Group Viii Metal Containing Catalyst Utilized Patents (Class 562/522)
  • Patent number: 10584088
    Abstract: Processes for producing an ?,?-unsaturated carboxylic acid, such as acrylic acid, or a salt thereof, using treated solid oxides are disclosed. The treated solid oxides can be calcined solid oxides, metal-treated solid oxides, or metal-treated chemically-modified solid oxides, illustrative examples of which can include sodium-treated alumina, calcium-treated alumina, zinc-treated alumina, sodium-treated sulfated alumina, sodium-treated fluorided silica-coated alumina, and similar materials.
    Type: Grant
    Filed: October 29, 2018
    Date of Patent: March 10, 2020
    Assignee: Chevron Phillips Chemical Company LP
    Inventors: Mark L. Hlavinka, Max P. McDaniel, Pasquale Iacono
  • Patent number: 9416087
    Abstract: Processes for producing an ?,?-unsaturated carboxylic acid, such as acrylic acid, or a salt thereof, using solid promoters are disclosed. The solid promoters can be certain solid oxides, mixed oxides, and clays, illustrative examples of which can include alumina, zirconia, magnesia, magnesium aluminate, sepiolite, and similar materials.
    Type: Grant
    Filed: October 8, 2014
    Date of Patent: August 16, 2016
    Assignee: Chevron Phillips Chemical Company LP
    Inventors: Mark L. Hlavinka, Max P. McDaniel
  • Patent number: 9273020
    Abstract: Process for the production of a chemical compound from a carbon dioxide starting material, comprising the steps of a) providing a feed stream consisting mainly of carbon dioxide; b) electrolyzing in an electrolysis stage the carbon dioxide in the feed stream to a first gas stream containing carbon monoxide and a second gas stream containing oxygen, wherein the molar ratio between carbon monoxide and oxygen is about 1:0.5 in an electrolysis stage; c) adjusting the composition of the first gas stream or the second gas stream or both gas streams to include carbon dioxide, either by operating at less than full conversion of CO2 or by sweeping one or both gas streams with a gas containing CO2 or by at some stage between the electrolysis cell and the oxidative carbonylation reactor diluting one or both gas streams with a gas containing CO2; all while maintaining an overall molar ratio of carbon monoxide to oxygen of about 1:0.
    Type: Grant
    Filed: April 11, 2013
    Date of Patent: March 1, 2016
    Assignee: Haldor Topsoe A/S
    Inventors: Niels Christian Schjødt, John Bøgild Hansen, Claus Friis Pedersen
  • Publication number: 20140296570
    Abstract: The invention relates to a process for converting hydrocarbons into products containing aldehydes and/or alcohols. The invention also relates to producing olefins from the aldehyde and alcohol, to polymerizing the olefins, and to equipment useful for these processes.
    Type: Application
    Filed: December 20, 2011
    Publication date: October 2, 2014
    Applicant: Exxonmobile Chemical Patents Inc.
    Inventors: Paul F. Keusenkothen, Frank Hershkowitz
  • Patent number: 8642803
    Abstract: A process for preparing an alkali metal or alkaline earth metal salt of an ?,?-ethylenically unsaturated carboxylic acid, wherein a) an alkene, carbon dioxide and a carboxylation catalyst are converted to an alkene/carbon dioxide/carboxylation catalyst adduct, b) the adduct is decomposed to release the carboxylation catalyst with an auxiliary base to give the auxiliary base salt of the ?,?-ethylenically unsaturated carboxylic acid, c) the auxiliary base salt of the ?,?-ethylenically unsaturated carboxylic acid is reacted to release the auxiliary base with an alkali metal or alkaline earth metal base to give the alkali metal or alkaline earth metal salt of the ?,?-ethylenically unsaturated carboxylic acid. Salts of ?,?-ethylenically unsaturated carboxylic acids, such as sodium acrylate in particular, are required in large amounts, for example, for production of water-absorbing resins.
    Type: Grant
    Filed: March 3, 2011
    Date of Patent: February 4, 2014
    Assignee: BASF SE
    Inventors: Michael Limbach, Jeremie Miller, Stephan Schunk
  • Patent number: 8389760
    Abstract: Disclosed is a palladium-containing catalyst which enables to produce an ?,?-unsaturated carboxylic acid in high selectivity from an olefin or an ?,?-unsaturated aldehyde. Also disclosed are a method for producing such a catalyst and a method for producing an ?,?-unsaturated carboxylic acid using such a catalyst. Specifically disclosed is a palladium-containing catalyst containing 0.001 to 0.25 mole of antimony element to 1 mole of palladium element or a palladium-containing catalyst containing palladium element which composes a metal, tellurium element, and bismuth element.
