WO1998049208A1 - Nouveaux composes et leur utilisation dans un procede de polymerisation - Google Patents

Nouveaux composes et leur utilisation dans un procede de polymerisation Download PDF

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Publication number
WO1998049208A1
WO1998049208A1 PCT/GB1998/001205 GB9801205W WO9849208A1 WO 1998049208 A1 WO1998049208 A1 WO 1998049208A1 GB 9801205 W GB9801205 W GB 9801205W WO 9849208 A1 WO9849208 A1 WO 9849208A1
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Prior art keywords
hydrocarbyl
formula
polymerisation
hydrogen
complex
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PCT/GB1998/001205
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English (en)
Inventor
Philippe-Luc Bres
Vernon Charles Gibson
Christine Daniele Florence Mabille
Warren Reed
Duncan Wass
Richard Henry Weatherhead
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Bp Chemicals Limited
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Priority to AU70693/98A priority Critical patent/AU7069398A/en
Publication of WO1998049208A1 publication Critical patent/WO1998049208A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/04—Nickel compounds
    • C07F15/045—Nickel compounds without a metal-carbon linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/006—Palladium compounds
    • C07F15/0066—Palladium compounds without a metal-carbon linkage
    • 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
    • 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
    • C08F10/02—Ethene
    • 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
    • C08F110/02—Ethene

