Using Catalyst Containing Metal Bonded To Or Complexed With C, C-containing Compound, Or H Patents (Class 585/511)
  • Publication number: 20010047121
    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: Application
    Filed: March 23, 2001
    Publication date: November 29, 2001
    Applicant: INSTITUT FRANCAIS DU PETROLE
    Inventors: Helene Olivier-Bourbigou, Dominique Commereuc, Stephane Harry
  • Patent number: 6291733
    Abstract: A method of dimerizing alpha-olefins to mostly linear internal olefin dimers using as a catalyst a transition metal complex with an activating co-catalyst.
    Type: Grant
    Filed: June 2, 1999
    Date of Patent: September 18, 2001
    Assignee: Chevron Chemical Company LLC
    Inventors: Brooke L. Small, Eduardo J. Baralt, A. J. Marcucci
  • Publication number: 20010018546
    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: Application
    Filed: February 5, 2001
    Publication date: August 30, 2001
    Inventors: Dominique Commereuc, Dominique Le Pennec, Helene Olivier-Bourbigou
  • Patent number: 6281401
    Abstract: A process for oligomerizing at least one heavy olefin having at least 5 carbon atoms per molecule in the presence of at least one co-fed light olefin having less than 5 carbon atoms per molecule is disclosed. The presence of the at least one co-fed light olefin results in increased C6=(C6 olefin) conversion (if present as one of the at least one heavy olefins), increased weight % of C11+ hydrocarbons in the C9+ material of the product and increased cetane of the C9+ material of the product as compared to the oligomerization of the at least one heavy olefin without the co-fed at least one light olefin.
    Type: Grant
    Filed: September 16, 1999
    Date of Patent: August 28, 2001
    Assignee: Phillips Petroleum Company
    Inventor: Bruce B. Randolph
  • Patent number: 6235956
    Abstract: An acetal, wherein the acetal is 2,2-di(tetrahydrofurfuryloxy)propane as well as processed for producing the acetal and methods of using the acetal.
    Type: Grant
    Filed: December 22, 1998
    Date of Patent: May 22, 2001
    Assignee: Institut Francais du Petrole
    Inventors: François Hugues, Alain Forestiere, Lucien Saussine, Dominique Commereuc
  • Patent number: 6177603
    Abstract: The instant invention provides a process for substantially reducing the polymer cement viscosity or reducing the molecular weight distribution of the a conjugated diene polymer synthesized by using a charge of catalytically effective amounts of a rare earth catalyst and an organo magnesium component by adding an organo zinc component to the charge in an amount and under conditions sufficient to reduce the polymer cement viscosity. The invention also contemplates a catalyst compostion for substantially reducing the polymer cement viscosity of a polymer product as well the resultant polymer product.
    Type: Grant
    Filed: June 12, 1998
    Date of Patent: January 23, 2001
    Assignee: Bridgestone Corporation
    Inventor: Thomas J. Lynch
  • Patent number: 6153807
    Abstract: A copolymer of ethylene and an alpha-olefin having an ethylene content of from 30 to 90 mole %, a number average molecular weight of from 300 to 30,000 and a molecular weight distribution defined by a Q value (the ratio of the weight average molecular weight to the number average molecular weight of not more than 3 and a Z value (the ratio of the maximum value of the molecular weight to the minimum value of the molecular weight when the molecular weight is measured by gel permeation chromatography) of from 15 to 200. The said copolymer can be produced by a process comprising copolymerizing ethylene with an alpha-olefin in the liquid phase in the presence of a polymerization catalyst composed of a combination of a soluble vanadium compound and an organoaluminum compound in the co-presence of hydrogen, characterized in that(a) the copolymerization is carried out in a continuous manner,(b) the concentration of the vanadium compound in the polymerization system is maintained at 0.
    Type: Grant
    Filed: July 14, 1993
    Date of Patent: November 28, 2000
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Hidekuni Oda, Tatuo Kinoshita, Akiyoshi Shimizu
  • Patent number: 6121502
    Abstract: A process for the manufacture of linear alpha-olefins is disclosed. The process employs, for the purposes of oligomerizing an unsaturated aliphatic hydrocarbon to linear alpha-olefins, a catalyst mixture comprising titanium aryl and/or titanium alkoxide, organoaluminum halide and optionally one or more additives selected from a group containing phosphorus, oxygen and sulphur compounds.
