Using Re-containing Catalyst Patents (Class 585/647)
  • Patent number: 9029619
    Abstract: The present invention relates to a process to make alpha olefins comprising: dehydrating ethanol to recover an ethylene stream, introducing said ethylene stream into an oligomerization zone containing an oligomerization catalyst and into contact with said oligomerization catalyst, operating said oligomerization zone at conditions effective to produce an effluent consisting essentially of 1-butene, 1-hexene, optionally heavier alpha olefins and unconverted ethylene if any, introducing the above effluent into a fractionation zone to recover a stream consisting essentially of 1-butene, a stream consisting essentially of 1-hexene, optionally a stream consisting essentially of heavier alpha olefins and an optional ethylene stream. In an advantageous embodiment the 1-hexene or at least one heavier alpha olefins, if any, are isomerized to an internal olefin and subsequently transformed by metathesis with the aid of additional ethylene into different alpha-olefins with even or odd number of carbons.
    Type: Grant
    Filed: December 10, 2009
    Date of Patent: May 12, 2015
    Assignee: Total Research & Technology Feluy
    Inventor: Walter Vermeiren
  • 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: 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: 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: 20130150643
    Abstract: Methods for olefin metathesis including contacting a olefin feed stream with a metathesis catalyst at a temperature and at a pressure sufficient to maintain the reactor olefin compositions in a mixed-phase condition including components in the liquid phase and components in the vapor phase, where the mixed-phase reaction conditions shift the equilibrium to desired product olefins.
    Type: Application
    Filed: December 8, 2011
    Publication date: June 13, 2013
    Applicant: SAUDI BASIC INDUSTRIES CORPORATION
    Inventors: Travis Conant, Scott A. Stevenson
  • 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: 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
  • 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
  • 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
  • Patent number: 7767170
    Abstract: A process is provided for cracking hydrocarbon feedstock containing resid comprising: heating the feedstock, mixing the heated feedstock with a fluid and/or a primary dilution steam stream to form a mixture, optionally further heating the mixture, flashing the mixture within a flash/separation vessel to form a vapor phase and a liquid phase, partially condensing the vapor phase by contacting with a condenser within the vessel, to condense at least some coke precursors within the vapor while providing condensates which add to the liquid phase, removing the vapor phase of reduced coke precursors content as overhead and the liquid phase as bottoms, heating the vapor phase, cracking the vapor phase in a radiant section of a pyrolysis furnace to produce an effluent comprising olefins, and quenching the effluent and recovering cracked product therefrom. An apparatus for carrying out the process is also provided.
    Type: Grant
    Filed: June 16, 2006
    Date of Patent: August 3, 2010
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Richard C. Stell, George Stephens, Jennifer L. Bancroft, John R. Messinger
  • Publication number: 20100191030
    Abstract: A metathesis catalyst which is a combination including a catalyst 1 comprising a compound that contains at least one metal element selected from tungsten, molybdenum and rhenium and a catalyst 2 comprising at least one selected from magnesium oxide and calcined hydrotalcite is easily and effectively reactivated from a degraded state due to long-term repetitive cycles of reaction and regeneration at high temperature for burning off poisonous substances or cokes, to like-new condition or a desired level. An olefin production process by a metathesis reaction includes a step of performing the reactivation. A degraded metathesis catalyst is easily and effectively reactivated by being contacted with water at not more than 50° C. or water vapor at not more than 170° C.
    Type: Application
    Filed: June 23, 2008
    Publication date: July 29, 2010
    Inventor: Hirokazu Ikenaga
  • 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
  • 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
  • Patent number: 7625480
    Abstract: The invention relates to a method for processing asphaltene-containing feed to a pyrolysis furnace by raising the final boiling point of the feed/steam mixture to the pyrolysis furnace to ensure fouling occurs lower in the convection section where the mixture of air and steam can burn off fouling deposits during decoking operations. The final boiling point of the feed stream is increased by adding a heavy essentially asphaltene-free high boiling point hydrocarbon to the feed stream before the feed stream enters the convection section of the pyrolysis furnace, whereby said fouling occurs lower in the convection section.
