Transition Metal Oxide Or Sulfide Agent Patents (Class 585/629)
  • Patent number: 11680030
    Abstract: Improved methods of oxidative dehydrogenation (ODH) of alkanes and alkylbenzenes to the corresponding olefins are disclosed. The disclosed methods use ozone (O3) to mediate the oxidative dehydrogenation reaction with high selectivity for the desired product, and no heterogeneous ODH catalyst is needed.
    Type: Grant
    Filed: April 13, 2022
    Date of Patent: June 20, 2023
    Assignee: WISCONSIN ALUMNI RESEARCH FOUNDATION
    Inventors: Ive Hermans, William McDermott, Edgard Lebron Rodriguez, Unni Ravi Kurumbail
  • Patent number: 11247195
    Abstract: A method of preparing a catalyst for oxidative dehydrogenation that includes coprecipitation and injecting inert gas or air at a specific time point to reduce the ratio of an inactive ?-Fe2O3 crystal structure, thereby improving the activity of the catalyst. Also provided is a method of performing oxidative dehydrogenation using the catalyst. When oxidative dehydrogenation of butene is performed using the catalyst, side reaction may be reduced, and selectivity for butadiene may be improved, providing butadiene with high productivity.
    Type: Grant
    Filed: April 26, 2018
    Date of Patent: February 15, 2022
    Assignee: LG CHEM, LTD.
    Inventors: Sang Jin Han, Dong Hyun Ko, Kyong Yong Cha, Jun Kyu Han, Sun Hwan Hwang
  • Patent number: 9233361
    Abstract: A hydrogen separation membrane including: a metal layer including the at least one Group 5 element; and a transition metal catalyst layer on the metal layer, the transition metal catalyst layer including at least one transition metal and at least one of phosphorus (P) or boron (B).
    Type: Grant
    Filed: February 11, 2014
    Date of Patent: January 12, 2016
    Assignee: SAMSUNG ELECTRONICS CO., LTD.
    Inventors: Keun woo Cho, Hyeon Cheol Park, Kyoung-Seok Moon, Kwang Hee Kim, Jae-Ho Lee, Eun Seog Cho
  • Publication number: 20150005532
    Abstract: The present invention relates to a process for the production of 1,3-butadiene which comprises the following phases: a) extracting, by means of extractive distillation, in an extraction section, an end-product containing 1,3-butadiene and a raffinate product, starting from mixtures of saturated and unsaturated compounds having from 2 to 10 carbon atoms in the chain; b) sending the raffinate product to a dehydrogenation section; c) dehydrogenating the raffinate product in the dehydrogenation section in the presence of a dehydrogenation catalyst and an inert product so as to form a reaction effluent containing 1,3-butadiene; d) recirculating the reaction effluent containing 1,3-butadiene directly to the extraction section after separating the incondensable compounds.
    Type: Application
    Filed: December 24, 2012
    Publication date: January 1, 2015
    Applicant: versalis S.p.A.
    Inventors: Alessandro Del Seppia, Fabio Assandri, Elena Ghirardo, Carmelo Vella
  • Patent number: 8546634
    Abstract: There is provided a method for production of a conjugated diene from a monoolefin having four or more carbon atoms by a fluidized bed reaction. The method for production of a conjugated diolefin includes bringing a catalyst in which an oxide is supported on a carrier into contact with a monoolefin having four or more carbon atoms in a fluidized bed reactor in which the catalyst and oxygen are present, wherein the method satisfies the following (1) to (3): (1) the catalyst contains Mo, Bi, and Fe; (2) a reaction temperature is in the range of 300 to 420° C.; and (3) an oxygen concentration in a reactor outlet gas is in the range of 0.05 to 3.0% by volume.
    Type: Grant
    Filed: September 29, 2010
    Date of Patent: October 1, 2013
    Assignee: Asahi Kasei Chemicals Corporation
    Inventors: Hideo Midorikawa, Hiroyuki Yano, Takashi Kinoshita
  • Patent number: 8524969
    Abstract: A method for the dehydrogenation of hydrocarbons to alkenes, such as n-pentene to piperylene and n-butane to butadiene at pressures less than atmospheric utilizing a dehydrogenation catalyst are disclosed. Embodiments involve operating the dehydrogenation reactor at a pressure of 1,000 mbar or less.
    Type: Grant
    Filed: July 21, 2009
    Date of Patent: September 3, 2013
    Assignee: Fina Technology, Inc.
    Inventors: James Butler, Olga Khabashesku, James T. Merrill
  • Patent number: 8513479
    Abstract: The present invention relates to a zinc ferrite catalyst, a method of producing the same, and a method of preparing 1,3-butadiene using the same. Specifically, the present invention relates to a zinc ferrite catalyst which is produced in a pH-adjusted solution using a coprecipitation method, a method of producing the same, and a method of preparing 1,3-butadiene using the same, in which the 1,3-butadiene can be prepared directly using a C4 mixture including n-butene and n-butane through an oxidative dehydrogenation reaction. The present invention is advantageous in that 1,3-butadiene can be obtained at a high yield directly using a C4 fraction without performing an additional process for separating n-butene, as a reactant, from a C4 fraction containing impurities.
