Hydrogenation Of Diolefin Or Triple Bond Patents (Class 585/259)
  • Patent number: 7525000
    Abstract: The present invention provides a method and apparatus for removing acetylene from a gasoeus mixture comprising hydrogen, methane, ethane, ethylene, acetylene, propane, propylene, butane, butenes, butadiene, and other C4 or higher hydrocarbons. The method of the invention utilizes a front-end acetylene removal unit (“ARU”) located after a charge gas compressor in which acetylene is selectively reduced. The method of the invention achieves selective reduction of acetylene by using a proprietary Chevron Phillips E series palladium based catalyst. The method of the invention also utilizes a novel startup procedure, a novel emergency shutdown procedure, a novel maximum cool down procedure, and a novel carbon monoxide monitoring procedure.
    Type: Grant
    Filed: March 23, 2005
    Date of Patent: April 28, 2009
    Assignee: Eastman Chemical Company
    Inventors: James M. Jordan, Kevin H. McGuire, Daryl Bitting, George M. McLeod, Randall L. Lamirand, James J. Cerrato, Ronnie P. Pertuit
  • Patent number: 7462277
    Abstract: In a continuous process for fractionating a C4 fraction (C4) by extractive distillation using a selective solvent (LM) in an extractive distillation column (EDK), it is proposed that a dividing wall (TW) is installed in the longitudinal direction in the extractive distillation column (EDK) to form a first region (A), a second region (B) and a lower combined column region (C) and a top stream (C4H10) comprising the butanes is taken off from the first region (A), a top stream (C4H8) comprising the butenes is taken off from the second region (B) and a stream (C4H6) comprising the hydrocarbons from the C4 fraction which are more soluble in the selective solvent (LM) than are the butanes and the butenes is taken off from the lower combined column region (C).
    Type: Grant
    Filed: July 22, 2003
    Date of Patent: December 9, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Till Adrian, Thomas Hill, Klaus Kindler, Bernd Heida
  • Patent number: 7462751
    Abstract: A selective hydrogenation catalyst composition comprises a support; a first metal component comprising rhodium; and a second metal component comprising a metal other than rhodium and selected from Groups 1 to 15 of the Periodic Table of Elements, wherein said first and second components are predominantly contained in an outer surface layer of the support having a depth of not more than 1000 microns.
    Type: Grant
    Filed: August 26, 2005
    Date of Patent: December 9, 2008
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: David M. Lowe, Michel Molinier, John D. Y. Ou, Michael A. Risch, Anthony F. Volpe, Jr., Jeffrey C. Yoder, Valery Sokolovskii
  • Patent number: 7459593
    Abstract: Disclosed is a process for integrating a butene dimerization process with a metathesis process to remove isobutene from the feed stream to the metathesis reactor. The isobutene is preferentially dimerized in the dimerization process to leave n-butenes for metathesis with ethylene. An upstream selective hydrogenation process also isomerizes 1-butenes to 2-butenes which is the preferred butene reagent in the metathesis process. A common fractionator column for the dimerization and hydrogenation processes is also described.
    Type: Grant
    Filed: November 18, 2005
    Date of Patent: December 2, 2008
    Assignee: UOP LLC
    Inventors: Steven L. Krupa, Jill M. Meister
  • Patent number: 7453017
    Abstract: The present invention describes a Pd-catalyst which further contains La, Ti, Nb, K or Si. The Pd-catalyst has a high ethylene selectivity even after a low temperature reduction in the selective hydrogenation of acetylene to ethylene. The invention also relates to the production of the catalyst. A catalyst of the invention consists essentially of 0.05 to 2.0% by weight, based on the supported catalyst, of palladium and one or two metals chosen form the group consisting of lanthanum, niobium, titanium, potassium and silicon. The catalyst can be prepared by the following procedure. (1) Impregnating a support in aqueous solution of tetra amine palladium hydroxide, followed by drying and calcination; (2) The second and, if necessary, a third metal is impregnated by impregnating the Pd-catalyst in the solution of the metal precursor followed by drying and calcination; (3) The catalyst according to step (2) is then reduced in hydrogen at 200° C. to 600° C. for 1 to 5 hours.
    Type: Grant
    Filed: March 26, 2004
    Date of Patent: November 18, 2008
    Assignee: BASF AG
    Inventors: Sang Heup Moon, Woo Jae Kim, Jung Hwa Kang, In Young Ahn
  • Patent number: 7453016
    Abstract: A selective hydrogenation process and a layered catalyst composition for use in the selective hydrogenation process are disclosed. The process is useful for the selective hydrogenation of diolefins having from about 8 to about 19 carbon atoms per molecule to monoolefins.
