From Olefins Utilizing Group Viii Noble Metal Catalyst Patents (Class 560/243)
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Patent number: 11976037Abstract: This invention concerns a process for the production of vinyl esters of carboxylic acids with 3 to 20 carbon atoms, via vinylation in the presence of palladium (Pd) catalyst in combination with copper (Cu) as co-catalyst stabilized by organic salts in the presence of ethylene and air or oxygen.Type: GrantFiled: May 13, 2019Date of Patent: May 7, 2024Assignee: HEXION INC.Inventors: Fabrizio Marras, Leo Sliedregt, Alexander Kraynov
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Patent number: 11167268Abstract: A catalyst includes a carbon black support and active metal particles. A surface of the carbon black support has a relative atomic percentage of oxygen atoms ranged from 2 atom % to 12 atom %. The active metal particles are distributed on the carbon black support. Each of the active metal particles includes rhodium metal and rhodium oxide. A method for manufacturing the catalyst and a method for hydrogenating an aromatic epoxy compound are also provided herein.Type: GrantFiled: October 25, 2019Date of Patent: November 9, 2021Assignee: National Tsing Hua UniversityInventors: Chung-Sung Tan, Wei-Yuan Lu
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Patent number: 10807075Abstract: A process is presented for the management of sulfur on a catalyst. The catalyst is a dehydrogenation catalyst, and sulfur accumulates during the dehydrogenation process. Sulfur compounds are stripped from the spent catalyst and the catalyst is cooled before the regeneration process. The process includes controlling the amount of sulfur that needs to be removed from the catalyst before regeneration.Type: GrantFiled: December 20, 2017Date of Patent: October 20, 2020Assignee: UOP LLCInventors: Wolfgang A. Spieker, Adam D. Ballard, Gregory J. Gajda, J. W. Adriaan Sachtler
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Patent number: 10266475Abstract: A method for preparing acrylic acid, more specifically, to a method for preparing acrylic acid under a neutral condition at high yield in a short time without using a base, unlike the prior art in which a base is essentially used. The acrylic acid is produced using a supported catalyst having a specific composition when preparing acrylic acid by oxidation of allyl alcohol. Particularly, the preparation method can recover acrylic acid rather than acrylic acid salt as a final product, and thus has an advantage that the overall process cost can be reduced by eliminating essential processes in the prior art, such as ion exchange after the acidification process required for the conversion of acrylic acid salt to acrylic acid.Type: GrantFiled: January 31, 2017Date of Patent: April 23, 2019Assignee: LG CHEM, LTD.Inventors: Won Jae Lee, Dong Su Song, Yong Jin Choe, Hyun Joo Lee, Min Su Kim
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Patent number: 10035749Abstract: The present invention is in the field of producing bio-based commodity organic chemicals such as bio-acrylic acid, bio-acrylonitrile, and bio-1,4-butanediol using renewable carbon sources as feedstock. In the first stage of the present invention, bio-1,3-propanediol is derived from renewable carbon sources through microbial fermentation. In the second stage of the present invention, bio-1,3-propanediol is converted into bio-acrylic acid or bio-acrylonitrile or bio-1,4-butanediol.Type: GrantFiled: September 3, 2014Date of Patent: July 31, 2018Assignee: Myriant CorporationInventors: Vijay Gnanadesikan, Ramnik Singh, Rajesh Dasari, Montgomery Alger
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Patent number: 9573877Abstract: The present invention relates to a process for forming vinyl acetate. The process comprises the step of providing a reaction mixture having an initial heat capacity. The reaction mixture comprises acetic acid, oxygen, ethylene, and optionally water. The process further comprises the step of adding to the reaction mixture at least one heat capacity modifier to form an increased heat capacity reaction mixture. The process further comprises the step of contacting the acetic acid, oxygen, and ethylene over a catalyst under conditions effective to form a crude vinyl acetate product. The crude vinyl acetate product comprises vinyl acetate and water.Type: GrantFiled: August 26, 2013Date of Patent: February 21, 2017Assignee: CELANESE INTERNATIONAL CORPORATIONInventors: Pieter Vismans, Naveed Aslam, Tony Hammock, Kevin Hanks, Ilias S. Kotsianis, Tianshu Pan, Daniel Rangel-Osalde, Kelly Wallace
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Patent number: 9056313Abstract: Catalyst compositions of palladium supported on alumina or zirconium oxide supports having low or no silicon dioxide contents and having a specific surface area or modified with alkali, alkaline earth, or phosphine oxide compounds are selective in a vapor phase hydrogenolysis reaction to convert cyclic acetal compounds and/or cyclic ketal compounds in the presence of hydrogen to their corresponding hydroxy ether hydrocarbon reaction products.Type: GrantFiled: June 24, 2011Date of Patent: June 16, 2015Assignee: Eastman Chemical CompanyInventors: Thomas James Devon, Damon Ray Billodeaux
