Using Catalyst Containing Mo, Re, Or W And Another Transition Metal Patents (Class 585/646)
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Patent number: 11780864Abstract: Non-d0 rhenium(V) alkylidyne catalysts useful for catalyzing alkyne metathesis reactions, such as homo- and cross-metathesis of alkynes or diynes, ring closing metathesis and ring-opening metathesis, methods or use, and preparation thereof. The catalysts are stable to air and moisture and tolerate a variety of functional groups in substrates.Type: GrantFiled: July 5, 2022Date of Patent: October 10, 2023Assignee: The Hong Kong University of Science and TechnologyInventors: Guochen Jia, Mingxu Cui
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Patent number: 10934231Abstract: Processes and multiple-stage catalyst systems are disclosed for producing propene by at least partially isomerizing butene in an isomerization reaction zone having an isomerization catalyst to form an isomerization reaction product, at least partially metathesizing the isomerization reaction product in a metathesis reaction zone having a metathesis catalyst to form a metathesis reaction product, and at least partially cracking the metathesis reaction product in a cracking reaction zone having a cracking catalyst. The isomerization catalyst may be MgO, and the metathesis catalyst may be a mesoporous silica catalyst support impregnated with a metal oxide. The metathesis reaction zone may be downstream of the isomerization reaction zone, and the cracking reaction zone may be downstream of the metathesis reaction zone.Type: GrantFiled: January 10, 2018Date of Patent: March 2, 2021Assignee: Saudi Arabian Oil CompanyInventors: Faisal H. Alshafei, Munir D. Khokhar, Sohel K. Shaikh
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Patent number: 10906026Abstract: Provided here are catalyst compositions containing tungsten oxide on silica supports and prepared by spray drying a mixture containing a tungsten precursor, silica support, and a surfactant. Also provided here are methods of using the catalytic compositions, prepared by spray drying, in an olefin metathesis process to produce propylene from butenes.Type: GrantFiled: October 24, 2018Date of Patent: February 2, 2021Inventors: Faisal H. Alshafei, Munir D. Khokhar, Sohel K. Shaikh, Mohammed R. Alalouni, Gopal Juttu
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Patent number: 10758892Abstract: The invention relates to a process for the metathesis of olefins implemented with a catalyst comprising a mesoporous matrix and at least the elements molybdenum and silicon, said elements being incorporated into said matrix by means of at least two precursors of which at least one precursor contains molybdenum and at least one precursor contains silicon.Type: GrantFiled: July 26, 2016Date of Patent: September 1, 2020Assignee: IFP Engines NouvellesInventors: Audrey Bonduelle, Alexandra Chaumonnot, Damien Delcroix, Christophe Vallee, Souad Rafik-Clement, Severine Forget
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Patent number: 10737254Abstract: The invention relates to a process for the metathesis of olefins implemented with a catalyst comprising a mesoporous matrix and at least the elements molybdenum and silicon, said elements being incorporated into said matrix by means of at least one precursor comprising molybdenum and silicon and having at least one sequence of Si—O—Mo bonds.Type: GrantFiled: July 26, 2016Date of Patent: August 11, 2020Assignee: IFP Energies NouvellesInventors: Audrey Bonduelle, Alexandra Chaumonnot, Damien Delcroix, Christophe Vallee, Souad Rafik-Clement, Severine Forget
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Patent number: 10619112Abstract: Process scheme configurations are disclosed that enable conversion of crude oil feeds with several processing units in an integrated manner into petrochemicals. The designs utilize minimum capital expenditures to prepare suitable feedstocks for the steam cracker complex. The integrated process for converting crude oil to petrochemical products including olefins and aromatics, and fuel products, includes mixed feed steam cracking and gas oil steam cracking. Feeds to the mixed feed steam cracker include light products and naphtha from hydroprocessing zones within the battery limits, recycle streams from the C3 and C4 olefins recovery steps, and raffinate from a pyrolysis gasoline aromatics extraction zone within the battery limits. Feeds to the gas oil steam cracker include hydrotreated gas oil range intermediates from vacuum gas oil hydrotreating.Type: GrantFiled: November 17, 2017Date of Patent: April 14, 2020Assignee: Saudi Arabian Oil CompanyInventor: Mohammed Saeed Al-Ghamdi
