Hydroformylation By Reacting Ethylenically Unsaturated Compound, Carbon Monoxide, And Gaseous Hydrogen Patents (Class 568/451)
  • Patent number: 6455740
    Abstract: Process to separate a group 8-10 metal/phosphite ligand complex from an organic liquid mixture, wherein the following steps are performed (1) contacting the organic liquid with a support having bonded thereto an organophosphine ligand and separating the organic mixture which is poor in group 8-10 metal/phosphite ligand complex, (2) contacting the thus obtained loaded support with an organic solvent and carbon monoxide and separating the thus obtained organic solvent rich in group 8-10 metal/phosphite ligand complex, and (3) reusing the support obtained in step (2) in step (1).
    Type: Grant
    Filed: February 8, 2000
    Date of Patent: September 24, 2002
    Assignee: DSM N.V.
    Inventors: Nicolaas L. H. L. Broeders, Onko J. Gelling, Hendrik F. Martens, Klaas Timmer, Harmen A. Meinema
  • Patent number: 6452055
    Abstract: This invention relates to a process for the catalytic hydroformylation of olefins by reaction of an olefin with hydrogen and carbon monoxide in a liquid, aqueous-organic reaction medium in the presence of a water-soluble hydroformylation catalyst, characterized in that for a substantial period of the hydroformylation reaction, the aqueous-organic medium is present in the form of a microemulsion, which is made up of an oil phase containing the olefin or the olefin and its hydroformylation products, an aqueous phase containing the water-soluble complex catalyst, and a nonionic surfactant.
    Type: Grant
    Filed: January 5, 2001
    Date of Patent: September 17, 2002
    Assignee: Sasol Germany GmbH
    Inventors: Herbert Koch, Reinhard Schomaecker, Marco Haumann
  • Publication number: 20020115892
    Abstract: In a process for the hydroformylation of ethylenically unsaturated compounds, at least one complex or compound of a metal of transition group VIII with at least one bidentate phosphine ligand is used as hydroformylation catalyst and at least one of the reaction steps following the hydroformylation reaction is carried out essentially in the absence of carbon monoxide and hydrogen and in the presence of at least one monodentate phosphine ligand.
    Type: Application
    Filed: February 19, 2002
    Publication date: August 22, 2002
    Inventor: Thomas MacKewitz
  • Patent number: 6437192
    Abstract: A hydroformylation process comprising the steps of: (a) reacting a conjugated C4 to C20 alkadiene with CO and H2 in the presence of a catalyst composition to form a product comprising at least one alkenal wherein said catalyst composition comprises a Group VIII metal or Group VIII metal compound and at least one phosphonite ligand having a structure: wherein R1, R2 and R3 are independently selected from the group consisting of hydrogen, alkyl of 1 to 20 carbon atoms, aralkyl of 7 to 15 carbon atoms and aryl of 6 to 10 carbon atoms, and wherein X1 and X2 are independently selected from the group consisting of a direct bond and alkylidene of 1 to 20 carbon atoms; and then (a) recovering at least one alkenal. The process is particularly useful to produce pentenals from butadiene.
    Type: Grant
    Filed: November 17, 2000
    Date of Patent: August 20, 2002
    Assignee: E. I. Du Pont de Nmeours and Company
    Inventor: Emilio E Bunel
  • Publication number: 20020111517
    Abstract: Ethylenically unsaturated compounds are hydroformylated in the presence of a hydroformylation catalyst comprising at least one complex of a metal of transition group VIII with at least one phosphorus-containing compound as ligand, where this compound contains two groups which contain P atoms and are bound to a molecular skeleton derived from bisphenol A.
    Type: Application
    Filed: February 13, 2002
    Publication date: August 15, 2002
    Inventors: Wolfgang Ahlers, Rocco Paciello, Dieter Vogt, Jarl Ivar van der Vlugt
  • Publication number: 20020111516
    Abstract: The invention provides a process for an improved oxirane hydroformylation catalyst, the improved oxirane hydroformylation catalyst, and a one step process for preparing a 1,3-diol in the presence of such a catalyst.