Definitions

  • the present invention relates to novel transition metal compounds and to their use as polymerisation catalysts.
  • Ziegler-Natta catalysts for example, those catalysts produced by activating titanium halides with organometallic compounds such as triethylaluminium, is fundamental to many commercial processes for manufacturing polyolefins. Over the last twenty or thirty years, advances in the technology have lead to the development of Ziegler-Natta catalysts which have such high activities that that olefin polymers and copolymers containing very low concentrations of residual catalyst can be produced directly in commercial polymerisation processes. The quantities of residual catalyst remaining in the produced polymer are so small as to render unnecessary their separation and removal for most commercial applications.
  • Such processes can be operated by polymerising the monomers in the gas phase, or in solution or in suspension in a liquid hydrocarbon diluent.
  • Polymerisation of the monomers can be carried out in the gas phase (the "gas phase process"), for example by fluidising under polymerisation conditions a bed comprising the target polyolefin powder and particles of the desired catalyst using a fluidising gas stream comprising the gaseous monomer.
  • the solution process the (co)polymerisation is conducted by introducing the monomer into a solution or suspension of the catalyst in a liquid hydrocarbon diluent under conditions of temperature and pressure such that the produced polyolefin forms as a solution in the hydrocarbon diluent.
  • the temperature, pressure and choice of diluent are such that the produced polymer forms as a suspension in the liquid hydrocarbon diluent.
  • These processes are generally operated at relatively low pressures (for example 10-50 bar) and low temperature (for example 50 to 150°C).
  • Commodity polyethylenes are commercially produced in a variety of different types and grades. Homopolymerisation of ethylene with transition metal based catalysts leads to the production of so-called "high density" grades of polyethylene. These polymers have relatively high stiffness and are useful for making articles where inherent rigidity is required. Copolymerisation of ethylene with higher 1-olefins (eg butene, hexene or octene) is employed commercially to provide a wide variety of copolymers differing in density and in other important physical properties. For example, copolymers made by copolymerising ethylene with higher 1 -olefins using transition metal based catalysts have a density in the range of 0.91 to 0.93.
  • 1-olefins eg butene, hexene or octene
  • linear low density polyethylene are in many respects similar to the so called “low density” polyethylene produced by the high pressure free radical catalysed polymerisation of ethylene.
  • Such polymers and copolymers are used extensively in the manufacture of flexible blown film.
  • WO 96/23010 discloses a process for the polymerization of olefins, comprising, contacting a transition metal complex of a bidentate ligand selected from the group consisting of, inter alia, R 2
  • the transition metal is selected from the group consisting of Ti, Zr, Sc, V, Cr, a rare earth metal, Fe, Co, Ni or Pd;
  • R 2 and R 5 are each independently hydrocarbyl or substituted hydrocarbyl, provided that the carbon atom bound to the imino nitrogen atom has at least two carbon atoms bound to it;
  • R 3 and R 4 are each independently hydrogen, hydrocarbyl, substituted hydrocarbyl, or R 3 and R 4 taken together are hydrocarbylene substituted hydrocarbylene to form a carbocyclic ring; and provided that: said transition metal also has bonded to it a ligand that may be displace by said olefin or add to said olefin.
  • An object of the present invention is to provide a novel catalyst suitable for polymerising olefins, and especially for polymerising ethylene alone or for copolymerising ethylene with higher 1 -olefins.
  • polymerisation is deemed to include any level of polymerisation from the production of low molecular weight products (eg dimers, trimers, tetramers, etc) through to ultra high molecular weight polymer.
  • a further object of the invention is to provide an improved process for the polymerisation of olefins, especially of ethylene alone or the copolymerisation of ethylene with higher 1 -olefins to provide homopolymers and copolymers having controllable molecular weights.
  • Catalysts of the present invention can be used to make linear polyethylene free from, or substantially free from, chain branching.
  • the present invention provides a nitrogen-containing metal complex compound having the general formula (Formula A):
  • Suitable sulphur- and/or oxygen-containing organic or inorganic groups are for example, SR, OSO 2 R, OSO 2 CF 3 , OCOR wherein R is a hydrocarbyl group, for example a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
  • R is a hydrocarbyl group, for example a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
  • each X is independently a univalent radical selected from halide, hydride, hydrocarbyloxide, amide, hydrocarbyl and substituted hydrocarbyl.
  • the two X's can if desired be linked together, for example, by a hydrocarbyl bridge.
  • the ring formed by Q, C 1 and N 1 can, for example, be a pyrazole, pyridine, pyrazine, pyrimidine, thiazole or pyridine ring system, or can form part of a polynuclear heterocyclic system such as, for example, quinoline or indazole.
  • the nitrogen-containing metal complex has the following formula (Formula Al) wherein the ring formed by Q, C and N 1 is a pyridine or substituted pyridine system;
  • R 1 , R 2 , R 3 and R 4 in the complex of Formula Al are preferably hydrogen or hydrocarbyl groups containing 1 to 10 carbon atoms. Two or more of the groups R 1 , R 2 , R 3 and R 4 can themselves be linked together to form a further ring or rings, for example a benzene ring. Examples of these R groups are methyl, ethyl, n- propyl, n-butyl, n-hexyl, and n-octyl. Most preferably R 1 , R 2 , R 3 and R 4 are all hydrogen atoms.
