Hydroformylation By Reacting Ethylenically Unsaturated Compound, Carbon Monoxide, And Gaseous Hydrogen Patents (Class 568/451)
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Patent number: 7501548Abstract: The invention relates to the use of isobutene-containing olefin feedstock in oligomerization reactions, particularly in the production of octenes as feedstock for the manufacture of plasticizer alcohols, the process comprising contacting a feed comprising isobutene with a molecular sieve at a temperature in excess of 240° C. to produce a product low in triple-branched octenes.Type: GrantFiled: March 10, 2006Date of Patent: March 10, 2009Assignee: ExxonMobil Chemical Patents Inc.Inventors: Stephen Harold Brown, Georges Marie Mathys
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Publication number: 20090054696Abstract: This invention relates to a process for the production of alcohols and/or aldehydes. A hydrocarbon feed stream containing paraffins and olefins, typically in which more than 5% by volume of olefin molecules in the hydrocarbon feed stream have a total number of carbon atoms which is different from the total number of carbon atoms of the most abundant two (preferably three) carbon numbers of olefins (by carbon number) in the hydrocarbon stream, is subjected to a hydroformylation reaction in which olefins are converted to alcohols and/or aldehydes. Paraffins in the hydroformylation product are then separated from alcohols and/or aldehydes by azeotropic distillation in an azeotropic distillation column. The invention also relates to a method for separating alcohols/aldehydes from paraffins in a hydrocarbon feed stream in an azeotropic distillation column using a mid-boiling polar entrainer.Type: ApplicationFiled: August 31, 2006Publication date: February 26, 2009Inventor: James Christoffel Crause
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Patent number: 7495133Abstract: (EN) The invention relates to the use of novel organophosphoric compounds and metal complexes thereof in catalytic reactions, and to the hydroformylation of olefins in the presence of these compounds.Type: GrantFiled: January 27, 2005Date of Patent: February 24, 2009Assignee: Oxeno Olefinchemie GmbHInventors: Cornelia Borgmann, Detlef Selent, Armin Boerner, Klaus-Diether Wiese, Dagmara Ortmann, Oliver Moeller, Dieter Hess
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Publication number: 20090048411Abstract: A method for producing a mixture of ethylene and carbon monoxide by contacting ethane and an oxygen source at a temperature of at least 500° C. to produce ethylene and carbon monoxide. A method for producing an alkyl propionate by steps of: (a) contacting ethane and an oxygen source at a temperature of at least 500° C. to produce ethylene; (b) contacting an alcohol, ethylene and carbon monoxide with an ethylene carbonylation catalyst to produce the alkyl propionate; and (c) separating the alkyl propionate from byproducts and starting materials. The method further comprises condensing the alkyl propionate with formaldehyde to produce an alkyl methacrylate.Type: ApplicationFiled: August 5, 2008Publication date: February 19, 2009Inventors: Abraham Benderly, Scott Han, Mark Anthony Silvano, Donald Lee Zolotorofe
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Patent number: 7485759Abstract: A process for the minimization of phosphonium ion ligand degradation products formed during reaction of a polyunsaturated olefin or an unconjugated functionalized olefin in the presence of a transition metal-triorganophosphine ligand complex catalyst to form as a product, by-product, or intermediate product a conjugated functionalized olefin having a carbon-carbon double bond conjugated to an ?-electron-withdrawing group, such as, an ?,?-unsaturated aldehyde, ketone, ester, acid, or nitrile. The minimization process involves conducting the reaction under selected conditions of conversion, temperature, pressure, or a combination thereof; and/or by selecting a triorganophosphine ligand with a specified steric and/or electronic property.Type: GrantFiled: January 24, 2008Date of Patent: February 3, 2009Assignee: Dow Technology Investments LLCInventors: John R. Briggs, Wei-Jun Peng, Brian M. Roesch, Anthony G. Abatjoglou, Donald L. Morrison
