GmbH Method for the alcoxycarbonylation of alcohols
EP3272760B1 (en) 2016-07-19 2019-05-15 Evonik Degussa GmbH 1,1'-bis(phosphino) ferrocene ligands for alkoxycarbonylation
EP3272733B1 (en) 2016-07-19 2019-01-02 Evonik Degussa GmbH Method for the alcoxycarbonylation of olefins in a medium with low brønsted acid concentration
ES2734383T3 (en) 2016-07-19 2019-12-05 Process for the production of di- or tricarboxylates by alkoxycarbonylation of dienes with conjugated double bonds
EP3272729B1 (en) 2016-07-19 2019-09-04 Evonik Degussa GmbH Method for the preparation of esters through the carbonylation of ethers
EP3596038B1 (en) * 2017-03-18 2022-12-28 Qatar Foundation for Education, Science and Community Development Metal-catalyzed alkoxycarbonylation of a lactone
EP3421478B1 (en) 2017-06-29 2020-03-25 Evonik Operations GmbH Markovnikov-selective palladium catalyst for carbonylation of alkynes with heteroarenes
EP3441383B1 (en) * 2017-08-08 2019-12-25 Evonik Operations GmbH Methoxy carbonylation with formic acid as co source
EP3441384B1 (en) * 2017-08-08 2019-12-25 Evonik Operations GmbH Methoxycarbonylation with formic acid and methanol
EP3441137B1 (en) * 2017-08-08 2019-12-25 Evonik Operations GmbH The pd-catalytic decomposition of formic acid
ES2807544T3 (en) * 2017-12-21 2021-02-23 Evonik Operations Gmbh Process for Pd-catalyzed hydroxycarbonylation of diisobutene: sulfuric acid / ligand ratio
EP3502087B1 (en) * 2017-12-21 2020-06-24 Evonik Operations GmbH Method for the pd catalytic hydroxycarbonylation of di-isobutene: acetic acid/di-isobutene ratio
ES2807998T3 (en) * 2017-12-21 2021-02-25 Evonik Operations Gmbh Process for Pd-catalyzed hydroxycarbonylation of diisobutene: ligand / Pd ratio
ES2807542T3 (en) * 2017-12-21 2021-02-23 Evonik Operations Gmbh Process for the Pd-catalyzed hydroxycarbonylation of diisobutene: 3,5,5-trimethylhexanoic acid / H2O ratio
EP3502082B1 (en) * 2017-12-21 2020-02-12 Evonik Operations GmbH Method for the pd catalytic hydroxycarbonylation of di-isobutene: influence of the solvent
EP3502084B1 (en) * 2017-12-21 2020-02-12 Evonik Operations GmbH Method for direct conversion of di-isobutene to a carboxylic acid
EP3502085B1 (en) * 2017-12-21 2020-03-11 Evonik Operations GmbH Method for direct conversion of alkenes to carboxylic acids
US10710956B2 (en) * 2018-02-08 2020-07-14 Regents Of The University Of Minnesota Process for the preparation of acrylate esters from alkyl lactates
ES2834092T3 (en) * 2018-02-14 2021-06-16 Evonik Degussa Gmbh Propyl-bridged diphosphine ligands for alkoxycarbonylation
US11365171B2 (en) 2019-06-12 2022-06-21 Evonik Operations Gmbh Process for preparing an ester by alkoxycarbonylation
US11008275B2 (en) 2019-06-12 2021-05-18 Evonik Operations Gmbh Process for preparing carboxylic acids or salts thereof from hydrocarbons
US11440863B2 (en) 2019-06-12 2022-09-13 Evonik Operations Gmbh Process for preparing an alcohol from hydrocarbons
US20200391194A1 (en) * 2019-06-12 2020-12-17 Evonik Operations Gmbh Process for separating one or more components from a mixture
PL3838886T3 (en) * 2019-12-17 2023-09-18 Evonik Operations Gmbh Alkoxycarbonylation of trivinyl cyclohexane
