Hydroformylation By Reacting Ethylenically Unsaturated Compound, Carbon Monoxide, And Gaseous Hydrogen Patents (Class 568/451)
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Patent number: 6770791Abstract: Disclosed is an olefin containing stream from an oxygenate to olefin process, and a process for making olefin dimer and oligomer product from the olefin containing stream using a nickel based oligomerization catalyst. The dimer/oligomer product is optionally converted to hydroformylated product. The olefin containing stream that is used to make the higher olefin product has low levels of impurities including nitrogen, sulfur and/or chlorine.Type: GrantFiled: April 29, 2003Date of Patent: August 3, 2004Assignee: ExxonMobil Chemical Patents Inc.Inventors: Georges Mathys, John Stephen Godsmark, Marcel Janssen, Luc Roger Martens, Hubertus Joseph Beckers, Eddy Theophile Andrea Van Driessche, Raphael Frans Ivo Caers, John Richard Shutt
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Patent number: 6768028Abstract: A composition and a process for using the composition in hydroformylation of unsaturated organic compounds are disclosed. The composition comprises a Group VIII metal and a phosphite-containing polymer having repeat units derived from (1) a carbonyl compound, a monomer, and phosphochloridite; (2) phosphorus trichloride, a polyhydric alcohol, and an aromatic diol; or (3) combinations of (1) and (2). The process comprises contacting an unsaturated compound, in the presence of the composition disclosed herein, with a fluid comprising hydrogen.Type: GrantFiled: May 17, 2002Date of Patent: July 27, 2004Inventors: Wilson Tam, Kathryn Eileen Schwiebert, Joe Douglas Druliner
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Publication number: 20040138507Abstract: A process for the hydroformylation of olefins to produce oxygenated compounds comprises reacting together an olefin, carbon monoxide and hydrogen at elevated temperature and pressure in the presence of a rhodium-containing hydroformylation catalyst and an amount of cobalt or a cobalt compound not exceeding that corresponding to 100 ppm w/w of cobalt metal on the olefin. The reaction is carried out homogeneously and in the absence of a phosphorus-containing organic ligand. The addition of cobalt or a cobalt compound facilitates the reaction of less reactive olefin feedstocks or feedstocks which contain certain impurities.Type: ApplicationFiled: February 24, 2004Publication date: July 15, 2004Inventors: Frank Alfred Kirk, David Hugh Miles, Gordon Howard Whitfield
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Patent number: 6756411Abstract: A process for producing oxygenated products from an olefin-rich feedstock comprise reacting, in a hydroformylation stage, a Fischer-Tropsch derived olefinic product comprising linear and methyl branched olefins, with carbon monoxide and hydrogen in the presence of a catalytically effective quantity of a hydroforhylation catalyst and under hydroformylation reaction conditions, to produce oxygenated products comprising linear and methyl branched aldehydes and/or alcohols. The Fischer-Tropsch derived olefinic product is that obtained by subjecting a synthesis gas comprising carbon monoxide (CO) and hydrogen (H2) to Fischer-Tropsch reaction conditions in the presence of a Fischer-Tropsch catalyst.Type: GrantFiled: October 28, 2002Date of Patent: June 29, 2004Assignee: Sasol Technology (Proprietary) LimitedInventors: Mark Justin Betts, Mark Eberhard Dry, Arie Geertsema, Gerhardus Johannes Hendricus Rall
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Publication number: 20040122262Abstract: A hydroformylation process comprising reacting a compound having at least one olefinic carbon-to-carbon bond with hydrogen and carbon monoxide in the presence of a cobalt catalyst, the hydroformylation process being carried out in one or more reactors, at least one of which comprises a gas cap region and a liquid-containing region while in use, characterized in that a sulphur-containing additive is present on the inside walls of the gas cap region of the at least one-reactor which comprises a gas cap region and a liquid-containing region. The sulphur-containing additive suppresses the formation of methane during the hydroformylation process.Type: ApplicationFiled: October 31, 2003Publication date: June 24, 2004Inventors: Robert Hardy Ellison, Eric Kragtwijk, Frederik Hendrik Van Der Steen
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Patent number: 6753450Abstract: The invention relates to a process for the preparation of aldehydes in which at least one compound containing a vinyl or vinylidene group is reacted with carbon monoxide and hydrogen in the presence of a source of a metal from sub-group VIII and in the presence of a bidentate diphosphine ligand, where the diphosphine ligand has the general formula I in which A together with the phosphorus atom to which it is bonded, in each case forms a 2-phosphatricyclo[3.3.1.1{3,7}]decyl radical, in which one or more non-adjacent carbon atoms may be replaced by oxygen atoms and which is substituted or unsubstituted, and X is a bridging chain having 1 to 10 carbon atoms, and the molar ratio between the diphosphine ligand and the metal is at least 5. The process gives predominantly n-aldehydes.Type: GrantFiled: November 7, 2002Date of Patent: June 22, 2004Assignee: BASF AktiengesellschaftInventors: Wolfgang Ahlers, Michael Slany
