By Double-bond-shift Isomerization Patents (Class 585/664)
  • Patent number: 6858769
    Abstract: A catalyst for the selective oxidation of hydrogen has been developed. It comprises an inert core such as cordierite and an outer layer comprising a lithium aluminate support. The support has dispersed thereon a platinum group metal and a promoter metal, e.g. platinum and tin respectively. This catalyst is particularly effective in the selective oxidation of hydrogen in a dehydrogenation process.
    Type: Grant
    Filed: October 18, 2002
    Date of Patent: February 22, 2005
    Assignee: UOP LLC
    Inventors: Guy B. Woodle, Andrew S. Zarchy, Jeffery C. Bricker, Andrzej Z. Ringwelski
  • Patent number: 6852901
    Abstract: A process is provided to produce a 2-alkene product from a 1-alkene-containing feed stream. The process comprises contacting the 1-alkene-containing feed stream in a reactor zone to isomerize the 1-alkene-containing feed stream to produce the 2-alkene product. More specifically, a process is provided to produce a 2-butene product from a 1-butene containing feed stream.
    Type: Grant
    Filed: May 28, 2002
    Date of Patent: February 8, 2005
    Assignee: Chevron Phillips Chemical Company
    Inventors: Dan M. Hasenberg, Mitchell D. Refvik, Michael S. Matson
  • Patent number: 6841713
    Abstract: The invention relates to economical and efficient methods for producing 2-methylene-3-methylbicyclo[2,2,1]heptane, 2,3-dimethylbicyclo[2.2.1]hept-2-ene and the like that are useful for materials of producing base oil of traction drive fluid for traction drive lubricating oil. The methods comprise reacting one or more C3-4 acyclic olefins with cyclopentadiene and isomerizing the resulting bicyclo[2.2.1]heptene derivatives in the presence of an isomerization catalyst to give one or more bicyclo[2.2.1]heptane derivatives.
    Type: Grant
    Filed: February 6, 2001
    Date of Patent: January 11, 2005
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Toshiyuki Tsubouchi, Yukio Yoshida, Motohisa Ido, Masahiro Katayama
  • Publication number: 20040249229
    Abstract: A method of modifying the activity of a solid acid catalyst by contact with a carboxylic acid is presented. The modified catalyst is exposed to a feed mixture including olefins in a reaction zone, and an effluent including an isomerized olefin product is withdrawn from the reaction zone. The isomerized olefin product includes a more random distribution of internal olefins than the olefins of the feed mixture. The feed mixture and the isomerized olefin product include linear olefins. The isomerization results in no more than about 10 weight percent additional branched, compared to the olefins of the feed mixture, among the olefins of the isomerized olefin product. The isomerized olefin product includes no more than about 20 weight percent dimer. The olefin monomers of the feed mixture and the isomerized olefin product include from about 4 to about 30 carbon atoms. The effluent includes no more than about 20 weight percent ester. The solid acid catalyst may be an acidic ion exchange resin.
    Type: Application
    Filed: June 6, 2003
    Publication date: December 9, 2004
    Inventors: Jeffery C. Gee, Willie J. Isom, Bruce E. Kreischer
  • Patent number: 6822130
    Abstract: A catalyst composition comprising an alumina carrier, a Group VIII noble metal, and a halogen compound wherein the catalyst composition has total pore volume of more than 0.48 ml/g and wherein at least 50% of this total pore volume resides in pores with a diameter smaller than 12 nm. This catalyst composition has a higher activity in isomerization reactions, per gram of catalyst and per gram of Group VIII noble metal, than prior art catalyst compositions.
    Type: Grant
    Filed: March 6, 2003
    Date of Patent: November 23, 2004
    Assignee: Akzo Nobel N.V.
