Transition Metal-containing Patents (Class 585/523)
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Patent number: 11358914Abstract: A process comprising A) continuously introducing into a reaction zone i) ethylene, ii) an iron salt, iii) a pyridine bisimine, iv) an organoaluminum compound, and v) an organic reaction medium, and B) forming an oligomer product in the reaction zone, the reaction zone having i) an iron of the iron salt concentration in a range of 5×10?4 mmol/kg to 5×10?3 mmol/kg, ii) an aluminum of the organoaluminum compound to iron of the iron salt molar ratio in a range of 300:1 to 800:1, ii) an ethylene partial pressure in a range of 750 psig to 1200 psig, iv) an ethylene to organic reaction medium mass ratio in a range of 0.8 to 4.5, v) a temperature in a range of 75° C. to 95° C., and optionally vi) a hydrogen partial pressure of at least 5 psi.Type: GrantFiled: March 26, 2021Date of Patent: June 14, 2022Assignee: Chevron Phillips Chemical Company, LPInventors: Steven M. Bischof, Brooke L. Small
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Patent number: 10968290Abstract: Unsaturated and hydrogenated polyalpha-olefin products can be made with a high selectivity toward vinylidenes and tri-substituted vinylenes combined, a high selectivity toward vinylidenes, and a low selectivity toward 1,2-di-substituted vinylenes by using a catalyst system comprising a metallocene compound having the following structure in the polymerization reaction:Type: GrantFiled: March 15, 2018Date of Patent: April 6, 2021Assignee: ExxonMobil Chemical Patents Inc.Inventors: Donna J. Crowther, Patrick C. Chen, Jacqueline A. Lovell, Md Safatul Islam
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Patent number: 10414699Abstract: Disclosed are processes, systems, and reaction systems for the oligomerization of ethylene to form an oligomer product in a reaction zone using a catalyst system having i) a chromium component comprising an N2-phosphinyl amidine chromium compound complex, an N2-phosphinyl formamidine chromium compound complex, an N2-phosphinyl guanidine chromium compound complex, or any combination thereof, and ii) an aluminoxane. Ethylene can be contacted with an organic reaction medium to form an ethylene feedstock mixture prior to contact with the catalyst system. The ethylene feedstock mixture can be contacted with the catalyst system inside or outside of the reaction zone.Type: GrantFiled: May 27, 2016Date of Patent: September 17, 2019Assignee: Chevron Phillips Chemical Company LPInventors: Steven M. Bischof, Orson L. Sydora, Jared T. Fern, Uriah J. Kilgore, Steven Ross Hutchison, Ray Rios, Eric R. Fernandez
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Patent number: 10308563Abstract: The present disclosure relates to a process for producing ethylene oligomers and more particularly, to a process for oligomerizing ethylene by recycling butene, hexene, and octene in an ethylene oligomerization reaction with a catalyst system including a transition metal or transition metal precursor, a ligand with a backbone structure expressed by the following Chemical Formula 1, and a co-catalyst. [Chemical Formula 1] R1—O—Y—O—R2 or R1—OC(?O)—Y—C(?O)OR2 Herein, R1, R2 are each independently hydrocarbyl, substituted hydrocarbyl, heterohydrocarbyl, or substituted heterohydrocarbyl, and Y represents a group connecting O or C(?O)O and is hydrocarbyl, substituted hydrocarbyl, hetero hydrocarbyl, or substituted heterohydrocarbyl. According to the oligomerization method of the present disclosure, in the distribution of the produced ?-olefins, C10?-C12? ?-olefins care highly distributed, the produced ?-olefins have a remarkably high purity.Type: GrantFiled: December 8, 2017Date of Patent: June 4, 2019Assignee: Hanwha Total Petrochemical Co., Ltd.Inventors: Chun Byung Yang, Eun Il Kim
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Patent number: 9896391Abstract: The invention relates to a process for preparing linear ?-olefins, wherein ethylene 1a is conducted into the oligomerization reactor 2 in the liquid phase. The oligomerization reactor 2 has a mechanical stirrer 2a in order to ensure optimal mixing of the liquid ethylene and of the catalyst in the liquid phase. From the top of the oligomerization reactor 2, vaporized ethylene is drawn off together with light ?-olefins and a small proportion of the organic solvent. The gas mixture drawn off from the top of the reactor 2 is condensed together with gaseous fresh ethylene 7 by means of heat exchanger 3 and separator 4. The liquid phase drawn off from the separator 4 is conducted by means of circulation pump 5a as liquid ethylene input 1a back into the oligomerization reactor 2. The liquid products of the oligomerization reaction are drawn off 8 laterally from the base of the reactor 2.Type: GrantFiled: January 13, 2011Date of Patent: February 20, 2018Assignee: LINDE AKTIENGESELLSCHAFTInventors: Karl Heinz Hofmann, Hans Jorg Zander, Anton Wellenhofer, Wolfgang Muller, Anina Wohl
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Patent number: 9688588Abstract: A continuous flow process for the oligomerization of ethylene using a chromium catalyst having a phosphorus-nitrogen-phosphorus (“P—N—P”) ligand provides high selectivity to the desired tetramer (1-octene) with reduced production of coproduct C10+ oligomers. Prior art processes that maximize catalyst activity have provided comparatively poor product selectivity. In particular, the production of larger amounts of C10+ oligomers have been observed under conditions that maximize activity. The present process resolves this problem through the use of a combination of low catalyst concentration and by limiting the octene concentration in the reactor.Type: GrantFiled: December 4, 2013Date of Patent: June 27, 2017Assignee: NOVA Chemicals (International) S.A.Inventors: Peter Zoricak, Stephen John Brown, P Scott Chisholm