    Type: Grant
    Filed: December 20, 2005
    Date of Patent: November 18, 2008
    Assignee: UOP LLC
    Inventor: Gregory J. Gajda
  • Patent number: 7432407
    Abstract: The invention relates to a process by which C4- to C6-olefins or an essentially sulfur-free olefin cut comprising C4- to C6-olefins is isomerized over a catalyst comprising an element of the eighth transition group of the Periodic Table, in the presence of at least one added sulfur compound, and any polyunsaturated hydrocarbons contained therein are selectively hydrogenated and hydroisomerized, and also the sulfur compounds are separated from the product and optionally recycled, so that virtually sulfur-free products are obtained.
    Type: Grant
    Filed: September 20, 2002
    Date of Patent: October 7, 2008
    Assignee: OXENO Olefinchemie GmbH
    Inventors: Andreas Beckmann, Armin Rix, Udo Knippenberg, Franz Nierlich, Wilfried Bueschken, Ralf Duessel
  • Patent number: 7408091
    Abstract: A process and catalyst for the liquid phase selective hydrogenation of alkynes to alkenes with high selectivity to alkenes relative to alkanes, high alkyne conversion, and sustained catalytic activity comprising a reactant comprising an alkyne and a non-hydrocarbon solvent/absorbent, contacting the reactant stream with a hydrogen-containing stream in the presence of a supported, promoted, Group VIII catalyst, removing the solvent/absorbent, and recovering the alkene product.
    Type: Grant
    Filed: May 15, 2006
    Date of Patent: August 5, 2008
    Assignee: Synfuels International, Inc.
    Inventors: Marvin M. Johnson, Edward R. Peterson, Sean C. Gattis
  • Patent number: 7408089
    Abstract: More selective and efficient Ni hydrotreating catalysts are those which contain more than about 60% of the Ni content on the peripheral surface of porous supports, such as extruded alumina, which may be obtained by spraying an atomized solution of a Ni compound onto the support and drying it at a temperature in the range of from 200 to 600° C. When used, for example, to remove acetylenic compounds from butadiene streams, higher recovery of the desired butadiene with lower acetylenic content and low heavy polymer deposition is obtained than was possible with prior catalysts.
    Type: Grant
    Filed: April 21, 2004
    Date of Patent: August 5, 2008
    Assignee: Catalytic Distillation Technologies
    Inventor: J. Yong Ryu
  • Patent number: 7408090
    Abstract: Acetylenes and dienes in a stream containing hydrogen, methane, C2-C6 olefins and paraffins, C2-C6 acetylenes and dienes, benzene, toluene, xylenes, and other C6+ components are hydrogenated in a downflow boiling point reactor wherein the heat of reaction is absorbed by the liquid in the reactor which produces a vapor. Besides the feed to the reactor there is a recirculating stream which is fed at a rate sufficient to ensure that the catalyst particles within the reactor are wetted. A third stream, which is provided from a second downstream liquid/vapor separator from partially condensed vapor from the first downstream liquid/vapor separator corresponding to the mass evaporated in the reactor, is fed to the reactor. The composition of the third stream controls the steady state composition of the liquid flowing through the reactor.
    Type: Grant
    Filed: April 7, 2005
    Date of Patent: August 5, 2008
    Assignee: Catalytic Distillation Technologies
    Inventors: Lawrence A. Smith, Jr., Abraham P. Gelbein
  • Patent number: 7390933
    Abstract: In a process for reducing the Bromine Index of a feed containing a linear alkylbenzene and bromine-reactive olefinic hydrocarbon contaminants, the feed is contacted under conditions effective to remove bromine-reactive olefinic hydrocarbon contaminants with a catalyst comprising zeolite Y catalyst having an alpha value of about 2 to about 30. The feed will normally also contain benzene and linear paraffin remaining from the alkylation process used to produce the linear alkylbenzene.
    Type: Grant
    Filed: March 29, 2007
    Date of Patent: June 24, 2008
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Frederick Y. Lo, David L. Stern, Ronald J. Cimini, James L. Propp
  • Patent number: 7385097
    Abstract: A process for the purification of a diolefin hydrocarbon stream containing acetylene and sulfur compounds.
    Type: Grant
    Filed: June 29, 2005
    Date of Patent: June 10, 2008
    Assignee: UOP LLC
    Inventor: Paul R. Cottrell
  • Patent number: 7374667
    Abstract: For the production of gasoline with a low sulfur content, a process comprises at least one stage for transformation of sulfur-containing compounds consisting of an alkylation or adsorption of sulfur-containing compounds and/or an increasing of the weight of light sulfur-containing compounds, at least one stage for treatment in the presence of an acid catalyst and at least one desulfurization treatment of at least a portion of the gasoline. The process can also optionally comprise at least one stage for selective hydrogenation of diolefins and optionally at least one fractionation of the gasoline that is obtained into at least two fractions: light gasoline and heavy gasoline.