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Patent number: 7446231Abstract: An improved hydroformylation process involving reacting one or more reactants, such as an olefin, with carbon monoxide and hydrogen in the presence of a hydroformylation catalyst, to produce a reaction product fluid comprising one or more products, preferably aldehydes; wherein said process is conducted in a region of the hydroformylation rate curve that is negative or inverse order in carbon monoxide, which is sufficient to prevent and/or lessen deactivation of the hydroformylation catalyst; and wherein total pressure is controlled at a predetermined target value and/or vent flow rate is controlled at a predetermined target value, by adjusting a flow of a carbon-monoxide containing inlet gas, so as to prevent and/or lessen cycling of process parameters, e.g., reaction rate, total pressure, vent flow rate, and/or temperature.Type: GrantFiled: July 19, 2005Date of Patent: November 4, 2008Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Ronald R Peterson, Thomas C. Eisenschmid, David R. Bryant, Morteza Mokhtarzadeh
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Patent number: 7442842Abstract: The present invention relates to a process for asymmetric synthesis in the presence of a chiral catalyst comprising at least one complex of a metal of transition group VIII with ligands capable of dimerization via noncovalent bonds, such catalysts and their use.Type: GrantFiled: November 24, 2004Date of Patent: October 28, 2008Assignee: BASF SEInventors: Christoph Jäkel, Martin Volland, Thomas Mackewitz, Rocco Paciello, Bernhard Breit, Wolfgang Seiche, Martine Weis, Christoph Waloch
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Patent number: 7420092Abstract: A process by which a hydroformylation reaction can be efficiently conducted without lowering the yield of an aldehyde in the reaction is provided. A process for producing an aldehyde which includes subjecting an olefin to a hydroformylation reaction with carbon monoxide and hydrogen in the presence of a catalyst, characterized in that the olefin is fed as a gas to a reactor. In feeding the olefin as a gas to the reactor, it is preferred to gasify the olefin with the heat of the hydroformylation reaction.Type: GrantFiled: November 7, 2005Date of Patent: September 2, 2008Assignee: Mitsubishi Chemical CorporationInventors: Yuichi Fujita, Fumitaka Utsumi
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Patent number: 7405329Abstract: The gas cycle in a high pressure hydroformylation reaction using a series of at least two reactors is controlled to optimise yield, conversion and selectivity and to control reaction temperature. The control is achieved through balancing fresh gases and recycle gases in each of the reactors and as an optional feature the use of hydrogen off gases from the downstream hydrogenation used in the conversion of the hydroformylation reaction product to product alcohols.Type: GrantFiled: December 16, 2004Date of Patent: July 29, 2008Assignee: ExxonMobil Chemical Patents Inc.Inventors: Stephen Wayne Beadle, Ronald Dean Garton, Hubertus Joseph Beckers, Raphael Frans Caers, Arie Van Vliet, John J. Houben
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Patent number: 7365234Abstract: An improved hydroformylation process is provided, which comprises reacting an olefin with CO and H2 in the presence of a hydroformylation catalyst in a liquid that has been volumetrically expanded with a compressed gas, such as supercritical carbon dioxide.Type: GrantFiled: March 16, 2007Date of Patent: April 29, 2008Assignee: University of KansasInventors: Bala Subramaniam, Jon A. Tunge, Hong Jin, Anindya Ghosh
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Patent number: 7351868Abstract: A process for the minimization of phosphonium ion ligand degradation products formed during reaction of a polyunsaturated olefin or an unconjugated functionalized olefin in the presence of a transition metal-triorganophosphine ligand complex catalyst to form as a product, by-product, or intermediate product a conjugated functionalized olefin having a carbon-carbon double bond conjugated to an a-electronwithdrawing group, such as, an a,?-unsaturated aldehyde, ketone, ester, acid, or nitrile. The minimization process involves conducting the reaction under selected conditions of conversion, temperature, pressure, or a combination thereof; and/or by selecting a triorganophosphine ligand with a specified steric and/or electronic property.Type: GrantFiled: June 28, 2004Date of Patent: April 1, 2008Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: John R. Briggs, Wei-Jun Peng, Brian M. Roesch, Anthony G. Abatjoglou, Donald L. Morrison