    Type: Grant
    Filed: November 8, 2011
    Date of Patent: March 5, 2013
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Toshiya Yasukawa, Toshiki Matsui, Ken Ooyachi, Yoshiyuki Himeno, Wataru Ninomiya
  • Patent number: 8088945
    Abstract: Disclosed is a palladium-containing catalyst which enables to produce an ?,?-unsaturated carboxylic acid in high selectivity from an olefin or an ?,?-unsaturated aldehyde. Also disclosed are a method for producing such a catalyst and a method for producing an ?,?-unsaturated carboxylic acid using such a catalyst. Specifically disclosed is a palladium-containing catalyst containing 0.001 to 0.25 mole of antimony element to 1 mole of palladium element or a palladium-containing catalyst containing palladium element which composes a metal, tellurium element, and bismuth element.
    Type: Grant
    Filed: December 10, 2010
    Date of Patent: January 3, 2012
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Toshiya Yasukawa, Toshiki Matsui, Ken Ooyachi, Yoshiyuki Himeno, Wataru Ninomiya
  • Patent number: 8088947
    Abstract: The present invention relates to a method for producing methacrolein and/or methacrylic acid characterized in that the catalyst filling length of a dehydration catalyst layer is 3 to 20% of the catalyst filling length of an oxidation catalyst layer in a method where raw material gas containing gaseous t-butanol is supplied to a fixed-bed multitubular reactor having a dehydration catalyst layer and an oxidation catalyst layer in this order, from the entrance for raw material gas toward the exit, to produce methacrolein and/or methacrylic acid by dehydration reaction and catalytic gas phase oxidation reaction, and the present invention can increase the conventional yield of approximately 80% to 81 to 82% even when a reaction bath temperature is relatively low (approximately 355° C.).
    Type: Grant
    Filed: March 30, 2007
    Date of Patent: January 3, 2012
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Tatsuhiko Kurakami, Toshitake Kojima, Yoshimasa Seo
  • Patent number: 8058472
    Abstract: The present invention concerns a new efficient method for the selective transformation, under mild conditions and in aqueous medium, of gaseous (ethane, propane and n-butane) and liquid (n-pentane, n-hexane, cyclopentane and cyclohexane) alkanes into carboxylic acids bearing one more carbon atom, characterized by a single-pot low-temperature (25-60° C.) reaction of the alkane with carbon monoxide in water/acetonitrile liquid medium, either in the absence or in the presence of a metal catalyst, in systems containing also an oxidant (a peroxodisulphate salt).
    Type: Grant
    Filed: January 17, 2008
    Date of Patent: November 15, 2011
    Assignee: Instituto Superior Tecnico
    Inventors: Armando Pombeiro, Marina Kirillova, Alexander Kirillov, Jose Armando Silva, Joao Frausto Da Silva
  • Publication number: 20110218359
    Abstract: A process for preparing an alkali metal or alkaline earth metal salt of an ?,?-ethylenically unsaturated carboxylic acid, wherein a) an alkene, carbon dioxide and a carboxylation catalyst are converted to an alkene/carbon dioxide/carboxylation catalyst adduct, b) the adduct is decomposed to release the carboxylation catalyst with an auxiliary base to give the auxiliary base salt of the ?,?-ethylenically unsaturated carboxylic acid, c) the auxiliary base salt of the ?,?-ethylenically unsaturated carboxylic acid is reacted to release the auxiliary base with an alkali metal or alkaline earth metal base to give the alkali metal or alkaline earth metal salt of the ?,?-ethylenically unsaturated carboxylic acid. Salts of ?,?-ethylenically unsaturated carboxylic acids, such as sodium acrylate in particular, are required in large amounts, for example, for production of water-absorbing resins.
    Type: Application
    Filed: March 3, 2011
    Publication date: September 8, 2011
    Applicant: BASF SE
    Inventors: Michael LIMBACH, Jeremie MILLER, Stephan SCHUNK
  • Patent number: 7820849
    Abstract: A process is provided, in particular a continuous process for the carbonylation of butadiene by reacting the butadiene with carbon monoxide and a hydroxyl group-containing compound in the presence of a palladium catalyst system in a reaction zone to form a reaction mixture, said catalyst system comprising (a) a source of palladium cations, (b) a mono-, bi- or multidentate phosphine ligand, containing at least one phosphorus atom which is directly bound to two or three aliphatic carbon atoms, as process ligand to produce a palladium-phosphine ligand complex catalyst, and (c) a source of anions, said process ligand (b) containing the moiety shown in formula (I), wherein A1 and A2 each represent an aliphatic carbon atom which can be connected to one or more aliphatic or aromatic carbon atoms or both A1 and A2 are part of an at least 5-membered ring including the phosphorus atom, and X represents an aliphatic or aromatic carbon atom which can be connected to one or more aliphatic or aromatic carbon atoms or X
    Type: Grant
    Filed: June 28, 2004
    Date of Patent: October 26, 2010
    Assignee: DSM IP Assets B.V.