    Type: Grant
    Filed: May 11, 2006
    Date of Patent: December 1, 2009
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: David Beattie, Richard Charles Stell, James N. McCoy, Bryan Daniel McVicker, Paul F. Keusenkothen, Alok Srivastava, David Bleckinger
  • 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
  • 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
  • Patent number: 7235705
    Abstract: A process for reducing fouling during cracking of a hydrocarbon feedstock containing resid is provided which comprises: introducing a mixture stream of heated hydrocarbon feedstock mixed with steam to a flash/separation apparatus to form i) a vapor phase at its dew point which partially cracks causing a temperature decrease and partial condensation of said vapor phase in the absence of added heat, and ii) a liquid phase. Partial condensation is reduced by adding a heated vaporous diluent, e.g., light hydrocarbon or superheated steam, to the flash/separation apparatus to an extent sufficient to at least partially compensate for the temperature decrease and to dilute and superheat the vapor phase, prior to removing the vapor phase as overhead for subsequent cracking and recovery of cracked product. An apparatus for carrying out the process is also provided.
    Type: Grant
    Filed: May 21, 2004
    Date of Patent: June 26, 2007
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventor: Richard C. Stell
  • Patent number: 7220887
    Abstract: A process for cracking hydrocarbon feedstock containing resid comprising: heating the feedstock, mixing the heated feedstock with a fluid and/or a primary dilution steam stream to form a mixture, flashing the mixture to form a vapor phase and a liquid phase which collect as bottoms and removing the liquid phase, separating and cracking the vapor phase, and cooling the product effluent, wherein the bottoms are maintained under conditions to effect at least partial visbreaking. The visbroken bottoms may be steam stripped to recover the visbroken molecules while avoiding entrainment of the bottoms liquid. An apparatus for carrying out the process is also provided.
    Type: Grant
    Filed: May 21, 2004
    Date of Patent: May 22, 2007
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Richard C. Stell, George J. Balinsky, James N. McCoy, Paul F. Keusenkothen
  • Patent number: 7145050
    Abstract: The invention relates to modified supported catalysts based on Re2O7/?-Al2O3 for use in the preparation of cycloalkadienes in a metathesis reaction, a process for preparing cycloalkadienes in the presence of these supported catalysts and the use of the resulting cycloalkadienes for the preparation of fragrances.
    Type: Grant
    Filed: August 23, 2002
    Date of Patent: December 5, 2006
    Assignee: Symrise GmbH & Co. KG
    Inventors: Ingo Wöhrle, Aurélia Reckziegel, Peter Esser, Martin Stürmann
  • Patent number: 7041864
    Abstract: Ring opening cross metathesis of secondary non-cyclic hydrocarbons with cyclic unsaturated hydrocarbons having 8 carbon atoms or more to produce corresponding unsaturated product hydrocarbons having more than 8 carbon atoms.
    Type: Grant
    Filed: December 11, 2002
    Date of Patent: May 9, 2006
    Assignee: Shell Oil Company
    Inventors: Howard Lam-ho Fong, Michael Wayne Potter, David Stephen Brown
  • Patent number: 6977318
    Abstract: A method for forming propylene wherein ethylene is employed as a primary feed material in a combination of steps comprising dehydration, skeletal isomerization, and metathesis to form a versatile product mix that can contain one or more of propylene, gasoline, MTBE, and propylene oxide.
    Type: Grant
    Filed: May 4, 2004
    Date of Patent: December 20, 2005
    Assignee: Equistar Chemicals, LP
    Inventor: Robert S. Bridges
  • Patent number: 6916966
    Abstract: The present invention relates to a process for preparing cycloalkadienes using supported catalysts based on Re2O7/?-Al2O3 and also to the use of the resulting cycloalkadienes for the preparation of fragrances.