    Type: Grant
    Filed: March 12, 2002
    Date of Patent: May 20, 2008
    Assignees: BP Corporation North America, Inc., Institute Francais du Petrole
    Inventors: Quentin Debuisschert, Denis Uzio, Jean-Luc Nocca, Florent Picard, David B Arnett, Mike Grayson, Donald E Zeek, Carl Snider
  • Patent number: 7368625
    Abstract: A catalyst or precursor thereto comprising cobalt and/or a cobalt compound on a transition alumina support having a total cobalt content of at least 41% by weight and a cobalt surface area, after reduction, greater than 25 m2 per gram of total cobalt. The catalyst or precursor may be made by slurrying a transition alumina powder having a pore volume of at least 0.7 ml/g with an aqueous cobalt ammine carbonate complex and heating the slurry to decompose the complex.
    Type: Grant
    Filed: June 28, 2005
    Date of Patent: May 6, 2008
    Assignee: Johnson Matthey PLC
    Inventors: Martinus G. Lok, Gordon J. Kelly, Gavin Gray
  • Patent number: 7368617
    Abstract: Acetylenes and dienes in a stream containing hydrogen, methane, C2-C6 olefins and paraffins, C2-C6 acetylenes and dienes, benzene, toluene, xylenes, and other C6+ components are hydrogenated in a downflow boiling point reactor wherein the heat of reaction is absorbed by the liquid in the reactor which produces a vapor. Besides the feed to the reactor there is a recirculating stream which is fed at a rate sufficient to ensure that the catalyst particles within the reactor are wetted. A third stream, which is taken from a downstream distillation column, is fed to provide the make up mass corresponding to the mass evaporated in the reactor. The composition of the this third stream controls the steady state composition of the liquid flowing through the reactor.
    Type: Grant
    Filed: November 8, 2004
    Date of Patent: May 6, 2008
    Assignee: Catalytic Distillation Technologies
    Inventors: Abraham P. Gelbein, Lawrence A. Smith, Jr.
  • Patent number: 7351327
    Abstract: A process for concurrently fractionating and treating a full range naphtha stream. The full boiling range naphtha stream is first subjected to simultaneous thioetherification and splitting into a light boiling range naphtha, an intermediate boiling range naphtha and a heavy boiling range naphtha. The intermediate boiling range naphtha containing thiophene and thiophene boiling range mercaptans is passed on to a polishing hydrodesulfurization reactor where a low sulfur, low olefin gas oil is concurrently fed to the polishing reactor to insure that a liquid phase is present.
    Type: Grant
    Filed: April 7, 2004
    Date of Patent: April 1, 2008
    Assignee: Catalytic Distillation Technologies
    Inventors: Gary G. Podrebarac, Willibrord A. Groten, Lawrence A. Smith, Jr.
  • Patent number: 7301062
    Abstract: A process for the selective hydrogenation of one or more alkyne and/or one or more diene in an olefin-containing hydrocarbon feed includes contacting the hydrocarbon feed with a catalyst under selective hydrogenation conditions, the catalyst including from about 0.01 to about 0.1 weight percent palladium and from about 0.005 to about 0.6 weight percent of at least one Group IB metal incorporated into an inorganic support, wherein the surface area of the support is from about 2 to about 20 m2/g, the pore volume is greater than about 0.4 cc/g, at least about 90% of the pore volume is contained in pores with pore diameters larger than about 500 ?, and the pore volume of the pores with a pore diameter from about 500 to about 1,000 ? comprise from about 1% to about 2% of the total pore volume.
    Type: Grant
    Filed: July 27, 2004
    Date of Patent: November 27, 2007
    Assignee: ABB Lummus Global Inc.
    Inventors: Robert J. Gartside, Thomas Skourlis
  • Patent number: 7297824
    Abstract: Improved Ni catalysts for hydrogenation reactions are disclosed. The catalysts are useful for hydrogenation such as selective hydrogenation of acetylenic impurities in crude olefin and diolefin streams. The catalysts are prepared by depositing nickel on a porous support which has the following specific physical properties; BET surface area of from 30 to about 100 m2/g, total nitrogen pore volume of from 0.4 to about 0.9 cc/g, and an average pore diameter of from about 110 to 450 ? with or without modifiers of one or more elements selected from the group consisting of Cu, Re, Pd, Zn, Mg, Mo, Ca and Bi.
    Type: Grant
    Filed: June 30, 2005
    Date of Patent: November 20, 2007
    Assignee: Catalytic Distillation Tehnologies
    Inventors: J. Yong Ryu, Hugh M. Putman
  • Patent number: 7288686
    Abstract: A supported hydrogenation catalyst comprising (1)Pd or a Group 8 metal comprising Pd and one other Group 8 metal, preferably a Group 8 metal selected from Pt, Ir, Ru, Co or Ni, and (2) at least two metals selected from Ag, Zn or Bi, preferably Ag and at least one of Zn or Bi. Optionally the catalyst may contain K. The catalyst is supported on a porous support such as a silica, alumina, silica-alumina or carbon. The preferred supports have an average pre diameter of 180 ? with no pores smaller than 35 ?, total pore volume larger than 0.65 cc/g and preferably less than about 100 m2/g BET surface area. The catalysts are useful for the hydrogenation of unsaturated hydrocarbons such as acetylenes and diolefins in various mixed olefin streams.