    Inventors: Otto Erik Sielcken, Imre Toth, Henricus Anna Christiaan Baur
  • Patent number: 7772419
    Abstract: A vinyl ester alkoxycarbonylation process comprising reacting a vinyl ester with carbon monoxide in the presence of an alkanol and a catalyst system. The catalyst system used is obtainable by combining: a) a metal of Group VIII B or a compound thereof, and b) a bidentate ligand of general formula (I) R is a covalent bridging group; R1 together with Q2 to which form an optionally substituted 2-Q2-tricyclo[3.3.1.1{3,7}]decyl group or derivative thereof (2-PA); R2 and R3 independently represent univalent radicals up to 20 atoms or jointly form a bivalent radical of up to 20 atoms; and Q1 and Q2 each independently represent phosphorous, arsenic or antimony. The process is carried out for the production of a 3-hydroxy propanoate ester or acid of formula (II) CH2(OH)CH2C(O)OR28??(II). or for the production of a lactate ester or acid of formula III.
    Type: Grant
    Filed: May 18, 2005
    Date of Patent: August 10, 2010
    Assignee: Lucite International UK Ltd.
    Inventor: Graham Eastham
  • Patent number: 7629491
    Abstract: Disclosed is a hydrocarboxylation process for the production of carboxylic acid from olefins wherein an olefin, water, a Group VIII metal hydrocarboxylation catalyst, an onium salt compound are combined in a reaction zone and contacted with carbon monoxide under hydrocarboxylation conditions of pressure and temperature The process does not require or utilize the addition of a hydrogen halide or an alkyl halide exogenous or extraneous to the hydrocarboxylation process.
    Type: Grant
    Filed: June 26, 2006
    Date of Patent: December 8, 2009
    Assignee: Eastman Chemical Company
    Inventors: Joseph Robert Zoeller, Mary Kathleen Moore
  • Patent number: 7449597
    Abstract: A catalyst useful for carbonylation of olefins has been developed. The catalyst comprises a palladium compound, e.g. PdIm4Cl2, where Im is imidazole and HCl dissolved in water or an alcohol. Carbonylation using this catalyst involves contacting an olefin stream preferably in a solvent such as o-xylene with the catalyst and carbon monoxide at carbonylation conditions to provide a carboxylic acid or an ester. When the catalyst solvent is water one can obtain an acid as the product, but when the catalyst solvent is an alcohol one obtains an ester as the product.
    Type: Grant
    Filed: October 19, 2004
    Date of Patent: November 11, 2008
    Assignee: UOP LLC
    Inventors: Irina Galperin, legal representative, Paul T. Barger, Robert H. Jensen, Albert L. Lapidus, Oleg L. Eliseev, Leonid B. Galperin
  • Patent number: 7446223
    Abstract: The present invention provides: a palladium-containing catalyst which is used for highly selectively or highly productively producing an ?,?-unsaturated aldehyde and an ?,?-unsaturated carboxylic acid from an olefin or in that way producing an ?,?-unsaturated carboxylic acid from an ?,?-unsaturated aldehyde; a method for producing the catalyst; and a method for highly selectively or highly productively producing an ?,?-unsaturated aldehyde and an ?,?-unsaturated carboxylic acid from an olefin or in that way producing an ?,?-unsaturated carboxylic acid from an ?,?-unsaturated aldehyde. In particular, the present invention resides in a palladium-containing catalyst comprising 0.001 to 0.40 mole of tellurium metal to 1.0 mole of palladium metal. This catalyst can be preferably produced by a method having a step of reducing a compound containing palladium atom in its oxidized state and tellurium atom in its oxidized state by a reducing agent.
    Type: Grant
    Filed: June 2, 2005
    Date of Patent: November 4, 2008
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Wataru Ninomiya, Yoshiyuki Himeno, Yuji Fujimori
  • Publication number: 20080269520
    Abstract: A process for the carbonylation of a conjugated diene to a dicarboxylic acid, comprising the steps of (a) contacting a conjugated diene with carbon monoxide and water in the presence of a catalyst system including a source of palladium, a source of an anion and a bidentate phosphine ligand, to obtain a mixture comprising an ethylenically unsaturated acid and reversible diene adducts; (b) separating the obtained reaction mixture into a gaseous stream comprising unreacted conjugated diene and carbon monoxide, a first normally liquid stream comprising at least part of the ethylenically unsaturated acid and the reversible diene adducts, and a second normally liquid stream comprising the catalyst system in admixture with the ethylenically unsaturated acid; (c) recycling the second liquid stream obtained in step (b) to step (a); (d) separating the first liquid product stream obtained in step (b) into a stream comprising the ethylenically unsaturated acid and a stream comprising the reversible diene adducts; and (e)
    Type: Application
    Filed: February 10, 2006
    Publication date: October 30, 2008
    Inventors: Eit Drent, Rene Ernst, Willem Wabe Jager, Cornelia Alida Krom, Timothy Michael Nisbet
  • Publication number: 20070299280
    Abstract: Disclosed is a hydrocarboxylation process for the production of carboxylic acid from olefins wherein an olefin, water, a Group VIII metal hydrocarboxylation catalyst, an onium salt compound are combined in a reaction zone and contacted with carbon monoxide under hydrocarboxylation conditions of pressure and temperature The process does not require or utilize the addition of a hydrogen halide or an alkyl halide exogenous or extraneous to the hydrocarboxylation process.
