N- Or P-containing Catalyst Patents (Class 585/527)
  • Patent number: 6900152
    Abstract: A catalyst used for trimerization of ethylene into 1-hexene is descrobed, which comprises (i) a specific organometallic complex having a neutral multidentate ligand having a tripod structure, (ii) an alkylaluminoxane, and an optional ingredient selected from: (iii) a halogenated inorganic compound, (iv) a specific alkyl group-containing compound, (v) a combination of a halogenated inorganic compound with a specific alkyl group-containing compound, (vi) an amine compound and/or an amide compound, and (vii) a combination of an amine compound and/or an amide compound with a specific alkyl group-containing compound.
    Type: Grant
    Filed: September 28, 2001
    Date of Patent: May 31, 2005
    Assignee: Tosoh Corporation
    Inventors: Toru Yoshida, Toshihide Yamamoto, Hisanori Okada, Hideyuki Murakita
  • Patent number: 6875900
    Abstract: An oligomerization process for the production of higher aliphatic olefins is disclosed. In the process, a liquid oligomerization feed stream comprising lighter aliphatic olefins is passed to a reactor vessel. The liquid oligomerization feed stream is transported upwardly in the reactor vessel against gravity through a fixed bed of solid oligomerization catalyst under oligomerization conditions. The catalyst has a Hammett acidity value of ?4 or less. A liquid oligomerization effluent stream is recovered comprising product higher aliphatic olefins.
    Type: Grant
    Filed: April 30, 2002
    Date of Patent: April 5, 2005
    Assignee: UOP LLC
    Inventor: William J. Koves
  • Publication number: 20040242947
    Abstract: The invention relates to a process 1-olefins b telomerization of compounds having conjugated double bonds with a telogen in the presence of a noble metal telomerization catalyst, hydrogenation of the telomer and cleavage of the hydrogenated intermediate. Use of he 1-olefin as comonomer.
    Type: Application
    Filed: March 19, 2004
    Publication date: December 2, 2004
    Inventors: Matthias Beller, Ralf Jackstell, Holger Klein, Dirk Rottger, Klaus-Diether Wiese, Dietrich Maschmeyer, Axel Tuchlenski, Alfred Kaizik, Silvia Santiago Fernandez
  • Publication number: 20040059170
    Abstract: The invention relates to a process for preparing 1-octene by reacting 1,3-butadiene with a telogen of the formula H—X—Y—H, where X is O, N, S or P and Y is C, N or Si and X and Y bear, depending on their valence, further substituents, in the presence of a telomerization catalyst to form a telomer of the formula H2C═CH—CH2—CH2—CH2—CH═CH—CH2—X—Y—H, partially hydrogenating the telomer to form a 1-substituted 2-octene of the formula H3C—CH2—CH2—CH2—CH2—CH═CH—CH2—X—Y—H and dissociating the 1-substituted 2-octene to give 1-octene.
    Type: Application
    Filed: August 8, 2003
    Publication date: March 25, 2004
    Inventors: Dirk Rottger, Axel Tuchlenski
  • Patent number: 6706657
    Abstract: A catalytic composition comprising at least one nickel compound mixed or complexed with at least one tertiary phosphine or a phosphite carrying a functional group, at least partly dissolved in a non-aqueous medium with an ionic nature resulting from bringing at least one aluminum halide into contact with at least one quaternary ammonium halide and/or at least one quaternary phosphonium halide, is useful for dimerizing, co-dimerizing and oligomerizing olefins. Functional groups include, but are not limited to, an amine, a cyclic amine, a nitrogen-containing heterocycle, an ester, an acid, an alcohol, a quaternary ammonium, a quaternary phosphonium, a sulfonium, a sulfonate or a phosphonate group.
    Type: Grant
    Filed: February 5, 2001
    Date of Patent: March 16, 2004
    Assignee: Institut Francais du Petrole
    Inventors: Dominique Commereuc, Dominique Le Pennec, Hélène Olivier-Bourbigou
  • Patent number: 6689928
    Abstract: The invention is a method and catalyst for selectively and efficiently producing short chain linear &agr;-olefins. The method includes contacting olefinic monomers under oligomerization conditions with the catalyst composition which comprises a composition prepared in situ by reacting a nickel compound selected from the group consisting of halides, hydrides, triflates, acetates, borates, C1, through C12 alkyl, C1 through C12 alkoxy, C3 through C12 cycloalkyl, C3 through C12 cycloalkoxy, aryl, thiolates, carbon monoxide, cyanate, olefins including diolefins and cycloolefins, and any other moiety into which a monomer can insert and mixtures thereof, with an amine ligand wherein said ligand is a nitrogen-containing ligand having one or more nitrogen atoms.
