Using Acceptor, E.g., Hydrogen-exchange Disproportionation, Etc. Patents (Class 585/656)
  • Patent number: 11517885
    Abstract: The present invention relates to a catalyst for producing olefins from dehydrogenation of alkane having 2 to 5 carbon atoms and a method for producing olefins using said catalyst, wherein said catalyst comprises a hierarchical zeolite nanosheet having a silica to alumina (SiO2/AI2O3) ratio more than 120 and group X metal(s) in a range of 0.3 to 5% by weight. The catalyst according to the conversion of precursor to yields and high olefins selectivity.
    Type: Grant
    Filed: November 2, 2018
    Date of Patent: December 6, 2022
    Assignee: PTT Global Chemical Public Company Limited
    Inventors: Chularat Wattanakit, Thittaya Yutthalekha, Anawat Thivasasith, Wannaruedee Wannapakdee, Pannida Dugkhuntod, Duangkamon Suttipat
  • Publication number: 20150112109
    Abstract: A layered multimetallic mixed oxide (LMMO) is characterized by one or more diffraction peaks at 5<2?<15, preferably between 10<2?<15. The catalysts can be represented by the general formula: M1 M2 M3 O? wherein M1 is selected from the group of Ag, Au, Zn, Sn, Rh, Pd, Pt, Cu, Ni, Fe, Co, an alkaline metal, an alkaline earth metal, a rare earth metal, or mixtures thereof. M2 is selected from the group of Ti, Hf, Zr, Sn, Bi, Sb, V, Nb, Ta and P, or mixtures thereof. M3 is selected from the group of Mo, W and Cr, or mixtures thereof. ? depends on the amount and oxidation state or valence of the other components, also it depends on the starting materials, preparation method and the activation process, and where the catalyst exhibits at least one X-ray diffraction peak between 5<2?<15.
    Type: Application
    Filed: December 23, 2014
    Publication date: April 23, 2015
    Inventors: Jaime SANCHEZ VALENTE, Enelio TORRES GARCIA, Hector ARMENDARIZ HERRERA, Maria de Lourdes Alejandra GUZMAN CASTILLO, Andrea RODRIGUEZ HERNANDEZ, Roberto QUINTANA SOLORZANO, Maiby VALLE ORTA, Jose Manuel LOPEZ NIETO
  • Patent number: 8969644
    Abstract: A method is proposed for providing an oxygen-containing gas stream for the endothermic reaction of an initial stream comprising one or more hydrocarbons, having a predetermined oxygen concentration and a predetermined temperature, wherein a fluid fuel stream is combusted with a primary air stream at ? values of the primary air stream to the fluid fuel stream of from 0.6 to 1.2 to obtain a combustion gas stream, and a secondary air stream is admixed to the combustion gas stream to obtain the oxygen-containing gas stream for the endothermic reaction, with the predetermined oxygen concentration and the predetermined temperature of the oxygen-containing gas stream being adjusted via the flow rate and the temperature of the secondary air stream.
    Type: Grant
    Filed: January 31, 2008
    Date of Patent: March 3, 2015
    Assignee: BASF SE
    Inventors: Gerhard Olbert, Franz Corr, Sven Crone
  • Patent number: 8912381
    Abstract: A method for the oxidative coupling of hydrocarbons, such as the oxidative coupling of methane, includes providing an oxidative catalyst inside a reactor, and carrying out the oxidative coupling reaction under a set of reaction conditions. The oxidative catalyst includes (A) at least one element selected from the group consisting of the Lanthanoid group, Mg, Ca, and the elements of Group 4 of the periodic table (Ti, Zr, and Hf); (B) at least one element selected from the group consisting of the Group 1 elements of Li, Na, K, Rb, Cs, and the elements of Group 3 (including La and Ac) and Groups 5-15 of the periodic table; (C) at least one element selected from the group consisting of the Group 1 elements of Li, Na, K, Rb, Cs, and the elements Ca, Sr, and Ba; and (D) oxygen.
    Type: Grant
    Filed: June 29, 2009
    Date of Patent: December 16, 2014
    Assignee: Fina Technology, Inc.
    Inventors: Sivadinarayana Chinta, Joseph Thorman, James Butler, Joe Hunter, Taylor Rives
  • Patent number: 8642826
    Abstract: A process for long-term operation of a continuous heterogeneously catalyzed partial dehydrogenation of a hydrocarbon to be dehydrogenated, in which a reaction gas mixture stream comprising the hydrocarbon to be dehydrogenated in a molar starting amount KW is conducted through an overall catalyst bed comprising the total amount M of dehydrogenation catalyst and the deactivation of the overall catalyst bed is counteracted in such a way that, with increasing operating time, the contribution to the conversion in the first third of the total amount M of dehydrogenation catalyst in flow direction decreases, the contribution to the conversion in the last third of the total amount M of dehydrogenation catalyst in flow direction increases, and the contribution to the conversion in the second third of the total amount M of dehydrogenation catalyst in flow direction passes through a maximum.