    Type: Application
    Filed: June 26, 2006
    Publication date: December 27, 2007
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Joseph Robert Zoeller, Mary Kathleen Moore
  • Patent number: 7265240
    Abstract: A process for the carbonylation of ethylenically unsaturated compounds is described. The process comprises reacting an ethylenically unsaturated compound with carbon monoxide in the presence of a source of hydroxyl groups and a catalyst system. The catalyst system is obtained by combining: (a) metal of Group VIII or a compound thereof; and (b) a bidentate phosphine of general formula (I) The carbonylation reaction is carried out at a temperature of between ?30° C. to 49° C. and under a CO partial pressure of less than 30×105 N.
    Type: Grant
    Filed: August 4, 2003
    Date of Patent: September 4, 2007
    Assignee: Lucite International UK Limited
    Inventors: Graham R. Eastham, Cristina Jimenez, David Cole-Hamilton
  • Patent number: 7202382
    Abstract: A process for the production of acetic acid which comprises carbonylating methanol and/or a reactive derivative thereof in one or more reactors in a liquid reaction composition comprising iridium carbonylation catalyst, ruthenium promoter, methyl iodide co-catalyst, methyl acetate, acetic acid and water. The liquid reaction composition from the one or more reactors is passed to one or more flash separation stages to form (i) a vapor fraction comprising condensable components and a low pressure off-gas comprising carbon monoxide and (ii) a liquid fraction comprising iridium carbonylation catalyst, ruthenium promoter and acetic acid solvent. The condensable components are separated from the low pressure off-gas. The concentration of carbon monoxide in the low pressure off-gas is maintained according to the formula: Y>mX+C wherein Y is the molar concentration of carbon monoxide in the low pressure off-gas, X is the concentration in ppm by weight of ruthenium in the liquid reaction composition, m is about 0.
    Type: Grant
    Filed: April 9, 2003
    Date of Patent: April 10, 2007
    Assignee: BP Chemicals Limited
    Inventor: Michael James Muskett
  • Patent number: 7009074
    Abstract: Acetic acid is produced by oxidation of methane with an oxygen-containing gas in the presence of an acid selected from concentrated sulfuric acid and fuming sulfuric acid, a palladium-containing catalyst and a promoter, preferably a copper or iron salt. The addition of a promoter and O2 to a system that includes a palladium-containing catalyst such as PdCl2 increases the rate of acetic acid formation from methane by more than an order of magnitude as compared with prior art and, in addition, inhibits the precipitation of Pd black.
    Type: Grant
    Filed: July 28, 2004
    Date of Patent: March 7, 2006
    Assignees: The Regents of the University of California, BP Chemicals Limited
    Inventors: Mark Zerella, Sudip Mukhopadhyay, Alexis T. Bell, John Glenn Sunley, Sander Gaemers, Philip Howard, Brian Ellis, Andrew Richard Lucy
  • Patent number: 6984668
    Abstract: A liquid-phase chemical reaction medium comprises one or more reactants, optionally in the presence of a reaction product(s) and one or more solvents, diluents or other form of liquid carrier, a catalyst system comprising at least a metal or metal compound and optionally further compounds such as ligands or complexing agents; characterized in that the reaction medium further comprises a polymeric dispersant dissolved in said liquid carrier, said polymeric dispersant being capable of stabilizing a colloidal suspension of particles of said metal or metal compound within the liquid carrier. The presence of the polymeric dispersant enables metal formed by catalyst deactivation to be more easily recovered and recycled. Preferably, the polymeric dispersant has sufficiently acidic or basic functionality to stabilize the colloidal suspension of said metal or metal compound.
    Type: Grant
    Filed: August 2, 2000
    Date of Patent: January 10, 2006
    Assignee: Lucite International UK Limited
    Inventors: Graham Ronald Eastham, Raymond Anthony Hadden, David William Johnson
  • Patent number: 6946574
    Abstract: The present invention relates to a process for the preparation of ?- or ?-unsaturated or saturated carboxylic acids. It relates more particularly to the hydroxycarbonylation of an organic compound comprising a conjugated unsaturation, such as butadiene, by the action of carbon monoxide and water in the presence of a palladium-based catalyst. The carboxylic acids thus obtained are preferably pentenoic acids. According to the invention, the reaction medium after the end of the hydroxycarbonylation stage is treated with hydrogen to reduce the palladium present in the 2+ oxidation state to palladium in the zero oxidation state and the precipitated palladium is recovered.
    Type: Grant
    Filed: December 21, 2001
    Date of Patent: September 20, 2005
    Assignee: Rhodia Polyamide Intermediates
    Inventors: Jean-Pierre Simonato, Pascal Metivier
  • Patent number: 6916954
    Abstract: The invention relates to a catalyst system for carbonylating olefinically or acetylenically unsaturated compounds with carbon monoxide and a nucleophile compound, containing (a) palladium; (b) a phosphine and (c) a polymer containing nitrogen which is soluble in the reaction mixture, with the exception of polyvinyl polymers with aromatic radicals containing nitrogen on the polymer chain. The invention also relates to a method for carbonylation in the presence of one such catalyst system.