    Type: Grant
    Filed: February 19, 1997
    Date of Patent: September 19, 2000
    Assignee: Indian Petrochemicals Corporation Limited
    Inventors: Gopal Laxman Tembe, Ashis Ranjan Bandyopadhyay, S. Muthukumaru Pillai, Sheo Satish, M. Ravindranathan
  • Patent number: 6080902
    Abstract: The present invention relates to a method of using polyolefin waxes prepared by means of metallocene catalysts as additive components in printing inks and surface coatings.
    Type: Grant
    Filed: July 10, 1998
    Date of Patent: June 27, 2000
    Assignee: Clariant GmbH
    Inventors: Hans-Friedrich Herrmann, Gerd Hohner
  • Patent number: 6031145
    Abstract: A catalyst composition for a process of oligomerising ethylene to produce 1-butene and/or 1-hexene wherein the catalytic composition is obtained by mixing at least one chromium compound with at least one aryloxy aluminum compound with general formula R.sub.n Al(R'O).sub.3-n where R is a linear or branched hydrocarbyl radical containing 1 to 30 carbon atoms, R'O is an aryloxy radical containing 6 to 80 carbon atoms and n is a whole number which can take the values 0, 1 or 2, and with at least one other hydrocarbyl aluminum compound selected from tris(hydrocarbyl)aluminum compounds or chlorinated or brominated hydrocarbyl aluminum compounds.
    Type: Grant
    Filed: June 17, 1998
    Date of Patent: February 29, 2000
    Assignee: Institut Francais du Petrole
    Inventors: Dominique Commereuc, Sebastien Drochon, Lucien Saussine
  • 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: 6005151
    Abstract: The invention relates to a process for preparing monofunctional, bifunctional or polyfunctional aromatic olefins of the formula (I) ##STR1## wherein a palladium compound of the formula (IV) ##STR2## is used as a catalyst in the preparation of the compounds of the formula (I).
    Type: Grant
    Filed: January 30, 1996
    Date of Patent: December 21, 1999
    Assignee: Aventis
    Inventors: Wolfgang Anton Herrmann, Matthias Beller, Ahmed Tafesh
  • Patent number: 5945574
    Abstract: The use of novel heterogeneous catalyst complexes as catalysts for oligomerizing alpha-olefins is disclosed. The complexes are formed from (i) a solid olefin polymer having a linear backbone and a plurality of pendant omega-hydroxyalkyl groups, (ii) an organomagnesium halide, and (iii) a boron trihalide, preferably BF.sub.3. The complexes can be recovered and reused repeatedly in batch-type operations and can be used for long periods of time in continuous or semi-continuous operations without replenishment of their boron trifluoride content.
    Type: Grant
    Filed: December 13, 1995
    Date of Patent: August 31, 1999
    Assignee: BP Amoco Corporation
    Inventors: Tze-Chiang Chung, Ruidong Ding, Ronald L. Shubkin
  • Patent number: 5919996
    Abstract: A process is provided to modify an olefin production catalyst system which comprises contacting an olefin production catalyst system with ethylene prior to use. A process also is provided to trimerize and/or oligomerize olefins with the novel, modified olefin catalyst production system. The modified olefin production catalyst system produces less solids, such as, for example, polymer.
    Type: Grant
    Filed: October 13, 1998
    Date of Patent: July 6, 1999
    Assignee: Phillips Petroleum Company
    Inventors: Jeffrey W. Freeman, John L. Buster, Ronald D. Knudsen
  • Patent number: 5908903
    Abstract: Catalyst systems which are suitable for polymerizing olefinically unsaturated compounds comprise as active constituentsA) a metallocene complex of the metals of the fourth, fifth or sixth transition group of the Periodic Table of the Elements,B) a compound forming metallocenium ions andC) a sterically hindered, organic Lewis base.
