By Double-bond-shift Isomerization Patents (Class 585/664)
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Patent number: 11932597Abstract: A process for converting isobutane to propylene. The process including dehydrogenating isobutane to produce a mixed product stream comprising isobutane and isobutene, skeletal isomerizing the mixed product stream comprising isobutane and isobutene to convert isobutene to n-butenes including 1-butene and 2-butenes and to recover a skeletal isomerization reaction product comprising isobutane, isobutene, butadiene, 1-butene, and 2-butenes. The process further including fractionating the skeletal isomerization reaction product, isomerizing the 1-butene contained therein to 2-butenes, recovering an overhead fraction comprising isobutane, a side draw fraction comprising isobutane and isobutene, and a bottoms fraction comprising 2-butenes, and combining the bottoms fraction with ethylene and converting the ethylene and 2-butenes to produce a reaction effluent comprising propylene.Type: GrantFiled: March 10, 2023Date of Patent: March 19, 2024Assignee: LUMMUS TECHNOLOGY LLCInventors: Martinus J. Almering, Kerman N. Dukandar, Oliver Chen
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Patent number: 11827589Abstract: Methods of converting isobutylene to C5+ compounds. The methods may include contacting isobutylene with a skeletal isomerization catalyst to provide a mixture of C4 olefins, and then contacting the mixture of C4 olefins with a metathesis catalyst to convert the mixture of C4 olefins to a product mixture. The product mixture may include C5+ olefins.Type: GrantFiled: September 23, 2022Date of Patent: November 28, 2023Assignee: Lyondell Chemical Technology, L.P.Inventors: Linn Fang, Daniel F. White, Lei Zhang
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Patent number: 11332420Abstract: Processes are described for isomerizing one or more C14-C24 alpha olefins to produce an isomerization mixture comprising one or more C14-C24 internal olefins comprising contacting an olefinic feed comprising the one or more C14-C24 alpha olefins with a catalyst under isomerization conditions, wherein the catalyst comprises a microporous crystalline aluminosilicate having an MWW framework. The resulting isomerization mixture typically exhibits a low pour point with maintained biodegradability properties as compared to the olefinic feed, and is particularly useful in drilling fluid and paper sizing compositions.Type: GrantFiled: December 4, 2018Date of Patent: May 17, 2022Assignee: ExxonMobil Chemical Patents Inc.Inventors: Ronald Raymond Hill, Jr., Renyuan Yu, Elizabeth G. Mahoney, Anatoly I. Kramer, Wenyih F. Lai, Paul F. Keusenkothen, Nan Hu, Andrew P. Broenen, James R. Lattner
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Patent number: 10308566Abstract: Provided are a separation system for easily recovering normal butene from an olefin fraction including isobutene, isobutane, 1-butene, 2-butene, and normal butane, and a separation process system using the method. Since the separation system may easily convert 1-butene included in the olefin fraction to 2-butene, normal butene may be effectively separated and recovered by factional distillation and each recovered fraction may be easily refluxed even if the use of a reflux system using a refrigerant is reduced or excluded. Thus, economic efficiency may be improved and simultaneously, separation efficiency may be increased.Type: GrantFiled: January 17, 2019Date of Patent: June 4, 2019Assignee: LG CHEM, LTD.Inventors: Dae Hyeon Kim, Soo Hwan Hwang, Jong Ku Lee, Jeong Seok Lee
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Patent number: 10294564Abstract: A method for forming boron (B) containing Al2O3 composite layers includes (a) reacting a substrate surface with an aluminum-containing precursor to form a first monolayer, (b) purging excess aluminum-containing precursor and reaction by-product, (c) reacting the first monolayer with a second precursor, and (d) purging excess second precursor and reaction by-product, such that steps (a) to (d) constitute one cycle, the composite layers being formed after a plurality of cycles, and the resultant composite layers have a chemical formula of BxAl2?xO3, where x varies in the range of 0 and 2.Type: GrantFiled: August 28, 2017Date of Patent: May 21, 2019Assignee: UChicago Argonne, LLCInventors: Anil U. Mane, Jeffrey W. Elam
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Patent number: 9683060Abstract: Disclosed is a method for preparing a highly reactive polybutene of high quality having low fluorine content and high vinylidene content at high mileage of catalyst with economy. The method for preparing a polybutene includes: performing a selective hydrogenation reaction of diolefin among C4 hydrocarbon components produced from petroleum refineries or naphtha cracking centers, which involve cracking of crude oils, and simultaneously an isomerization reaction of 1-butene to 2-butene and then isolating an isobutene feedstock through fractional distillation; and polymerizing the isobutene feedstock obtained by the fractional distillation.Type: GrantFiled: July 16, 2015Date of Patent: June 20, 2017Assignee: DAELIM INDUSTRIAL CO., LTD.Inventors: Myeong Seok Kim, Min Sup Park, Hyung Jae Seo, Se Hyun Lee