CN111087306B (en) 2019-12-27 2021-08-03 南京诚志清洁能源有限公司 Method for preparing organic carboxylic ester by aryl bidentate phosphine ligand combined catalysis
CN111253258A (en) * 2020-03-13 2020-06-09 华东理工大学 Method for synthesizing methyl propionate through homogeneous-phase hydroesterification of ethylene
EP3889163B1 (en) * 2020-03-30 2023-07-19 Evonik Operations GmbH Platinum complexes with ferrocene ligands for the catalysis of alkoxycarbonylation of ethylenically unsaturated compounds
EP3889161B1 (en) * 2020-03-30 2022-06-08 Evonik Operations GmbH Platinum complexes with benzyl-based diphosphine ligands for the catalysis of alkoxycarbonylation of ethylenically unsaturated compounds
CN113801161A (en) * 2020-06-15 2021-12-17 华东师范大学 Imidazole ligand derivative, preparation thereof and application thereof in butadiene telomerization reaction
CN111686818B (en) * 2020-07-10 2022-08-02 万华化学集团股份有限公司 Catalyst composition and application thereof in propylene hydroformylation reaction
CN112094294A (en) * 2020-11-10 2020-12-18 江苏欣诺科催化剂有限公司 Synthesis method of bis (dicyclohexylphosphine) alkane
EP4001252A1 (en) 2020-11-12 2022-05-25 Evonik Operations GmbH Double alkoxycarbonylation of dienes
EP4001256A1 (en) 2020-11-24 2022-05-25 Evonik Operations GmbH Method for alkoxycarbonylation of ethylenically unsaturated compounds using benzene-based diphosphine ligands and aluminum triflate
CN112480170B (en) * 2020-12-02 2023-03-14 中国海洋石油集团有限公司 Diphosphine compound, catalyst system containing same and application thereof
EP4011892A1 (en) 2020-12-09 2022-06-15 Evonik Operations GmbH Platinum complexes with ferrocene diphosphine ligands for the catalysis of hydroxy carbonylation of ethylenically unsaturated compounds
CN114835746A (en) * 2021-02-01 2022-08-02 惠州凯特立斯科技有限公司 Novel tetradentate phosphine ligand compound and synthetic method and application thereof
CN113620990B (en) * 2021-08-30 2022-11-08 万华化学集团股份有限公司 Thiourea type nitrogen phosphine ligand and preparation method and application thereof
CN113788748A (en) * 2021-09-15 2021-12-14 华东师范大学 Method for preparing straight-chain carbonyl compound by catalyzing unsaturated hydrocarbon with multidentate phosphine ligand modified palladium combined catalyst
CN113969188B (en) * 2021-10-21 2022-10-28 青岛科技大学 Novel turpentine-based biomass high-energy-density mixed fuel
CN114014895A (en) * 2021-10-26 2022-02-08 浙江大学 Ferrocenyl phosphine ligand compound and synthesis method thereof
CN113999261B (en) * 2021-10-26 2023-06-06 浙江大学 O-dimethyl aromatic ring type diphosphine ligand compound and synthesis method thereof
CN114308129B (en) * 2021-11-24 2022-12-06 中国科学院兰州化学物理研究所 Catalyst composition for olefin alkoxycarbonylation and preparation method and application thereof
EP4197619A1 (en) 2021-12-20 2023-06-21 Evonik Operations GmbH Process for producing carbon monoxide containing streams
EP4198014A1 (en) 2021-12-20 2023-06-21 Evonik Operations GmbH Method for the preparation of carboxylic acids or their salts and separation of the homogeneous catalyst system using a membrane comprising a separation-active layer of paek and a substructure comprising paek