    Type: Grant
    Filed: December 20, 1996
    Date of Patent: June 1, 1999
    Assignee: BASF Aktiengesellschaft
    Inventor: Joachim Rosch
  • Patent number: 5900521
    Abstract: Catalysts for preparing ethylene by conversion of methane or purified natural gas and preparation thereof, and process for preparation of ethylene by direct conversion of methane or purified natural gas using said catalysts. The catalysts have the formula I as follows:Ma,Pc/S (I)wherein, M is a compound selected from the group consisting of RuCl.sub.2 (PPh.sub.3).sub.3, RuCl.sub.2 (CO).sub.2 (PPh.sub.3).sub.2, Ru.sub.3 (CO).sub.12, RhCl(CO)(PPh.sub.3).sub.2, IrCl(CO)PPh.sub.3).sub.3, Pd(PPh.sub.3).sub.4, Pt(PPh.sub.3).sub.4 and RuCl.sub.3.xH.sub.2 O, S is an inorganic carrier selected from the group consisting of .alpha.-Al.sub.2 O.sub.3, .gamma.-Al.sub.2 O.sub.3, SiO.sub.2, SiO.sub.2 -Al.sub.2 O.sub.3,Y-zeolite, MgO and TiO.sub.2, and P is a phosphorus compound promoter selected from the group consisting of PPh.sub.3, P(OCH.sub.3).sub.3, P(OC.sub.2 H.sub.5).sub.3, and P(O)(OC.sub.2 H.sub.5).sub.3 ; wherein a is the amount of metal in the catalyst, ranging from 0.
    Type: Grant
    Filed: November 14, 1995
    Date of Patent: May 4, 1999
    Assignee: Korean Research Institute of Chemical Technology
    Inventors: Dae Chul Park, Pyung Kwon Ahn
  • 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: 5859303
    Abstract: A process is provided to trimerize or oligomerize olefins in the presence of an olefin oligomerization catalyst and a solvent which is a product of the olefin oligomerization process.
    Type: Grant
    Filed: December 18, 1995
    Date of Patent: January 12, 1999
    Assignee: Phillips Petroleum Company
    Inventor: Mark E. Lashier
  • Patent number: 5824833
    Abstract: A process for producing an vinylidene olefin of the formula ##STR1## where R.sup.1 and R.sup.2 are the same or different and are hydrogen or alkyl and m is an integer of from 0 to 18, with a catalytically effective amount of a mixture of i) an aluminum compound of the formula R.sup.4.sub.n Al(OR.sup.5).sub.p where R.sup.4 and R.sup.5 are the same or different and are alkyl, n is an integer from 0.75 to 2.75, and p is an integer from 0.25 to 2.25, the sum of n and p being 3, at a temperature of from about 120.degree. C. to about 200.degree. C. whereby a major amount of said vinylidene and deep internal olefin dimer is produced and only a minor amount of a beta internal olefin isomer.
    Type: Grant
    Filed: November 28, 1994
    Date of Patent: October 20, 1998
    Assignee: Amoco Corporation
    Inventor: Kaung-Far Lin
  • 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
  • Patent number: 5811617
    Abstract: Alpha-olefin oligomer is prepared by contacting an alpha-olefin monomer which contains from about 8 to about 16 carbon atoms with a heterogeneous catalyst system formed from (i) a solid olefin polymer having a linear backbone and a plurality of pendant omega-hydroxyalkyl groups, and (ii) a boron trihalide, preferably BF.sub.3. The catalyst system is stable and very reactive at relatively high temperatures, and the solid polymer of the catalyst system can be recovered and reused repeatedly in batch-type operations and can be used for long periods of time in continuous or semi-continuous operations.
    Type: Grant
    Filed: December 13, 1995
    Date of Patent: September 22, 1998
    Assignee: Amoco Corporation
    Inventors: Ronald L. Shubkin, Tze-Chiang Chung, Ruidong Ding
  • Patent number: 5792895
    Abstract: The invention concerns an improved process for the conversion of ethylene into but-1-ene, wherein the ethylene is brought into contact with a catalyst obtained by the interaction of an alkyl titanate, possibly mixed with an ether, with a compound of aluminium of the formula AlR.sub.3 or AlR.sub.2 H, and in the presence of an additive formed by at least one polyethylene glycol and/or one of its derivatives such as a monoether or a monoester of polyethylene glycol.