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Patent number: 9593055Abstract: The present invention relates to a method for preparing linear alpha-olefins (LAO) by oligomerization of ethylene in the presence of solvent and homogenous catalyst, comprising the steps of: (i) feeding ethylene, solvent and catalyst into an oligomerization reactor, (ii) oligomerizing the ethylene in the reactor, (iii) removing a reactor outlet stream comprising solvent, linear alpha-olefins, ethylene, and catalyst from the reactor via a reactor outlet piping system, (iv) transferring the reactor outlet stream to a catalyst deactivation and removal step, and (v) deactivating and removing the catalyst from the reactor outlet stream, characterized in that at least one organic amine is added into the oligomerization reactor and/or into the reactor outlet piping system.Type: GrantFiled: January 7, 2009Date of Patent: March 14, 2017Assignees: SAUDI BASIC INDUSTRIES CORPORATION, LINDE AGInventors: Vugar Aliyev, Fuad Mosa, Mohammed Al-Hazmi, Syriac Palackal, Ayed Al-Ayed, Sultan Al-Otaibi, Mohammed Zahoor, Wolfgang Müller, Peter M. Fritz, Heinz Bölt, Anton Wellenhofer, Florian Winkler, Uwe Rosenthal, Hans-Jörg Zander, Normen Peulecke, Bernd H. Müller, Karl-Heinz Hofmann, Helmut Fritz, Carsten Taube, Andreas Meiswinkel, Richard Schneider, Anina Woehl
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Patent number: 9120826Abstract: A process comprising contacting an alkene, a hydrogen-boron bond containing compound, and a metal complex selected from the group consisting of an N2-phosphinyl amidine metal complex, an N2-phosphinyl formamidine complex, and an N2-phosphinyl guanidine metal complex under conditions suitable to form an alkylboron compound. A process comprising contacting a linear internal alkene, a metal complex selected from the group consisting of an N2-phosphinyl amidine metal complex, an N2-phosphinyl formamidine complex, and an N2-phosphinyl guanidine metal complex to form a terminal alkylboron compound under conditions suitable to form a terminal alkylboron compound.Type: GrantFiled: June 2, 2014Date of Patent: September 1, 2015Assignee: Chevron Phillips Chemical Company LPInventors: Orson L. Sydora, Mark Stradiotto, Laura Turculet, Brooke L. Small, Robert C. Coffin, Steven M. Bischof
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Patent number: 9045424Abstract: In an ?-olefin manufacturing process by the oligomerization of ethylene using an iron complex of a diimine of a 2,6-diacylpyridine or a 2,6-pyridinecarboxaldehyde, in which certain substituted iminoaryl groups are present, less higher molecular weight unwanted products are produced when the diimine and/or its precursor arylamine does not have impurities with substitution on a second ortho position to the imino group. This leads to less fouling of the process apparatus and higher yields of desired ?-olefins.Type: GrantFiled: March 28, 2014Date of Patent: June 2, 2015Assignee: E I DU PONT DE NEMOURS AND COMPANYInventor: Joel D. Citron
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Patent number: 9035119Abstract: This invention relates to the oligomerization of olefinic compounds in the presence of an activated oligomerization catalyst. The invention also extends to a particular manner for providing an activated oligomerization catalyst.Type: GrantFiled: February 15, 2010Date of Patent: May 19, 2015Assignee: Sasol Technology (PTY) LimitedInventors: Sean William Ewart, Brian William Stirling Kolthammer, David Matthew Smith, Martin John Hanton, John Thomas Dixon, David Hedley Morgan, Henriette De Bod, William Fullard Gabrielli, Stephen John Evans
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Patent number: 9029619Abstract: The present invention relates to a process to make alpha olefins comprising: dehydrating ethanol to recover an ethylene stream, introducing said ethylene stream into an oligomerization zone containing an oligomerization catalyst and into contact with said oligomerization catalyst, operating said oligomerization zone at conditions effective to produce an effluent consisting essentially of 1-butene, 1-hexene, optionally heavier alpha olefins and unconverted ethylene if any, introducing the above effluent into a fractionation zone to recover a stream consisting essentially of 1-butene, a stream consisting essentially of 1-hexene, optionally a stream consisting essentially of heavier alpha olefins and an optional ethylene stream. In an advantageous embodiment the 1-hexene or at least one heavier alpha olefins, if any, are isomerized to an internal olefin and subsequently transformed by metathesis with the aid of additional ethylene into different alpha-olefins with even or odd number of carbons.Type: GrantFiled: December 10, 2009Date of Patent: May 12, 2015Assignee: Total Research & Technology FeluyInventor: Walter Vermeiren
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Patent number: 8969636Abstract: An approach that permits continuous batch conversion of alpha-olefins and internal-olefins to oligomeric materials without fouling the reaction vessel and provides a simple and highly efficient method for making very cost effective catalyst systems based on Zeigler-Natta Group 4 metallocenes. Embodiments of this invention produce diesel and turbine fuels that are 100% synthetic iso-paraffinic kerosenes with flashpoints greater than 61 deg C.Type: GrantFiled: March 21, 2012Date of Patent: March 3, 2015Assignee: The United States of America as Represented by the Secretary of the NavyInventors: Michael E. Wright, Benjamin G. Harvey