    Type: Application
    Filed: September 20, 2001
    Publication date: August 15, 2002
    Inventors: John Frederick Knifton, Lynn Henry Slaugh, Paul Richard Weider, Talmadge Gail James, Joseph Broun Powell, Kevin Dale Allen, Timothy Scott Williams
  • Publication number: 20020099243
    Abstract: A process for the hydroformylation of an olefinically unsaturated compound in the liquid phase by reaction, in a reaction section, with carbon monoxide and hydrogen in the presence of a polar phase comprising:
    Type: Application
    Filed: January 24, 2002
    Publication date: July 25, 2002
    Applicant: Institut Francais du Petrole
    Inventors: Frederic Favre, Dominique Commereuc, Helene Olivier-Bourbigou
  • Patent number: 6410799
    Abstract: In a process for hydroformylation of olefinically unsaturated compounds using a catalyst based on cobalt and/or rhodium co-ordinated by at least one ligand selected from the group formed by nitrogen-containing or phosphorus-containing ligands used in a non-aqueous ionic solvent, which catalyst is liquid at a temperature of less than 90° C., in which the aldehydes formed are not or are only slightly soluble and which comprises at least one quaternary ammonium and/or phosphonium cation Q+ and at least one anion A−, the improvement of the invention consists in that in the cobalt and/or rhodium complex, the ligand also carries an ionic function (Q′)+(A′)− where Q and Q′ and/or A and A′ are chemically identical.
    Type: Grant
    Filed: August 23, 2001
    Date of Patent: June 25, 2002
    Assignee: Institut Francais du Petrole
    Inventors: Frédéric Favre, Dominique Commereuc, Hélène Olivier-Bourbigou, Lucien Saussine
  • Patent number: 6403836
    Abstract: The present invention is a process for preparing C4-25 aldehydes by hydroformylating the corresponding C3-24 olefins in the presence of a cobalt hydroformylation catalyst, and catalytically decomposing the formic acid formed in the hydroformylation reaction or in the subsequent catalyst work-up. The aldehydes so produced may be hydrogenated to form alcohols.
    Type: Grant
    Filed: February 22, 2001
    Date of Patent: June 11, 2002
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Alfred Kaizik, Walter Toetsch, Wilfried Bueschken, Felix Gosmann
  • Patent number: 6403837
    Abstract: A process for preparing aldehydes having from 4 to 25 carbon atoms by catalytic hydroformylation of the corresponding olefins, wherein the catalyst used comprises a metal of transition group 8 of the Periodic Table in the presence of a ligand A of the formula I where X=As, Sb or P and R1,R2,R3: are each a substituted or unsubstituted aliphatic, cycloaliphatic or aromatic hydrocarbon radical having from 1 to 50 carbon atoms, where two of the radicals R1, R2, R3 can be covalently linked with the proviso that at least one of the hydrocarbon radicals R1, R2, R3 contains a heteroatom selected from the group consisting of O, S, N, F, Cl, Be, I, Se and Te, and a ligand B of the formula II where R4, R5, R6: are each a substituted or unsubstituted aliphatic, cycloaliphatic or aromatic hydrocarbon having from 1 to 50 carbon atoms, where two of the radicals R4, R5 and R6 can be covalently linked.
    Type: Grant
    Filed: November 9, 2000
    Date of Patent: June 11, 2002
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Dieter Hess, Dirk Roettger, Detlef Selent, Armin Boerner
  • Patent number: 6399834
    Abstract: The present invention relates to methods for producing chiral aldehydes by the enantioselective hydroformylation of prochiral substrates with the aid of a catalyst consisting of a transition metal and a chiral ligand, characterized in that said chiral ligand is a compound of general formula 1 wherein the rings R7-R10 drawn with dotted lines are optional and one or more of rings R1-R6 or R7-R10 are substituted with one or more independently selected substituents of general formula —(CH2)x(CF2)yF(x=0-5; y=1-12) or their branched isomers. In particular, the invention relates to the conducting of the mentioned methods in compressed (liquid or supercritical) carbon dioxide as the reaction medium.
    Type: Grant
    Filed: May 15, 2001
    Date of Patent: June 4, 2002
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Walter Leitner, Sabine Kainz, Daniel Koch, Giancarlo Francio
  • Patent number: 6388142
    Abstract: The invention relates to a method for producing aldehydes by reacting one olefine containing 3 to 12 carbon atoms with hydrogen and carbon monoxide in the presence of one rhodium catalyst. The invention is characterized in that (a) the rhodium catalyst is present in an aqueous phase, whereby the aqueous phase contains i) rhodium in an elemental or bonded form, ii) one trisulfonated triaryl phosphine, and iii) one crown etherl (b) the olefine is present in the reaction conditions in a liquid organic phase which cannot be mixed with the aqueous phase.
    Type: Grant
    Filed: May 16, 2000
    Date of Patent: May 14, 2002
    Assignee: Celanese Chemicals Europe GmbH
    Inventors: Sandra Bogdanovic, Klaus Kuhlein
  • 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
  • Publication number: 20020052531
    Abstract: Supported bis(phosphorus) ligands are disclosed for use in hydroformylation reactions, including the hydroformylation of olefins. Catalysts are formed when the ligands are complexed with a catalytically active metal (e.g., rhodium or iridium).
