Using Catalyst Containing Metal Bonded To Or Complexed With C, C-containing Compound, Or H Patents (Class 585/511)
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Patent number: 11952339Abstract: Provided is a method of recovering unreacted ethylene in an ethylene oligomerization process and reusing the ethylene as a raw material, and more particularly, to a method of recovering unreacted ethylene with an increased recovery rate of reuse. When the method of the present invention is used, most of unreacted ethylene may be dissolved in a solvent to be recovered without loss, and a low boiling point reaction product which is not dissolved in the solvent is removed to prevent an unreacted product from being concentrated in a reactor.Type: GrantFiled: July 22, 2020Date of Patent: April 9, 2024Assignees: SK Innovation Co., Ltd., SK Geo Centric Co., Ltd.Inventors: Chansaem Park, Jinhwan Bang, Sungreal Son, Inhyoup Song, Woosung Jung, Eol Han
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Patent number: 11667590Abstract: Process for producing alpha olefins comprising contacting ethylene, a zirconium based catalyst system comprising, a hydrocarbylmetal compound, a chain transfer agent, and optionally an organic reaction medium. Chain transfer agents which can be utilized include a) hydrogen, b) a compound comprising a hydrogen silicon bond, a compound having a hydrogen sulfur bond, a compound having a hydrogen phosphorus bond, or c) a transition metal compound chain transfer agent.Type: GrantFiled: May 26, 2021Date of Patent: June 6, 2023Assignee: Chevron Phillips Chemical Company, LPInventors: Brooke L. Small, Orson L. Sydora, Ronald D. Knudsen
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Patent number: 11352572Abstract: The present invention provides a low viscosity poly-?-olefin lubricating oil and a synthesis method thereof. The method comprises: (1) the ?-olefin raw material is subjected to dehydration treatment so that the water content in the raw material is ?10 ppm; (2) a reaction of the dehydration treated ?-olefin raw material is carried out in the presence of a complex catalyst and gaseous BF3 to obtain a reaction product, wherein the pressure of the gaseous BF3 is 0.01 to 1 MPa; (3) the reaction product obtained in step (2) is sequentially subjected to flash distillation, gas stripping, centrifugation, and washing treatment to obtain an intermediate product; (4) the intermediate product obtained in step (3) is subjected to distillation under reduced pressure to separate the unreacted ?-olefin raw material and ?-olefin dimers, and the remaining heavy fractions are subjected to hydrogenation saturation treatment followed by fractionation and cutting-off.Type: GrantFiled: October 24, 2019Date of Patent: June 7, 2022Assignee: PETROCHINA COMPANY LIMITEDInventors: Hongling Chu, Sihan Wang, Kecun Ma, Xianming Xu, Libo Wang, Guizhi Wang, Yan Jiang, Legang Feng, Yulong Wang, Enhao Sun, Hongliang Huo, Tong Liu, Yali Wang, Xiuhui Wang, Han Gao, Yuanyuan Cao, Fengrong Wang, Weihong Guan, Ruhai Lin, Xuemei Han, Yunguang Han, Fuling Huang, Buwei Yu
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Patent number: 11306040Abstract: A halogen-containing compound as shown in a formula I can be used as a ligand for an ethylene oligomerization catalyst composition. The ethylene oligomerization catalyst composition containing the halogen-containing compound can be used to catalyze ethylene oligomerization, trimerization and tetramerization reactions. As a ligand of a catalyst for ethylene oligomerization, a fluoropolymer can effectively improve the catalytic performance of a catalyst system, and particularly exhibits improved activity and selectivity in an ethylene oligomerization reaction.Type: GrantFiled: October 30, 2019Date of Patent: April 19, 2022Assignees: CHINA PETROLEUM & CHEMICAL CORPORATION, BEIJING RESEARCH INSTITUTE OF CHEMICAL INDUSTRY, CHINA PETROLEUM & CHEMICAL CORPORATIONInventors: Hongfei Wu, Mingfang Zheng, Songshuang Hu, Tonglin Li, Jun Liu, Ke Xu, Xiaoqing Wang, Feng Pan
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Patent number: 11260381Abstract: The invention relates to oligomerization of olefins, such as ethylene, to higher olefins, such as a mixture of 1-hexene and 1-octene, using a catalyst system that comprises a) a source of chromium b) one or more activators and c) a phosphacycle-containing ligating compound. Additionally, the invention relates to a phosphacycle-containing ligating compound and a process for making said compound.Type: GrantFiled: December 3, 2020Date of Patent: March 1, 2022Assignee: Dow Global Technologies LLCInventors: Jerzy Klosin, Kara A. Milbrandt, Scott D. Boelter, David R. Wilson, Mari S. Rosen, Dean M. Welsh, Peter M. Margl, Kyoung Moo Koh, David M. Pearson, Rafael Huacuja