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Patent number: 8957270Abstract: A process for producing a base for a fuel from a C2 ethanol feedstock, by a first stage for oligomerization of the feedstock into a hydrocarbon effluent that contains a mixture of olefins for the most part having between 4 and 30 carbons, and contains a C10-C24 fraction that has a mean linearity that is greater than 60%, in the presence of a homogeneous catalytic system that contains a metal precursor of titanium, zirconium, hafnium, nickel and/or iron, a second stage for oligomerization of a portion of the effluent that is obtained from stage a), into a hydrocarbon effluent that contains a mixture of olefins for the most part having between 4 and 30 carbon atoms, and containing a C10-C24 fraction that has a mean linearity that is less than 50%, in the presence of a homogeneous catalytic system.Type: GrantFiled: May 6, 2011Date of Patent: February 17, 2015Assignee: IFP Energies NouvellesInventors: Sandrine Berard, Stephane Harry, Natacha Touchais, Lionel Magna, Helene Olivier-Bourbigou, Cedrik Popelin, David Proriol, Lucien Saussine
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Publication number: 20140378720Abstract: A process to produce polyalpha-olefins includes contacting a feed stream of at least one alpha-olefin monomer having 4 to 25 carbon atoms with a metallocene catalyst compound and an activator, and optionally an alkyl-aluminum compound, under polymerizations conditions in a reactor. The alpha-olefin monomer is present at 10% volume or more in the reactor and the feed stream includes less than 600 ppm of heteroatom containing compounds. The process further includes obtaining a polyalpha-olefin with at least 50 mole % C5 to C24 alpha-olefin monomer and kinematic viscosity at 100° C. of 5000 cSt or less.Type: ApplicationFiled: May 6, 2014Publication date: December 25, 2014Inventors: Margaret M. Wu, Norman Yang, Lisa S. Baugh, Jo Ann M. Canich, Steven P. Rucker, John F. Walzer, JR., Gordon H. Lee, Frederick Y. Lo, Andrew Jackson, Mark P. Hagemeister, Shakeel Tirmizi, Peijun Jiang, Chia S. Chee
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Patent number: 8865959Abstract: A process for the preparation of oligomeric poly alpha-olefins includes oligomerizing low molecular weight PAO oligomer in the presence of a Lewis acid catalyst such as promoted aluminum trichloride or boron trifluoride under oligomerization conditions. The low molecular weight PAO oligomers used as a feed or feed component of the present process are the light olefinic by-product fractions including the dimers and light fractions from the metallocene-catalyzed PAO oligomerization process which are characterized by a molecular weight of 150 to 600 and a terminal olefin (vinylidene) content of at least 25%.Type: GrantFiled: March 4, 2009Date of Patent: October 21, 2014Assignee: ExxonMobil Chemical Patents Inc.Inventors: Abhimanyu Onkar Patil, Margaret May-Som Wu, Norman Yang
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Patent number: 8809613Abstract: The present invention relates to a method for preparing linear alpha-olefins (LAO) by oligomerization of ethylene in the presence of a solvent and homogeneous catalyst, comprising the steps of: (i) feeding ethylene, solvent and catalyst into an oligomerization reactor, (ii) oligomerizing the ethylene in the reactor, (iii) removing a reactor outlet stream comprising solvent, linear alpha-olefins, optionally unreacted ethylene and catalyst from the reactor via a reactor outlet piping system, (iv) dosing at least one additive selected from the group consisting of alcohols, poly-ethylene glycols, polyethylene glycol monoethers, polyethylene glycol diethers, polyamines, amines, amino alcohols and surfactants, (v) transferring the reactor outlet stream containing the additive to a catalyst deactivation and removal section, and (vi) deactivating the catalyst with caustic and removing the deactivated catalyst from the reactor outlet stream, wherein the residence time of the additive in the reactor outlet stream priType: GrantFiled: May 28, 2010Date of Patent: August 19, 2014Assignees: Saudi Basic Industries Corporation, Linde AGInventors: Peter M. Fritz, Heinz Bölt, Andreas Meiswinkel, Carsten Taube, Florian Winkler, Volker Göke, Wolfgang Müller, Anina Wöhl, Richard Schneider, Uwe Rosenthal, Helmut Fritz, Bernd H. Müller, Normen Peulecke, Stephan Peitz, Bhaskar Reddy Aluri, Mohammed Al-Hazmi, Shahid Majeed Azam, Fuad Mosa, Abdullah Al-Dugathier
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Patent number: 8778827Abstract: The present invention relates to a catalyst composition comprising: (a) a binuclear chromium(II) complex; (b) a ligand of the general structure (A) R1R2P—N(R3)—P(R4)—N(R5)—H or (B) R1R2P—N(R3)—P(R4)—N(R5)—PR6R7, wherein R1, R2, R3, R4, R5, R6 and R7 are independently selected from halogen, amino, trimethylsilyl, C1-C10-alkyl, aryl and substituted aryl, wherein the PNPN- or PNPNP-unit is optionally part of a ring system; and (c) an activator or co-catalyst, as well as to a process for oligomerization of ethylene.Type: GrantFiled: November 5, 2008Date of Patent: July 15, 2014Assignees: Saudi Basic Industries Corporation, Linde AGInventors: Vugar Aliyev, Mohammed Al-Hazmi, Fuad Mosa, Peter M. Fritz, Heinz Bölt, Anina Wöhl, Wolfgang Müller, Florian Winkler, Anton Wellenhofer, Uwe Rosenthal, Bernd H. Müller, Marko Hapke, Normen Peulecke