    Type: Application
    Filed: February 16, 2001
    Publication date: May 2, 2002
    Inventors: Emilio E. Bunel, Patrick M. Burke, Joy D. Druliner, Leo E. Manzer, Kenneth G. Moloy, Manxue Wang
  • Patent number: 6369257
    Abstract: Supported bis(phosphorus) ligands are disclosed for use in hydroformylation reactions, including the hydroformylation of olefins. Catalysts are formed when the ligands are complexed with a catalytically active metal (e.g., rhodium or iridium).
    Type: Grant
    Filed: February 16, 2001
    Date of Patent: April 9, 2002
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Emilio E. Bunel, Patrick Michael Burke, Joe Douglas Druliner, Leo Ernest Manzer, Kenneth Gene Moloy, Manxue Wang
  • Patent number: 6365783
    Abstract: Provided is a process for producing alcohols or aldehydes by reacting monoolefins with carbon monoxide and hydrogen with less formation of by-products. The process comprises the step of reacting a monoolefin with carbon monoxide and hydrogen in the presence of a cobalt carbonyl catalyst until the conversion of monoolefin reaches 50-90% (the first reaction step), the step of separating unreacted monoolefin from the reaction mixture obtained in the first reaction step (the step of separation of unreacted monoolefin) and the step of reacting the separated unreacted monoolefin with carbon monoxide and hydrogen in the presence of a cobalt carbonyl catalyst (the second reaction step), wherein at least one of the first reaction step and the second reaction step is carried out in the presence of water.
    Type: Grant
    Filed: May 25, 2000
    Date of Patent: April 2, 2002
    Assignee: Kyowa Yuka Co., Ltd.
    Inventors: Yorozu Yokomori, Tsukasa Hayashi, Toshiaki Ogata, Junichi Yamada, Seiji Saito
  • Patent number: 6362354
    Abstract: Phosphonite ligands, catalyst compositions containing such ligands and a hydroformylation process using such catalyst compositions involving a bidentate phosphonite ligand having the structure represented by the following wherein the Ar groups are either the same or different unbridged organic aromatic groups such as substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, mixtures thereof or the like are disclosed. The ligands in combination with a Group VIII metal or Group VIII metal compound are particularly useful in a hydroformylation process for reacting an ethylenically unsaturated compound to produce linear alkenals at high selectivity.
    Type: Grant
    Filed: November 17, 2000
    Date of Patent: March 26, 2002
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Emilio Enrique Bunel, Kathryn E. Schwiebert
  • Publication number: 20020035297
    Abstract: In a process for hydroformylation of olefinically unsaturated compounds using a catalyst based on cobalt and/or rhodium coordinated by at least one ligand selected from the group formed by nitrogen-containing or phosphorus-containing ligands used in a non-aqueous ionic solvent, which catalyst is liquid at a temperature of less than 90° C., in which the aldehydes formed are not or are only slightly soluble and which comprises at least one quaternary ammonium and/or phosphonium cation Q+ and at least one anion A−, the improvement of the invention consists in that in the cobalt and/or rhodium complex, the ligand also carries an ionic function (Q′)+(A′)− where Q and Q′ and/or A and A′ are chemically identical.
    Type: Application
    Filed: August 23, 2001
    Publication date: March 21, 2002
    Applicant: Institut Francais du Petrole
    Inventors: Frederic Favre, Dominique Commereuc, Helene Olivier-Bourbigou, Lucien Saussine
  • Publication number: 20020019562
    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: Application
    Filed: December 21, 2000
    Publication date: February 14, 2002
    Inventors: Lance A. Baird, Leonid B. Galperin, R. Joe Lawson, Robert H. Jensen, Oleg L. Eliseev, Albert L. Lapidus, Aduard G. Ostapenco
  • Publication number: 20020013503
    Abstract: A process for hydroformylatiog acyclic monoethylenically unsaturated compounds to corresponding terminal aldehydes using a Group VIII transition metal and selected multidentate phosphite ligands.
    Type: Application
    Filed: July 26, 2001
    Publication date: January 31, 2002
    Inventors: Emilio E. Bunel, Helen S.M. Lu, Kenneth Gene Moloy, Shawn H. Phillips, Kathryn E. Schweibert, Wilson Tam, Nora Radu
  • Patent number: 6339174
    Abstract: A catalyst composition comprising a) more than 70% by weight of a polyethylene glycol of the formula H—(OCH2—CH2)n—OH, where n is an integer of 3 to 16 and the number average molecular weight is less than 650 b) rhodium in elemental form or bound form and c) 2 to 25% by weight of water soluble sulfonated triarylphosphine ligand having 1 to 2 phophorus atoms and not more than 25% by weight of water based on the total amount of the catalyst and its use for the hydroformylation of olefins to aldehydes is described.