    Type: Grant
    Filed: April 24, 1997
    Date of Patent: August 11, 1998
    Assignees: Institut Francais du Petrole, Saudi Basic Industries Corporation
    Inventors: Dominique Commereuc, Yves Chauvin, Francois Hugues, Yves Glaize
  • Patent number: 5763723
    Abstract: Novel chromium-containing compounds, such as, for example, chromium pyrrolides, are prepared by forming a mixture of a chromium salt, a metal amide, and an electron pair donor solvent, such as, for example, an ether. These novel chromium-containing, or chromium pyrrolide, compounds can be used either unsupported or supported on an inorganic oxide support, with a metal alkyl and an unsaturated hydrocarbon, to trimerize, oligomerize, and/or polymerize olefins.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: June 9, 1998
    Assignee: Phillips Petroleum Company
    Inventors: William K. Reagen, Ted M. Pettijohn, Jeffrey W. Freeman
  • Patent number: 5750815
    Abstract: Disclosed are ruthenium and osmium carbene compounds which are stable in the presence of a variety of functional groups and which can be used to catalyze olefin metathesis reactions on unstrained cyclic and acyclic olefins. Specifically, the present invention relates to carbene compounds of the formula ##STR1## wherein: M is Os or Ru; R and R.sup.1 are independently selected from hydrogen and functional groups 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.2 -C.sub.20 alkoxy, C.sub.2 -C.sub.20 alkenyloxy, C.sub.2 -C.sub.20 alkynyloxy, aryloxy, C.sub.2 -C.sub.20 alkoxycarbonyl, C.sub.1 -C.sub.20 alkylthio, C.sub.1 -C.sub.20 alkylsulfonyl or C.sub.1 -C.sub.20 alkylsulfinyl; each optionally substituted with C.sub.1 -C.sub.5 alkyl, a halogen, C.sub.1 -C.sub.5 alkoxy or with a phenyl group optionally substituted with a halogen, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy; X and X.sup.
    Type: Grant
    Filed: August 29, 1996
    Date of Patent: May 12, 1998
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, SonBinh T. Nguyen
  • Patent number: 5750817
    Abstract: The disclosure describes a process for preparing .alpha.-olefin oligomers, which comprises carrying out oligomerization of an .alpha.-olefin in a solvent by reacting said .alpha.-olefin in a chromium-based catalyst system composed of a combination of at least a chromium compound, an amine or metal amide, and an alkylaluminum compound, in a contacting mode that the chromium compound and the alkylaluminum compound are not previously contacted with each other.
    Type: Grant
    Filed: March 13, 1996
    Date of Patent: May 12, 1998
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Eiji Tanaka, Hisao Urata, Toshiyuki Oshiki, Takayuki Aoshima, Riichirou Kawashima, Shinji Iwade, Hirofumi Nakamura, Syunji Katsuki, Takeshi Okano
  • Patent number: 5744676
    Abstract: Alpha-olefin oligomers are produced by oligomerizing an alpha-olefin monomer with a catalyst system comprising boron trifluoride, a protic promoter, and a modifier which is (a) at least one 1,3-dioxolane, or (b) at least one 1,3-dioxane, or (c) a combination of (a) and (b). Use of these modifiers in the BF.sub.3 -catalyzed oligomerization makes it possible to modify the promoted catalytic reaction so that product containing as much as 50% or more of dimer can be produced at high conversions, at modest reaction temperatures, and in short reaction periods.
    Type: Grant
    Filed: February 26, 1996
    Date of Patent: April 28, 1998
    Inventors: Kevin J. Theriot, Robert G. Irwin
  • Patent number: 5744677
    Abstract: Alpha-olefins enriched in 1-hexene are prepared by oligomerizing ethylene in the presence of a catalyst comprising (a) a chromium complex containing a coordinating polydentate ligand and, (b) an aluminoxane, in an organic solvent.
    Type: Grant
    Filed: July 14, 1992
    Date of Patent: April 28, 1998
    Assignee: Amoco Corporation
    Inventor: Feng-Jung Wu
  • Patent number: 5731486
    Abstract: A method for producing 3-methyl-2-pentene which is substantially free of any other C.sub.6 olefin, except 2-ethyl-1-butene, by first producing a stream that contains 2-ethyl-1-butene from the trimerization of ethylene, and second by recovering the 2-ethyl-1-butene as 3-methyl-2-pentene via etherification, separation of the ether, and decomposition of the ether back to predominantly 3-methyl-2-pentene with some 2-ethyl-1-butene.
