Using Catalyst Containing Mo, Re, Or W And Another Transition Metal Patents (Class 585/646)
  • Patent number: 10328417
    Abstract: 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: Grant
    Filed: October 6, 2012
    Date of Patent: June 25, 2019
    Assignee: Clariant Catalysts (Japan) K.K.
    Inventors: Yuzuru Sakamoto, Moriyasu Sugeta
  • Patent number: 10322984
    Abstract: 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: Grant
    Filed: July 26, 2016
    Date of Patent: June 18, 2019
    Assignee: IFP Energies nouvelles
    Inventors: Audrey Bonduelle, Alexandra Chaumonnot, Damien Delcroix, Christophe Vallee
  • Patent number: 10029960
    Abstract: 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: Grant
    Filed: January 24, 2017
    Date of Patent: July 24, 2018
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Lei Zhang, Daniel F. White
  • Patent number: 9598331
    Abstract: 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: Grant
    Filed: November 20, 2014
    Date of Patent: March 21, 2017
    Assignee: Lummus Technology Inc.
    Inventors: Bala Ramachandran, Sukwon Choi
  • Patent number: 8993823
    Abstract: 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: Grant
    Filed: June 25, 2014
    Date of Patent: March 31, 2015
    Assignee: UOP LLC
    Inventors: Mostafa Taoufik, Etienne Mazoyer, Christopher P. Nicholas, Jean-Marie Basset
  • Patent number: 8993470
    Abstract: Organometallic compounds of the general formula (I), in which M=Mo, W, are claimed.
    Type: Grant
    Filed: March 31, 2011
    Date of Patent: March 31, 2015
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Alois Fuerstner, Johannes Heppekausen, Volker Hickmann, Robert Stade
  • Publication number: 20150065723
    Abstract: 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: Application
    Filed: September 8, 2014
    Publication date: March 5, 2015
    Inventors: Adam S. Hock, Richard R. Schrock
  • Patent number: 8895795
    Abstract: 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: Grant
    Filed: February 5, 2010
    Date of Patent: November 25, 2014
    Assignee: UOP LLC
    Inventors: Mark A. Krawczyk, Kristoffer E. Popp, Christopher P. Nicholas, Jennifer F. Abrahamian
  • Publication number: 20140309466
    Abstract: 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, opt
    Type: Application
    Filed: March 13, 2014
    Publication date: October 16, 2014
    Inventors: Levente Ondi, Jeno Varga, Agota Bucsai, Florian Toth, Krisztian Lorincz, Csaba Hegedus, Emmanuel Robbe, Georg Emil Frater
  • Publication number: 20140235914
    Abstract: 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: Application
    Filed: February 19, 2013
    Publication date: August 21, 2014
    Applicant: BASF Corporation
    Inventor: Joseph C. Dellamorte
  • Patent number: 8722950
    Abstract: 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: Grant
    Filed: April 26, 2010
    Date of Patent: May 13, 2014
    Assignee: Saudi Basic Industries Corporation
    Inventors: Jaap W. van Hal, Scott A. Stevenson, Jim Allman, David L. Sullivan, Travis Conant
  • Patent number: 8704028
    Abstract: 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: Grant
    Filed: March 30, 2010
    Date of Patent: April 22, 2014
    Assignee: UOP LLC
    Inventors: Christopher P. Nicholas, Etienne Mazoyer, Mostafa Taoufik, Jean-Marie Basset, Paul T. Barger
  • Patent number: 8704029
    Abstract: 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: Grant
    Filed: March 30, 2010
    Date of Patent: April 22, 2014
    Assignee: UOP LLC
    Inventors: Christopher P. Nicholas, Etienne Mazoyer, Mostafa Taoufik, Jean-Marie Basset, Paul T. Barger, James E. Rekoske
  • Patent number: 8674155
    Abstract: 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: Grant
    Filed: December 22, 2010
    Date of Patent: March 18, 2014
    Assignee: Kellogg Brown & Root, LLC
    Inventor: Curtis N. Eng
  • Publication number: 20140046110
    Abstract: 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: Application
    Filed: April 27, 2012
    Publication date: February 13, 2014
    Applicant: BASF SE
    Inventors: Stefan Iselborn, Michael Hesse, Piotr Makarczyk
  • Patent number: 8598400
    Abstract: 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: Grant
    Filed: February 8, 2011
    Date of Patent: December 3, 2013
    Assignees: Massachusetts Institute of Technology, Trustees of Boston College