    Type: Grant
    Filed: May 16, 2000
    Date of Patent: January 15, 2002
    Assignee: Celanese Chemicals Europe GmbH
    Inventor: Sandra Bogdanovic
  • Publication number: 20020002310
    Abstract: In a process for preparing aldehydes and/or alcohols having from 6 to 30 carbon atoms by hydroformylation of olefins by means of synthesis gas in the presence of a catalyst at from 120° C. to 210° C. and pressures of from 100 to 400 bar, a reaction mixture comprising olefins, synthesis gas and catalyst or catalyst precursor is, according to the present invention, introduced at high velocity into a high-pressure reactor (10) via a nozzle (16) having an adjustable flow cross section.
    Type: Application
    Filed: May 31, 2001
    Publication date: January 3, 2002
    Inventors: Armin Volker Grenacher, Hans-Georg Hein, Hans Stepp, Hans-Jurgen Frohlich, Willi Schonmann, Gerhard Borchert
  • Patent number: 6331656
    Abstract: In a process for the hydroformylation of olefins having from 12 to 100 carbon atoms in the presence of a cobalt carbonyl catalyst at pressures of from 100 to 400 bar and at from 100 to 200° C., depressurization and recovery of the cobalt catalyst by extraction with an aqueous acid solution in the presence of atmospheric oxygen, (a) the extraction is carried out in the presence of a polymeric emulsion breaker selected from the group consisting of alkoxylated compounds containing amino, imino or OH groups, and (b) to achieve complete phase separation in the organic phase still containing small amounts of aqueous phase, the formation of relatively large droplets of the dispersed aqueous phase is effected in a coalescence stage.
    Type: Grant
    Filed: March 4, 1999
    Date of Patent: December 18, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinrich-Josef Blankertz, Armin Volker Grenacher, Friedrich Sauer, Harald Schwahn, Willi Schönmann, Michael Röper
  • Publication number: 20010044556
    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.
    Type: Application
    Filed: March 13, 2001
    Publication date: November 22, 2001
    Inventors: Eit Drent, Willem Wabe Jager
  • Patent number: 6310260
    Abstract: This invention relates to a process for separating one or more organophosphorus ligand degradation products, one or more reaction byproducts and one or more products from a continuously generated reaction product fluid comprising one or more unreacted reactants, a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more organophosphorus ligand degradation products, said one or more reaction byproducts, said one or more products, one or more polar solvents and one or more nonpolar solvents by phase separation wherein (i) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more products is expressed by a partition coefficient ratio Ef1 which is a value greater than about 2.5, (ii) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more organophosphorus ligand degradation products is expressed by a partition coefficient ratio Ef2 which is a value greater than about 2.
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: October 30, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John Nicholas Argyropoulos, Jeffrey Scott Kanel, Michael Leo Tulchinsky, David James Miller, Donald Lee Morrison, Paul Foley, David Robert Bryant, Ailene Gardner Phillips, Brian Michael Roesch, John Robert Briggs, Max Min Lee, John Michael Maher
  • Patent number: 6310261
    Abstract: The invention relates to a method for the production of aldehydes or aldehydes and alcohols by hydroformylation of olefins in the presence of a complexing catalyst homogeneously dissolved in a reaction mixture, containing a metal of Group VIIIa of the periodic table of the elements and a phosphorus-free, polydentate nitrogen compound suitable for complex formation as ligand at temperatures ranging from 50 to 100° C.
    Type: Grant
    Filed: July 3, 2000
    Date of Patent: October 30, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernhard Geissler, Michael Röper, Edgar Zeller, Rocco Paciello, Jürgen Decker, Hartwig Voss, Norbert Mahr
  • Patent number: 6307107
    Abstract: A process for hydroformylatiog acyclic monoethylenically unsaturated compounds to corresponding terminal aldehydes using a Group VIII transition metal and selected multidentate phosphite ligands.