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Patent number: 9040764Abstract: A process for the double-bond isomerization of olefins is disclosed. The process may include contacting a fluid stream comprising olefins with a fixed bed comprising an activated basic metal oxide isomerization catalyst to convert at least a portion of the olefin to its isomer. The isomerization catalysts disclosed herein may have a reduced cycle to cycle deactivation as compared to conventional catalysts, thus maintaining higher activity over the complete catalyst life cycle.Type: GrantFiled: November 11, 2013Date of Patent: May 26, 2015Assignee: Lummus Technology Inc.Inventors: Bala Ramachandran, Sukwon Choi, Robert J. Gartside, Marvin I. Greene
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Patent number: 8933284Abstract: Processes are provided for the production of butadiene from C4 containing feed stocks that contain isobutene and/or isobutane in addition to n-butene(s) and/or n-butane. The processes of the present invention generally comprise feeding the feed stock to a combination butenes isomerization reaction and distillation tower for conversion of 1-butene to 2-butenes and separation from isobutene and isobutane, followed by an oxydehydrogenation unit to convert n-butenes to butadiene. The processes may also include additional isomerization and/or dehydrogenation steps for the tower overhead and bottoms streams to create additional isobutene and/or n-butenes for valued/uses, which may include additional production of butadiene. The feed to the system may comprise any mixture or separate feeding of C4 olefins and C4 paraffins, at least one of which contains isobutene and/or isobutane.Type: GrantFiled: October 17, 2012Date of Patent: January 13, 2015Assignee: Lummus Technology Inc.Inventors: Stephen Craig Arnold, Anne Mae Gaffney, Lawrence John Karas, Philip Jay Angevine, Chuen Yuan Yeh, Ruozhi Song
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Patent number: 8772196Abstract: Disclosed is a composition useful in the saturation of aromatics contained in a hydrocarbon feedstock. The composition includes a support composition having a high macroporosity of greater than 51 percent. The support composition comprises an amorphous silica-alumina having unique properties.Type: GrantFiled: August 25, 2008Date of Patent: July 8, 2014Assignee: Shell Oil CompanyInventors: Russell Craig Ackerman, Christian Gabriel Michel, John Anthony Smegal, Johannes Anthonius Robert Van Veen
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Publication number: 20140171677Abstract: A method of isomerizing a substance includes combining a substance including a terminal alkenyl group and a substance including a fluorosulfonic acid group in a reaction mixture, and forming a substance including a 2-alkenyl group from the substance including a terminal alkenyl group in the reaction mixture. The method may be used to functionalize a substance, as the substance including a 2-alkenyl group can be reacted with a functionalizing agent to form a substance including a first functional group. The methods may be used to form a dicarboxylic acid, such as suberic acid, from a renewable feedstock.Type: ApplicationFiled: November 26, 2013Publication date: June 19, 2014Applicant: Elevance Renewable Sciences, Inc.Inventors: Paul A. Bertin, Jordan R. Quinn
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Patent number: 8742186Abstract: Described herein is a process for producing an alpha olefin by obtaining a feed stream of internal olefins having a first carbon number and alpha olefins having a first carbon number. The olefins are isomerized to increase the quantity of the alpha olefins. The olefins are then fractionated, subjecting the overhead material to catalytic metathesis to produce a mixed olefin effluent of internal olefins having a second carbon number and other hydrocarbons. The first isomerization reactor and fractionator are prepared to receive the olefins having a second carbon number, where the internal olefin intermediate is isomerized in the prepared first isomerization reactor. The second isomerization effluent is fractionated in the prepared first fractionator to separate the alpha olefins having the second carbon number from the internal olefins having the second carbon number. A corresponding system is also described, along with a heat pump that may be incorporated into the process.Type: GrantFiled: April 2, 2009Date of Patent: June 3, 2014Assignee: Lummus Technology Inc.Inventors: Robert J. Gartside, Shaun M. McGovern, Thulasidas Chellppannair
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Patent number: 8624075Abstract: Process for isomerizing linear alpha-olefins having from 10 to 25 carbon atoms over a heterogeneous catalyst.Type: GrantFiled: December 20, 2010Date of Patent: January 7, 2014Assignee: BASF SEInventors: Lucia Königsmann, Ekkehard Schwab, Thilo Hahn, Germain Kons