    Type: Grant
    Filed: May 8, 2008
    Date of Patent: August 20, 2013
    Assignees: SK Global Chemical Co., Ltd, SK Innovation Co., Ltd.
    Inventors: Young Min Chung, Seong Jun Lee, Tae Jin Kim, Seung Hoon Oh, Yong Seung Kim, In Kyu Song, Hee Soo Kim, Ji Chul Jung, Ho Won Lee
  • Publication number: 20130165723
    Abstract: The present invention relates to a catalyst for the dehydrogenation of hydrocarbons which is based on iron oxide and additionally comprises at least one potassium compound, at least one cerium compound, from 0.7 to 10% by weight of at least one manganese compound, calculated as MnO2, and from 10 to 200 ppm of at least one titanium compound, calculated as TiO2, and also to a process for the production thereof. Furthermore, the present invention relates to a process for the catalytic dehydrogenation of hydrocarbons using the catalyst of the invention.
    Type: Application
    Filed: December 21, 2012
    Publication date: June 27, 2013
    Applicant: BASF SE
    Inventor: BASF SE
  • Publication number: 20120209048
    Abstract: A dehydrogenation catalyst is described that comprises an iron oxide, an alkali metal or compound thereof, and rhenium or a compound thereof. A process for preparing a dehydrogenation catalyst comprising preparing a mixture of iron oxide, an alkali metal or compound thereof, and rhenium or a compound thereof is also described. Additionally, a dehydrogenation process using the catalyst and a process for preparing polymers are described.
    Type: Application
    Filed: March 19, 2012
    Publication date: August 16, 2012
    Applicant: BASF Corporation
    Inventor: Ruth Mary Kowaleski
  • Patent number: 8188328
    Abstract: The present invention is an improved cyclic, endothermic hydrocarbon conversion process and a catalyst bed system for accomplishing the same. Specifically, the improved process comprises reacting a hydrocarbon with a multi-component catalyst bed in such a manner that the temperature within the catalyst bed remains within controlled temperature ranges throughout all stages of the process. The multi-component catalyst bed comprises a reaction-specific catalyst physically mixed with a heat-generating material.
    Type: Grant
    Filed: June 27, 2011
    Date of Patent: May 29, 2012
    Assignee: Sud-Chemie Inc.
    Inventors: Vladimir Fridman, Michael A. Urbancic
  • Publication number: 20110245568
    Abstract: A method for the dehydrogenation of n-butene to form butadiene over a dehydrogenation catalyst with a butadiene yield of at least 40 mol % is disclosed. Embodiments involve operating the dehydrogenation reactor at a pressure of 1,000 mbar or less.
    Type: Application
    Filed: April 27, 2011
    Publication date: October 6, 2011
    Applicant: Fina Technology, Inc.
    Inventors: Olga Khabashesku, James R. Butler, Dariusz Wachowicz
  • Patent number: 8003840
    Abstract: This invention relates to a bismuth molybdate catalyst, a preparation method thereof, and a method of preparing 1,3-butadiene using the same, and to a bismuth molybdate catalyst, a preparation method thereof, and a method of preparing 1,3-butadiene using the same, in which 1,3-butadiene can be prepared through oxidative dehydrogenation directly using a C4 mixture including n-butene and n-butane as a reactant in the presence of a mixed-phase bismuth molybdate catalyst including ?-bismuth molybdate (Bi2Mo3On) and ?-bismuth molybdate (Bi2MoO6). According to this invention, the C4 raffinate, containing many impurities, is used as a reactant, without an additional n-butane separation process, thus obtaining 1,3-butadiene at high yield.
    Type: Grant
    Filed: March 16, 2007
    Date of Patent: August 23, 2011
    Assignees: SK Innovation Co., Ltd., SK Global Chemical Co., Ltd.
    Inventors: Seung Hoon Oh, Seong Jun Lee, Tae Jin Kim, Ahn Seop Choi, Young Min Chung, In Kyu Song, Ji Chul Jung, Hee Soo Kim
  • Patent number: 7973207
    Abstract: The present invention is an improved cyclic, endothermic hydrocarbon conversion process and a catalyst bed system for accomplishing the same. Specifically, the improved process comprises reacting a hydrocarbon with a multi-component catalyst bed in such a manner that the temperature within the catalyst bed remains within controlled temperature ranges throughout all stages of the process. The multi-component catalyst bed comprises a reaction-specific catalyst physically mixed with a heat-generating material.
    Type: Grant
    Filed: October 16, 2007
    Date of Patent: July 5, 2011
    Assignee: Sud-Chemie Inc.
