US20030176606A1 - Process for the production of highly reactive polyisobutenes - Google Patents

Process for the production of highly reactive polyisobutenes Download PDF

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Publication number
US20030176606A1
US20030176606A1 US10/385,556 US38555603A US2003176606A1 US 20030176606 A1 US20030176606 A1 US 20030176606A1 US 38555603 A US38555603 A US 38555603A US 2003176606 A1 US2003176606 A1 US 2003176606A1
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United States
Prior art keywords
process according
isobutene
polymerization
mol
highly reactive
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Abandoned
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US10/385,556
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English (en)
Inventor
Martin Bohnenpoll
Jurgen Ismeier
Oskar Nuyken
Mario Vierle
Dirk Schon
Fritz Kuhn
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Lanxess Deutschland GmbH
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Individual
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Assigned to BAYER AKTIENGESELLSCHAFT reassignment BAYER AKTIENGESELLSCHAFT ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KUEHN, FRITZ, NUYKEN, OSKAR, SCHOEN, DIRK KURT, VIERLE, MARIO, ISMEIER, JUERGEN, BOHNENPOLL, MARTIN
Publication of US20030176606A1 publication Critical patent/US20030176606A1/en
Priority to US11/397,104 priority Critical patent/US7291758B2/en
Assigned to LANXESS DEUTSCHLAND GMBH reassignment LANXESS DEUTSCHLAND GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BAYER AG
Abandoned legal-status Critical Current

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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
    • C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F10/04—Monomers containing three or four carbon atoms
    • C08F10/08—Butenes
    • C08F10/10—Isobutene
    • 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
    • C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F210/04—Monomers containing three or four carbon atoms
    • C08F210/08—Butenes
    • C08F210/10—Isobutene
    • C08F210/12—Isobutene with conjugated diolefins, e.g. butyl rubber
    • 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
    • C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
    • C08F236/08—Isoprene
    • 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
    • C08F110/04—Monomers containing three or four carbon atoms
    • C08F110/08—Butenes
    • C08F110/10—Isobutene
    • 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