    Type: Grant
    Filed: September 25, 2001
    Date of Patent: July 12, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Schäfer, Michael Slany, Edgar Zeller, Michael Röper, Michael Schulz, Günther Grimm
  • Patent number: 6906221
    Abstract: The invention relates to a method for producing acetic acid by oxidizing ethane in fluid bed reactors with high selectivity and high yields.
    Type: Grant
    Filed: October 17, 2001
    Date of Patent: June 14, 2005
    Assignee: Celanese International Corporation
    Inventors: Sabine Zeyss, Uwe Dingerdissen, Manfred Baerns, Dorit Wolf, David Linke
  • Patent number: 6835850
    Abstract: Process for the carbonylation of a conjugated diene by reacting the conjugated diene with carbon monoxide and an hydroxyl group containing compound in the presence of a catalyst system based on: (a) a source of palladium cations, (b) a diphosphine ligand, and (c) a source of anions, wherein the diphosphine ligand is a ligand having the general formula I wherein x1 and x2 represent a cyclic group with at least 5 ring atoms, of which one is a phosphorus atom, and R represents a bivalent aliphatic bridging group, connecting both phosphorus atoms, containing from 2 to 4 atoms in the bridge, which is substituted with at least one substituent or R represents a phenyl group with both phosphorus groups bound to the 1,2-position.
    Type: Grant
    Filed: August 25, 2003
    Date of Patent: December 28, 2004
    Assignee: DSW IP Assets B.V.
    Inventors: Eit Drent, Willem Wabe Jager, Otto Erik Sielcken, Imre Toth
  • Patent number: 6812366
    Abstract: A catalyst useful for oxidation reactions is disclosed. The catalyst is useful for the gas phase oxidation of alkanes, propylene, acrolein, or isopropanol to unsaturated aldehydes or carboxylic acids.
    Type: Grant
    Filed: September 2, 2003
    Date of Patent: November 2, 2004
    Assignee: Rohm and Haas Company
    Inventor: Manhua Lin
  • Publication number: 20040068142
    Abstract: The present invention relates to a process for the preparation of &bgr;- or &ggr;-unsaturated or saturated carboxylic acids.
    Type: Application
    Filed: November 6, 2003
    Publication date: April 8, 2004
    Inventors: Jean-Pierre Simonato, Pascal Metivier
  • Patent number: 6706912
    Abstract: Process for the carbonylation of ethylenically unsaturated compounds having 3 or more carbon atoms by reaction with carbon monoxide and an hydroxyl group containing compound in the presence of a catalyst system. The catalyst system includes (a) a source of palladium cations; (b) a bidentate diphosphine of formula I, R1R2>P—R3—R—R4—P<R5R6  (I) wherein P represents a phosphorus atom; R1, R2, R5 and R6 independently represent the same or different optionally substituted organic groups containing a tertiary carbon atom through which the group is linked to the phosphorus atom; R3 and R4 independently represent optionally substituted alkylene groups and R represents an optionally substituted aromatic group; (c) a source of anions derived from an acid having a pKa less than 3, as measured at 18° C. in an aqueous solution. The process is carried out in the presence of an aprotic solvent.
    Type: Grant
    Filed: March 13, 2001
    Date of Patent: March 16, 2004
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Willem Wabe Jager
  • Patent number: 6646159
    Abstract: Long chain alcohols and acids or other similar oxygenates such as esters are produced from paraffins of similar carbon number by a process comprising paraffin dehydrogenation, carbonylation, and separation. Preferably a mixture of paraffins extending over several carbon numbers and recovered from a kerosene fraction is processed, and unconverted paraffins are recycled to a dehydrogenation zone. Alternative reaction zone configurations, catalyst systems and product recovery methods are disclosed.
    Type: Grant
    Filed: December 21, 2000
    Date of Patent: November 11, 2003
    Assignee: UOP LLC
    Inventors: Lance A. Baird, Leonid B. Galperin, R. Joe Lawson, Robert H. Jensen, Oleg L. Eliseev, Albert L. Lapidus, Aduard G. Ostapenco
  • Patent number: 6613938
    Abstract: A vapor-phase carbonylation method for producing esters and carboxylic acids from reactants comprising lower alkyl alcohols, lower alkyl alcohol generating compositions and mixtures thereof. The method includes contacting the reactants and carbon monoxide in a carbonylation zone of a carbonylation reactor under vapor-phase conditions with a catalyst having a catalytically effective amount of platinum and tin associated with a solid carrier material.
    Type: Grant
    Filed: June 19, 2001
    Date of Patent: September 2, 2003
    Assignee: Eastman Chemical Company
    Inventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
  • Patent number: 6596781
    Abstract: An integrated process for carrying out the production of Fischer-Tropsch products and acetic acid made using the methanol and carbonylation route which utilizes the hydrogen recovered from the methanol production to upgrade the Fischer-Tropsch products.
    Type: Grant
    Filed: May 2, 2002
    Date of Patent: July 22, 2003
    Assignee: Chevron U.S.A. Inc.