    Inventor: Pieter Jan Nat
  • Publication number: 20040210090
    Abstract: A process for reacting a first component with itself or a second component to produce a third component in which a first material comprising a first component or said first component and a second component is fed to divided wall column having a catalytic distillation structure in at least one of the separate vertical sections of the divided wall column where concurrently: (1) a first component alone or with a second component is contacted with a catalytic distillation structure in a distillation reaction zone thereby catalytically reacting at least a portion of the first component with itself or with the second component to form a product and (2) a first mixture comprising the first component and the product or the first component, the second component and the product; and withdrawing the product from the distillation column reactor; while within the column concurrently with the catalytic reaction and fractionation a second mixture is fractionated, which contains the first component and the product or first a
    Type: Application
    Filed: May 5, 2004
    Publication date: October 21, 2004
    Applicant: CATALYTIC DISTILLATION TECHNOLOGIES
    Inventors: Willibrord A. Groten, Mario J. Maraschino
  • Publication number: 20040210098
    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: Application
    Filed: March 5, 2004
    Publication date: October 21, 2004
    Inventors: Andreas Beckmann, Armin Rix
  • Publication number: 20040210091
    Abstract: A process for reacting a first component with itself or a second component to produce a third component in which a first material comprising a first component or said first component and a second component is fed to divided wall column having a catalytic distillation structure in at least one of the separate vertical sections of the divided wall column where concurrently: (1) a first component alone or with a second component is contacted with a catalytic distillation structure in a distillation reaction zone thereby catalytically reacting at least a portion of the first component with itself or with the second component to form a product and (2) a first mixture comprising the first component and the product or the first component, the second component and the product; and withdrawing the product from the distillation column reactor; while within the column concurrently with the catalytic reaction and fractionation a second mixture is fractionated, which contains the first component and the product or first a
    Type: Application
    Filed: May 5, 2004
    Publication date: October 21, 2004
    Applicant: CATALYTIC DISTILLATION TECHNOLOGIES
    Inventors: Willibrord A. Groten, Mario J. Maraschino
  • Publication number: 20040210092
    Abstract: A process for reacting a first component with itself or a second component to produce a third component in which a first material comprising a first component or said first component and a second component is fed to divided wall column having a catalytic distillation structure in at least one of the separate vertical sections of the divided wall column where concurrently: (1) a first component alone or with a second component is contacted with a catalytic distillation structure in a distillation reaction zone thereby catalytically reacting at least a portion of the first component with itself or with the second component to form a product and (2) a first mixture comprising the first component and the product or the first component, the second component and the product; and withdrawing the product from the distillation column reactor; while within the column concurrently with the catalytic reaction and fractionation a second mixture is fractionated, which contains the first component and the product or first a
    Type: Application
    Filed: May 5, 2004
    Publication date: October 21, 2004
    Applicant: CATALYTIC DISTILLATION TECHNOLOGIES
    Inventors: Willibrord A. Groten, Mario J. Maraschino
  • Publication number: 20040199040
    Abstract: A process to prepare a microcrystalline wax by contacting under hydroisomerisation conditions a feed, having at least 80 wt % of normal-paraffins and having a congealing point of above 60 ° C., with a catalyst having a noble metal and a porous silica-alumina carrier.
    Type: Application
    Filed: December 12, 2003
    Publication date: October 7, 2004
    Inventors: Arend Hoek, Hendrik Schadenberg
  • Publication number: 20040192994
    Abstract: A method for making propylene from alpha olefins, internal linear olefins, and isoolefins wherein the internal linear olefins are separated and then disproportionated with ethylene to form a propylene product, while the alpha olefins are subjected to double bond isomerization to form additional internal linear olefins, and the isoolefins are subjected to skeletal isomerization to form yet additional internal linear olefins.
    Type: Application
    Filed: March 26, 2003
    Publication date: September 30, 2004
    Inventors: Robert S. Bridges, Donald H. Powers, Steven T. Coleman
  • Patent number: 6781022
    Abstract: The objective of the present invention is a polyvalent bifunctional catalyst and the process of its realization. A catalyst characterized by the fact that it contains, over a TiO2 support, an oxide or a mixture of metallic oxides of MC2 type obtained by reduction of the corresponding MC3 oxides, the metal(s) forming the MO2 oxides are chosen from the group formed by W and Mo.
    Type: Grant
    Filed: May 8, 2001
    Date of Patent: August 24, 2004
    Assignee: Boubyan Petrochemical Company (K.S.C.)
    Inventors: Ali Katrib, Damien Mey, Gilbert Maire
  • Patent number: 6768038
    Abstract: A method for making alpha olefins from internal olefins using catalytic distillation techniques and an olefin double bond isomerization catalyst, and separately recovering said alpha olefins.
    Type: Grant
    Filed: December 20, 2002
    Date of Patent: July 27, 2004
    Assignee: Equistar Chemicals, LP
    Inventor: Donald H. Powers
  • Publication number: 20040122278
    Abstract: A method for making alpha olefins from internal olefins using catalytic distillation techniques and an olefin double bond isomerization catalyst, and separately recovering said alpha olefins.