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Patent number: 11230514Abstract: Methods for recycling ethylene from a reaction zone effluent stream from an oligomerization reaction zone, in which the reaction zone effluent stream contains an oligomer product effluent having at least 20 mass % octene(s), include a step of separating the reaction zone effluent stream into a first stream containing ethylene and less than 5 mass % C4+ olefins, a second stream containing butene(s) and less than 10 mass % C6+ olefins, a third stream containing at least 96 mass % hexene(s), and a fourth stream containing at least 96 mass % octene(s). The ethylene-rich first stream is recycled into the oligomerization reaction zone, while the recycle of 1-butene and other butenes is reduced significantly.Type: GrantFiled: May 25, 2021Date of Patent: January 25, 2022Assignee: Chevron Phillips Chemical Company, LPInventor: Bruce E. Kreischer
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Patent number: 11224870Abstract: The present invention relates to a ligand, an ethylene oligomerization catalyst including the ligand, and a method for selectively producing 1-hexene or 1-octene from ethylene by using the catalyst. The ligand according to the present invention is a bis(diphenylphosphino)ethene with a phosphorus atom substituted with a fluoro-substituted phenyl, and when the ligand is used for ethylene oligomerization, the high temperature activity of the catalyst can be increased.Type: GrantFiled: October 12, 2018Date of Patent: January 18, 2022Assignees: SK Innovation Co., Ltd., SK Global Chemical Co., Ltd.Inventors: Hoseong Lee, Yongnam Joe
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Patent number: 11117846Abstract: Disclosed are a catalyst system capable of selectively oligomerizing olefins including ethylene and a method for preparing an olefin oligomer by using the same and, specifically, a novel catalyst system capable of trimerizing and tetramerizing olefins, unlike olefin oligomerization catalyst systems that have been reported so far, and a method for preparing an olefin oligomer by using the same. The present invention provides a catalyst system for olefin oligomerization, the catalyst system comprising: a ligand compound represented by chemical formula 1 or 2; a chromium compound; a metal alkyl compound; and an aliphatic or alicyclic hydrocarbon solvent.Type: GrantFiled: October 11, 2018Date of Patent: September 14, 2021Assignee: LOTTE CHEMICAL CORPORATIONInventors: Hee Young Kim, Tae Jin Kim, Seung Woong Yoon
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Patent number: 10981154Abstract: Disclosed are a novel catalyst system which is a catalyst system for selectively oligomerizing olefin including ethylene and may trimerize and tetramerize olefin, different from the catalyst system for olefin oligomerization reported until now, and a method for preparing an olefin oligomer using same. The present invention provides a catalyst system for olefin oligomerization, including a ligand compound represented by Formula 1 or 2; a chromium compound; and a metal alkyl compound, and a method for preparing an olefin oligomer using same.Type: GrantFiled: September 14, 2017Date of Patent: April 20, 2021Assignee: LOTTE CHEMICAL CORPORATIONInventors: Min Jae Shin, Hee Young Kim, Tae Jin Kim, Seung Woong Yoon
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Patent number: 10919031Abstract: The invention relates to oligomerization of olefins, such as ethylene, to higher olefins, such as a mixture of 1-hexene and 1-octene, using a catalyst system that comprises a) a source of chromium b) one or more activators and c) a phosphacycle-containing ligating compound. Additionally, the invention relates to a phosphacycle-containing ligating compound and a process for making said compound.Type: GrantFiled: June 8, 2020Date of Patent: February 16, 2021Assignee: Dow Global Technologies LLCInventors: Jerzy Klosin, Kara A. Milbrandt, Scott D. Boelter, David R. Wilson, Mari S. Rosen, Dean M. Welsh, Peter M. Margl, Kyoung Moo Koh, David M. Pearson, Rafael Huacuja
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Patent number: 10793489Abstract: Disclosed herein is a process for forming an oligomer product comprising (a) introducing into a reaction zone (i) ethylene; (ii) a heteroatomic ligand metal salt complex comprising a heteroatomic ligand complexed to a first metal salt; (iii) a second metal salt wherein an equivalent molar ratio of the second metal salt to the heteroatomic ligand of the heteroatomic ligand metal salt complex is at least 0.5:1 and where the second metal salt is an iron salt, a cobalt salt, or any combination thereof; (iv) an organoaluminum compound; and (b) forming an oligomer product. Also disclosed herein is a process comprising (a) introducing into a reaction zone (i) ethylene; (ii) a heteroatomic ligand; (iii) a metal salt where an equivalent molar ratio of the metal salt to the heteroatomic ligand is at least 1.5:1; (iv) an organoaluminum compound; and (b) forming an oligomer product.Type: GrantFiled: November 26, 2019Date of Patent: October 6, 2020Assignee: Chevron Phillips Chemical Company LPInventors: Brooke L. Small, Matthew F. Milner
