By Displacement Of Hydrocarbon Radical By Hydrocarbon Molecule Patents (Class 585/637)
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Patent number: 8299313Abstract: A process is provided which is capable of producing olefins stably and efficiently by a metathesis reaction of identical or different olefins while preventing the lowering in metathesis catalyst activity due to trace impurities such as heteroatom-containing compounds that are contained in a starting olefin. The olefin production process includes supplying a starting olefin containing more than 0 ppm by weight to not more than 10 ppm by weight of one or more kinds of heteroatom-containing compounds to a reactor that contains a metathesis catalyst and an isomerization catalyst, the metathesis catalyst including at least one metal element selected from the group consisting of tungsten, molybdenum and rhenium, the isomerization catalyst including calcined hydrotalcite or yttrium oxide, and performing a metathesis reaction of identical or different olefins.Type: GrantFiled: August 27, 2009Date of Patent: October 30, 2012Assignee: Mitsui Chemicals, Inc.Inventors: Toshihiro Takai, Hirokazu Ikenaga, Makoto Kotani, Satoru Miyazoe
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Patent number: 8026403Abstract: A method for producing a product comprising at least one selected from C2+ hydrocarbons, oxygenates, and combinations thereof from light gas comprising one or more of carbon dioxide, methane, ethane, propane, butane, pentane, and methanol by forming a dispersion of light gas in a liquid feed, wherein the dispersion is formed at least in part with high shear forces and wherein at least one of the liquid feed and the light gas is a hydrogen source. A system for carrying out the method is also presented.Type: GrantFiled: June 17, 2008Date of Patent: September 27, 2011Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Publication number: 20110152595Abstract: A process is provided which is capable of producing olefins stably and efficiently by a metathesis reaction of identical or different olefins while preventing the lowering in metathesis catalyst activity due to trace impurities such as heteroatom-containing compounds that are contained in a starting olefin. The olefin production process includes supplying a starting olefin containing more than 0 ppm by weight to not more than 10 ppm by weight of one or more kinds of heteroatom-containing compounds to a reactor that contains a metathesis catalyst and an isomerization catalyst, the metathesis catalyst including at least one metal element selected from the group consisting of tungsten, molybdenum and rhenium, the isomerization catalyst including calcined hydrotalcite or yttrium oxide, and performing a metathesis reaction of identical or different olefins.Type: ApplicationFiled: August 27, 2009Publication date: June 23, 2011Applicant: MITSUI CHEMICALS, INC.Inventors: Toshihiro Takai, Hirokazu Ikenaga, Makoto Kotani, Satoru Miyazoe
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Patent number: 6444867Abstract: Linear alpha olefins are typically produced by starting with a trialkylaluminum compound, such as triethylaluminum, and then subjecting the trialkylaluminum compound to alkyl chain growth conditions in the presence of ethylene and elevated temperature and pressure, frequently in the presence of a chain growth catalyst. Under such alkyl chain growth conditions, the alkyl groups attached to the aluminum may be extended by two carbon atoms per reaction with ethylene. The process is permitted to continue until the alkyl groups have reached the desired length at which point they are displaced from the trialkylaluminum compund as alpha olefins, usually in the presence of an excess of ethylene and a displacement catalyst. This invention discloses a new chain growth catalyst system comprising, in combination, non-bridged metallocenes and aluminum complexes having amidinate ligands and inert anions.Type: GrantFiled: May 17, 2001Date of Patent: September 3, 2002Assignee: BP Corporation North America Inc.Inventors: Edward G. Samsel, Franke N. Brooks