EP4197992A1 (en) 2021-12-20 2023-06-21 Evonik Operations GmbH Method for the preparation of an alcohol and separation of the homogeneous catalyst system using a membrane comprising a separation-active layer of paek and a substructure comprising paek
EP4197623A1 (en) 2021-12-20 2023-06-21 Evonik Operations GmbH Method for the preparation of an ester and separation of the homogeneous catalyst system using a membrane comprising a separation-active layer of paek and a substructure comprising paek
WO2023222359A1 (en) 2022-05-18 2023-11-23 Evonik Oxeno Gmbh & Co. Kg Process for purifying hydrocarbon streams including heterogeneously and homogeneously catalysed reactions

Family Cites Families (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1029839B (en) 1953-05-07 1958-05-14 Tosaku Yoshioka Means for improving and regulating the fertilizer effect on agricultural cultivated soils
US3213093A (en) * 1963-12-12 1965-10-19 American Cyanamid Co Phosphino-s-triazines
US5166330A (en) * 1983-09-06 1992-11-24 Hoechst Aktiengesellschaft Process for the preparation of nucleoside alkyl-aralkyl- and aryl-phosphonites and -phosphonates
DK166686A (en) * 1985-04-16 1986-10-17 Smithkline Beckman Corp PHOSPHINE COMPOUNDS, PROCEDURES FOR PREPARING THEM AND PHARMACEUTICAL AGENTS CONTAINING THESE COMPOUNDS
GB8705699D0 (en) * 1987-03-11 1987-04-15 Shell Int Research Carbonylation of olefinically unsaturated compounds
US4880902A (en) * 1987-08-27 1989-11-14 Shell Oil Company Copolymerization of carbon monoxide and olefin with diphosphine having heterocyclic substituents as catalyst
CN1024635C (en) * 1989-03-03 1994-05-25 国际壳牌研究有限公司 Carbonylation catalyst system
KR0148012B1 (en) 1989-03-03 1998-08-17 오노 알버어스 Carbonylation catalyst system
CA2034971A1 (en) * 1990-02-05 1991-08-06 Eit Drent Carbonylation catalyst system
GB9002521D0 (en) * 1990-02-05 1990-04-04 Shell Int Research Carbonylation catalyst system
DE69204691T2 (en) * 1991-01-15 1996-04-11 Shell Int Research Process for carbonylation of olefin.
DE4141299C2 (en) * 1991-12-14 2000-09-21 Celanese Chem Europe Gmbh Process for the preparation of tertiary phosphines
EP0577205B1 (en) * 1992-06-29 1997-10-08 Shell Internationale Researchmaatschappij B.V. Carbonylation of conjugated dienes
BE1007422A3 (en) * 1993-08-23 1995-06-13 Dsm Nv PROCESS FOR THE PREPARATION OF A MIXTURE OF alkyl pentenoates.
BE1008018A3 (en) * 1994-01-06 1995-12-12 Dsm Nv Process for the preparation of an ester.
TW272949B (en) * 1994-07-22 1996-03-21 Taishal Kagaku Kogyo Kk
EP0975574A1 (en) 1997-02-26 2000-02-02 Dsm N.V. Process to prepare a pentenoic acid derivative
GB9717059D0 (en) 1997-08-13 1997-10-15 Ici Plc Method of manufacturing phosphine compound
DE19906518A1 (en) 1999-02-17 2000-08-31 Oxeno Olefinchemie Gmbh Dibutene fractionation process
DE10037961A1 (en) 2000-07-27 2002-02-07 Aventis Res & Tech Gmbh & Co New phosphine ligands, their production and their use in catalytic reactions
JP4467935B2 (en) * 2002-10-03 2010-05-26 キヤノン株式会社 Method for producing halogenated aromatic amine compound
CA2548925A1 (en) * 2003-12-12 2005-06-23 Solvias Ag Method for producing orthometalated and orthosubstituted metallocences
GB0400720D0 (en) * 2004-01-14 2004-02-18 Stylacats Ltd Novel ferrocene-based phosphorus chiral phosphines