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Patent number: 10532347Abstract: Embodiments of processes for producing propylene utilize a dual catalyst system comprising a mesoporous silica catalyst impregnated with metal oxide and a mordenite framework inverted (MFI) structured silica catalyst downstream of the mesoporous silica catalyst, where the mesoporous silica catalyst includes a pore size distribution of at least 2.5 nm to 40 nm and a total pore volume of at least 0.600 cm3/g, and the MFI structured silica catalyst has a total acidity of 0.001 mmol/g to 0.1 mmol/g. The propylene is produced from the butene stream via metathesis by contacting the mesoporous silica catalyst and subsequent cracking by contacting the MFI structured silica catalyst.Type: GrantFiled: January 2, 2018Date of Patent: January 14, 2020Assignees: Saudi Arabian Oil Company, King Fahd University of Petroleum & MineralsInventors: Sulaiman Saleh Al-Khattaf, Arudra Palani, Tazul Islam Bhuiyan, Sohel Shaikh, Mohammad Naseem Akhtar, Abdullah M. Aitani, Mohammed A. Al-Yami
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Patent number: 10328417Abstract: Provided is mixed catalysts for an olefin metathesis reaction having a high selectivity so that side reactions do not take place and having a high activity, which side reactions are polymerization reactions, isomerization from 2-butene to 1-butene, and reactions of 1-butene with other molecules. Mixed catalysts for an olefin metathesis reaction can be provided, the mixed catalyst comprising a metathesis catalyst which is tungsten oxide supported on a silica carrier and a co-catalyst that is composited from at least three oxides of Groups 1 and 2 metallic elements. By using the catalyst an olefin metathesis reaction of generating propylene from ethylene and 2-butene, the solid basicity to promote the metathesis reaction can be increase, and influences of gas containing isomers of 2-butene contained in raw material gas can be inhibited to increase the production efficiency of propylene even at low temperatures.Type: GrantFiled: October 6, 2012Date of Patent: June 25, 2019Assignee: Clariant Catalysts (Japan) K.K.Inventors: Yuzuru Sakamoto, Moriyasu Sugeta
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Patent number: 10322984Abstract: The invention relates to a process for the metathesis of olefins implemented with a catalyst comprising a mesoporous matrix and at least the elements molybdenum and aluminum, said elements being incorporated into said matrix by means of at least two precursors of which at least one precursor contains molybdenum and at least one precursor contains aluminum.Type: GrantFiled: July 26, 2016Date of Patent: June 18, 2019Assignee: IFP Energies nouvellesInventors: Audrey Bonduelle, Alexandra Chaumonnot, Damien Delcroix, Christophe Vallee
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Patent number: 10029960Abstract: The present disclosure relates to chemical catalysts and methods that may be used for the production and/or interconversion of olefins. In some embodiments, methods for producing propylene from ethylene and butene comprising, (a) obtaining a catalyst composition comprising an isomerization catalyst and a disproportionation catalyst, wherein the weight ratio of the isomerization catalyst to the disproportionation catalyst is from 10:1 to 1:10; and (b) reacting butene with ethylene at a temperature from about 500° F. (260° C.) to about 650° F. (350° C.) in the presence of the catalyst composition under conditions sufficient to produce propylene are provided.Type: GrantFiled: January 24, 2017Date of Patent: July 24, 2018Assignee: Lyondell Chemical Technology, L.P.Inventors: Lei Zhang, Daniel F. White
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Patent number: 9598331Abstract: Processes for the production of high purity alpha olefins from a mixture of olefins are disclosed. The processes may include: contacting propylene and a hydrocarbon mixture comprising a mixture of olefins having a carbon number n with a first metathesis catalyst to form a metathesis product comprising a beta-olefin having a carbon number n+1, an alpha-olefin having a carbon number n?1, as well as any unreacted propylene and olefins having a carbon number n. The metathesis product may be fractionated to recover a fraction comprising the beta-olefin having a carbon number n+1. Ethylene and the fraction comprising the beta-olefin having a carbon number n+1 may then be contacted with a second metathesis catalyst to form a second metathesis product comprising an alpha-olefin having a carbon number n and propylene, which may be fractionated to form a propylene fraction and a fraction comprising the alpha olefin having a carbon number n.Type: GrantFiled: November 20, 2014Date of Patent: March 21, 2017Assignee: Lummus Technology Inc.Inventors: Bala Ramachandran, Sukwon Choi
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Patent number: 8993470Abstract: Organometallic compounds of the general formula (I), in which M=Mo, W, are claimed.Type: GrantFiled: March 31, 2011Date of Patent: March 31, 2015Assignee: Studiengesellschaft Kohle mbHInventors: Alois Fuerstner, Johannes Heppekausen, Volker Hickmann, Robert Stade