    Type: Grant
    Filed: August 5, 2004
    Date of Patent: October 30, 2007
    Assignee: Catalytic Distillation Technologies
    Inventor: J. Yong Ryu
  • Patent number: 7253329
    Abstract: A process for preparing cyclododecene by selective gas-phase hydrogenation of at least one starting material selected from cyclododecatriene, cyclododecadiene and mixtures thereof, wherein the starting material present in the gas phase is hydrogenated in the presence of a catalyst in a fixed-bed reactor and the Bodenstein number for the process is greater than 100.
    Type: Grant
    Filed: March 2, 2004
    Date of Patent: August 7, 2007
    Assignee: Degussa AG
    Inventors: Juergen Herwig, Norbert Wilczok, Martin Roos, Rudolf Burghardt, Johann Gaube, Georg Oenbrink, Bernd Guenzel
  • Patent number: 7250544
    Abstract: A process for selective hydrogenation of polyunsaturated compounds that are contained in a hydrocarbon feedstock in the presence of a catalytic reactor with a hydrogen-selective membrane comprises a) the introduction of said feedstock co-mixed with a first amount hydrogen into a reaction zone of said reactor, b) the contact of a second amount hydrogen with the upstream face of the membrane, which is inorganic and porous, then c) the catalytic reaction of the feedstock with hydrogen that has selectively traversed the membrane.
    Type: Grant
    Filed: February 2, 2004
    Date of Patent: July 31, 2007
    Assignee: Institut Francais du Petrole
    Inventors: Christophe Chau, Denis Uzio
  • Patent number: 7227047
    Abstract: A process is disclosed for selectively removing isobutene and butadiene from a stream, the process comprising contacting the stream with a hydrogenation catalyst to hydrogenate butadiene and an oligomerization catalyst to oligomerize isobutene.
    Type: Grant
    Filed: August 22, 2003
    Date of Patent: June 5, 2007
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Michael A Risch, John Di-Yi Ou, Cor F. Van Egmond
  • Patent number: 7208646
    Abstract: A process for the selective hydrogenation of dienes in mixed streams of olefin containing hydrocarbons, such as butadiene in a mixed C4 stream with minimum loss of monoolefins is disclosed wherein the reactor is operated at conditions which induce pulse flow. The pulse flow is induced in a downflow boiling point reactor by vaporization of a portion of the liquid feed at proper conditions.
    Type: Grant
    Filed: August 25, 2004
    Date of Patent: April 24, 2007
    Assignee: Catalytic Distillation Technologies
    Inventor: Christopher C. Boyer
  • Patent number: 7141709
    Abstract: In some embodiments, methods of producing monoolefins include contacting an olefin stream with a polar solvent to extract a highly unsaturated hydrocarbon from the olefin stream, followed by contacting the polar solvent with a hydrogenation catalyst in the presence of hydrogen at conditions effective to hydrogenate the highly unsaturated hydrocarbon to a monoolefin. The monoolefin then desorbs from the polar solvent and enters the purified olefin stream, allowing the polar solvent to be recycled. In other embodiments, monoolefin production systems include an extraction-hydrogenation zone for performing the extraction and hydrogenating steps in situ. In alternative embodiments, the hydrogenation zone is disposed downstream from the extraction zone.
    Type: Grant
    Filed: November 13, 2003
    Date of Patent: November 28, 2006
    Assignee: Chevron Phillips Chemical Company LP
    Inventors: Tin-Tack Peter Cheung, Marvin M. Johnson
  • Patent number: 7115789
    Abstract: The present invention is a process for removing alkynes and/or dienes from an olefin product stream withdrawn from an oxygenate-to-olefins reactor. The process comprises hydrogenating a first olefin stream that has alkynes and/or dienes in the presence of excess hydrogen and a first hydrogenation catalyst. The hydrogenation of the first olefin stream produces a second olefin stream that has unreacted hydrogen. The second olefin stream is contacted with a second hydrogenation catalyst producing a third olefin stream. The third olefin stream has low levels of hydrogen and alkynes and/or dienes.
    Type: Grant
    Filed: March 28, 2003
    Date of Patent: October 3, 2006
    Assignee: Exxon Mobil Chemical Patents Inc.
    Inventors: Keith Holroyd Kuechler, David R. Lumgair, Jr.