    Inventors: Vladimir Fridman, Michael A. Urbancic
  • Publication number: 20100280300
    Abstract: A method of producing a mixed manganese ferrite catalyst, and a method of preparing 1,3-butadiene using the mixed manganese ferrite catalyst. Specifically, a method of producing a mixed manganese ferrite catalyst through a coprecipitation method which is performed at a temperature of 10˜40° C., and a method of preparing 1,3-butadiene using the mixed manganese ferrite catalyst through an oxidative dehydrogenation reaction, in which a C4 mixture containing n-butene, n-butane and other impurities is directly used as reactants without performing additional n-butane separation process or n-butene extraction. 1,3-butadiene can be prepared directly using a C4 mixture including n-butane at a high concentration as a reactant through an oxidative hydrogenation reaction without performing an additional n-butane separation process, and 1,3-butadiene, having high activity, can be also obtained in high yield for a long period of time.
    Type: Application
    Filed: November 7, 2008
    Publication date: November 4, 2010
    Applicant: SK ENERGY CO., LTD
    Inventors: Young Min Chung, Yong Tak Kwon, Tae Jin Kim, Seong Jun Lee, Min Su Ko, Seung Hoon Oh, Yong Seung Kim, In Kyu Song
  • Publication number: 20100121123
    Abstract: The present invention relates to a zinc ferrite catalyst, a method of producing the same, and a method of preparing 1,3-butadiene using the same. Specifically, the present invention relates to a zinc ferrite catalyst which is produced in a pH-adjusted solution using a coprecipitation method, a method of producing the same, and a method of preparing 1,3-butadiene using the same, in which the 1,3-butadiene can be prepared directly using a C4 mixture including n-butene and n-butane through an oxidative dehydrogenation reaction. The present invention is advantageous in that 1,3-butadiene can be obtained at a high yield directly using a C4 fraction without performing an additional process for separating n-butene, as a reactant, from a C4 fraction containing impurities.
    Type: Application
    Filed: May 8, 2008
    Publication date: May 13, 2010
    Inventors: Young Min Chung, Seong Jun Lee, Tae Jin Kim, Seung Hoon Oh, Yong Seung Kim, In Kyu Song, Hee Soo Kim, Ji Chul Jung, Ho Won Lee
  • Patent number: 7683232
    Abstract: A process is disclosed for producing functionalized olefins from a fuel source including an organic compound including a functional group. Useful fuel sources include, for example, biofeedstocks (e.g., carbohydrates, triglycerides, polyols, and biodiesel). The process is preferably carried out by partial oxidation. The overall process can be carried out autothermally.
    Type: Grant
    Filed: May 25, 2005
    Date of Patent: March 23, 2010
    Assignee: Regents of the University of Minnesota
    Inventors: Lanny D. Schmidt, Ramanathan Subramanian
  • Patent number: 7626068
    Abstract: Catalysts and methods for alkane oxydehydrogenation are disclosed. The catalysts of the invention generally comprise (i) nickel or a nickel-containing compound and (ii) at least one or more of titanium (Ti), tantalum (Ta), niobium (Nb), hafnium (Hf), tungsten (W), yttrium (Y), zinc (Zn), zirconium (Zr), or aluminum (Al), or a compound containing one or more of such element(s). In preferred embodiments, the catalyst is a supported catalyst, the alkane is selected from the group consisting of ethane, propane, isobutane, n-butane and ethyl chloride, molecular oxygen is co-fed with the alkane to a reaction zone maintained at a temperature ranging from about 250° C. to about 350° C., and the ethane is oxidatively dehydrogenated to form the corresponding alkene with an alkane conversion of at least about 10% and an alkene selectivity of at least about 70%.
    Type: Grant
    Filed: April 11, 2007
    Date of Patent: December 1, 2009
    Assignee: Celanese International Corporation
    Inventor: Yumin Liu
  • Patent number: 7622623
    Abstract: An improved dehydrogenation catalyst bed system for olefin production utilizing classical processing techniques is disclosed.
    Type: Grant
    Filed: September 2, 2005
    Date of Patent: November 24, 2009
    Assignee: Sud-Chemie Inc.