    Type: Grant
    Filed: July 27, 2007
    Date of Patent: February 4, 2014
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Dieterle, Catharina Klanner, Götz-Peter Schindler, Klaus Joachim Müller-Engel, Jens Scheidel, Christoph Adami
  • Patent number: 8524963
    Abstract: Solid supported organoiridium catalysts, a process for preparing such solid supported organoiridium catalysts, and the use of such solid supported organoiridium catalysts in dehydrogenation reactions of alkanes is provided. The catalysts can be easily recovered and recycled.
    Type: Grant
    Filed: March 27, 2008
    Date of Patent: September 3, 2013
    Assignee: Los Alamos National Security, LLC
    Inventors: R. Thomas Baker, Alfred P. Sattelberger, Hongbo Li
  • Patent number: 8378163
    Abstract: The invention describes catalysts, methods of making catalysts, methods of making a microchannel reactor, and methods of conducting chemical reactions. It has been discovered that superior performance can be obtained from a catalyst formed by directly depositing a catalytic material onto a (low surface area) thermally-grown alumina layer. Improved methods of conducting oxidative dehydrogenations are also described.
    Type: Grant
    Filed: March 23, 2005
    Date of Patent: February 19, 2013
    Assignee: Velocys Corp.
    Inventors: Junko Ida, Francis P. Daly, Terry Mazanec, Barry L. Yang, Richard Long
  • Patent number: 8362312
    Abstract: A method of converting at least one first alkane to a mixture of at least one low molecular weight alkane (optionally also including additional lower and/or higher molecular weight alkanes) and at least one high molecular weight alkane, comprises: reacting a first alkane in the presence of dual catalyst system comprising a first catalyst (i.e., a hydrogen transfer catalyst) and a second catalyst (i.e., a metathesis catalyst) to produce a mixture of low and high molecular weight alkanes.
    Type: Grant
    Filed: June 4, 2008
    Date of Patent: January 29, 2013
    Assignee: The University of North Carolina at Chapel Hill
    Inventors: Maurice Brookhart, Alan Goldman, Emily Carson, Zheng Huang, Sabuj Kumar Kundu
  • Patent number: 8237000
    Abstract: Processes for using a combination of carbon dioxide and oxygen in the dehydrogenation of hydrocarbons are provided. A hydrocarbon feedstock, carbon dioxide and oxygen are fed to an oxidative dehydrogenation reactor system containing one or more catalysts that promote dehydrogenation of the hydrocarbon feedstock to produce a dehydrogenated hydrocarbon product. The processes of the present invention may be used, for example, to produce styrene monomer by dehydrogenation of ethylbenzene using carbon dioxide and oxygen as oxidants.
    Type: Grant
    Filed: June 19, 2008
    Date of Patent: August 7, 2012
    Assignee: Lummus Technology, Inc.
    Inventors: Stephen C. Arnold, Johannes Hendrik Koegler, Anne Mae Gaffney, Chuen Yuan Yeh, Ruozhi Song
  • Patent number: 8043577
    Abstract: With the help of a method and device for nozzle-jetting oxygen into a synthesis reactor, e.g. for oxy-dehydration, with largely axial flow of the gas mixture through a catalyst bed, it is intended to vastly improve the mixing-in and mixing-through of oxygen above the catalyst especially for oxy-dehydration process. This is achieved by feeding the oxygen to a ring distributor system arranged above the catalyst bed in pure form, as air or mixed with inert gas or water vapor and jetting the oxygen onto the catalyst surface through several exit openings in the ring distributor at an inclined angle deviating from the vertical.
    Type: Grant
    Filed: December 10, 2004
    Date of Patent: October 25, 2011
    Assignee: Uhde GmbH
    Inventors: Johannes Kowoll, Max Heinritz-Adrian, Lothar Semrau
  • Patent number: 8013196
    Abstract: The invention relates to a process for the production of ethylene, comprising the steps of a) thermally converting, by a pyrolysis or a partial oxidation process, a feed charge containing methane into an acetylene containing effluent, and b) in situ hydrogenating, by a non-catalytic reaction, the acetylene produced in the first step into ethylene by intimately mixing the acetylene containing effluent with an ethane feed. The process according to the invention is more efficient than other synthesis schemes, while simplifying the overall process design. This process thus offers an economically attractive scheme for mass production of ethylene from natural gas, based on a well-known and proven acetylene route.
    Type: Grant
    Filed: June 22, 2006
    Date of Patent: September 6, 2011
    Assignee: Saudi Basic Industries Corporation
    Inventors: Aggadin Mamedov, Saeed Al-Wahabi, Yungyi Lin, Mohamed Sabri Abdelghani, Akram Al-Alwan
  • Patent number: 7999144
    Abstract: Methods of oxidative dehydrogenation are described. Surprisingly, Pd and Au alloys of Pt have been discovered to be superior for oxidative dehydrogenation in microchannels. Methods of forming these catalysts via an electroless plating methodology are also described. An apparatus design that minimizes heat transfer to the apparatus' exterior is also described.