    Type: Grant
    Filed: September 25, 2001
    Date of Patent: February 10, 2004
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Robert Timothy Stibrany, Michael Gerard Matturro, Stephen Zushma, Abhimanyu Onkar Patil
  • Publication number: 20040015028
    Abstract: This invention is to a method of oligomerizing an olefin feed stream. The olefin feed stream contains at least one C2 to C12 olefin to obtain an olefin feed stream and has from about 1,000 ppm to about 10 percent by weight oxygenated hydrocarbon. The olefin is oligomerized by contacting with an acid based oligomerization catalyst.
    Type: Application
    Filed: July 22, 2002
    Publication date: January 22, 2004
    Inventors: Stephen Harold Brown, Georges M.K. Mathys
  • Patent number: 6667269
    Abstract: A catalytic composition for the dimerization, the codimerization or the oligomerization of olefins is obtained by bringing into contact at least one nickel compound that contains a heterocyclic carbene with at least one hydrocarbylaluminum halide and optionally at least one organic solvent. It is used in a process of dimerization, codimerization or oligomerization of olefins.
    Type: Grant
    Filed: March 23, 2001
    Date of Patent: December 23, 2003
    Assignee: Institut Francais du Petrole
    Inventors: Helene Olivier-Bourbigou, Dominique Commereuc, Stephane Harry
  • Publication number: 20030220512
    Abstract: The invention relates to novel transition metal complexes of the formula (I) 1
    Type: Application
    Filed: May 16, 2003
    Publication date: November 27, 2003
    Inventor: Siegfried Blechert
  • Patent number: 6653514
    Abstract: The invention pertains to a process of removing phosphorous-containing impurities and preferably also dienes, from an olefin stream using a sorbent selected from the group consisting of an acidic ion exchange resin, an acidic zeolite, an acidic alumina, a neutral alumina, and an activated carbon. The olefin stream preferably comprises primarily olefins having at least 6 carbon atoms.
    Type: Grant
    Filed: May 8, 2000
    Date of Patent: November 25, 2003
    Assignee: Shell Oil Company
    Inventors: Brendan Dermot Murray, David Michael Singleton, Zaida Diaz
  • Patent number: 6646173
    Abstract: A process is described for carrying out olefin oligomerisation in two catalysis steps of different types, using an organic feed containing at least one olefin. The cut to be treated, containing at least one olefin (Cn), is introduced into a first reaction zone where, in a first step, it undergoes catalytic oligomerisation either of the homogeneous liquid phase type, or of the heterogeneous type with a solid support. The effluent produced is generally sent to a heat exchanger traversed by a cold liquid, the effluent thus being cooled before being sent to a second reaction zone where it undergoes catalytic oligomerisation in a liquid—liquid two-phase medium, the invention being characterized in that at least an ethylenic hydrocarbon containing 3 to 5 carbon atoms per molecule is added to the inlet to the second reaction zone.
    Type: Grant
    Filed: October 26, 2001
    Date of Patent: November 11, 2003
    Assignee: Institut Francais du Petrole
    Inventors: Dominique Commereuc, Alain Forestiere, François Hugues, Hélène Olivier-Bourbigou
  • Patent number: 6635768
    Abstract: The invention relates to a complex of ruthenium of the structural formula I, where X1 and X2 are identical or different and are each an anionic ligand, R1 and R2 are identical or different and can also contain a ring, and R1 and R2 are each hydrogen or/and a hydrocarbon group, the ligand L1 is an N-heterocyclic carbene and the ligand L2 is an uncharged electron donor, in particular an N-heterocyclic carbene or an amine, imine, phosphine, phosphite, stibine, arsine, carbonyl compound, carboxyl compound, nitrile, alcohol, ether, thiol or thioether, where R1, R2, R3 and R4 are hydrogen or/and hydrocarbon groups.
    Type: Grant
    Filed: November 27, 2000
    Date of Patent: October 21, 2003
    Assignee: Degussa AG
    Inventors: Wolfgang Anton Herrmann, Wolfgang Schattenmann, Thomas Weskamp
  • Publication number: 20030181775
    Abstract: A catalyst composition for use in dimerizing, co-dimerizing or oligomerizing olefins results from dissolving a nickel compound, optionally mixed or complexed with a ligand, in a medium resulting from mixing:
    Type: Application
    Filed: February 3, 2003
    Publication date: September 25, 2003
    Applicant: Institut Francais du Petrole
    Inventors: Vincent Lecocq, Helene Olivier-Bourbigou
  • Patent number: 6602967
    Abstract: Deaminatively generated carbocations to initiate addition polymerization are disclosed. The high reactivity of the carbocation allows initiation of polymerization with virtually all alkenes, alkynes, alicyclic and aromatic monomers, regardless whether multisubstituted or conjugated. In addition, the carbocation initiates a polymerization reaction that generates an extremely high molecular weight polymer. In particular polystyrene of viscosity average molecular weight of approximately 106 was obtained.