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Patent number: 6747179Abstract: A method for carrying out a catalysis reaction in carbon dioxide comprising contacting a fluid mixture with a catalyst bound to a polymer, the fluid mixture comprising at least one reactant and carbon dioxide, wherein the reactant interacts with the catalyst to form a reaction product. A composition of matter comprises carbon dioxide and a polymer and a reactant present in the carbon dioxide. The polymer has bound thereto a catalyst at a plurality of chains along the length of the polymer, and wherein the reactant interacts with the catalyst to form a reaction product.Type: GrantFiled: August 18, 2000Date of Patent: June 8, 2004Assignees: North Carolina State University, The University of North Carolina at Chapel Hill, Regents of University of CaliforniaInventors: Joseph M. DeSimone, Eva Birnbaum, Ruben G. Carbonell, Stephanie Crette, James B. McClain, T. Mark McCleskey, Kimberly R. Powell, Timothy J. Romack, William Tumas
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Publication number: 20040097761Abstract: A microemulsion containing water, a densified fluid, a surfactant, and an organometallic catalyst is used to catalyze chemical reactions. The organometallic catalyst preferably has substantial solubility in the water phase of the microemulsion. Separation of reaction products from the microemulsion is facilitated by removal of the densified fluid.Type: ApplicationFiled: August 15, 2003Publication date: May 20, 2004Inventors: Can Erkey, Xing Dong
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Patent number: 6723884Abstract: Olefins having from 6 to 20 carbon atoms are hydroformylated by means of a continuous process in which a) an aqueous cobalt(II) salt solution is brought into intimate contact with hydrogen and carbon monoxide to form a hydroformylation-active cobalt catalyst, and the aqueous phase comprising the cobalt catalyst is brought into intimate contact with the olefins and, if desired, an organic solvent and also hydrogen and carbon monoxide in at least one reaction zone where the cobalt catalyst is extracted into the organic phase and the olefins are hydroformylated, b) the output from the reaction zone is treated with oxygen in the presence of acidic aqueous cobalt(II) salt solution, with the cobalt catalyst being decomposed to form cobalt(II) salts and these being backextracted into the aqueous phase; and the phases are subsequently separated, c) the aqueous cobalt(II) salt solution is recirculated in unchanged form to step a), wherein the cobalt(II) salt solution has a concentration of from 1.1 to 1.Type: GrantFiled: February 19, 2002Date of Patent: April 20, 2004Assignee: BASF AktiengesellschaftInventors: Armin Volker Grenacher, Hans Stepp
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Patent number: 6720457Abstract: Olefins having from 5 to 24, in particular from 5 to 12, carbon atoms are hydroformylated by reacting an olefin or a mixture of olefins in the presence of an unmodified cobalt catalyst in a single-stage process in a reactor at a temperature of from 100° C. to 220° C. and a pressure of from 100 bar to 400 bar, to obtain an aldehyde, an alcohol or a mixture thereof. An aqueous bottom phase and an organic phase are present in the reactor, the aqueous bottom phase is mixed with the organic phase, and a concentration of the cobalt catalyst, calculated as metallic cobalt, in the aqueous bottom phase is in the range from 0.4 to 1.7% by mass based on the total weight of the aqueous bottom phase. A level of the aqueous bottom phase in the reactor is kept constant during steady-state operation.Type: GrantFiled: July 24, 2002Date of Patent: April 13, 2004Assignee: Oxeno Olefinchemie GmbHInventors: Stefan Drees, Bernhard Scholz, Alfred Kaizik, Walter Toetsch, Wilfried Bueschken, Martin Trocha
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Publication number: 20040054236Abstract: A process of producing aldehydes in a continuous hydroformylation process of continuously reacting an olefinic unsaturated compound with carbon monoxide and hydrogen in the presence of a rhodium-phosphite based complex catalyst and continuously separating at least one component from a reaction product, the process being characterized in that at least a part of an aldehyde product and water are taken out as a mixed vapor flow from a catalyst-existent region in the process, and at least a part thereof is fed outside the catalyst-existent region as it stands as the vapor or as a condensate after cooling, to reduce the water concentration within the catalyst-existent region, whereby decomposition of phosphite ligands in the hydroformylation process of olefins is suppressed.Type: ApplicationFiled: September 8, 2003Publication date: March 18, 2004Applicant: MITSUBISHI CHEMICAL CORPORATIONInventors: Akio Ueda, Yuuichi Fujita, Hirotaka Kawasaki