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Patent number: 10702861Abstract: The invention relates to oligomerization of olefins, such as ethylene, to higher olefins, such as a mixture of 1-hexene and 1-octene, using a catalyst system that comprises a) a source of chromium b) one or more activators and c) a phosphacycle-containing ligating compound. Additionally, the invention relates to a phosphacycle-containing ligating compound and a process for making said compound.Type: GrantFiled: July 11, 2019Date of Patent: July 7, 2020Assignee: Dow Global Technologies LLCInventors: Jerzy Klosin, Kara A. Milbrandt, Scott D. Boelter, David R. Wilson, Mari S. Rosen, Dean M. Welsh, Peter M. Margl, Kyoung Moo Koh, David M. Pearson, Rafael Huacuja
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Patent number: 10575543Abstract: Provided herein is 5-(2-(1-ethoxyethoxy)propan-2-yl)-2-methyl-2-vinyltetrahydrofuran and its use as a flavor and aroma modifier in foods and beverages.Type: GrantFiled: December 21, 2015Date of Patent: March 3, 2020Assignee: Firmenich SAInventors: Gary B. Womack, Matthew Sillick
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Patent number: 10544069Abstract: The invention describes a method for dimerization of ethylene implementing a step for treatment of raw effluent by neutralization, at the outlet of the reactor, of the catalyst for dimerization of ethylene into but-1-ene by a particular alcohol.Type: GrantFiled: December 4, 2018Date of Patent: January 28, 2020Assignee: IFP Energies NouvellesInventors: Lionel Magna, Aurelie Camarata
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Patent number: 10508065Abstract: Methods of preparing oligomers of an olefin are provided. The methods can include providing an alkylaluminum compound and irradiating the alkylaluminum compound with microwave radiation to provide an irradiated alkylaluminum compound. The methods can further include mixing the irradiated alkylaluminum compound with a chromium compound, a pyrrole compound, and a zinc compound to provide a catalyst composition. The methods can further include contacting an olefin with the composition to form oligomers of the olefin. The olefin can include ethylene, and the oligomers of the olefin can include 1-hexene.Type: GrantFiled: December 23, 2014Date of Patent: December 17, 2019Assignee: PUBLIC JOINT STOCK COMPANY “SIBUR HOLDING”Inventors: Timur Mikhailovich Zilbershtein, Denis Alekseevich Lenev, Maxim Vladimirovich Lipskikh
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Patent number: 10421066Abstract: The invention describes a novel catalytic composition comprising at least one nickel precursor A with at least one diphosphinamine ligand B1 of formula (R1)(R?1)P—N(R3)—P(R2)(R?2) or an iminobisphosphine ligand B2 of formula (R3)N?P(R1)(R?1)—P(R2)(R?2) or an iminobisphosphine ligand B?2 of formula (R3)N?P(R2)(R?2)—P(R1)(R?1). The invention also describes the use of said catalytic composition in a method for the oligomerisation of olefins.Type: GrantFiled: June 26, 2014Date of Patent: September 24, 2019Assignees: IFP Energies Nouvelles, Universiteit Van AmsterdamInventors: Pierre-Alain Breuil, Pierre Boulens, Joost Reek, Helene Olivier-Bourbigou
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Patent number: 10376869Abstract: The invention relates to oligomerization of olefins, such as ethylene, to higher olefins, such as a mixture of 1-hexene and 1-octene, using a catalyst system that comprises a) a source of chromium b) one or more activators and c) a phosphacycle-containing ligating compound. Additionally, the invention relates to a phosphacycle-containing ligating compound and a process for making said compound.Type: GrantFiled: March 10, 2016Date of Patent: August 13, 2019Assignee: Dow Global Technologies LLCInventors: Jerzy Klosin, Kara A. Milbrandt, Scott D. Boelter, David R. Wilson, Mari S. Rosen, Dean M. Welsh, Peter M. Margl, Kyoung Moo Koh, David M. Pearson, Rafael Huacuja
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Patent number: 10344044Abstract: The present disclosure relates to a ligand compound, a catalyst system for oligomerization, and a method for olefin oligomerization using the same. The catalyst system for oligomerization using the ligand compound according to the present disclosure has excellent catalytic activity, exhibits high selectivity to 1-hexene and 1-octene, and greatly reduces the production of the by-products, thereby enabling efficient preparation of alpha-olefin.Type: GrantFiled: January 26, 2016Date of Patent: July 9, 2019Assignee: LG CHEM, LTD.Inventors: Eun Ji Shin, Yong Ho Lee, Jin Young Park, Seok Pil Sa, Ki Soo Lee, Seul Ki Im