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Patent number: 6258988Abstract: A method is disclosed for reforming organics into shorter-chain unsaturated organic compounds. A molten metal bath is provided which can cause homolytic cleavage of an organic component of an organic-containing feed. The feed is directed into the molten metal bath at a rate which causes partial homolytic cleavage of an organic component of the feed. Conditions are established and maintained in the reactor to cause partial homolytic cleavage of the organic component to produce unsaturated organic compounds, as products of the homolytic cleavage, which are discharged from the molten metal bath.Type: GrantFiled: December 23, 1993Date of Patent: July 10, 2001Assignee: Quantum Catalytics, L.L.C.Inventors: Christopher J. Nagel, Thomas P. Griffin, Thomas A. Kinney, Kevin A. Sparks
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Patent number: 5898091Abstract: For the conversion of an olefinic C.sub.4 or C.sub.5 cut to an alkyl-tertiobutylether or alkyl-tertioamylether and to propylene, by metathesis, the process comprises four successive steps: (1) selective hydrogenation of the diolefins with simultaneous isomerisation of the alpha olefins to internal olefins; (2) etherification of the isoolefins; (3) elimination of oxygen-containing impurities; (4) metathesis of internal olefins with ethylene. The process has application, e.g., to C.sub.4 and C.sub.5 steam cracking cuts.Type: GrantFiled: May 10, 1996Date of Patent: April 27, 1999Assignee: Institut Francais du PetroleInventors: Jean-Alain Chodorge, Dominique Commereuc, Jean Cosyns, Didier Duee, Bernard Torck
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Patent number: 5877378Abstract: The alpha-olefin content of mixed hydrocarbon streams is selectively utilized to produce trialkylaluminum compounds in which the alkyl groups are linear primary alkyl groups. This selective utilization is accomplished by use of a specific, highly selective low residence-time, low isomerization catalytic displacement reaction. In addition, when alpha-olefins are the desired end product, a second low residence-time catalytic displacement reaction is utilized whereby high purity alpha olefins are produced.Type: GrantFiled: September 15, 1997Date of Patent: March 2, 1999Assignee: Amoco CorporationInventors: Andrew D. Overstreet, Robert H. Allen, Larry H. Nemec, Ronny W. Lin
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Patent number: 5817902Abstract: The invention provides a process for making .alpha.-olefins. In the chain growth reaction step of the process a jet loop reactor is used to fully use high pressure ethylene, and two or more stages of the chain growth reaction is used to raise the selectivity of C.sub.6-10 olefins.Type: GrantFiled: November 12, 1996Date of Patent: October 6, 1998Assignees: China Petro-Chemical Corporation, Daqing Petrochemical Works, China Petrochemical CorporationInventors: Minghe Xie, Anshun Sun, Daohua Jiang, Jiabo Qu, Qian Chen, Weibin Li, Zongsheng Yuan, Chunmei Yu, Xixia Song, Shubao Wan, Zhengnian Luo, Fengrong Wang, Qun Xu, Shulan Wang, Yingjie Feng, Yongchen Sun
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Patent number: 5780697Abstract: A process for deactivating a nickel, cobalt, or nickel and cobalt displacement catalyst during a reaction wherein an alkyl group is displaced from a trialkyl aluminum compound in a reaction mixture containing said catalyst is disclosed. The process involves adding a deactivating amount of a catalyst poison containing silver, silver compounds, silver complexes, thallium, thallium compounds, thallium complexes, or mixtures thereof to the reaction mixture after the displacement has proceeded to the desired extent.Type: GrantFiled: June 17, 1997Date of Patent: July 14, 1998Assignee: Amoco CorporationInventors: Ronny Wen-Long Lin, Richard Andrew Holub, Richard Neil Hollenshead
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Patent number: 5731480Abstract: A process is described for coproducing vinylidene alcohol and vinylidene olefin. The process involves dimerizing one or more vinylolefins with an alkyl aluminum catalyst to form a first product mixture comprising at least vinylidene olefin and alkyl aluminum compound. The vinylidene olefin is then reacted with the alkyl aluminum compound under displacement conditions to form 1-olefin while concurrently removing the 1-olefin from the displacement reaction mixture to form a second product mixture comprising at least beta-branched alkyl aluminum compound. The second product mixture is treated with air or oxygen under mild oxidation conditions to form a third product mixture comprising at least beta-branched aluminum alkoxide. The beta-branched aluminum alkoxide is then hydrolyzed to form vinylidene alcohol. The process makes effective use of the alkyl aluminum catalyst both as a catalyst and as a reactant, and requires only a relatively small amount of reaction equipment.Type: GrantFiled: November 3, 1995Date of Patent: March 24, 1998Assignee: Albemarle CorporationInventor: Kaung-Far Lin