    Type: Grant
    Filed: September 20, 1999
    Date of Patent: October 23, 2001
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Emilio E. Bunel, Helen S. M. Lu, Kenneth Gene Moloy, Shawn H. Phillips, Kathryn E. Schwiebert, Wilson Tam, Nora Radu
  • Patent number: 6307108
    Abstract: This invention relates to a process for separating one or more organophosphorus ligand degradation products, one or more reaction byproducts and one or more formylester products from a reaction product fluid comprising one or more unreacted unsaturated ester reactants, a metal-organophoshorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more organophosphorus ligand degradation products, said one or more reaction byproducts, said one or more products, a nonpolar solvent and a polar solvent by phase separation wherein (i) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more products is expressed by a partition coefficient ratio Ef1 which is a value greater than about 2.5 (ii) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more organophosphorus ligand degradation products is expressed by a partition coefficient ratio Ef2 which is a value greater than about 2.
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: October 23, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John Nicholas Argyropoulos, Jeffrey Scott Kanel, Michael Leo Tulchinsky, David James Miller, Donald Lee Morrison, Paul Foley, David Robert Bryant
  • Patent number: 6307109
    Abstract: This invention relates to a process for separating one or more products from a reaction product fluid comprising a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more products, one or more nonpolar reaction solvents and one or more polar reaction solvents, in which said reaction product fluid exhibits phase behavior depicted by FIG. 1, wherein said process comprises (1) supplying said reaction product fluid from a reaction zone to a separation zone, (2) controlling concentration of said one or more nonpolar reaction solvents and said one or more polar reaction solvents, temperature and pressure in said separation zone sufficient to obtain by phase separation two immiscible liquid phases depicted by regions 2, 4 and 6 of FIG. 1 comprising a polar phase and a nonpolar phase and to prevent or minimize formation of three immiscible liquid phases depicted by region 5 of FIG. 1 and one homogeneous liquid phase depicted by regions 1, 3 and 7 of FIG.
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: October 23, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Jeffrey Scott Kanel, David Robert Bryant, Brian Michael Roesch, Ailene Gardner Phillips
  • Patent number: 6307110
    Abstract: This invention relates to a process for separating one or more organophosphorus ligand degradation products, one or more reaction byproducts and one or more products from a continuously generated reaction product fluid comprising one or more unreacted reactants, a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more organophosphorus ligand degradation products, said one or more reaction byproducts, said one or more products, one or more nonpolar solvents and one or more polar solvents by phase separation wherein (i) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more products is expressed by a partition coefficient ratio Ef1which is a value greater than about 2.5, (ii) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more organophosphorus ligand degradation products is expressed by a partition coefficient ratio Ef2 which is a value greater than about 2.
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: October 23, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John Nicholas Argyropoulos, Jeffrey Scott Kanel, Michael Leo Tulchinsky, David James Miller, Donald Lee Morrison, Paul Foley, David Robert Bryant, Ailene Gardner Phillips, Brian Michael Roesch, John Robert Briggs, Max Min Lee, John Michael Maher
  • Patent number: 6303830
    Abstract: This invention relates to a process for separating one or more organophosphorus ligand degradation products, one or more reaction byproducts and one or more formylester products from a reaction product fluid comprising one or more unreacted unsaturated ester reactants, a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more organophosphorus ligand degradation products, said one or more reaction byproducts, said one or more products, a polar solvent and a nonpolar solvent by phase separation wherein(i) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more products is expressed by a partition coefficient ratio Ef1 which is a value greater than about 2.5, (ii) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more organophosphorus ligand degradation products is expressed by a partition coefficient ratio Ef2 which is a value greater than about 2.