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Publication number: 20040024259Abstract: A process for preparing hydroformylation products of olefins having from 2 to 8 carbon atoms comprisesType: ApplicationFiled: December 26, 2002Publication date: February 5, 2004Inventors: Wolfgang Richter, Roland Krokoszinski, Rolf Muller, Bernhard Geissler
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Publication number: 20040015011Abstract: A process for preparing hydroformylation products of propylene and for preparing acrylic acid and/or acrolein comprises a) feeding a propylene-containing feed in which from 2 to 40% by weight of propane is present and also carbon monoxide and hydrogen into a reaction zone and reacting this mixture in the presence of a hydroformylation catalyst to form hydroformylation products of propane, b) separating a stream consisting essentially of unreacted propylene and propane from the output from the reaction zone, and c) subjecting the stream consisting essentially of propylene and propane to a catalytic gas-phase oxidation in the presence of molecular oxygen to form acrylic acid and/or acrolein.Type: ApplicationFiled: December 26, 2002Publication date: January 22, 2004Inventors: Roland Krokoszinski, UIrich Hammon, Kevin Todd
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Patent number: 6680414Abstract: The present invention provides a process, which includes: in a homogeneous liquid phase including water, and over a fixed-bed catalyst, continuously hydrogenating at least one hydroformylation product obtained from a hydroformylation of one or more C4-16 olefins to produce at least one output mixture; wherein the fixed-bed catalyst includes at least one element of transition group eight of the Periodic Table of the Elements; wherein the output mixture includes at least one corresponding alcohol and from 0.05 to 10% by weight of water; and wherein in a steady-state operation of the process, from 3 to 50% more hydrogen is fed to the hydrogenation than is consumed by the hydrogenation.Type: GrantFiled: December 14, 2001Date of Patent: January 20, 2004Assignee: Oxeno Olefinchemie GmbHInventors: Cord Knoop, Bernhard Scholz, Alfred Kaizik, Dietmar Gubisch, Joachim Schuler, Walter Tötsch, Wilfried Büschken
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Patent number: 6677268Abstract: An improved catalyst based on cobalt and/or rhodium dissolved in a non-aqueous ionic solvent which is liquid at a temperature of less than 90° C. More particularly, the catalyst comprises at least one complex of cobalt and/or rhodium co-ordinated with at least one nitrogen-containing ligand and the non-aqueous ionic solvent comprises at least one quaternary ammonium and/or phosphonium cation and at least one inorganic anion.Type: GrantFiled: July 12, 2002Date of Patent: January 13, 2004Assignee: Institut Francais du PetroleInventors: Gerhard Hillebrand, Andre Hirschauer, Dominique Commereuc, Helene Olivier-Bourbigou, Lucien Saussine
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Patent number: 6660892Abstract: This invention is a process for synthesizing aliphatic 1,3-diols in one step by hydroformylation and hydrogenation of oxirane, carbon monoxide, and hydrogen employing a catalyst comprising a cobalt carbonyl compound and a cocatalyst metal compound ligated with a ligand in a ligand to cocatalyst metal atom molar ratio in the range of 0.2:1.0 to 0.6:1.0, optionally in the presence of a promoter, where recovery of product is preferably accomplished via water extraction of a diol rich phase from the bulk reaction mixture. The process modifications can, particularly in combination, be beneficial with respect to product recovery, catalyst recycle, and overall economics of a one-step process for producing aliphatic 1,3-diols.Type: GrantFiled: February 7, 2003Date of Patent: December 9, 2003Assignee: Shell Oil CompanyInventors: Joseph Broun Powell, Paul Richard Weider, John Frederick Knifton, Kevin Dale Allen, Lynn Henry Slaugh, Juan Pedro Arhancet