    Type: Grant
    Filed: September 1, 2006
    Date of Patent: August 16, 2011
    Assignee: Velocys
    Inventors: Anna Lee Tonkovich, Bin Yang, Steven T. Perry, Terry Mazanec, Ravi Arora, Francis P. Daly, Richard Long, Thomas D. Yuschak, Paul W. Neagle, Amanda Glass
  • Patent number: 7923592
    Abstract: The disclosed invention relates to a process for converting a feed composition comprising one or more hydrocarbons to a product comprising one or more unsaturated hydrocarbons, the process comprising: flowing the feed composition and steam in contact with each other in a microchannel reactor at a temperature in the range from about 200° C. to about 1200° C. to convert the feed composition to the product, the process being characterized by the absence of catalyst for converting the one or more hydrocarbons to one or more unsaturated hydrocarbons. Hydrogen and/or oxygen may be combined with the feed composition and steam.
    Type: Grant
    Filed: February 2, 2007
    Date of Patent: April 12, 2011
    Assignee: Velocys, Inc.
    Inventors: Anna Lee Tonkovich, Thomas Yuschak, Timothy J. LaPlante, Scott Rankin, Steven T. Perry, Sean Patrick Fitzgerald, Wayne W. Simmons, Terry Mazanec, Eric Daymo
  • Patent number: 7906699
    Abstract: A method for producing a mixture of ethylene and carbon monoxide by contacting ethane and an oxygen source at a temperature of at least 500° C. to produce ethylene and carbon monoxide. A method for producing an alkyl propionate by steps of: (a) contacting ethane and an oxygen source at a temperature of at least 500° C. to produce ethylene; (b) contacting an alcohol, ethylene and carbon monoxide with an ethylene carbonylation catalyst to produce the alkyl propionate; and (c) separating the alkyl propionate from byproducts and starting materials. The method further comprises condensing the alkyl propionate with formaldehyde to produce an alkyl methacrylate.
    Type: Grant
    Filed: August 5, 2008
    Date of Patent: March 15, 2011
    Assignee: Rohm and Haas Company
    Inventors: Abraham Benderly, Scott Han, Mark Anthony Silvano, Donald Lee Zolotorofe
  • Patent number: 7902417
    Abstract: A method of converting at least one first alkane to a mixture of at least one low molecular weight alkane (optionally also including additional lower and/or higher molecular weight alkanes) and at least one high molecular weight alkane, comprising: reacting a first alkane in the presence of dual catalyst system comprising a first catalyst (i.e., a hydrogen transfer catalyst and preferably an iridium pincer complex catalyst) and a second catalyst (i.e., a metathesis catalyst) to produce a mixture of low and high molecular weight alkanes.
    Type: Grant
    Filed: July 7, 2006
    Date of Patent: March 8, 2011
    Assignees: The University of North Carolina at Chapel Hill, Rutgers, The State University of New Jersey
    Inventors: Alan S. Goldman, Maurice Brookhart, Amy H. Roy, Ritu Ahuja, Zheng Huang
  • Patent number: 7816572
    Abstract: A process for producing propylene and isoprene from a feed stream comprising 1-butene and isobutene is disclosed. The feed stream is reacted in a catalytic distillation reactor containing an olefin isomerization catalyst to produce an overhead stream comprising 2-butene and isobutene and a bottoms stream comprising 2-butene. The overhead stream is reacted in the presence of a metathesis catalyst to produce propylene and isoamylenes. Isoprene is produced by dehydrogenation of isoamylenes.
    Type: Grant
    Filed: August 7, 2007
    Date of Patent: October 19, 2010
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: David W. Leyshon, Thomas S. Zak
  • Publication number: 20100191031
    Abstract: Processes for production of olefins from hydrocarbon feedstocks are provided. In one aspect, the processes of the present invention utilize coils passing through a pyrolysis furnace to partially convert a hydrocarbon feedstock to olefins, followed by further conversion of the hydrocarbon feedstock in an adiabatic reactor. A portion of the coils in the pyrolysis furnace carry the hydrocarbon feedstock and the remainder carry steam only. After a selected period of time, the material flowing through the coils is switched. By flowing steam through the coils that had previously contained the hydrocarbon feedstock, on-line decoking can occur. In another aspect, a high temperature reactor is used to convert methane or natural gas to olefins.
    Type: Application
    Filed: January 26, 2009
    Publication date: July 29, 2010
    Inventor: Kandasamy Meenakshi Sundaram
  • Publication number: 20080249343
    Abstract: Solid supported organoiridium catalysts, a process for preparing such solid supported organoiridium catalysts, and the use of such solid supported organoiridium catalysts in dehydrogenation reactions of alkanes is provided. The catalysts can be easily recovered and recycled.