  • R 5 is preferably hydrogen or a hydrocarbyl or halohydrocarbyl group containing 1 to 10 carbon atoms.
  • R 6 is preferably a substituted or unsubstituted aromatic group, for example, phenyl, 1- naphthyl, 2-naphthyl, 2-ethylphenyl, 2,6-diisopropylphenyl, and 2,6-di-n- butylphenyl, 2,6-dimethylphenyl, 2-t-butylphenyl, 2,6-diphenylphenyl, 2,4,6- trimethylphenyl, 2,6-trifluoromethylphenyl, 4-bromo-2,6-dimethylphenyl, 3,5 dichloro2,6-diethylphenyl, and 2,6,bis(2,6-dimethylphenyl)phenyl.
  • the univalent radical X in the complex of Formula A and Formula Al is preferably selected from halogen and hydrocarbyl groups. Examples of such groups are chloro, bromo, methyl, ethyl, n-propyl, isopropyl, n-butyl and n-octyl.
  • Preferred novel compounds of Formula A of the present invention are the compounds having the structural formula (Formula B) as follows:
  • R 1 is hydrogen or methyl
  • X 1 and X 2 are the same or different and are chlorine, bromine or methyl
  • M is nickel or palladium
  • the present invention further provides a catalyst for the polymerisation of 1-olefins comprising (1) the compound of Formula A:
  • Suitable organoaluminium compounds include trialkyaluminium compounds, for example, trimethylaluminium, triethylaluminium, tributylaluminium, tri-n-octylaluminium, and diethylaluminium chloride.
  • Alumoxanes are well known in the art as typically the oligomeric compounds which can be prepared by the controlled addition of water to an alkylaluminium compound, for example trimethylaluminium. Such compounds can be linear, cyclic or mixtures thereof.
  • alumoxanes are generally believed to be mixtures of linear and cyclic compounds.
  • the cyclic alumoxanes can be represented by the formula [R 9 AlO] s and the linear alumoxanes by the formula R 10 (R U A1O) S wherein s is a number from about 2 to 50, and wherein R 9 , R 10 , and R 11 represent hydrocarbyl groups, preferably Ci to C ⁇ alkyl groups, for example methyl, ethyl or butyl groups.
  • fluorohydrocarbylboron compounds examples include dimethylphenylammonium tetra(pentafluorophenyl)borate, sodium tetrakis[(bis-3,5-trifluoromethyl)phenyl]borate, H + (OEt 2 )[(bis-3,5- trifluoromethyl)phenyl]borate, trityltetra(pentafluorophenyl)borate and tris(pentafluorophenyl) boron.
  • the quantity of activating compound selected from organoaluminium compounds, alumoxanes and fluorohydrocarbylboron compounds to be employed in the catalyst of the present invention is easily determined by simple testing, for example by the preparation of small test samples which can be used to polymerise small quantities of the monomer(s) and thus to determine the activity of the produced catalyst.
  • an alumoxane activator it is generally found that the quantity employed is sufficient to provide 1 to 20,000 atoms, preferably 1 to 2000 atoms of aluminium per Ni or Pd metal atom in the compound of Formula A.
  • the metal complexes of the present invention When the metal complexes of the present invention are activated to form a catalyst in accordance with the present invention using the compound H(Et 2 0) 2 B[3,5-C 6 H 3 (CF 3 ) 2 ] 4 it has been found that clearly defined catalytically active ionic species are produced. Accordingly the present invention further provides a catalytically active ionic species having the general formula:
  • R to R are as defined above, and X 3 is selected from hydrocarbyl groups, for example, methyl, ethyl, propyl or benzyl, and X 4 is selected from neutral electron donating ligands, for example ethers such as diethyl ether, nitriles such as acetonitrile.
  • ethers such as diethyl ether
  • nitriles such as acetonitrile.
  • Examples of particular catalytically active ionic species in accordance with the present invention include the following compounds (Formula CI and C2):
  • the catalyst of the present invention is preferably supported on a support material, for example, silica, alumina, zirconia, or on a polymer or a prepolymer, for example polyethylene or polystyrene. Formation of the supported catalyst can be achieved for example by treating the compound of Formula A with alumoxane in a suitable inert diluent, for example a volatile hydrocarbon, slurrying a particulate support material with the product and evaporating the volatile diluent.
  • a suitable inert diluent for example a volatile hydrocarbon
  • the quantity of support material employed can vary widely, for example from 100,000 to 1 grams per gram of metal present in the Formula A compound.
  • the present invention further provides a process for the polymerisation and copolymerisation of polymerisable monomeric material, preferably one or more 1- olefins, comprising contacting the monomeric material under polymerisation conditions with the catalyst of the present invention.
  • the polymerisation conditions can be, for example, solution phase, slurry phase or gas phase.
  • the catalyst can be used to polymerise ethylene under high pressure/high temperature process conditions wherein the polymeric material forms as a melt in supercritical ethylene.
  • the polymerisation is conducted under gas phase fluidised bed conditions.
  • Suitable monomers for use in the polymerisation process of the present invention are, for example, ethylene, propylene, butene, hexene, methyl methacrylate, methyl acrylate, butyl acrylate, acrylonitrile, vinyl acetate, and styrene.
  • Preferred monomers for homopolymerisation processes are ethylene and propylene.
  • the catalyst can be used for copolymerising ethylene with other 1 -olefins such as propylene, 1 -butene, 1 -hexene, 4-methylpentene-l, and octene.
  • the process can be operated, for example, in a vertical cylindrical reactor equipped with a perforated distribution plate to support the bed and to distribute the incoming fluidising gas stream through the bed.
  • the fluidising gas circulating through the bed serves to remove the heat of polymerisation from the bed and to supply monomer for polymerisation in the bed.
