[go: up one dir, main page]

WO2018182982A3 - Metallocene-catalyzed polyalpha-olefins - Google Patents

Metallocene-catalyzed polyalpha-olefins Download PDF

Info

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
Authority
WO
WIPO (PCT)
Prior art keywords
hydrogen
independently
polyalpha
hydrocarbyl group
metallocene
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.)
Ceased
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
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
Priority to CN201880031360.4A priority Critical patent/CN110709431B/en
Priority to EP18713559.5A priority patent/EP3601381A2/en
Priority to SG11201908501X priority patent/SG11201908501XA/en
Publication of WO2018182982A2 publication Critical patent/WO2018182982A2/en
Publication of WO2018182982A3 publication Critical patent/WO2018182982A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

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 Ceased 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
EP18713559.5A EP3601381A2 (en) 2017-03-28 2018-03-15 Metallocene-catalyzed polyalpha-olefins
SG11201908501X SG11201908501XA (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)

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

Family

ID=59091317

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2018/022534 Ceased WO2018182982A2 (en) 2017-03-28 2018-03-15 Metallocene-catalyzed polyalpha-olefins

Country Status (1)

Country Link
WO (1) WO2018182982A2 (en)

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
US11021553B2 (en) 2018-02-12 2021-06-01 Exxonmobil Chemical Patents Inc. Metallocene dimer selective catalysts and processes to produce poly alpha-olefin dimers
CN111868106B (en) 2018-02-12 2023-02-17 埃克森美孚化学专利公司 Catalyst systems and methods for polyalphaolefins with high vinylidene content
US11078308B2 (en) 2018-02-12 2021-08-03 Exxonmobil Chemical Patents Inc. Processes to produce poly alpha-olefin trimers
EP3853273A4 (en) 2018-09-17 2022-08-31 ExxonMobil Chemical Patents Inc. Metallocene dimer selective catalysts and processes to produce poly alpha-olefin dimers
US12344696B2 (en) 2019-08-09 2025-07-01 Exxonmobil Chemical Patents Inc. Process to produce 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
CN115943197A (en) 2020-04-29 2023-04-07 埃克森美孚化学专利公司 Polyalphaolefin composition and process for producing polyalphaolefin
WO2021257264A1 (en) * 2020-06-16 2021-12-23 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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1026177A1 (en) * 1997-10-22 2000-08-09 Chisso Corporation Supported metallocene catalyst, process for preparing the same, and process for producing olefin polymers
US20020010077A1 (en) * 1998-05-15 2002-01-24 Ching-Tai Lue Mixed catalysts and their use in a polymerization process
US20030105251A1 (en) * 2001-10-31 2003-06-05 Crowther Donna Jean Methods for adjusting melt properties of metallocene catalyzed olefin copolymers
US20130023633A1 (en) * 2011-03-25 2013-01-24 Exxonmobil Chemical Patents Inc. Vinyl Terminated Higher Olefin Polymers and Methods to Produce Thereof

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5573657A (en) 1991-07-24 1996-11-12 Mobil Oil Corporation Hydrogenation process
CA2110654C (en) 1992-12-17 2006-03-21 Albert Rossi Dilute process for the polymerization of ethylene/alpha-olefin copolymer using metallocene catalyst systems
US6846778B2 (en) 2002-10-08 2005-01-25 Exxonmobil Research And Engineering Company Synthetic isoparaffinic premium heavy lubricant base stock
US7344631B2 (en) 2002-10-08 2008-03-18 Exxonmobil Research And Engineering Company Oxygenate treatment of dewaxing catalyst for greater yield of dewaxed product
US7053254B2 (en) 2003-11-07 2006-05-30 Chevron U.S.A, Inc. Process for improving the lubricating properties of base oils using a Fischer-Tropsch derived bottoms
US20080045614A1 (en) 2004-06-08 2008-02-21 Gerard Benard Process to Make a Base Oil
EP1910431B1 (en) 2005-07-19 2013-11-27 ExxonMobil Chemical Patents Inc. Polyalpha-olefin compositions and processes to produce the same
US8476205B2 (en) 2008-10-03 2013-07-02 Exxonmobil Research And Engineering Company Chromium HVI-PAO bi-modal lubricant compositions
CN104411777B (en) 2012-08-03 2017-10-24 埃克森美孚化学专利公司 Catalyst containing Salan ligand
US9458403B2 (en) 2012-09-27 2016-10-04 Exxonmobil Research And Engineering Company High viscosity, functionalized metallocene polyalphaolefin base stocks and processes for preparing same