    Type: Application
    Filed: March 27, 2008
    Publication date: October 9, 2008
    Inventors: R. Thomas Baker, Alfred P. Sattelberger, Hongbo Li
  • Patent number: 6831204
    Abstract: A new family of oxidative dehydrogenation catalysts having MCrAlY supports can be used in the production of olefins. Olefins are produced by heating a feed stream comprising at least an alkane and an oxidant to a temperature between 25° C. and 800° C.; contacting the feed stream with a catalyst comprising an MCrAlY structure and, optionally, a Group VIII promoter metal coating, wherein M is a base metal, or combination of base metals; and maintaining a contact time of the alkane with the catalyst of less than 200 milliseconds under conditions sufficient to achieve oxidative dehydrogenation of the alkane. M may comprise a metal selected from the group consisting of Group IB-VIIB metals, Group IIIA-VA metals, lanthanide metals, iron, cobalt, nickel, and combinations thereof. More particularly, M may comprise a metal selected from the group consisting Tb, Sm, Pr, Fe, Ni, Co, and combinations thereof.
    Type: Grant
    Filed: October 11, 2002
    Date of Patent: December 14, 2004
    Assignee: ConocoPhillips Company
    Inventors: Zhen Chen, Sriram Ramani, Lisa M. Carmichael, Joe D. Allison
  • Patent number: 6624116
    Abstract: An on-line method of synthesizing or regenerating catalysts for autothermal oxidation processes, specifically, the oxidation of paraffinic hydrocarbons, for example, ethane, propane, and naphtha, to olefins, for example, ethylene and propylene. The catalyst comprises a Group 8B metal, for example, a platinum group metal and, optionally, a promoter, such as tin, antimony, or copper, on a support, preferably a monolith support. On-line synthesis or regeneration involves co-feeding a volatile Group 8B metal compound and/or a volatile promoter compound with the paraffinic hydrocarbon and oxygen into the oxidation reactor under ignition or autothermal conditions.
    Type: Grant
    Filed: November 3, 2000
    Date of Patent: September 23, 2003
    Assignee: Dow Global Technologies Inc.
    Inventors: Sameer S. Bharadwaj, Joseph J. Maj, Jonathan H. Siddall
  • Patent number: 6566569
    Abstract: A process for preparing a C4- product stream and a C6+ product stream is disclosed. The process involves contacting a C5 containing paraffinic feedstock with a catalyst that includes a hydrogenation/dehydrogenation catalyst and an olefin metathesis catalyst under conditions which dehydrogenate the paraffins to olefins. The olefins are then metathesized and rehydrogenated to provide a product stream. A C4- fraction and a C6+ fraction can each be isolated from the product stream. The C4- fraction can be used, for example, in an alkylation reaction to provide compounds useful in gasoline compositions. Unconverted C5 paraffins can be recycled. The C6+ fraction can be used, for example, as solvents. Alternatively, they can be isomerized to form gasoline additives, or can be converted to aromatic compounds via reforming, for example, using conventional reforming techniques, preferably using the AROMAX™ process or traditional rheniforming conditions.
    Type: Grant
    Filed: June 23, 2000
    Date of Patent: May 20, 2003
    Assignee: Chevron U.S.A. Inc.
    Inventors: Cong-Yan Chen, Dennis J. O'Rear, Scott R. Brundage
  • Patent number: 6566573
    Abstract: A process and catalyst for the partial oxidation of paraffinic hydrocarbons, such as ethane, propane, naphtha, and natural gas condensates, to olefins, such as ethylene and propylene. The process involves contacting a paraffinic hydrocarbon with oxygen in the presence of hydrogen and a catalyst under autothermal process conditions. Preheating the feed decreases oxygen consumption and increases the net hydrogen balance. The catalyst comprises a Group 8B metal, preferably, a platinum group metal, and at least one promoter selected from Groups 1B, 6B, 3A, 4A, and 5A, optionally supported on a catalytic support, such as magnesia or alumina. In preferred embodiments, the support is pretreated with a support modifier selected from Groups 1A, 2A, 3B, 4B, 5B, 6B, 1B, 3A, 4A, 5A, the rare earth lanthanides, and the actinides. A modified fluidized bed reactor is disclosed for the process.
    Type: Grant
    Filed: September 1, 1999
    Date of Patent: May 20, 2003
    Assignee: Dow Global Technologies Inc.
    Inventors: Sameer S. Bharadwaj, Joseph J. Maj, Jonathan H. Siddall, Mark D. Bearden, Craig B. Murchison, Gerald E. Lazaruk
  • Publication number: 20030065235
    Abstract: A catalyst useful for the production of olefins from alkanes via oxidative dehydrogenation (ODH) is disclosed. The catalyst includes a base metal, metal oxide, or combination thereof and a refractory support. The base metal is selected from the group containing Group IB-VIIB metals, Group IIIA-VA metals, Lanthanide metals, iron, cobalt, and nickel. The metal oxide is selected from the group containing alumina, stabilized aluminas, zirconia, stabilized zirconias, titania, ytteria, silica, niobia, and vanadia. The catalyst does not contain any precious metals; it is activated by higher preheat temperatures. As a result, similar conversions are achieved at a considerably lower catalyst cost.