    Type: Grant
    Filed: July 17, 1995
    Date of Patent: March 24, 1998
    Assignee: Exxon Chemical Patents Inc
    Inventors: Dan E. Hendriksen, Gerald G. McGlamery, Michael J. Keenan, Derrick D. Pete
  • Patent number: 5731487
    Abstract: The present invention provides a process for producing olefin having a terminal double bond by trimerizing at least one monomer selected from a group consisting of ethylene, propylene, and 1-butene, which comprises using a catalyst comprising a product prepared from(1) component (A): a chromium compound represented by the formula ?1!CrXmYn ?1!wherein X represents carboxylic acid residue, 1,3-diketone residue, halogen atom or alkoxyl group, Y represents amine, phosphine, phosphine oxide, nitrosyl group or ether, m means an integer of from 2 to 4 and n means an integer of from 0 to 4,component (B): a heterocyclic compound having a pyrrole ring unit or an imidazole ring unit, andcomponent (C): an aluminum compound represented by the formula ?2!AlR.sub.k Z.sub.
    Type: Grant
    Filed: August 9, 1996
    Date of Patent: March 24, 1998
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mitsuhisa Tamura, Kenshi Uchida, Yoshiaki Ito, Kiyoshi Iwanaga
  • Patent number: 5728917
    Abstract: Disclosed are ruthenium and osmium carbene compounds which are stable in the presence of a variety of functional groups and which can be used to catalyze olefin metathesis reactions on unstrained cyclic and acyclic olefins. Specifically, the present invention relates to carbene compounds of the formula ##STR1## wherein: M is Os or Ru; R and R.sup.1 are independently selected from hydrogen and functional groups 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.2 -C.sub.20 alkoxy, C.sub.2 -C.sub.20 alkenyloxy, C.sub.2 -C.sub.20 alkynyloxy, aryloxy, C.sub.2 -C.sub.20 alkoxycarbonyl, C.sub.1 -C.sub.20 alkylthio, C.sub.1 -C.sub.20 alkylsulfonyl or C.sub.1 -C.sub.20 alkylsulfinyl; each optionally substituted with C.sub.1 -C.sub.5 alkyl, a halogen, C.sub.1 -C.sub.5 alkoxy or with a phenyl group optionally substituted with a halogen, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy; X and X.sup.
    Type: Grant
    Filed: October 30, 1995
    Date of Patent: March 17, 1998
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, SonBinh T. Nguyen
  • Patent number: 5710298
    Abstract: Methods of preparing carbene compounds of the formula ##STR1## are disclosed wherein M is Os or Ru; R and R.sup.1 are independently selected from hydrogen and a functional group selected from the group consisting of 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.2 -C.sub.20 alkoxy, C.sub.2 -C.sub.20 alkenyloxy, C.sub.2 -C.sub.20 alkynyloxy, aryloxy, C.sub.2 -C.sub.20 alkoxycarbonyl, C.sub.1 -C.sub.20 alkylthio, C.sub.1 -C.sub.20 alkylsulfonyl or C.sub.1 -C.sub.20 alkylsulfinyl; each optionally substituted with C.sub.1 -C.sub.5 alkyl, a halogen, C.sub.1 -C.sub.5 alkoxy or with a phenyl group optionally substituted with a halogen, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy; X and X.sup.1 are independently selected from any anionic ligand; and L and L.sup.
    Type: Grant
    Filed: August 30, 1996
    Date of Patent: January 20, 1998
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, SonBinh T. Nguyen, Lynda K. Johnson
  • Patent number: 5705725
    Abstract: A process is provided comprising: (a) contacting a hydrocarbyl lithium with an alkali metal hydrocarbyloxide in the presence of an aromatic compound; and thereafter (b) recovering an aromatic alkali metal compound; and thereafter (c) contacting said aromatic alkali metal compound with an alpha-olefin. Optionally, a catalytic support is also present during steps a, b, and c.
    Type: Grant
    Filed: October 2, 1991
    Date of Patent: January 6, 1998
    Assignee: Phillips Petroleum Company
    Inventors: Ted M. Pettijohn, Mark E. Lashier, Henry L. Hsieh
  • Patent number: 5688887
    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: December 21, 1995
    Date of Patent: November 18, 1997
    Assignee: Amoco Corporation
    Inventors: Vahid Bagheri, Bruce Edward Firth, Joanna Kyrle Money, Eric Jan Moore, Frank Calabrese, Robert Scott Hensey
  • Patent number: 5675049
    Abstract: A process is provided for producing liquid ethylene-type random copolymers by copolymerizing ethylene and a C.sub.3 --C.sub.2 O alpha-olefin in the presence of a catalyst comprising an alumoxane and a stereorigid metallocene compound described by the formula:R"(CpR.sub.5)(CpR'.sub.5)MeQ.sub.2wherein each Cp is a cyclopentadienyl or substituted cyclopentadienyl ring; each R and R' is the same or different and is hydrogen or a hydrocarbyl radical having 1-20 carbon atoms or two R or two R' together form a hydrocarbyl radical having 2-20 carbon atoms; R" is a structural bridge between the two Cp rings imparting stereorigidity to the compound; Me is a transition metal of Group IVb of the periodic table; and each Q is a hydrocarbyl radical having 1-20 carbon atoms or is a halogen. A portion of the alumoxane may be replaced with an alkylaluminum.