    Inventors: Vladimir Fridman, Jay S. Merriam, Michael A. Urbancic
  • 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: 7495138
    Abstract: A process for preparing butadiene, comprising nonoxidatively dehydrogenating n-butane from a stream (a) in a first dehydrogenation zone to obtain stream (b) comprising 1-butene, 2-butene, and butadiene; oxidatively dehydrogenating the 1-butene and 2-butene of (b) in the presence of an oxygenous gas in a second dehydrogenation zone to obtain stream (c) comprising n-butane, butadiene, hydrogen, and steam; compressing and cooling (c) to obtain stream (d2) comprising n-butane, butadiene, hydrogen, and steam; extractively distilling (d2) into stream (e1) comprising butadiene and stream (e2) comprising n-butane, hydrogen, and steam; optionally compressing and cooling (e2) to obtain stream (f1) comprising n-butane and water and stream (f2) comprising n-butane and hydrogen and optionally recycling (f1) into the first dehydrogenation zone; separating (f2) into stream (g1) comprising n-butane and stream (g2) comprising hydrogen by contacting (f2) with a high boiling absorbent and subsequently desorbing the gas constitu
    Type: Grant
    Filed: December 19, 2005
    Date of Patent: February 24, 2009
    Assignee: BASF Aktiengesellschaft
    Inventors: Sven Crone, Catharina Klanner, Götz-Peter Schindler, Mark Duda, Frieder Borgmeier
  • Patent number: 7485761
    Abstract: A process for preparing 1-butene, which includes nonoxidatively, catalytically dehydrogenating n-butane to obtain a product gas stream of n-butane, 1-butene, 2-butene, butadiene, hydrogen, and secondary constituents; removing hydrogen and the secondary constituents to obtain a C4 product gas stream; separating the C4 product stream into a recycle stream of n-butane and a stream of 1-butene, 2-butene and butadiene by extractive distillation, and recirculating the recycle stream to the dehydrogenation zone; introducing the 1 -butene, 2-butene and butadiene stream into a selective hydrogenation zone and selective hydrogenation of butadiene to 1-butene and/or 2-butene to obtain a stream of 1-butene and 2-butene; introducing the 1-butene and 2-butene stream, and a circulating stream of 1-butene and 2-butene into a distillation zone and isolation of a product stream; and introducing the 2-butene-containing stream into an isomerization zone to obtain a circulating stream of 1-butene and 2-butene, and recirculating t
    Type: Grant
    Filed: October 27, 2004
    Date of Patent: February 3, 2009
    Assignee: BASF Aktiengesellschaft
    Inventors: Götz-Peter Schindler, Andreas Brodhagen, Thorsten Johann, Thomas Hill, Marcus Sigl, Regina Benfer
  • Patent number: 7435860
    Abstract: A process for preparing butadiene, comprising nonoxidatively dehydrogenating n-butane from a stream (a) in a first dehydrogenation zone to obtain stream (b) comprising 1-butene and 2-butene; oxidatively dehydrogenating the 1-butene and 2-butene of (b) in the presence of an oxygenous gas in a second dehydrogenation zone to obtain stream (c) comprising n-butane, butadiene, hydrogen, carbon dioxide, and steam; compressing and cooling (c) to obtain stream (d2) comprising n-butane, butadiene, hydrogen, carbon dioxide, and steam; extractively distilling (d2) into stream (e1) comprising butadiene and stream (e2) comprising n-butane, hydrogen, carbon dioxide, and steam; compressing and cooling (e2) to obtain stream (f1) comprising n-butane and water and stream (f2) comprising n-butane, hydrogen, and carbon dioxide; cooling (f2) to obtain stream (g1) comprising n-butane and stream (g2) comprising carbon dioxide and hydrogen; phase separating water from (f1) to obtain stream (h1) comprising n-butane; and recycling (h1)
    Type: Grant
    Filed: December 7, 2005
    Date of Patent: October 14, 2008
    Assignee: BASF SE
    Inventors: Sven Crone, Catharina Klanner, Götz-Peter Schindler, Mark Duda, Frieder Borgmeier
  • Patent number: 7417173
    Abstract: Processes for producing butadiene from n-butane comprising: (a) providing a feed gas stream comprising n-butane; (b) non-oxidatively dehydrogenating the feed gas stream in the presence of a catalyst in a first dehydrogenation zone to form a first intermediate gas stream comprising n-butane, 1-butene, 2-butene, butadiene and hydrogen; (c) oxidatively dehydrogenating the first intermediate gas stream in the presence of an oxygenous gas having an oxygen content of at least 75% by volume in a second dehydrogenation zone to form a second intermediate gas stream comprising n-butane, butadiene, hydrogen, carbon dioxide and steam; (d) compressing and cooling the second intermediate gas to form a first condensate stream comprising water and a third intermediate gas stream comprising n-butane, butadiene, hydrogen, carbon dioxide and steam; (e) compressing and cooling the third intermediate gas to form a second condensate stream comprising n-butane, butadiene and water and a fourth intermediate gas stream comprising n-b
    Type: Grant
    Filed: November 11, 2005
    Date of Patent: August 26, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Sven Crone, Catharina Klanner, Götz-Peter Schindler, Mark Duda, Frieder Borgmeier
  • Patent number: 7262334
    Abstract: A process for the production of a reaction product including a carbon containing compound. The process includes providing a film of a fuel source including at least one organic compound on a wall of a reactor, contacting the fuel source with a source of oxygen, forming a vaporized mixture of fuel and oxygen, and contacting the vaporized mixture of fuel and oxygen with a catalyst under conditions effective to produce a reaction product including a carbon containing compound. Preferred products include ?-olefins and synthesis gas. A preferred catalyst is a supported metal catalyst, preferably including rhodium, platinum, and mixtures thereof.