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Publication number: 20140194637Abstract: An ?-olefin oligomer having the following features (1) to (6), and a method for producing the ?-olefin oligomer using a particular double-crosslinked meso complex provide an ?-olefin oligomer that contains a smaller amount of a dimer component while having a low viscosity, not in accordance with the Schulz-Flory distribution, and a method for producing the same: (1) a trimer component proportion C3 (% by mass) that is larger than a theoretical value obtained from the S—F distribution, (2) a hexamer component proportion C6 (% by mass) that is smaller than a theoretical value obtained from the S—F distribution, (3) a kinematic viscosity at 100° C. of 20 mm2/s or less, (4) a meso triad fraction [mm] measured by 13C-NMR of 40% by mol of less, (5) from 0.2 to 1.Type: ApplicationFiled: July 31, 2012Publication date: July 10, 2014Applicant: IDEMITSU KOSAN CO., LTD.Inventors: Minako Tsuji, Takuji Okamoto, Takenori Fujimura, Yutaka Minami
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Publication number: 20140179970Abstract: A catalyst composition and a process for di-, tri- and/or tetramerization of ethylene, wherein the catalyst composition comprises a chromium compound, a ligand of the general structure R1R2P—N(R3)—P(R4)—N(R5)—PR6R7, or any cyclic derivatives thereof, wherein at least one of the P or N atoms of the PNPNP-unit is member of a ring system, the ring system being formed from one or more constituent compounds of the ligand by substitution, and a co-catalyst or activator.Type: ApplicationFiled: December 20, 2013Publication date: June 26, 2014Applicants: Linde AG, Saudi Basic Industries CorporationInventors: Peter M. Fritz, Heinz Bölt, Anina Wöhl, Wolfgang Müller, Florian Winkler, Anton Wellenhofer, Uwe Rosenthal, Bernd H. Müller, Marko Hapke, Normen Peulecke, Mohammed Hassan Al-Hazmi, Vugar O. Aliyev, Fuad Mohammed Mosa
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Patent number: 8686209Abstract: In an ?-olefin manufacturing process by the oligomerization of ethylene using an iron complex of a diimine of a 2,6-diacylpyridine or a 2,6-pyridinecarboxaldehyde, in which certain substituted iminoaryl groups are present, less higher molecular weight unwanted products are produced when the diimine and/or its precursor arylamine does not have impurities with substitution on a second ortho position to the imino group. This leads to less fouling of the process apparatus and higher yields of desired ?-olefins.Type: GrantFiled: August 17, 2010Date of Patent: April 1, 2014Assignee: E. I. du Pont de Nemours and CompanyInventor: Joel David Citron
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Patent number: 8664461Abstract: This invention is directed to new mono-cyclopentadienyl (“mono-Cp”) metallocene catalyst compounds useful for producing high viscosity PAOs with narrow molecular weight distribution and good shear stability. Specifically, this invention relates to a group of bridged mono-Cp catalysts wherein, in an embodiment of the invention, the aromatic ring structure is substituted with: 1) at least one phenyl group, 2) at least one alkyl group, and 3) at least one other group, such as a hydrocarbyl group, a heteroatom, or a heteroatom-containing group.Type: GrantFiled: March 19, 2012Date of Patent: March 4, 2014Assignee: ExxonMobil Chemical Patents Inc.Inventors: Bruce A. Harrington, Abhimanyu O. Patil, Donna J. Crowther, Phillip T. Matsunaga, Kevin B. Stavens, Catalina L. Coker
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Patent number: 8653316Abstract: The present invention relates to a process for the preparation of linear low molecular weight alpha-olefins having 4 to 24 carbon atoms, comprising oligomerizing ethylene in an inert solvent in the presence of a catalyst system comprising: (i) zirconium carboxylate of the formula (R1COO)mZrCl4-m, wherein R1 is saturated or unsaturated aliphatic C1-C10 hydrocarbon or aromatic C6-C14 hydrocarbon and m fulfills 1?m?4, (ii) at least one aluminum compound selected from organoaluminum compounds of the formula R2nAlX3-n, wherein R2 is C1-C20 alkyl, X is chlorine, bromine or iodine, and n fulfills 1?n?2, and/or aluminoxanes, and (iii) at least two different additives selected from the group consisting of hydrogen, esters, ketones, ethers, amines, anhydrides, phosphines and sulfur compounds; as well as to a catalyst used therein.Type: GrantFiled: August 10, 2006Date of Patent: February 18, 2014Assignee: Saudi Basic Industries CorporationInventors: Vugar O. Aliyev, Atieh Abu-Raqabah, Mohammad Zahoor
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Patent number: 8633287Abstract: A polymerization process for copolymerizing ethylene and a series of ?-olefins to form a branched polyethylene, in which the series of ?-olefins is generated in-situ by an ethylene oligomerization catalyst, is improved if the oligomerization catalyst has a Schulz-Flory constant of about 0.30 to about 0.55. This makes very little higher molecular weight ?-olefins, which allows for easy removal of unpolymerized ?-olefins from the polyolefin product.Type: GrantFiled: August 17, 2010Date of Patent: January 21, 2014Assignee: E I du Pont de Nemours and CompanyInventor: Joel David Citron
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Publication number: 20130331629Abstract: The present application relates to N2-phosphinyl guanidine metal salt complexes. The present application also relates to catalyst systems comprising N2-phosphinyl guanidine metal salt complexes and processes for making catalyst systems comprising N2-phosphinyl guanidine metal salt complexes. The present application also relates to utilizing N2-phosphinyl guanidine metal salt complexes in processes of oligomerizing or polymerizing olefins.Type: ApplicationFiled: June 6, 2012Publication date: December 12, 2013Applicant: CHEVRON PHILLIPS CHEMICAL COMPANY LPInventors: Orson J. SYDORA, Brooke L. SMALL, Michael J. CARNEY