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Patent number: 6642420Abstract: A process for the preparation of aldehydes and/or alcohols or amines by reacting olefins in the liquid phase with carbon monoxide and hydrogen, a part of these gases being dispersed in the form of gas bubbles in the reaction liquid and another part being dissolved in the reaction liquid, in the presence or absence of a primary or secondary amine and in the presence of a cobalt carbonyl, rhodium carbonyl, palladium carbonyl or ruthenium carbonyl complex dissolved homogeneously in the reaction liquid and having a phosphorus-, arsenic-, antimony- or nitrogen-containing ligand, at elevated temperatures and at 1 to 100 bar, wherein the reaction is carried out in a vertically arranged, tubular reactor comprising a reactor body and at least one circulation line, a part of the reaction liquid is fed continuously via the circulation line to at least one nozzle which is mounted in the upper part of the reactor body and is coordinated with a guide member, open at the top and bottom and bounded by parallel walls, in theType: GrantFiled: February 7, 2001Date of Patent: November 4, 2003Assignee: BASF AktiengesellschaftInventors: Peter Zehner, Armin Ulonska, Rocco Paciello
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Patent number: 6639091Abstract: Bidentate ligand of formula II, R1R2M1—R—M2R3R4 (II) wherein M1 and M2 are independently P, As or Sb; R1, R2, R3 and R4 independently represent tertiary alkyl groups, or R1 and R2 together and/or R3 and R4 together represent an optionally substituted bivalent cycloaliphatic group whereby the two free valencies are linked to M1 or M2, and R represents a bivalent aliphatic bridging group containing from 2 to 6 atoms in the bridge, which is substituted with two or more substituents. A catalyst system comprising: a) a source of group VIII metal cations; b) a source of such a bidentate ligand; and c) a source of anions, and use of such a catalyst system in a process for the carbonylation of optionally substituted ethylenically or acetylenically unsaturated compounds by reaction with carbon monoxide and a coreactant is provided.Type: GrantFiled: May 17, 2001Date of Patent: October 28, 2003Assignee: Shell Oil CompanyInventors: Eit Drent, Michael Rolf Eberhard, Paul Gerard Pringle
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Patent number: 6639114Abstract: 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: GrantFiled: February 13, 2002Date of Patent: October 28, 2003Assignee: BASF AktiengesellschaftInventors: Wolfgang Ahlers, Rocco Paciello, Dieter Vogt, Jarl Ivar van der Vlugt
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Publication number: 20030195378Abstract: In a process for the hydroformylation of ethylenically unsaturated compounds, at least one complex of a metal of transition group VIII. with at least one phosphorus-, arsenic- or antimony-containing compound as ligand is used as hydroformylation catalyst, where the compound used as ligand in each case comprises two groups which comprise a P, As or Sb atom and at least two further hetero atoms and are bound to a xanthene-like molecular framework. New compounds of this type and catalysts which comprise at least one complex of a metal of transition group VIII. with at least one such compound as ligand are also provided.Type: ApplicationFiled: March 11, 2003Publication date: October 16, 2003Inventors: Wolfgang Ahlers, Dag Wiebelhaus, Rocco Paciello, Michael Bartsch, Robert Baumann, Dieter Vogt, Alison Hewat
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Publication number: 20030195368Abstract: The invention relates to the bisphosphites of the general formula(I), wherein R1, R2, R3, $4 R5 R6 represent H, an aliphatic, alicyclic, aliphatic-alicyclic, heterocyclic, aliphatic-heterocyclic, aromatic, aliphatic-aromatic hydrocarbon group with 1 to 50 carbon atoms, F, Cl, Br, I, —OR7, —COR7, —CO2R7, —CO2M, —SR7, —SO2R7, —SOR7, —SO3R7, —SO3M, —SO2NR7R8, NR7R8, N═CR7R8, NH2, wherein R1 to R6 are the same or different and can be covalently linked with each other, R7, R8 represent H, a substituted or unsubstituted, aliphatic or aromatic hydrocarbon group with 1 to 25 carbon atoms, which are the same or different, M represents an alkali metal, alkaline earth metal, ammonium, phosphonium ion; Q represents a bivalent, aliphatic alicyclic, aliphatic-alicyclic, heterocyclic, aromatic, aliphatic-aromatic hydrocarbon group with 1 to 50 carbons atoms, W, X represent aliphatic, alicyclic, aliphatic-alicyclic, heterocyclic, aliphatic-heterocyclic, aromatiType: ApplicationFiled: April 24, 2003Publication date: October 16, 2003Inventors: Dirk Rottger, Renat Kadyrov, Armin Borner, Detlef Selent, Dieter Hess
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Publication number: 20030176743Abstract: Olefins having from 2 to 8 carbon atoms are hydroformylated in a process in which (i) an olefin-containing feed in which a proportion of a saturated hydrocarbon having from 2 to 8 carbon atoms is present and also carbon monoxide and hydrogen are fed into a reaction zone and reacted in the presence of a hydroformylation catalyst, (ii) a stream consisting essentially of unreacted olefin and saturated hydrocarbon is separated off from the output from the reaction zone, (iii) the stream is separated into an olefin-enriched fraction and an olefin-depleted fraction by rectification, and (iv) at least part of the olefin-enriched fraction is recirculated to the reaction zone.Type: ApplicationFiled: December 26, 2002Publication date: September 18, 2003Inventors: Helmut Walz, Willi Schnmann, Rolf Mller, Roland Krokoszinski