    Type: Application
    Filed: April 8, 2002
    Publication date: April 3, 2003
    Inventors: Joe D. Allison, Lisa M. Budin
  • Publication number: 20020077518
    Abstract: Novel oxidative dehydrogenation catalysts which are useful in vapor-phase oxidative dehydrogenation of lower alkanes with molecular oxygen to produce corresponding olefins at high yields are provided. The catalysts are characterized by containing Mn as the essential component and a crystal phase which is identified by the peaks appearing on their X-ray diffraction spectra (per Cu—K&agr; cathode) where the diffraction angle 2&thgr; (±0.3°) is at 32.9°, 55.2°, 23.1°, 38.2° and 65.8°. The use of those catalysts enables production of the olefins at high yields.
    Type: Application
    Filed: October 23, 2001
    Publication date: June 20, 2002
    Applicant: NIPPON SHOKUBAI CO., LTD.
    Inventor: Nobuji Kishimoto
  • Patent number: 6218591
    Abstract: The present invention relates to new crystalline zeolite SSZ-36 prepared using a cyclic or polycyclic quaternary ammonium cation templating agent.
    Type: Grant
    Filed: June 11, 1999
    Date of Patent: April 17, 2001
    Assignee: Chevron U.S.A. Inc.
    Inventors: Gregory S. Lee, Stacey I. Zones, Yumi Nakagawa, Susan T. Evans
  • Patent number: 6203694
    Abstract: A method for optimizing the yield of light olefins in a process for the conversion of a heavy hydrocarbon stream to aromatics and light olefins by contacting the heavy hydrocarbon stream with a zeolite catalyst along with the controlled introduction of a paraffin stream co-feed.
    Type: Grant
    Filed: May 13, 1998
    Date of Patent: March 20, 2001
    Assignee: Phillips Petroleum Company
    Inventors: Scott Douglas Love, Charles Alfred Drake
  • Patent number: 6187984
    Abstract: A catalyst composition suitable for the conversion of n-butane to butenes. The same catalyst composition that with chlorination is further suitable, when used in the conversion of n-butane, for the production of an increased amount of BTX (benzene-toluene-xylene) and greater selectivity to the production of isobutylenes than attained with the unchlorinated catalyst. A process for the preparation of catalyst compositions suitable for the conversion of n-butane. Use of the catalyst compositions in processes for the conversion of n-butane.
    Type: Grant
    Filed: June 22, 2000
    Date of Patent: February 13, 2001
    Assignee: Phillips Petroleum Company
    Inventors: An-hsiang Wu, Charles A. Drake
  • Patent number: 6166283
    Abstract: An on-line method of synthesizing or regenerating catalysts for autothermal oxidation processes, specifically, the oxidation of paraffinic hydrocarbons, for example, ethane, propane, and naphtha, to olefins, for example, ethylene and propylene. The catalyst comprises a Group 8B metal, for example, a platinum group metal and, optionally, a promoter, such as tin, antimony, or copper, on a support, preferably a monolith support. On-line synthesis or regeneration involves co-feeding a volatile Group 8B metal compound and/or a volatile promoter compound with the paraffinic hydrocarbon and oxygen into the oxidation reactor under ignition or autothermal conditions.
    Type: Grant
    Filed: September 1, 1999
    Date of Patent: December 26, 2000
    Assignee: The Dow Chemical Company
    Inventors: Sameer S. Bharadwaj, Joseph J. Maj, Jonathan H. Siddall
  • Patent number: 6072097
    Abstract: A process for the production of a mono-olefin from a gaseous paraffinic hydrocarbon having at least two carbon atoms or mixtures thereof comprising reacting said hydrocarbons and molecular oxygen in the presence of a platinum catalyst. The catalyst consists essentially of platinum modified with Sn or Cu and supported on a ceramic monolith.
    Type: Grant
    Filed: September 3, 1998
    Date of Patent: June 6, 2000
    Assignee: Regents of the University of Minnesota
    Inventors: Chikafumi Yokoyama, Sameer S. Bharadwaj, Lanny D. Schmidt
  • Patent number: 5959170
    Abstract: A method for converting methane to higher hydrocarbon products and coproduct water wherein a gas comprising methane and a gaseous oxidant are contacted with a nonacidic catalyst at temperatures within the range of about 700 to 1200.degree. C. A preferred catalyst comprises an alkali component associated with a support material. Results obtained over alkali-promoted solids are enhanced when the contacting is conducted in the presence of halogen promoters.