    Type: Grant
    Filed: July 15, 2003
    Date of Patent: August 28, 2007
    Assignee: Regents of the University of Minnesota
    Inventors: Lanny D. Schmidt, Jakob J. Krummenacher, Kevin N. West
  • Patent number: 7045671
    Abstract: A process for catalytic dehydrogenation of a dehydrogenatable hydrocarbon process stream to the corresponding olefin or olefins, the process comprising contacting the dehydrogenatable hydrocarbon process stream under dehydrogenation conditions with a mesoporous zeotype catalyst having an intra-crystalline, non-crystallographic mesopore system and a mesopore volume of the zeotype crystals above 0.25 ml/g and comprising at least one element belonging to Groups 5–14 in the Periodic Table of the Elements (new notation). The invention also comprises a catalyst for use in the above process.
    Type: Grant
    Filed: November 21, 2003
    Date of Patent: May 16, 2006
    Assignee: Haldor Topsoe A/S
    Inventors: Iver Schmidt, Anne Krogh, Claus Hviid Christensen
  • Publication number: 20040116760
    Abstract: A gel composition substantially contained within the pores of a solid material is disclosed for use as a catalyst or as a catalyst support in dehydrogenation and dehydrocyclization processes.
    Type: Application
    Filed: November 21, 2003
    Publication date: June 17, 2004
    Inventors: Kostantinos Kourtakis, Leo Ernest Manzer
  • Patent number: 6600082
    Abstract: A process for dehydrogenating organic compounds, in particular paraffins and naphthenes, is carried out in the presence of a supported catalyst comprising a group VIII metal such as platinum, and tin, at least a portion of which interacts strongly with the group VIII metal in the catalyst in the reduced state. In the partially oxidised state, the catalyst contains at least 10% of tin in the form of a reduced tin species with oxidation state 0, said species having an isomer shift in the range 0.80 to 2.60 mm/s and a quadrupolar splitting in the range 0.65 to 2.00 mm/s.
    Type: Grant
    Filed: August 23, 2001
    Date of Patent: July 29, 2003
    Assignee: Institut Francais du Petrole
    Inventors: Fabienne Le Peltier, Blaise Didillon, Jean-Claude Jumas, Josette Olivier-Fourcade
  • Publication number: 20030105373
    Abstract: This invention relates to a dehydrogenation process using a layered catalyst composition. The catalyst composition comprises an inner core such as alpha-alumina, and an outer layer bonded to the inner core composed of an outer refractory inorganic oxide such as gamma-alumina. The outer layer has uniformly dispersed thereon a platinum group metal such as platinum and a promoter metal such as tin. The composition also contains a modifier metal such as lithium. The catalyst composition shows improved durability and selectivity for dehydrogenating hydrocarbons, especially at dehydrogenation conditions comprising a low water concentration.
    Type: Application
    Filed: October 25, 2002
    Publication date: June 5, 2003
    Inventors: Dean E. Rende, Andrew W. Broerman, Andrea G. Bozzano, R. Joe Lawson, Karl Z. Steigleder, Masao Takayama
  • Publication number: 20030040655
    Abstract: A catalyst useful for the production of olefins from alkanes via oxidative dehydrogenation (ODH) is disclosed. The catalyst includes an oxide selected from the group containing alumina, zirconia, titania, yttria, silica, niobia, and vanadia. The catalyst does not contain any unoxidized metals; it is activated by higher preheat temperatures. As a result, similar conversions are achieved at a considerably lower cost.
    Type: Application
    Filed: March 26, 2002
    Publication date: February 27, 2003
    Applicant: Conoco Inc.
    Inventors: Lisa M. Budin, Larry M. Meyer
  • Publication number: 20020004623
    Abstract: A hydrocarbon conversion process in which the rate of coke formation is reduced and aromatics and light olefins yield is increased by the use of an improved zeolite catalyst that comprises a silylated, zeolite material preferably treated with steam. Another embodiment includes the use of an improved zeolite catalyst that comprises silylated, acid treated zeolite material.
    Type: Application
    Filed: July 8, 1999
    Publication date: January 10, 2002
    Inventors: CHARLES A. DRAKE, AN-HSIANG WU
  • Patent number: 6187985
    Abstract: A process for dehydrogenating C5-C22 aliphatic hydrocarbons to the corresponding olefinic hydrocarbons is carried out in the presence of a catalyst comprising at least one support, at least one metal from group VIII of the periodic table and at least one additional element M selected from the group formed by germanium, tin, lead, rhenium, gallium, indium, and thallium. The process is characterized in that the catalyst is prepared using a process in which said metal M is introduced in an aqueous solvent in the form of at least one organometallic compound comprising at least one carbon-M bond.