  • Patent number: 7105711
    Abstract: A process for the reduction of a phenylacetylene contaminant in the presence of a styrene monomer. A styrene monomer stream containing a minor amount of phenylacetylene is supplied to a hydrogenation reactor. A hydrogenation gas comprising hydrogen is also supplied to the hydrogenation reactor. The styrene monomer stream and the hydrogen are brought into contact with a catalyst bed containing a catalyst comprising a reduced copper compound on a theta alumina support. The hydrogenation reactor is operated at a temperature of at least 60° C. and a pressure of at least 30 psig to hydrogenate phenylacetylene to styrene. A product is recovered from the hydrogenation reactor having a substantially reduced phenylacetylene content and an enhanced styrene content. The hydrogenation gas comprises a mixture of nitrogen and hydrogen.
    Type: Grant
    Filed: July 31, 2003
    Date of Patent: September 12, 2006
    Assignee: Fina Technology, Inc.
    Inventor: James T. Merrill
  • Patent number: 7090766
    Abstract: A process wherein all of the unsaturates within a cracked naphtha stream are substantially hydrogenated to alkanes and the olefin depleted stream is then subjected to hydrodesulfurization to achieve the desired sulfur levels without the formation of recombinant mercaptans.
    Type: Grant
    Filed: September 30, 2002
    Date of Patent: August 15, 2006
    Inventors: Kenneth H. Johnson, Richard L. Moseley
  • Patent number: 7087155
    Abstract: A process for cracking an olefin-rich hydrocarbon feedstock which is selective towards light olefins in the effluent, the process comprising contacting a hydrocarbon feedstock containing olefins having a first composition of at least one olefinic component with a crystalline silicate catalyst to produce an effluent having a second composition of at least one olefinic component, the feedstock and the effluent having substantially the same olefin content by weight therein as the feedstock. A process for the cracking of olefins in a hydrocarbon feedstock containing at least one diene and at least one olefin, the process comprising hydrogenating the at least one diene to form at least one olefin in the presence of a transition metal-based hydrogenation catalyst at an inlet temperature of from 40 to 200° C.
    Type: Grant
    Filed: December 5, 1998
    Date of Patent: August 8, 2006
    Assignee: TOTAL Petrochemicals Research Feluy
    Inventors: Jean-Pierre Dath, Luc Delorme, Jacques-François Grootjans, Xavier Vanhaeren, Walter Vermeiren
  • Patent number: 7078577
    Abstract: A method for forming dihydroDicyclopentadiene comprises mixing a source of dicyclopentadiene with at least one solvent and at least one reactive component in the presence of a source of hydrogen and a selective hydrogenation catalyst, the solvent and reactive component being readily separable from dihydroDicyclopentadiene, and the reactive component and catalyst favoring the formation of dihydroDicyclopentadiene over tetra hydro dicyclopentadiene.
    Type: Grant
    Filed: August 11, 2003
    Date of Patent: July 18, 2006
    Assignee: Equistar Chemicals, LP
    Inventor: Kenneth M. Webber
  • Patent number: 7074971
    Abstract: The present invention provides new highly-efficient separation processes and systems for separating polymerization-grade ethylene and propylene from an initial effluent stream comprising ethane, ethylene, propylene, dimethyl ether, and one or more of propane, acetylene, methyl acetylene, propadiene, methane, hydrogen, carbon monoxide, carbon dioxide and C4+ components. In one embodiment, the initial effluent stream is provided from a methanol-to-olefin reaction system. It has been discovered that the best separation of these components is realized when DME is selectively removed in a first separation step, followed by separation of the remaining components in additional separation steps.
    Type: Grant
    Filed: March 6, 2003
    Date of Patent: July 11, 2006
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Cor F. Van Egmond, Jeffrey L. Brinen
  • Patent number: 7070690
    Abstract: The invention relates to a process for conversion of hydrocarbons in the presence of at least one catalyst with controlled acidity, characterized in that the level of activity of said catalyst in isomerization of the cyclohexane is less than 0.10 and/or in that the ratio of toluene hydrogenation activity to the cyclohexane isomerization activity is greater than 10.
    Type: Grant
    Filed: February 24, 2003
    Date of Patent: July 4, 2006
    Assignee: Institut Francais du Petrole
    Inventors: Virginie Harle, Stéphane Kressmann, Isabelle Guibard, Slavik Kasztelan, Frédéric Morel
  • Patent number: 7045669
    Abstract: The charge gas from the thermal cracking of a hydrocarbon feedstock is processed in a front-end catalytic distillation hydrogenation system of an olefins plant to more effectively recover ethylene and propylene product and to process the by-products. The rate of fouling in the system is reduced by employing two columns in the system with the first column operating at a higher pressure and the second column operating at a lower pressure. The hydrogenation as well as fractionation takes place in the first column while the second column is only a fractionator. The temperature of the bottoms from each column is maintained at a temperature less than 200° C. to avoid fouling.