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Patent number: 10173948Abstract: The present disclosure relates to a method for oligomerization of olefins. The method for oligomerization of olefins according to the present disclosure not only provides excellent catalytic activity and stable process operation, but also exhibits high selectivity to 1-hexene or 1-octene by using a catalyst system including an activity modifier.Type: GrantFiled: August 16, 2016Date of Patent: January 8, 2019Assignee: LG Chem, Ltd.Inventors: Seul Ki Im, Yong Ho Lee, Eun Ji Shin, Ki Soo Lee, Jin Young Park, Seok Pil Sa, Yoon Ki Hong
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Patent number: 10112876Abstract: The present invention relates to a process for the oligomerization of ethylene, comprising: a) oligomerization of ethylene in a reactor in the presence of solvent and catalyst; b) transferring reactor overhead effluent to an externally located cooling device and recycling condensed effluent into the reactor; c) transferring the reactor bottom effluent to a series of fractionation columns and, in the following order, i) optionally separating a C4 fraction, ii) separating a C6 fraction, iii) simultaneously separating C8 and C10 fractions and recycling thereof into the reactor , and iv) separating residues comprising ?C12 fractions, spent catalyst polymer material and quench media, from the process, wherein the solvent is separated in any of the steps i)-iv)and/or in an additional step.Type: GrantFiled: September 5, 2013Date of Patent: October 30, 2018Assignee: SAUDI BASIC INDUSTRIES CORPORATIONInventors: Shahid Majeed Azam, Abduljelil Iliyas, Abdullah Mohammad Alqahtani, Shehzada Khurram, Anina Wöhl, Wolfgang Müller, Marco Harff, Andreas Meiswinkel, Heinz Bölt
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Patent number: 9969828Abstract: Linear low density polyethylene (LLDPE) is produced from an ethylene-only feed over a tandem catalyst system consisting of a phenoxy-imine titanium trimerization catalyst and a silylene-linked cyclopentadienyl/amido titanium polymerization catalyst co-supported on the same methylaluminoxane/silica particles. The level of 1-hexene incorporation in the LLDPE can be controlled by varying the ethylene pressure. Tandem, co-silica-supported ethylene trimerization and ethylene/1-hexene copolymerization catalysts produce linear low density polyethylene (LLDPE) from an ethylene-only feedstock. The percentage 1-hexene incorporation in the LLDPE may be varied by adjusting the amounts of the two catalysts on the silica support.Type: GrantFiled: January 20, 2017Date of Patent: May 15, 2018Assignees: California Institute of Technology, King Fahd University of Petroleum and MineralsInventors: Dinesh C. Aluthge, Aaron Sattler, Mamdouh Al-Harthi, Jay A. Labinger, John E. Bercaw
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Patent number: 9637509Abstract: Provided are ligand compounds selected from among N-(diphenylphosphino)-1,1-diphenyl-N-(4-phenylbutan-2-yl)phosphinamine and N4,N4-bis(diphenylphosphino)-N1,N1-diethylpentane-1,4-diamine, a catalyst system for olefin oligomerization, and a method for olefin oligomerization using the same. The catalyst system for olefin oligomerization has excellent catalytic activity, and yet, exhibits high selectivity to 1-hexene or 1-octene, thus enabling more efficient preparation of alpha-olefin.Type: GrantFiled: November 10, 2014Date of Patent: May 2, 2017Assignee: LG CHEM, LTD.Inventors: Eun Ji Shin, Yong Ho Lee, Seok Pil Sa, Ki Soo Lee
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Patent number: 9586874Abstract: The invention relates to the production of olefin oligomers by a method of oligomerization of olefins, and, in particular, to a method of isolating olefin oligomerization products and decomposing the oligomerization catalyst residues. The method of isolating products of an oligomerization reaction of olefins including a terminal double bond, in which the reaction is carried out by the action of a catalyst having chromium compounds, a nitrogen-containing ligand and organoaluminum compounds, includes a step of isolating independent olefin products and a step of treating catalyst residues. Further, the method includes the following sequential steps: a) isolating at least one liquid product of the oligomerization reaction of olefins from an output stream of an oligomerization reactor; b) treating a residue with an aqueous solution of an acid; and c) separating an organic layer and an aqueous layer.Type: GrantFiled: June 21, 2012Date of Patent: March 7, 2017Assignee: Public Joint Stock Company “Sibur Holding”Inventors: Timur Mikhailovich Zilbershtein, Maxim Vladimirovich Lipskikh, Vladislav Alexandrovich Kardash, Vladlena Vladimirovna Suvorova