    Type: Grant
    Filed: October 30, 1998
    Date of Patent: February 13, 2001
    Assignee: Institut Francais du Petrole
    Inventors: Fabienne Le Peltier, Blaise Didillon, Olivier Clause
  • Patent number: 5962757
    Abstract: Dehydrogenation catalysts are prepared by a predoping process comprising, mixing iron oxide materials with a predopant to form a blend of iron oxide and predopant and heating the blend to the predoping conditions and thereafter forming a catalyst. The catalysts so prepared are useful in the dehydrogenation of a composition having at least one carbon--carbon double bond. Such catalytic uses include the conversion of ethylbenzene to styrene.
    Type: Grant
    Filed: April 17, 1997
    Date of Patent: October 5, 1999
    Assignee: Shell Oil Company
    Inventors: Stanley Nemec Milam, Brent Howard Shanks
  • Patent number: 5929298
    Abstract: This invention provides a process for preparing conjugated dienes using certain substituted rhenium compounds as catalysts. The substituted rhenium compounds have the formula R.sub.5 ReO.sub.3, wherein R.sub.5 is selected from the group consisting of C.sub.1 -C.sub.10 alkyl, aryl, aryl-C.sub.1 -C.sub.10 alkyl, cyclopentadienyl and cyclopentadienyl substituted with one to four C.sub.1 -C.sub.4 alkyl groups. The process of the invention thus provides a facile method for preparing conjugated dienes using the corresponding tertiary vinyl alcohol as starting material. Examples of such starting materials includes phytols, manool, 5-vinyl-5-nonanol, 1-vinyl4-tert-butylcyclohexanol, and 1-vinylcyclooctanol. The process can be carried out neat as well as in an inert solvent in the gas or solution phase.
    Type: Grant
    Filed: July 13, 1998
    Date of Patent: July 27, 1999
    Assignee: Eastman Chemical Company
    Inventor: John Anthony Hyatt
  • Patent number: 5877377
    Abstract: A method for conducting a chemical reaction with a catalyst composed of metal oxide particles among which are uniformly incorporated, in order to reduce the operating temperature of the catalyst, palladium particles.
    Type: Grant
    Filed: October 20, 1995
    Date of Patent: March 2, 1999
    Assignee: Johnson Matthey Public Limited Company
    Inventors: Stanislaw E. Golunski, John M. Gascoyne, Anthony Fulford, John W. Jenkins
  • Patent number: 5639926
    Abstract: A process for producing a branched chain olefin which comprises isomerising and transhydrogenating a hydrocarbon stream containing at least one straight chain paraffin of 4 or more carbon atoms by contacting the same at elevated temperature with a stream containing a hydrogen acceptor that is more highly unsaturated than a mono-olefin to produce a stream containing at least one branched chain olefin product. The product is separated to give a stream depleted of the product. The thus depleted stream is recycled to the isomerising and transhydrogenating stages. The hydrogen acceptor stream may comprise a diene and/or acetylene.
    Type: Grant
    Filed: January 4, 1995
    Date of Patent: June 17, 1997
    Assignee: Institut Francais Du Petrole
    Inventors: Stephen Keith Turner, Arthur Gough
  • Patent number: 5585530
    Abstract: A process for the production of olefins comprises dehydrogenating at least one hydrogen-donor hydrocarbon that is essentially free from olefinic unsaturation, e.g. a paraffin, in the presence of a dehydrogenation catalyst and in the presence of at least one hydrogen-acceptor hydrocarbon that is more highly unsaturated than a mono-olefin, e.g. a diene and/or acetylene, under conditions effective to cause at least part of said hydrogen-donor hydrocarbon to be dehydrogenated and at least part of the hydrogen-acceptor to be hydrogenated. The amount of hydrogen-acceptor is such that there are 0.5 to 20 moles of said hydrogen-donor for each mole of hydrogen-acceptor. Preferably the amount of said hydrogen-acceptor hydrocarbon hydrogenated is such that the heat of hydrogenation of said hydrogen-acceptor hydrocarbon provides at least 25% of the heat required for dehydrogenation of said hydrogen-donor hydrocarbon. In a preferred form of the invention, a hydrocarbon stream containing a hydrogen-acceptor is a C.sub.
    Type: Grant
    Filed: June 8, 1994
    Date of Patent: December 17, 1996
    Assignee: Institut Francais Du Petrole
    Inventors: Arthur Gough, Stephen K. Turner
  • Patent number: 5545787
    Abstract: A continuous process for the dehydrogenation of a hydrocarbon and/or oxygenated hydrocarbon feed, comprising contacting the hydrocarbon and/or oxygenated hydrocarbon feed with a dehydrogenation catalyst at elevated temperature in a reaction zone characterized in that the catalyst is capable of retaining hydrogen and (a) is contacted with a feed to form a dehydrogenated product and hydrogen, at least some of the hydrogen formed being adsorbed by the catalyst and/or reacting therewith to reduce at least part of the catalyst; (b) the dehydrogenated product and any unadsorbed/unreacted hydrogen is removed from the reaction zone; (c) at least some of the adsorbed hydrogen is removed from the catalyst and/or at least some of the reduced catalyst is oxidized; and (d) reusing the catalyst from step (c) in step (a).