JP5015451B2 (en) * 2005-04-18 2012-08-29 日本化学工業株式会社 Phosphine transition metal complex, process for producing the same, and anticancer agent containing the same
CN101235052A (en) * 2007-09-30 2008-08-06 赢创德固赛有限责任公司 Asymmetric chirality diphosphine ligand
DE102008007081B4 (en) 2008-01-31 2018-12-06 Evonik Degussa Gmbh Process for the preparation of n-butene oligomers and 1-butene from technical mixtures I of C4-hydrocarbons
GB0915946D0 (en) 2009-09-11 2009-10-28 Univ St Andrews Metal-catalysed carbonylation of unsaturated compounds
GB201000078D0 (en) * 2010-01-05 2010-02-17 Lucite Int Uk Ltd Process for the carbonylation of ethylenically unsaturated compounds, novel carbonylation ligands and catalyst systems incorporatng such ligands
JP5746915B2 (en) * 2010-05-31 2015-07-08 住友化学株式会社 Film containing silver complex
CN102531890A (en) 2010-12-18 2012-07-04 中国科学院兰州化学物理研究所 Method for preparing organic carboxylate from olefin through hydroesterification
JP6011798B2 (en) * 2011-02-17 2016-10-19 国立大学法人 岡山大学 Novel compounds, novel ligands, novel transition metal complexes, and catalysts comprising novel transition metal complexes
DE102011089008B4 (en) 2011-12-19 2017-08-24 Evonik Degussa Gmbh Process for the preparation of esters of formates and olefinically unsaturated compounds
DE102013201669B4 (en) * 2013-02-01 2017-02-09 Evonik Degussa Gmbh Process for the carbonylation of olefins
KR102205983B1 (en) * 2014-10-13 2021-01-22 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
CN106632509B (en) 2015-07-23 2020-07-07 赢创运营有限公司 Phosphine ligands and palladium catalysts based thereon for the alkoxycarbonylation of ethylenically unsaturated compounds
ES2834092T3 (en) * 2018-02-14 2021-06-16 Evonik Degussa Gmbh Propyl-bridged diphosphine ligands for alkoxycarbonylation

Also Published As

Publication number Publication date
CA2936723C (en) 2019-03-19
CA2936723A1 (en) 2017-01-23
TW201718093A (en) 2017-06-01
MY172677A (en) 2019-12-10
EP3121180A3 (en) 2017-02-08
BR102016016724B1 (en) 2021-06-29
ZA201605001B (en) 2017-09-27
US20170022234A1 (en) 2017-01-26
JP6840480B2 (en) 2021-03-10
PL3121181T4 (en) 2019-07-31
ES2705078T3 (en) 2019-03-21
MX2016009397A (en) 2017-03-30
ES2703563T3 (en) 2019-03-11
ES2705723T3 (en) 2019-03-26
US10077228B2 (en) 2018-09-18
US20230348356A1 (en) 2023-11-02
AR105388A1 (en) 2017-09-27
US20170022236A1 (en) 2017-01-26
US20170022138A1 (en) 2017-01-26
CN106632476A (en) 2017-05-10
CN106632509B (en) 2020-07-07
EP3121185A3 (en) 2017-02-22
US9688604B2 (en) 2017-06-27
US10294191B2 (en) 2019-05-21
AR105389A1 (en) 2017-09-27
SG10201605918UA (en) 2017-02-27
PL3121180T3 (en) 2019-03-29
CN106632509A (en) 2017-05-10
BR102016016726A2 (en) 2017-01-31
CN106366126B (en) 2019-09-27
TWI648283B (en) 2019-01-21
PL3121181T3 (en) 2019-06-28
EP3121186A3 (en) 2017-02-08
US20210276939A1 (en) 2021-09-09
US10202329B2 (en) 2019-02-12
EP3121184B1 (en) 2018-09-12
BR102016016724A2 (en) 2017-02-14
EP3121179B1 (en) 2018-10-17
EP3121186B1 (en) 2018-09-12
CN106632476B (en) 2020-11-20
CN106432364B (en) 2020-11-20
EP3121184A3 (en) 2017-02-08
EP3121185A2 (en) 2017-01-25
JP2017114843A (en) 2017-06-29
CN113845545A (en) 2021-12-28