Definitions

  • the present invention relates to a process for the production of highly reactive polyisobutenes with a content of terminal vinylidene groupings of greater than 80 mol % and an average molecular weight of 500 to 10,000 Dalton by cationic polymerization of isobutene, in the liquid phase, in the presence of monomeric, solvent-stabilized transition metal complexes with weakly coordinating anions.
  • Polyisobutenes with molecular weights of 500 to 5,000 Dalton are produced with the assistance of Lewis acid catalysts, such as aluminum chloride, aluminumalkyl chlorides or boron trifluoride and usually have less than 10 mol % of terminal double bonds (vinylidene groupings) and a molecular weight distribution (dispersity) of between 2 and 5.
  • Lewis acid catalysts such as aluminum chloride, aluminumalkyl chlorides or boron trifluoride and usually have less than 10 mol % of terminal double bonds (vinylidene groupings) and a molecular weight distribution (dispersity) of between 2 and 5.
  • terminal vinylidene groupings which react during adduct formation with maleic anhydride, whereas, depending upon their position, the double bonds located further within the macromolecules do not give rise to any or any distinctly lower conversion without the addition of halogens.
  • the proportion of terminal vinylidene groupings in the molecule is an important quality criterion for this type of polyisobutene.
  • polyisobutene products are obtained, the polyisobutene components of which, i.e. the polyisobutene macromolecules, have a random molecular weight distribution of a greater or lesser width.
  • the wider the molecular weight distribution of these polyisobutenes the greater the content thereof of polyisobutene macromolecules having relatively low or relatively high molecular weights, which are less suitable for the mentioned intended application.
  • reactive polyisobutenes comprising up to 88 wt. % of terminal double bonds can be obtained by boron trifluoride-catalyzed polymerization of isobutene at temperatures of ⁇ 50 to +30° C. and residence times of less than 10 minutes. A value of no lower than 1.8 is found for the dispersity of the polyisobutenes produced in this manner.
  • reaction temperatures of above 0° C. are disclosed in the above cited referenced and the Examples, therein only give rise to an elevated content of terminal double bonds of greater than 80% if temperatures of distinctly below 0° C. are used.
  • U.S. Pat. No. 4,227,027 discloses boron trifluoride-catalyzed alkyl transfer reactions, wherein the catalysts are adducts of boron trifluoride and diols or polyols at temperatures of 40 to 120° C.
  • the catalysts are adducts of boron trifluoride and diols or polyols at temperatures of 40 to 120° C.
  • Another process for the production of highly reactive polyisobutenes involves living cationic polymerization of isobutene with subsequent dehydrochlorination, as is described, for example, in U.S. Pat. No. 5,340,881. This process yields up to 100% of terminal double bonds, but requires low temperatures and a complex solvent mixture, which unnecessarily complicates recycling of the unreacted starting materials.
  • An object of the present invention was to develop an economic process, which operates at temperatures of above 0° C. and yields the described highly reactive polyisobutenes.
  • the present invention provides a process for the production of highly reactive isobutene homo- and copolymers with a content of terminal vinylidene groupings of greater than 80 mol % and an average molecular weight of 500 to 10,000 Dalton, wherein isobutene or isobutene with copolymerizable monomers is/are polymerize in the presence of a transition metal catalyst of the general formula
  • M is a metal from the 3rd to 12th periods of the periodic system of elements
  • R 1 is a C 1 -C 8 alkyl group
  • A is a weakly coordinating anion.
  • Copolymerizable monomers which may be used in the process of the present invention, include, for example, isoprene and/or styrene.
  • the process according to the present invention is preferably used to produce copolymers based on isobutene and isoprene, which have molecular weights from approximately 2,000 to 7,000 Dalton and have a content of incorporated isoprene of up to 60% (determined by nuclear magnetic resonance spectroscopy).
  • the highly reactive polyisobutenes produced according to the process of the present invention preferably have a content of terminal vinylidene groupings of 95 to 100 mol % and an average molecular weight of 2,000 to 7,000 Dalton.
  • the polyisoprenes according to the present invention are soluble in many organic solvents, such as chloroform, dichloromethane, hexane, heptane, cyclohexane, toluene or benzene or mixtures thereof.
  • the process of the present invention is preferably performed in an inert organic solvent, wherein halogenated and halogen-free hydrocarbons, which may optionally be substituted by nitro groups, or mixtures thereof are used.
  • halogenated and halogen-free hydrocarbons which may optionally be substituted by nitro groups, or mixtures thereof are used.
  • Dichloromethane, chloroform, dichloroethane, tetrachloroethane, hexane or pentane, and cycloalkanes, such as cyclohexane, and aromatic hydrocarbons, such as toluene and benzene, are, for example, preferred.
  • the quantity of solvent may be determined by routine experimentation.
  • the concentration of the introduced monomers in the solvent used is preferably in the range from 0.01 to 10 mol/l, more preferably 0.1 to 2 mol/l.
  • the transition metal catalysts of the above-stated general formula are those in which M is Mn, Ni, Cr or Zn and A contains anions of the formulae BF 4 ⁇ , SbX 6 ⁇ , PX 6 ⁇ and/or B(Ar) 4 ⁇ as well as B(Ar) 4 ⁇ anions bridged by cyclic groupings, wherein Ar denotes phenyl, which have 1 to 5 substituents, such as F, Cl or CF 3 .
  • Cyclic bridges which may preferably be considered for B (Ar) 4 ⁇ anions, include imidazolyl bridges.
  • R 1 preferably denotes C 1 -C 4 alkyl residues, such as methyl, ethyl, propyl, butyl, isopropyl, isobutyl or tert.-butyl.
  • More preferred transition metal catalysts include those of the following formulae:
  • the transition metal catalysts are used in the process according to the present invention in a molar ratio of 1:15,000,000 to 1:10, preferably of 1:500,000 to 1:10,000, relative to the introduced quantities of monomers.
  • the concentration of the introduced catalysts in the reaction mixture is in the range from 0.01 to 10 mmol/l, preferably 0.1 to 2 mmol/l.
  • Polymerization is performed according to the present invention at temperatures of approximately 0 to 100° C., preferably from 20 to 60° C.
  • transition metal catalysts useful according to the present invention are known per se and may be produced using known processes, as described, for example, in Wayne E. Buschmann, Joel S. Miller, Chem. Eur. J. 1998, 4(9), 1731-1737, and Bruce H. Lipshutz, Wayne Vaccaro, Bret Huft, Tetrahedron Letters 1986, 27(35), 4095-4098 and LaPointe, Robert E.; Roof, Gordon R.; Abboud, Khalil A.; Klosin, Jerzy. New Family of Weakly Coordinating Anions. Journal of the American Chemical Society (2000), 122(39), 9560-9561.
  • Molecular weight Mn was determined by means of gel permeation chromatography in chloroform. Column: Waters Ultrastyragel®, pore size 10,000 and 100,000 ⁇ and Waters Styragel®, pore size 500 ⁇ , detection: differential refractometer (Waters R 401), calibration: polystyrene standards.
  • Monomers gaseous at room temperature were advantageously dried by using columns packed with phosphorus pentoxide and finely divided potassium on aluminum oxide, while liquid monomers were dried by columns with aluminum oxide and distillation over sodium/aluminum oxide.
  • Halogenated solvents such as for example dichloromethane, were dried with calcium hydride and distilled under inert gas.
  • Aliphatic solvents such as for example hexane, were dried with sodium and distilled.
  • the content of terminal vinylidene end groups is 100 mol % according to 1 H-NMR.
  • the content of terminal vinylidene end groups is 100 mol % according to 1 H-NMR.
  • Isothermal polymerization of isobutene was performed at 40° C. in a polymerization autoclave.
  • the polymerization autoclave was heat treated and flooded with argon before the reaction.
  • 93 mL of dichloromethane were then introduced and adjusted to a temperature of 40° C.
  • Saturation proceeds at a stirring speed of 400 revolutions per minute, while polymerization was performed at a stirrer speed of 1,000 revolutions per minute.
  • the content of terminal vinylidene end groups was 100 mol % according to 1 H-NMR.