    Type: Grant
    Filed: August 5, 2003
    Date of Patent: May 16, 2006
    Assignee: Catalytic Distillation Technologies
    Inventors: Charles Sumner, Jeffrey L. Heineman, Christopher A. Di Biase
  • Patent number: 7045670
    Abstract: A process for the liquid phase selective hydrogenation of alkynes to alkenes with high selectivity to alkenes relative to alkanes, high alkyne conversion, and sustained catalytic activity comprising a reactant comprising an alkyne and a non-hydrocarbon solvent/absorbent, contacting the reactant stream with a hydrogen-containing stream in the presence of a supported, promoted, Group VIII catalyst, removing the solvent/absorbent, and recovering the alkene product.
    Type: Grant
    Filed: December 4, 2003
    Date of Patent: May 16, 2006
    Assignee: Synfuels International, Inc.
    Inventors: Marvin M. Johnson, Edward R. Peterson, Sean C. Gattis
  • Patent number: 7041860
    Abstract: An improved selective hydrogenation process for removing acetylenic impurities such as vinyl acetylene, ethyl acetylene, propyl acetylene and acetylene in a steam cracked crude butadiene stream by selective hydrogenation is carried out in two steps. In the first step, the partial selective hydrogenation is carried out in a fixed bed with a copper based catalyst to have the ratio of vinyl acetylene to ethyl acetylene in a range of from 0 to about 1, preferably from about 0.01 to 0.6, in the product stream. In the second step, the selective hydrogenation of the remaining C4 acetylenic impurities is carried out to completion in the catalytic distillation mode using a palladium promoted copper catalyst, an improved palladium catalyst or a combination of these two.
    Type: Grant
    Filed: October 6, 2003
    Date of Patent: May 9, 2006
    Assignee: Catalytic Distillation Technologies
    Inventor: J. Yong Ryu
  • Patent number: 7038097
    Abstract: It has been discovered that a dual bed process using two different catalysts for the selective hydrogenation of acetylene and/or methyl acetylene (MA) and/or propadiene (PD) in a light olefin-rich feedstream can be accomplished with less selectivity to making oligomers (green oil) as compared with existing commercial technologies, if a low oligomers selectivity catalyst is used first in the process. A palladium catalyst may be used as a second, sequential catalyst to further hydrogenate acetylene and/or MAPD while consuming at least a portion of the balance of the hydrogen present. The first catalyst should be different from the second catalyst.
    Type: Grant
    Filed: March 4, 2003
    Date of Patent: May 2, 2006
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Michel Molinier, John Di-Yi Ou, Michael A. Risch, John Scott Buchanan
  • Patent number: 7038096
    Abstract: A process of treating a catalyst composition containing palladium, an inorganic support, and a catalyst component, such as silver and/or a modifier such as alkali metal fluoride, is provided. The process involves contacting a catalyst composition with a first treating agent comprising carbon monoxide under a first treating condition to provide a treated catalyst composition. As an option, such treated catalyst composition can then be contacted with a second treating agent comprising a hydrogen-containing fluid under a second treating condition. The treated catalyst composition can be used in a selective hydrogenation process in which highly unsaturated hydrocarbons such as diolefins and/or alkynes are contacted with such treated catalyst composition in the presence of hydrogen to produce less unsaturated hydrocarbons such as monoolefins.
    Type: Grant
    Filed: April 7, 2004
    Date of Patent: May 2, 2006
    Assignee: Chevron Phillips Chemical Company LP
    Inventors: Tin-Tack Peter Cheung, Joseph J. Bergmeister, Marvin M. Johnson
  • Patent number: 7025872
    Abstract: Process for obtaining a hydrocarbon fraction that can be used as a feedstock of an etherification unit and that contains a small amount of diene compounds, nitrogen-containing compounds and sulfur-containing compounds, starting from an initial hydrocarbon feedstock that comprises a mixture of olefins, dienes, and nitrites as well as sulfur-containing compounds, whereby said process comprises at least the following successive stages: a) a selective hydrogenation of said initial hydrocarbon feedstock in the presence of a catalyst of group VIII of the periodic table, b) a fractionation by distillation of the effluents that are obtained from stage a) under conditions that make it possible to obtain at least two fractions including said hydrocarbon fraction and that comprises a small amount of diene compounds, nitrogen-containing compounds and sulfur-containing compounds, and a heavy fraction that contains heavy hydrocarbons and the majority of the nitrogen-containing compounds and sulfur-containing compounds
    Type: Grant
    Filed: January 22, 2004
    Date of Patent: April 11, 2006
    Assignee: Institut Francais du Petrole
    Inventors: Florent Picard, Alain Forestiere, Julia Magne-Drisch, Nathalie Marchal-George
  • Patent number: 7014750
    Abstract: Systems and processes for the hydrotreatment of pyrolysis gasoline comprising reactors, monolithic catalyst beds and hydrogen-containing treatment gases that allow for improved efficiency and productivity over conventional trickle bed processes and systems for such hydrotreatment.