  • the fluidising gas generally comprises the monomer(s) normally together with some inert gas (eg nitrogen) and optionally with hydrogen as molecular weight modifier.
  • the hot fluidising gas emerging from the top of the bed is led optionally through a velocity reduction zone (this can be a cylindrical portion of the reactor having a wider diameter) and, if desired, a cyclone and or filters to disentrain fine solid particles from the gas stream.
  • the hot gas is then led to a heat exchanger to remove at least part of the heat of polymerisation.
  • Catalyst is preferably fed continuously or at regular intervals to the bed.
  • the bed comprises fluidisable polymer which is preferably similar to the target polymer.
  • Polymer is produced continuously within the bed by the polymerisation of the monomer(s).
  • Preferably means are provided to discharge polymer from the bed continuously or at regular intervals to maintain the fluidised bed at the desired height.
  • the process is generally operated at relatively low pressure, for example, at 10 to 50 bars, and at temperatures for example, between 50 and 120 °C.
  • the temperature of the bed is maintained below the sintering temperature of the fluidised polymer to avoid problems of agglomeration
  • Patent 5541270 which are hereby incorporated in this specification by reference. It is preferred to reintroduce the condensed liquid into the bed using the process described in our US Patent 5541270.
  • Examples 1 to 5 illustrate the preparation of novel nickel and palladium nitrogen-containing complex compounds in accordance with the present invention.
  • Examples 6 to 12 illustrate polymerisation of ethylene using catalysts prepared from these complexes.
  • Example 13 illustrates the preparation of two pyrazine complexes in accordance with the present invention and
  • Example 14 shows the polymerisation activity of these complexes. All manipulations of compounds sensitive to air and/or moisture were performed using a conventional vacuum/inert atmosphere (N 2 ) glove-box. All solvents employed were carefully dried using conventional techniques.
  • N 2 vacuum/inert atmosphere
  • metal complex compounds were prepared having the general formula: General Formula for Metal Complexes 1 to 5 prepared in Examples 1 to 5
  • M Ni
  • R 1 H
  • X 1 and X 2 are both Br.
  • the methylalumoxane solution is commercially available from Aldrich.
  • the produced catalyst solution was degassed under reduced pressure and back-filled with an atmosphere of ethylene. Fuming was observed and the solution became hot almost immediately. During the run time of 30 minutes the solution was left open to a supply of ethylene at one atmosphere and stirred vigorously at 25°C.
  • the polymerisation was terminated by the addition of dilute HC1 (ca.
  • Example 8 Polymerisation of ethylene using a catalyst prepared from Metal Complex-2 (see Example 2). Preparation of the catalyst and polymerisation of ethylene were carried out substantially as described in Example 6 except that the catalyst was prepared from Metal Complex-2 (5.0 mg, 0.01 mmol) and MAO solution (1.4 ml, 2.0 mmol, 200 equivalents). The run time of 30 minutes. Polyethylene was isolated as a viscous oil. Yield was 0.20 g. Activity was 41 g mmor'hr ⁇ bar "1 .
  • Example 8 Example 8
  • Acetonitrile (20 ml) was added to a mixture of Metal Complex-4 (0.10 g, 0.24 mmol) and NaB(3,5-C 6 H 3 (CF 3 ) 2 ) (0.21g, 0.24 mmol) at room temperature and stirred for about 20 minutes. After this time the solution was filtered and solvent removed under reduced pressure to yield a catalytically active yellow crystalline solid. Yield 0.25 g, 85 % of theoretical.
  • This catalyst (50 mg, 0.04 mmol) was used to polymerise ethylene substantially as described in Example 8, except that the run time was 18 hours at 25°C. Polyethylene was isolated as a free-flowing yellow oil. The yield was 0.24 g, corresponding to an activity of 0.3 g mmor'hr ⁇ bar "1 .
  • Example 10
  • Example 12 The polymerisation was carried out at 50°C under a pressure of 3 bar ethylene for lh50mins.
  • the polyethylene product was isolated and dried substantially as described in Example 6.
  • the yield of polyethylene was 0.10 gram.
  • the polyethylene was substantially linear as determined by NMR analysis (see foot of Table following Example 12).
  • Methyl magnesium bromide (0.5 ml of a 3.0 molar solution in diethylether, 1.5 mmol) was added dropwise to a stirred suspension of Metal Complex 13.1 (0.36g, 0.74 mmol) in Et 2 O at -30°C. This mixture was stirred for 2 hours during which time the solution was allowed to warm to 0°C. After this time the solution became a deep blue-green colour. 1,4-dioxane (5ml) was added and a fine precipitate formed. The solution was filtered and solvent removed under reduced pressure. The resultant solid was washed with three 10 ml aliquots of pentane to yield 0.18g (70% of theoretical) of Metal Complex- 13.2 as a fine dark green powder.
  • Et 2 O (ca. 10ml) was added to Metal Complex-13.2 (17.8mg, 0.05 mmol) and and H(Et 2 0) 2 B[3,5-C 6 H 3 (CF 3 ) 2 ] 4 (50.6 mg, 0.05 mmol) at 0°C in a Schlenk vessel. A dark red solution formed almost immediately which was stirred for ca. 5 minutes. After this time solvent was removed under reduced pressure to yield the active catalyst as a dark red solid. All of this dark red solid product (64 mg, 0.05 mmol assuming 100% yield was obtained) was dissolved in methylene chloride (ca. 30 ml). This solution was degassed under reduced pressure and back-filled with an atmosphere of ethylene.
  • Example 14 The Polymerisation Test of Example 14 was repeated using the Metal Complex- 13.1 instead of Metal Complex-13.2 and MAO activator instead of the fluorohydrocarbyl boron compound. Some polyethylene was produced, but this catalyst was considerably less active than that obtained using Metal Complex- 13.2.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