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Patent number: 7329783Abstract: A hydroformylation process comprising reacting a feedstock composition comprising a compound having at least one olefinic carbon-to-carbon bond with hydrogen and carbon monoxide in the presence of an organophosphine modified cobalt hydroformylation catalyst, wherein the hydroformylation process is carried out in at least two reaction zones, wherein the at least two reaction zones comprise an earlier reaction zone and a later reaction zone, wherein the temperature of the later reaction zone is at least about 2° C. greater than the temperature in the earlier reaction zone, and the temperature of the later reaction zone is in the range of from about 140° C. to about 220° C., and the temperature of the earlier reaction zone is at least about 130° C.Type: GrantFiled: June 28, 2006Date of Patent: February 12, 2008Assignee: Shell Oil CompanyInventor: Wilhelmus Petrus Mul
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Patent number: 7317130Abstract: The present invention relates to a process for preparing aldehydes by hydroformylation of olefinically unsaturated compounds catalyzed by metals of groups 8 to 10 of the Periodic Table of the Elements in the presence of cyclic carbonic esters and ligands which contain no sulfonic acid or sulfonate group.Type: GrantFiled: August 7, 2003Date of Patent: January 8, 2008Assignee: OXENO Olefinchemie GmbHInventors: Oliver Möller, Dirk Fridag, Cornelia Borgmann, Dieter Hess, Klaus-Diether Wiese
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Patent number: 7294729Abstract: A novel bis-chelating composition characterized by formula I: wherein M is a Group VB element; R1 and R2 are each independently selected from hydrogen and monovalent hydrocarbyl radicals; or R1 and R2 are bonded together to form a diradical; or one of R1 or R2 is hydrogen or a monovalent hydrocarbyl radical, while the other of R1 or R2 is a hydrocarbyl radical bonded to an atom in Ar; wherein Ar is selected from 1,2-arylenes; Q is selected from 1,2-arylenes, 2,2?-bisarylenes and alkyl diradicals; and W is selected from II, III, IV, or V: wherein M is as defined hereinbefore; each R is independently selected from hydrogen and monovalent hydrocarbyl radicals; X is selected from alkyl and aryl diradicals; Ar1 and Ar2 are each independently selected from 1,2-arylenes;Ar3 and Ar4 are each independently selected from monovalent aryl radicals; and n in formula IV is 0 or 1.Type: GrantFiled: September 26, 2003Date of Patent: November 13, 2007Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Wei-Jun Peng, Johnathan E Holladay
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Publication number: 20070219399Abstract: An improved hydroformylation process is provided, which comprises reacting an olefin with CO and H2 in the presence of a hydroformylation catalyst in a liquid that has been volumetrically expanded with a compressed gas, such as supercritical carbon dioxide.Type: ApplicationFiled: March 16, 2007Publication date: September 20, 2007Applicant: University of KansasInventors: Bala Subramaniam, Jon A. Tunge, Hong Jin, Anindya Ghosh
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Patent number: 7270985Abstract: A process is disclosed to treat the protein hydrolysate, prepared conventionally from a proteinous source, with alkali metal hydride to obtain alcohol which is subsequently oxidized to obtain aldehyde under certain specified conditions, thereby converting large protein molecules into aldehyde based industrial products of much smaller molecular size.Type: GrantFiled: September 14, 2004Date of Patent: September 18, 2007Assignee: Council of Scientific & Industrial ResearchInventors: James Kanagaraj, Gopala Suseela Rajakumar, Sayeed Sadulla