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Patent number: 8946468Abstract: A process for producing an unsaturated bond-containing ester compound includes reacting an internal olefin or a cyclic olefin having one carbon-carbon double bond or more at a position other than terminals of a molecule thereof (the internal olefin and the cyclic olefin may each contain a hetero atom) with a carboxylic acid in an amide-based solvent represented by a formula (1) in the presence of a palladium catalyst, a base, and molecular oxygen, to obtain an ester compound having an unsaturated bond.Type: GrantFiled: February 18, 2011Date of Patent: February 3, 2015Assignees: JX Nippon Oil & Energy Corporation, Osaka UniversityInventors: Kiyotomi Kaneda, Hisashi Sone
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Patent number: 8822717Abstract: Disclosed is a method for controlling a vinyl acetate production process. The method comprises reacting ethylene, acetic acid, and an oxygen-containing gas in the presence of a catalyst in a reactor to produce vinyl acetate, measuring the concentration of a component involved in or associated with the reaction and/or any of the subsequent steps by Raman spectroscopic analysis, and adjusting the conditions in the reactor or in any of the subsequent steps in response to the measured concentration of the component to achieve a proper control of the reaction or any of the subsequent steps.Type: GrantFiled: November 24, 2010Date of Patent: September 2, 2014Assignee: LyondellBassell Acetyls, LLCInventors: Brian A. Salisbury, Noel C. Hallinan, Jenny M. Oran Osment
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Publication number: 20140081041Abstract: A method for producing a shell catalyst which is suitable for the synthesis of alkenyl carboxylic acid esters, in particular for producing vinyl acetate monomer (VAM) from ethylene or allyl acetate monomer from propylene by means of oxy-acetylation. Also, a shell catalyst that can be obtained by the method according to the invention, as well as the use of the shell catalyst produced using the method for producing alkenyl carboxylic acid esters, in particular vinyl acetate monomer (VAM) and allyl acetate monomer.Type: ApplicationFiled: September 19, 2013Publication date: March 20, 2014Applicant: Clariant International Ltd.Inventors: Roman Bobka, Gerhard Mestl, Peter Scheck, Carolin Fischer, Martin Schoenfelder
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Publication number: 20140081040Abstract: Methods of forming noble metal catalysts, noble metal catalysts formed therefrom and process for using noble metal catalysts are described herein. The methods generally include contacting a support material with a pre-treatment agent including a dilute basic solution of an alkali or alkaline earth metal to form a contacted support; drying the contacted support to form a pre-treated support; and impregnating the pre-treated support with at least one noble metal to form the noble metal catalyst.Type: ApplicationFiled: September 20, 2012Publication date: March 20, 2014Applicant: LYONDELL CHEMICAL TECHNOLOGY, L.P.Inventors: Daniel T. Shay, Sallie J. Lee
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Publication number: 20140066650Abstract: A process for producing vinyl acetate in which a secondary reactant stream is obtained from a predehydrating column and reacted in a sidecar reactor to further increase conversion of ethylene, acetic acid, and molecular oxygen and increase production of vinyl acetate.Type: ApplicationFiled: August 28, 2013Publication date: March 6, 2014Applicant: Celanese International CorporationInventors: Naveed Aslam, Sayanti Basu, Wei Qi
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Patent number: 8399700Abstract: A process is disclosed for the production of vinyl acetate where a mixture of ethylene, acetic acid, and oxygen is reacted in the presence of a catalyst to produce a product mixture of vinyl acetate, ethylene, carbon dioxide, acetic acid, water, ethyl acetate, and ethylene glycol diacetate. The product mixture contains both a gaseous phase and a liquid phase, which are separated. The gas phase contains at least carbon dioxide, which is removed via gas stream. The crude vinyl acetate stream is removed via a liquid stream. The crude vinyl acetate is then further separated to isolate a stream containing at the majority of the ethylene glycol diacetate. The ethylene glycol diacetate stream is then methanolyzed in the presence of a methanolyzing catalyst, to recover methyl acetate, which can be optionally recycled as a feed stock to an acetic acid plant.Type: GrantFiled: April 15, 2011Date of Patent: March 19, 2013Assignee: Lyondell Chemical Technology, L.P.Inventors: Brian Salisbury, Michael E. Fitzpatrick, Wayne Joseph Brtko, Noel C. Hallinan
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Patent number: 8362292Abstract: A process for producing allyl acetate is disclosed. The process comprises reacting a feed comprising propylene, acetic acid, oxygen, and carbon dioxide in the presence of a supported palladium catalyst. The feed comprises from 2 to 6 mole percent carbon dioxide, which improves the selectivity to allyl acetate.Type: GrantFiled: August 10, 2012Date of Patent: January 29, 2013Assignee: Lyondell Chemical Technology, L.P.Inventors: Andrew P. Kahn, Elizabeth I. Ross-Medgaarden