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Patent number: 8536391Abstract: This disclosure provides for alpha olefin oligomers and polyalphaolefins (or PAOs) and methods of making the alpha olefin oligomers and PAOs. This disclosure encompasses metallocene-based alpha olefin oligomerization catalyst systems, including those that include at least one metallocene and an activator comprising a solid oxide chemically-treated with an electron withdrawing anion. The alpha olefin oligomers and PAOs prepared with these catalyst systems can have a high viscosity index combined with a low pour point, making them particularly useful in lubricant compositions and as viscosity modifiers.Type: GrantFiled: June 15, 2010Date of Patent: September 17, 2013Assignee: Chevron Phillips Chemical Company LPInventors: Brooke L. Small, Kenneth D. Hope, Qing Yang, Albert P. Masino, Max P. McDaniel, Richard M. Buck, William B. Beaulieu, Eduardo J. Baralt, Eric J. Netemeyer, Bruce Kreischer
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Publication number: 20130217941Abstract: The invention describes a process for oligomerization of olefins into compounds or into a mixture of compounds of general formula CpH2p with 4?p?80 that employs a catalytic composition that comprises at least one organometallic complex of an element of group IV that is selected from among titanium, zirconium, or hafnium, whereby said organometallic complex contains at least one alkoxy-type ligand that is functionalized by a heteroatom that is selected from among nitrogen, oxygen, phosphorus or sulfur, or by an aromatic group.Type: ApplicationFiled: March 28, 2013Publication date: August 22, 2013Applicant: IFP ENERGIES NOUVELLESInventor: IFP ENERGIES NOUVELLES
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Patent number: 8513478Abstract: Liquid poly-alpha-olefins having a KV100 of 2 to 6000 cSt, 20 weight percent dimer or less and a viscosity index of 60 or more are obtained by contacting in a reaction zone, in the presence of from 0 to 60 psi hydrogen, C3 to C20 alpha-olefin monomers with a non-coordinating anion activator, a single bridged meso-metallocene transition metal compound having less than about 35 wt % racemic isomer, and a co-activator. The molar ratio of activator to meso-metallocene is from 10:1 to 0.1:1, and the alpha-olefin monomers in the feed components are present in at least 20 wt % or more based upon the weight of the meso-metallocene, non-coordinating anion activator, co-activator, monomers, and solvent or diluent. The productivity of the process is at least 50,000 g of total product per gram of transition metal compound and no more than 5% monomer is converted from olefin to alkane.Type: GrantFiled: August 1, 2007Date of Patent: August 20, 2013Assignee: ExxonMobil Chemical Patents Inc.Inventors: Margaret M. Wu, Mark P. Hagemeister, Norman Yang
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Patent number: 8487153Abstract: Methods for dimerizing alpha-olefins utilizing immobilized buffered catalysts wherein a buffered ionic liquid is mixed with an organometallic complex of the formula: where X is a halogen, n=2 or 3, M=Ti, V, Cr, Mn, Fe, Co and Ni and R1, R2, R3 and R4 are selected from the group consisting of hydrogen, alkyl, aryl, alkenyl, alkynyl, alkyloxy, substituted aryl, and X are provided. A method for dimerizing alpha-olefins utilizing the immobilized buffered catalysts and a co-catalyst is also provided.Type: GrantFiled: July 1, 2010Date of Patent: July 16, 2013Assignee: Phillips 66 CompanyInventors: Matthias Dötterl, Roland Schmidt, Tanja Englmann, Christine Denner, Helmut G. Alt
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Patent number: 8481444Abstract: Catalyst composition for the oligomerization of ethylene, comprising (i) an at least partially hydrolyzed transition metal compound, obtainable by controlled addition of water to a transition metal compound having the general formula MXm(OR?)4-m or MXm(OOCR?)4-m, wherein R? is an alkyl, alkenyl, aryl, aralkyl or cycloalkyl group, X is halogen, preferably Cl or Br, and m is from 0 to 4; preferably 0-3; and (ii) an organoaluminum compound as a cocatalyst, wherein the molar ratio of water and transition metal compound is within a range of between about (0.01-3):1; a process for oligomerization of ethylene and a method for preparing the catalyst composition.Type: GrantFiled: November 13, 2008Date of Patent: July 9, 2013Assignee: Saudi Basic Industries CorporationInventors: Vugar Aliyev, Fuad Mosa, Mohammed Al-Hazmi
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Publication number: 20130172651Abstract: Processes for oligomerizing olefins utilizing a catalyst system including a) a transition metal complex that is transition metal compound complexed to a pyridine bisimine ligand and b) a metal alkyl and controlling the olefin oligomer product distribution K value by adjusting i) a transition metal of the transition metal complex concentration in the reactor, ii) a metal of the metal alkyl concentration in the reactor, iii) a metal of the metal alkyl to transition metal of the transition metal complex molar ratio in the reactor, and iv) any combination thereof.Type: ApplicationFiled: December 30, 2011Publication date: July 4, 2013Applicant: Chevron Phillips Chemical Company LPInventor: Brooke L. Small