    Type: Grant
    Filed: May 24, 1985
    Date of Patent: September 28, 1999
    Assignee: Atlantic Richfield Company
    Inventor: Howard P. Withers, Jr.
  • Patent number: 5905180
    Abstract: A process for the production of a mono-olefin from a gaseous paraffinic hydrocarbon having at least two carbon atoms or mixtures thereof comprising reacting said hydrocarbons and molecular oxygen in the presence of a platinum catalyst. The catalyst consists essentially of platinum modified with Sn or Cu and supported on a ceramic monolith.
    Type: Grant
    Filed: September 30, 1996
    Date of Patent: May 18, 1999
    Assignee: Regents of the University of Minnesota
    Inventors: Chikafumi Yokoyama, Sameer S. Bharadwaj, Lanny D. Schmidt
  • Patent number: 5821387
    Abstract: Alkyl-substituted polyarenes of the formula ##STR1## in which R is alkyl and Ar.sub.res is an aryl residue, are prepared from aryl ketones by reaction of the latter with 1-cyclohexenyloxytrimethylsilane in the presence of a Friedel-Crafts catalyst. When R is methyl and Ar.sub.res is a naphthyl residue, the reaction serves as a step in a reaction scheme leading to crisnatol mesylate, a pharmaceutical useful in the treatment of brain cancer.
    Type: Grant
    Filed: December 22, 1997
    Date of Patent: October 13, 1998
    Assignee: Aerojet-General Corporation
    Inventors: Thomas G. Archibald, James C. Barnard, Der-Shing Huang
  • Patent number: 5817904
    Abstract: A method for converting methane by an oxidative coupling reaction to longer chain hydrocarbons comprising cofeeding methane and oxygen simultaneously and continuously into a reaction zone to form a mixture, contacting said methane and oxygen mixture under oxidative coupling reaction conditions with a solid catalyst consisting essentially of manganese oxide and silicon oxide, promoted with an alkaline metal and non metal, to form longer chain hydrocarbons wherein the manganese, silicon oxide, alkali metal and non metal are present in a molar ratio 0-0.5:93.2-93.7:4.2:2.1.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: October 6, 1998
    Assignee: Repsol Petroleo S.A.
    Inventors: Sebastian Vic, Miguel A. Pena, Pilar Terreros, Juan P. Gomez, Jose L. Garcia-Fierro, Juan M. Jimenez
  • Patent number: 5811622
    Abstract: A process for the dehydrogenation of a dehydrogenatable hydrocarbon by (1) contacting the dehydrogenatable hydrocarbon with a liquid alkali metal in a dehydrogenation zone to produce a stream containing a dehydrogenated hydrocarbon and an unconverted dehydrogenatable hydrocarbon, and an alkali metal hydride; (2) heating the alkali metal hydride to produce a heated liquid alkali metal and hydrogen; (3) recycling the heated liquid alkali metal to the dehydrogenation zone; (4) contacting the stream containing dehydrogenated hydrocarbon and unconverted dehydrogenatable hydrocarbon with a selective adsorbent to produce a stream containing dehydrogenated hydrocarbon and a stream containing an unconverted hydrogenatable hydrocarbon; (5) recycling the stream of the unconverted dehydrogenatable hydrocarbon to the dehydrogenation zone; and (6) recovering the stream containing dehydrogenated hydrocarbon.
    Type: Grant
    Filed: September 27, 1996
    Date of Patent: September 22, 1998
    Assignee: UOP
    Inventor: Anil R. Oroskar
  • Patent number: 5763722
    Abstract: An improved method for the oxidative conversion of methane into higher hydrocarbons in which methane and oxygen are continuously and simultaneously cofed into a reaction zone under effective oxidative coupling conditions and contacted with a solid catalyst consisting essentially of a catalyst having a composition of empirical formula Ce.sub.a Na.sub.b Ca.sub.100 O.sub.x wherein a is in the range 0.03 to 2.0, b is in the range of 0.7 to 7.0 and oxygen is present in a molar amount sufficient to fulfill the valence requirements of cerium, sodium and calcium.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: June 9, 1998
    Assignee: Repsol Petroleo S.A.
    Inventors: Sebastian Vic, Miguel A. Pena, Pilar Terreros, Juan P. Gomez, Jose L. Garcia-Fierro, Juan M. Jimenez
  • Patent number: 5744667
    Abstract: Gasoline range olefins such as trimethyl pentene are saturated to the corresponding paraffins such as trimethylpentane by hydrogen transfer from lower molecular weight paraffins using a catalyst comprising platinum supported on a large pore borosilicate zeolite which has been partially neutralized by the addition of alkali cations.
    Type: Grant
    Filed: December 31, 1996
    Date of Patent: April 28, 1998
    Assignee: Texaco Inc.