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Patent number: 6617474Abstract: 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: a non-aqueous ionic liquid which is at least partly miscible with the reaction products and comprises a salt of general formula Q+A−, in which Q+ represents a quaternary ammonium and/or phosphonium and A− represents an anion; and a catalyst comprising a compound or a complex of a transition metal of groups 8, 9 and 10, optionally co-ordinated with a ligand containing at least one atom of phosphorus, arsenic, antimony or nitrogen, comprises addition to the medium, after the reaction section, of an organic solvent in a manner such as to improve the separation by demixing of the crude reaction products from the said polar phase, which is recycled to the reaction section.Type: GrantFiled: January 24, 2002Date of Patent: September 9, 2003Assignee: Institut Francais du PetroleInventors: Frédéric Favre, Dominique Commereuc, Hélène Olivier-Bourbigou
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Patent number: 6610891Abstract: A method of producing aldehydes in a hydroformylation system wherein an olefinic compound is reacted with hydrogen and carbon monoxide in a hydroformylation reaction in the presence of a catalyst is provided. The hydroformylation system includes a reactor and a downstream catalyst process path. The temperature in the reactor and downstream catalyst process path is less than approximately 100° C., and preferably less than approximately 85° C., and most preferably less than approximately 80° C., such that formation of high boiler components from the reaction are substantially minimized. Further, the method of the present invention reduces degradation or decomposition of the catalyst, and in particular the ligand compound.Type: GrantFiled: December 3, 1999Date of Patent: August 26, 2003Assignee: Mitsubishi Chemical CorporationInventors: Lionel O'Young, Masaki Takai, Tooru Tsukahara, Akio Nakanishi
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Publication number: 20030149267Abstract: Bidentate phosphine ligands of the formula 1Type: ApplicationFiled: November 12, 2002Publication date: August 7, 2003Applicant: Celanese GmbHInventors: Holger Geissler, Petrus W.N.M. Van Leeuwen, Paul C.J. Kamer, Lars A. Van der Veen
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Publication number: 20030144559Abstract: A process for the catalytic hydroformylation of olefins having from 3 to 24 carbon atoms, where the catalyst used comprises a metal of transition group 8 of the Periodic Table in the presence of a ligand represented by formula I: 1Type: ApplicationFiled: November 13, 2002Publication date: July 31, 2003Applicant: Degussa AGInventors: Dieter Hess, Dirk Roettger, Detlef Selent, Armin Boerner
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Publication number: 20030139630Abstract: The present invention relates to a process for the formylation of organic compounds.Type: ApplicationFiled: November 25, 2002Publication date: July 24, 2003Inventors: Hanns Wurziger, Guido Pieper, Norbert Schwesinger
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Publication number: 20030120118Abstract: A process for producing oxygenated products from an olefin-rich feedstock comprise reacting, in a hydroformylation stage, a Fischer-Tropsch derived olefinic product comprising linear and methyl branched olefins, with carbon monoxide and hydrogen in the presence of a catalytically effective quantity of a hydroforhylation catalyst and under hydroformylation reaction conditions, to produce oxygenated products comprising linear and methyl branched aldehydes and/or alcohols. The Fischer-Tropsch derived olefinic product is that obtained by subjecting a synthesis gas comprising carbon monoxide (CO) and hydrogen (H2) to Fischer-Tropsch reaction conditions in the presence of a Fischer-Tropsch catalyst.Type: ApplicationFiled: October 28, 2002Publication date: June 26, 2003Applicant: SASOL TECHNOLOGY (PROPRIETARY) LIMITEDInventors: Mark Justin Betts, Mark Eberhard Dry, Arie Geertsema, Gerhardus Johannes Hendricus Rall
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Patent number: 6583324Abstract: 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: September 18, 2001Date of Patent: June 24, 2003Assignee: Mitsubishi Chemical CorporationInventors: Masaki Takai, Iwao Nakajima, Tooru Tsukahara, Yoshiyuki Tanaka, Hisao Urata, Akio Nakanishi
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Publication number: 20030114714Abstract: The invention relates to a process for the preparation of aldehydes in which at least one compound containing a vinyl or vinylidene group is reacted with carbon monoxide and hydrogen in the presence of a source of a metal from sub-group VIII and in the presence of a bidentate diphosphine ligand, where the diphosphine ligand has the general formula I 1Type: ApplicationFiled: November 7, 2002Publication date: June 19, 2003Inventors: Wolfgang Ahlers, Michael Slany