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Patent number: 8993823Abstract: A process for the metathesis of olefins has been developed. The process comprises contacting a hydrocarbon feedstock with a catalyst at metathesis conditions. The catalyst comprises a tungsten compound, which contains at least one tungsten-fluoro bond, dispersed or grafted onto a support. A specific example of the catalyst is the compound WOF(CH2CMe3)3 grafted onto a silica support. The feedstock comprises a first and a second olefin wherein the second olefin has a carbon number of at least two greater than the first olefin and the product is an olefin with a carbon number intermediate between the first and second olefin. Specifically the process produces propylene from ethylene and butylene.Type: GrantFiled: June 25, 2014Date of Patent: March 31, 2015Assignee: UOP LLCInventors: Mostafa Taoufik, Etienne Mazoyer, Christopher P. Nicholas, Jean-Marie Basset
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Publication number: 20150065723Abstract: The present invention provides methods for the synthesis of catalysts and precursors thereof. Methods of the invention may comprise combining a catalyst precursor and at least one ligand to generate a catalytically active species, often under mild conditions and in high yields. In some cases, a wide variety of catalysts may be synthesized from a single catalyst precursor. Methods of the invention may also include the preparation of catalysts which, under reaction conditions known in the art, may have been difficult or impossible to prepare and/or isolate due to, for example, steric crowding at the metal center. The present invention also provides catalyst compositions, and precursors thereof, which may be useful in various chemical reactions including olefin metathesis. In some cases, methods of the invention may reduce the number of synthetic and purification steps required to produce catalysts and/or other reaction products, as well as reducing time, cost, and waste production.Type: ApplicationFiled: September 8, 2014Publication date: March 5, 2015Inventors: Adam S. Hock, Richard R. Schrock
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Patent number: 8895795Abstract: Acid washing of silica supports, used for supported tungsten catalysts, improves the activity of the resulting catalyst (i.e., its conversion level at a given temperature) for the metathesis of olefins, without compromising its selectivity to the desired conversion product(s). Exemplary catalysts and processes include those for the production of valuable light olefins such as propylene from a hydrocarbon feedstock comprising ethylene and butylene.Type: GrantFiled: February 5, 2010Date of Patent: November 25, 2014Assignee: UOP LLCInventors: Mark A. Krawczyk, Kristoffer E. Popp, Christopher P. Nicholas, Jennifer F. Abrahamian
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Publication number: 20140309466Abstract: The invention relates to a method of forming an olefin from a first olefin and a second olefin in a metathesis reaction, comprising step (i): (i) reacting the first olefin with the second olefin in the presence of a compound that catalyzes said metathesis reaction such that the molar ratio of said compound to the first or the second olefin is from 1:500 or less, and the conversion of the first or the second olefin to said olefin is at least 50%, characterized in that as compound that catalyzes said metathesis reaction a compound of the following formula is used: wherein M is Mo or W; R1 is aryl, heteroaryl, alkyl, or heteroalkyl; optionally substituted; R2 and R3 can be the same or different and are hydrogen, alkyl, alkenyl, heteroalkyl, heteroalkenyl, aryl, or heteroaryl; optionally substituted; R5 is alkyl, alkoxy, heteroalkyl, aryl, heteroaryl, silylalkyl, silyloxy, optionally substituted; and R4 is a residue R6—X—, wherein X?O and R6 is aryl, optionally substituted; or X?S and R6 is aryl, optType: ApplicationFiled: March 13, 2014Publication date: October 16, 2014Inventors: Levente Ondi, Jeno Varga, Agota Bucsai, Florian Toth, Krisztian Lorincz, Csaba Hegedus, Emmanuel Robbe, Georg Emil Frater
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Publication number: 20140235914Abstract: Provided are catalyst composites useful for the production of olefins during a metathesis reaction, as well as methods of making and using the same. Certain methods comprise a support comprising at least about 90% by weight silica; and an eggshell layer on the support comprising about 0.25 to about 10 wt. % tungsten in the form of tungsten oxide or tungsten oxide hydrate, based on the total weight of the catalyst composite.Type: ApplicationFiled: February 19, 2013Publication date: August 21, 2014Applicant: BASF CorporationInventor: Joseph C. Dellamorte