    Type: Grant
    Filed: July 13, 2000
    Date of Patent: August 5, 2003
    Assignee: McNeese State University
    Inventors: Ron W. Darbeau, Mark S. Delaney, Ulku Ramelow
  • Publication number: 20030144514
    Abstract: Non-symmetrical ligands of formula (I); 1
    Type: Application
    Filed: December 16, 2002
    Publication date: July 31, 2003
    Inventors: Eric Johannes Maria De Boer, Henderikus Hyacinthus Deuling, Harry Van Der Heijden, Nicolaas Meijboom, Aart Bartus Van Oort, Arie Van Zon
  • Patent number: 6593505
    Abstract: A catalyst comprising A) a stationary acid component selected from the group consisting of a perfluorinated ion exchange polymer on an inert support, a silane modified perfluorosulfonic acid, and a sulfated metal oxide; and B) a mobile acid component selected from the group consisting of chlorosulfonic acid, fluorosulfonic acid, a fluorinated monosulfonic acid, a fluorinated sulfonimide, a fluorinated disulfonic acid, and an adjunct acid mixture is disclosed.
    Type: Grant
    Filed: January 13, 2003
    Date of Patent: July 15, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark A. Harmer, Eugene F. Hartstein
  • Publication number: 20030119921
    Abstract: Mixed bis-imine pyridine ligands of formula (I), wherein Z1, which is different from Z2, is an optionally substituted aryl group; and Z2 comprises an optionally substituted heterohydrocarbyl moiety, or an optionally substituted aryl group in combination with a metal, said optionally substituted aryl group being &pgr;-co-ordinated to the metal; 1
    Type: Application
    Filed: July 30, 2002
    Publication date: June 26, 2003
    Inventors: Eric Johannes Maria De Boer, Harry Van Der Heijden, Wilhelmina Cornelia Verhoef-Van Wijk, Arie Van Zon
  • Patent number: 6555723
    Abstract: A manufacturing process for &agr;-olefins using certain iron containing ethylene oligomerization catalysts together with alkylaluminum cocatalysts, in which using a low ratio of Al:Fe in the process results in a lowered formation of undesired polyethylene waxes and polymer. This results in less fouling of the process lines and vessels in the manufacturing plant.
    Type: Grant
    Filed: August 3, 2001
    Date of Patent: April 29, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Rinaldo S. Schiffino
  • Patent number: 6534691
    Abstract: An efficient manufacturing process for &agr;-olefins using certain iron containing ethylene oligomerization catalysts, comprises one or more liquid full reactors which are approximately at the bubble point of reacting ethylene, and optionally a final reactor which is at a lower pressure than the first reactor, both operating under other specified conditions. This process minimizes both the capital and operating costs for the plant. The &agr;-olefins produced are useful as monomers for polymers and as chemical intermediates, for example for making detergents.
    Type: Grant
    Filed: July 17, 2001
    Date of Patent: March 18, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: David A. Culver, Rinaldo S. Schiffino, Joel David Citron
  • Patent number: 6531555
    Abstract: This invention relates to a method to oligomerize ethylene comprising combining ethylene with a catalyst system comprising an activator and one or more phenoxide group metal compounds represented by the formula: wherein R3, R4, R5, R8, R9 and R10 may each independently be hydrogen, a halogen, a heteroatom containing group or a C1 to C100 group, provided that at least one of these groups has a Hammett &sgr;p value (Hansch, et al Chem. Rev. 1991, 91, 165) greater than 0.20; R2 and R7 may each independently be alkyl, aryl or silyl groups; R1 and R6 may each independently be an alkyl group, an aryl group, an alkoxy group, or an amino group; N is nitrogen; H is hydrogen; O is oxygen; M is a group 4 transition metal; and each X may each independently be an anionic ligand or a dianionic ligand.
    Type: Grant
    Filed: December 19, 2000
    Date of Patent: March 11, 2003
    Assignee: Univation Technologies, LLP
    Inventor: Gregory T. Whiteker
  • Publication number: 20030023123
    Abstract: Reaction mixtures and methods using catalysts and reaction conditions to produce significantly improved yields (and thereby higher purity) of olefin metathesis products, with greatly reduced amounts of impurities. These techniques include in one instance reduction in temperature of reaction, and in another, the use of chemical compounds that act as reaction inhibitors of unwanted reactions to minimize or prevent formation of unwanted impurities.
    Type: Application
    Filed: May 24, 2002
    Publication date: January 30, 2003
    Inventors: Basil P. Paulson, Richard L. Pederson
  • Patent number: 6501000
    Abstract: The invention is directed towards a composition comprising the formula LMX(X′)n wherein n equals 0 or 1; X and X′ are independently selected from the group consisting of halides, hydride, triflate, acetates, borates, C1 through C12 alkyl, C1 through C12 alkoxy, C3 through C12 cycloalkyl, C3 through C12 cycloalkoxy, aryl, thiolates, carbon monoxide, cyanate, olefins, and any other moiety into which a monomer can insert; M is selected from the group consisting of nickel, palladium, and platinum and L is a nitrogen-containing bidentate ligand with more than two nitrogen atoms. The composition possesses a tetrahedral or pseudo-tetrahedral structure. The invention also provides a method for using the composition in conjunction with an activating cocatalyst to form short chain &agr;-olefins.