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Publication number: 20130158307Abstract: A low viscosity poly(apha-olefin) (PAO) is produced by contacting one or more C3 to C24 alpha-olefins with an unbridged, substituted bis cyclopentadienyl transition metal compound, a non-coordinating anion activator, and an alkyl-aluminum compound. The molar ratio of transition metal compound to activator is 10:1 to 0.1:1, and the molar ratio of alkyl aluminum compound to transition metal compound is 1:4 to 4000:1. The transition metal compound has either (a) at least one non-isoolefin substitution on both cyclopentadienyl rings, or (b) at least two substitutions on at least one cyclopentadienyl ring. The PAO is comprised of at least 50 mole % of C3 to C24 alpha-olefins and has a kinematic viscosity at 100° C. of 20 cSt or less.Type: ApplicationFiled: May 21, 2012Publication date: June 20, 2013Inventors: Margaret May-Som Wu, Catalina L. Coker, John F. Walzer, JR., Peijun Jiang
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Patent number: 8461406Abstract: According to the present invention there is provided a process for producing an oligomeric product by the oligomerisation of at least one olefinic compound including: A) providing an activated oligomerisation catalyst comprising the combination of: i) a source of a transition metal; ii) a ligating compound of the formula (R1)mX1(Y)X2(R2)n iii) a metal containing activator; and (iv) at least one olefinic compound; B) diluting the activated oligomerisation catalyst of A with an introduced liquid medium; and C) contacting the at least one olefinic compound to be oligomerised with the diluted activated catalyst of B to produce an oligomeric product.Type: GrantFiled: July 10, 2006Date of Patent: June 11, 2013Assignee: Sasol Technology (PTY) LimitedInventors: Matthew James Overett, Kevin Blann, Esna Killian, David Hedley Morgan, Hulisani Maumela, Annette Bollmann, John Thomas Dixon
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Patent number: 8399724Abstract: This invention relates to a vinyl terminated higher olefin copolymer having an Mn of 300 g/mol or more (measured by 1H NMR) comprising: (i) from about 20 to about 99.9 mol % of at least one C5 to C40 higher olefin monomer; and (ii) from about 0.1 to about 80 mol % of propylene; wherein the higher olefin copolymer has at least 40% allyl chain ends. The copolymer may also have an isobutyl chain end to allyl chain end ratio of less than 0.7:1 and/or an allyl chain end to vinylidene chain end ratio of greater than 2:1.Type: GrantFiled: March 25, 2011Date of Patent: March 19, 2013Assignee: ExxonMobil Chemical Patents Inc.Inventors: Donna J. Crowther, Matthew W. Holtcamp, John R. Hagadorn, Charles J. Ruff, George Rodriguez, Patrick Brant
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Publication number: 20130066103Abstract: This invention relates to a co-oligomer having an Mn of 300 to 30,000 g/mol comprising 10 to 90 mol % propylene and 10 to 90 mol % of ethylene, wherein the oligomer has at least X % allyl chain ends, where: 1) X=(?0.94(mole % ethylene incorporated)+100), when 10 to 60 mole % ethylene is present in the co-oligomer, and 2) X=45, when greater than 60 and less than 70 mole % ethylene is present in the co-oligomer, and 3) X=(1.83*(mole % ethylene incorporated)?83), when 70 to 90 mole % ethylene is present in the co-oligomer. This invention also relates to a homo-oligomer, comprising propylene, wherein the oligomer has: at least 93% allyl chain ends, an Mn of about 500 to about 20,000 g/mol, an isobutyl chain end to allylic vinyl group ratio of 0.8:1 to 1.2:1.0, and less than 100 ppm aluminum. This invention also relates to a process of making homo-oligomer, comprising propylene, wherein the productivity is greater than 4500 g/mmol Hf (or Zr)/hour.Type: ApplicationFiled: November 6, 2012Publication date: March 14, 2013Applicant: ExxonMobil Chemical Patents Inc.Inventors: Patrick BRANT, Donna J. CROWTHER, Andrew G. NARVAEZ
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Patent number: 8395007Abstract: A renewable biofuel based on a highly efficient batch catalysis methodology for conversion of 1-butene to a new class of potential jet fuel blends. By tuning the catalyst and then using the dimer produced, the carbon use is about 95% or greater.Type: GrantFiled: July 29, 2009Date of Patent: March 12, 2013Assignee: The United States of America as represented by the Secretary of the NavyInventors: Michael E. Wright, Benjamin G. Harvey, Roxanne L. Quintana
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Publication number: 20130059992Abstract: This invention relates to a co-oligomer having an Mn of 300 to 30,000 g/mol comprising 10 to 90 mol % propylene and 10 to 90 mol % of ethylene, wherein the oligomer has at least X % allyl chain ends, where: 1) X=(?0.94 (mole % ethylene incorporated)+100), when 10 to 60 mole % ethylene is present in the co-oligomer, and 2) X=45, when greater than 60 and less than 70 mole % ethylene is present in the co-oligomer, and 3) X=(1.83*(mole % ethylene incorporated)?83), when 70 to 90 mole % ethylene is present in the co-oligomer. This invention also relates to a homo-oligomer, comprising propylene, wherein the oligomer has: at least 93% allyl chain ends, an Mn of about 500 to about 20,000 g/mol, an isobutyl chain end to allylic vinyl group ratio of 0.8:1 to 1.2:1.0, and less than 100 ppm aluminum. This invention also relates to a process of making homo-oligomer, comprising propylene, wherein the productivity is greater than 4500 g/mmol Hf (or Zr)/hour.Type: ApplicationFiled: November 6, 2012Publication date: March 7, 2013Applicant: ExxonMobil Chemical Patents Inc.Inventors: Patrick BRANT, Donna J. CROWTHER, Andrew G. NARVAEZ, JR.