EP3121185B1 (en) 2018-11-14
CN106432364A (en) 2017-02-22
EP3121181A2 (en) 2017-01-25
TW201716422A (en) 2017-05-16
KR101828687B1 (en) 2018-02-12
CN106432365B (en) 2020-04-07
TWI634947B (en) 2018-09-11
US9725398B2 (en) 2017-08-08
MX2016009398A (en) 2017-03-30
US20170022139A1 (en) 2017-01-26
BR102016016726B1 (en) 2022-05-03
US20170022235A1 (en) 2017-01-26
CN106397484A (en) 2017-02-15
EP3121179A3 (en) 2017-02-08
JP6714459B2 (en) 2020-06-24
ZA201605000B (en) 2017-08-30
US20170022137A1 (en) 2017-01-26
CA2936724C (en) 2018-06-19
PL3121184T3 (en) 2019-03-29
KR101878043B1 (en) 2018-07-12
EP3121184A2 (en) 2017-01-25
EP3121181B1 (en) 2018-11-28
EP3121180A2 (en) 2017-01-25
EP3121186A2 (en) 2017-01-25
ES2711749T3 (en) 2019-05-07
CA2936724A1 (en) 2017-01-23
ES2714150T3 (en) 2019-05-27
CN106432365A (en) 2017-02-22
EP3121179A2 (en) 2017-01-25
SG10201605921SA (en) 2017-02-27
KR20170012065A (en) 2017-02-02
EP3121181A3 (en) 2017-02-08
ES2702924T3 (en) 2019-03-06
KR20170012066A (en) 2017-02-02
EP3121180B1 (en) 2018-09-12
CN106366126A (en) 2017-02-01
JP2017061443A (en) 2017-03-30

Similar Documents

Publication Publication Date Title
SG10201806584VA (en) Ferrocene-based compounds and palladium catalysts based thereon for the alkoxycarbonylation of ethylenically unsaturated compounds
SA520420157B1 (en) Bisindenyl ligands, complexes thereof and catalysts comprising those complexes
PH12020500195A1 (en) Pyrimidinones as factor xia inhibitors
MX2017009233A (en) 1, 1' -bis(phosphino)ferrocene ligands for alkoxycarbonylation.
MX2018012016A (en) Bicyclic compounds.
MX2023011282A (en) C40-, c28-, and c-32-linked rapamycin analogs as mtor inhibitors.
MX2023007581A (en) C26-linked rapamycin analogs as mtor inhibitors.
SG10201908467RA (en) Macrocycles with hetrocyclic p2' groups as factor xia inhibitors
MX2016009385A (en) Macrocyclic factor xia inhibitors condensed with heterocycles.
WO2015142001A3 (en) Compound having cardiotonic activity and pharmaceutical composition for preventing or treating heart failure, containing same
NZ704660A (en) Process for making isoquinoline compounds
MX2016016143A (en) Substituted [1,2,4]triazole compounds.
MX345763B (en) Novel macrocycles as factor xia inhibitors.
MY195343A (en) A Novel Phtalazinone Derivatives and Manufacturing Process Thereof
WO2014140884A3 (en) Methods and devices for removal of immunosuppressive ligands
JP2017536228A5 (en)
MX2015010003A (en) C-19 modified triterpenoids with hiv maturation inhibitory activity.
MY196082A (en) Imidazo[1,2- ?]pyridine derivatives, methods for preparing the same and use thereof
MA43250B1 (en) Oxadiazaspiro compounds for the treatment of drug abuse and dependence
JOP20200089A1 (en) Novel macrocyclic derivatives, process for preparing same and pharmaceutical compositions containing same
MX2017009237A (en) 1,1'-bis(phosphino)ferrocene ligands for alkoxycarbonylation.
MY179626A (en) Process for the preparation of esters by means of carbonylation of ethers
WO2016056023A3 (en) Intermediates and processes to prepare micafungin
MX2022001549A (en) New telescoping syntheses of 2-methoxymethyl-p-phenylenediamine.
WO2017046816A3 (en) Process for the preparation of derivatives of benzodioxole