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Publication number: 20120316360Abstract: A process for producing an ?,?-unsaturated bond-containing ester compound, comprising: reacting an internal olefin or a cyclic olefin having one carbon-carbon double bond or more at a position other than terminals of a molecule thereof (the internal olefin and the cyclic olefin may each contain a hetero atom) with a carboxylic acid in an amide-based solvent in the presence of a palladium catalyst, a base, and molecular oxygen, thereby bonding a carboxyl group of the carboxylic acid to at least one of carbon atoms constituting the carbon-carbon double bond and carbon atoms at allylic positions of the internal olefin or the cyclic olefin, to obtain an ester compound having an ?,?-unsaturated bond, the amide-based solvent being represented by the following formula (1): (in the formula (1), R1 represents an alkyl group having 1 to 4 carbon atoms; R2 and R3 each independently represent an alkyl group having 1 to 4 carbon atoms or an aryl group; and when R1 and R2 are alkyl groups, R1 and R2 may be bondeType: ApplicationFiled: February 18, 2011Publication date: December 13, 2012Applicants: Osaka University, JX NIPPON OIL & ENERGY CORPORATIONInventors: Kiyotomi Kaneda, Hisashi Sone
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Publication number: 20120289737Abstract: A method for producing a shell catalyst which comprises, in the outer shell, one or more of the following metals: Pd, Pt, Ag and Au. Also the use of the shell catalyst produced using the method according to the invention for the production of vinyl acetate monomer, in the hydrogenation of hydrocarbons, in particular the selective hydrogenation of polyunsaturated hydrocarbon compounds, or in the oxidation of alcohols to ketones/aldehydes/carboxylic acids.Type: ApplicationFiled: May 10, 2012Publication date: November 15, 2012Applicant: SUED-CHEMIE AGInventors: Alfred HAGEMEYER, Peter SCHECK, Gerhard MESTL, Alice KYRIOPOULOS, Carolin FISCHER
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Patent number: 8309757Abstract: This invention provides an integrated two stage economical process for the production of vinyl acetate monomer (VAM) from acetic acid in the vapor phase. First, acetic acid is selectively hydrogenated over a hydrogenating catalyst composition to form ethylene either in a single reactor zone or in a dual rector zone wherein the intermediate hydrogenated products are either dehydrated and/or cracked to form ethylene. In a subsequent second stage so formed ethylene is reacted with molecular oxygen and acetic acid over a suitable catalyst to form VAM. In an embodiment of this invention reaction of acetic acid and hydrogen over a hydrogenation catalyst and subsequent reaction over a dehydration catalyst selectively produces ethylene, which is further mixed with acetic acid and molecular oxygen and reacted over a supported palladium/gold/potassium catalyst.Type: GrantFiled: December 2, 2011Date of Patent: November 13, 2012Assignee: Celanese International CorporationInventors: Victor Johnston, Barabra Kimmich, Deborah Repman, James Zink, Josefina Chapman, Laiyuan Chen
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Patent number: 8227369Abstract: A layered composition which can be used in various processes has been developed. The composition comprises an inner core such as a cordierite core and an outer layer comprising a refractory inorganic oxide, a fibrous component and an inorganic binder. The refractory inorganic oxide layer can be alumina, zirconia, titania, etc. while the fibrous component can be titania fibers, silica fibers, carbon fibers, etc. The inorganic oxide binder can be alumina, silica, zirconia, etc. The layer can also contain catalytic metals such as gold and platinum plus other modifiers. The layered composition is prepared by coating the inner core with a slurry comprising the refractory inorganic oxide, fibrous component, an inorganic binder precursor and an organic binding agent such as polyvinyl alcohol. The composition can be used in various hydrocarbon conversion processes including production of vinyl acetate.Type: GrantFiled: May 25, 2005Date of Patent: July 24, 2012Assignee: Celanese International Corp.Inventors: Tao Wang, Dean E. Rende, James E. Rekoske, Jeffery C. Bricker, Jeffrey L. Boike, Masao Takayama, Kouji Hara, Nobuyuki Aoi
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Patent number: 7897804Abstract: A layered composition which can be used in various processes has been developed. The composition comprises an inner core such as a cordierite core and an outer layer comprising a refractory inorganic oxide, a fibrous component and an inorganic binder. The refractory inorganic oxide layer can be alumina, zirconia, titania, etc. while the fibrous component can be titania fibers, silica fibers, carbon fibers, etc. The inorganic oxide binder can be alumina, silica, zirconia, etc. The layer can also contain catalytic metals such as gold and platinum plus other modifiers. The layered composition is prepared by coating the inner core with a slurry comprising the refractory inorganic oxide, fibrous component, an inorganic binder precursor and an organic binding agent such as polyvinyl alcohol. The composition can be used in various hydrocarbon conversion processes including production of vinyl acetate.Type: GrantFiled: April 7, 2008Date of Patent: March 1, 2011Assignee: Celanese International Corp.Inventors: Tao Wang, Dean E. Rende, James E. Rekoske, Jeffery C. Bricker, Jeffrey L. Boike, Masao Takayama, Kouji Hara, Nobuyuki Aoi