    Type: Grant
    Filed: August 23, 2002
    Date of Patent: July 12, 2005
    Assignee: Symrise GmbH & Co. KG
    Inventors: Ingo Wöhrle, Peter Esser, Aurélia Reckziegel, Matthias Brandt, Stephan Klein, Thomas Turek
  • Patent number: 6903241
    Abstract: The present invention relates to supported catalysts based on Re2O7/(—Al2O3 for use in the preparation of cycloalkadienes in a metathesis reaction, a process for preparing cycloalkadienes in the presence of these supported catalysts and also the use of the resulting cycloalkadienes for preparing fragrances.
    Type: Grant
    Filed: August 23, 2002
    Date of Patent: June 7, 2005
    Assignee: Symrise GmbH & Co. KG
    Inventors: Ingo Wöhrle, Peter Esser, Aurélia Reckziegel, Matthias Brandt, Stephan Klein, Thomas Turek
  • Patent number: 6852900
    Abstract: The present invention relates to a process for the metathesis reaction of unsaturated organic compounds.
    Type: Grant
    Filed: March 1, 2001
    Date of Patent: February 8, 2005
    Assignee: Merck Patent GmbH
    Inventors: Hanns Wurziger, Guido Pieper, Norbert Schwesinger
  • Publication number: 20040260135
    Abstract: Process for preparing a supported catalyst (catalyst C) comprising a support (support S) and an active component (activator A), wherein
    Type: Application
    Filed: April 8, 2004
    Publication date: December 23, 2004
    Applicant: BASF Aktiengesellschaft
    Inventors: Markus Schubert, Michael Hesse, Jurgen Stephan, Volker Bohm, Andreas Brodhagen, Frank Poplow, Martina Sinner-Lang, Uwe Diehlmann, Gerhard Cox, Jochen Pfeifer
  • Patent number: 6777582
    Abstract: A C3 to C6 hydrogen cut from a cracking unit is processed for the conversion of olefins to propylene and hexene via autometathesis. The autometathesis of a mixed normal butenes feed in the presence of a metathesis catalyst operates without any ethylene in the feed mix to the metathesis reactor. Some fraction of the 2-butene feed may be isomerized to 1-butene and the 1-butene formed plus the 1-butene in the feed react rapidly with the 2-butene to form propylene and 2-pentene. The feed to the reactor also includes the recycle of the 2-pentene formed in the reactor with unreacted butenes to simultaneously form additional propylene and hexene. In one embodiment, some or all of the 3-hexene formed in the reaction is isomerized to 1-hexene. In another embodiment, some portion of the 3-hexene produced in the main metathesis reaction is reacted with ethylene to produce 1-butene without the need for superfractionation.
    Type: Grant
    Filed: March 7, 2002
    Date of Patent: August 17, 2004
    Assignee: ABB Lummus Global Inc.
    Inventors: Robert J. Gartside, Marvin I. Greene, Quincy J. Jones
  • Patent number: 6743958
    Abstract: For the selective production of propylene from an olefinic C4 fraction, a process is implemented that successively comprises: 1) the selective hydrogenation of butadiene with isomerization of butene-1 into butene-2; 2) the separation by distillation of a mixture that is rich in isobutene and butene-1 at the top and a fraction that is rich in butene-2 at the bottom; 3) the skeletal isomerization of isobutene into n-butenes on the top fraction, with recycling in stage 1; and 4) the metathesis of the butene-2-rich fraction with ethylene.
    Type: Grant
    Filed: May 2, 2001
    Date of Patent: June 1, 2004
    Assignee: Institut Francais du Petrole
    Inventors: Dominique Commereuc, Christine Travers
  • Patent number: 6727396
    Abstract: Ethylene and hexene-1 are produced from butene-1 by metathesis of butene-1 and isomerization of the hexene-3 produced therein to hexene-1. The initial starting material is a mixed butene stream wherein butene-1 is isomerized to butene-2 with isobutylene being separated therefrom, followed by isomerization of butene-2 to butene-1, with the butene-1 being the feed to the metathesis.
    Type: Grant
    Filed: January 23, 2002
    Date of Patent: April 27, 2004
    Assignee: ABB Lummus Global, Inc.