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Patent number: 9518138Abstract: A liquid random copolymer of ethylene and alpha-olefin prepared by using specific metallocene catalyst and ionic compound and a method for preparing the same are disclosed. The liquid random copolymer has high viscosity index and shear stability so that it is useful as synthetic lubricants. The liquid random copolymer of ethylene and alpha-olefin (1) comprises 60 to 40 mol % of ethylene units and 40 to 60 mol % of alpha-olefin unit having 3 to 20 carbon atoms, (2) has number average molecular weight (Mn) of 500 to 10,000 and a molecular weight distribution (Mw/Mn, Mw is the weight average molecular weight) of 3 or less measured by Gel Permeation Chromatography (GPC) (3) has Kinematic Viscosity at 100° C. of 30 to 5,000, (4) has pour point of 30 to ?45° C., and (5) has Bromine Number of 0.1 or less.Type: GrantFiled: November 15, 2013Date of Patent: December 13, 2016Assignee: DAELIM INDUSTRIAL CO., LTD.Inventors: Jae Hoon Uhm, Sang-Deok Mun, Jin-Hun Ju, Hee-Sun Bae, Sah-Mun Hong, Byung-Keel Sohn
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Patent number: 9499455Abstract: The invention concerns a process for the selective dimerization of ethylene to 1-butene employing a catalytic composition comprising at least one alkoxy or aryloxy titanium compound, at least one additive selected from ether type compounds and at least one aluminium compound.Type: GrantFiled: July 2, 2015Date of Patent: November 22, 2016Assignee: IFP ENERGIES NOUVELLESInventors: Lionel Magna, Helene Olivier-Bourbigou
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Patent number: 9475738Abstract: Disclosed herein are methods and apparatus for deactivating a catalyst composition in an reaction product stream. One such method and apparatus contact the catalyst composition with a catalyst-deactivating composition and a diluent in a vapor phase of a product-receiving vessel, wherein the boiling point of the diluent is at least 5.0° C. greater than the boiling point of the catalyst-deactivating composition. Also disclosed are oligomerization systems for producing oligomers.Type: GrantFiled: August 23, 2012Date of Patent: October 25, 2016Assignee: ExxonMobil Chemical Patents Inc.Inventors: Michael W. Weber, James R. Lattner, Michael J. Veraa
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Patent number: 9394212Abstract: In a process for the cooligomerization of olefins, an olefin starting material comprising olefins having n carbon atoms and olefins having 2n carbon atoms is reacted over an olefin oligomerization catalyst to give a reaction product. The process is carried out under such conditions that the conversion of olefins having 2n carbon atoms is less than 10%. Both the cooligomer having 3n carbon atoms and the olefin having 2n carbon atoms which has been separated off from the reaction product have a high hydroformylatability.Type: GrantFiled: June 14, 2011Date of Patent: July 19, 2016Assignee: BASF SEInventors: Wolfgang Rohde, Qiang Miao, Stefan Bitterlich, Gauthier Luc Maurice Averlant, Hans-Guenter Wagner, Beatrice Röβler-Feigel
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Patent number: 9315636Abstract: The present disclosure relates to soluble, multi-ligand-substituted metal compounds with improved stability as well as compositions made from them and methods of their use.Type: GrantFiled: December 7, 2012Date of Patent: April 19, 2016Assignee: AZ ELECTRONIC MATERIALS (LUXEMBOURG) S.A.R.L.Inventors: Huirong Yao, M. Dalil Rahman, Salem K. Mullen, JoonYeon Cho, Clement Anyadiegwu, Munirathna Padmanaban
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Patent number: 9278894Abstract: Provided is a process for preparing oligomers from an alkane. The process comprises (a) contacting an alkane under dehydrogenation conditions in the presence of a dehydrogenation catalyst such as an iridium catalyst complex comprising iridium complexed with a benzimidiazolyl-containing ligand to form olefins, and (b) contacting the olefins prepared in step (a) under oligomerization conditions with an oligomerization catalyst such as a nickel, platinum or palladium metal catalyst complex comprising the metal complexed with a nitrogen containing bi- or tridentate ligand to prepare oligomers of the olefins, and hydrogenating the olefin oligomers. In one embodiment, the ligands of the catalyst complexes in step (a) and step (b) can be the same.Type: GrantFiled: September 12, 2012Date of Patent: March 8, 2016Assignees: Chevron U.S.A. Inc., Rutgers, The State University of New JerseyInventors: Alan Stuart Goldman, Robert Timothy Stibrany, William L. Schinski