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Patent number: 8586813Abstract: A process for the double-bond isomerization of olefins is disclosed. The process may include contacting a fluid stream comprising olefins with a fixed bed comprising an activated basic metal oxide isomerization catalyst to convert at least a portion of the olefin to its isomer. The isomerization catalysts disclosed herein may have a reduced cycle to cycle deactivation as compared to conventional catalysts, thus maintaining higher activity over the complete catalyst life cycle.Type: GrantFiled: July 21, 2009Date of Patent: November 19, 2013Assignee: Lummus Technology Inc.Inventors: Bala Ramachandran, Sukwon Choi, Robert J. Gartside, Marvin I. Greene
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Patent number: 8440874Abstract: A process for the production of propylene, the process including: contacting ethylene and a hydrocarbon stream comprising 1-butene and 2-butene with a bifunctional isomerization-metathesis catalyst to concurrently isomerizes 1-butene to 2-butene and to form a metathesis product comprising propylene; wherein the bifunctional isomerization-metathesis catalyst comprises: a catalyst compound may include at least one element selected from tungsten, tantalum, niobium, molybdenum, nickel, palladium, osmium, iridium, rhodium, vanadium, ruthenium, and rhenium for providing metathesis activity on a support comprising at least one element from Group IA, IIA, IIB, and IIIA of the Periodic Table of the Elements; wherein an exposed surface area of the support provides both isomerization activity for the isomerization of 1-butene to 2-butene; and reactive sites for the adsorption of catalyst compound poisons.Type: GrantFiled: September 4, 2009Date of Patent: May 14, 2013Assignees: Lummus Technology Inc., BASF CorporationInventors: Bala Ramachandran, Sukwon Choi, Robert J. Gartside, Shane Kleindienst, Wolfgang Ruettinger, Saeed Alerasool
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Patent number: 8435920Abstract: Processes are disclosure which comprise alternately contacting an oxygen-carrying catalyst with a reducing substance, or a lower partial pressure of an oxidizing gas, and then with the oxidizing gas or a higher partial pressure of the oxidizing gas, whereby the catalyst is alternately reduced and then regenerated to an oxygenated state. In certain embodiments, the oxygen-carrying catalyst comprises at least one metal oxide-containing material containing a composition having the following formulas: (a) CexByB?zB?O?, wherein B=Ba, Sr, Ca, or Zr; B?=Mn, Co, and/or Fe; B?=Cu; 0.01<x<0.99; 0<y<0.6; 0<z<0.5; (b) Ce1-x-yNixByO2-*, wherein B=Zr, Ba, Ca, La, or K; 0.02<x<0.1; 0<y<0.1; and 0.02<*<0.15; and 1<?<2.2 and (c) coal ash either as a catalyst material itself or as a support for said unary or binary metal oxides.Type: GrantFiled: October 11, 2010Date of Patent: May 7, 2013Assignee: Eltron Research & Development, Inc.Inventors: James H. White, Erick J. Schutte, Sara L. Rolfe
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Patent number: 8395005Abstract: A process for producing propylene and 1-butene is disclosed. The process comprises dimerizing ethylene in the presence of a dimerization catalyst to produce a dimerization mixture comprising 1-butene and 2-butenes. The dimerization mixture is distilled to produce a 1-butene stream containing 1-butene and ethylene, a 2-butenes stream, and a heavy stream. The 2-butenes stream is reacted with ethylene in the presence of a metathesis catalyst to produce a metathesis mixture comprising propylene, ethylene, and 2-butenes. Propylene is separated from the metathesis mixture.Type: GrantFiled: October 13, 2010Date of Patent: March 12, 2013Assignees: Equistar Chemicals, LP, Lyondell Chemical Technology, L.P.Inventors: Steven T. Coleman, Gary A. Sawyer, Robert S. Bridges
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Patent number: 8389790Abstract: The present invention relates to isomerization of Z-lycopene in mixtures of isomers to mixtures enriched with all E-lycopene.Type: GrantFiled: April 6, 2011Date of Patent: March 5, 2013Assignee: Divi's Laboratories, Ltd.Inventors: Murali Krishna Prasad Divi, Gundu Rao Padakandla, Nageswara Rao Bolneni, Ramesh Babu Kodali
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Patent number: 8314278Abstract: Disclosed herein is a process for producing isoprene that includes reacting a mixed C4 metathesis feed stream comprising isobutylene and at least one of 1-butene and 2-pentene in a first metathesis reactor in the presence of a first metathesis catalyst under conditions sufficient to produce an intermediate product stream comprising at least 30 wt. % 2-methyl-2-pentene based upon the olefin content of fresh feed in the mixed C4 feed stream, and at least one of ethylene and propylene, separating the 2-methyl-2-pentene, subjecting the separated 2-methyl-2-pentene to pyrolysis to produce a reaction product stream comprising isoprene, and separating the isoprene into an isoprene product stream using fractionation. A system used in producing isoprene is also disclosed.Type: GrantFiled: May 8, 2012Date of Patent: November 20, 2012Assignee: Lummus Technology Inc.Inventors: Robert J Gartside, Shane R Kleindienst