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Patent number: 8722950Abstract: The invention is for a process for producing propylene and hexene (along with ethylene, pentenes, product butenes, heptenes and octenes) by metathesis from butenes (iso-, 1- and cis and trans 2-) and pentenes and then aromatizing the hexenes (along with higher olefins, such as heptenes and octenes) to benzene (along with toluene, xylenes, ethylbenzene and styrene). Since the desired products of the metathesis reaction are propylene and hexene, the feed to the metathesis reaction has a molar ratio for 1-butene:2-butene which favors production of propylene and 3-hexene with the concentration of hexenes and higher olefins in the metathesis product being up to 30 mole %. An isomerization reactor may be used to obtain the desired molar ratio of 1-butene:2-butene for the feed composition into the metathesis reactor. After the metathesis reaction, of hexene and higher olefins are separated for aromatization to benzene and other aromatics.Type: GrantFiled: April 26, 2010Date of Patent: May 13, 2014Assignee: Saudi Basic Industries CorporationInventors: Jaap W. van Hal, Scott A. Stevenson, Jim Allman, David L. Sullivan, Travis Conant
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Patent number: 8704028Abstract: Processes for the conversion, under conditions and with a catalyst system effective for olefin metathesis, of hydrocarbon feedstocks comprising an acyclic symmetrical olefin (e.g., butene-2) are described. Olefin products of lower and higher carbon numbers (e.g., propylene and pentene) are formed in the presence of a catalyst comprising a solid support and a tungsten hydride bonded to alumina present in the support. This occurs despite the olefin metathesis reaction mechanism leading to a degenerative result, without any expected production of different carbon number products from acyclic symmetrical olefins.Type: GrantFiled: March 30, 2010Date of Patent: April 22, 2014Assignee: UOP LLCInventors: Christopher P. Nicholas, Etienne Mazoyer, Mostafa Taoufik, Jean-Marie Basset, Paul T. Barger
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Patent number: 8704029Abstract: Processes for the conversion, under conditions and with a catalyst system effective for olefin metathesis, of hydrocarbon feedstocks comprising butylene, for example all or a large proportion of a single C4 olefin isomer such as butene-1, are described. Olefin products, and particularly propylene, are formed in the presence of a catalyst comprising a solid support and a tungsten hydride bonded to alumina present in the support. This occurs despite the expectation that the olefin metathesis reaction mechanism leads to the formation of olefin products having other carbon numbers.Type: GrantFiled: March 30, 2010Date of Patent: April 22, 2014Assignee: UOP LLCInventors: Christopher P. Nicholas, Etienne Mazoyer, Mostafa Taoufik, Jean-Marie Basset, Paul T. Barger, James E. Rekoske
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Patent number: 8674155Abstract: Systems and methods for processing one or more hydrocarbons are provided. In one or more embodiments, the method can include thermally converting a hydrocarbon comprising methane to produce a first product comprising acetylene. The method can also include hydrogenating the first product to produce a second product comprising ethylene. The method can further include catalytically reacting the second product with one or more butene products to produce a third product comprising propylene.Type: GrantFiled: December 22, 2010Date of Patent: March 18, 2014Assignee: Kellogg Brown & Root, LLCInventor: Curtis N. Eng
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Publication number: 20140046110Abstract: The present invention relates to a process for isomerizing linear alpha-olefins having from 4 to 8 carbon atoms over a heterogeneous catalyst, wherein the catalyst comprises a hydrogenation metal and a selectivity promoter selected from among selenium and tellurium on a support, and also a process for preparing 1-olefins by a metathesis reaction of 2-olefins with ethene, wherein the 2-olefins are prepared by the above mentioned isomerization process.Type: ApplicationFiled: April 27, 2012Publication date: February 13, 2014Applicant: BASF SEInventors: Stefan Iselborn, Michael Hesse, Piotr Makarczyk
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Patent number: 8598400Abstract: The present invention generally relates to methods for performing metathesis reactions, including cross-metathesis reactions. Methods described herein exhibit enhanced activity and stereoselectivity, relative to known methods, and are useful in the synthesis of a large assortment of biologically and therapeutically significant agents.Type: GrantFiled: February 8, 2011Date of Patent: December 3, 2013Assignees: Massachusetts Institute of Technology, Trustees of Boston CollegeInventors: Amir H. Hoveyda, Simon J. Meek, Robert V. O'Brien, Josep Llaveria Cros, Richard R. Schrock