    Type: Grant
    Filed: April 4, 2000
    Date of Patent: December 31, 2002
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Robert Timothy Stibrany, Michael Gerard Matturro, Stephen Zushma, Abhimanyu Onkar Patil
  • Patent number: 6501001
    Abstract: In order to carry out selective dimerization of propylene principally into branched dimers, a catalytic composition resulting from at least partly dissolving a nickel compound mixed or complexed with a tertiary phosphine carrying a functional group is used in a medium resulting from mixing at least one quaternary ammonium halide and/or at least one quaternary phosphonium halide, at least one aluminum halide and optionally at least one organometallic aluminum compound.
    Type: Grant
    Filed: February 5, 2001
    Date of Patent: December 31, 2002
    Assignee: Institut Francais du Petrole
    Inventors: Dominique Commereuc, Dominique Le Pennec, Hélène Olivier-Bourbigou
  • Patent number: 6459005
    Abstract: The present invention intends to provide an ethylene/&agr;-olefin copolymer of specific structure, exhibiting excellent performance as a lubricant oil additive, capable of having various functional groups in high ratio, and serviceable as raw material for various solubilizing agents. The ethylene/&agr;-olefin copolymer of the present invention is composed of ethylene and an &agr;-olefin having 3 to 10 carbon atoms, and characterized by specific characteristics.
    Type: Grant
    Filed: April 7, 2000
    Date of Patent: October 1, 2002
    Assignee: Mutsui Chemicals, Inc.
    Inventors: Hideki Hirano, Terunori Fujita, Junji Saito, Makoto Mitani
  • Patent number: 6444866
    Abstract: A process for oligomerising olefins in an organic feed containing at least one olefin comprises two steps with different types of catalysis. The cut to be treated containing at least one olefin (Cn) is introduced via line 1 into a reaction zone R1 where in a first step it undergoes catalytic oligomerisation, either of a liquid phase homogeneous type, or heterogeneous with a solid support. The effluent produced is sent via line 2 to a heat exchanger E1 traversed by a cold liquid. The effluent is thus cooled before being sent via line 3 to a second reaction zone R2 where it undergoes catalytic oligomerisation in a liquid-liquid two-phase medium. After reaction, the effluent is fed via line 4 to a zone L1 where it is washed. After washing, the hydrocarbon fraction is sent via line 5 to separator S1.
    Type: Grant
    Filed: July 6, 1998
    Date of Patent: September 3, 2002
    Assignee: Institut Francais du Petrole
    Inventors: Dominique Commereuc, Alain Forestiere, François Hughes, Hélène Olivier-Bourbigou
  • Patent number: 6417305
    Abstract: Ethylene is oligomerized with certain catalysts based on iron and cobalt complexes of 2,6-pyridinecarboxaldehydebis(imine) and 2,6-diacylpyridine-bis(imine) tridentate ligands.
    Type: Grant
    Filed: December 4, 2000
    Date of Patent: July 9, 2002
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Alison Margaret Anne Bennett
  • Patent number: 6399843
    Abstract: An oligomerization process for the production of higher aliphatic olefins is disclosed. In the process, a liquid oligomerization feed stream comprising lighter aliphatic olefins is passed to a reactor vessel. The liquid oligomerization feed stream is transported upwardly in the reactor vessel against gravity through a fixed bed of solid oligomerization catalyst under oligomerization conditions. The catalyst has a Hammett acidity value of −4 or less. A liquid saturate stream comprising paraffins is passed into contact with the feed stream and the catalyst. A liquid oligomerization effluent stream is recovered comprising the paraffins and product higher aliphatic olefins.
    Type: Grant
    Filed: October 12, 2000
    Date of Patent: June 4, 2002
    Assignee: UOP LLC
    Inventor: William J. Koves
  • Publication number: 20020052537
    Abstract: A process is described for carrying out olefin oligomerisation in two catalysis steps of different types, using an organic feed containing at least one olefin. The cut to be treated, containing at least one olefin (Cn), is introduced into a first reaction zone where, in a first step, it undergoes catalytic oligomerisation either of the homogeneous liquid phase type, or of the heterogeneous type with a solid support. The effluent produced is generally sent to a heat exchanger traversed by a cold liquid, the effluent thus being cooled before being sent to a second reaction zone where it undergoes catalytic oligomerisation in a liquid-liquid two-phase medium, the invention being characterized in that at least an ethylenic hydrocarbon containing 3 to 5 carbon atoms per molecule is added to the inlet to the second reaction zone.