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Patent number: 5550303Abstract: Olefin is formed by displacing alkyl groups of aluminum trialkyl by contacting ethylene with the aluminum trialkyl in an ethylene:aluminum trialkyl mol ratio in the range of 2-8:1 at about 0.degree.-70.degree. C. and at atmospheric up to about 1000 psia pressure, for a reaction time of about 0.5 to about 60 minutes in the presence of a displacement enhancing amount of a nickel- or cobalt-containing displacement catalyst. Despite the fact that the displacement reaction is an equilibrium reaction, the process does not use, as did the prior art, large excesses of ethylene to shift the equilibrium to favor displacement. Consequently, the volumes of ethylene used in the processing are reduced very substantially and yet yields of the desired displaced alpha olefin remain favorable.Type: GrantFiled: June 2, 1995Date of Patent: August 27, 1996Assignee: Amoco CorporationInventors: Ronny W. Lin, Robert H. Allen, Andrew D. Overstreet
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Patent number: 5536859Abstract: This invention provides an improved process for the preparation of an aluminum alkyl chain growth product by the chain growth reaction of alpha-olefins on aluminum alkyl, the improvement comprising catalyzing the chain growth reaction that is a partially oxidized aluminum alkyl.Type: GrantFiled: February 27, 1995Date of Patent: July 16, 1996Assignee: Amoco CorporationInventors: Kaung-Far Lin, Carroll W. Lanier, William B. Waites
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Patent number: 5276220Abstract: An improved process for preparing an alkyl chain growth product by the chain growth reaction of .alpha.-olefin in an aluminum alkyl uses a catalyst system which comprises an actinide metallocene.Type: GrantFiled: June 18, 1992Date of Patent: January 4, 1994Assignee: Ethyl CorporationInventors: Edward G. Samsel, David C. Eisenberg
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Patent number: 5210338Abstract: An improved process for the preparation of higher aluminum alkyls by a chain growth reaction of an .alpha.-olefin and especially ethylene with a lower molecular weight aluminum alkyl or aluminum hydride uses a catalyst system which comprises at least one of (a) a metallocene of a transition metal and an aluminoxane (b) a cationic transition metal metallocene complex with an inert, non-coordinating anion, and (c) a cationic transition metal metallocene complex with an inert, non-coordinating anion and a hydrocarbylaluminoxane. Higher purity alpha olefins can be recovered by olefin displacement. Alternatively, linear primary alcohols can be produced by oxidation and hydrolysis.Type: GrantFiled: May 12, 1992Date of Patent: May 11, 1993Assignee: Ethyl CorporationInventor: Edward G. Samsel
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Patent number: 5144053Abstract: Linear 1-olefins are prepared from internal olefins by (i) reacting them in the presence of an isomerization catalyst and a tri-lower alkyl aluminum so as to cause internal olefin to isomerize to 1-olefins which displace the lower alkyl groups to form a trialkyl aluminum compound in which at least one of the alkyl groups is a linear alkyl derived from the 1-olefin, and, thereafter, (ii) reacting the trialkyl aluminum compound with a 1-olefin so as to displace the linear alkyl from the trialkyl aluminum compound, thereby forming a linear 1-olefin product which is substantially free of internal olefins.Type: GrantFiled: December 9, 1991Date of Patent: September 1, 1992Assignee: Ethyl CorporationInventors: Robert H. Allen, Keith G. Anderson, Steven P. Diefenbach, Ronny W. Lin, Larry H. Nemec, Andrew D. Overstreet, Gene C. Robinson
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Patent number: 4918254Abstract: Alkyl groups in trialkyl aluminum are displaced by .alpha.-olefins in the presence of a nickel catalyst. The displaced alkyl group evolve as .alpha.-olefins. The displacement is fast and the catalyst is then poisoned with a catalyst poison such as lead to prevent undesired side reactions such as isomerization of .alpha.-olefins to internal olefins or dimerization to vinylidene olefins.Type: GrantFiled: February 6, 1989Date of Patent: April 17, 1990Assignee: Ethyl CorporationInventors: Steven P. Diefenbach, Gene C. Robinson