    Inventor: Robert J. Gartside
  • Patent number: 6686510
    Abstract: A process for production, from an olefinic C4 fraction, on the one hand, of high-purity isobutene and, on the other hand, of propylene by metathesis is described. The process comprises three successive stages: 1) the selective hydrogenation of butadiene with isomerization of butene-1 into butene-2 up to thermodynamic equilibrium; 2) the separation by isobutene at the column head that integrates the hydroisomerization of n-butenes, allowing a butene-2 fraction at the bottom, and 3) the metathesis of the butene-2 fraction with ethylene. By this process, it is possible to produce in a very selective way high-purity isobutene and polymerization-quality propylene.
    Type: Grant
    Filed: December 26, 2000
    Date of Patent: February 3, 2004
    Assignee: Institut Français du Petrole
    Inventors: Dominique Commereuc, Blaise Didillon, Helene Olivier-Bourbigou, Lucien Saussine
  • Patent number: 6677495
    Abstract: A process for preparing cyclopentene oligomer mixtures of the formula I comprises reacting in a homogeneously or heterogeneously catalyzed metathesis reaction a hydrocarbon mixture which contains cyclopentene and acyclic monoolefins and which originates from petroleum processing by cracking (C5 fraction); cyclopentene oligomers of the formula I obtainable by this process and their use are also described.
    Type: Grant
    Filed: June 21, 1999
    Date of Patent: January 13, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Schwab, Martin Schäfer, Arthur Höhn
  • Patent number: 6646172
    Abstract: A multistage process for preparing propene, in which the first stage is the reaction of 1-butene, 2-butene and isobutene to give propene, 2-pentene and 2-methyl-2-butene in the presence of a metathesis catalyst comprising at least one compound of a metal of transition group VIb, VIIb or VIII of the Periodic Table of the Elements; the second stage is separation of the propene and 2-pentene/2-methyl-2-butene formed; the third stage is reaction of the 2-pentene and 2-methyl-2-butene with ethehe to give propene, 1-butene and isobutene in the presence of a metathesis catalyst comprising at least one compound of a metal of transition group VIb, VIIb or VIII of the Periodic Table of the Elements; the fourth stage is separation of the propene and 1-butene/isobutene formed and returning the 1-butene and isobutene formed to the first stage.
    Type: Grant
    Filed: October 8, 1998
    Date of Patent: November 11, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Schwab, Michael Schulz
  • Publication number: 20030204123
    Abstract: The metathesis process is used: (A) for the production of propylene from the metathesis of 2-butene and ethylene wherein the propylene product is removed concurrently by fractional distillation by which the removal of the propylene product disturbs the equilibrium concentration and allows for higher conversions; (B) for the production of detergent range olefins from the metathesis of C15 and heavier olefins with C9 and lighter olefins wherein the detergent range olefin product is removed concurrently by fractional distillation in which the removal of the detergent range olefin product disturbs the equilibrium concentration and allows for higher conversions with less side reactions; (C) for the production of 2-methyl-2-butene and propylene from the metathesis of 2-butene and isobutylene wherein the propylene product and 2-methyl-2-butene product is removed concurrently by fractional distillation in which the removal of the product disturbs the equilibrium concentration and allows for higher conversions; and (D
    Type: Application
    Filed: May 7, 2003
    Publication date: October 30, 2003
    Applicant: CATALYTIC DISTILLATION TECHNOLOGIES
    Inventor: Gary G. Podrebarac
  • Publication number: 20030204124
    Abstract: The metathesis process is used: (A) for the production of propylene from the metathesis of 2-butene and ethylene wherein the propylene product is removed concurrently by fractional distillation by which the removal of the propylene product disturbs the equilibrium concentration and allows for higher conversions; (B) for the production of detergent range olefins from the metathesis of C15 and heavier olefins with C9 and lighter olefins wherein the detergent range olefin product is removed concurrently by fractional distillation in which the removal of the detergent range olefin product disturbs the equilibrium concentration and allows for higher conversions with less side reactions; (C) for the production of 2-methyl-2-butene and propylene from the metathesis of 2-butene and isobutylene wherein the propylene product and 2-methyl-2-butene product is removed concurrently by fractional distillation in which the removal of the product disturbs the equilibrium concentration and allows for higher conversions; and (D
    Type: Application
    Filed: May 7, 2003
    Publication date: October 30, 2003
    Applicant: CATALYTIC DISTILLATION TECHNOLOGIES
    Inventor: Gary G. Podrebarac
  • Patent number: 6639116
    Abstract: Novel condensation reactions used to produce 1,3-cyclohexadiene. Such a compound is an important precursor in the manufacture of high performance plastics, as one example, are provided. In the past, the production methods for such 1,3-cyclohexadiene required very complex reactions involving numerous process steps. Such a method has proven costly, difficult to properly monitor and control, and less than reliable to provide even low amounts of such a precursor compound. The inventive production methods thus permit a reduction in complexity and cost, and, with a single reaction step, facilitate quality measurements as to the product purity itself.