    Type: Grant
    Filed: August 31, 1993
    Date of Patent: October 7, 1997
    Inventors: Walter Vermeiren, Patrick Brems, Herve Hinnekens
  • Patent number: 5663469
    Abstract: Vinylidene olefin can be formed in good yield and high selectivity in much shorter reaction periods than found critical heretofore. The process involves dimerizing vinyl olefin with at least one trialkylaluminum compound as the catalyst component charged to the reaction vessel. These materials are charged to the reactor so that it contains in the range of 0.001 to 0.5 mol of trialkylaluminum per mol of the initial vinyl olefin. The reaction is performed at a temperature in the range of 100.degree. to 200.degree. C. for a period of time sufficient to convert 10 to 99% by weight of the initial vinyl olefin to a different product with at least 80 wt % vinylidene dimer selectivity. In conducting the process the liquid reaction mixture is in direct contact with a nickel-containing metal alloy surface for at least one hour at a temperature above about 50.degree. C.
    Type: Grant
    Filed: February 5, 1996
    Date of Patent: September 2, 1997
    Assignee: Amoco Corporation
    Inventors: Douglas H. Krzystowczyk, Kaung-Far Lin
  • Patent number: 5659100
    Abstract: Vinylidene olefin can be formed in good yield and high selectivity in much shorter reaction periods than found critical heretofore. The process involves dimerizing vinyl olefin with at least one trialkylaluminum compound as the sole catalyst component charged to the reaction vessel. These materials are charged to the reactor so that it contains in the range of 0.001 to 0.5 mol of trialkylaluminum per mol of the initial vinyl olefin. The reaction is performed at a temperature in the range of 100.degree. to 200.degree. C. for a period of time sufficient to convert 10 to 99% by weight of the initial vinyl olefin to a different product and form a product mixture with at least 80 wt % vinylidene dimer selectivity.
    Type: Grant
    Filed: February 5, 1996
    Date of Patent: August 19, 1997
    Assignee: Amoco Corporation
    Inventor: Kaung-Far Lin
  • Patent number: 5648581
    Abstract: A method for polymerizing or copolymerizing .alpha.-olefin in a vapor phase condition by supplying to a reactor a catalyst composed of a solid catalyst component containing at least titanium and/or vanadium as well as magnesium and an organic aluminum compound wherein the current due to the electric charge transferred from polymer particles electrified to an electrode disposed at a position where sheet-like polymers will be produced in a reactor, as a result of contact of the polymer particles in the reactor with the electrode is determined, and the polymerization or copolymerization is carried out under such condition where the mean value of current is zero or a positive value. As a result, it becomes possible to prevent production of sheet-like polymers and to stably continue the reaction for polymerization.
    Type: Grant
    Filed: February 8, 1996
    Date of Patent: July 15, 1997
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Kunimichi Kubo, Masahiro Niwa, Eiko Kobayashi, Mamoru Yoshikawa
  • Patent number: 5625106
    Abstract: A new class of olefin dimerization catalysts and an efficient method for their preparation is disclosed. B (C.sub.6 F.sub.5).sub.3 reacts quantitatively with Group 4 metallocene type catalysts to yield highly reactive cationic complexes as follows:(L.sub.2 MR.sup.2).sup.+ X.sup.- whereL=R.sub.2 (C.sub.5 H.sub.3); R=CR'.sub.3 ; R.sup.2 =alkyl group (C=1.ltoreq.20);M=Ti, Zr, Hf;X.sup.- =RB(C.sub.6 F.sub.5).sub.3.sup.-, or methylalumoxane.These complexes are potent catalysts and may be used in the dimerization of .alpha.-olefins.