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Publication number: 20030114718Abstract: The present invention provides a process, which includes:Type: ApplicationFiled: December 14, 2001Publication date: June 19, 2003Applicant: OXENO OLEFINCHEMIE GMBHInventors: Cord Knoop, Bernhard Scholz, Alfred Kaizik, Dietmar Gubisch, Joachim Schuler, Walter Totsch, Wilfried Buschken
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Patent number: 6579997Abstract: A metallacrown ether ligand chelates a transition metal atom to form a catalyst well suited to perform hydroformylation in the presence of carbon monoxide, hydrogen and an unsaturated substrate compound.Type: GrantFiled: July 3, 2002Date of Patent: June 17, 2003Assignee: UAB Research FoundationInventors: Gary M. Gray, Maheswaran Harihara Sarma, Dale C. Smith
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Patent number: 6566558Abstract: In a process for the hydroformylation of alkanes, alkenes or trialkylboranes under supercritical or near-critical conditions, hydroformylation is effected using a heterogeneous catalyst in a continuous flow reactor containing a supercritical or near-critical reaction medium. Selectivity of product formation may be achieved by independently varying one of more of the temperature, pressure, catalyst, mole ratios of hydrogen and carbon monoxide and flow rate.Type: GrantFiled: March 12, 2001Date of Patent: May 20, 2003Assignee: Thomas Swan & Co., LimitedInventors: Martyn Poliakoff, Nicola J. Meehan, Stephen K. Ross, Stefan Wieland, Stefan Roeder
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Patent number: 6559344Abstract: 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: GrantFiled: February 19, 2002Date of Patent: May 6, 2003Assignee: BASF AktiengesellschaftInventor: Thomas Mackewitz
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Publication number: 20030083528Abstract: The present invention relates to a process for preparing aldehydes by reaction of olefinically unsaturated compounds with carbon monoxide and hydrogen, wherein, during the process, rhodium is added in the form of a reaction product from the reaction of metallic rhodium and/or more than one rhodium compound with rhodium-complexing compounds and with carbon monoxide and hydrogen, the use of said reaction product in catalytic processes and also the preparation of a catalytic composition with addition of said reaction product.Type: ApplicationFiled: July 3, 2002Publication date: May 1, 2003Inventors: Hans Bohnen, Carl Dieter Frohning, Ernst Wiebus
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Patent number: 6555716Abstract: 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: GrantFiled: November 30, 2000Date of Patent: April 29, 2003Assignee: Oxeno Olefinchemie GmbHInventors: Guido Protzmann, Klaus-Diether Wiese, Wilfried Büschken, Dirk Röttger
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Publication number: 20030055293Abstract: The present invention relates to a process for the epoxidation of olefins.Type: ApplicationFiled: October 28, 2002Publication date: March 20, 2003Inventors: Hanns Wurziger, Guido Pieper, Norbert Schwesinger
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Publication number: 20030032843Abstract: Olefins having from 5 to 24, in particular from 5 to 12, carbon atoms are hydroformylated by reacting an olefin or a mixture of olefins in the presence of an unmodified cobalt catalyst in a single-stage process in a reactor at a temperature of from 100° C. to 220° C. and a pressure of from 100 bar to 400 bar, to obtain an aldehyde, an alcohol or a mixture thereof. An aqueous bottom phase and an organic phase are present in the reactor, the aqueous bottom phase is mixed with the organic phase, and a concentration of the cobalt catalyst, calculated as metallic cobalt, in the aqueous bottom phase is in the range from 0.4 to 1.7% by mass based on the total weight of the aqueous bottom phase. A level of the aqueous bottom phase in the reactor is kept constant during steady-state operation.Type: ApplicationFiled: July 24, 2002Publication date: February 13, 2003Applicant: OXENO OLEFINCHEMIE GMBHInventors: Stefan Drees, Bernhard Scholz, Alfred Kaizik, Walter Toetsch, Wilfried Bueschken, Martin Trocha
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Patent number: 6509505Abstract: Phosphabenzene compounds of the formula (I) where the radicals R1 to R13 are, independently of one another, hydrogen, COOM, SO3M, NR3X, NR2, OR, COOR or SR (where M=hydrogen, NH4 or alkali metal, X=anion, R=hydrogen or C1-C6-alkyl), or C1-C12-alkyl, C6-C12-aryl, C7-C12-aralkyl, C7-C12-alkaryl or C3-C6-heteroaromatics, where the alkyl, aryl, alkaryl and aralkyl radicals may bear the abovementioned radicals as substituents and two or more of the radicals may be joined to form aliphatic or fused-on rings, where at least one of the radicals R4 and R8 and at least one of the radicals R9 and R13 is not hydrogen, can be used for preparing hydroformylation catalysts.Type: GrantFiled: September 11, 2001Date of Patent: January 21, 2003Assignee: BASF AktiengesellschaftInventors: Rocco Paciello, Thomas Mackewitz, Michael Röper, Bernhard Breit