    Type: Grant
    Filed: May 31, 1994
    Date of Patent: August 13, 1996
    Assignee: BP Chemicals Limited
    Inventors: Jeremy B. Cooper, Jonathon C. Frost, Stephen R. Partington
  • Patent number: 5476982
    Abstract: The present invention is directed to a novel catalyst composition and its use in the dehydrogenation of paraffins to olefins. The catalyst comprises an alloy of a Group VIII noble metal and a metal selected from the group consisting of zinc and gallium on a support selected from the group consisting of silica, zinc oxide modified silica and zinc oxide modified silica-pillared clays when said alloy is a zinc alloy, and silica, gallium oxide modified silica and gallium oxide modified silica-pillared clays when said alloy is a gallium alloy. The instant catalyst is an active and selective catalyst for the catalytic dehydrogenation of paraffins to olefins, especially gaseous paraffins, having the added benefit of retaining high activity and selectivity even following repeated regeneration by calcination in oxygen containing gas at temperatures of 450.degree. C. to 650.degree. C., preferably 450.degree. C. to 500.degree. C.
    Type: Grant
    Filed: June 14, 1994
    Date of Patent: December 19, 1995
    Assignee: Exxon Research & Engineering Co.
    Inventors: John L. Robbins, Elise Marucchi-Soos, Jack W. Johnson, John F. Brody
  • Patent number: 5449450
    Abstract: Hydrocarbon conversion processes are described which use novel microporous compositions. These compositions have a three-dimensional microporous framework structure of ZnO.sub.2, PO.sub.2 and M'O.sub.2 tetrahedral units, and an intracrystalline pore system. The M' metal is selected from the group consisting of magnesium, copper, gallium, aluminum, germanium, cobalt, chromium, iron, manganese, titanium and mixtures thereof. Examples of the hydrocarbon conversion processes include hydrocracking, hydrotreating and hydrogenation.
    Type: Grant
    Filed: December 15, 1993
    Date of Patent: September 12, 1995
    Assignee: UOP
    Inventor: Robert L. Bedard
  • Patent number: 5386074
    Abstract: Barium peroxide in which has been incorporated a transition metal compound is used as a catalyst for the oxidative dehydrogenation of organic compounds in the presence of terminal oxidants.
    Type: Grant
    Filed: July 30, 1993
    Date of Patent: January 31, 1995
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Vincent A. Durante, James E. Lyons, Darrell W. Walker
  • Patent number: 5245109
    Abstract: A contact material composition of an intimately mixed halogencontaining mixed oxide of at least one cationic species of a naturally occurring Group IIIB element, at least one cationic species of a Group IIA metal of magnesium, calcium, strontium and barium and at least one cationic species of germanium and gallium, as well as methods for hydrocarbon conversion using such contact material compositions are provided.
    Type: Grant
    Filed: October 11, 1991
    Date of Patent: September 14, 1993
    Assignee: Amoco Corporation
    Inventors: Mark P. Kaminsky, Mark S. Kleefisch, George A. Huff, Jr., Don M. Washecheck, Mark K. Barr
  • Patent number: 5053580
    Abstract: Metal oxide powders comprised of Cr(III) oxide, Ti(IV) oxide, V(V) oxide, or mixtures of these, or metal mixed oxides comprised of Cr(III) oxide and Ti(IV) oxide and V(V) oxide, or their mixtures. They have BET surfaces of 5-50m.sup.2 /g and mean particle diameters of 25-350 nm and are useful to increase conversion and selectivity in the manufacture of mono-olefins by catalytic dehydrogenation of saturated hydrocarbons. The metal oxide powders are produced from mixtures of the vaporized metal compounds chromyl chloride, titanium tetrachloride, and vanadyl chloride, in the presence of certain gases by laser pyrolysis.
    Type: Grant
    Filed: May 7, 1990
    Date of Patent: October 1, 1991
    Assignee: Veba Oel Aktiengesellschaft
    Inventors: Bernhard Schramm, Jurgen Kern, Harald Schwahn, August-Wilhelm Preuss, Klaus Gottlieb, Hartmut Bruderreck
  • Patent number: 4973779
    Abstract: A hydrocarbon conversion process which utilizes a novel catalytic composite is disclosed. The catalyst composite comprises a platinum group metal component, a first modifier selected from Group IA and IIA elements of the Periodic Table, a second modifier component selected from the group of elements consisting of palladium, iridium, and osmium, and a third modifier component selected from the elements of Group IVA of the Periodic Table of the Elements. All of the catalytic components are located on a refractory oxide support having a nominal diameter (d) of from 50 to 10,000 microns. The catalytic composite is characterized in that the second modifier components is surface-impregnated upon the support in such a manner that the average concentration of the surface-impregnated second modifier component on the outside 0.2d micron catalyst layer is at least 2 times the average concentration of the second modifier component in 0.
