Hydroformylation By Reacting Ethylenically Unsaturated Compound, Carbon Monoxide, And Gaseous Hydrogen Patents (Class 568/451)
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Patent number: 6455740Abstract: 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: GrantFiled: February 8, 2000Date of Patent: September 24, 2002Assignee: DSM N.V.Inventors: Nicolaas L. H. L. Broeders, Onko J. Gelling, Hendrik F. Martens, Klaas Timmer, Harmen A. Meinema
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Patent number: 6452055Abstract: 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: GrantFiled: January 5, 2001Date of Patent: September 17, 2002Assignee: Sasol Germany GmbHInventors: Herbert Koch, Reinhard Schomaecker, Marco Haumann
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Publication number: 20020115892Abstract: 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: ApplicationFiled: February 19, 2002Publication date: August 22, 2002Inventor: Thomas MacKewitz
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Patent number: 6437192Abstract: 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: GrantFiled: November 17, 2000Date of Patent: August 20, 2002Assignee: E. I. Du Pont de Nmeours and CompanyInventor: Emilio E Bunel
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Publication number: 20020111517Abstract: 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: ApplicationFiled: February 13, 2002Publication date: August 15, 2002Inventors: Wolfgang Ahlers, Rocco Paciello, Dieter Vogt, Jarl Ivar van der Vlugt
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Publication number: 20020111516Abstract: 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: ApplicationFiled: September 20, 2001Publication date: August 15, 2002Inventors: John Frederick Knifton, Lynn Henry Slaugh, Paul Richard Weider, Talmadge Gail James, Joseph Broun Powell, Kevin Dale Allen, Timothy Scott Williams
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Publication number: 20020099243Abstract: 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: ApplicationFiled: January 24, 2002Publication date: July 25, 2002Applicant: Institut Francais du PetroleInventors: Frederic Favre, Dominique Commereuc, Helene Olivier-Bourbigou
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Patent number: 6410799Abstract: 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: GrantFiled: August 23, 2001Date of Patent: June 25, 2002Assignee: Institut Francais du PetroleInventors: Frédéric Favre, Dominique Commereuc, Hélène Olivier-Bourbigou, Lucien Saussine
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Patent number: 6403836Abstract: 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: GrantFiled: February 22, 2001Date of Patent: June 11, 2002Assignee: Oxeno Olefinchemie GmbHInventors: Alfred Kaizik, Walter Toetsch, Wilfried Bueschken, Felix Gosmann
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Patent number: 6403837Abstract: 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: GrantFiled: November 9, 2000Date of Patent: June 11, 2002Assignee: Oxeno Olefinchemie GmbHInventors: Dieter Hess, Dirk Roettger, Detlef Selent, Armin Boerner
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Patent number: 6399834Abstract: 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: GrantFiled: May 15, 2001Date of Patent: June 4, 2002Assignee: Studiengesellschaft Kohle mbHInventors: Walter Leitner, Sabine Kainz, Daniel Koch, Giancarlo Francio
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Patent number: 6388142Abstract: 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: GrantFiled: May 16, 2000Date of Patent: May 14, 2002Assignee: Celanese Chemicals Europe GmbHInventors: Sandra Bogdanovic, Klaus Kuhlein
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Patent number: 6388141Abstract: 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: GrantFiled: January 13, 2000Date of Patent: May 14, 2002Assignee: Studiengesellschaft Kohle mbHInventors: Walter Leitner, Daniel Koch
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Publication number: 20020052531Abstract: 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: ApplicationFiled: February 16, 2001Publication date: May 2, 2002Inventors: Emilio E. Bunel, Patrick M. Burke, Joy D. Druliner, Leo E. Manzer, Kenneth G. Moloy, Manxue Wang
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Patent number: 6369257Abstract: 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: GrantFiled: February 16, 2001Date of Patent: April 9, 2002Assignee: E. I. du Pont de Nemours and CompanyInventors: Emilio E. Bunel, Patrick Michael Burke, Joe Douglas Druliner, Leo Ernest Manzer, Kenneth Gene Moloy, Manxue Wang
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Patent number: 6365783Abstract: 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: GrantFiled: May 25, 2000Date of Patent: April 2, 2002Assignee: Kyowa Yuka Co., Ltd.Inventors: Yorozu Yokomori, Tsukasa Hayashi, Toshiaki Ogata, Junichi Yamada, Seiji Saito
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Patent number: 6362354Abstract: 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: GrantFiled: November 17, 2000Date of Patent: March 26, 2002Assignee: E. I. du Pont de Nemours and CompanyInventors: Emilio Enrique Bunel, Kathryn E. Schwiebert