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Patent number: 8367786Abstract: This invention relates to the oligomerisation of olefinic compounds in the presence of an oligomerisation catalyst activated in two stages by two catalyst activators According to the invention there is provided a process for activating an oligomerisation catalyst by contacting the catalyst with i) a first activator component selected from the group consisting of the aluminoxanes and a mixture of at least one aluminoxane and at least one organylaluminium compound, and ii) a second activator component which is an organylaluminium compound, the process being characterised therein that the oligomerisation catalyst is first contacted with one of the first activator component or second activator component, and the resulting mixture is thereafter contacted with the other of the first activator component or second activator component.Type: GrantFiled: May 22, 2008Date of Patent: February 5, 2013Assignee: Sasol Technology (PTY) LimitedInventors: John Thomas Dixon, David Hedley Morgan, Hulisani Maumela, Palesa Nongodlwana, Johannes Alexander Willemse
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Patent number: 8334420Abstract: A metal complex comprising a metal compound complexed to a heteroatomic ligand, the metal complex having Structure X: wherein R1, R2, R3, and R4 are each independently an alkyl group, a cycloalkyl group, a substituted cycloalkyl group, an aromatic group, or a substituted aromatic group, R1c, R2c, R3c, R4c, and R5c are each independently hydrogen or an alkyl group, and MXp comprises a group IVB, VB, or VIB metal. A metal complex comprising a metal compound complexed to a diphosphino aminyl ligand comprising at least two diphosphino aminyl moieties and a linking group linking each aminyl nitrogen atom of the diphosphino aminyl moieties.Type: GrantFiled: May 7, 2008Date of Patent: December 18, 2012Assignee: Chevron Phillips Chemical Company LPInventors: Brooke L. Small, Jeffery C. Gee
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Publication number: 20120271087Abstract: The oligomerization of ethylene using a chromium catalyst and an aluminoxane activator is well known. The undesired formation of polyethylene as a by-product is also known to occur during prior oligomerization processes. We have discovered that the use of an aluminoxane that is prepared by non-hydrolytic means provides a highly productive activator (co-catalyst) for ethylene oligomerization and mitigates the undesired formation of by-product polyethylene.Type: ApplicationFiled: March 27, 2012Publication date: October 25, 2012Applicant: NOVA CHEMICALS (INTERNATIONAL) S.A.Inventors: Stephen John Brown, Charles Ashton Garret Carter, P. Scott Chisholm, Isam Jaber, Ian Ronald Jobe, Oleksiy Golovchenko
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Patent number: 8269055Abstract: The present invention relates to a method for the deactivation of an organometallic catalyst in the product stream from an oligomerization reactor for the production of linear alpha-olefin, characterized in that the catalyst-containing product stream of the reactor is subjected to a temperature of at least 160° C. in a heating device. A reactor system for the method of the invention is also disclosed.Type: GrantFiled: June 13, 2006Date of Patent: September 18, 2012Assignees: Saudi Basic Industries Corporation, Linde AGInventors: Peter Fritz, Heinz Bölt, Fuad Mosa, Talal Ali
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Patent number: 8258361Abstract: The invention provides transition metal complex compounds, high-activity olefin oligomerization catalysts containing the compounds, and olefin oligomerization processes using the catalysts. A transition metal complex compound [A] according to the invention is represented by Formula (I) or Formula (I?) below. An olefin oligomerization catalyst includes the transition metal complex compound [A]. In an olefin oligomerization process of the invention, an olefin is oligomerized in the presence of the catalyst.Type: GrantFiled: June 27, 2008Date of Patent: September 4, 2012Assignee: Mitsui Chemicals, Inc.Inventors: Yasuhiko Suzuki, Shinsuke Kinoshita, Atsushi Shibahara, Naritoshi Yoshimura, Isao Hara, Tetsuya Hamada, Kazumori Kawamura, Kou Tsurugi, Yasunori Saito, Seiichi Ishii, Yasushi Nakayama, Naoto Matsukawa, Susumu Murata
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Patent number: 8207390Abstract: A low viscosity poly(alpha-olefin) (PAO) is produced by contacting one or more C3 to C24 alpha-olefins with an unbridged, substituted bis-cyclopentadienyl transition metal compound, a non-coordinating anion activator, and an alkyl-aluminum compound. The molar ratio of transition metal compound to activator is 10:1 to 0.1:1 and the molar ratio of alkyl aluminum compound to transition metal compound is 1:4 to 4000:1. The transition metal compound has either (a) at least one non-isoolefin substitution on both cyclopentadienyl rings, or (b) at least two substitutions on at least one cyclopentadienyl ring. The PAO is comprised of at least 50 mole % of C3 to C24 alpha-olefins, has a Mw/Mn between 1 and 1.4, and a kinematic viscosity at 100° C. of 20 cSt or less.Type: GrantFiled: July 19, 2006Date of Patent: June 26, 2012Assignee: ExxonMobil Chemical Patents Inc.Inventors: Margaret May-Som Wu, Catalina L. Coker, John F. Walzer, Jr., Peijun Jiang
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Patent number: 8198497Abstract: A catalytic composition for the selective oligomerization of ethylene and a process for preparing light linear (?-olefins, especially 1-hexene and 1-octene, starting from ethylene, using this composition, said composition comprising the following components: (A) a compound of a transition metal M of Group 4 of the periodic table; (B) an organic compound containing the sulfonic group (>SO2) bonded to two carbon atoms; (C) a hydrocarbyl organometallic compound of a metal M? selected from elements of Groups 1, 2, 12, 13 or 14 of the periodic table; components (A), (B) and (C) being in such a quantity that the atomic ratios respectively of the metal M in (A), of the sulfur S in the sulfonic group of (B) and of the metal M? in (C), respect the following proportions: S/M=(from 0 to 20)/1 and M?/M=(from 2 to 2000)/1, on the condition that when the compound of the metal M in component (A) is not a sulfonic complex of M, the S/M ratio is greater than 0.5, preferably greater than 1.Type: GrantFiled: December 9, 2002Date of Patent: June 12, 2012Assignee: Polimeri Europa S.p.A.Inventors: Paolo Biagini, Liliana Gila