    Inventor: Regis J. Pellet
  • Patent number: 5705728
    Abstract: The present invention provides an efficient process for the production of ethylene or a mixture of ethylene and vinyl chloride, in which some 1,2-dichloroethane (EDC) may also be produced, by reacting chlorine with ethane. The process is characterized by a conversion of ethane per pass through the reactor of at least about 50%, and a combined molar yield of ethylene and vinyl chloride of at least about 80% based on the ethane consumed. In accordance with this invention, there is provided a process for preparing ethylene or a mixture of ethylene and vinyl chloride by the reaction of ethane and chlorine which comprises:(a) providing a stream of ethane feed gas and a stream of chlorine feed gas;(b) preheating either said ethane stream only or both said ethane and chlorine streams;(c) thoroughly mixing said ethane and chlorine feed gases within about one second and at a molar ratio of ethane to chlorine of at least about 0.9:1.
    Type: Grant
    Filed: February 10, 1995
    Date of Patent: January 6, 1998
    Assignee: Occidental Chemical Corporation
    Inventors: Krishnan Viswanathan, Hang-Chang Bobby Chen, Sidney W. Benson
  • Patent number: 5663472
    Abstract: A process for reacting ethane with chlorine to produce a mixture of ethylene and vinyl chloride is disclosed. The process involves the intimate mixing of ethane and chlorine in an ethane to chlorine ratio of at least about 0.9:1 at a temperature such that ethane and chlorine do not react during mixing, and heating the mixture to a temperature above about 215.degree. C. to commence the reaction, allowing the reaction to proceed for a period of less than about 1 minute, and providing sufficient heat to the reacting mixture so that the reacted mixture will have a temperature between about 400.degree. C. and about 800.degree. C.
    Type: Grant
    Filed: February 7, 1995
    Date of Patent: September 2, 1997
    Assignee: University of Southern California
    Inventors: Sidney W. Benson, Maja A. Weissman
  • Patent number: 5639929
    Abstract: A process for the oxidative dehydrogenation of hydrocarbons is disclosed in which C.sub.2 -C.sub.6 alkanes are contacted with an oxygen containing gas in a fluidized catalyst bed of platinum, rhodium, nickel or platinum-gold supported on .alpha.-alumina or zirconia. Ethane is dehydrogenated to ethylene and higher alkanes are dehydrogenated to ethylene, propylene and iso-butylene.
    Type: Grant
    Filed: April 17, 1995
    Date of Patent: June 17, 1997
    Assignee: Regents of the University of Minnesota
    Inventors: Sameer S. Bharadwaj, Lanny D. Schmidt
  • 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: 5530171
    Abstract: There is provided a process for the net catalytic oxidative dehydrogenation of alkanes to produce alkenes. The process involves simultaneous equilibrium dehydrogenation of alkanes to alkenes and combustion of the hydrogen formed to drive the equilibrium dehydrogenation reaction further to the product alkenes. In the present reaction, the alkane feed is passed into a reactor containing both an equilibrium dehydrogenation catalyst and a reducible metal oxide, whereby the alkane is dehydrogenated and the hydrogen produced is simultaneously and selectively combusted in oxidation/ reduction (REDOX) reaction with the reducible metal oxide. This particular mode of operation is termed a same reactor, REDOX mode. The equilibrium dehydrogenation catalyst may comprise platinum and the reducible metal oxide may contain bismuth, antimony, indium, or molybdenum, or a mixture thereof.
    Type: Grant
    Filed: April 17, 1995
    Date of Patent: June 25, 1996
    Assignee: Mobil Oil Corporation
    Inventors: Pradyot A. Agaskar, Robert K. Grasselli, James N. Michaels, P. Thomas Reischman, David L. Stern, John G. Tsikoyiannis
  • Patent number: 5527978
    Abstract: Methane is converted into higher hydrocarbon products by oxidative coupling, by bringing a gaseous mixture containing methane and oxygen into contact with a solid catalyst formed from calcium oxide, magnesium oxide, a lanthanide oxide plus possibly lithium oxide, wherein:the lithium content is between 0 and 0.20 wt %,the calcium/magnesium atomic ratio is between 0.08 and 0.7, andthe (calcium+magnesium)/lanthanide atomic ratio is between 0.8/1 and 8/1, and preferably between 2/1 and 4/1.
    Type: Grant
    Filed: October 28, 1993
    Date of Patent: June 18, 1996
    Assignee: Eniricerche S.p.A.
    Inventors: Giuseppe Fornasari, Giuseppe Bellussi
  • Patent number: 5527979
    Abstract: There is provided a process for the net catalytic oxidative dehydrogenation of alkanes to produce alkenes. The process involves simultaneous equilibrium dehydrogenation of alkanes to alkenes and combustion of the hydrogen formed to drive the equilibrium dehydrogenation reaction further to the product alkenes. In the present reaction, the alkane feed is dehydrogenated over an equilbrium dehydrogenation catalyst in a first reactor, and the effluent from the first reactor, along with oxygen, is then passed into a second reactor containing a metal oxide catalyst which serves to selectively catalyze the combustion of hydrogen. This particular mode of operation is termed a separate reactor, cofed oxygen mode. The equilibrium dehydrogenation catalyst may comprise platinum and the selective metal oxide combustion catalyst may contain bismuth, antimony, indium, molybdenum, or a mixture thereof.