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Patent number: 7259279Abstract: Process for the hydroformylation of olefins by linkage of the input parameters prevailing in the hydroformylation reaction to the target parameters of a hydroformylation reaction, wherein the linkage is achieved by means of at least one synthetic neuronal network.Type: GrantFiled: November 15, 2005Date of Patent: August 21, 2007Assignee: Oxea GmbHInventors: Dietmar Thiel, Carl Dieter Frohning
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Patent number: 7232931Abstract: Process for preparing aldehydes and alcohols by rhodium-catalyzed hydroformylation of olefins having 6–20 carbon atoms with subsequent separation by distillation of the output from the hydroformylation reaction into the hydroformylation products and a rhodium-containing solution and recirculation of this solution to the hydroformylation reaction, wherein the rhodium concentration of the recirculated rhodium-containing solution is 20–150 ppm by mass.Type: GrantFiled: December 5, 2002Date of Patent: June 19, 2007Assignee: OXENO Olefinchemie GmbHInventors: Walter Toetsch, Alfred Kaizik, Hermann-Josef Schulte-Althoff
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Patent number: 7227045Abstract: Process for the preparation of a mixture comprising C5+ linear olefins, which process comprises the steps of (a) reacting carbon monoxide and hydrogen in the presence of an effective amount of Fischer-Tropsch catalyst under Fischer-Tropsch reaction conditions; (b) separating from the hydrocarbon mixture thus prepared at least one hydrocarbon fraction, of which at least 95% by weight consists of hydrocarbons containing 15 carbon atoms or more; (c) contacting this hydrocarbon fraction with hydrogen in the presence of an effective amount of hydrogenation catalyst under hydrogenation conditions; (d) subjecting the hydrogenated hydrocarbon fraction thus obtained to a mild thermal cracking treatment; and (e) separating from the cracked product thus prepared the mixture comprising C5+ linear olefins.Type: GrantFiled: May 10, 2004Date of Patent: June 5, 2007Assignee: Shell Oil CompanyInventors: Joachim Ansorge, Hendrik Dirkzwager, Joannes Ignatius Geijsel, Abdul Razak Mohamad Ali, Timothy Michael Nisbet, Laurent Alain Michel Fenouil
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Patent number: 7223374Abstract: A process for hydroformylating olefinically unsaturated compounds by means of a cobalt-based catalyst is carried out in a non-aqueous ionic liquid which is a liquid at a temperature below 90° C. and comprises at least one ammonium and/or phosphonium and/or sulfonium cation Q+ and at least one anion A?; catalyst recycling is improved by using a ligand selected from the group consisting of Lewis bases and employing a depressurization step between the pressurized reaction step and the step for separating the phases by decanting. At the end of said depressurization step, the organic phase is separated in the decanting step and the non-aqueous ionic liquid containing the catalyst can be re-used.Type: GrantFiled: February 10, 2006Date of Patent: May 29, 2007Assignee: Institut Francais du PetroleInventors: Lionel Magna, Hélène Olivier-Bourbigou, Lucien Saussine, Virginie Kruger-Tissot
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Patent number: 7217848Abstract: This invention comprises a process for hydrogenation of aldehydes to alcohols using novel homogeneous catalysts. The catalysts are generated in situ under hydrogen and carbon monoxide gases in a suitable solvent, by mixing a rhodium catalyst precursor, such as Rh(CO)2 acetoacetonate and a defined ligand.Type: GrantFiled: November 29, 2004Date of Patent: May 15, 2007Assignee: Dow Global Technologies Inc.Inventor: Wei-Jun Peng
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Patent number: 7208635Abstract: The invention relates to a hydroformylation process in which at least one olefin having from 2 to 6 carbon atoms is reacted continuously with carbon monoxide and hydrogen in the presence of a hydroformylation catalyst in a reaction zone in which a liquid phase is present and a stream S) is taken from the liquid phase, heat is removed from this stream and the stream is subsequently returned to the reaction zone without removal of a material component.Type: GrantFiled: January 16, 2003Date of Patent: April 24, 2007Assignee: BASF AktiengesellschaftInventors: Wolfgang Richter, Rolf Müller, Roland Krokoszinski