    Type: Application
    Filed: December 20, 2002
    Publication date: June 24, 2004
    Inventor: Donald H. Powers
  • Publication number: 20040106836
    Abstract: A process is provided to produce a 2-alkene product from a 1-alkene-containing feed stream. The process comprises contacting the 1-alkene-containing feed stream in a reactor zone to isomerize the 1-alkene-containing feed stream to produce the 2-alkene product. More specifically, a process is provided to produce a 2-butene product from a 1-butene containing feed stream.
    Type: Application
    Filed: May 28, 2002
    Publication date: June 3, 2004
    Inventors: Dan M. Hasenberg, Mitchell D. Refvik, Michael S. Matson
  • Publication number: 20040097761
    Abstract: A microemulsion containing water, a densified fluid, a surfactant, and an organometallic catalyst is used to catalyze chemical reactions. The organometallic catalyst preferably has substantial solubility in the water phase of the microemulsion. Separation of reaction products from the microemulsion is facilitated by removal of the densified fluid.
    Type: Application
    Filed: August 15, 2003
    Publication date: May 20, 2004
    Inventors: Can Erkey, Xing Dong
  • Publication number: 20040059171
    Abstract: The present invention is directed to a hydrocarbon conversion apparatus. The apparatus comprises the following: a plurality of riser reactors, each of the riser reactors having a first end into which a catalyst can be fed and a second end through which the catalyst can exit the riser reactor; a separation zone provided to separate the catalyst from products of a reaction conducted in the hydrocarbon conversion apparatus; at least one transport conduit having a first end in fluid communication with at least two of the second ends of the riser reactors and a second end extending into the separation zone; and at least one catalyst return in fluid communication with the separation zone and the first ends of the riser reactors, the catalyst return being provided to transfer the catalyst from the separation zone to the first ends of the riser reactors.
    Type: Application
    Filed: September 24, 2002
    Publication date: March 25, 2004
    Inventor: Walter R. Brookhart
  • Publication number: 20040020827
    Abstract: The present invention relates to new crystalline molecular sieve SSZ-64 prepared using a N-cyclobutylmethyl-N-ethylhexamethyleneiminium cation or N-cyclobutylmethyl-N-ethylheptamethyleneiminium cation structure directing agent, and processes employing SSZ-64 in a catalyst.
    Type: Application
    Filed: August 1, 2002
    Publication date: February 5, 2004
    Inventor: Saleh Elomari
  • Publication number: 20030233018
    Abstract: A method of making 1-olefin such as 1-butene by contacting a mixed olefin feedstock preferably with a small pore molecular sieve catalyst, especially SAPO-34, at a temperature from about 300° C. to about 700° C., and an effective pressure and WHSV to form an olefin product with a 1-olefin:isoolefin conversion index greater than 1:1. A mixed olefin feedstock produced from an oxygenate to olefin process is particularly well suited for the production of 1-olefin.
    Type: Application
    Filed: June 18, 2002
    Publication date: December 18, 2003
    Inventors: Stephen H. Brown, Stephen N. Vaughn, Jose Guadalupe Santiesteban, Karl G. Strohmaier
  • Patent number: 6649662
    Abstract: Methods for converting of syngas to higher molecular weight products using Fischer-Tropsch synthesis, and methods for optimizing the catalyst systems in the synthesis, are disclosed. In one embodiment, the methods use cobalt/ruthenium Fischer-Tropsch catalysts in combination with an olefin isomerization catalyst, which isomerizes double bonds in C4+ olefins as they are formed. In another embodiment, the methods use Fischer-Tropsch catalysts that may or may not be cobalt/ruthenium catalysts, in combination with olefin isomerization catalysts which are acidic enough to isomerize the C4+ olefins but not too acidic to cause rapid coking. A benefit of using the relatively less acidic zeolites is that the ratio of iso-paraffins to aromatics is increased relative to when more acidic zeolites are used. Also, the relatively less acidic zeolites do not coke as readily as the relatively more acidic zeolites.
    Type: Grant
    Filed: June 20, 2002
    Date of Patent: November 18, 2003
    Assignee: Chevron U.S.A. Inc.