    Inventors: Amir H. Hoveyda, Simon J. Meek, Robert V. O'Brien, Josep Llaveria Cros, Richard R. Schrock
  • Patent number: 8552242
    Abstract: 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: Grant
    Filed: February 8, 2011
    Date of Patent: October 8, 2013
    Assignees: Massachusetts Institute of Technology, Trustees of Boston College
    Inventors: Amir H. Hoveyda, Simon J. Meek, Robert V. O'Brien, Josep Llaveria Cros, Richard R. Schrock
  • Patent number: 8440874
    Abstract: 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: Grant
    Filed: September 4, 2009
    Date of Patent: May 14, 2013
    Assignees: Lummus Technology Inc., BASF Corporation
    Inventors: Bala Ramachandran, Sukwon Choi, Robert J. Gartside, Shane Kleindienst, Wolfgang Ruettinger, Saeed Alerasool
  • Patent number: 8395005
    Abstract: 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: Grant
    Filed: October 13, 2010
    Date of Patent: March 12, 2013
    Assignees: Equistar Chemicals, LP, Lyondell Chemical Technology, L.P.
    Inventors: Steven T. Coleman, Gary A. Sawyer, Robert S. Bridges
  • Patent number: 8389784
    Abstract: 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: Grant
    Filed: November 13, 2006
    Date of Patent: March 5, 2013
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Toshihiro Takai, Daisuke Mochizuki, Michiaki Umeno
  • Patent number: 8389788
    Abstract: 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: Grant
    Filed: March 30, 2010
    Date of Patent: March 5, 2013
    Assignee: UOP LLC
    Inventors: Mostafa Taoufik, Etienne Mazoyer, Christopher P. Nicholas, Jean-Marie Basset
  • Patent number: 8362311
    Abstract: 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: Grant
    Filed: September 30, 2009
    Date of Patent: January 29, 2013
    Assignees: Massachusetts Institute of Technology, Trustees of Boston College
    Inventors: Richard R. Schrock, Annie J. King, Yu Zhao, Margaret M. Flook, Amir H. Hoveyda
  • Publication number: 20120316374
    Abstract: 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: Application
    Filed: June 9, 2011
    Publication date: December 13, 2012
    Applicant: UOP LLC
    Inventors: Mostafa Taoufik, Etienne Mazoyer, Christopher P. Nicholas, Jean-Marie Basset
  • Patent number: 8324440
    Abstract: 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: Grant
    Filed: February 5, 2010
    Date of Patent: December 4, 2012
    Assignee: UOP LLC
    Inventors: Kristoffer E. Popp, Mark A. Krawczyk, Christopher P. Nicholas, Jennifer F. Abrahamian
  • Publication number: 20120264990
    Abstract: 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: Application
    Filed: April 14, 2011
    Publication date: October 18, 2012
    Applicant: UOP LLC
    Inventors: Christopher P Nicholas, Mark A. Krawczyk, Kristoffer E. Popp, Jennifer F. Abrahamian
  • Patent number: 8119852
    Abstract: 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: Grant
    Filed: December 11, 2007
    Date of Patent: February 21, 2012
    Assignee: BP Oil International Limited
    Inventors: Jean Marie Basset, Francois Stoffelbach, Mostafa Taoufik, Jean Thivolle-Cazat
  • Patent number: 8013200
    Abstract: 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: Grant
    Filed: April 18, 2008
    Date of Patent: September 6, 2011
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Toshihiro Takai, Hirokazu Ikenaga, Makoto Kotani, Shigeaki Fujii
  • Publication number: 20110196184
    Abstract: 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: Application
    Filed: February 5, 2010
    Publication date: August 11, 2011
    Applicant: UOP LLC
    Inventors: Kristoffer E. POPP, Mark A. KRAWCZYK, Christopher P. NICHOLAS, Jennifer F. ABRAHAMIAN
  • Publication number: 20110196185
    Abstract: 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: Application
    Filed: February 5, 2010
    Publication date: August 11, 2011
    Applicant: UOP LLC
    Inventors: Mark A. KRAWCZYK, Kristoffer E. POPP, Christopher P. NICHOLAS, Jennifer F. ABRAHAMIAN
  • Patent number: 7977522
    Abstract: 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: Grant
    Filed: February 24, 2006
    Date of Patent: July 12, 2011
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Toshihiro Takai, Takeshi Kubota
  • Patent number: 7960599
    Abstract: 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: Grant
    Filed: January 13, 2004
    Date of Patent: June 14, 2011
    Assignee: Elevance Renewable Sciences, Inc.