Abstract

L'invention concerne un composé de complexe métallique azoté possédant la formule (A) dans laquelle le noyau formé par Q, C1 et N1 est insaturé de manière aromatique, le groupe Q divalent comprenant une chaîne de 3 ou 4 atomes possédant la formule -[(CR)¿n?(Z)r]- de telle sorte que n désigne 2, 3, ou 4; r représente zéro ou 1; (n+r) = 3 ou 4; Z représente de l'azote, de l'oxygène ou du soufre; M représente du nickel ou du palladium; les groupes R peuvent représenter, par exemple, un hydrogène ou un hydrocarbyle; X représente un radical univalent, par exemple halide, hydride, hydrocarbyloxide; Q représente de préférence un noyau de pyridine. L'invention concerne également un catalyseur destiné à la polymérisation d'oléfines-1 comprenant le complexe métallique défini et une quantité d'activation d'un composé sélectionné dans le groupe formé par des composés d'organoaluminium, des alumoxanes et des composés de fluorohydrocarbylbore.
PCT/GB1998/001205 1997-04-25 1998-04-24 Nouveaux composes et leur utilisation dans un procede de polymerisation WO1998049208A1 (fr)

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AU70693/98A AU7069398A (en) 1997-04-25 1998-04-24 Novel compounds and their use in polymerisation

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GB9708487.5 1997-04-25
GBGB9708487.5A GB9708487D0 (en) 1997-04-25 1997-04-25 Novel catalysts for olefin polymerisation

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Cited By (108)

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EP4389776A1 (fr) 2022-12-20 2024-06-26 Borealis AG Procédé
WO2024133592A1 (fr) 2022-12-20 2024-06-27 Borealis Ag Processus de transition de catalyseur
WO2024133340A1 (fr) 2022-12-20 2024-06-27 Borealis Ag Processus
WO2024133044A1 (fr) 2022-12-23 2024-06-27 Borealis Ag Procédé de production d'un homo- ou d'un copolymère de polypropylène
WO2024133046A1 (fr) 2022-12-23 2024-06-27 Borealis Ag Processus de production d'un copolymère de polypropylène
WO2024133045A1 (fr) 2022-12-23 2024-06-27 Borealis Ag Procédé de production d'un homopolymère de polypropylène à haute fluidité

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