    Inventor: William L. Schinski
  • Publication number: 20030092935
    Abstract: In a process for the hydroformylation of ethylenically unsaturated compounds, at least one ethylenically unsaturated compound is reacted with carbon monoxide and hydrogen in the presence of a ligand-metal complex of ruthenium, rhodium, palladium, iridium and/or platinum, where the ligand-metal complex comprises a monophosphine, monophosphinite or monophosphinamidite ligand of the formula I 1
    Type: Application
    Filed: November 7, 2002
    Publication date: May 15, 2003
    Inventor: Wolfgang Ahlers
  • Patent number: 6489506
    Abstract: A process for the liquid-phase carbonylation of ethylene, according to the equation C2H4+CO+ROH→C2H5CO2R, in the presence of a catalyst system comprising a Group VIII metal or compound thereof, a phosphine ligand and a source of anions, and in the presence of water or a source of organic hydroxyl groups, is carried out in conditions in which the molar ratio of ethylene to carbon monoxide in the gaseous phase of the reactor is greater than 1:1. The higher ratios of ethylene to carbon monoxide are beneficial in increasing the turnover number of the catalyst system.
    Type: Grant
    Filed: June 21, 2001
    Date of Patent: December 3, 2002
    Assignee: Lucite International UK Limited
    Inventors: Jean Margaret Pearson, Raymond Anthony Hadden
  • Patent number: 6452043
    Abstract: A method for producing esters, carboxylic acids and mixtures thereof includes contacting, under carbonylation conditions, lower alkyl alcohols, ethers, lower alkyl alcohol derivatives and mixtures thereof and carbon monoxide with a catalyst having a catalytically effective amount a metal selected from iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, tin and mixtures thereof associated with a carbonized polysulfonated divinylbenzene-styrene copolymer matrix. In a preferred aspect of the invention the method is called out under vapor-phase conditions.
    Type: Grant
    Filed: April 5, 2000
    Date of Patent: September 17, 2002
    Assignee: Eastman Chemical Company
    Inventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
  • Patent number: 6388141
    Abstract: The present invention relates to processes for the preparation of oxo products by the hydroformylation of substrates having C═C double bonds using unmodified rhodium catalysts in a reaction mixture essentially consisting of the substrates, the catalyst and carbon dioxide in a supercritical state (scCO2). In particular, the invention relates to such processes for the preparation of products which contain substantial proportions of branched i-oxo products. Further, the invention relates to such processes for the hydroformylation of substrates which do not correspond to the general formula CnH2n. The invention further relates to such processes in which the separation of product and catalyst is effected using the special solvent properties of scCO2.
    Type: Grant
    Filed: January 13, 2000
    Date of Patent: May 14, 2002
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Walter Leitner, Daniel Koch
  • Patent number: 6326455
    Abstract: This invention relates to methods and reactor devices for controlling the oxidation of hydrocarbons to dibasic acids, in the presence of a cobalt catalyst and a monobasic acid, such as acetic acid, by treating the catalyst from the reaction mixture, outside the oxidation zone, after the oxidation has taken place at least partially. In one preferred embodiment, the catalyst is reduced to contain, preferably predominantly and more preferably substantially, cobalt ions in valence II, and at least partially precipitated by de-watering and/or thermal treatment. In a different preferred embodiment, the catalyst in the reaction mixture is first oxidized or maintained, preferably predominantly and more preferably substantially, at valence III, the reaction mixture is de-watered, the catalyst is reduced preferably predominantly and more preferably substantially, to valence II, causing precipitation either spontaneously at a predetermined temperature or after further thermal treatment.
    Type: Grant
    Filed: April 5, 2001
    Date of Patent: December 4, 2001
    Assignee: RPC Inc.
    Inventors: Eustathios Vassiliou, Mark W. Dassel, Ader M. Rostami, Douglas J. Dudgeon, David C. DeCoster
  • Publication number: 20010043895
    Abstract: A method for generating a solution containing rhodium at a concentration of at least 0.01 M and preferably at least 0.20 M, comprising treating solid rhodium iodide or other solid source of rhodium with a reducing agent selected from a source of hydrazine, hydrazine hydrate, hydrazinium salts, organic derivatives of hydrazine, hypophosphorous acid and salts of hypophosphorous acid.
    Type: Application
    Filed: May 11, 2001
    Publication date: November 22, 2001
    Applicant: Haldor Topsoe A/S
    Inventor: Niels C. Schiodt
  • Publication number: 20010023285
    Abstract: This invention relates to methods and reactor devices for controlling the oxidation of hydrocarbons to dibasic acids, in the presence of a cobalt catalyst and a monobasic acid, such as acetic acid, by treating the catalyst from the reaction mixture, outside the oxidation zone, after the oxidation has taken place at least partially. In one preferred embodiment, the catalyst is reduced to contain, preferably predominantly and more preferably substantially, cobalt ions in valence II, and at least partially precipitated by de-watering and/or thermal treatment. In a different preferred embodiment, the catalyst in the reaction mixture is first oxidized or maintained, preferably predominantly and more preferably substantially, at valence III, the reaction mixture is de-watered, the catalyst is reduced preferably predominantly and more preferably substantially, to valence II, causing precipitation either spontaneously at a predetermined temperature or after further thermal treatment.
