WO2018182982A3 - Metallocene-catalyzed polyalpha-olefins - Google Patents

Metallocene-catalyzed polyalpha-olefins Download PDF

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Publication number
WO2018182982A3
WO2018182982A3 PCT/US2018/022534 US2018022534W WO2018182982A3 WO 2018182982 A3 WO2018182982 A3 WO 2018182982A3 US 2018022534 W US2018022534 W US 2018022534W WO 2018182982 A3 WO2018182982 A3 WO 2018182982A3
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WO
WIPO (PCT)
Prior art keywords
hydrogen
independently
polyalpha
hydrocarbyl group
metallocene
Prior art date
Application number
PCT/US2018/022534
Other languages
French (fr)
Other versions
WO2018182982A2 (en
Inventor
Donna J. Crowther
Patrick C. Chen
Jacqueline A. Lovell
Md Safatul Islam
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.
Priority to CN201880031360.4A priority Critical patent/CN110709431B/en
Priority to SG11201908501X priority patent/SG11201908501XA/en
Priority to EP18713559.5A priority patent/EP3601381A2/en
Publication of WO2018182982A2 publication Critical patent/WO2018182982A2/en
Publication of WO2018182982A3 publication Critical patent/WO2018182982A3/en

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F110/14—Monomers containing five or more carbon 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
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/1608—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes the ligands containing silicon
    • 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
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/2243—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
    • 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
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/04—Reduction, e.g. hydrogenation
    • 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
    • B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
    • B01J2231/12—Olefin polymerisation or copolymerisation
    • B01J2231/122—Cationic (co)polymerisation, e.g. single-site or Ziegler-Natta type
    • 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
    • B01J2231/20—Olefin oligomerisation or telomerisation
    • 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
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/48—Zirconium
    • 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
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/49—Hafnium
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; 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
    • C08F4/60—Metals; 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
    • C08F4/62—Refractory metals or compounds thereof
    • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
    • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
    • C08F4/65908—Component 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+
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; 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
    • C08F4/60—Metals; 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
    • C08F4/62—Refractory metals or compounds thereof
    • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
    • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
    • C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound

Abstract

Unsaturated and hydrogenated polyalpha-olefin products can be made with a high selectivity toward vinylidenes and tri-substituted vinylenes combined, a high selectivity toward vinylidenes, and a low selectivity toward 1,2-di-substituted vinylenes by using a catalyst system comprising a metallocene compound having the following structure in the polymerization reaction: In formula (F-MC), Rl and R4 are each independently a hydrogen or a C1-C30 hydrocarbyl group, R2 and R3 are each independently a C1-C50 hydrocarbyl group, R5, R6, R7 and R8 are each independently a hydrogen or a C1-C30 hydrocarbyl group, provided that R6 and R7 are not both hydrogen. The first Cp ring and the second Cp ring may be annelated but not simultaneously.
PCT/US2018/022534 2017-03-28 2018-03-15 Metallocene-catalyzed polyalpha-olefins WO2018182982A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN201880031360.4A CN110709431B (en) 2017-03-28 2018-03-15 Metallocene catalyzed polyalphaolefins
SG11201908501X SG11201908501XA (en) 2017-03-28 2018-03-15 Metallocene-catalyzed polyalpha-olefins
EP18713559.5A EP3601381A2 (en) 2017-03-28 2018-03-15 Metallocene-catalyzed polyalpha-olefins

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201762477683P 2017-03-28 2017-03-28
US62/477,683 2017-03-28
EP17174270.3 2017-06-02
EP17174270 2017-06-02

Publications (2)

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WO2018182982A2 WO2018182982A2 (en) 2018-10-04
WO2018182982A3 true WO2018182982A3 (en) 2018-11-08

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Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10968290B2 (en) 2017-03-28 2021-04-06 Exxonmobil Chemical Patents Inc. Metallocene-catalyzed polyalpha-olefins
CA3090994A1 (en) 2018-02-12 2019-08-15 Exxonmobil Chemical Patents Inc. Catalyst systems and processes for poly alpha-olefin having high vinylidene content
US11078308B2 (en) 2018-02-12 2021-08-03 Exxonmobil Chemical Patents Inc. Processes to produce poly alpha-olefin trimers
US11021553B2 (en) 2018-02-12 2021-06-01 Exxonmobil Chemical Patents Inc. Metallocene dimer selective catalysts and processes to produce poly alpha-olefin dimers
EP3853191A4 (en) 2018-09-17 2022-08-24 ExxonMobil Chemical Patents Inc. Processes to produce poly alpha-olefin trimer and apparatus therefor
CN114502521A (en) 2019-08-09 2022-05-13 埃克森美孚化学专利公司 Process for producing low viscosity polyalphaolefins using non-aromatic hydrocarbon soluble activators
CN114845980A (en) 2019-10-28 2022-08-02 埃克森美孚化学专利公司 Dimer-selective metallocene catalyst, non-aromatic hydrocarbon soluble activator and method for preparing poly alpha-olefin oligomer using the same
US11613593B2 (en) 2020-02-24 2023-03-28 Exxonmobil Chemical Patents Inc. Ansa-bis(inden-2-yl) catalysts for producing vinylidene-terminated polyalphaolefins
CA3176627A1 (en) 2020-04-29 2021-11-04 Mark H. Li Poly alpha-olefin compositions and processes to produce poly alpha-olefins
US20230212330A1 (en) * 2020-06-16 2023-07-06 Exxonmobil Chemical Patents Inc. Metallocene Catalysts for Producing Vinyl-Terminated Polyalphaolefins and Methods Associated Therewith
KR20230142275A (en) * 2022-04-01 2023-10-11 한화솔루션 주식회사 Transition Metal Compound for a Catalyst for Olefin Polymerization, Catalyst for Olefin Polymerization Comprising the Same, and Polyolefin Polymerized Using the Same

Citations (4)

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US20030105251A1 (en) * 2001-10-31 2003-06-05 Crowther Donna Jean Methods for adjusting melt properties of metallocene catalyzed olefin copolymers
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