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Patent number: 7855303Abstract: This invention provides an integrated two stage economical process for the production of vinyl acetate monomer (VAM) from acetic acid in the vapor phase. First, acetic acid is selectively hydrogenated over a hydrogenating catalyst composition to form ethylene either in a single reactor zone or in a dual rector zone wherein the intermediate hydrogenated products are either dehydrated and/or cracked to form ethylene. In a subsequent second stage so formed ethylene is reacted with molecular oxygen and acetic acid over a suitable catalyst to form VAM. In an embodiment of this invention reaction of acetic acid and hydrogen over a hydrogenation catalyst and subsequent reaction over a dehydration catalyst selectively produces ethylene, which is further mixed with acetic acid and molecular oxygen and reacted over a supported palladium/gold/potassium catalyst.Type: GrantFiled: November 14, 2008Date of Patent: December 21, 2010Assignee: Celanese International CorporationInventors: Victor J. Johnston, Laiyuan Chen, James H. Zink, Josefina T. Chapman, Barbara F. Kimmich, Deborah R. Repman
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Publication number: 20100168465Abstract: A catalyst is produced by a process that comprises at least a step of impregnating a carrier with an alkali solution having a mass of greater than 0.9 times and no greater than 1.0 times the amount of water absorption of the carrier, a step of further impregnating the carrier by contact with a solution A comprising at least a compound containing palladium or platinum and a compound containing a Group 11 element, a step of reduction treatment and a step of loading an acetic acid salt on the carrier, wherein the carrier is first impregnated with the alkali solution and then the contacted with solution A to form a catalyst precursor, and wherein the total amount of the alkali solution and solution A is a mass of at least 1.1 times and no greater than 10.0 times the amount of water absorption of the carrier. A catalyst for alkenyl acetate production is obtained that exhibits improved activity and selectivity.Type: ApplicationFiled: August 8, 2007Publication date: July 1, 2010Inventor: Meiko Saihata
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Publication number: 20100121100Abstract: Disclosed is a catalyst. The catalyst comprises palladium, gold, and a support comprising titanium dioxide and tungsten trioxide. The support preferably comprises from 75 wt % to 99 wt % of titanium dioxide and from 1 wt % to 25 wt % of tungsten trioxide. A method for preparing the catalyst is also disclosed. The method comprises impregnating the support with a palladium compound and a gold compound, calcining the impregnated support, and then reducing the calcined support. Further disclosed is a method for preparing vinyl acetate with the catalyst. The catalyst exhibits improved catalytic activity and selectivity.Type: ApplicationFiled: November 12, 2008Publication date: May 13, 2010Inventor: Daniel Travis Shay
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Patent number: 7491843Abstract: Acetic acid and/or vinyl acetate are produced by an integrated process which comprises the steps: (a) contacting in a first reaction zone a gaseous feedstock comprising ethylene and/or ethane and optionally steam with a molecular oxygen-containing gas in the presence of a catalyst active for the oxidation of ethylene to acetic acid and/or ethane to acetic acid and ethylene to produce a first product stream comprising acetic acid, water and ethylene (either as unreacted ethylene and/or as co-produced ethylene) and optionally also ethane, carbon monoxide, carbon dioxide and/or nitrogen; (b) contacting in a second reaction zone in the presence or absence of additional ethylene and/or acetic acid at least a portion of the first gaseous product stream comprising at least acetic acid and ethylene and optionally also one or more of water, ethane, carbon monoxide, carbon dioxide and/or nitrogen with a molecular oxygen-containing gas in the presence of a catalyst active for the production of vinyl acetate to produceType: GrantFiled: November 2, 2001Date of Patent: February 17, 2009Assignee: BP Chemicals LimitedInventors: Simon Jobson, Derrick John Watson
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Patent number: 7468455Abstract: The invention provides methods, apparatus and chemical systems for making vinyl acetate from ethylene, oxygen, and acetic acid.Type: GrantFiled: October 20, 2005Date of Patent: December 23, 2008Assignees: Velocys, Inc., Celanese International CorporationInventors: Terry Mazanec, Victor J. Johnston, Michael Huckman, Sean P. Fitzgerald, James A. Foster, Daniel Lindley, Anna Lee Tonkovich, Francis P. Daly, Leslie Wade, Tony Hammock, Thomas Yuschak, Bin Yang, Kai Jarosch