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Patent number: 9175020Abstract: Lithium diphenylphosphide solutions in a solvent, e.g., diethoxymethane (DEM), that are more stable than when tetrahydrofuran (THF) is used as a solvent. Methods of producing them are also disclosed.Type: GrantFiled: February 13, 2009Date of Patent: November 3, 2015Assignee: Rockwood Lithium Inc.Inventors: Jeffrey Allen McCall, Mark J. Hintze
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Publication number: 20150148572Abstract: Processes for the effective dimerization and oligomerization of a mixed butenes feed using an ion exchange resin based catalyst are provided. The dimerization and oligomerization processes produce highly branched C8 and C8+ olefins (e.g., C12, C16 and C20 olefins) which could be used as superior fuel blending component for higher energy contents, higher octane value, higher octane sensitivity and lower RVP.Type: ApplicationFiled: November 27, 2013Publication date: May 28, 2015Applicant: Saudi Arabian Oil CompanyInventors: Wei Xu, Miao Sun
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Publication number: 20150126790Abstract: A process (10) for oligomerising a hydrocarbon to form at least one co-monomer product (22) includes feeding a hydrocarbon reactant and organic liquid diluent solvent (32) into an oligomerisation reactor (12). The organic liquid diluent solvent has a normal boiling point below the normal boiling point of 1-hexene but above ?20° C., or the organic diluent solvent is in the form of a solvent admixture with at least 70% by mass of the solvent admixture constituting organic diluent solvents having a normal boiling point below the normal boiling point of 1-hexene but above ?20° C. The oligomerisation reactor (12) holds at least one co-monomer product formed in the oligomerisation reactor admixed with a catalyst system (25) introduced into the oligomerisation reactor (12). The catalyst system (25) includes a catalyst dissolved in at least one catalyst solvent.Type: ApplicationFiled: May 8, 2013Publication date: May 7, 2015Inventors: Denise Louisette Venter, Kenny Tenza, Palesa Nongodlwana, Matthew James Overett, Kevin Blann, Nicolaus Ladislaus Stark, Craig McGregor, Richard Neil Walsh
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Publication number: 20150045603Abstract: This invention relates to a catalyst system for selective oligomerization of ethylene, which includes (i) a chromium compound; (ii) a ligand having a P—C—C—P backbone structure; and (iii) an activator, thus preparing 1-hexene and/or 1-octene with high activity and selectivity.Type: ApplicationFiled: March 15, 2013Publication date: February 12, 2015Inventors: Tack Kyu Han, Min Seon Jung, Dong Chul Shin, Ho Seong Lee, Sung Seok Chae, Jong Sok Han
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Publication number: 20140364669Abstract: Provided is a production process for ?-olefin which does not comply the Shultz-Flory distribution and which is excellent in the yields of ?-olefins of 1-hexene up to 1-tetradecene each having 6 to 14 carbon atoms, particularly a yield of 1-octene. The above production process is characterized by polymerizing ethylene using (A) a specific chromium compound, (B) a specific aminophosphine ligand compound and (C) a promoter.Type: ApplicationFiled: December 13, 2012Publication date: December 11, 2014Applicant: IDEMITSU KOSAN CO., LTD.Inventors: Yasushi Shiraki, Masahiko Kuramoto, Takuji Okamoto
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Publication number: 20140357918Abstract: The present invention generally relates to a process that prepares polyethylenes, poly-?-olefins or poly(co-ethylene-?-olefin) having backbone weight average molecular weights less than 2500 daltons. The process uses a metal-ligand complex as a precatalyst and can be carried out at temperatures ranging from 30° C. to 300° C. The relatively low molecular weight of the products enables improved viscosity control for a wide variety of applications.Type: ApplicationFiled: November 28, 2012Publication date: December 4, 2014Applicant: DOW GLOBAL TECHNOLOGIES LLCInventors: Jerzy Klosin, Pulikkottil J. Thomas
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Publication number: 20140316088Abstract: The present invention provides, among other things, novel compounds and methods for metathesis reactions. In some embodiments, a provided compound has the structure of formula I or II. In some embodiments, the present invention provides compounds and methods for Z-selective olefin metathesis.Type: ApplicationFiled: April 17, 2014Publication date: October 23, 2014Applicant: Massachusetts Institute of TechnologyInventors: Richard Royce Schrock, Michael R. Reithofer