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: October 16, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John Nicholas Argyropoulos, Jeffrey Scott Kanel, Michael Leo Tulchinsky, David James Miller, Donald Lee Morrison, Paul Foley, David Robert Bryant
  • Patent number: 6303829
    Abstract: This invention relates to a process for separating one or more products from a reaction product fluid comprising a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more products, one or more nonpolar reaction solvents and one or more polar reaction solvents, wherein said process comprises (1) subjecting said reaction product fluid to fractional countercurrent extraction with at least two immiscible extraction solvents, said at least two immiscible extraction solvents comprising at least one nonpolar extraction solvent and at least one polar extraction solvent, to obtain a nonpolar phase comprising said metal-organophosphorus ligand complex catalyst, said optionally free organophosphorus ligand, said one or more nonpolar reaction solvents and said at least one nonpolar extraction solvent and a polar phase comprising said one or more products, said one or more polar reaction solvents and said at least one polar extraction solvent, and (2) recovering said polar
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: October 16, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Jeffrey Scott Kanel, John Nicholas Argyropoulos, Ailene Gardner Phillips, Brian Michael Roesch, John Robert Briggs, Max Min Lee, John Michael Maher, David Robert Bryant
  • Patent number: 6294700
    Abstract: This invention relates to a process for separating one or more products from a reaction product fluid comprising a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more products, one or more polar reaction solvents and one or more nonpolar reaction solvents, wherein said process comprises (1) subjecting said reaction product fluid to fractional countercurrent extraction with at least two immiscible extraction solvents, said at least two immiscible extraction solvents comprising at least one polar extraction solvent and at least one nonpolar extraction solvent, to obtain a polar phase comprising said metal-organophosphorus ligand complex catalyst, said optionally free organophosphorus ligand, said one or more polar reaction solvents and said at least one polar extraction solvent and a nonpolar phase comprising said one or more products, said one or more nonpolar reaction solvents and said at least one nonpolar extraction solvent, and (2) recovering said nonpo
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: September 25, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Jeffrey Scott Kanel, John Nicholas Argyropoulos, Ailene Gardner Phillips, Brian Michael Roesch, John Robert Briggs, Max Min Lee, John Michael Maher, David Robert Bryant
  • Publication number: 20010023306
    Abstract: The present invention is a process for preparing C4-25 aldehydes by hydroformylating the corresponding C3-24 olefins in the presence of a cobalt hydroformylation catalyst, and catalytically decomposing the formic acid formed in the hydroformylation reaction or in the subsequent catalyst work-up. The aldehydes so produced may be hydrogenated to form alcohols.
    Type: Application
    Filed: February 22, 2001
    Publication date: September 20, 2001
    Applicant: OXENO Olefinchemie GmbH
    Inventors: Alfred Kaizik, Walter Toetsch, Wilfried Bueschken, Felix Gosmann
  • Patent number: 6291717
    Abstract: A process for producing an aldehyde, which comprises a reaction step of producing an aldehyde by reacting an olefinic compound with carbon monoxide and hydrogen in the presence of a rhodium complex catalyst comprising at least rhodium and an organic phosphite in a reaction zone, a separation step of obtaining a catalyst solution containing the rhodium complex catalyst by separating the aldehyde from a reaction solution taken from the reaction zone, and a recycling step of recycling the catalyst solution into the reaction zone, wherein the aldehyde is separated from the reaction solution in such a manner as to make an aldehyde concentration from 0.5 to 99 wt % in the catalyst solution.
    Type: Grant
    Filed: December 10, 1999
    Date of Patent: September 18, 2001
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Masaki Takai, Iwao Nakajima, Tooru Tsukahara, Yoshiyuki Tanaka, Hisao Urata, Akio Nakanishi
  • Patent number: 6278030
    Abstract: An improved process for preparing alcohols by the Oxo process. More particularly this invention relates to an improvement in the hydrogenation step of the Oxo process characterized in the use of certain bulk multimetallic hydrogenation catalysts comprised of at least one Group VIII non-noble metal and at least two Group VIB metals.
    Type: Grant
    Filed: January 14, 2000
    Date of Patent: August 21, 2001
    Assignee: Exxon Chemical Patents, Inc.
    Inventors: Jose Manuel Vargas, Kenneth Lloyd Riley
  • Patent number: 6274774
    Abstract: The invention concerns a process for preparing aldehydes by reacting with hydrogen and carbon monoxide at a temperature of between 20 and 170° C. and a pressure of between 1 and 300 bar an olefinically unsaturated C6-C16 compound in the presence aqueous phase containing rhodium and sulphonated triarylphosphines as catalyst and between 10 and 70 wt % of a compound of formula (1), R(OCH2CH2)nOR1, R standing for hydrogen, a straight-chain or branched C1-C4 alkyl group or a C1-C4 hydroxyalkyl group, R1 standing for hydrogen or a methyl group, and n standing for an integer from 3 to 50.
    Type: Grant
    Filed: August 30, 1999
    Date of Patent: August 14, 2001
    Assignee: Celanese GmbH
    Inventors: Sandra Bogdanovic, Carl-Dieter Frohning, Helmut Bahrmann
  • Patent number: 6274773
    Abstract: Process for the continuous preparation of an alkyl 5-formylvalerate by reacting an alkyl-3-pentenoate with carbon monoxide and hydrogen by hydroformylation using a catalyst system comprising rhodium or iridium and a multidentate organic phosphite ligand according to the general formula: in which n is 2-6, X is an n-valent organic bridging group, and in which the end groups R1-R2 are monovalent aryl groups, wherein the process is carried out in the presence of an acid compound having a pKa between 1 and 12 measured in water at 18° C.
    Type: Grant
    Filed: May 4, 1999
    Date of Patent: August 14, 2001
    Assignees: DSM, E.I. DuPont De Nemours & Co.