    Type: Grant
    Filed: August 5, 2004
    Date of Patent: March 21, 2006
    Assignee: Corning Incorporated
    Inventors: Thorsten R. Boger, Shantanu Roy, Charles M. Sorensen, Jr.
  • Patent number: 7009085
    Abstract: A catalyst composition comprising an inorganic support material, a palladium component, a silver component, and a promoter component having the formula XYFn, wherein X is an alkaline metal, Y is an element selected from the group consisting of antimony, phosphorus, boron, aluminum, gallium, indium, thallium, and arsenic, and n is an integer which makes YFn a monovalent anion. The above-described catalyst is employed as a catalyst in the selective hydrogenation of acetylene. The above-described catalyst is made by incorporating a palladium component, a silver component, and a promoter component into an inorganic support material.
    Type: Grant
    Filed: July 1, 2002
    Date of Patent: March 7, 2006
    Assignee: Phillips Petroleum Company
    Inventor: Tin-Tack Peter Cheung
  • Patent number: 6977317
    Abstract: A process for the selective hydrogenation of olefins contained in a hydrocarbonaceous feedstock comprising olefins and aromatic compounds.
    Type: Grant
    Filed: June 25, 2002
    Date of Patent: December 20, 2005
    Assignee: UOP LLC
    Inventors: Stanley J. Frey, Richard E. Marinangeli
  • Patent number: 6949686
    Abstract: A method for stabilizing pyrolysis gasoline by hydrogenating same over a Group VIII metal catalyst wherein the catalyst is promoted against poisoning by at least one metal from Groups I B, VI B, VII B, and zinc. Poisons preferentially bind with the promoters and not with the active catalytic metals.
    Type: Grant
    Filed: May 30, 2002
    Date of Patent: September 27, 2005
    Assignee: Equistar Chemicals, LP
    Inventor: Mark P. Kaminsky
  • Patent number: 6867338
    Abstract: Acetylenes and dienes in a stream containing hydrogen, methane, C2-C6 olefins and paraffins, C2-C6 acetylenes and dienes, benzene, toluene, xylenes, and other C6+ components are hydrogenated in a downflow boiling point reactor wherein the heat of reaction is absorbed by the liquid in the reactor which produces a vapor. Besides the feed to the reactor there is a recirculating stream which is fed at a rate sufficient to ensure that the catalyst particles within the reactor are wetted. A third stream, which is taken from a downstream distillation column, is fed to provide the make up mass corresponding to the mass evaporated in the reactor. The composition of the this third stream controls the steady state composition of the liquid flowing through the reactor.
    Type: Grant
    Filed: March 12, 2003
    Date of Patent: March 15, 2005
    Assignee: Catalytic Distillation Technologies
    Inventors: Abraham P. Gelbein, Lawrence A. Smith, Jr.
  • Publication number: 20040267034
    Abstract: Disclosed are heterogeneous processes (i) for the hydrogenation of a compound containing at least one unsaturated carbon-carbon bond, and (ii) for the hydro-dehalogenation of a compound containing at least one C—Cl, C—Br or C—I bond. The processes comprise reacting said compound with a hydrogenating agent and a heterogeneous hydrogenation catalyst in the presence of an ionic liquid.
    Type: Application
    Filed: July 30, 2004
    Publication date: December 30, 2004
    Inventors: Kris Anderson, Peter Goodrich, Christopher Hardacre, Sarah Elizabeth Jane McMath
  • Publication number: 20040260131
    Abstract: This invention relates to acetylene removal catalysts and their use in the hydrogenating of highly unsaturated hydrocarbons to less unsaturated hydrocarbons in an olefin rich hydrocarbon stream in the presence of hydrogen and a catalyst composition under conditions effective to convert said highly unsaturated hydrocarbon to a less unsaturated hydrocarbon. Said catalyst composition comprises palladium, silver, potassium, and an inorganic support material, wherein the catalyst composition contains less than about 0.3 weight % potassium. In the presence of sulfur-containing impurities, the catalysts of the present invention yield a much smaller increase in T1 (cleanup temperature) and higher ethylene selectivity is achieved.
    Type: Application
    Filed: June 23, 2003
    Publication date: December 23, 2004
    Applicant: Chevron Phillips Chemical Company ("CPCHEM")
    Inventors: Joseph J. Bergmeister, Gary A. Delzer, Tin-Tack P. Cheung
  • Patent number: 6830678
    Abstract: The invention relates to a process of producing gasoline with a low sulphur content from a feedstock containing sulphur. This process comprises at least one step a1 of selectively hydrogenating the diolefins and acetylenic compounds, at least one separation of the gasoline (step b) obtained at step a1 into at least three fractions, at least one step c1 of treating the heavy gasoline separated at step b on a catalyst enabling the unsaturated sulphur compounds to be at least partially decomposed or hydrogenated and at least one step d to remove the sulphur and nitrogen from at least one intermediate fraction, followed by catalytic reforming.