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Publication number: 20080287703Abstract: A layered composition which can be used in various processes has been developed. The composition comprises an inner core such as a cordierite core and an outer layer comprising a refractory inorganic oxide, a fibrous component and an inorganic binder. The refractory inorganic oxide layer can be alumina, zirconia, titania, etc. while the fibrous component can be titania fibers, silica fibers, carbon fibers, etc. The inorganic oxide binder can be alumina, silica, zirconia, etc. The layer can also contain catalytic metals such as gold and platinum plus other modifiers. The layered composition is prepared by coating the inner core with a slurry comprising the refractory inorganic oxide, fibrous component, an inorganic binder precursor and an organic binding agent such as polyvinyl alcohol. The composition can be used in various hydrocarbon conversion processes including production of vinyl acetate.Type: ApplicationFiled: April 7, 2008Publication date: November 20, 2008Inventors: Tao Wang, Dean E. Rende, James E. Rekoske, Jeffery C. Bricker, Jeffrey L. Boike, Masao Takayama, Kouji Hara, Nobuyuki Aoi
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Patent number: 7411107Abstract: A process for the oxidation of a C2 to C4 alkane to produce the corresponding alkene and carboxylic acid which process comprises separation of the alkene from a mixture of the alkene, the alkane and oxygen by absorption in a metallic salt solution, and recovery of an alkene-rich stream from the metallic salt solution. Integrated processes for the production of alkyl carboxylate and alkenyl carboxylate, which processes comprise oxidation of a C2 to C4 alkane to produce the corresponding alkene and carboxylic acid, separation of the alkene from a mixture of the alkene, the alkane and oxygen by absorption in a metallic salt solution, and recovery of an alkene-rich stream from the metallic salt solution for use in production of alkyl carboxylate or alkenyl carboxylate.Type: GrantFiled: February 12, 2003Date of Patent: August 12, 2008Assignee: BP Chemicals LimitedInventor: Andrew Richard Lucy
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Patent number: 7297324Abstract: Microchannel devices and method of use are disclosed wherein a reaction microchamber 52 is in thermal contact with a heat exchange channel 61. An equilibrium limited exothermic chemical process occurs in the reaction microchamber 52. Sufficient heat is transferred to the heat exchange channels to substantially lower the temperature in the reaction microchamber 52 down its length to substantially increase at least one performance parameter of the exothermic chemical process relative to isothermal operation. Optionally, an endothermic reaction occurs in the heat exchange channel 61 which is sustained by the exothermic chemical process occurring the exothermic reaction chamber. Both the reaction chamber 52 and the heat exchange channel 61 can be of micro dimension. Catalyst 75 can be provided in the microchamber 52 in sheet form such that reactants flow by the catalyst sheet.Type: GrantFiled: March 11, 2003Date of Patent: November 20, 2007Assignee: Battelle Memorial InstituteInventors: Ward E. TeGrotenhuis, David L. King, Greg A. Whyatt, Christopher M. Fischer, Robert S. Wegeng, Kriston P. Brooks
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Patent number: 7211688Abstract: Process for producing an alkyl carboxylate, comprising contacting in an oxidation reaction zone a C2 to C4 alkane, a molecular oxygen-containing gas, the corresponding alkene and optionally water, in the presence of at least one catalyst active for the oxidation of the alkane to the corresponding alkene and carboxylic acid, to produce a first product stream comprising alkene, unreacted alkane, carboxylic acid and water; separating in a first separation means at least a portion of the product stream produced in the oxidation reaction zone into a gaseous stream comprising alkene and unreacted alkane and a liquid stream comprising carboxylic acid and water; and separating by chemical treatment at least a portion of the gaseous stream obtained from the first separation means into respective streams rich in alkene and alkane; wherein the chemical treatment comprises the steps of: (1) contacting the alkene/alkane gaseous stream with a solution of a metal salt capable of selectively chemically absorbing the alkene tType: GrantFiled: February 12, 2003Date of Patent: May 1, 2007Assignee: BP Chemicals LimitedInventors: Robert William Clarke, Robert Croll, Andrew Richard Lucy, Bruce Leo Williams
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Patent number: 7189377Abstract: 1.Type: GrantFiled: July 26, 2000Date of Patent: March 13, 2007Assignee: BP Chemicals LimitedInventors: Simon Jobson, Derrick John Watson