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Patent number: 6500991Abstract: Aldehydes are prepared by a process, which comprises: hydroformylating olefins having 3 to 21 carbon atoms under an atmosphere of CO/H2 in the presence of a rhodium catalyst in a hydroformylation reactor; and upon discharging the reaction product from the reactor, a) separating the discharged material into a gaseous phase and a liquid phase, b) separating the liquid phase into a top fraction containing unconverted olefins and aldehydes and a bottoms fraction containing the rhodium catalyst, and c) cooling the bottoms fraction below the temperature of the material discharged from the hydroformylation reactor and feeding a gas containing carbon monoxide into the bottoms fraction.Type: GrantFiled: September 25, 2001Date of Patent: December 31, 2002Assignee: Oxeno Olefinchemie GmbHInventors: Klaus-Diether Wiese, Martin Trocha, Dirk Röettger, Walter Töetsch, Alfred Kaizik, Wilfried Büschken
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Publication number: 20020188160Abstract: A process is provided for catalyzing an organic reaction to form a reaction product by placing reactants and a catalyst for the organic reaction, the catalyst of a metal complex and at least one ligand soluble within one of the phases of said aqueous biphasic system, within an aqueous biphasic system including a water phase, a dense phase fluid, and a surfactant adapted for forming an emulsion or microemulsion within the aqueous biphasic system, the reactants soluble within one of the phases of the aqueous biphasic system and convertible in the presence of the catalyst to a product having low solubility in the phase in which the catalyst is soluble; and, maintaining the aqueous biphasic system under pressures, at temperatures, and for a period of time sufficient for the organic reaction to occur and form the reaction product and to maintain sufficient density on the dense phase fluid, the reaction product characterized as having low solubility in the phase in which the catalyst is soluble.Type: ApplicationFiled: November 18, 1999Publication date: December 12, 2002Inventors: GUNILLA B. JACOBSON, WILLIAM TUMAS, KEITH P. JOHNSTON
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Patent number: 6492525Abstract: The invention concerns novel organometallic complexes comprising cationic heterocyclic carbenes. It also concerns a method for preparing said complexes from dicationic heterocyclic precursor compounds. It further concerns the use as catalysts of said organometallic complexes for a certain number of chemical reactions.Type: GrantFiled: June 21, 2001Date of Patent: December 10, 2002Assignee: Rhodia Fiber & Resin IntermediatesInventors: Guy Bertrand, Lutz Stelzig, Olivier Guerret, Christophe Buron, Heinz Gornitzka, Paolo Burattin
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Patent number: 6492564Abstract: The invention relates to a catalytic process for carrying out multiphase reactions in a tubular reactor, with the catalyst being present in the continuous phase and at least one starting material in a disperse phase and the loading factor B of the tubular reactor being equal to or greater than 0.8. The process is especially suitable in particular for the hydroformylation of olefins. The aldehydes thus prepared can ideally be used for the preparation of alcohols, carboxylic acids or in aldol condensations.Type: GrantFiled: June 2, 2000Date of Patent: December 10, 2002Assignee: OXENO Olefinchemie GmbHInventors: Klaus-Diether Wiese, Guido Protzmann, Juergen Koch, Dirk Roettger, Martin Trocha
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Patent number: 6482992Abstract: Olefins are hydroformylated to give alcohols and/or aldehydes in a plurality of hydroformylation stages, each of which comprises: a) hydroformylating olefins having a carbon atom content of 6 to 24 carbon atoms in the presence of a cobalt- or rhodium catalyst in a reactor to the point of conversion of olefin reactant to product of 20 to 98%; b) removing the catalyst from the resulting liquid discharged from the reactor; c) separating the resulting liquid hydroformylation mixture into a low-boiler fraction comprising olefins and paraffins, and a bottoms fraction comprising aldehydes and/or alcohols; and d) reacting the olefins present in the low-boiler fraction in subsequent process stages comprising steps a, b and c and combining the bottoms fractions of process steps c) of all process stages.Type: GrantFiled: July 16, 2001Date of Patent: November 19, 2002Assignee: OXENO Olefinchemie GmbHInventors: Bernhard Scholz, Franz Nierlich, Alfred Kaizik, Dieter Hess, Wilfried Bueschken, Klaus-Diether Wiese, Dirk Roettger, Guido Protzmann