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Patent number: 8552242Abstract: The present invention generally relates to methods for performing metathesis reactions, including cross-metathesis reactions. Methods described herein exhibit enhanced activity and stereoselectivity, relative to known methods, and are useful in the synthesis of a large assortment of biologically and therapeutically significant agents.Type: GrantFiled: February 8, 2011Date of Patent: October 8, 2013Assignees: Massachusetts Institute of Technology, Trustees of Boston CollegeInventors: Amir H. Hoveyda, Simon J. Meek, Robert V. O'Brien, Josep Llaveria Cros, Richard R. Schrock
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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: 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: 8389784Abstract: Ethanol obtained from ordinary biomass resources contains many impurities other than water and these impurities themselves or their decomposition products contaminate ethylene when the ethylene is produced by a dehydration reaction, whereby the activity of metathesis catalyst is adversely affected. A method for producing propylene of the present invention is characterized in that the ethanol obtained from biomass is converted to ethylene by a dehydration reaction, the ethylene is separated from the generated water, the separated ethylene is purified by adsorption in an adsorption tower filled with an adsorbent, and then a metathesis reaction is carried out along with a raw material containing n-butene. With the present invention, propylene having biomass-derived carbon and reduced-environmental burden can be efficiently produced without lowering the catalysis activity.Type: GrantFiled: November 13, 2006Date of Patent: March 5, 2013Assignee: Mitsui Chemicals, Inc.Inventors: Toshihiro Takai, Daisuke Mochizuki, Michiaki Umeno
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Patent number: 8389788Abstract: Processes for olefin metathesis, for example for the production of propylene, utilize a catalyst comprising a solid support and a tungsten hydride bonded to alumina present in the support. Conversion, selectivity, and/or catalyst stability advantages may be realized when a first olefin reactant (e.g., ethylene) is present in the hydrocarbon feedstock at a stoichiometric deficit relative to a second, higher carbon number olefin reactant (e.g., butylene).Type: GrantFiled: March 30, 2010Date of Patent: March 5, 2013Assignee: UOP LLCInventors: Mostafa Taoufik, Etienne Mazoyer, Christopher P. Nicholas, Jean-Marie Basset
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Patent number: 8362311Abstract: The present invention relates generally to catalysts and processes for the Z-selective formation of internal olefin(s) from terminal olefin(s) via homo-metathesis reactions.Type: GrantFiled: September 30, 2009Date of Patent: January 29, 2013Assignees: Massachusetts Institute of Technology, Trustees of Boston CollegeInventors: Richard R. Schrock, Annie J. King, Yu Zhao, Margaret M. Flook, Amir H. Hoveyda
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Publication number: 20120316374Abstract: A process for the metathesis of olefins has been developed. The process comprises contacting a hydrocarbon feedstock with a catalyst at metathesis conditions. The catalyst comprises a tungsten compound, which contains at least one tungsten-fluoro bond, dispersed or grafted onto a support. A specific example of the catalyst is the compound WOF(CH2CMe3)3 grafted onto a silica support. The feedstock comprises a first and a second olefin wherein the second olefin has a carbon number of at least two greater than the first olefin and the product is an olefin with a carbon number intermediate between the first and second olefin. Specifically the process produces propylene from ethylene and butylene.Type: ApplicationFiled: June 9, 2011Publication date: December 13, 2012Applicant: UOP LLCInventors: Mostafa Taoufik, Etienne Mazoyer, Christopher P. Nicholas, Jean-Marie Basset
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Patent number: 8324440Abstract: Silica supports having a surface area from about 250 m2/g to about 600 m2/g and an average pore diameter from about 45 ? to about 170 ?, used for supported tungsten catalysts, improves the activity of the resulting catalyst (i.e., its conversion level at a given temperature) for the metathesis of olefins, without compromising its selectivity to the desired conversion product(s). Exemplary catalysts and processes include those for the production of valuable light olefins such as propylene from a hydrocarbon feedstock comprising ethylene and butylene.Type: GrantFiled: February 5, 2010Date of Patent: December 4, 2012Assignee: UOP LLCInventors: Kristoffer E. Popp, Mark A. Krawczyk, Christopher P. Nicholas, Jennifer F. Abrahamian