    Type: Grant
    Filed: December 11, 1995
    Date of Patent: April 29, 1997
    Assignee: Northwestern University
    Inventors: Tobin J. Marks, Xinmin Yang
  • Patent number: 5625105
    Abstract: Vinylidene olefin can be formed in good yield in much shorter reaction periods than found critical heretofore. The process involves dimerizing vinyl olefin with at least one trialkylaluminum compound as the sole catalyst component charged to the reaction vessel. These materials are charged to the reactor so that it contains in the range of 0.001 to 0.05 mol of trialkylaluminum per mol of the initial vinyl olefin. The reaction is performed at a temperature in the range of over 140.degree. C. and below 172.degree. C. for a period of time in the range of 1 to 24 hours sufficient to convert at least 10% by weight of the initial vinyl olefin to a different product with at least 80 wt % vinylidene dimer selectivity.
    Type: Grant
    Filed: February 5, 1996
    Date of Patent: April 29, 1997
    Assignee: Amoco Corporation
    Inventors: Kaung-Far Lin, Carroll W. Lanier
  • Patent number: 5557023
    Abstract: The present invention relates to the oligomerization of lower alpha olefins, and particularly ethylene, to higher olefins in the presence of a catalyst precursor having either or both of a dithiophosphinate complex and a heterobifunctional ligand having a phosphine center and an imine or similar center, in the presence of an activator. The catalysts have a high reactivity and a good selectivity.
    Type: Grant
    Filed: May 23, 1995
    Date of Patent: September 17, 1996
    Assignee: The Governors of the University of Alberta
    Inventors: Arpad F. Somogyvari, Beth L. Creed, Antonio P. Nicola, Alan R. Sanger, David J. Law, Ronald G. Cavell
  • Patent number: 5557021
    Abstract: A novel Phillips catalyst for the copolymerization of ethylene with .alpha.-olefins, contains, as a catalytically active component, a finely divided, aluminum silicate-supported, phosphorus-containing chromium catalyst. This can be prepared by applying at least one organic phosphorus(III), (IV) and/or (V) compound and at least one chromium(III) compound which does not react with said phosphorus compounds under the reaction conditions used, in succcession in any order or simultaneously, to a finely divided aluminum silicate hydrogel or xerogel with formation of a catalyst intermediate and activating the catalyst intermediate at elevated temperatures in an oxidizing atmosphere, with the result that the chromium catalyst is formed. The novel Phillips catalyst gives ethylene/.alpha.-olefin copolymers in which the comonomers are more uniformly distributed over the copolymer chains than is the case with ethylene/.alpha.-olefin copolymers which have been prepared with the aid of conventional Phillips catalysts.
    Type: Grant
    Filed: August 8, 1995
    Date of Patent: September 17, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Joachim Mueller, Kaspar Evertz, Siegfried Weber, Guido Funk, Rainer Konrad, Roland Saive
  • Patent number: 5550305
    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.
    Type: Grant
    Filed: April 14, 1994
    Date of Patent: August 27, 1996
    Assignee: Amoco Corporation
    Inventor: Feng-Jung Wu
  • Patent number: 5523507
    Abstract: Novel chromium-containing compounds, such as, for example, chromium pyrrolides, are prepared by forming a mixture of a chromium salt, a metal amide, and an electron pair donor solvent, such as, for example, an ether. These novel chromium-containing, or chromium pyrrolide, compounds can be used either unsupported or supported on an inorganic oxide support, with a metal alkyl and an unsaturated hydrocarbon, to trimerize, oligomerize, and/or polymerize olefins.
    Type: Grant
    Filed: July 29, 1994
    Date of Patent: June 4, 1996
    Assignee: Phillips Petroleum Company
    Inventors: William K. Reagen, Ted M. Pettijohn, Jeffrey W. Freeman
  • Patent number: 5516958
    Abstract: .alpha.,.omega.-Diene oligomers which are useful as synthetic lubricants are prepared by oligomerizing a .alpha.,.omega.-diene using a trialkylaluminum catalyst.
    Type: Grant
    Filed: December 14, 1993
    Date of Patent: May 14, 1996
    Assignee: Albemarle Corporation
    Inventors: Robert A. Schaerfl, Jr., Ali M. Dadgar, Carroll W. Lanier
  • Patent number: 5463157
    Abstract: A method for producing 3-methyl-2-pentene which is substantially free of any other C.sub.6 olefin, except 2-ethyl-1-butene, by first producing a stream that contains 2-ethyl-1-butene from the trimerization of ethylene, and second by recovering the 2-ethyl-1-butene as 3-methyl-2-pentene via etherification, separation of the ether, and decomposition of the ether back to predominantly 3-methyl-2-pentene with some 2-ethyl-1-butene.