    Type: Application
    Filed: April 5, 2001
    Publication date: September 20, 2001
    Inventors: Eustathios Vassiliou, Mark W. Dassel, Ader M. Rostami, Douglas J. Dudgeon, David C. DeCoster
  • Patent number: 6284919
    Abstract: A process for the liquid-phase carbonylation of ethylene, according to the equation C2H4+CO+ROH→C2H5CO2R, in the presence of a catalyst system comprising a Group VIII metal or compound thereof, a phosphine ligand and a source of anions, and in the presence of water or a source of organic hydroxyl groups, is carried out in conditions in which the molar ratio of ethylene to carbon monoxide in the gaseous phase of the reactor is greater than 1:1. The higher ratios of ethylene to carbon monoxide are beneficial in increasing the turnover number of the catalyst system.
    Type: Grant
    Filed: September 15, 1999
    Date of Patent: September 4, 2001
    Assignee: Imperial Chemical Industries PLC
    Inventors: Jean Margaret Pearson, Raymond Anthony Hadden
  • Patent number: 6239325
    Abstract: The invention provides process for oxidative dehydrogenation of lower alkanes, by vapor phase oxidative dehydrogenation of C2-C5 lower alkanes in the presence of a catalyst and molecular oxygen to produce the corresponding olefins, in which the catalyst has a composition expressed by a general formula (1) below: A&agr;Sb&bgr;W&ggr;D&dgr;Ox   (1) in which A is at least one metal selected from the group consisting of molybdenum and chromium; Sb is antimony; W is tungsten; O is oxygen; and D is at least one metal selected from the group consisting of V, Nb, Ta, Fe, Co, Ni, Cu, Ag, Zn, B, Tl, Sn, Pb, Te, Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Ce and Sm; &agr;, &bgr;, &ggr;, &dgr; and x denote atomic numbers of A, Sb, W, D and O, respectively, where when &agr;=1, &bgr;=0.5-10, &ggr;=0.1-10 and &dgr;=0-3; and x is a numerical value determined by the state of oxidation of those elements other than oxygen.
    Type: Grant
    Filed: May 18, 1999
    Date of Patent: May 29, 2001
    Assignee: Nippon Shokubai Co Ltd
    Inventors: Nobuji Kishimoto, Etsushige Matsunami
  • Patent number: 6222069
    Abstract: The invention discloses a method for purifying adipic acid in water. More precisely it discloses an improvement in adipic acid crystallization or recrystallization in water, characterised in that the said crystallization or recrystallization is effected in presence of a strong proton acid and/or in the presence of carbon monoxide. This crystallization or recrystallization particularly enables the content of metal catalyst traces in the adipic acid to be reduced.
    Type: Grant
    Filed: March 17, 1999
    Date of Patent: April 24, 2001
    Assignee: Rhodia Fiber and Resin Intermediates
    Inventors: Eric B. Henriet, Philippe Leconte, Carl Patois, Robert Perron
  • Patent number: 6133477
    Abstract: An improved process for the preparation of 3-pentenoic acid by reaction of butadiene with carbon monoxide and water in the presence of a rhodium-containing catalyst and an iodide promoter where carbon monoxide stripping is employed to separate and recover the 3-pentenoic acid product.
    Type: Grant
    Filed: July 23, 1998
    Date of Patent: October 17, 2000
    Assignees: E. I. du Pont de Nemours and Company, DSM N.V.
    Inventor: Harold Stanley Bruner
  • Patent number: 6011171
    Abstract: The present invention provides a process for synthesizing tertiary carboxylic acids or the esters thereof having one or two more carbon atoms than the raw material has, comprising reacting in a strong acid (e.g., sulfuric acid, sulfuric acid-phosphoric acid, hydrogen fluoride, fluorosulfuric acid, boron trifluoride.water complex and trifluoromethanesulfonic acid) a raw material compound (i.e., olefin, alcohol, diene, diol or saturated hydrocarbon) with carbon monoxide in the presence of a specific metal carbonyl catalyst (i.e., platinum carbonyl catalyst, palladium carbonyl catalyst and gold dicarbonyl catalyst).The metal carbonyl catalyst is formed by reacting in a strong acid at least one specific metal compounds (e.g., platinum compound such as platinum (II, IV) oxide, platinum (II, IV) hydroxide, a platinum powder, etc.; palladium compound such as palladium (II, III, IV) oxide, palladium (II) hydroxide, palladium (II) sulfate, palladium (II) carboxylate, a palladium powder, etc.
