EP3924395A4 - B!s(aryl phenolate) lewis base catalysts and methods thereof - Google Patents

B!s(aryl phenolate) lewis base catalysts and methods thereof Download PDF

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Publication number
EP3924395A4
EP3924395A4 EP20756711.6A EP20756711A EP3924395A4 EP 3924395 A4 EP3924395 A4 EP 3924395A4 EP 20756711 A EP20756711 A EP 20756711A EP 3924395 A4 EP3924395 A4 EP 3924395A4
Authority
EP
European Patent Office
Prior art keywords
methods
lewis base
base catalysts
phenolate
aryl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP20756711.6A
Other languages
German (de)
French (fr)
Other versions
EP3924395A1 (en
Inventor
Georgy P. GORYUNOV
Vladislav A. POPOV
Dmitry V UBORSKY
Alexander Z. Voskoboynikov
John R. Hagadorn
Irene C. CAI
Hua Zhou
Jo Ann M. Canich
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.)
ExxonMobil Chemical Patents Inc
Original Assignee
ExxonMobil Chemical Patents Inc
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 ExxonMobil Chemical Patents Inc filed Critical ExxonMobil Chemical Patents Inc
Publication of EP3924395A1 publication Critical patent/EP3924395A1/en
Publication of EP3924395A4 publication Critical patent/EP3924395A4/en
Pending legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F10/00Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F110/00Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F110/02Ethene
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F110/00Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F110/04Monomers containing three or four carbon atoms
    • C08F110/06Propene
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F110/00Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F110/14Monomers containing five or more carbon atoms
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F210/00Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F210/16Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00Polymerisation catalysts
    • C08F4/02Carriers therefor
    • C08F4/022Magnesium halide as support anhydrous or hydrated or complexed by means of a Lewis base for Ziegler-type catalysts
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00Polymerisation catalysts
    • C08F4/42Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/62Refractory metals or compounds thereof
    • C08F4/64Titanium, zirconium, hafnium or compounds thereof
    • C08F4/64003Titanium, zirconium, hafnium or compounds thereof the metallic compound containing a multidentate ligand, i.e. a ligand capable of donating two or more pairs of electrons to form a coordinate or ionic bond
    • C08F4/64082Tridentate ligand
    • C08F4/6411Monoanionic ligand
    • C08F4/64124ONO
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00Polymerisation catalysts
    • C08F4/42Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/62Refractory metals or compounds thereof
    • C08F4/64Titanium, zirconium, hafnium or compounds thereof
    • C08F4/659Component covered by group C08F4/64 containing a transition metal-carbon bond
    • C08F4/65908Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00Polymerisation catalysts
    • C08F4/42Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/62Refractory metals or compounds thereof
    • C08F4/64Titanium, zirconium, hafnium or compounds thereof
    • C08F4/659Component covered by group C08F4/64 containing a transition metal-carbon bond
    • C08F4/65912Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00Polymerisation catalysts
    • C08F4/42Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/62Refractory metals or compounds thereof
    • C08F4/64Titanium, zirconium, hafnium or compounds thereof
    • C08F4/659Component covered by group C08F4/64 containing a transition metal-carbon bond
    • C08F4/65916Component covered by group C08F4/64 containing a transition metal-carbon bond supported on a carrier, e.g. silica, MgCl2, polymer
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00Polymerisation catalysts
    • C08F4/42Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/62Refractory metals or compounds thereof
    • C08F4/64Titanium, zirconium, hafnium or compounds thereof
    • C08F4/659Component covered by group C08F4/64 containing a transition metal-carbon bond

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
EP20756711.6A 2019-02-12 2020-02-11 B!s(aryl phenolate) lewis base catalysts and methods thereof Pending EP3924395A4 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201962804372P 2019-02-12 2019-02-12
EP19179811 2019-06-12
PCT/US2020/017740 WO2020167824A1 (en) 2019-02-12 2020-02-11 B!s(aryl phenolate) lewis base catalysts and methods thereof

Publications (2)

Publication Number Publication Date
EP3924395A1 EP3924395A1 (en) 2021-12-22
EP3924395A4 true EP3924395A4 (en) 2022-06-22

Family

ID=72045086

Family Applications (2)

Application Number Title Priority Date Filing Date
EP20755182.1A Pending EP3924394A4 (en) 2019-02-12 2020-02-11 Transition metal bis(phenolate) complexes and their use as catalysts for olefin polymerization
EP20756711.6A Pending EP3924395A4 (en) 2019-02-12 2020-02-11 B!s(aryl phenolate) lewis base catalysts and methods thereof

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP20755182.1A Pending EP3924394A4 (en) 2019-02-12 2020-02-11 Transition metal bis(phenolate) complexes and their use as catalysts for olefin polymerization

Country Status (6)