    Type: Grant
    Filed: March 15, 2002
    Date of Patent: October 28, 2003
    Assignee: Millken & Company
    Inventors: John G. Lever, Kenneth Wagner, John C. Sworen
  • Patent number: 6624338
    Abstract: The present invention provides a catalyst and a process for metathesis of olefinic C4 cuts. The catalyst contains rhenium, caesium and delta alumina. The preferred catalyst contains at least one rhenium compound deposited on a support principally composed of alumina, treated at a temperature of more than 750° C., and modified by at least one caesium compound. Thus the duration of the cycle between two regeneration operations is substantially increased. Application to a process for the production of propylene from an olefinic C4 cut in three steps: selective hydrogenation of butadiene with isomerisation of 1-butene to 2-butene, separation by distillation of the major portion of the isobutene, and metathesis of the cut rich in 2-butene with ethylene.
    Type: Grant
    Filed: July 3, 2001
    Date of Patent: September 23, 2003
    Assignee: Institut Francais du Petrole
    Inventors: Dominique Commereuc, François Hugues, Lucien Saussine
  • Publication number: 20030176754
    Abstract: A C3 to C6 hydrogen cut from a cracking unit is processed for the conversion of olefins to propylene and hexene via autometathesis. The autometathesis of a mixed normal butenes feed in the presence of a metathesis catalyst operates without any ethylene in the feed mix to the metathesis reactor. Some fraction of the 2-butene feed may be isomerized to 1-butene and the 1-butene formed plus the 1-butene in the feed react rapidly with the 2-butene to form propylene and 2-pentene. The feed to the reactor also includes the recycle of the 2-pentene formed in the reactor with unreacted butenes to simultaneously form additional propylene and hexene. In one embodiment, some or all of the 3-hexene formed in the reaction is isomerized to 1-hexene. In another embodiment, some portion of the 3-hexene produced in the main metathesis reaction is reacted with ethylene to produce 1-butene without the need for superfractionation.
    Type: Application
    Filed: March 7, 2002
    Publication date: September 18, 2003
    Inventors: Robert J. Gartside, Marvin I. Greene, Quincy J. Jones
  • Publication number: 20030163011
    Abstract: The present invention relates to a process for the metathesis reaction of unsaturated organic compounds.
    Type: Application
    Filed: January 14, 2003
    Publication date: August 28, 2003
    Inventors: Hanns Wurziger, Guido Pieper, Norbert Schwesinger
  • Publication number: 20030135080
    Abstract: The invention provides a homogeneous metathesis process for converting C4 to C10 olefins in a Fischer-Tropsch derived feedstock to C6 to C18 olefins, wherein a higher transitions group metal catalyst is used to metathesize a double bond on a linear portion of the olefin, provided that the double bond is at least three carbons away from a branch if the olefin is branched. The catalyst may include a metal-alkylidene complex and the metal may be ruthenium, osmium, tungsten, or iridium. A suitable catalyst is a Grubbs catalyst. The metathesis process includes a recycle process to maintain the reaction equilibrium, although ethylene can be extracted from the process if a recycle process is not used. A co-solvent is used to increase the product yield. The C6 to C18 olefin produced by the above process may be suitable for use as drilling fluids.