    Type: Application
    Filed: October 26, 2001
    Publication date: May 2, 2002
    Applicant: Institut Francais du Petrole
    Inventors: Dominique Commereuc, Alain Forestiere, Francois Hugues, Helene Olivier-Bourbigou
  • Publication number: 20020045790
    Abstract: The invention is a method and catalyst for selectively and efficiently producing short chain linear &agr;-olefins. The method includes contacting olefinic monomers under oligomerization conditions with the catalyst composition which comprises a composition prepared in situ by reacting a nickel compound selected from the group consisting of halides, hydrides, triflates, acetates, borates, C1, through C12 alkyl, C1 through C12 alkoxy, C3 through C12 cycloalkyl, C3 through C12 cycloalkoxy, aryl, thiolates, carbon monoxide, cyanate, olefins including diolefins and cycloolefins, and any other moiety into which a monomer can insert and mixtures thereof, with an amine ligand wherein said ligand is a nitrogen-containing ligand having one or more nitrogen atoms.
    Type: Application
    Filed: September 25, 2001
    Publication date: April 18, 2002
    Inventors: Robert Timothy Stibrany, Michael Gerard Matturro, Stephen Zushma, Abhimanyu Onkar Patil
  • Publication number: 20020016521
    Abstract: An efficient manufacturing process for &agr;-olefins using certain iron containing ethylene oligomerization catalysts, comprises one or more liquid full reactors which are approximately at the bubble point of reacting ethylene, and optionally a final reactor which is at a lower pressure than the first reactor, both operating under other specified conditions. This process minimizes both the capital and operating costs for the plant. The &agr;-olefins produced are useful as monomers for polymers and as chemical intermediates, for example for making detergents.
    Type: Application
    Filed: July 17, 2001
    Publication date: February 7, 2002
    Inventors: David A. Culver, Rinaldo S. Schiffino, Joel David Citron
  • Patent number: 6335473
    Abstract: A process for oligomerization of C4 and C5 isoolefins or the etherification thereof with C1 to C6 alcohols wherein the reactants are contacted first in a partial liquid phase reactor (boiling point reactor) with a fixed bed acid cation exchange resin catalyst at an LHSV of 5 to 20, pressure of 0 to 400 psig and temperature of 120 to 300° F., at a pressure to maintain the reaction mixture at its boiling point whereby at least a portion but less than all of the reaction mixture is vaporized and the entire reaction stream is directed to a catalytic distillation column reactor for further reaction of the reactants, where the improvement is having a decoupling drum between the boiling point reactor and the catalytic distillation column reactor. The addition of a decoupler drum allows the reactors to operate at a pressure independent of each other.
    Type: Grant
    Filed: September 8, 2000
    Date of Patent: January 1, 2002
    Assignee: Catalytic Distillation Technologies
    Inventors: Amarjit S. Bakshi, Timothy P. McGuirk, J. C. Gupta, Thomas Koval
  • Patent number: 6284937
    Abstract: A process for carrying out a reaction on an organic feed, for example dimerization, co-dimerization, oligomerization or metathesis of olefins, as described in which the catalyst is a catalytic metal compound dissolved in a non-aqueous ionic medium which is not or is only slightly miscible with hydrocarbons. The reaction is carried out in a system comprising at least two treatment loops each comprising at least one reaction zone and at least one zone for separating the organic and polar phases between which the polar medium containing the catalytic metal compound, and the organic phase circulate. Fresh polar phase is injected into the second loop and used polar phase is eliminated from the first loop. The hydrocarbon to be transformed is injected into the first loop and the products are withdrawn from the second loop. The invention also concerns a unit for carrying out the process.
    Type: Grant
    Filed: May 27, 1998
    Date of Patent: September 4, 2001
    Assignee: Institut Francais du Petrole
    Inventors: Helene Olivier, Dominique Commereuc, Alain Forestiere, Francois Hugues
  • Patent number: 6184428
    Abstract: A catalyst and a process are provided for oligomerizing ethylene. A heterogeneous catalyst system comprises: (1) a chelating ligand, preferably 2-diphenyl phosphino benzoic acid (DPPBA); (2) a nickel precursor, preferably nickel chloride hexahydrate (NiCl2.6H2O); (3) a catalyst activator, preferably sodium tetraphenylborate (NaBPh4); and (4) silica. A 1:1:1 molar ratio of Ni:DPPBA:BPh4 catalyst components are fixed on a silica support using low-temperature fixation. The catalyst components are dispersed in a diluent, preferably ethanol, and silica is added. The ethanol is evaporated using freeze-drying equipment to form a silica-supported catalyst system. The silica-supported catalyst is slurried in ethanol in a reactor, and ethylene is added. The reactor pressure and temperature are maintained at about 725 psig and 100° C., respectively, for about two hours.