Country Link
EP (2) EP3924394A4 (en)
JP (1) JP7242879B2 (en)
KR (1) KR20210118204A (en)
CN (2) CN113423742B (en)
SG (2) SG11202107809TA (en)
WO (3) WO2020167821A1 (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022072180A1 (en) 2020-09-30 2022-04-07 Exxonmobil Chemical Patents Inc. Bis(heterocyclic-olate) lewis base catalysts and methods thereof
WO2022087121A1 (en) * 2020-10-22 2022-04-28 Exxonmobil Chemical Patents Inc. Multidentate lewis base catalysts and methods for use thereof
CN112358498B (en) * 2020-10-27 2023-03-03 万华化学集团股份有限公司 Tetraaryloxy IVB group binuclear metal complex and preparation and application thereof
WO2022146634A1 (en) 2020-12-29 2022-07-07 Exxonmobil Chemical Patents Inc. Polyolefin-based ionomers and production thereof
CN115838449B (en) * 2021-09-18 2024-03-29 中国科学技术大学 Metal catalyst, preparation method thereof and olefin polymerization method
CA3241034A1 (en) 2021-12-17 2023-06-22 Exxonmobil Chemical Patents Inc. Processes for making propylene-based copolymers having broad cds and mwds
WO2023215695A1 (en) * 2022-05-04 2023-11-09 Exxonmobil Chemical Patents Inc. Substituted pyridine-2,6-bis (phenylenephenolate) complexes with enhanced solubility that are useful as catalyst components for olefin polymerization
WO2023215694A1 (en) * 2022-05-04 2023-11-09 Exxonmobil Chemical Patents Inc. Substituted pyridine-2,6-bis(phenylenephenolate) complexes with enhanced solubility that are useful as catalyst components for olefin polymerization
WO2023215693A1 (en) * 2022-05-04 2023-11-09 Exxonmobil Chemical Patents Inc. Substituted pyridine-2,6-bis(phenylenephenolate) complexes with enhanced solubility that are useful as catalyst components for olefin polymerization
WO2024167619A1 (en) 2023-02-08 2024-08-15 ExxonMobil Technology and Engineering Company Catalysts for copolymerizations

Citations (3)

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US20080177020A1 (en) * 2006-09-21 2008-07-24 Theodor Agapie Non-metallocene organometallic complexes and related methods and systems
US20160289351A1 (en) * 2014-05-15 2016-10-06 Chevron Phillips Chemical Company Lp Synthesis of Aryl Coupled BIS Phenoxides and Their Use in Olefin Polymerization Catalyst Systems With Activator-Supports
KR20180022137A (en) * 2016-08-23 2018-03-06 주식회사 엘지화학 Novel ligand compound and transition metal compound comprising the same

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JP5595059B2 (en) * 2010-02-10 2014-09-24 三井化学株式会社 Organometallic polyolefin catalyst component
CN103596686B (en) * 2011-06-08 2015-08-12 埃克森美孚化学专利公司 Comprise the catalyst system of multiple non-coordinating anion activator and use its polymerization process
US8969482B2 (en) * 2011-09-30 2015-03-03 Exxonmobil Chemical Patents Inc. Dynamic modulation of metallocene catalysts
WO2014210333A1 (en) * 2013-06-28 2014-12-31 Dow Global Technologies Llc Molecular weight control of polyolefins using halogenated bis-phenylphenoxy catalysts
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US20160289351A1 (en) * 2014-05-15 2016-10-06 Chevron Phillips Chemical Company Lp Synthesis of Aryl Coupled BIS Phenoxides and Their Use in Olefin Polymerization Catalyst Systems With Activator-Supports
KR20180022137A (en) * 2016-08-23 2018-03-06 주식회사 엘지화학 Novel ligand compound and transition metal compound comprising the same

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Title
GOLISZ S R ET AL: "Synthesis of Early Transition Metal Bisphenolate Complexes and Their Use as Olefin Polymerization Catalysts", MACROMOLECULES, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, UNITED STATES, vol. 42, no. 22, 24 November 2009 (2009-11-24), pages 8751 - 8762, XP001552523, ISSN: 0024-9297, [retrieved on 20091029], DOI: 10.1021/MA901659Q *
MATTHIAS LEIN ET AL: "Identification of non-classical C-H...M interactions in early and late transition metal complexes containing the CH(ArO)3 ligand", DALTON TRANSACTIONS, vol. 42, no. 30, 1 January 2013 (2013-01-01), pages 10939, XP055654332, ISSN: 1477-9226, DOI: 10.1039/c3dt51028j *
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THEODOR AGAPIE ET AL: "Zirconium and Titanium Complexes Supported by Tridentate LX2 Ligands Having Two Phenolates Linked to Furan, Thiophene, and Pyridine Donors: Precatalysts for Propylene Polymerization and Oligomerization", ORGANOMETALLICS, AMERICAN CHEMICAL SOCIETY, US, vol. 27, no. 23, 8 December 2008 (2008-12-08), pages 6245 - 6256, XP002743333, ISSN: 0276-7333, [retrieved on 20081106], DOI: 10.1021/OM800136Y *

Also Published As

Publication number Publication date
CN113423742B (en) 2023-05-05
EP3924395A1 (en) 2021-12-22
SG11202108252UA (en) 2021-08-30
JP2022520575A (en) 2022-03-31
WO2020167799A1 (en) 2020-08-20
EP3924394A1 (en) 2021-12-22
EP3924394A4 (en) 2022-06-22
CN113614123A (en) 2021-11-05
JP7242879B2 (en) 2023-03-20
WO2020167821A1 (en) 2020-08-20
SG11202107809TA (en) 2021-08-30
WO2020167824A1 (en) 2020-08-20
CN113614123B (en) 2024-01-23
CN113423742A (en) 2021-09-21
KR20210118204A (en) 2021-09-29

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