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Publication number: 20120264990Abstract: A process for olefin metathesis is disclosed. The process involves contacting a feedstock comprising a first olefin and a second olefin having a carbon number at least two greater than that of the first olefin with a catalyst comprising a tungsten component on a refractory oxide support, e.g. silica at metathesis conditions to provide a product olefin having an intermediate carbon number between that of the first and second olefin. The catalyst is characterized in that it is first pretreated with hydrogen followed by treatment with ethylene.Type: ApplicationFiled: April 14, 2011Publication date: October 18, 2012Applicant: UOP LLCInventors: Christopher P Nicholas, Mark A. Krawczyk, Kristoffer E. Popp, Jennifer F. Abrahamian
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Patent number: 8119852Abstract: The present invention relates to a process for manufacturing neohexene, comprising contacting isobutene with a supported catalyst comprising a tungsten compound chosen from tungsten hydrides, organometallic tungsten compounds and organometallic tungsten hydrides, and a support comprising an oxide of aluminum, so as to form a reaction mixture comprising neohexene, and preferably separating neohexene from the reaction mixture, so as to isolate it. The contacting leads to the direct production of neohexene, in particular in a single (reaction) stage and with a high molar selectivity for neohexene. The contacting can be performed at a temperature of 50 to 600 ° C., under a total absolute pressure of 0.01 to 100 MPa.Type: GrantFiled: December 11, 2007Date of Patent: February 21, 2012Assignee: BP Oil International LimitedInventors: Jean Marie Basset, Francois Stoffelbach, Mostafa Taoufik, Jean Thivolle-Cazat
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Patent number: 8013200Abstract: In a process for producing olefins by a metathesis reaction comprising feeding an olefin gas to pass the olefin through a catalyst bed in the presence of hydrogen gas to convert the olefin into another kind of olefin, the catalyst bed having a catalyst including at least one metal selected from the group consisting of tungsten, molybdenum, rhenium, niobium, tantalum and vanadium, and a co-catalyst including a basic compound having at least one metal selected from the group consisting of Group Ia (alkali metals), Group IIa (alkaline earth metals), Group IIb and Group IIIa of the periodic table, the improvement lies in controlling the superficial velocity of the gas passing through the catalyst bed to 0.01 to 2.0 m/sec. According to the present invention, the presence of hydrogen gas dramatically increases the durability of the metathesis catalytic activity and the by-production of paraffins is suppressed.Type: GrantFiled: April 18, 2008Date of Patent: September 6, 2011Assignee: Mitsui Chemicals, Inc.Inventors: Toshihiro Takai, Hirokazu Ikenaga, Makoto Kotani, Shigeaki Fujii
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Publication number: 20110196185Abstract: Acid washing of silica supports, used for supported tungsten catalysts, improves the activity of the resulting catalyst (i.e., its conversion level at a given temperature) for the metathesis of olefins, without compromising its selectivity to the desired conversion product(s). Exemplary catalysts and processes include those for the production of valuable light olefins such as propylene from a hydrocarbon feedstock comprising ethylene and butylene.Type: ApplicationFiled: February 5, 2010Publication date: August 11, 2011Applicant: UOP LLCInventors: Mark A. KRAWCZYK, Kristoffer E. POPP, Christopher P. NICHOLAS, Jennifer F. ABRAHAMIAN
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Publication number: 20110196184Abstract: Silica supports having a surface area from about 250 m2/g to about 600 m2/g and an average pore diameter from about 45 ? to about 170 ?, used for supported tungsten catalysts, improves the activity of the resulting catalyst (i.e., its conversion level at a given temperature) for the metathesis of olefins, without compromising its selectivity to the desired conversion product(s). Exemplary catalysts and processes include those for the production of valuable light olefins such as propylene from a hydrocarbon feedstock comprising ethylene and butylene.Type: ApplicationFiled: February 5, 2010Publication date: August 11, 2011Applicant: UOP LLCInventors: Kristoffer E. POPP, Mark A. KRAWCZYK, Christopher P. NICHOLAS, Jennifer F. ABRAHAMIAN
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Patent number: 7977522Abstract: A process of producing olefins by a metathesis reaction in a practical low temperature range by improving the reactivity of the catalyst is provided. The process of producing olefins according to the present invention allows a metathesis reaction of olefins, which uses a catalyst containing metal elements such as tungsten, molybdenum, rhenium or the like, to proceed at an industrially sufficient reaction rate in a practical low temperature range, by using a compound containing at least one metal element selected from the metals of Group Ia (alkali metals), Group IIa (alkaline earth metals), Group IIb and Group IIIa as co-catalyst and allowing hydrogen gas to co-exist with the reaction raw material.Type: GrantFiled: February 24, 2006Date of Patent: July 12, 2011Assignee: Mitsui Chemicals, Inc.Inventors: Toshihiro Takai, Takeshi Kubota