    Type: Grant
    Filed: February 17, 1999
    Date of Patent: February 6, 2001
    Assignee: Saudi Basic Industries Corporation
    Inventors: Mohammad Akhtar Zahoor, Fahad Al-Sherehy, Olagoke Olabisi, Mohammed M. Abdillahi, Mian Rahat Saeed
  • Patent number: 6133495
    Abstract: A process for producing an .alpha.-olefin oligomer, comprising subjecting an .alpha.-olefin to oligomerization in a reaction solution containing a chromium-based catalyst produced by bringing at least a chromium compound (a), a pyrrole ring-containing compound (b), an alkyl aluminum compound (c) and a halogen-containing compound (d) into contact with each other, wherein the chromium-based catalyst is a catalyst produced by bringing the pyrrole ring-containing compound (b), the alkyl aluminum compound (c) and the halogen-containing compound (d) into contact with each other in a hydrocarbon and/or halogenated hydrocarbon solvent, and then bringing the resultant mixed solution into contact with the chromium compound (a); or a catalyst produced by bringing the chromium compound (a), the pyrrole ring-containing compound (b), the alkyl aluminum compound (c) and the halogen-containing compound (d) into contact with each other in a hydrocarbon and/or halogenated hydrocarbon solvent in the absence of .alpha.
    Type: Grant
    Filed: January 2, 1998
    Date of Patent: October 17, 2000
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hisao Urata, Takayuki Aoshima, Sugio Nishimura
  • Patent number: 6127301
    Abstract: The present invention provides a novel catalyst system which can be preferably used in the trimerization, oligomerization reaction or polymerization reaction of an olefin, and a method for the trimerization, oligomerization or polymerization reaction of an olefin, which comprises using the catalyst system. A catalyst system obtained by contacting the following components (A) to (C):(A) a chromium compound,(B) an imine compound, and(C) a metal alkyl compound, and a method for the trimerization, oligomerization or polymerization reaction of an olefin, which comprises using the catalyst system are disclosed.
    Type: Grant
    Filed: June 27, 1997
    Date of Patent: October 3, 2000
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kiyoshi Iwanaga, Mitsuhisa Tamura
  • Patent number: 6103946
    Abstract: Alpha-olefins are manufactured in high yield and with very high selectivity by contacting ethylene with an iron complex of a selected 2,6-pyridinedicarboxaldehyde bisimine or a selected 2,6-diacylpyridine bisimine, and in some cases a selected activator compound such as an alkyl aluminum compound. Novel bisimines and their iron complexes are also disclosed. The .alpha.-olefins are useful as monomers and chemical intermediates.
    Type: Grant
    Filed: January 12, 1998
    Date of Patent: August 15, 2000
    Assignees: E. I. du Pont de Nemours and Company, University of North Carolina
    Inventors: Maurice S. Brookhart, III, Brooke L. Small
  • Patent number: 6080826
    Abstract: Functionalized cyclic olefins and methods for making the same are disclosed. Methods include template-directed ring-closing metathesis ("RCM") of functionalized acyclic dienes and template-directed depolymerization of functionalized polymers possessing regularly spaced sites of unsaturation. Although the template species may be any anion, cation, or dipolar compound, cationic species, especially alkali metals, are preferred. Functionalized polymers with regularly spaced sites of unsaturation and methods for making the same are also disclosed. One method for synthesizing these polymers is by ring-opening metathesis polymerization ("ROMP") of functionalized cyclic olefins. The metathesis catalysts for both RCM and ROMP reaction are ruthenium or osmium carbene complex catalysts of the formula ##STR1## where M is Os or Ru; R and R.sup.1 each may be hydrogen, C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, C.sub.1 -C.sub.20 alkyl, aryl, C.sub.1 -C.sub.20 carboxylate, C.sub.1 -C.sub.20 alkoxy, C.sub.2 -C.sub.
    Type: Grant
    Filed: December 18, 1997
    Date of Patent: June 27, 2000
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Michael J. Marsella, Heather D. Maynard
  • Patent number: 6063881
    Abstract: Propylene may be oligomerized by contact with cobalt complexes corresponding to the following structure: ##STR1## wherein R.sup.1 -R.sup.7 are hydrogen, hydrocarbyl or inert functional groups, and X is an anion. The resulting olefins are useful as chemical intermediates.
    Type: Grant
    Filed: April 2, 1998
    Date of Patent: May 16, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Alison Margaret Anne Bennett
  • Patent number: 6043401
    Abstract: Catalysts and processes are described to make low molecular weight, essentially terminally-unsaturated, viscous poly(1-olefin) or copoly(1-olefin) having a high terminal vinylidine content from a feed stock containing one or more 1-olefin and other volatile hydrocarbon liquids using a Ziegler catalyst made from a Group IVb metallocene and an aluminoxane cocatalyst, particularly bis(cyclopentadienyl) and bis(indenyl) titanium(IV), zirconium(IV) or hafnium(IV) compounds and methylaluminoxane. A particularly useful feed stock is a refinery stream containing 1-olefins and isobutylene which is used to make polyisobutylene.