    Inventor: Charles L. Kibby
  • Patent number: 6593505
    Abstract: A catalyst comprising A) a stationary acid component selected from the group consisting of a perfluorinated ion exchange polymer on an inert support, a silane modified perfluorosulfonic acid, and a sulfated metal oxide; and B) a mobile acid component selected from the group consisting of chlorosulfonic acid, fluorosulfonic acid, a fluorinated monosulfonic acid, a fluorinated sulfonimide, a fluorinated disulfonic acid, and an adjunct acid mixture is disclosed.
    Type: Grant
    Filed: January 13, 2003
    Date of Patent: July 15, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark A. Harmer, Eugene F. Hartstein
  • 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: 6518469
    Abstract: A process for improved yields of heavier olefins from a substantially narrow range of lighter hydrocarbon feed stock containing olefins in a reaction distillation column comprising feeding a narrow range of hydrocarbon feed stock containing olefin into a reaction distillation column at a point between its bottom and top, contacting the olefins at the point of feed with a disproportionation catalyst in alternating arrangement with an isomerization catalyst or a mixture thereof and keeping the reaction mixture in a state of vapor-liquid equilibrium for concentrating the lighter reaction products in the vapor phase and the heavier reaction products in the liquid phase by maintaining a controlled pressure and temperature profile in the reactive distillation column and for reactively creating the desired heavier molecular weight olefins over the catalysts and collecting it as bottoms product and removing the lighter molecular weight olefins overhead from the top of the reactive distillation column.
    Type: Grant
    Filed: January 29, 2002
    Date of Patent: February 11, 2003
    Inventor: Armen Nazar Abazajian
  • Publication number: 20030009070
    Abstract: A process for the double bond isomerization of an olefin, which process comprises contacting a feed comprising the olefin with an isomerization catalyst, wherein prior to contacting the feed with the isomerization catalyst one or more components of the feed are pretreated by contacting with a pretreating material which comprises a zeolite which has a pore size of at least 0.
    Type: Application
    Filed: June 10, 2002
    Publication date: January 9, 2003
    Inventors: Michael Joseph Doll, Brendan Dermot Murray
  • Publication number: 20030009072
    Abstract: An olefin isomerization process employs a basic metal oxide catalyst, such as magnesium oxide, which retains at least about 85 percent of its initial activity for at least about 168 hours of on-stream time. The catalyst is preferably a high purity magnesium oxide. The olefin isomerization process and catalyst described herein are advantageously used for the production of a terminal olefin such as 1-butene from an internal olefin such as 2-butene.
    Type: Application
    Filed: May 23, 2001
    Publication date: January 9, 2003
    Inventors: Robert J. Gartside, Marvin I. Greene
  • Publication number: 20030004385
    Abstract: A process is provided for treating a basic metal oxide olefin isomerization catalyst, such as magnesium oxide. The catalyst is activated by contact with a deoxygenated nitrogen under activation conditions. The olefin isomerization process and catalyst described herein are advantageously used for the production of a terminal olefin such as 1-butene from an internal olefin such as 2-butene.
    Type: Application
    Filed: May 23, 2001
    Publication date: January 2, 2003
    Inventors: Robert J. Gartside, Marvin I. Greene
  • Patent number: 6495732
    Abstract: A process for the isomerization of mono-olefins in aliphatic hydrocarbon streams is carried out at 40 to 300° F. under low hydrogen partial pressure in the range of about 0.1 psi to less than 70 psi at 0 to 350 psig in a distillation column reactor containing a hydrogenation catalyst which serves as a component of a distillation structure, such as supported PdO encased in tubular wire mesh. Essentially no hydrogenation of the mono-olefins occurs.
    Type: Grant
    Filed: December 12, 2000
    Date of Patent: December 17, 2002
    Assignee: Catalytic Distillation Technologies
    Inventors: Dennis Hearn, Robert P. Arganbright, Edward M. Jones, Jr., Lawrence A. Smith, Jr., Gary R. Gildert
  • Publication number: 20020147374
    Abstract: A process for improved yields of heavier olefins from a substantially narrow range of lighter hydrocarbon feed stock containing olefins in a reaction distillation column comprising feeding a narrow range of hydrocarbon feed stock containing olefin into a reaction distillation column at a point between its bottom and top, contacting the olefins at the point of feed with a disproportionation catalyst in alternating arrangement with an isomerization catalyst or a mixture thereof and keeping the reaction mixture in a state of vapor-liquid equilibrium for concentrating the lighter reaction products in the vapor phase and the heavier reaction products in the liquid phase by maintaining a controlled pressure and temperature profile in the reactive distillation column and for reactively creating the desired heavier molecular weight olefins over the catalysts and collecting it as bottoms product and removing the lighter molecular weight olefins overhead from the top of the reactive distillation column.