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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: 8293960Abstract: Processes are provided for the production of butadiene from C4 containing feed stocks that contain isobutene and/or isobutane in addition to n-butene(s) and/or n-butane. The processes of the present invention generally comprise feeding the feed stock to a combination butenes isomerization reaction and distillation tower for conversion of 1-butene to 2-butenes and separation from isobutene and isobutane, followed by an oxydehydrogenation unit to convert n-butenes to butadiene. The processes may also include additional isomerization and/or dehydrogenation steps for the tower overhead and bottoms streams to create additional isobutene and/or n-butenes for valued uses, which may include additional production of butadiene. The feed to the system may comprise any mixture or separate feeding of C4 olefins and C4 paraffins, at least one of which contains isobutene and/or isobutane.Type: GrantFiled: August 17, 2009Date of Patent: October 23, 2012Assignee: Lummus Technology Inc.Inventors: Stephen Craig Arnold, Anne Mae Gaffney, Lawrence John Karas, Philip Jay Angevine, Chuen Yuan Yeh, Ruozhi Song
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Patent number: 8178736Abstract: Disclosed herein is a process for producing isoprene that includes reacting a mixed C4 metathesis feed stream comprising isobutylene and at least one of 1-butene and 2-pentene in a first metathesis reactor in the presence of a first metathesis catalyst under conditions sufficient to produce an intermediate product stream comprising at least 30 wt. % 2-methyl-2-pentene based upon the olefin content of fresh feed in the mixed C4 feed stream, and at least one of ethylene and propylene, separating the 2-methyl-2-pentene, subjecting the separated 2-methyl-2-pentene to pyrolysis to produce a reaction product stream comprising isoprene, and separating the isoprene into an isoprene product stream using fractionation. A system used in producing isoprene is also disclosed.Type: GrantFiled: August 7, 2009Date of Patent: May 15, 2012Assignee: Lummus Technology Inc.Inventors: Robert J Gartside, Shane R Kleindienst
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Patent number: 8178737Abstract: A process for producing propylene from ethylene and a feed stream comprising 1-butene, 2-butene, n-butane, and isobutane is disclosed. A butenes stream (1-butene and 2-butene) is produced from the feed stream by removing the paraffins. The butenes stream is reacted in the presence of an isomerization catalyst to produce an isomerized stream with increased concentration of 2-butene. The isomerized stream is reacted with ethylene in the presence of a metathesis catalyst to produce a reaction mixture comprising propylene; the propylene may be isolated from the reaction mixture by distillation. The removal of paraffins from the feed stream improves the catalyst productivity and the plant throughput.Type: GrantFiled: June 14, 2007Date of Patent: May 15, 2012Assignee: Lyondell Chemical Technology, L.P.Inventor: David W. Leyshon
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Patent number: 8148593Abstract: This invention relates to a process for converting a hydrocarbon feedstock, comprising the steps of (A) feeding the feedstock to a reactor or adsorption unit; (B) contacting the feedstock in the reactor or adsorption unit with a solid particulate material useful for converting the feedstock under conversion conditions; (C) withdrawing converted feedstock from the reactor; and (D) removing, under the conversion conditions for a fractional time of step (B), at least a portion of the solid particulate material while the feedstock is being fed to the reactor or adsorption unit, wherein the portion is more than 0.1 wt. % of the solid particulate material in the reactor or adsorption unit and wherein the fractional time is less than 95% of the time of step (B).Type: GrantFiled: November 11, 2009Date of Patent: April 3, 2012Assignee: ExxonMobil Chemical Patents Inc.Inventors: Dana Lynn Pilliod, Katy Conley Randall, Eric Martin Harding
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Patent number: 8084659Abstract: Embodiments disclosed herein provide processes for upgrading the hexene stream to valuable end products, including ethers, high purity 1-hexene, and, alternatively, high purity isohexene. Hexene upgrading may be performed in embodiments disclosed herein by first removing isohexene from the admixture. The isohexene may undergo etherification with one or more alcohols, facilitating the separation of the isohexene (in the form of an ether) from the normal hexenes. Second, the normal hexenes may be isomerized to convert internal hexene olefins (2-hexenes and 3-hexenes) to the desired alpha olefin, 1-hexene. The 1-hexene may then be separated from unreacted components to yield a high purity 1-hexene product.Type: GrantFiled: October 21, 2009Date of Patent: December 27, 2011Inventors: Robert J. Gartside, Thulasidas Chellppannair
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Patent number: 7982086Abstract: A process for fractionating isobutene from normal butenes, including: introducing hydrogen and a feed stream comprising isobutene, 1-butene, and 2-butene into a first column including a reaction zone containing a hydroisomerization catalyst operating at a first pressure and concurrently: (i) converting at least a portion of the 1-butene to 2-butene, and (ii) separating isobutene from the 2-butene; recovering a first overheads fraction comprising isobutene from the first column; recovering a first bottoms fraction comprising isobutene, 2-butene, and unreacted 1-butene from the first column; introducing the first bottoms fraction into a top portion of a second column comprising a fractionation column operating at a second pressure lower than the first pressure; separating the first bottoms into a second overheads fraction comprising isobutene and 1-butene and a second bottoms fraction comprising 2-butene; compressing the second overheads fraction; and introducing the compressed second overheads fraction to a loType: GrantFiled: February 3, 2009Date of Patent: July 19, 2011Assignee: Catalytic Distillation TechnologiesInventor: Martinus J. Almering