    Type: Grant
    Filed: April 17, 1995
    Date of Patent: June 18, 1996
    Assignee: Mobil Oil Corporation
    Inventors: Pradyot A. Agaskar, Robert K Grasselli, James N. Michaels, P. Thomas Reischman, David L. Stern, John G. Tsikoyiannis
  • Patent number: 5498816
    Abstract: Process for the dehydrogenation of a hydrocarbon feed stream comprising steps of contacting the feed stream with a dehydrogenation catalyst in at least one dehydrogenation zone and reacting the feed stream to a hydrogen containing effluent stream;admixing to the effluent stream an oxygen containing atmosphere in at least one mixing zone;removing hydrogen from the effluent stream by reaction with oxygen in the oxygen containing atmosphere by contact with a hydrogen oxidation catalyst in at least one hydrogen removing zone,the improvement of which comprises employing massive forms of noble metals or alloys thereof as catalyst in the hydrogen removal zone.
    Type: Grant
    Filed: November 30, 1994
    Date of Patent: March 12, 1996
    Assignee: Haldor Topsoe A/S
    Inventors: Poul E. H. Nielsen, Peter Lehrmann
  • Patent number: 5476981
    Abstract: Solid superacid catalyst, for example sulfated zirconia, is used in the oxidative dehydrogenation of saturated or partially saturated hydrocarbons, for example the conversion of isobutane to isobutylene in the presence of an oxygen-containing oxidizing agent at reaction conditions typically including temperatures from 500 to 1,000 degrees Fahrenheit, superatmospheric pressures, and oxygen/alkane molar ratios from 0.2 to 20. Performance of a metal-oxide or metal-hydroxide oxidative dehydrogenation catalyst may be enhanced by pretreating a solid superacid or other catalyst containing metal oxides or hydroxides at a carbonizing temperature with an organic material, for example an oxygen-containing organic material, to form a carbonaceous layer on the surface thereof prior to use of the catalyst in oxidative dehydrogenation.
    Type: Grant
    Filed: December 29, 1993
    Date of Patent: December 19, 1995
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Benjamin S. Umansky, Chao-Yang Hsu
  • Patent number: 5476980
    Abstract: A process for the dehydrogenation of a dehydrogenatable hydrocarbon by contacting the hydrocarbon with a liquid comprising an alkali metal in a dehydrogenation zone to produce a dehydrogenated hydrocarbon and an alkali metal halide. The resulting alkali metal hydride is heated to produce a heated liquid alkali metal and hydrogen. The heated liquid alkali metal is recycled to the dehydrogenation zone to provide heat and elemental metal.
    Type: Grant
    Filed: December 23, 1994
    Date of Patent: December 19, 1995
    Assignee: UOP
    Inventor: Anil R. Oroskar
  • Patent number: RE35632
    Abstract: In an improved method for converting methane to at least one higher hydrocarbon product and coproduct water which comprises contacting a gas comprising methane and at least one added gaseous oxidant with nonacidic solid, the improvement comprising conducting at least a portion of said contacting in the presence of added water.
    Type: Grant
    Filed: January 19, 1993
    Date of Patent: October 14, 1997
    Assignees: Atlantic Richfield Company, Phillips Petroleum Company
    Inventor: David W. Leyshon
  • Patent number: RE35633
    Abstract: In an improved method for converting methane to at least one higher hydrocarbon product and coproduct water which comprises contacting a gas comprising methane and at least one added gaseous oxidant with nonacidic solid, the improvement comprising conducting at least a portion of said contacting in the presence of added water.
    Type: Grant
    Filed: January 19, 1995
    Date of Patent: October 14, 1997
    Assignee: Atlantic Richfield Company
    Inventor: David W. Leyshon
  • Patent number: RE44822
    Abstract: A process for heterogeneously catalyzed partial dehydrogenation of a hydrocarbon, in which a reaction gas mixture input stream comprising the hydrocarbon to be dehydrogenated is conducted through a fixed catalyst bed disposed in a shaft and the reaction gas mixture input stream is obtained in the shaft by metering an input gas II comprising molecular oxygen upstream of the fixed catalyst bed into an input gas stream I which comprises molecular hydrogen and the hydrocarbon to be dehydrogenated and is flowing within the shaft toward the fixed catalyst bed.
    Type: Grant
    Filed: November 20, 2012
    Date of Patent: April 1, 2014
    Assignee: BASF SE
    Inventors: Claus Hechler, Wilhelm Ruppel, Wolfgang Gerlinger, Wolfgang Schneider, Klaus Joachim Mueller-Engel