    Type: Application
    Filed: January 29, 2002
    Publication date: October 10, 2002
    Inventor: Armen Nazar Abazajian
  • Patent number: 6420619
    Abstract: The C3 to C6 cut from a cracking process containing propylene, butane, 1-butene, 2-butene and acetylenic and diene components including butadiene are preferentially converted to propylene. The cut is simultaneously fractionated and catalytically hydrogenated to hydrogenate the acetylenic and diene components. The fractionation and subsequent separation recovers a C4 component comprising a mixture of isobutene, 1-butene and 2-butene. This C4 component is then further simultaneously fractionated and catalytically hydrogenated and hydroisomerized to hydrogenate remaining butadiene, remove isobutene overhead and convert 1-butene to 2-butene leaving a bottoms of 2-butene. The 2-butene is then injected with ethylene and catalytically metathesized to form propylene.
    Type: Grant
    Filed: January 25, 2001
    Date of Patent: July 16, 2002
    Inventors: Robert J. Gartside, Gary R. Gildert
  • Patent number: 6407302
    Abstract: A method for the isomerization of a mixture of vinyl and vinylidene olefins having 10 to 35 carbons atoms to form a mixture comprising both di- and tri-substituted internal olefins including deep internal olefins.
    Type: Grant
    Filed: January 7, 2000
    Date of Patent: June 18, 2002
    Assignee: BP Corporation North America Inc.
    Inventors: Fred Chun-Chien Twu, William L. Cox
  • Patent number: 6395945
    Abstract: A novel integrated olefin processing scheme is provided where olefins and paraffins are processed to produce high octane gasoline blending components. The integrated process involves the processing of olefins by hydroisomerization to produce a hydroisomerate stream which is subsequently alkylated in an alkylation process with branched chain paraffin hydrocarbons to produce an alkylate product. The alkylate product can further be separated into various fractions, including propane, n-butane, i-butane and a C5+ alkylate stream. The C5+ alkylate stream can be separated into an i-pentane stream and a deisopentanized C5+ alkylate stream.
    Type: Grant
    Filed: March 31, 2000
    Date of Patent: May 28, 2002
    Assignee: Phillips Petroleum Company
    Inventor: Bruce B. Randolph
  • Patent number: 6388160
    Abstract: There is disclosed a method for producing 2,3-dimethylbutene-1 and 2,3-dimethylbutene-2, which is characterized by the steps of (a) dimerizing propylene in a propylene-dimerization step using a nickel complex catalyst as described below as a propylene-dimerization catalyst having propylene-dimerization activity and DMB-1 selectivity, (b) rectifying the resulting reaction solution to obtain 2,3-dimethylbutene-1 as a distillate and a distillation residue containing 2,3-dimethylbutene-1 in a 2,3-dimethylbutene-1 distillation step, (c) allowing the distillation residue to contact with sulfuric acid, sulfonic acid or hetetopolyacid to isomerize 2,3-dimethylbutene-1 in said distillation residue into 2,3-dimethylbutene-2 in an isomerization step, and (d) rectifying the resulting isomerization reaction solution to obtain 2,3-dimethylbutene-2 in a 2,3-dimethylbutene-2 distillation step, wherein said nickel complex catalyst containing (A) at least one nickel compound and the like, (B) a trialkylaluminum, (C) a
    Type: Grant
    Filed: May 25, 2000
    Date of Patent: May 14, 2002
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Makoto Itagaki, Gohfu Suzukamo, Michio Yamamoto
  • Patent number: 6331573
    Abstract: An integrated process for producing liquid fuels from syngas via a two-stage Fischer-Tropsch reaction is disclosed. The first stage of the Fischer-Tropsch chemistry is performed using conditions in which chain growth probabilities are relatively low to moderate, and the product of the reaction includes a relatively high proportion of low molecular (C2-8) weight olefins and a relatively low proportion of high molecular weight (C30+) waxes. The product from the first stage is fed into the second stage where the chain growth probabilities are relatively high. The wax and other paraffins produced in the first reaction are largely inert under these conditions. The light olefins compete with heavier olefins for chain initiation, and fewer chains will be initiated at C20+. With most chains initiated at C2-8, moderate chain growth probability will produce a relatively larger fraction in the C5-12 range. In this manner, wax yield is minimized.