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Patent number: 7960599Abstract: A process for producing industrially important chemicals from renewable resources is disclosed. This “biobased” process employs readily available, renewable resources comprising fatty acids rather than exploiting fossil sources, such as coal and petroleum. In one embodiment of the process 1-octene, along with methyl-9-decenoate and butadiene, is produced from linoleic acid via an enzymemediated isomerization reaction, followed by a metathesis reaction with ethylene. Linoleic acid can be isolated from vegetable oils, such as soybean oil.Type: GrantFiled: January 13, 2004Date of Patent: June 14, 2011Assignee: Elevance Renewable Sciences, Inc.Inventors: James R. Millis, Michael J. Tupy, Timothy W. Abraham, Mervyn L. De Souza
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Patent number: 7956229Abstract: A method for producing an internal olefin by stably isomerizing an ?-olefin by using an inexpensive zeolite catalyst while preventing an oligomerization reaction is provided. The method for producing an internal olefin comprises a step of isomerizing an ?-olefin having from 16 to 18 carbon atoms by passing through a zeolite catalyst bed, wherein the ?-olefin having from 16 to 18 carbon atoms is circulated through and brought into contact with the zeolite catalyst bed before starting the isomerization reaction.Type: GrantFiled: December 28, 2005Date of Patent: June 7, 2011Assignee: Idemitsu Kosan Co., Ltd.Inventors: Tetsuya Saruwatari, Hideki Yamane
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Patent number: 7939703Abstract: The present invention relates to methods for accelerating the trans-cis isomerization of 1,2-diphenylethylene analogues by using photocatalyst. According to this invention, in the presence of polypyridyl platinum(II) complex with catalytic dosage, a solution containing trans-1,2-diphenylethylene analogues or mixture of cis- and trans-1,2-diphenylethylene analogues is irradiated by visible light to prepare product of cis-1,2-diphenylethylene analogues or product predominantly being cis-1,2-diphenylethylene analogues under inert gas atmosphere. This method has the advantages of fast reaction, high performance, easy separation of reaction system and recycle of the polypyridyl platinum (II) complexes.Type: GrantFiled: December 3, 2008Date of Patent: May 10, 2011Assignee: Technical Institute of Physics and Chemistry of Chinese Academy of ScienceInventors: Li-Zhu Wu, Ming-Li Peng, Li Zhou, Deng-Hui Wang
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Patent number: 7932428Abstract: The invention relates to a process for preparing 1-butene from technical mixtures which comprise at least 1-butene, isobutene, n-butane and 2-butenes by partial conversion of the isobutene present, distillative removal of a fraction comprising 1-butene and isobutene, and conversion of the isobutene present therein to tert-butyl ethers.Type: GrantFiled: September 15, 2006Date of Patent: April 26, 2011Assignee: Evonik Oxeno GmbHInventors: Armin Rix, Udo Peters, Jochen Praefke, Dirk Röttger, Franz Nierlich
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Publication number: 20110021858Abstract: A process for the double-bond isomerization of olefins is disclosed. The process may include contacting a fluid stream comprising olefins with a fixed bed comprising an activated basic metal oxide isomerization catalyst to convert at least a portion of the olefin to its isomer. The isomerization catalysts disclosed herein may have a reduced cycle to cycle deactivation as compared to conventional catalysts, thus maintaining higher activity over the complete catalyst life cycle.Type: ApplicationFiled: July 21, 2009Publication date: January 27, 2011Applicant: LUMMUS TECHNOLOGY INC.Inventors: Bala Ramachandran, Sukwon Choi, Robert J. Gartside, Marvin I. Greene
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Patent number: 7655827Abstract: A process for selectively making 2-alkenes from a NAO using a mesoporous catalyst that has been surface modified with a Brönsted acid compound. The Brönsted acid compound has a reactive silane connector, an organic linking group, and a Brönsted acid group. The mesoporous catalyst has an average pore diameter in a range of about 12 to about 100 Angstroms and a surface area of between about 400 to about 1400 m2/gram.Type: GrantFiled: May 16, 2006Date of Patent: February 2, 2010Assignee: Chevron Phillips Chemical Company LPInventors: Ta Yen Ching, Jeffery Gee, Ruthann M Hickox