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Patent number: 6852877Abstract: A process for the production of vinyl acetate comprising contacting in a first reaction zone a gaseous feedstock comprising essentially ethane with a molecular oxygen-containing gas in the presence of a catalyst to produce a first product stream comprising acetic acid; contacting in a second reaction zone a gaseous feedstock comprising essentially ethane with a molecular oxygen-containing gas in the product stream comprising ethylene; contacting in a third reaction one the first gaseous product stream and the second gaseous product stream with a molecular oxygen-containing gas in the presence of a catalyst to produce a fourth product stream comprising vinyl acetate; separating the product stream from step (3) and recovering vinyl acetate from said product stream from step (3).Type: GrantFiled: May 19, 2000Date of Patent: February 8, 2005Assignee: Celanese International Corp.Inventors: Sabine Zeyss, Uwe Dingerdissen, John Fritch
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Patent number: 6815394Abstract: A phenyl ester is produced by allowing benzene, a carboxylic acid and molecular oxygen to react with each other in the presence of a catalyst comprising (A) palladium, (B) at least one element selected from elements of groups 13, 14, 15, and 16 and the fourth to sixth periods of the periodic table, and (C) at least one element selected from elements of groups 3, 4 and lanthanoid elements of the periodic table. Preferably, element (B) is selected from elements of group 16 and the fourth to sixth periods of the periodic table, and element (C) is contained in a metal oxide form in the catalyst.Type: GrantFiled: November 13, 2002Date of Patent: November 9, 2004Assignee: Tosoh CorporationInventors: Yoshihiko Mori, Takao Doi, Tetsuo Asakawa, Takanori Miyake
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Patent number: 6809218Abstract: Porous microcomposites have been prepared from perfluorinated ion-exchange polymer and metal oxides such as silica using the sol-gel process. Such microcomposites possess high surface area and exhibit extremely high catalytic activity.Type: GrantFiled: October 7, 2003Date of Patent: October 26, 2004Assignee: E. I. du Pont de Nemours and CompanyInventors: Mark Andrew Harmer, Qun Sun
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Patent number: 6768013Abstract: A novel process for the direct oxidation of hydrogen and hydrocarbons is disclosed, where the explosion risks inherent in gas phase oxidations are substantially eliminated. Gaseous oxidation reactants are soluble in a first reaction solvent phase such as a perfluorocarbon (e.g. C8F18) and the oxidation product is preferentially soluble in a second product solvent phase such as water or a dilute acid. A solid catalyst such as palladium on alumina is then contacted with the dissolved reactants. The oxidation product such as hydrogen peroxide may be separated from the reaction solvent phase by extraction into the immiscible product solvent phase and then separated from it by distillation, thereby allowing re-use of the aqueous phase. The present invention may be carried out using a two-phase reaction system whereby both the reaction solvent and product solvent are contained within a reaction vessel into which the solid catalyst is slurried and mechanically agitated to promote the reaction.Type: GrantFiled: June 15, 2001Date of Patent: July 27, 2004Assignee: UOP LLCInventor: Peter R. Pujado
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Patent number: 6696596Abstract: A process for preparing vinyl acetate in the gas phase from ethylene, acetic acid and oxygen or oxygen-containing gases over a catalyst, consisting essentially of palladium and/or its compounds, gold and/or its compounds and alkali metal compounds on a support, wherein the catalyst further comprises vanadium and/or its compounds and catalyst therefrom.Type: GrantFiled: October 24, 2001Date of Patent: February 24, 2004Assignee: Celanese Chemicals Europe GmbHInventors: Bernhard Herzog, Axel Schafer, Karl H Renkel
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Patent number: 6649789Abstract: A process for the vapor phase preparation of vinyl acetate in the presence of a catalyst of 0.2 to 1.3% by weight of gold or a gold compound, 0.3 to 10% by weight of an alkali metal compound, 0.5 to 2.0% by weight of a palladium compound and 0.01 to 1% by weight of a lanthanoid compound.Type: GrantFiled: June 18, 2002Date of Patent: November 18, 2003Assignee: Celanese Chemicals Europe GmbHInventors: Bernhard Herzog, Tao Wang, Toan Nicolau
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Patent number: 6620965Abstract: A process for producing vinyl acetate comprising reacting ethylene, acetic acid and oxygen together in at least partially liquid phase in the presence of a catalyst comprising a noble metal component.Type: GrantFiled: March 8, 2002Date of Patent: September 16, 2003Assignee: Catalytic Distillation TechnologiesInventors: John R. Adams, Willibrord A. Groten, Speros P. Nemphos
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Publication number: 20030144544Abstract: A composition and process for making same in which the composition comprises support particles having at least one catalytically active metal or precursor thereof distributed therein in a layer below the surface of said particle, said layer being between an inner and an outer region of said support particle) and each of said inner and outer regions having a lower concentration of said metal or precursor thereof than said layer.Type: ApplicationFiled: January 9, 2003Publication date: July 31, 2003Applicant: BP Chemicals Limited & Johnson Matthey Public Limited CompanyInventors: Michael James Baker, John William Couves, Kenneth George Griffin, Peter Johnston, James Colin McNicol, George Frederick Salem