    Type: Grant
    Filed: January 15, 1998
    Date of Patent: March 28, 2000
    Assignee: BP Amoco Corporation
    Inventors: Vahid Bagheri, Bruce Edward Firth, Frank Calabrese, Robert Scott Hensey
  • Patent number: 6025534
    Abstract: A method is provided for regenerating a fixed bed of olefin polymerization catalyst which can be performed without taking the catalyst bed out of service. The method involves the use of two different olefin-containing feedstocks, wherein the first feedstock is a conventional olefin-containing feedstock which contains little if any content of aromatic compounds. The second feedstock contains a significant concentration of aromatic compounds. In the practice of the invention, the second feedstock is substituted for the first feedstock whenever catalyst regeneration is deemed appropriate, and the flow of the second feedstock to the catalyst bed is continued for a period of time which is effective to at least partially regenerate the catalyst.
    Type: Grant
    Filed: April 7, 1998
    Date of Patent: February 15, 2000
    Assignee: BP Amoco Corporation
    Inventors: Anthony M. Valente, David B. Johnson, George A. Huff, Jr., Robert L. Mehlberg
  • Patent number: 6013850
    Abstract: A process to maximize the production of low molecular weight alpha olefins from ethylene is disclosed. The process comprises oligomerizing ethylene in the presence of a catalyst, of titanium aryloxide and/or titanium alkoxide; alkyl aluminum halide and triaryl phosphine and/or trialkyl phosphine in the temperature range of 80.degree. C. to 110.degree. C. at substantially low pressures of from 60 to 150 psi. A continuous supply of ethylene is maintained.
    Type: Grant
    Filed: April 8, 1997
    Date of Patent: January 11, 2000
    Assignee: Indian Petrochemicals Corporation Limited
    Inventors: G. L. Tembe, S. Muthukumaru Pillai, Sheo Satish, M. Ravindranathan
  • Patent number: 5962761
    Abstract: A process for the continuous oligomerization of ethylene to produce linear alpha olefins by oligomerizing ethylene in a polar phase comprising a solution of transition metal catalyst system at oligomerization conditions including a temperature and pressure greater than the critical temperature and pressure of ethylene. The resulting hydrocarbon phase containing oligomers and unreacted ethylene is subjected to physical treatment which tends to render the ethylene a nonsolvent for oligomers and thereby produce a liquid stream rich in unreacted ethylene which may be recycled to the oligomerization reaction zone by pumping.
    Type: Grant
    Filed: October 15, 1998
    Date of Patent: October 5, 1999
    Assignee: Uop LLC
    Inventors: Paul A. Sechrist, Brian H. Johnson
  • Patent number: 5945575
    Abstract: A process for the preparation of halogen-free, reactive polyisobutene having a content of terminal double bonds of more than 50 mol % and an average molecular weight M.sub.n of from 500 to 5000 dalton by the cationic polymerization of isobutene or isobutene-containing hydrocarbon mixtures in the liquid phase, wherein the polymerization is carried out at a temperature of from -30.degree. to +40.degree. C. over a heterogeneous polymerization catalyst containing at least one element acting as promoter and selected from Group IB, Group IIB, Group IIIB, Group IVB, Group VB, Group VIIB, or Group VIIIB of the Periodic Table or from Group IIA, Group IIIA, Group IVA, Group VA, or Group VIA of the Periodic Table or a number of said elements in each case in the form of an oxygen-containing compound and zirconium in the form of an oxygen-containing compound, said polymerization catalyst containing no industrially effective amounts of halogens.
    Type: Grant
    Filed: January 27, 1998
    Date of Patent: August 31, 1999
    Inventors: Christoph Sigwart, Eugen Gehrer, Ulrich Muller, Hans Peter Rath, Rolf Fischer
  • Patent number: 5932778
    Abstract: A method is provided which can be used to quickly and easily take a fixed-bed of solid acid olefin polymerization catalyst out of service without causing any significant catalyst deactivation. The method involves substituting a substantially olefin-free hydrocarbon fluid for at least a portion of the olefin-containing feedstock to the polymerization process, wherein the substantially olefin-free hydrocarbon fluid boils within the range from about 20.degree. to about 250.degree. C. and contains at least about 5 vol. % aromatics.
    Type: Grant
    Filed: September 30, 1997
    Date of Patent: August 3, 1999
    Assignee: BP Amoco Corporation
    Inventors: Anthony M. Valente, David B. Johnson, George A. Huff, Jr.
  • Patent number: 5929297
    Abstract: Alpha-olefin oligomers are produced by oligomering alpha-olefin monomer with a catalyst system comprising boron trifluoride, a protic promoter, and a special type of modifier. The modifier is a compound that satisfies the following criteria: (a) it has at least one moiety in which a carbonyl group is directly bonded to a nitrogen atom which is in turn bonded to two separate carbon atoms, (b) it is devoid of any nitrogen atom other than a nitrogen atom that is either (i) directly bonded to two separate carbon atoms and to a carbonyl group or (ii) is triply bonded to a single carbon atom, and (c) it is devoid of any protonic functional substituent. These modifiers control the oligomer product distribution and provide higher percentages of lower oligomers, especially dimers.