    Inventors: James R. Millis, Michael J. Tupy, Timothy W. Abraham, Mervyn L. De Souza
  • Publication number: 20110098496
    Abstract: 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: Application
    Filed: October 26, 2010
    Publication date: April 28, 2011
    Applicant: IFP ENERGIES NOUVELLES
    Inventors: Ludovic Chahen, Mikael Berthod, Helene Olivier-Bourbigou
  • Patent number: 7923588
    Abstract: 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: Grant
    Filed: October 13, 2005
    Date of Patent: April 12, 2011
    Assignee: BASF SE
    Inventors: Jürgen Stephan, Andreas Brodhagen, Markus Schubert, Frank Poplow, Michael Röper, Thomas Hill
  • Patent number: 7905288
    Abstract: 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: Grant
    Filed: November 25, 2008
    Date of Patent: March 15, 2011
    Assignee: Los Alamos National Security, LLC
    Inventor: Scott A. Kinkead
  • Patent number: 7868216
    Abstract: 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: Grant
    Filed: December 23, 2005
    Date of Patent: January 11, 2011
    Assignee: IFP Energies Nouvelles
    Inventors: Jean-Alain Chodorge, Christian Dupraz
  • Publication number: 20100145126
    Abstract: 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: Application
    Filed: February 24, 2006
    Publication date: June 10, 2010
    Applicant: MITSUI CHEMICALS, INC.
    Inventors: Toshihiro Takai, Takeshi Kubota
  • Patent number: 7696398
    Abstract: 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: Grant
    Filed: September 26, 2003
    Date of Patent: April 13, 2010
    Assignee: Dow GlobalTTechnologies, Inc.
    Inventors: Kenneth A. Burdett, Rob R. Maughon, Patrick H. Au-Yeung
  • Patent number: 7683180
    Abstract: 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: Grant
    Filed: April 16, 2002
    Date of Patent: March 23, 2010
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Donald W. Ward, Thomas J. Seiders, Steven D. Goldberg
  • Publication number: 20100063339
    Abstract: 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: Application
    Filed: April 18, 2008
    Publication date: March 11, 2010
    Applicant: MITSUI CHEMICALS, INC.