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Publication number: 20030139624Abstract: A process for preparing a supported metal catalyst composition which comprises impregnating microspheroidal support particles with a solution of at least one catalytically active metal, or precursor, drying the impregnated support particles and then treating the mobile metal, or precursor in a mobile state with a liquid comprising at least one reducing agent to deposit and immobilize the metal, or its precursor, in the support particles such that the metal, or its precursor, is distributed in the support particle in a layer below the surface of the support particle, the layer being between an inner and an outer region having a lower concentration of metal or precursor. Also, a composition comprising microspheroidal support particles having at least one catalytically active metal or precursor thereof distributed in a layer below the surface of the particles, the layer being between an inner and an outer region of the support particle each having a lower concentration of metal or precursor.Type: ApplicationFiled: January 6, 2003Publication date: July 24, 2003Applicant: BP Chemicals LimitedInventors: Michael James Baker, John William Couves, Kenneth George Griffin, Peter Johnston, James Colin McNicol, George Frederick Salem
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Patent number: 6541660Abstract: A process is proposed for preparing C5 acetate for Vitamin A synthesis by hydroformylation of 3,4-diacetoxybut-1-ene (3,4-DABE), according to which a 3,4-DABE is used which is obtained by acetoxylation of 1,3-butadiene with acetic acid and air in the presence of a catalyst and removing by distillation the 3,4-DABE formed in this case as by-product.Type: GrantFiled: March 27, 2002Date of Patent: April 1, 2003Assignee: BASF AktiengesellschaftInventors: Udo Rheude, Maximilian Vicari, Werner Aquila, Günter Wegner, Jörg Niekerken
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Patent number: 6528679Abstract: A phenyl ester is produced by allowing benzene, a carboxylic acid and molecular oxygen to react with each other in the presence of a catalyst comprising (A) palladium, (B) at least one element selected from elements of groups 13, 14, 15, and 16 and the fourth to sixth periods of the periodic table, and (C) at least one element selected from elements of groups 3, 4 and lanthanoid elements of the periodic table. Preferably, element (B) is selected from elements of group 16 and the fourth to sixth periods of the periodic table, and element (C) is contained in a metal oxide form in the catalyst. The phenyl ester can be converted to phenol by hydrolysis or ester exchange.Type: GrantFiled: September 27, 2000Date of Patent: March 4, 2003Assignee: Tosoh CorporationInventors: Yoshihiko Mori, Takao Doi, Tetsuo Asakawa, Takanori Miyake
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Publication number: 20020198404Abstract: A process for the vapor phase preparation of vinyl acetate in the presence of a catalyst of 0.2 to 1.3% by weight of gold or a gold compound, 0.3 to 10% by weight of an alkali metal compound, 0.5 to 2.0% by weight of a palladium compound and 0.01 to 1% by weight of a lanthanoid compound.Type: ApplicationFiled: June 18, 2002Publication date: December 26, 2002Applicant: Celanese Chemicals Europe GmbHInventors: Bernhard Herzog, Tao Wang, Toan Nicolau
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Patent number: 6472556Abstract: A catalyst for use in the production of vinyl acetate which comprises (1) a catalyst support, (2) palladium, (3) an acid, (4) at least one acetic acid catalyst promoter and (5) at least one vinyl acetate promoter and/or co-promoter. A process for the production of vinyl acetate from ethylene and an oxygen-containing gas using the catalyst.Type: GrantFiled: March 27, 2001Date of Patent: October 29, 2002Assignee: BP Chemicals LimitedInventors: Simon James Kitchen, Daiyi Qin
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Patent number: 6376706Abstract: A catalyst for use in the production of vinyl acetate which comprises (1) a catalyst support, (2) palladium, (3) an acid, (4) at least one acetic acid catalyst promoter and (5) at least one vinyl acetate promoter and/or co-promoter. A process for the production of vinyl acetate from ethylene and an oxygen-containing gas using the catalyst.Type: GrantFiled: May 21, 1999Date of Patent: April 23, 2002Assignee: BP Chemical Ltd.Inventors: Simon James Kitchen, Daiyi Qin
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Patent number: 6350901Abstract: In a process for production of vinyl acetate in which ethylene, liquid acetic acid and an oxygen-containing gas are fed to a fluid bed reactor containing a catalyst comprising a Group VIII metal, a promoter and a co-promoter, stickiness of the catalyst is reduced by limiting the amount of co-promoter to up to 6% by weight of the catalyst.Type: GrantFiled: July 29, 1999Date of Patent: February 26, 2002Assignee: BP Chemicals LimitedInventors: Simon James Kitchen, George Frederick Salem, Bruce Leo Williams