    Type: Grant
    Filed: September 25, 1997
    Date of Patent: July 27, 1999
    Assignee: BP Amoco Corporation
    Inventors: Kevin J. Theriot, Robert G. Irwin
  • Patent number: 5910619
    Abstract: The disclosure described a process for producing an .alpha.-olefin oligomer, which comprises carrying out oligomerization of an .alpha.-olefin in a solvent in the presence of a catalytically effective amount of a chromium-based catalyst system composed of a combination of at least (a) a chromium compound, (b) a nitrogen-containing compound of at least one selected from the group consisting of an amine, an amide and an imide, (c) an alkylaluminum compound and (d) a halogen-containing compound,wherein each of the .alpha.-olefin, the chromium compound (a), the nitrogen-containing compound (b) of at least one selected from the group consisting of an amine, an amide and an imide, the alkylaluminum compound (c) and the halogen-containing compound (d) is supplied to a reaction system in a mode that the chromium compound (a) and the alkylaluminum compound (c) do not contact each other before each of said compounds (a) to (d) and the .alpha.-olefin coexists in the reaction solvent and the oligomerization of an .alpha.
    Type: Grant
    Filed: June 20, 1995
    Date of Patent: June 8, 1999
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hisao Urata, Takayuki Aoshima, Toshiyuki Oshiki, Jun Takahara, Shinji Iwade, Yoshiaki Nanba, Yoshitaka Araki, Hirofumi Nakamura, Takeshi Okano
  • Patent number: 5880323
    Abstract: Disclosed herein are processes for polymerizing ethylene, acyclic olefins, and/or selected cyclic olefins, and optionally selected olefinic esters or carboxylic acids, and other monomers. The polymerizations are catalyzed by selected transition metal compounds, and sometimes other co-catalysts. Since some of the polymerizations exhibit some characteristics of living polymerizations, block copolymers can be readily made. Many of the polymers produced are often novel, particularly in regard to their microstructure, which gives some of them unusual properties. Numerous novel catalysts are disclosed, as well as some novel processes for making them. The polymers made are useful as elastomers, molding resins, in adhesives, etc. Also described herein is the synthesis of linear .alpha.-olefins by the oligomerization of ethylene using as a catalyst system a combination a nickel compound having a selected .alpha.-diimine ligand and a selected Lewis or Bronsted acid, or by contacting selected .alpha.
    Type: Grant
    Filed: July 10, 1997
    Date of Patent: March 9, 1999
    Assignees: E. I. du Pont de Nemours and Company, University of North Carolina
    Inventors: Maurice S. Brookhart, III, Lynda Kaye Johnson, Christopher Moore Killian, Lin Wang, Zhen-Yu Yang
  • Patent number: 5856612
    Abstract: The present invention relates to a process for producing an .alpha.-olefin oligomer by subjecting .alpha.-olefin to oligomerization in a reaction zone in the presence of a reaction solution containing a chromium-based catalyst, which comprises,continuously conducting said oligomerization of .alpha.-olefin by using said chromium-based catalyst comprising at least a chromium compound (a), a nitrogen-containing compound (b) selected from the group consisting of amines, amides and imides, and an alkyl aluminum compound (c) while maintaining a molar ratio of the .alpha.-olefin oligomer to .alpha.-olefin in the range of 0.05 to 1.00.
    Type: Grant
    Filed: January 29, 1997
    Date of Patent: January 5, 1999
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Yoshitaka Araki, Hirofumi Nakamura, Yoshiaki Nanba, Takeshi Okano
  • Patent number: 5817905
    Abstract: The invention concerns an improved process for the conversion of ethylene into light alpha olefins wherein the ethylene is brought into contact with a catalyst obtained by mixing a compound of zirconium with an organic compound selected from the class of acetals and ketals, esters, ketones, ethers, amines, nitrites, anhydrides, chlorides of acids, amides, aldehydes, thioethers, sulphides and disulphides, thiophenes, thioureas and phosphines, and with a chloro or bromo compound of aluminium hydrocarbyl, in the presence of an additive formed by at least one quaternary ammonium salt.
    Type: Grant
    Filed: April 24, 1997
    Date of Patent: October 6, 1998
    Assignee: Institut Francais du Petrole
    Inventors: Dominique Commereuc, Yves Glaize, Fran.cedilla.ois Hugues, Pierre Panzarella, Lucien Saussine
  • Patent number: 5811618
    Abstract: Ethylene is trimerized to form 1-hexene by using a catalyst comprising an aluminoxane and polydentate phosphine, arsine, and/or stibine coordination complex of a chromium salt. Catalysts, complexes, and ligands enabling production of 1-hexene in extremely high yields and purity are also described.
    Type: Grant
    Filed: August 25, 1995
    Date of Patent: September 22, 1998
    Assignee: Amoco Corporation
    Inventor: Feng-Jung Wu