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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)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
  • Polymerization Catalysts (AREA)
US10/385,556 2002-03-15 2003-03-11 Process for the production of highly reactive polyisobutenes Abandoned US20030176606A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US11/397,104 US7291758B2 (en) 2002-03-15 2006-04-04 Process for the production of highly reactive polyisobutenes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10211418A DE10211418A1 (de) 2002-03-15 2002-03-15 Verfahren zur Herstellung hochreaktiver Polyisobutene
DE10211418.8 2002-03-15

Related Child Applications (1)

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US (2) US20030176606A1 (zh)
EP (1) EP1344785B1 (zh)
JP (1) JP4541652B2 (zh)
CN (1) CN1276931C (zh)
CA (1) CA2421688A1 (zh)
DE (2) DE10211418A1 (zh)
HK (1) HK1059445A1 (zh)
RU (1) RU2308462C2 (zh)

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US11155655B2 (en) 2018-03-21 2021-10-26 Lg Chem, Ltd. Organometal catalyst having cationic transition metal complex and borate-based bulky anion, method for preparing the same, and method for preparing oligomer using the same
US11370855B2 (en) 2018-07-27 2022-06-28 Lg Chem, Ltd. Method for preparing butene oligomer
US11414504B2 (en) 2018-03-21 2022-08-16 Lg Chem, Ltd. Method for preparing transition metal complex
US11578152B2 (en) 2018-04-05 2023-02-14 Lg Chem, Ltd. Cationic metal complex, organometal catalyst having borate-based bulky anion, method for preparing the same, and method for preparing oligomer or polymer using the same
US11987651B2 (en) 2019-08-26 2024-05-21 Lg Chem, Ltd. Catalyst composition and method for preparing hydrocarbon resin using the same

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CA2421688A1 (en) 2003-09-15
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JP2003277428A (ja) 2003-10-02
DE10211418A1 (de) 2003-09-25
US7291758B2 (en) 2007-11-06
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