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Patent number: 6350900Abstract: A catalyst for the production of vinyl acetate by reaction of ethylene, oxygen and acetic acid comprising a porous support on the porous surfaces of which is deposited catalytically effective amounts of metallic palladium and gold, said catalyst having been prepared by steps comprising impregnating a porous support, the porous surfaces of which contain a catalytically effective amount of a prereduced metallic palladium, with a solution of potassium aurate, and reducing the potassium aurate to a catalytically effective amount of metallic gold. Alternate embodiments are also disclosed.Type: GrantFiled: June 2, 1998Date of Patent: February 26, 2002Assignee: Celanese International CorporationInventors: Tao Wang, Jerry A. Broussard
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Publication number: 20020013220Abstract: A catalyst for the production of vinyl acetate by reaction of ethylene, oxygen and acetic acid comprising a porous support on the porous surfaces of which is deposited catalytically effective amounts of metallic palladium and gold, said catalyst having been prepared by steps comprising impregnating a porous support, the porous surfaces of which contain a catalytically effective amount of a prereduced metallic palladium, with a solution of potassium aurate, and reducing the potassium aurate to a catalytically effective amount of metallic gold. Alternate embodiments are also disclosed.Type: ApplicationFiled: August 20, 2001Publication date: January 31, 2002Inventors: Tao Wang, Jerry A. Broussard
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Patent number: 6342628Abstract: In a process for production of vinyl acetate by the reaction of ethylene, acetic acid and oxygen, ethylene is recovered from the gases withdrawn from the reactor and recycled such that the amount of ethylene in the combined feed to the reactor is at least 60 mol %.Type: GrantFiled: July 29, 1999Date of Patent: January 29, 2002Assignee: BP Chemicals LimitedInventors: Bruce Leo Williams, Robert William Clarke, Timothy Crispin Bristow, Michael James Baker
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Patent number: 6333444Abstract: A catalyst composition and its use for the oxidation of ethane to ethylene and/or acetic acid and/or for the oxidation of ethylene to acetic acid which comprises in combination with oxygen the elements molybdenum, vanadium, niobium and gold in the absence of palladium according to the empirical formula: MOaWbAucVdNbeYf (I) wherein Y is one or more elements selected from the group consisting of: Cr, Mn, Ta, Ti, B, Al, Ga, In, Pt, Zn, Cd, Bi, Ce, Co, Rh, Ir, Cu, Ag, Fe, Ru, Os, K, Rb, Cs, Mg, Ca, Sr, Ba, Zr, Hf, Ni, P, Pb, Sb, Si, Sn, Tl, U, Re, Te, La and Pd; a, b, c, d, e and f represent the gram atom ratios of the elements such that: 0<a≦1; 0≦b<1 and a+b=1; 10−5<c≦0.02; 0<d<2; 0<e≦1; and 0≦f≦2.Type: GrantFiled: February 17, 2000Date of Patent: December 25, 2001Assignee: BP Chemicals LimitedInventors: Brian Ellis, Michael David Jones
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Patent number: 6303536Abstract: This invention relates to a preparation process of a catalyst which comprises a noble metal and a metal as catalysis promoter in combination with an alkali or alkaline earth metal compound, supported on the outer surface of a carrier. The preparation process comprises impregnating the carrier with a solution containing an oxidative state noble metal as the main catalyst and an oxidative state metal as catalysis promoter, reducing the oxidative state metals into the metallic state in gaseous phase with a gaseous reducing agent under certain temperature, pressure, moisture and gas concentration, then impregnating the reduced carrier with a solution of an alkali or alkaline earth metal compound. The metal components-supporting catalyst prepared by the process according to the present invention has a high surface area and exhibits high catalytic activity, which leads to increase the catalytic efficiency and life of this heterogeneous catalyst.Type: GrantFiled: August 16, 1999Date of Patent: October 16, 2001Assignee: Dairen Chemical CoorporationInventors: Shien-Chang Chen, Fu-Shen Lin, Yuh-Lih Jong, Pi-Fwu Jang
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Publication number: 20010018401Abstract: A process for the preparation of a fluid bed vinyl acetate (VAM) catalyst comprising impregnating a support comprising a mixture of substantially inert microspheroidal particles with a solution comprising a metal salt of Pd and M, wherein M comprises Ba, Cd, Au, La, Nb, Ce, Zn, Pb, Ca, Sr, Sb or mixtures thereof, reducing the metal salts to form a deposit of Pd and M on the support surface and impregnating the support with at least one alkali metal salt. At least 50% of the particles used for the microspheroidal support have a particle size below 105 microns.Type: ApplicationFiled: June 30, 1999Publication date: August 30, 2001Inventors: PATRICIA RAE BLUM, LARRY MICHAEL CIRJAK, MARC ANTHONY PEPERA, CHRISTOS PAPARIZOS, GEORGE FREDERICK SALEM, MICHAEL JAMES BAKER