    Type: Grant
    Filed: November 9, 1989
    Date of Patent: November 27, 1990
    Assignee: UOP
    Inventors: Tamotsu Imai, Hayim Abrevaya
  • Patent number: 4922050
    Abstract: A catalytic dehydrogenation to produce the unsaturated analogs of aliphatic compounds with high process selectivity for the unsaturated analog production. The catalytic dehydrogenation comprises contacting the aliphatic compound, under dehydrogenation conditions, with a catalyst composition comprising a dehydrogenation metal and indium containing non-acidic crystalline microporous material.
    Type: Grant
    Filed: May 18, 1989
    Date of Patent: May 1, 1990
    Assignee: Mobil Oil Corporation
    Inventors: Ralph M. Dessau, Randall D. Partridge, Ernest W. Valyocsik
  • Patent number: 4914249
    Abstract: Dehydrogenatable hydrocarbons may be subjected to a dehydrogenation reaction in which the hydrocarbons such as ethylbenzene are contacted with a dehydrogenation catalyst comprising a modified iron compound in the presence of steam. The reaction mixture effluent containing unconverted hydrocarbons, dehydrogenatable hydrocarbon, hydrogen and steam is then contacted with an oxidation catalyst in a second oxidation zone whereby hydrogen is selectively oxidized to the substantial exclusion of oxidation of the hydrocarbon. The selective oxidation catalyst which is employed is prepared in a two-step process in which a compound containing a noble metal of Group VIII of the Periodic Table and a compound containing a metal of Group IVA of the Periodic Table is impregnated on a porous inorganic support such as alumina. The impregnated support is then calcined and subjected to a second step impregnation in which the support is impregnated with a solution of a compound containing lithium.
    Type: Grant
    Filed: December 29, 1988
    Date of Patent: April 3, 1990
    Assignee: UOP
    Inventor: Bryan L. Benedict
  • Patent number: 4902845
    Abstract: Catalyst activity life of an iron oxide-containing catalyst is extended by contacting such catalyst with a feedstream containing about 0.0001 to about 0.01 mole of oxygen per mole of feed in the substantial absence of an oxidation catalyst.
    Type: Grant
    Filed: November 21, 1988
    Date of Patent: February 20, 1990
    Assignee: Amoco Corporation
    Inventors: Dae K. Kim, George A. McConaghy
  • Patent number: 4895994
    Abstract: Catalysts made by the Raney process (e.g., Raney process nickel) pelletized in matrix of polymer and plasticizer are activated by either (a) removal of plasticizer (e.g., by solvent extraction) followed by leaching out Al with caustic solution, leaving an active catalyst made by the Raney process in a polymer matrix; or (b) removal of plasticizer, then calcining to remove polymer, followed by leaching with caustic. The activated catalyst pellets have sufficient strength and attrition resistance for efficient use in fixed beds and packed columns for superior hydrogenation of toluene, heptene, butyraldehyde, and other conventional feedstockers used with catalysts made by the Raney process.
    Type: Grant
    Filed: October 18, 1988
    Date of Patent: January 23, 1990
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Wu-Cheng Cheng, Christian B. Lundsager, Robert M. Spotnitz
  • Patent number: 4886926
    Abstract: A catalytic dehydrogenation to produce the unsaturated analogs of aliphatic compounds with high process selectivity for the unsaturated analog production. The catalytic dehydrogenation comprises contacting the aliphatic compound, under dehydrogenation conditions, with a catalyst composition comprising a dehydrogenation metal and tin containing non-acidic crystalline microporous material.
    Type: Grant
    Filed: June 24, 1988
    Date of Patent: December 12, 1989
    Assignee: Mobil Oil Corporation
    Inventors: Ralph M. Dessau, Ernest W. Valyocsik, James C. Vartuli
  • Patent number: 4874504
    Abstract: A method is disclosed which provides improved control over the noble-metal exchange of zeolite catalyst by using bulky organic bases to control pH during the metal loading step.
    Type: Grant
    Filed: March 20, 1989
    Date of Patent: October 17, 1989
    Assignee: Mobil Oil Corporation
    Inventors: Roland von Ballmoos, Francis X. Ryan
  • Patent number: 4849567
    Abstract: A catalytic dehydrogenation to produce the unsaturated analogs of aliphatic compounds with high process selectivity for the unsaturated analog production. The catalytic dehydrogenation comprises contacting the aliphatic compound, under dehydrogenation conditions, with a catalyst composition comprising a dehydrogenation metal and indium containing non-acidic crystalline microporous material.
    Type: Grant
    Filed: December 28, 1987
    Date of Patent: July 18, 1989
    Assignee: Mobil Oil Corporation
    Inventors: Ralph M. Dessau, Randall D. Partridge, Ernest W. Valyocsik