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Patent number: 7638673Abstract: This invention relates to a process for converting a hydrocarbon feedstock, comprising the steps of (A) feeding the feedstock to a reactor or adsorption unit; (B) contacting the feedstock in the reactor or adsorption unit with a solid particulate material useful for converting the feedstock under conversion conditions; (C) withdrawing converted feedstock from the reactor; and (D) removing, under the conversion conditions for a fractional time of step (B), at least a portion of the solid particulate material while the feedstock is being fed to the reactor or adsorption unit, wherein the portion is more than 0.1 wt. % of the solid particulate material in the reactor or adsorption unit and wherein the fractional time is less than 95% of the time of step (B).Type: GrantFiled: May 4, 2005Date of Patent: December 29, 2009Assignee: ExxonMobil Chemical Patents Inc.Inventors: Dana Lynn Pilliod, Katy Conley Randall, Eric Martin Harding
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Patent number: 7576251Abstract: A process is disclosed for the preferential conversion to 2-butene of a stream containing C4 compounds including 1-butene and 2-butene. The process involves mixing the C4 stream with a first hydrogen stream to form a feed stream, hydroisomerizing the feed stream in the presence of a first hydroisomerization catalyst in order to convert at least a portion of the 1-butene to 2-butene, thereby producing a hydroisomerization effluent, passing the hydroisomerization effluent through a fractionation column to form a top stream comprising isobutane and isobutylene and a bottoms stream comprising 2-butene, withdrawing a recycle stream from said fractionation column at a location above the feed point at which the weight ratio of 1-butene to 2-butene is high, and combining the recycle stream with at least one of the C4 stream and the feed stream upstream from the hydroisomerization catalyst. A corresponding apparatus also is disclosed.Type: GrantFiled: April 15, 2005Date of Patent: August 18, 2009Assignee: ABB Lummus Global Inc.Inventors: Robert J. Gartside, Thomas P. Skourlis, Hassan Kaleem
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Patent number: 7462277Abstract: In a continuous process for fractionating a C4 fraction (C4) by extractive distillation using a selective solvent (LM) in an extractive distillation column (EDK), it is proposed that a dividing wall (TW) is installed in the longitudinal direction in the extractive distillation column (EDK) to form a first region (A), a second region (B) and a lower combined column region (C) and a top stream (C4H10) comprising the butanes is taken off from the first region (A), a top stream (C4H8) comprising the butenes is taken off from the second region (B) and a stream (C4H6) comprising the hydrocarbons from the C4 fraction which are more soluble in the selective solvent (LM) than are the butanes and the butenes is taken off from the lower combined column region (C).Type: GrantFiled: July 22, 2003Date of Patent: December 9, 2008Assignee: BASF AktiengesellschaftInventors: Till Adrian, Thomas Hill, Klaus Kindler, Bernd Heida
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Patent number: 7429553Abstract: This invention relates to a method for reducing the toxicity of a mixture of hydrocarbons by means of fractional distillation, a distillate having a reduced toxicity and a composition including the distillate.Type: GrantFiled: May 15, 2007Date of Patent: September 30, 2008Assignee: Petroleum Oil and Gas Corporation of South Africa (Pty) Ltd.Inventors: Carl Dunlop, Stewart Hlohloza, Petrus Johannes Hoffmann, Cyril David Knottenbelt, Leon Walliser
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Patent number: 7405339Abstract: A process of contacting at least one isoparaffin and at least one C5 olefin in the presence of a catalyst composition under conversion conditions to provide for converting the at least one isoparaffin and the at least one C5 olefin is provided. The catalyst composition contains a heteropoly acid, zinc, and a support component.Type: GrantFiled: March 3, 2006Date of Patent: July 29, 2008Assignee: ConocoPhillips CompanyInventor: Bruce B. Randolph
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Patent number: 7390395Abstract: The present invention relates to new crystalline molecular sieve SSZ-56 prepared using a N,N-diethyl-2-methyldecahydroquinolinium cation as a structure directing agent, methods for synthesizing SSZ-56 and processes employing SSZ-56 in a catalyst.Type: GrantFiled: June 16, 2006Date of Patent: June 24, 2008Inventor: Saleh Elomari
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Patent number: 7355087Abstract: A catalytic distillation process for isomerizing and separating 1-alkenes from a mixed alkene stream. The process comprises contacting a mixed alkene stream comprising the 1-alkene and homologs thereof with a supported isomerization catalyst under isomerization/distillation conditions effective to convert at least a portion of the homologs to the 1-alkene, the isomerization/distillation conditions also being effective to produce a distillation overhead comprising a sufficient portion of the 1-alkene to drive isomerization of the homologs to the 1-alkene while maintaining the mixed alkene stream at least partially in liquid phase. The isomerization/distillation conditions are effective to recover a quantity of 1-alkene greater than an equilibrium quantity of 1-alkene recovered under isomerization conditions alone.Type: GrantFiled: October 1, 2004Date of Patent: April 8, 2008Assignee: Shell Oil CompanyInventors: Manuel Luis Cano, David Morris Hamilton, Jr., Terry Blane Thomason