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Patent number: 8816146Abstract: Methods for dimerizing alpha-olefins utilizing immobilized buffered catalysts wherein a buffered ionic liquid is mixed with an organometallic complex of the formula: where M is selected from the group of Ti, Zr, Hg, Ni, and V and R and R? are selected from the group consisting of hydrogen, alkyl, aryl, alkenyl, alkynyl, alkyloxy, substituted aryl, and halogens, are provided.Type: GrantFiled: July 1, 2010Date of Patent: August 26, 2014Assignee: Phillips 66 CompanyInventors: Tanja Englmann, Christine Denner, Helmut G. Alt, Roland Schmidt, Matthias Dötterl
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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: 20140171712Abstract: A new family of crystalline aluminosilicate zeolites has been synthesized that has been designated UZM-43. These zeolites are similar to previously known ERS-10, SSZ-47 and RUB-35 zeolites but are characterized by unique x-ray diffraction patterns and compositions and have catalytic properties for carrying out various hydrocarbon conversion processes. Catalysts made from these zeolites are useful in hydrocarbon conversion reactions.Type: ApplicationFiled: December 18, 2012Publication date: June 19, 2014Applicant: UOP LLCInventors: Deng-Yang Jan, Jaime G. Moscoso, Paula L. Bogdan
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Patent number: 8722953Abstract: The invention relates to a process for preparing substituted or unsubstituted 1,7-diolefins by hydrodimerizing non-cyclic olefins having at least two conjugated double bonds in the presence of a reducing agent and of a catalyst, wherein the catalyst used is a metal-carbene complex.Type: GrantFiled: June 6, 2007Date of Patent: May 13, 2014Assignee: Evonik Degussa GmbHInventors: Volker Brehme, Manfred Neumann, Frank Bauer, Elke Fiebig-Bauer, Franz Rudolf Bauer, Johanna Elisabeth Bauer, Dirk Roettger
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Patent number: 8716488Abstract: The present invention refers to novel ruthenium- and osmium-based catalysts for olefin metathesis reactions, particularly to catalysts having stereoselective properties. Z-selectivity is obtained by utilizing two mono-anionic ligands of very different steric requirement. In olefin metathesis reactions these catalysts selectively provide the Z-isomer of disubstituted olefinic products.Type: GrantFiled: September 25, 2012Date of Patent: May 6, 2014Assignee: Bergen Teknologioverforing ASInventors: Vidar R. Jensen, Giovanni Occhipinti, Frederick Rosberg Hansen
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Patent number: 8664460Abstract: The application discloses novel processes for the oligomerization of unsaturated hydrocarbons, and more specifically the use of selected ionic liquids containing Indium (III) Chloride in the oligomerization of unsaturated hydrocarbons, which allows for selection of the oligomers formed.Type: GrantFiled: December 12, 2006Date of Patent: March 4, 2014Assignee: The Queen's University of BelfastInventors: Martyn John Earle, Johanna Kärkkäinen, Natalia V. Plechkova, Alina Tomaszowska, Kenneth Richard Seddon
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Patent number: 8658750Abstract: Disclosed herein is a method for separating from the reactor effluent of an olefin oligomerization procedure those catalyst materials and polymeric by-products which can cause difficulties in the downstream processing of such effluent. Polymer by-products and catalyst in the effluent are separated from reaction products by flash vaporization utilizing an in-situ hot solvent which is contacted with the effluent and serves as the heating medium to promote this flash vaporization step. Subsequent processing of a liquid portion of the effluent which is left after flash vaporization involves recovery of catalyst and polymeric by-products therefrom in a steam stripping vessel. Also disclosed is a multiple reactor system which can be used for continuous trimerization of ethylene to 1-hexene while at the same time washing polymeric by-products from one of the reactors in the series using a wash oil solvent.Type: GrantFiled: March 9, 2010Date of Patent: February 25, 2014Assignee: ExxonMobil Chemical Patents Inc.Inventors: James R. Lattner, Michael W. Weber, Jimmy L. Tardy, Howard G. Large, Peter N. Loezos, Randy L. Foster, Jason D. Davis