    Type: Application
    Filed: December 19, 2002
    Publication date: July 17, 2003
    Inventors: Jan Mattheus Botha, Jan Petrus Karel Reynhardt, Charl Van Schalkwyk, Hermanus Cornelius Moolman Vosloo
  • Patent number: 6586649
    Abstract: The invention provides a process for the production of propylene by butene metathesis. The process includes contacting a feedstock, which contains butene selected from 1-butene, 2-butene and mixtures thereof, with a catalyst which includes a catalytic amount of at least one metal oxide selected from oxides of the transition metals. The contacting is under reaction conditions which include a temperature of 300-600 øC. and a pressure of 1 20 atmospheres, and converts the butene to propylene, thereby to produce a reaction product containing propylene. C5— and higher hydrocarbons produced by the metathesis are separated from the reaction product and are recycled to the reaction where they are contacted with the catalyst.
    Type: Grant
    Filed: July 12, 2001
    Date of Patent: July 1, 2003
    Assignee: Sasol Technology (Proprietary) Limited
    Inventors: Jan Mattheus Botha, Muzikayise Mthokozisi Justice Mbatha, Bongani Simon Nkosi, Alta Spamer, Joan Swart
  • Patent number: 6583329
    Abstract: The metathesis process is carried out in a reaction distillation column for: (A) for the production of propylene from the metathesis of 2-butene and ethylene; (B) for the production of detergent range olefins from the metathesis of C15 and heavier olefins with C9 and lighter olefins; (C) for the production of 2-methyl-2-butene and propylene from the metathesis of 2-butene and isobutylene and (D) for the production of tetramethylethylene from the metathesis of isobutylene with itself and/or the reaction of diisobutylene with the ethylene produced to produce neohexene.
    Type: Grant
    Filed: March 4, 1998
    Date of Patent: June 24, 2003
    Assignee: Catalytic Distillation Technologies
    Inventor: Gary G. Podrebarac
  • Patent number: 6580009
    Abstract: The process for preparing propene and hexene from a raffinate II feed stream comprising olefinic C4-hydrocarbons comprises a) a metathesis reaction in which butenes present in the feed stream are reacted with ethene in the presence of a metathesis catalyst comprising at least one compound of a metal of transition groups VIb, VIIb or VIII of the Periodic Table of the Elements to give a mixture comprising ethene, propene, butenes, 2-pentene, 3-hexene and butanes, using, based on the butenes, from 0.05 to 0.
    Type: Grant
    Filed: March 12, 2001
    Date of Patent: June 17, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Schwab, Ralf Schulz, Sylvia Huber
  • Patent number: 6566568
    Abstract: A process for preparing a paraffinic product stream in the gasoline, middle distillate fuel and lube ranges from a C2-5-containing feedstock and a C20+ paraffinic feedstock is described. The combined feedstocks are subjected to molecular averaging via dehydrogenation to form olefins, metathesis of the olefins, and rehydrogenation of the olefins to form paraffins. The product stream includes a fraction rich in paraffins the molecular weights of which are between those of the light and heavy paraffin feedstocks, plus some unconverted feeds. The product of the molecular averaging reaction can optionally be isomerized to improve the octane value, in the case of gasoline, or pour point, in the case of middle distillate fuels and lubes. The unconverted feedstocks can be recycled to extinction.
    Type: Grant
    Filed: December 19, 2001
    Date of Patent: May 20, 2003
    Assignee: Chevron U.S.A. Inc.