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Patent number: 7196230Abstract: A novel organophosphorus composition and synthesis thereof, the composition being characterized by one phosphite moiety, one phosoxophite moiety, and a plurality of sterically bulky substituents. The novel composition finds utility as a ligand in Group VIII transition metal phosoxophite complex catalysts and complex catalyst precursors that are used in carbonylation processes, preferably, hydroformylation processes. Additionally, there is disclosed a novel method of preparing a phosphoromonochloridite composition that finds utility as a precursor to the novel phosoxophite composition.Type: GrantFiled: March 4, 2003Date of Patent: March 27, 2007Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Wei-Jun Peng, David Robert Bryant
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Patent number: 7193116Abstract: The present invention relates to a process for preparing aldehydes by hydroformylation catalyzed by metals of groups 8 to 10 of the Periodic Table of the Elements in the presence of cyclic carbonic esters.Type: GrantFiled: August 7, 2003Date of Patent: March 20, 2007Assignee: OXENO Olefinchemie GmbHInventors: Oliver Moeller, Klaus-Diether Wiese, Dieter Hess, Cornelia Borgmann, Alfred Kaizik, Dirk Fridag
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Patent number: 7179947Abstract: A process for the catalytic hydroformylation of olefins having from 6 to 24 carbon atoms, in which the hydroformylation is carried out in one or more stage(s) and a mixture comprising at least one olefin and an aldehyde in a molar ratio of aldehyde to olefin of from 0.005:1 to 0.2:1 is used as feed in at least one of these stages which is carried out in the presence of an unmodified cobalt complex as catalyst.Type: GrantFiled: December 2, 2005Date of Patent: February 20, 2007Assignee: Oxeno Olefinchemie GmbHInventors: Hans-Gerd Lueken, Alfred Kaizik, Stefan Drees, Wilfried Bueschken, Wilhelm Droste
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Patent number: 7173138Abstract: Pnicogen chelate compounds which have two pnicogen-containing groups joined to one another via a xanthene-like or triptycene-like molecular skeleton and in which at least one pyrrole group is covalently bound via its nitrogen atom to each pnicogen atom form complexes with metals of transition group VIII which are useful as catalysts for the hydroformylation of olefins.Type: GrantFiled: March 28, 2002Date of Patent: February 6, 2007Assignee: BASF AktiengesellschaftInventors: Wolfgang Ahlers, Rocco Paciello, Dieter Vogt, Peter Hofmann
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Patent number: 7169950Abstract: The invention relates to a method for producing monocarbonyl compounds or biscarbonyl compounds or hydroxyl compounds by ozonizing, unsaturated organic carbon compounds that, per molecule, have one or more olefinic or aromatic double bonds, which can be cleaved by ozone, and by subsequently processing the ozonization products.Type: GrantFiled: February 13, 2002Date of Patent: January 30, 2007Assignee: DSM Fine Chemicals Austria NFG GmbH & Co KGInventors: Alexander Sajtos, Engelbert Kloimstein, Curt Zimmermann
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Patent number: 7145042Abstract: The invention relates to a method for producing dialdehydes and/or ethylenically unsaturated monoaldehydes by reacting at least one compound with at least two ethylenically unsaturated double bonds with carbon monoxide and hydrogen in the presence of a hydroformylating catalyst with at least one complex of a metal of subgroup VIII. The subgroup comprises at least pnicogen chelate ligands.Type: GrantFiled: September 12, 2003Date of Patent: December 5, 2006Assignee: BASF AktiengesellschaftInventors: Martin Volland, Wolfgang Ahlers, Klaus Ebel, Rocco Paciello, Michael Röper, Thomas Mackewitz, Volker Böhm, Xavier Sava, Oliver Löber, Oliver Bey, Jürgen Stephan, Frank Haese