    Inventors: Onko J. Gelling, Peter C. Borman
  • Patent number: 6265619
    Abstract: Alcohols suitable for plasticizer ester manufacture and acids are made by cofeeding olefins to oxonation, aldolizing the resulting aldehyde and hydrogenating the resulting unsaturated aldehydes, optionally dehydrating a part of the alcohol thereby made and returning the resulting olefin to oxonation, or oxidizing the aldehydes.
    Type: Grant
    Filed: February 23, 1998
    Date of Patent: July 24, 2001
    Assignee: Exxon Chemical Patents Inc.
    Inventor: Jan Martin de Rijke
  • Patent number: 6265620
    Abstract: Aldehydes are produced by reacting an olefinic compound with carbon monoxide and hydrogen in the presence of a catalyst containing a metal of Group 8 to 10 and a phosphonite compound as a trivalent organic phosphorus compound.
    Type: Grant
    Filed: September 27, 1999
    Date of Patent: July 24, 2001
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hisao Urata, Yasuhiro Wada
  • Patent number: 6252121
    Abstract: This invention relates to a process for separating one or more cyclic products from a reaction product fluid comprising one or more cyclic reactants, a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, a non-polar solvent and said one or more cyclic products, wherein said process comprises: (1) reacting said one or more cyclic reactants in the presence of said metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand and non-polar solvent to form a multiphase reaction product fluid; and (2) separating said multiphase reaction product fluid to obtain a non-polar phase comprising said one or more cyclic reactants, metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand and non-polar solvent and a polar phase comprising said one or more cyclic products.
    Type: Grant
    Filed: July 27, 1999
    Date of Patent: June 26, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John Nicholas Argyropoulos, David Robert Bryant, Michael Leo Tulchinsky, Jeffrey Scott Kanel, Paul Foley, Barry Brent Fish
  • Patent number: 6252123
    Abstract: This invention relates to a process for the separation of a metal complex catalyst and any free ligand which may be present, from a homogeneous organic synthesis reaction mixture using sub-nanoporous, chemically stable membranes having discrete pores which allow organic products and by-products to pass through the membrane as permeate while retaining substantially all of the metal complex catalyst and free ligand, if any, as retentate.
    Type: Grant
    Filed: July 8, 1999
    Date of Patent: June 26, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Jay Fingeret Miller, Joan Ayer Rodberg, Brian Michael Roesch, George Ernest Keller, II, Lisa Evans Curry, Paul Frank Bryan, John Edward Davis, James Charles Hatfield
  • Publication number: 20010003785
    Abstract: Aldehydes are prepared in a hydroformylation apparatus by the multiphase hydroformylation reaction of one or more olefins with hydrogen and carbon monoxide, where the continuous phase contains a solvent mixture and the hydroformylation catalyst is present in the continuous phase, at least one olefin is present in the dispersed phase, and the loading factor of the tube reactor is greater than or equal to 0.8.
    Type: Application
    Filed: November 30, 2000
    Publication date: June 14, 2001
    Applicant: OXENO OLEFINCHEMIE GMBH
    Inventors: Guido Protzmann, Klaus-Diether Wiese, Wilfried Buschken, Dirk Rottger
  • Patent number: 6232263
    Abstract: Disclosed are catalyst compositions comprising one or more transition metals selected from the Group VIII metals and rhenium and one or more chlorophosphite compounds having the general Formula wherein R1 and R2 are aromatic hydrocarbyl radicals. Also disclosed are catalyst solutions comprising one or more the above chlorophosphite compounds, rhodium and a hydroformylation solvent, and hydroformylation processes wherein olefins are contacted with carbon monoxide, hydrogen and the catalyst solution to produce aldehydes.
    Type: Grant
    Filed: June 23, 2000
    Date of Patent: May 15, 2001
    Assignee: Eastman Chemical Company
    Inventors: Ginette Struck Tolleson, Thomas Allen Puckette
  • Patent number: 6229052
    Abstract: Supported bis(phosphorus) ligands are disclosed for use in hydroformylation reactions, including the hydroformylation of olefins. Catalysts are formed when the ligands are complexed with a catalytically active metal (e.g., rhodium or iridium).