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Patent number: 8637721Abstract: The present invention relates to 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 (A) R1R2P—N(R3)—P(R4)—N(R5)—H or (B) R1R2P—N(R3)—P(R4)—N(R5)—PR6R7, or any cyclic derivatives of (A) and (B), wherein at least one of the P or N atoms of the PNPN-unit or PNPNP-unit is member of a ring system, the ring system being formed from one or more constituent compounds of structures (A) or (B) by substitution and a co-catalyst or activator.Type: GrantFiled: June 16, 2008Date of Patent: January 28, 2014Assignees: Saudi Basic Industries Corporation, Linde AGInventors: 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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Publication number: 20140018565Abstract: A silicon-bridged Cp-Ar transition metal complex serves as a catalytic component capable of efficiently and highly selectively producing 1-hexene through trimerization reaction of ethylene. The transition metal complex is represented by formula (1): wherein M represents a transition metal atom of Group 4 of the Periodic Table of the Elements; X1, X2, X3, R1, R2, R3, R4, R5, R6, R7, R8, and R9 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, and an aralkyloxy group having 7 to 20 carbon atoms, and wherein each of the groups may have a halogen atom as a substituent.Type: ApplicationFiled: March 29, 2012Publication date: January 16, 2014Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Taichi Senda, Masaya Tanimoto
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Publication number: 20140012056Abstract: Disclosed is a method for producing 1-hexene that is capable of reducing the amount of by-product polymers when 1-hexene is produced through the trimerization reaction of ethylene. The method for producing 1-hexene comprises the following steps 1 and 2: step 1: the step of preparing a catalytic component by bringing a transition metal complex represented by any one of formulae (1-1) to (1-3) into contact with a specific organic aluminum compound in the absence of ethylene; and step 2: the step of trimerizing ethylene in the presence of a catalyst obtainable by bringing the catalytic component obtained in step 1 into contact with a specific boron compound.Type: ApplicationFiled: March 29, 2012Publication date: January 9, 2014Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Takayuki Hishiya, Takahiro Hino, Taichi Senda
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Patent number: 8604141Abstract: Ruthenium and osmium carbene compounds that are stable in the presence of a variety of functional groups and can be used to catalyze olefin metathesis reactions on unstrained cyclic and acyclic olefins are disclosed. Also disclosed are methods of making the carbene compounds. The carbene compounds are of the formula where M is Os or Ru; R1 is hydrogen; R is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, and substituted or unsubstituted aryl; X and X1 are independently selected from any anionic ligand; and L and L1 are independently selected from any neutral electron donor. The ruthenium and osmium carbene compounds of the present invention may be synthesized using diazo compounds, by neutral electron donor ligand exchange, by cross metathesis, using acetylene, using cumulated olefins, and in a one-pot method using diazo compounds and neutral electron donors.Type: GrantFiled: April 24, 2012Date of Patent: December 10, 2013Assignee: California Institute of TechnologyInventors: Robert H. Grubbs, Peter Schwab, Sonbinh T. Nguyen
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Patent number: 8586812Abstract: Processes for upgrading condensate in a first hydrocarbon stream to provide distillate material may involve ionic liquid catalyzed olefin oligomerization of olefins in the first hydrocarbon stream to provide a first distillate enriched stream, dechlorination of the first distillate enriched stream, hydroprocessing at least one of a second and a third hydrocarbon stream to provide a second distillate enriched stream, and separation of a distillate product from the first and second distillate enriched streams.Type: GrantFiled: December 22, 2010Date of Patent: November 19, 2013Assignee: Chevron U.S.A. Inc.Inventors: Hye-Kyung C. Timken, Bi-Zeng Zhan
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Publication number: 20130303818Abstract: A method for producing an unsaturated dimer by reacting an ?-olefin having 6 to 14 carbon atoms in an agitated vessel, wherein a metallocene-based catalyst is used as a reaction catalyst; and the supply flow rate of hydrogen (VH) to the vessel is 0.2 to 1.2 [(NL/hr) per L of olefin] and the agitation power (Pv) is 0.18 KW/m3 or more of the time of reaction.Type: ApplicationFiled: January 11, 2012Publication date: November 14, 2013Applicant: IDEMITSU KOSAN CO., LTD.Inventors: Junichi Inagaki, Masashi Machida, Masaki Okano, Minako Tsuji
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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