    Inventor: Cong-Yan Chen
  • Patent number: 6538168
    Abstract: A process for preparing C5/C6-olefins from an olefinic starting stream comprising C4-hydrocarbons comprises a) carrying out a metathesis reaction in the presence of a metathesis catalyst so as to convert the 1-butene, 2-butene and isobutene present in the starting stream into a mixture of C2-C6-olefins and butanes, b) firstly fractioning the resulting product stream by distillation to give a low boiler fraction A comprising C2-C4-olefins and butanes or C2-C3-olefins, which is discharged, and a high boiler fraction comprising C4-C8-olefins and butanes, c) fractioning the high boiler fraction from b) by distillation to give a low boiler fraction B comprising butenes and butanes, an intermediate boiler fraction C comprising pentene and methylbutene and a high boiler fraction D comprising hexane and methylpentene, d) where all or part of the fraction B and/or C are recirculated to the process step a) and the fraction D is discharged as product.
    Type: Grant
    Filed: July 6, 2000
    Date of Patent: March 25, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Schwab, Michael Schulz, Ralf Schulz, Sylvia Huber
  • Publication number: 20030028063
    Abstract: An olefin metathesis catalyst consists essentially of a transition metal or oxide thereof supported on a high purity silica support possessing low amounts of acidic or basic sites such that in the reaction of pure butene-1 over said catalyst under metathesis reaction conditions the reaction possesses a weight selectivity to hexene-3 of at least 55 wt %.
    Type: Application
    Filed: June 13, 2001
    Publication date: February 6, 2003
    Inventors: Robert J. Gartside, Marvin I. Greene, Ali M. Khonsari, Lawrence L. Murrell
  • Publication number: 20020183578
    Abstract: For the selective production of propylene from an olefinic C4 fraction, a process is implemented that successively comprises:
    Type: Application
    Filed: May 2, 2001
    Publication date: December 5, 2002
    Applicant: Institut Francais du Petrole
    Inventors: Dominique Commereuc, Christine Travers
  • Publication number: 20020143222
    Abstract: The present invention provides a catalyst and a process for metathesis of olefinic C4 cuts. The catalyst contains rhenium, caesium and delta alumina. The preferred catalyst contains at least one rhenium compound deposited on a support principally composed of alumina, treated at a temperature of more than 750° C., and modified by at least one caesium compound. Thus the duration of the cycle between two regeneration operations is substantially increased. Application to a process for the production of propylene from an olefinic C4 cut in three steps: selective hydrogenation of butadiene with isomerisation of 1-butene to 2-butene, separation by distillation of the major portion of the isobutene, and metathesis of the cut rich in 2-butene with ethylene.
    Type: Application
    Filed: July 3, 2001
    Publication date: October 3, 2002
    Applicant: INSTITUT FRANCAIS DU PETROLE
    Inventors: Dominique Commereuc, Francois Hugues, Lucien Saussine
  • Publication number: 20020120173
    Abstract: Catalytic process for metathesis of olefins in the presence of a catalyst and a stabilizing agent that is injected into the reaction medium. Application in particular to rebalancing between one another the light olefins that are obtained from steam cracking or catalytic cracking (FCC), such as ethylene, propylene, butenes or pentenes.
    Type: Application
    Filed: January 28, 2000
    Publication date: August 29, 2002
    Inventors: Dominique Commereuc, Paul Mikitenko
  • Patent number: 6441263
    Abstract: A process for preparing an ethylene-rich composition from a C3-5 paraffinic feedstock is described. The C3-5 paraffinic feedstock is subjected to molecular redistribution via dehydrogenation to form olefins, metathesis of the olefins, and rehydrogenation of the olefins to form paraffins. The product stream includes ethane, which is isolated and sent to an ethane or ethane/propane cracker (or, alternatively, a flexi-cracker, although this is less cost effective) to yield an ethylene-rich composition. The product stream also includes C3-5 paraffins, which can be recycled, and C6+paraffins, which can be used, for example, as solvents. Alternatively, they can be isomerized to form gasoline additives, or can be converted to aromatic compounds by subjecting them to reforming conditions, for example using the AROMAX™ process or platforming or rheniforming conditions.
    Type: Grant
    Filed: July 7, 2000
    Date of Patent: August 27, 2002
    Assignee: ChevronTexaco Corporation
    Inventors: Dennis J. O'Rear, Rodney Porter, Cong-Yan Chen