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Publication number: 20020035297Abstract: 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: ApplicationFiled: August 23, 2001Publication date: March 21, 2002Applicant: Institut Francais du PetroleInventors: Frederic Favre, Dominique Commereuc, Helene Olivier-Bourbigou, Lucien Saussine
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Publication number: 20020019562Abstract: 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: ApplicationFiled: December 21, 2000Publication date: February 14, 2002Inventors: Lance A. Baird, Leonid B. Galperin, R. Joe Lawson, Robert H. Jensen, Oleg L. Eliseev, Albert L. Lapidus, Aduard G. Ostapenco
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Publication number: 20020013503Abstract: A process for hydroformylatiog acyclic monoethylenically unsaturated compounds to corresponding terminal aldehydes using a Group VIII transition metal and selected multidentate phosphite ligands.Type: ApplicationFiled: July 26, 2001Publication date: January 31, 2002Inventors: Emilio E. Bunel, Helen S.M. Lu, Kenneth Gene Moloy, Shawn H. Phillips, Kathryn E. Schweibert, Wilson Tam, Nora Radu
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Patent number: 6339174Abstract: 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: GrantFiled: May 16, 2000Date of Patent: January 15, 2002Assignee: Celanese Chemicals Europe GmbHInventor: Sandra Bogdanovic
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Publication number: 20020002310Abstract: 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: ApplicationFiled: May 31, 2001Publication date: January 3, 2002Inventors: Armin Volker Grenacher, Hans-Georg Hein, Hans Stepp, Hans-Jurgen Frohlich, Willi Schonmann, Gerhard Borchert
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Patent number: 6331656Abstract: 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: GrantFiled: March 4, 1999Date of Patent: December 18, 2001Assignee: BASF AktiengesellschaftInventors: Heinrich-Josef Blankertz, Armin Volker Grenacher, Friedrich Sauer, Harald Schwahn, Willi Schönmann, Michael Röper
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Publication number: 20010044556Abstract: 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: ApplicationFiled: March 13, 2001Publication date: November 22, 2001Inventors: Eit Drent, Willem Wabe Jager
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Patent number: 6310260Abstract: 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: GrantFiled: March 15, 2000Date of Patent: October 30, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: 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
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Patent number: 6310261Abstract: 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: GrantFiled: July 3, 2000Date of Patent: October 30, 2001Assignee: BASF AktiengesellschaftInventors: Bernhard Geissler, Michael Röper, Edgar Zeller, Rocco Paciello, Jürgen Decker, Hartwig Voss, Norbert Mahr
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Patent number: 6307107Abstract: A process for hydroformylatiog acyclic monoethylenically unsaturated compounds to corresponding terminal aldehydes using a Group VIII transition metal and selected multidentate phosphite ligands.Type: GrantFiled: September 20, 1999Date of Patent: October 23, 2001Assignee: E.I. du Pont de Nemours and CompanyInventors: Emilio E. Bunel, Helen S. M. Lu, Kenneth Gene Moloy, Shawn H. Phillips, Kathryn E. Schwiebert, Wilson Tam, Nora Radu
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Patent number: 6307108Abstract: 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: GrantFiled: March 15, 2000Date of Patent: October 23, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: John Nicholas Argyropoulos, Jeffrey Scott Kanel, Michael Leo Tulchinsky, David James Miller, Donald Lee Morrison, Paul Foley, David Robert Bryant
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Patent number: 6307109Abstract: 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: GrantFiled: March 15, 2000Date of Patent: October 23, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Jeffrey Scott Kanel, David Robert Bryant, Brian Michael Roesch, Ailene Gardner Phillips
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Patent number: 6307110Abstract: 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: GrantFiled: March 15, 2000Date of Patent: October 23, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: 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
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Patent number: 6303830Abstract: 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: GrantFiled: March 15, 2000Date of Patent: October 16, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: John Nicholas Argyropoulos, Jeffrey Scott Kanel, Michael Leo Tulchinsky, David James Miller, Donald Lee Morrison, Paul Foley, David Robert Bryant
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Patent number: 6303829Abstract: 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 polarType: GrantFiled: March 15, 2000Date of Patent: October 16, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Jeffrey Scott Kanel, John Nicholas Argyropoulos, Ailene Gardner Phillips, Brian Michael Roesch, John Robert Briggs, Max Min Lee, John Michael Maher, David Robert Bryant
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Patent number: 6294700Abstract: 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 nonpoType: GrantFiled: March 15, 2000Date of Patent: September 25, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Jeffrey Scott Kanel, John Nicholas Argyropoulos, Ailene Gardner Phillips, Brian Michael Roesch, John Robert Briggs, Max Min Lee, John Michael Maher, David Robert Bryant