    Type: Grant
    Filed: November 4, 1997
    Date of Patent: January 4, 2000
    Assignee: Jiro Hiraishi, Director-General, Agency of Industrial Science and Technology
    Inventors: Qiang Xu, Yoshie Souma
  • Patent number: 5977407
    Abstract: Disclosed is a process for the preparation of an aliphatic carbonyl derivative compound having a normal:iso ratio of at least 3, and preferably 4, selected from aliphatic carboxylic acids, alkylesters of aliphatic carboxylic acids and anhydrides of aliphatic carboxylic acids by the hydrocarboxylation of terminal linear olefins in the presence of a catalyst system comprising (1) a rhodium containing compound, (2) a halide promoter selected from iodine, bromine and compounds thereof and (3) a trisubstituted organic compound of a group-15 element, preferably a phosphine or arsine. This process constitutes an improvement over known processes since it provides a one-step, lower pressure, higher reaction rate method of producing carboxylic acid derivatives having an increased normal:iso ratio in the absence of potentially hazardous chlorinated hydrocarbons and aromatic hydrocarbons.
    Type: Grant
    Filed: August 10, 1998
    Date of Patent: November 2, 1999
    Assignee: Eastman Chemical Company
    Inventor: Joseph Robert Zoeller
  • Patent number: 5962732
    Abstract: Process for making 3-pentenoic acid by reacting butadiene with carbon monoxide in the presence of nickel and an iodide source.
    Type: Grant
    Filed: December 17, 1998
    Date of Patent: October 5, 1999
    Assignees: E. I. du Pont de Nemours and Company, DSM N.V.
    Inventor: Patrick Michael Burke
  • Patent number: 5952522
    Abstract: A process is disclosed for the carbonylation of acetylenically unsaturated compounds by reaction with carbon monoxide and a co-reactant in the presence of a catalyst system based on: (a) a source of platinum; (b) a bidentate ligand of the formula R.sup.1 R.sup.2 M.sup.1 -R-M.sup.2 R.sup.3 R.sup.4, wherein M.sup.1 and M.sup.2 independently are P, As or Sb, R represents a bivalent substituted or non-substituted bridging group containing from 1 to 5 atoms in the bridge, R.sup.1 and R.sup.2 together are a substituted or non-substituted bivalent group whereby the two free valencies are linked to M.sup.1, and R.sup.3 and R.sup.4 together are a substituted or non-substituted bivalent group whereby the two free valencies are linked to M.sup.2 or R.sup.3 and R.sup.4 independently are substituted or non-substituted hydrocarbyl groups; and (c) a source of anions.
    Type: Grant
    Filed: December 18, 1996
    Date of Patent: September 14, 1999
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Willem Wabe Jager
  • Patent number: 5919978
    Abstract: This invention relates in part to processes for producing one or more substituted or unsubstituted aldehyde acids or salts, e.g., 5-formylvaleric acid or salt, which comprises subjecting one or more substituted or unsubstituted alkadienes, e.g., butadiene, to hydroxycarbonylation in the presence of a hydroxycarbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and optionally neutralization with a base to produce one or more substituted or unsubstituted unsaturated acids or salts, e.g., pentenoic acid or salt, and subjecting said one or more substituted or unsubstituted unsaturated acids or salts to hydroformylation in the presence of a hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce said one or more substituted or unsubstituted aldehyde acids or salts and/or one or more substituted or unsubstituted epsilon caprolactam precursors.
    Type: Grant
    Filed: April 15, 1997
    Date of Patent: July 6, 1999
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Diane Lee Packett, Thomas Carl Eisenschmid, Michael Allen Brammer, John Michael Maher
  • Patent number: 5908803
    Abstract: The present invention relates to the isolation of a palladium-based catalyst from a mixture in which it is dissolved. More specifically, the invention relates to the isolation of a palladium-based catalyst from a mixture originating from the reaction of hydroxycarbonylation of butadiene to pentenoic acids. It therefore consists of a process for the isolation of at least a portion of the palladium dissolved in a solution also containing at least 3-pentenoic acid, characterized in that the said solution is acidified and stirred with an aqueous solution of hydrochloric acid, so as to obtain two liquid phases including an aqueous phase containing at least a portion of the palladium.
    Type: Grant
    Filed: April 9, 1997
    Date of Patent: June 1, 1999
    Assignee: Rhone-Poulenc Fiber & Resin Intermediates
    Inventors: Philippe Leconte, Carl Patois
  • Patent number: 5866716
    Abstract: A process for selectively preparing a carboxylic acid by reacting an olefin with carbon monoxide in the presence of at least an equimolar amount of water with respect to the olefin at a temperature of from 50.degree. to 150.degree. C.
    Type: Grant
    Filed: August 23, 1996
    Date of Patent: February 2, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Schafer, Arthur Hohn, Ferdinand Lippert
  • Patent number: 5847204
    Abstract: An iridium-based solution is prepared by contacting components in a liquid phase containing (a) a carbonylated iridium compound, (b) hydriodic acid, a precursor of such an acid, or mixture thereof, and (c) a solvent; under a total pressure of between 1 and 10 bar at a temperature not greater than the boiling temperature of the solvent under conditions in which the components are brought into contact. The iridium-based solution can be used as a catalyst for carrying out carbonylation, hydroformylation or isomerization reactions.
    Type: Grant
    Filed: September 27, 1996
    Date of Patent: December 8, 1998
    Assignee: Acetex Chimie
    Inventor: Dominique Nobel