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1026177A1 (en) * 1997-10-22 2000-08-09 Chisso Corporation Supported metallocene catalyst, process for preparing the same, and process for producing olefin polymers
US20020010077A1 (en) * 1998-05-15 2002-01-24 Ching-Tai Lue Mixed catalysts and their use in a polymerization process
US20030105251A1 (en) * 2001-10-31 2003-06-05 Crowther Donna Jean Methods for adjusting melt properties of metallocene catalyzed olefin copolymers
US20130023633A1 (en) * 2011-03-25 2013-01-24 Exxonmobil Chemical Patents Inc. Vinyl Terminated Higher Olefin Polymers and Methods to Produce Thereof

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ANTONIO ANTIÑOLO ET AL: "Reactivity of Zirconium Complexes Incorporating Asymmetrically Substituted ansa Ligands and Their Use as Catalysts in Olefin Polymerization. X-ray Crystal Structures of [Me2Si(ç5-C5Me4)(ç5-C5H3R)]ZrCl2 (R = Et, iPr)", ORGANOMETAL, AMERICAN CHEMICAL SOCIETY, US, vol. 21, no. 12, 1 January 2002 (2002-01-01), pages 2460 - 2467, XP008154075, ISSN: 0276-7333, DOI: 10.1021/OM0110639 *
CARLOS ALONSO-MORENO ET AL: "Novel Indenylzirconium Complexes as Supported Catalysts in the Polymerization of Ethylene", EUROPEAN JOURNAL OF INORGANIC CHEMISTRY - CHEMISCHE BERICHTE, vol. 2005, no. 14, 1 July 2005 (2005-07-01), DE, pages 2924 - 2934, XP055388542, ISSN: 1434-1948, DOI: 10.1002/ejic.200500165 *
WENDY FAN ET AL: "Alternating Stereospecific Copolymerization of Ethylene and Propylene with Metallocene Catalysts", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 123, no. 39, 1 October 2001 (2001-10-01), US, pages 9555 - 9563, XP055432372, ISSN: 0002-7863, DOI: 10.1021/ja0100773 *

Also Published As

Publication number Publication date
WO2018182982A2 (en) 2018-10-04

Similar Documents

Publication Publication Date Title
WO2018182982A3 (en) Metallocene-catalyzed polyalpha-olefins
MX2022003089A (en) Method to prepare ethylene copolymers.
WO2017048787A8 (en) Compositions and methods for selective olefin oligomerization comprising metal organic frameworks
WO2014160012A3 (en) Non-phthalate compounds as electron donors for polyolefin catalysts
WO2015105738A3 (en) Chromium (iii) catalyst systems with activator-supports
AR094324A1 (en) AN ETHYLENE BASED POLYMER
AR094323A1 (en) AN ETHYLENE BASED POLYMER
MX2017005536A (en) Airbag with individually tunable compartments.
EP4428234A3 (en) Direct-to-library methods, systems, and compositions
WO2016110699A3 (en) Sio2-layered double hydroxide microspheres and their use as catalyst supports in ethylene polymerisation
BR112014027931A8 (en) system and method for providing second-line service to a telecommunications device
MX2016008022A (en) Catalyst system for polymerisation of an olefin.
WO2019059846A3 (en) Modular construction system
WO2015090922A8 (en) A vulcanizable polymer composition
MX2017015580A (en) Processes for preparing metallocene-based catalyst systems in cyclohexene.
AU2015259566A8 (en) Systems and methods for handling and routing incoming communication requests
WO2018026406A8 (en) Unsaturated polyalpha-olefin materials
WO2019067274A8 (en) Bis-phenyl-phenoxy polyolefin catalysts having two methylenetrialkylsilicon ligands on the metal for improved solubility
WO2021050289A3 (en) Coded interleaved simultaneous source shooting
MX382272B (en) LAMINATED NOZZLE WITH THICK PLATE.
WO2017155719A3 (en) Multiple device and multiple line connected home and home monitoring
EP4438635A3 (en) Electron donors for ziegler-natta precatalyst preparation and catalyst system for olefin polymerization
Mühlherr et al. Intrinsic reflections in Coxeter systems
SA522432472B1 (en) Establishing polymerization
PH12017502168A1 (en) Fuel composition

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 18713559

Country of ref document: EP

Kind code of ref document: A2

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 2018713559

Country of ref document: EP

Effective date: 20191028