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Patent number: 7115387Abstract: A process is disclosed to treat the protein hydrolysate, prepared conventionally from a proteinous source, with alkyl halide to obtain alcohol which is subsequently oxidized to obtain aldehyde under certain specified conditions, thereby converting large protein molecules into aldehyde based industrial products of much smaller molecular size.Type: GrantFiled: September 15, 2003Date of Patent: October 3, 2006Assignee: Council of Scientific & Industrial ResearchInventors: James Kanagaraj, Gopala Suseela Rajakumar, Sayeed Sadulla
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Patent number: 7102034Abstract: A process for preparing sulfonated arylphosphines by reaction of arylphosphines with oleum, wherein, after reaction of the arylphosphines with oleum, the sulfonation mixture is firstly diluted with water, an inert gas stream is then passed through the diluted sulfonation mixture until SO2 is no longer liberated from the diluted sulfonation mixture and the latter is then worked up further in a customary manner and its use.Type: GrantFiled: December 8, 2004Date of Patent: September 5, 2006Assignee: Celanese Chemicals Europe GmbHInventors: Michael Riedel, Ernst Wiebus, Carl D Frohning, Wilfried Fenske, Florian Rampf, Jurgen Herwig, Helmut Bahrmann, Klaus Bergrath, Wolfgang Zgorzel-Ski, Robert Eckl, Hans Bohnen, Richard Fischer, Kurt Schalapski, Wolfgang Greb
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Patent number: 7102033Abstract: A continuous hydroformylation process for producing an aldehyde comprising 1) reacting an olefinically unsaturated compound, carbon monoxide and hydrogen in the presence of a rhodium-organobisphosphite complex catalyst at a partial pressure of carbon monoxide and hydrogen, and 2) exposing a mixture comprising at least a portion of the catalyst of 1) to a gaseous mixture comprising hydrogen at a pressure that is greater than the partial pressure of carbon monoxide and hydrogen during the reaction.Type: GrantFiled: April 11, 2002Date of Patent: September 5, 2006Assignee: DSM IP Assets B.V.Inventors: Otto Erik Sielcken, Hubertus Adrianus Smits, Imre Toth
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Patent number: 7087797Abstract: A continuous hydroformylation process for forming an aldehyde comprising 1) reacting an olefinically unsaturated compound containing from 2 to 30 carbon atoms with carbon monoxide and hydrogen in the presence of a rhodium-bisphosphite ligand complex catalyst and 2) distilling a mixture comprising at least a part of the catalyst of 1), wherein the distilling is performed in the substantial absence of molecular hydrogen.Type: GrantFiled: April 11, 2002Date of Patent: August 8, 2006Assignee: DSM IP Assets B.V.Inventors: Otto Erik Sielcken, Hubertus Adrianus Smits, Imre Toth
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Patent number: 7081553Abstract: The Cobalt Flash Process is modified by replacing formic acid with acetic acid as process acid. Efficiency using acetic acid as process acid is achieved by two improvements which may be added separately and independently: (1) separation of acetic acid and water from the condensate distilled off in the cobalt salt concentration stage; and (2) removal of formic acid from the system by reaction with the product alcohol in the preformer.Type: GrantFiled: March 28, 2003Date of Patent: July 25, 2006Assignee: ExxonMobil Chemical Patents Inc.Inventors: Dominic T. Clausi, Eddy T. van Driessche, Ronald D. Garton, James T. Ritchie, Nico A. de Munck
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Patent number: 7081554Abstract: The Oxo Process that recycles its cobalt primarily as cobalt salt is improved by concentration of the cobalt salt solution from the demetalling section and the addition of a separation step for organic acid and water. This allows for a higher reuse of acid in the process and thus a lower amount of acid in the waste water. Injecting a higher concentration of cobalt salt solution to the reaction section also reduces the requirement for cobalt source.Type: GrantFiled: March 28, 2003Date of Patent: July 25, 2006Assignee: ExxonMobil Chemical Patent Inc.Inventors: Ronald D. Garton, James T. Ritchie, Raphael Frans Caers