    Inventors: Toshihiro Takai, Hirokazu Ikenaga, Makoto Kotani, Shigeaki Fujii
  • Publication number: 20100056839
    Abstract: 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: Application
    Filed: September 4, 2009
    Publication date: March 4, 2010
    Applicants: LUMMUS TECHNOLOGY INC., BASF CATALYSTS LLC
    Inventors: Bala Ramachandran, Sukwon Choi, Robert J. Gartside, Shane Kleindienst, Wolfgang Ruettinger, Saeed Alerasool
  • Publication number: 20100030003
    Abstract: 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: Application
    Filed: December 11, 2007
    Publication date: February 4, 2010
    Applicant: BP OIL INTERNATIONAL LIMITED
    Inventors: Jean-Marie Basset, Francois Stoffelbach, Mostafa Taoufik, Jean Thivolle-Cazat
  • Patent number: 7638672
    Abstract: 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: Grant
    Filed: June 27, 2005
    Date of Patent: December 29, 2009
    Assignee: CPE Lyon Formation Continue et et Recherche CPE Lyon FCR
    Inventors: Christophe Coperet, Jean-Marie Basset, Jean Thivolle-Cazat, Erwan Le Roux, Mostafa Taoufik
  • Patent number: 7635794
    Abstract: 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: Grant
    Filed: July 1, 2005
    Date of Patent: December 22, 2009
    Assignee: CPE Lyon Formation Continue ET Recherche-CPE Lyon FCR
    Inventors: Jean-Marie Basset, Jean Thivolle-Cazat, Mostafa Taoufik, Erwan Le Roux, Christophe Coperet
  • Publication number: 20090281364
    Abstract: A method for metathesizing at least two gaseous olefins using a moving catalyst bed gas phase metathesis reactor and counter current flowing subdivided solid catalyst.
    Type: Application
    Filed: May 12, 2008
    Publication date: November 12, 2009
    Inventor: Richard B. Halsey
  • Patent number: 7601881
    Abstract: A catalyst and process is disclosed to selectively upgrade a paraffinic feedstock to obtain an isoparaffin-rich product for blending into gasoline. The catalyst comprises a support of a tungstated oxide or hydroxide of a Group IVB (IUPAC 4) metal, a phosphorus component, and at least one platinum-group metal component which is preferably platinum. The catalyst has a structure other than a heteropoly anion structure.
    Type: Grant
    Filed: January 30, 2008
    Date of Patent: October 13, 2009
    Assignee: UOP LLC
    Inventors: Ralph D. Gillespie, Feng Xu
  • Patent number: 7576251
    Abstract: 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: Grant
    Filed: April 15, 2005
    Date of Patent: August 18, 2009
    Assignee: ABB Lummus Global Inc.
    Inventors: Robert J. Gartside, Thomas P. Skourlis, Hassan Kaleem
  • Publication number: 20090203950
    Abstract: A method for metathesizing at least two olefins using a fluidized bed metathesis reactor and a finely subdivided solid catalyst.
    Type: Application
    Filed: February 12, 2008
    Publication date: August 13, 2009
    Inventors: Richard B. Halsey, Steven T. Coleman
  • Patent number: 7550638
    Abstract: An integrated method that comprises a hydrocarbon thermal cracking operation to form at least one olefin product, coupled with dimerization and metathesis operations, the dimerization operation forming additional feed material for the metathesis operation, and the metathesis operation forming additional amounts of olefin product.
    Type: Grant
    Filed: November 16, 2005
    Date of Patent: June 23, 2009
    Assignee: Equistar Chemicals, LP
    Inventors: Robert S. Bridges, Steven T. Coleman
  • Publication number: 20080188696
    Abstract: 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: Application
    Filed: October 13, 2005
    Publication date: August 7, 2008
    Applicant: BASF Aktiengesellschaft
    Inventors: Jurgen Stephan, Andreas Brodhagen, Markus Schubert, Frank Poplow, Michael Roper, Thomas Hill
  • Publication number: 20080132744
    Abstract: A process is described for the preparation of a heterogeneous catalyst containing rhecnium as active component and C)an inert carrier medium. characterized in that said inert carrier is previously treated with a silanizing compound containing chlorine, before the laying of the active component on the carrier, and the activation of the heterogeneous catalyst takes place by means of thermal treatment followed by a rapid final cooling. The catalyst is particularly active in metathesis reactions of olefins.
    Type: Application
    Filed: October 26, 2004
    Publication date: June 5, 2008
    Applicant: POLIMERI EUROPA S.p.A.
    Inventors: Cecilia Querci, Aldo Bosetti, Rinaldo Guerrini, Francesco Panella, Matteo Russo