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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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Publication number: 20110098496Abstract: Novel group 6 organometallic compounds are obtained by reaction of at least one boron compound comprising at least one hydroxy, sulfhydryl or amino function with at least one compound of a group 6 transition metal. These compounds are used in a catalytic composition utilized in an olefin metathesis method.Type: ApplicationFiled: October 26, 2010Publication date: April 28, 2011Applicant: IFP ENERGIES NOUVELLESInventors: Ludovic Chahen, Mikael Berthod, Helene Olivier-Bourbigou
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Patent number: 7923588Abstract: A C4-olefin mixture having a 1,3-butadiene content of from 100 to 500 ppm and a content of 1,2-dienes of less than 10 ppm is described. The present invention further provides a process for preparing this C4-olefin mixture and provides for its use in a metathesis reaction for preparing 2-pentene and/or 3-hexene.Type: GrantFiled: October 13, 2005Date of Patent: April 12, 2011Assignee: BASF SEInventors: Jürgen Stephan, Andreas Brodhagen, Markus Schubert, Frank Poplow, Michael Röper, Thomas Hill
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Patent number: 7905288Abstract: A method for chemically-upgrading shale-bound kerogen comprises contacting shale-bound kerogen comprising carbon-carbon double bonds with a quantity of alkene species in the presence of an olefin metathesis catalyst. A catalyzed metathetical reaction occurs between the shale-bound kerogen and the alkene species and smaller kerogen-derived molecular species are formed. The smaller kerogen-derived molecular species are recovered.Type: GrantFiled: November 25, 2008Date of Patent: March 15, 2011Assignee: Los Alamos National Security, LLCInventor: Scott A. Kinkead
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Patent number: 7868216Abstract: A process for producing high purity propylene comprises: a step for dimerizing ethylene to 1-butene; a step for hydroisomerizing 1-butene to 2-butenes; and a step for metathesis of 2-butenes by ethylene. Advantageously, the ethylene used to produce the 1-butene and ethylene for metathesis derive from a steam cracking unit. To increase propylene production, the process can use a steam cracking or FCC C4cut as an additional butene source.Type: GrantFiled: December 23, 2005Date of Patent: January 11, 2011Assignee: IFP Energies NouvellesInventors: Jean-Alain Chodorge, Christian Dupraz
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Publication number: 20100145126Abstract: A process of producing olefins by a metathesis reaction in a practical low temperature range by improving the reactivity of the catalyst is provided. The process of producing olefins according to the present invention allows a metathesis reaction of olefins, which uses a catalyst containing metal elements such as tungsten, molybdenum, rhenium or the like, to proceed at an industrially sufficient reaction rate in a practical low temperature range, by using a compound containing at least one metal element selected from the metals of Group Ia (alkali metals), Group IIa (alkaline earth metals), Group IIb and Group IIIa as co-catalyst and allowing hydrogen gas to co-exist with the reaction raw material.Type: ApplicationFiled: February 24, 2006Publication date: June 10, 2010Applicant: MITSUI CHEMICALS, INC.Inventors: Toshihiro Takai, Takeshi Kubota
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Patent number: 7696398Abstract: A process of stabilizing an olefin metathesis product mixture, preferably, against double bond isomerization and thermal and chemical degradation. The process involves (a) contacting an olefin metathesis product mixture comprising one or more olefins produced in a metathesis process, a metathesis catalyst comprising a catalytic metal and one or more ligands, optionally, one or more metathesis catalyst degradation products, and optionally, one or more metals derived from sources other than the catalyst or catalyst degradation product(s), with an adsorbent, more preferably carbon; or alternatively, (b) subjecting the olefin metathesis product mixture to a two-step distillation, preferably, including short path wiped-film evaporation. A stabilized olefin metathesis product mixture to a two-step distillation, preferably, including short path wiped-film evaporation.Type: GrantFiled: September 26, 2003Date of Patent: April 13, 2010Assignee: Dow GlobalTTechnologies, Inc.Inventors: Kenneth A. Burdett, Rob R. Maughon, Patrick H. Au-Yeung