    Type: Grant
    Filed: April 14, 1999
    Date of Patent: May 8, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Emilio E. Bunel, Patrick Michael Burke, Joe Douglas Druliner, Leo Ernest Manzer, Kenneth Gene Moloy, Manxue Wang
  • Patent number: 6225508
    Abstract: According to the invention, branched and straight chain alkenes and cycloalkenes with five and more C-atoms are by means of hydroformylation using a novel rhodium-tri-polyethylene glycolate of a polyethylene glycol with an average molecular weight of 320 to 650 as a catalyst with at hydrogen/carbon monoxide pressure of 60 to 200 bar and at a temperature of between 50 and 150° C. converted into branched and straight chain alkanals and cycloalkanals with six and more C-atoms. The reaction is preferably carried out in water or polyethylene glycol or a mixture of the same as a solvent in the heterogeneous phase. The aldehydes obtained are easy to separate from the catalyst in the reaction preparation. Said aldehydes are also obtained with a high level of purity and a high yield.
    Type: Grant
    Filed: February 15, 2000
    Date of Patent: May 1, 2001
    Assignee: Hoechst Research & Technology Deutschland GmbH & Co. KG
    Inventors: Sandra Bogdanovic, Herbert Roesky, Uwe Ritter, Thomas Borrmann
  • Patent number: 6225509
    Abstract: Hydroxybutyraldehyde is formed by hydroformylation of allyl alcohol using a catalyst comprised of a rhodium complex and a ligand such as DIOP, the concentration of CO in the reaction liquid is maintained above about 4.5 mg. mols/liter.
    Type: Grant
    Filed: January 6, 2000
    Date of Patent: May 1, 2001
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Walter S. Dubner, Wilfred Po-sum Shum
  • Patent number: 6225507
    Abstract: A process for the preparation of aldehydes or aldehydes and alcohols by hydroformylation of olefins containing more than 3 carbon atoms, comprising a hydroformylation stage, in which the olefin is hydroformylated under a pressure of form 50 to 1000 bar and at a temperature of from 50° to 180° C. by means of a rhodium catalyst dissolved in a homogenous reaction medium and a catalyst recovery stage comprising extraction of the rhodium catalyst with an aqueous solution of chelating agent, isolation of alcohols and/or aldehyde from the extracted hydroformylation product steam, precarbonylation of the aqueous rhodium-containing extract in the presence of carbon monoxide, synthesis gas as, or a gas mixture containing carbon monoxide under a pressure of from 50 to 1000 bar and at a temperature of from 50° to 180° C.
    Type: Grant
    Filed: August 4, 1998
    Date of Patent: May 1, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernhard Giessler, Heinz-Josef Kneuper, Michael Röper, Rocco Paciello, Knut Oppenländer, Wolfgang Günther
  • Patent number: 6211414
    Abstract: The invention concerns a process for preparing aldehydes by reacting with hydrogen and carbon monoxide at a temperature of between 20 and 170° C. and a pressure of between 1 and 300 bar an olefinically unsaturated C3-C5 compound in the presence of an aqueous phase containing rhodium and sulphonated triarylphosphines as catalyst and between 1 and 35 wt % of a compound of formula (1), R(OCH2CH2)nOR1, R standing for hydrogen, a straight-chain or branched C1-C4 alkyl group or a C1-C4 hydroxyalkyl group, R1 standing for hydrogen or a methyl group, and n standing for an integer from 3 to 50.
    Type: Grant
    Filed: August 31, 1999
    Date of Patent: April 3, 2001
    Assignee: Celanese GmbH
    Inventors: Sandra Bogdanovic, Helmut Bahrmann, Carl-Dieter Frohning, Ernst Wiebus
  • Patent number: 6191063
    Abstract: A catalyst comprising rhodium and a compound of the formula (I) in which m is a number from 1 to 1000; x is a number from 0 to 4; W is a group of the formulae —CH2—CH2—, —CH(CH3)CH2—or —CH2CH(CH3)—; R is hydrogen, a straight-chain or branched C1-C5— alkyl radical; or a group of the formulae where a, b, c, d and e independently of one another are a number from 0 to 1000, at least one of the numbers a, b, c, d and e being greater than 0; R5, R6, R7, R8 and R9 are identical or different and are hydrogen, C1-C5-alkyl or a group of the formula R1 and R2 are identical or different and are a straight-chain, branched or cyclic C1-C30-alkyl radical or C6-10-aryl radical, which is unsubstituted or substituted by from one to five C1-C3-alkyl radicals, and L is C1-C5-alkyl, C1-C5-alkoxy, NO2, NR3R4, where R3 and R4 independently of one another are hydrogen or C1-C4-alkyl, or L is Cl or OH, for hydroformylation re
    Type: Grant
    Filed: July 1, 1999
    Date of Patent: February 20, 2001
    Assignee: Celanese GmbH
    Inventors: Sandra Bogdanovic, Carl-Dieter Frohning, Helmut Bahrmann, Matthias Beller, Steffen Haber, Hans-Jerg Kleiner