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Patent number: 8119850Abstract: Disclosed is a method for producing an unsaturated hydrocarbon compound wherein an ?-olefin is dimerized by using a catalyst system composed of a metallocene compound (A) and an oxygen-containing organometallic compound modified with a halogen-containing compound (B). By this method, an unsaturated hydrocarbon compound having unsaturated double bonds in a high ratio, in particular the one having a terminal vinylidene group can be produced efficiently.Type: GrantFiled: February 15, 2006Date of Patent: February 21, 2012Assignee: Idemitsu Kosan Co., Ltd.Inventors: Shinjiro Fujikawa, Takuji Okamoto, Kiyohiko Yokota
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Publication number: 20120041241Abstract: This invention relates to the oligomerisation of olefinic compounds in the presence of an activated oligomerisation catalyst. The invention also extends to a particular manner for providing an activated oligomerisation catalyst.Type: ApplicationFiled: February 15, 2010Publication date: February 16, 2012Inventors: Sean William Ewart, Brian William Stiring Kolthammer, David Matthew Smith, Martin John Hanton, John Thomas Dixon, David Hedley Morgan, Henriette De Bod, William Fullard Gabrielli, Stephen John Evans
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Patent number: 8076523Abstract: This invention relates to a process for the oligomerization of at least one olefinic compound in the form of an olefin or a compound including art olefinic moiety by contacting the at least one olefinic compound with at least two different catalysis, namely a tetramerization catalyst and a further oligomerization catalyst. The tetramerization catalyst comprises a combination of a source of a transition metal and a ligating compound of the formula (R1)mX1(Y)X2(R2)n. The invention also relates to an oligomerization catalyst comprising the combination of (i) source of transition metal for both a tetramerization catalyst and a trimerization catalyst; (ii) a ligating compound for a tetramerization catalyst: (iii) a different ligating compound for a trimerization catalyst: and (iv) optionally an activator.Type: GrantFiled: June 13, 2005Date of Patent: December 13, 2011Assignee: Sasol Technology (PTY) LimitedInventors: Annette Bollmann, Hulisani Maumela, Kevin Blann
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Patent number: 8076524Abstract: The present invention relates to a method for preparing olefin comonomers from ethylene. The comonomer generated can be used in a subsequent process, such as a polyethylene polymerization reactor. The comonomer generated can be transported, optionally without isolation or storage, to a polyethylene polymerization reactor. One method includes the steps of: feeding ethylene and a catalyst in a solvent/diluent to one or more comonomer synthesis reactors; reacting the ethylene and the catalyst under reaction conditions sufficient to produce an effluent comprising a desired comonomer; forming a gas stream comprising unreacted ethylene, and a liquid/bottoms stream comprising the comonomer, optionally by passing the effluent to one or more downstream gas/liquid phase separators; and purifying at least a portion of said liquid/bottoms stream by removing at least one of solid polymer, catalyst, and undesirable olefins therefrom.Type: GrantFiled: January 17, 2007Date of Patent: December 13, 2011Assignee: ExxonMobil Chemical Patents Inc.Inventors: James R. Lattner, John F. Walzer, Jr., Krishnan Sankaranarayanan, John Scott Buchanan, Milind Bholanath Ajinkya, Stephen M Wood, Anastasios I Skoulidas, Jay L Reimers, Timothy Daniel Shaffer
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Patent number: 8071835Abstract: The invention is directed to a process for producing polyolefins by one or more homogeneous or colloidal polymerization catalyst wherein residual catalyst is removed by using a solid sorbent.Type: GrantFiled: April 26, 2007Date of Patent: December 6, 2011Assignee: ExxonMobil Chemical Patents Inc.Inventors: Margaret May-Som Wu, Norman Yang, Mark Paul Hagemeister, Shakeel Tirmizi
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Patent number: 8067652Abstract: The invention relates to a process for forming a polyalphaolefin, the process comprising the step of polymerizing at least one C8-C12 monomer, preferably a decene such as 1-decene, in the presence of an aluminoxane, an activator and a metallocene to form the polyalphaolefin, wherein the molar ratio of the aluminoxane to the metallocene is less than 250:1. The invention also relates to a process for forming a polyalphaolefin having a desired kinematic viscosity from at least one monomer in the presence of an aluminoxane, an organoboron compound and a metallocene. The process comprises the steps of, inter alia, providing a correlation between (i) the molar ratio of the aluminoxane to at least one of the organoboron compound and the metallocene, and (ii) the kinematic viscosity of the polyalphaolefin to form polyalphaolefins having predictable viscosities.Type: GrantFiled: August 13, 2009Date of Patent: November 29, 2011Assignee: Chemtura CorporationInventors: Willie C. Bburton, E. Brian Fox
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Patent number: 8058372Abstract: This invention relates to a transition metal catalyst compound represented by the formula: LMX2 or (LMX2)2 wherein each M is independently a Group 7 to 11 metal, preferably a Group 7, 8, 9, or 10 metal; each L is, independently, a tridentate or tetradentate neutrally charged ligand that is bonded to M by three or four nitrogen atoms, (where at least one of the nitrogen atoms is a central nitrogen atom and at least two of the nitrogen atoms are terminal nitrogen atoms), and at least two terminal nitrogen atoms are substituted with one C3-C50 hydrocarbyl and one hydrogen atom or two hydrocarbyls wherein at least one hydrocarbyl is a C3-C50 hydrocarbyl, and the central nitrogen atom is bonded to three different carbon atoms or two different carbon atoms and one hydrogen atom; X is independently a monoanionic ligand, or two X may join together to form a bidentate dianionic ligand.Type: GrantFiled: April 9, 2008Date of Patent: November 15, 2011Assignee: Exxonmobil Chemical Patents Inc.Inventors: Gregory Adam Solan, Christopher James Davies