    Type: Grant
    Filed: February 29, 2000
    Date of Patent: December 18, 2001
    Assignee: Chevron U.S.A. Inc.
    Inventor: Charles L. Kibby
  • Publication number: 20010047119
    Abstract: A solid acid-base catalyst contains vanadium pentoxide hydrate.
    Type: Application
    Filed: March 15, 1999
    Publication date: November 29, 2001
    Inventors: NOBUJI KISHIMOTO, ETSUSHIGE MATSUNAMI
  • Patent number: 6294707
    Abstract: The present invention is directed to a continuous process for producing a desired hydrocarbon product using a heterogeneous slurry catalyst, to the product of said process, and to the reactor utilized in such process.
    Type: Grant
    Filed: August 29, 1997
    Date of Patent: September 25, 2001
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Christopher Lynn Becker, James Richardson Lattner, Mark T. Swihart
  • Patent number: 6262326
    Abstract: A process for the preparation of at least one spherically shaped porous microcomposite is provided which microcomposite comprises a perfluorinated ion-exchange polymer containing pendant sulfonic and/or carboxylic acid groups entrapped within and highly dispersed throughout a network of inorganic oxide, wherein the weight percentage of the perfluorinated ion-exchange polymer in the microcomposite is from about 0.1 to about 90 percent, and wherein the size of the pores in the microcomposite is about 0.
    Type: Grant
    Filed: June 6, 2000
    Date of Patent: July 17, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Qun Sun
  • Patent number: 6242661
    Abstract: A process for the separation of isobutene, otherwise inseparable from butene-1 by fractionation, in high purity from butenes contained in a mixed hydrocarbon stream containing butene-1, butene-2 and small amounts of butadiene in which the mixed hydrocarbon stream is fed to distillation column reactor containing an alumina supported palladium oxide catalyst. The column is operated to tend to exclude butene-2 from contact with the catalyst and to maintain butene-1 in contact with the catalyst to isomerize the butene-1 to butene-2. As butene-2 is produced it is distilled away from the catalyst, upsetting the equilibrium and allowing for a greater than equilibrium amount of butene-2. The isobutene and isobutane are concurrently separated from the butene-2. Additionally, any butadiene in the feed is hydrogenated to butenes. The bottoms is rich in butene-2.
    Type: Grant
    Filed: July 16, 1999
    Date of Patent: June 5, 2001
    Assignee: Catalytic Distillation Technologies
    Inventors: Gary G. Podrebarac, John R. Adams
  • Patent number: 6242662
    Abstract: For obtaining butene-1 from butene-2, a charge containing at least one of the isomers of butene-2 is introduced into a distillation zone linked to a hydro-isomerization zone. Part of the effluent from the bottom of the distillation column is removed from the distillation zone, heated in a heat exchanger and passed into an external hydro-isomerization zone. The hydro-isomerization effluent is removed from the hydro-isomerization zone, cooled in a heat exchanger, and then reintroduced into the distillation zone. Effluent containing butene-1 is withdrawn from the top of the column of the distillation zone.
    Type: Grant
    Filed: January 14, 1999
    Date of Patent: June 5, 2001
    Assignee: Institut Francais du Petrole
    Inventors: Michel Dorbon, François Hugues, Jean-Charles Viltard, Blaise Didillon, Alain Forestiere
  • Patent number: 6215036
    Abstract: A process for processing a feedstock comprising a major amount of olefinic hydrocarbons having 4 carbon atoms per molecule, including isobutene as well as but-1-ene and but-2-enes, wherein the process comprises processing said feedstock in a distillation zone associated with a hydroisomerization reaction zone located at least partly external to the distillation zone, said processing comprising drawing at the height of a draw-off level of the distillation zone at least part of the liquid flowing in the distillation zone, passing said liquid into the external hydroisomerization reaction zone to form a hydroisomerized effluent, and reintroducing at least part of the effluent from said reaction zone reintroduced into the distillation zone at one or more reintroduction level(s), so as to ensure the continuity of the distillation.