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Patent number: 4484016Abstract: Butene-1 and ethylene mixtures are made by reacting ethylene with a trialkyl aluminum in a boiling bed reactor. The process is more efficient in that it is selective for making butene-1 and more butene-1 is produced per unit weight of the trialkyl aluminum.Type: GrantFiled: July 5, 1983Date of Patent: November 20, 1984Assignee: The Dow Chemical CompanyInventors: Donald M. Maschmeyer, Allan E. Fowler, Steve A. Sims, G. Eldon White
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Patent number: 4455289Abstract: A combined process for preparing alumina and alpha-olefins (.alpha.-olefins) is disclosed. The process comprises:(a) reacting tri-(C.sub.2 to C.sub.24) alkylaluminum with ethylene in the presence of nickel catalyst to form triethylaluminum and C.sub.2 to C.sub.24 .alpha.-olefins,(b) adding aluminum tri-(C.sub.4 to C.sub.8) alcoholate to the reaction product of step (a),(c) equilibrating the admixture of step (b) so that substantially all of the triethylaluminum is converted into aluminum ethyl alcoholates, compounds with at least one C.sub.4 to C.sub.8 alcoholate group per molecule,(d) subjecting the equilibrated mixture of step (c) to a fractionation to recover, (1) a C.sub.2 to C.sub.24 .alpha.-olefin fraction, and (2) an aluminum ethyl alcoholate fraction (a mixture of compounds with the general formula Al(C.sub.2 H.sub.6).sub.X (OC.sub.6 H.sub.13).sub.Y (where X is 0 to 2 and Y is 3 to 1) and X+Y=3).(e) adding C.sub.4 to C.sub.8 alcohol to the aluminum ethyl alcoholate fraction to form aluminum tri-(C.Type: GrantFiled: August 6, 1982Date of Patent: June 19, 1984Assignee: Conoco Inc.Inventors: R. L. Poe, D. J. Royer
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Patent number: 4380684Abstract: A method for preparing C.sub.4 to C.sub.10 .alpha.-olefins employing trialkyl aluminum compounds, in a growth zone having a recirculation rate through an external heat transfer zone such that the contents of the zone are recirculated in a period of time sufficient to remove the heat of the reaction using added lower .alpha.-olefins at 100.degree.-150.degree. C., 200-2000 psig, and 5-90 minute contact time followed by displacement with lower .alpha.-olefins in a static mixer zone to free the growth .alpha.-olefins and regenerate the trialkyl aluminum compounds. The growth .alpha.-olefins are separated with all of the lower .alpha.-olefins recycled to the growth and displacement steps.Type: GrantFiled: April 19, 1982Date of Patent: April 19, 1983Assignee: The Dow Chemical CompanyInventors: Allan E. Fowler, Gordon E. White, Steve A. Sims
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Patent number: 4314090Abstract: A method for preparing C.sub.4 to C.sub.10 .alpha.-olefins having a major portion C.sub.6 .alpha.-olefins employing tri alkyl aluminum compounds, e.g., Al(C.sub.2 H.sub.5).sub.3 or Al(C.sub.4 H.sub.9).sub.3 or mixtures of Al(C.sub.2 H.sub.5).sub.3 and Al(C.sub.4 H.sub.9).sub.3 as well as the unmixed C.sub.2, C.sub.4 alkyl aluminum isomers or homologs in the growth step using added ethylene at about 120.degree. C., 500-700 psig, 5-90 minute contact time followed by displacement with C.sub.2 H.sub.4, C.sub.4 H.sub.8, or C.sub.2 H.sub.4 and C.sub.4 H.sub.8 to free the growth alkyl and regenerate the tri alkyl aluminum compounds. The growth .alpha.-olefins are separated with all of the C.sub.2 H.sub.4 recycled to the growth and displacement steps, and part or all of the C.sub.4 H.sub.8 recycled to the displacement step.Type: GrantFiled: August 18, 1980Date of Patent: February 2, 1982Assignee: The Dow Chemical CompanyInventors: William E. Shewbart, Steve A. Sims, Billy D. Head, G. Eldon White
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Patent number: RE42832Abstract: A method is disclosed for reforming organics into shorter-chain unsaturated organic compounds. A molten metal bath is provided which can cause homolytic cleavage of an organic component of an organic-containing feed. The feed is directed into the molten metal bath at a rate which causes partial homolytic cleavage of an organic component of the feed. Conditions are established and maintained in the reactor to cause partial homolytic cleavage of the organic component to produce unsaturated organic compounds, as products of the homolytic cleavage, which are discharged from the molten metal bath.Type: GrantFiled: July 10, 2003Date of Patent: October 11, 2011Assignee: Quantum Catalytics, L.L.C.Inventors: Christopher J. Nagel, Thomas P. Griffin, Thomas A. Kinney, Kevin A. Sparks