    Type: Grant
    Filed: March 29, 2001
    Date of Patent: December 14, 2004
    Assignee: Institut Francais DuPetrole
    Inventors: Blaise Didillon, Denis Uzio, Quentin Debuisschert, Jean-Luc Nocca
  • Patent number: 6824676
    Abstract: A process for concurrently fractionating and treating a full range naphtha stream. The full boiling range naphtha stream is first subjected to simultaneous thioetherification and splitting into a light boiling range naphtha, an intermediate boiling range naphtha and a heavy boiling range naphtha. The intermediate boiling range naphtha containing thiophene and thiophene boiling range mercaptans is passed on to a polishing hydrodesulfurization reactor where a low sulfur, low olefin gas oil is concurrently fed to the polishing reactor to insure that a liquid phase is present.
    Type: Grant
    Filed: March 8, 2002
    Date of Patent: November 30, 2004
    Assignee: Catalytic Distillation Technologies
    Inventors: Gary G. Podrebarac, Willibrord A. Groten, Lawrence A. Smith, Jr.
  • Patent number: 6822127
    Abstract: A selective hydrogenation catalyst for the seletive hydrogenation of unsaturated hydrocarbons, a process for preparing this catalyst and its use. The catalyst of the invention comprises a support, active component Pd, rare earth metals, and auxiliary metal Bi, Ag etc. The catalyst is able to hydrogenate high-unsaturated hydrocarbons such as alkyne with high selectivity at high space velocity while both green oil formation and carbon deposition on the catalyst are very low. It is applicable to an industrial cracking process.
    Type: Grant
    Filed: October 1, 2001
    Date of Patent: November 23, 2004
    Assignees: China Petroleum & Chemical Corporation, Beijing Research Institute of Chemical Industry, China Petroleum & Chemical Corporation
    Inventors: Wei Dai, Jing Zhu, Hui Peng, Yanlai Guo, Wei Mu, Helong Li, Qingzhou Cui
  • Publication number: 20040192983
    Abstract: A catalyst for the selective hydrogenation of acetylene comprising a support having a uniformly round external surface; palladium in the range of about 0.01 to 1.0 weight percent of the catalyst and substantially all of the palladium being concentrated in a skin periphery of the catalyst; and silver in the range of about 0.5 to 10.0 times the weight of the palladium. Preferably, the support is selected from the group consisting of alumina, titania, zirconia, zinc aluminate, zinc titanate and mixtures thereof, and/or the skin has a thickness less than about 400 microns.
    Type: Application
    Filed: February 10, 2004
    Publication date: September 30, 2004
    Applicant: Chevron Phillips Chemical Co.
    Inventors: Joseph J. Bergmeister, Tin-Tack P. Cheung, Gary A. Delzer
  • Publication number: 20040192982
    Abstract: The present invention is a process for removing alkynes and/or dienes from an olefin product stream withdrawn from an oxygenate-to-olefins reactor. The process comprises hydrogenating a first olefin stream that has alkynes and/or dienes in the presence of excess hydrogen and a first hydrogenation catalyst. The hydrogenation of the first olefin stream produces a second olefin stream that has unreacted hydrogen. The second olefin stream is contacted with a second hydrogenation catalyst producing a third olefin stream. The third olefin stream has low levels of hydrogen and alkynes and/or dienes.
    Type: Application
    Filed: March 28, 2003
    Publication date: September 30, 2004
    Inventors: Keith Holroyd Kuechler, David R. Lumgair
  • Patent number: 6794553
    Abstract: Process for the telomerization of a conjugated diene, wherein the conjugated diene is reacted with a compound containing an active hydrogen atom and having a formula R′—H in the presence of a telomerization catalyst based on: (a) a source of group VIII metal, (b) a bidentate ligand wherein the bidentate ligand has the general formula I R1R2M1—R—M2R3R4  (I) wherein M1 and M2 are independently P, As or Sb; R1, R2, R3 and R4 independently represent a monovalent aliphatic group; or R1, R2 and M1 together and/or R3, R4 and M2 together independently represent an optionally substituted aliphatic cyclic group with at least 5 ring atoms, of which one is the M1 or M2 atom, respectively; R represents a bivalent organic bridging group; and novel bidentate diphosphines which can be used in this process.
    Type: Grant
    Filed: November 4, 2002
    Date of Patent: September 21, 2004
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Michael Rolf Eberhard, Paul Gerald Pringle, Renata Helena van der Made