    Type: Grant
    Filed: September 27, 1999
    Date of Patent: April 10, 2001
    Assignee: Institut Francais du Petrole
    Inventors: Michel Dorbon, Blaise Didillon, Jean-Charles Viltard, Jean Cosyns, Charles Cameron, Heinz Unterberg, Günter Schümmer, William Brown
  • Patent number: 6137023
    Abstract: The invention relates to a process for producing high purity isobutene from a hydrocarbon cut essentially comprising olefinic hydrocarbons containing 4 carbon atoms per molecule including isobutene, also butene-1 and butene-2 compounds in a ratio which substantially corresponds to the thermodynamic equilibrium. The process comprises passing the cut into a distillation zone (3) associated with a hydroisomerisation reaction zone, the bottom product of the distillation zone comprising butene-2 compounds being passed into a skeletal isomerisation zone (2) where the linear butenes are at least partially isomerised to isobutene, at least part of the principal effluent from the skeletal isomerisation zone being recycled upstream of the reactive distillation zone (3).
    Type: Grant
    Filed: December 22, 1997
    Date of Patent: October 24, 2000
    Assignee: Institut Francais du Petrole
    Inventors: Michel Dorbon, Jean-Alain Chodorge, Jean Cosyns, Jean-Charles Viltard, Blaise Didillon
  • Patent number: 6075175
    Abstract: A process for catalytically isomerizing olefins, particularly for isomerizing alkenyl bridged ring compounds to the corresponding alkylidene bridged ring compounds. The catalyst is prepared by forming a dispersion of a metallic alkali metal on a support with simultaneous exposure to oxygen.
    Type: Grant
    Filed: September 29, 1998
    Date of Patent: June 13, 2000
    Assignee: Exxon Chemical Patents, Inc.
    Inventors: Robert Scott Smith, Jos Peter Wristers
  • Patent number: 6054629
    Abstract: The present invention relates to a method of using nickel alumina catalyst to isomerize linear alpha olefins substantially completely to linear internal olefins with no significant increase in branch internal olefin content.
    Type: Grant
    Filed: July 15, 1998
    Date of Patent: April 25, 2000
    Assignee: Chevron Chemical Company LLC
    Inventors: Eduardo J. Baralt, Amy C. King, Carol E. King
  • Patent number: 5990368
    Abstract: Providing an isomerization process which can isomerize allenes to alkynes less expensively and stably is an assignment to be solved by the present invention and given thereto. The present invention is an isomerization process including the step of reacting an allene-lype hydrocarbon compound (R.sub.1 R.sub.2 C.dbd.C.dbd.CR.sub.3 R.sub.4) in the presence of alkaline-earth metal hydride working as an isomerization catalyst, thereby isomerizing the allene-type hydrocarbon compound to an alkyne-type hydrocarbon compound (R.sub.1 C.ident.C--CR.sub.2 R.sub.3 R.sub.4).
    Type: Grant
    Filed: July 7, 1998
    Date of Patent: November 23, 1999
    Assignee: Kabushiki Kaisha Toyota Chuo Kenkyusho
    Inventors: Mitsuru Nakano, Bruce M. Novak
  • Patent number: 5990369
    Abstract: The present invention relates to a process for the production of light olefins comprising olefins having from 2 to 4 carbon atoms per molecule from an oxygenate feedstock. The process comprises passing the oxygenate feedstock to an oxygenate conversion zone containing a metal alumninophosphate catalyst to produce a light olefin stream. The light olefin stream is fractionated and a portion of the products are metathesized to enhance the yield of the ethylene, propylene, and/or butylene products. Propylene can be metathesized to produce more ethylene, or a combination of ethylene and butene can be metathesized to produce more propylene. This combination of light olefin production and metathesis, or disproportionation provides flexibility to overcome the equilibrium limitations of the metal aluminophosphate catalyst in the oxygenate conversion zone. In addition, the invention provides the advantage of extended catalyst life and greater catalyst stability in the oxygenate conversion zone.