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Patent number: 6479708Abstract: A process is provided for catalyzing an organic reaction to form a reaction product by placing reactants and a catalyst for the organic reaction, the catalyst of a metal complex and at least one ligand soluble within one of the phases of said aqueous biphasic system, within an aqueous biphasic system including a water phase, a dense phase fluid, and a surfactant adapted for forming an emulsion or microemulsion within the aqueous biphasic system, the reactants soluble within one of the phases of the aqueous biphasic system and convertible in the presence of the catalyst to a product having low solubility in the phase in which the catalyst is soluble; and, maintaining the aqueous biphasic system under pressures, at temperatures, and for a period of time sufficient for the organic reaction to occur and form the reaction product and to maintain sufficient density on the dense phase fluid, the reaction product characterized as having low solubility in the phase in which the catalyst is soluble.Type: GrantFiled: November 18, 1999Date of Patent: November 12, 2002Assignee: The Regents of the University of CaliforniaInventors: Gunilla B. Jacobson, William Tumas, Keith P. Johnston
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Publication number: 20020161266Abstract: The present invention is drawn to a method of performing a one-pot organic reactions including carbon monoxide as reactant, without the use of an external CO gas source, wherein a reaction mixture containing a solid or liquid CO releasing compound, a non-metal substrate and a metal catalyst is exposed to an energy source to release carbon monoxide from the CO releasing compound and wherein carbon atoms of the released carbon monoxide form a bond with the non-metal substrate compound. The present invention is further drawn to a method of preparing chemical libraries and a kit for organic reactions.Type: ApplicationFiled: December 14, 2001Publication date: October 31, 2002Inventors: Mats Larhed, Mathias Alterman, Yiqian Wan, Anders Hallberg, Nils-Fredrik Kaiser
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Publication number: 20020161251Abstract: 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: April 23, 2002Publication date: October 31, 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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Patent number: 6472565Abstract: The invention relates to a method for producing aldehydes by reacting monoolefins, conjugated and non-conjugated polyolefins, cycloolefins, or derivatives of these classes of compounds with carbon monoxide and hydrogen (hydroformylation) in the presence of rhodium or rhodium compounds and a non-aqueous liquid of the formula (Q30 )aAa−, wherein Q+represents a singly charge ammonium cation that is optionally substituted with organic radicals, and Aa−represents the anion of a sulphonated or carboxylated triester of phosphoric acid.Type: GrantFiled: October 23, 2001Date of Patent: October 29, 2002Assignee: Celanese Chemicals Europe GmbHInventors: Helmut Bahrmann, Hans Bohen
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Patent number: 6469216Abstract: In an improved process for hydroformylation of olefinically unsaturated compounds using a catalyst based on cobalt and/or rhodium employed in a two-phase medium, a catalyst based on cobalt and/or rhodium is used dissolved in a non-aqueous ionic solvent which is liquid at a temperature of less than 90° C., in which the aldehydes formed are slightly soluble or insoluble. More particularly, the catalyst comprises at least one complex of cobalt and/or rhodium co-ordinated with at least one nitrogen-containing ligand and the non-aqueous ionic solvent comprises at least one quaternary ammonium and/or phosphonium cation and at least one inorganic anion. At the end of the reaction, the organic phase is generally separated and the ionic non-aqueous solvent phase containing the catalyst can be re-used.Type: GrantFiled: December 7, 2000Date of Patent: October 22, 2002Assignee: Institut Francais du PetroleInventors: Gerhard Hillebrand, André Hirschauer, Dominique Commereuc, Hélène Olivier-Bourbigou, Lucien Saussine
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Patent number: 6455743Abstract: A process for producing alcohols, which comprises subjecting a mixture comprising an aldehyde having from 2 to 5 carbon atoms and a polycondensate of the aldehyde at a weight ratio of from 95:5 to 5:95 to a mixing hydrogenation reaction in the presence of a catalyst to produce alcohols corresponding to the aldehydes at the same time wherein substantially no by-product is produced.Type: GrantFiled: November 26, 1999Date of Patent: September 24, 2002Assignee: Mitsubishi Chemical CorporationInventors: Akio Ueda, Yuichi Fujita, Atsuhiro Adachi, Hiroki Emoto