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Patent number: 7683180Abstract: The invention pertains to the use of Group 8 transition metal carbene complexes as catalysts for olefin cross-metathesis reactions, and for enantioselective reactions in particular. The synthesis of these complexes and details of their use as catalysts is also provided.Type: GrantFiled: April 16, 2002Date of Patent: March 23, 2010Assignee: California Institute of TechnologyInventors: Robert H. Grubbs, Donald W. Ward, Thomas J. Seiders, Steven D. Goldberg
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Publication number: 20100063339Abstract: In a process for producing olefins by a metathesis reaction comprising feeding an olefin gas to pass the olefin through a catalyst bed in the presence of hydrogen gas to convert the olefin into another kind of olefin, the catalyst bed having a catalyst including at least one metal selected from the group consisting of tungsten, molybdenum, rhenium, niobium, tantalum and vanadium, and a co-catalyst including a basic compound having at least one metal selected from the group consisting of Group Ia (alkali metals), Group IIa (alkaline earth metals), Group IIb and Group IIIa of the periodic table, the improvement lies in controlling the superficial velocity of the gas passing through the catalyst bed to 0.01 to 2.0 m/sec. According to the present invention, the presence of hydrogen gas dramatically increases the durability of the metathesis catalytic activity and the by-production of paraffins is suppressed.Type: ApplicationFiled: April 18, 2008Publication date: March 11, 2010Applicant: MITSUI CHEMICALS, INC.Inventors: Toshihiro Takai, Hirokazu Ikenaga, Makoto Kotani, Shigeaki Fujii
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Publication number: 20100056839Abstract: 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: ApplicationFiled: September 4, 2009Publication date: March 4, 2010Applicants: LUMMUS TECHNOLOGY INC., BASF CATALYSTS LLCInventors: Bala Ramachandran, Sukwon Choi, Robert J. Gartside, Shane Kleindienst, Wolfgang Ruettinger, Saeed Alerasool
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Publication number: 20100030003Abstract: The present invention relates to a process for manufacturing neohexene, comprising contacting isobutene with a supported catalyst comprising a tungsten compound chosen from tungsten hydrides, organometallic tungsten compounds and organometallic tungsten hydrides, and a support comprising an oxide of aluminium, so as to form a reaction mixture comprising neohexene, and preferably separating neohexene from the reaction mixture, so as to isolate it. The contacting leads to the direct production of neohexene, in particular in a single (reaction) stage and with a high molar selectivity for neohexene. The contacting can be performed at a temperature of 50 to 600° C., under a total absolute pressure of 0.01 to 100 MPa.Type: ApplicationFiled: December 11, 2007Publication date: February 4, 2010Applicant: BP OIL INTERNATIONAL LIMITEDInventors: Jean-Marie Basset, Francois Stoffelbach, Mostafa Taoufik, Jean Thivolle-Cazat
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Patent number: 7638672Abstract: The invention relates to a method for converting ethylene into propylene consisting in reacting said ethylene with a supported metal compound comprising an aluminium oxide based support to which a tungsten hydride is grafted. Said reaction is carried out at a temperature ranging from 20 to 600° C., preferably between 50 and 350° C., at an absolute pressure ranging from 0.01 to 8 MPa, preferably between 0.01 and 1 MPa. A catalyst is regeneratable by introducing hydrogen at a temperature of 50-300° C.Type: GrantFiled: June 27, 2005Date of Patent: December 29, 2009Assignee: CPE Lyon Formation Continue et et Recherche CPE Lyon FCRInventors: Christophe Coperet, Jean-Marie Basset, Jean Thivolle-Cazat, Erwan Le Roux, Mostafa Taoufik
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Patent number: 7635794Abstract: The invention relates to a method for metathesis of one or several reagents comprising a linear or branched hydrocarbon chain containing a double olefinic bond Csp2?Csp2 consisting in reacting said reagent or reagents with a supported metal compound comprising an aluminum oxide-based support to which a tungsten hydride is grafted. Typically, each said reagent or reagents comprises from 2 to 30 carbon atoms. The reagent can be embodied in the form of olefin. The inventive method can be used, for example for producing propylene from ethylene and butane.Type: GrantFiled: July 1, 2005Date of Patent: December 22, 2009Assignee: CPE Lyon Formation Continue ET Recherche-CPE Lyon FCRInventors: Jean-Marie Basset, Jean Thivolle-Cazat, Mostafa Taoufik, Erwan Le Roux, Christophe Coperet