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Publication number: 20010023306Abstract: 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: ApplicationFiled: February 22, 2001Publication date: September 20, 2001Applicant: OXENO Olefinchemie GmbHInventors: Alfred Kaizik, Walter Toetsch, Wilfried Bueschken, Felix Gosmann
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Patent number: 6291717Abstract: 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: GrantFiled: December 10, 1999Date of Patent: September 18, 2001Assignee: Mitsubishi Chemical CorporationInventors: Masaki Takai, Iwao Nakajima, Tooru Tsukahara, Yoshiyuki Tanaka, Hisao Urata, Akio Nakanishi
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Patent number: 6278030Abstract: 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: GrantFiled: January 14, 2000Date of Patent: August 21, 2001Assignee: Exxon Chemical Patents, Inc.Inventors: Jose Manuel Vargas, Kenneth Lloyd Riley
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Patent number: 6274774Abstract: 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: GrantFiled: August 30, 1999Date of Patent: August 14, 2001Assignee: Celanese GmbHInventors: Sandra Bogdanovic, Carl-Dieter Frohning, Helmut Bahrmann
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Patent number: 6274773Abstract: 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: GrantFiled: May 4, 1999Date of Patent: August 14, 2001Assignees: DSM, E.I. DuPont De Nemours & Co.Inventors: Onko J. Gelling, Peter C. Borman
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Patent number: 6265619Abstract: 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: GrantFiled: February 23, 1998Date of Patent: July 24, 2001Assignee: Exxon Chemical Patents Inc.Inventor: Jan Martin de Rijke
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Patent number: 6265620Abstract: 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: GrantFiled: September 27, 1999Date of Patent: July 24, 2001Assignee: Mitsubishi Chemical CorporationInventors: Hisao Urata, Yasuhiro Wada
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Patent number: 6252121Abstract: 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: GrantFiled: July 27, 1999Date of Patent: June 26, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: John Nicholas Argyropoulos, David Robert Bryant, Michael Leo Tulchinsky, Jeffrey Scott Kanel, Paul Foley, Barry Brent Fish
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Patent number: 6252123Abstract: 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: GrantFiled: July 8, 1999Date of Patent: June 26, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: 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
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Publication number: 20010003785Abstract: 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: ApplicationFiled: November 30, 2000Publication date: June 14, 2001Applicant: OXENO OLEFINCHEMIE GMBHInventors: Guido Protzmann, Klaus-Diether Wiese, Wilfried Buschken, Dirk Rottger
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Patent number: 6232263Abstract: 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: GrantFiled: June 23, 2000Date of Patent: May 15, 2001Assignee: Eastman Chemical CompanyInventors: Ginette Struck Tolleson, Thomas Allen Puckette
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Patent number: 6229052Abstract: 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: GrantFiled: April 14, 1999Date of Patent: May 8, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: Emilio E. Bunel, Patrick Michael Burke, Joe Douglas Druliner, Leo Ernest Manzer, Kenneth Gene Moloy, Manxue Wang
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Patent number: 6225508Abstract: 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: GrantFiled: February 15, 2000Date of Patent: May 1, 2001Assignee: Hoechst Research & Technology Deutschland GmbH & Co. KGInventors: Sandra Bogdanovic, Herbert Roesky, Uwe Ritter, Thomas Borrmann
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Patent number: 6225509Abstract: 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: GrantFiled: January 6, 2000Date of Patent: May 1, 2001Assignee: ARCO Chemical Technology, L.P.Inventors: Walter S. Dubner, Wilfred Po-sum Shum
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Patent number: 6225507Abstract: 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: GrantFiled: August 4, 1998Date of Patent: May 1, 2001Assignee: BASF AktiengesellschaftInventors: Bernhard Giessler, Heinz-Josef Kneuper, Michael Röper, Rocco Paciello, Knut Oppenländer, Wolfgang Günther
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Patent number: 6211414Abstract: 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: GrantFiled: August 31, 1999Date of Patent: April 3, 2001Assignee: Celanese GmbHInventors: Sandra Bogdanovic, Helmut Bahrmann, Carl-Dieter Frohning, Ernst Wiebus
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Patent number: 6191063Abstract: 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 reType: GrantFiled: July 1, 1999Date of Patent: February 20, 2001Assignee: Celanese GmbHInventors: Sandra Bogdanovic, Carl-Dieter Frohning, Helmut Bahrmann, Matthias Beller, Steffen Haber, Hans-Jerg Kleiner