    Type: Grant
    Filed: October 29, 1993
    Date of Patent: October 31, 1995
    Assignee: Exxon Chemical Patents, Inc.
    Inventors: Dan E. Hendriksen, Gerald G. McGlamery, Michael J. Keenan, Derrick D. Pete
  • Patent number: 5414178
    Abstract: A catalyst system composition and a process to prepare a catalyst composition comprising a cobalt compound, a metal alkyl and a coordinating compound is provided. The resultant catalyst system composition can be used to dimerize ethylene with high productivity to butenes and high selectivity to 1-butene.
    Type: Grant
    Filed: January 21, 1994
    Date of Patent: May 9, 1995
    Assignee: Phillips Petroleum Company
    Inventor: An-hsiang Wu
  • Patent number: 5414180
    Abstract: Organic aluminoxy compounds are prepared by reacting an organo boronic acid with a trihydrocarbyl aluminum compound. The resulting products are suitable as components for catalyst systems for the polymerization of olefins.
    Type: Grant
    Filed: July 14, 1993
    Date of Patent: May 9, 1995
    Assignee: Phillips Petroleum Company
    Inventors: Rolf L. Geerts, Tara G. Hill
  • Patent number: 5366658
    Abstract: The invention relates to the use of polymethylalkanes having terminal methyl groups and methylene and ethylidene groups of the formula I ##STR1## in which the total number of C atoms n+2 m+2 is 20 to 100 and the ratio of the methyl and methylene groups to the ethylidene groups is 3 to 20:1 and the ethylidene groups are always separated by at least one methylene group, as biodegradable base oils for lubricants and functional fluids. Suitable polymethylalkanes are obtained by oligomerization of .alpha.,.omega.-diolefins, for example in particular according to P 41 19 332.6, or by pyrolysis of ethene/propane copolymers and subsequent hydrogenation in each case. The polymethylalkanes can be combined with conventional additives and other degradable or non-degradable base oils.
    Type: Grant
    Filed: January 10, 1994
    Date of Patent: November 22, 1994
    Assignee: Huls Aktiengesellschaft
    Inventors: Dirk Hoppe, Horst Pennewiss, Frank Kraushaar, Michael Stehr, Roland Streck, Jaroslaw Monkiewicz, Hans G. Wey
  • Patent number: 5362823
    Abstract: In a transition metal catalyst system, the improvement comprising including in the catalyst system an autoacceleration inhibitor, which (i) at about the temperature at which the catalyst system autoaccelerates, decomposes into a poison for the catalyst system; (ii) is present in the catalyst system in an amount sufficient to provide the quantity of poison required to inhibit the autoacceleration of the catalyst system at the autoacceleration temperature; and (iii) is either essentially inert at the normal operating temperature of the catalyst system or will cause substantially less inhibition of the catalyst system at the normal operating temperature than at the autoacceleration temperature.
    Type: Grant
    Filed: March 6, 1990
    Date of Patent: November 8, 1994
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Frederick J. Karol, Kao Sun-Chueh, James S. Drage
  • Patent number: 5330948
    Abstract: The synthesis, and use as precatalysts of chiral organozirconium complexes for olefin polymerization are disclosed, having the structure (C.sub.5 R'.sub.4-x R*.sub.x) A (C.sub.5 R".sub.4-y R'".sub.y) M Q.sub.p, where x and y represent the number of unsubstituted locations on the cyclopentadienyl ring; R', R", R'", and R* represent substituted and unsubstituted alkyl groups having 1-30 carbon atoms and R* is a chiral ligand; A is a fragment containing a Group 13, 14, 15, or 16 element of the Periodic Table; M is a Group 3, 4, or 5 metal of the Periodic Table; and Q is a hydrocarbyl radical, or halogen radical, with 3.ltoreq.p.ltoreq.o. Related complexes may be prepared by alkylation of the corresponding dichorides. In the presence of methylalumoxane or triarylborane cocatalysts, these complexes form "cation-like" species which are highly active for olefin polymerization. In combination with a Lewis acid cocatalyst, propylene or other .alpha.
    Type: Grant
    Filed: March 31, 1992
    Date of Patent: July 19, 1994
    Assignee: Northwestern University
    Inventors: Tobin J. Marks, Moris S. Eisen, Michael A. Giardello