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Patent number: 7332637Abstract: A method of modifying the activity of a solid acid catalyst by contact with a carboxylic acid is presented. The modified catalyst is exposed to a feed mixture including olefins in a reaction zone, and an effluent including an isomerized olefin product is withdrawn from the reaction zone. The isomerized olefin product includes a more random distribution of internal olefins than the olefins of the feed mixture. The feed mixture and the isomerized olefin product include linear olefins. The isomerization results in no more than about 10 weight percent additional branched, compared to the olefins of the feed mixture, among the olefins of the isomerized olefin product. The isomerized olefin product includes no more than about 20 weight percent dimer. The olefin monomers of the feed mixture and the isomerized olefin product include from about 4 to about 30 carbon atoms. The effluent includes no more than about 20 weight percent ester. The solid acid catalyst may be an acidic ion exchange resin.Type: GrantFiled: October 24, 2006Date of Patent: February 19, 2008Assignee: Chevron Phillips Chemical Company, LPInventors: Jeffery C. Gee, Willie J. Isom, Bruce E. Kreischer
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Patent number: 7329788Abstract: Process for producing gasoline components. The process comprises feeding a fresh olefinic hydrocarbon feedstock to a reaction zone, in which its structure is first isomerized. The isomerized hydrocarbon is drawn out of the first reaction zone and conducted to a second reaction zone, where the isomerized hydrocarbon is dimerized. The dimerized reaction product is drawn out of the second reaction zone and separated from the flow in a separation zone. Because there are more isoolefins present in the dimerization unit feed, more isoolefin dimers useful as fuel components can be produced.Type: GrantFiled: December 22, 2003Date of Patent: February 12, 2008Assignee: Neste Oil OyjInventors: Marja Tiitta, Elina Harlin, Antti Pyhälahti
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Patent number: 7326817Abstract: This invention relates to a method for reducing the toxicity of a mixture of hydrocarbons by means of fractional distillation, a distillate having a reduced toxicity and a composition including the distillate.Type: GrantFiled: October 27, 2004Date of Patent: February 5, 2008Assignee: Petroleum Oil and Gas Corporation of South Africa (Pty) Ltd.Inventors: Carl Dunlop, Stewart Hlohloza, Petrus Johannes Hoffmann, Cyril David Knottenbelt, Leon Walliser
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Patent number: 7271308Abstract: The present invention relates to embodiments for a process for the isomerization of at least one alpha olefin to an internal olefin via a multi-step process resulting in a mixture comprising alkene isomers and a low level of oligomers. According to the present invention an alkylaluminum compound is used in combination with the Group VIII transition metal salt for interaction with the latter, and thereby generating catalytically active species for the isomerization of 1-alkenes to internal alkenes, wherein this mixture is subsequently combined with an acid washed clay.Type: GrantFiled: October 19, 2004Date of Patent: September 18, 2007Assignee: Hercules IncorporatedInventor: Jian Jian Zhang
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Patent number: 7256152Abstract: A composition defined: either as comprising at least one Broensted acid, designated HB, dissolved in a liquid medium with an ionic nature of general formula Q+A?, in which Q+ represents an organic cation and A? represents an anion that is different from B, or as resulting from dissolving at least one Broensted acid, designated HB, in a non-aqueous liquid medium with an ionic nature of general formula Q+A?, in which Q+ represents an organic cation and A? represents an anion that is identical to the anion B, can be used as a catalyst and solvent in acid catalysis processes, in particular in the alkylation of aromatic hydrocarbons, the oligomerization of olefins, the dimerization of isobutene, the alkylation of olefins by isoparaffins, the isomerization of n-paraffins into isoparaffins, the isomerization of n-olefins into iso-olefins, the isomerization of the double bond of an olefin and the purification of an olefin mixture that contains branched alpha olefins as impurities.Type: GrantFiled: September 3, 2002Date of Patent: August 14, 2007Assignee: Institut Francais du PetroleInventors: Helene Olivier-Bourbigou, Dominique Commereuc, Olivia Martin, Lionel Magna, Emmanuel Pellier
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Publication number: 20070149839Abstract: The invention relates to a process for preparing 1-butene from technical mixtures which comprise at least 1-butene, isobutene, n-butane and 2-butenes by partial conversion of the isobutene present, distillative removal of a fraction comprising 1-butene and isobutene, and conversion of the isobutene present therein to tert-butyl ethers.Type: ApplicationFiled: September 15, 2006Publication date: June 28, 2007Applicant: Degussa AGInventors: Armin Rix, Udo Peters, Jochen Praefke, Dirk Roettger, Franz Nierlich