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Patent number: 7074955Abstract: A continuously operated heterogeneously catalyzed gas-phase partial oxidation of at least one organic compound in an oxidation reactor is operated safely by a process in which an explosion diagram for the feed gas mixture is deposited as the basis of a cut-out mechanism in a computer.Type: GrantFiled: June 12, 2003Date of Patent: July 11, 2006Assignee: BASF AktiengesellschaftInventors: Ulrich Hammon, Jochen Meschke, Ulrich Rauh, Klaus Joachim Müller-Engel, Peter Schlemmer, Volker Schliephake
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Patent number: 7015361Abstract: Olefins having at least 6 carbon atoms are hydroformylated in the presence of a homogeneous catalyst in a continuous process in which a) a vertical tall cylindrical reactor (1) whose interior space is divided by means of internals (2) into at least two reaction chambers which extend essentially in the longitudinal direction of the reactor is used, b) at least one olefin is introduced into the reactor together with synthesis gas at the lower end of the first reaction chamber, c) a partially reacted reaction mixture is conveyed from the upper end of a reaction chamber to the lower end of a next reaction chamber; and d) the hydroformylated olefin is taken off at the upper end of the last reaction chamber. The process allows a high conversion at a given reactor volume.Type: GrantFiled: February 13, 2002Date of Patent: March 21, 2006Assignee: BASF AktiengesellschaftInventors: Peter Zehner, Michael Nilles
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Patent number: 7002044Abstract: 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: GrantFiled: August 15, 2003Date of Patent: February 21, 2006Assignee: The University of ConnecticutInventors: Can Erkey, Xing Dong
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Patent number: 6995293Abstract: The present invention relates to a hydroformylation method by conversion of olefins or olefinically unsaturated compounds in the presence of at least one rhodium compound and in the presence of sulfonated arylphosphines in ionic liquids, which are based on a quaternary singly-charged ammonium ion or the equivalent of a multiply charged ammonium ion and organic sulfonates or sulfates.Type: GrantFiled: September 3, 2003Date of Patent: February 7, 2006Assignee: Celanese Chemicals Europe GmbHInventors: Hans Bohnen, Jurgen Herwig, Dietmar Hoff, Peter Wasserscheid, Roy van Hal
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Patent number: 6995292Abstract: Described is a process for reducing the fluoride content of products prepared in a process utilizing a fluorophosphite-containing transition metal complex catalyst, involving contacting the products with an adsorbent.Type: GrantFiled: September 16, 2002Date of Patent: February 7, 2006Assignee: Eastman Chemical CompanyInventors: Ginette Struck Tolleson, Thomas Allen Puckette
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Patent number: 6982355Abstract: A process is disclosed for making high value olefins and alcohols from synthesis gas as well as a process for an improved yield of alpha-olefins from synthesis gas. The process for hydroformulation of olefins is also provided.Type: GrantFiled: August 23, 2004Date of Patent: January 3, 2006Assignee: Syntroleum CorporationInventor: Armen N. Abazajian
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Patent number: 6969777Abstract: 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: GrantFiled: June 27, 2001Date of Patent: November 29, 2005Assignee: BASF AktiengesellschaftInventors: Helmut Walz, Willi Schönmann, Rolf Müller, Roland Krokoszinski
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Patent number: 6946580Abstract: The present invention relates to a continuous hydroformylation process for the production of an aldehyde by hydroformylation of an olefin which comprises: providing a hydroformylation zone containing a charge of a liquid reaction medium having dissolved therein a rhodium hydroformylation catalyst comprising rhodium in combination with carbon monoxide and a ligand; supplying the olefin to the hydroformylation zone; maintaining temperature and pressure conditions in the hydroformylation zone conducive to hydroformylation of the olefin; recovering from the liquid hydroformylation medium a hydroformylation product comprising aldehyde; recovering from the hydroformylation zone a stream comprising the rhodium catalyst; contacting at least a portion of the stream with a solid acidic absorbent under process conditions which allow at least some of the rhodium to become bound to the absorbent; subjecting the rhodium bound to the absorbent, under process conditions which allow desorption of the metal, to a fluid strippiType: GrantFiled: May 29, 2002Date of Patent: September 20, 2005Assignee: Davy Process Technology LimitedInventors: James Andrew Banister, George Edwin Harrison