    Type: Grant
    Filed: February 9, 1998
    Date of Patent: November 23, 1999
    Assignee: UOP LLC
    Inventors: Paul T. Barger, R. Joe Lawson, Bipin V. Vora
  • Patent number: 5981820
    Abstract: A process and catalyst for isomerizing olefins are disclosed. The process and catalyst are particularly useful for isomerizing alkenyl bridged ring compounds to the corresponding alkyladiene bridged ring compounds. In one embodiment, the isomerization catalyst comprises an oxygen treated mixture of an alkali metal on a dried support having a surface area of 125 to 195 m.sup.2 /g when the support consists essentially of alumina wherein the alumina precursor is a large crystallite pseudoboehmite. The catalyst is particularly useful for isomerizing 5-vinyl-2-norbornene to 5-ethylidiene-2-norbornene. The catalyst is very active and highly selective and resistant to catalyst poisons. The process contacts the catalyst with an alkenyl bridged ring compound and yields the corresponding alkyladiene bridged ring compound.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: November 9, 1999
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Robert Scott Smith, Christopher Lynn Becker
  • Patent number: 5969205
    Abstract: C.sub.4 -C.sub.6 -alkenes having an internal double bond can be produced by hydroisomerization of C.sub.4 -C.sub.6 -alkenes having a terminal double bond in the presence of H.sub.2 on a catalyst having a content of a noble metal of group VIII of the Periodic Table of the Elements (Mendeleev), if C.sub.4 -C.sub.6 -alkenes having a terminal double bond are fed into a hydroisomerization reactor after preheating, as such or in a mixture with other hydrocarbons, and the reaction product is divided into a work-up stream and a recycle stream. The recycle stream is recycled to the inlet of the hydroisomerization reactor and is used there as feed together with the C.sub.4 -C.sub.6 -alkenes having a terminal double bond or with the hydrocarbon stream comprising the C.sub.4 -C.sub.6 -alkenes having a terminal double bond and with the H.sub.2.
    Type: Grant
    Filed: August 21, 1998
    Date of Patent: October 19, 1999
    Assignee: EC Erdolchemie GmbH
    Inventors: Arnd Stuwe, Jorg-Uwe Michel, Matthias Baum, Franz Kaledat
  • Patent number: 5965783
    Abstract: A process for producing a synthetic hydrocarbon product is provided comprising contacting under isomerization conditions an olefin feed comprising linear olefins with a catalyst comprising an intermediate pore size molecular sieve, wherein the catalyst is substantially free of Group VIII metals. The synthetic hydrocarbon product exhibits a low pour point and low toxicity to marine life.
    Type: Grant
    Filed: December 3, 1996
    Date of Patent: October 12, 1999
    Assignee: Chevron Chemical Company
    Inventors: Jeffrey C. Gee, Roger C. Williamson, Christophe J. Lawrie, Stephen J. Miller
  • Patent number: 5955640
    Abstract: Integrated process for the production of butene-1 which comprises feeding a C.sub.4 hydrocarbon stream to a separation unit of butene-1 and recycling the remaining stream to the same unit after treatment in a bond isomerization section to convert the remaining butenes-2 into butene-1, a molecular sieve separation unit is inserted in the cycle operating with the hydrocarbons in a vapour phase, for the purge of the paraffins.
    Type: Grant
    Filed: May 24, 1996
    Date of Patent: September 21, 1999
    Assignees: Enichem S.p.A., Snamprogetti S.p.A.
    Inventors: Renato Paludetto, Alfredo Orsi, Roberto Trotta, Gianni Donati
  • Patent number: 5948948
    Abstract: The invention concerns a process for isomerising a feed containing essentially hydrocarbons, preferably paraffins preferably containing 5 and/or 6 carbon atoms per molecule, in which said feed is treated in a distillation zone comprising an exhausting zone and a rectification zone associated with an isomerisation reaction zone, in the presence of an isomerisation catalyst and a gas stream containing hydrogen, characterized in that the reaction zone is at least partially internal to the distillation zone, and wherein the hydrogen-containing gas is fed by a dedicated gas distributor to the bottom of at least one catalytic bed within the isomerization reaction zone.
    Type: Grant
    Filed: February 4, 1997
    Date of Patent: September 7, 1999
    Assignee: Institut Francais du Petrole
    Inventors: Etienne Lebas, Sophie Jullian, Christine Travers, Pierre Capron, Jean-Fran.cedilla.ois Joly, Michel Thery
  • Patent number: 5948946
    Abstract: Porous microcomposites have been prepared from perfluorinated ion-exchange polymer and metal oxides such as silica using a sol-gel process. Such microcomposites possess high surface area and exhibit extremely high catalytic activity. Isomerization of terminal olefins is possible with such porous microcomposites.
    Type: Grant
    Filed: July 23, 1998
    Date of Patent: September 7, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Qun Sun