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Patent number: 7151199Abstract: Hydrocarbon or oxygenate conversion process in which a feedstock is contacted with a non zeolitic molecular sieve which has been treated to remove most, if not all, of the halogen contained in the catalyst. The halogen may be removed by one of several methods. One method includes heating the catalyst in a low moisture environment, followed by contacting the heated catalyst with air and/or steam. Another method includes steam-treating the catalyst at a temperature from 400° C. to 1000° C. The hydrocarbon or oxygenate conversion processes include the conversion of oxygenates to olefins, the conversion of oxygenates and ammonia to alkylamines, the conversion of oxygenates and aromatic compounds to alkylated aromatic compounds, cracking and dewaxing.Type: GrantFiled: June 10, 2002Date of Patent: December 19, 2006Assignee: ExxonMobil Chemical Patents Inc.Inventors: Luc Roger Marc Martens, Stephen N. Vaughn, Albert Edward Schweizer, John K. Pierce, Shun Chong Fung
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Patent number: 7132582Abstract: The present invention relates to a catalytic process for preparation of isolongifolene using nanocrystalline solid super acid. This process is an eco-friendly, single step, solvent free catalytic process for the preparation of a tricyclic sesqui-terpene hydrocarbon, isolongifolene. More particularly, the present invention provides a process for the catalytic isomerisation of longifolene to iso-longifolene using nano-crystalline sulfated zirconia as a solid super acid catalyst.Type: GrantFiled: May 30, 2003Date of Patent: November 7, 2006Assignee: Council of Scientific and Industrial ResearchInventors: Raksh Vir Jasra, Beena Tyagi, Manish Kumar Mishra
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Patent number: 7078579Abstract: A process for the double bond isomerization of a vinylidene olefin, comprising contacting a feed comprising the vinylidene olefin with an isomerization catalyst which comprises a molecular sieve in an acidic form, which molecular sieve comprises pores which have a pore size of more than 0.6 nm; and a process for treating an olefin mixture which comprises a linear ?-olefin and a vinylidene olefin which is isomeric to the linear ?-olefin and which is of the general formula CH2?C(R1)R2, wherein R1 represents an ethyl group and R2 represents a linear 1-alkyl group, which process comprises isomerizing the vinylidene olefin to form a double bond isomer of the vinylidene olefin by contacting a feed comprising the olefin mixture with an isomerization catalyst which comprises a molecular sieve in an acidic form, which molecular sieve comprises pores which have a pore size of more than 0.6 nm, and separating the linear ?-olefin from the double bond isomer of the vinylidene olefin.Type: GrantFiled: June 10, 2002Date of Patent: July 18, 2006Assignee: Shell Oil CompanyInventors: Michael Joseph Doll, Brendan Dermot Murray
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Patent number: 7041865Abstract: A process for the double bond isomerization of an olefin, which process comprises contacting a feed comprising the olefin with an isomerization catalyst, wherein prior to contacting the feed with the isomerization catalyst one or more components of the feed are pretreated by contacting with a pretreating material which comprises a zeolite which has a pore size of at least 0.Type: GrantFiled: June 10, 2002Date of Patent: May 9, 2006Assignee: Shell Oil CompanyInventors: Michael Joseph Doll, Brendan Dermot Murray
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Patent number: 6875901Abstract: An olefin isomerization process employs a basic metal oxide catalyst, such as magnesium oxide, which retains at least about 85 percent of its initial activity for at least about 168 hours of on-stream time. The catalyst is preferably a high purity magnesium oxide. The olefin isomerization process and catalyst described herein are advantageously used for the production of a terminal olefin such as 1-butene from an internal olefin such as 2-butene.Type: GrantFiled: May 23, 2001Date of Patent: April 5, 2005Assignee: ABB Lummus Global Inc.Inventors: Robert J. Gartside, Marvin I. Greene
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Patent number: 6872862Abstract: A method for making propylene from alpha olefins, internal linear olefins and isoolefins wherein the alpha olefins are subjected to a combination of hydrogenation and double bond isomerization to form additional internal linear olefins, the internal linear olefins are separated from the isoolefins and disproportionated with ethylene to form a propylene product, while the thus separated isoolefins are subjected to skeletal isomerization to form yet additional internal linear olefins to be converted into yet additional propylene product.Type: GrantFiled: June 25, 2003Date of Patent: March 29, 2005Assignee: Equistar Chemicals, LPInventors: Robert S. Bridges, Donald H. Powers, Steven T. Coleman