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Patent number: 6921829Abstract: The invention generally relates to a method of formylating organic compounds in a microreactor.Type: GrantFiled: May 28, 2001Date of Patent: July 26, 2005Assignee: Merck Patent GmbHInventors: Hanns Wurziger, Guido Pieper, Norbert Schwesinger
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Patent number: 6914162Abstract: A process for preparing hydroformylation products of olefins having from 2 to 8 carbon atoms comprises a) feeding a hydrocarbon feedstock into a cracking/dehydrogenation zone and subjecting it to thermal and/or catalytic cracking and/or dehydrogenation to give an olefin-containing cracker gas, b) subjecting the cracker gas or fractions thereof to a fractionation to give at least one Ci-olefin-enriched hydrocarbon stream and at least one Ci-olefin-depleted hydrocarbon stream, c) feeding the Ci-olefin-enriched hydrocarbon stream together with carbon monoxide and hydrogen into a hydroformylation zone and reacting it in the presence of a hydroformylation catalyst, d) separating a stream consisting essentially of unreacted Ci-olefin and saturated Ci-hydrocarbon from the output from the hydroformylation zone, e) recirculating at least part of the stream consisting essentially of unreacted Ci-olefin and saturated Ci-hydrocarbon to step b), where i is an integer from to 8.Type: GrantFiled: June 27, 2001Date of Patent: July 5, 2005Assignee: BASF AktiengesellschaftInventors: Wolfgang Richter, Roland Krokoszinski, Rolf Müller, Bernhard Geissler
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Patent number: 6906225Abstract: Disclosed are novel catalyst systems comprising (1) a diorgano fluorophosphite ligand; (2) rhodium, wherein the ratio of gram moles fluorophosphite ligand (1) to gram atoms of rhodium is at least 1:1; and (3) a Group VIII metal, other than rhodium, or Group VIII metal-containing compound, in an amount effective to reduce the formation of HF during the use of the catalyst system. The presence of the other Group VIII metal decreases the amount of hydrogen fluoride produced during the use of the catalyst system. The hydrogen fluoride originates from very low level degradation of the ligand. Also disclosed are novel catalyst solutions of the aforesaid catalyst system and the use of the catalyst system in the hydroformylation of olefins to produce aldehydes.Type: GrantFiled: July 22, 2004Date of Patent: June 14, 2005Assignee: Eastman Chemical CompanyInventors: Thomas Allen Puckette, Ginette Struck Tolleson
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Patent number: 6881867Abstract: 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: GrantFiled: September 17, 2001Date of Patent: April 19, 2005Assignee: BASF AktiengesellschaftInventors: Wolfgang Ahlers, Dag Wiebelhaus, Rocco Paciello, Michael Bartsch, Robert Baumann, Dieter Vogt, Alison Hewat
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Patent number: 6849769Abstract: Essentially monounsaturated polyalkylenes having from 30 to 700 carbon atoms are continuously hydroformylated by a process in which i) a hydroformylation-active cobalt carbonyl catalyst is prepared from a catalyst precursor dissolved in an aqueous phase in the absence of the polyalkylenes, ii) the polyalkylenes are hydroformylated by means of synthesis gas in the presence of the cobalt carbonyl catalyst in a reaction zone, iii) the cobalt carbonyl catalyst is separated from the output from the reaction zone with at least partial reformation of the catalyst precursor and the catalyst precursor is recirculated to step i).Type: GrantFiled: September 11, 2001Date of Patent: February 1, 2005Assignee: BASF AktiengesellschaftInventors: Michael Röper, Heinrich-Josef Blankertz, Armin Volker Grenacher, Roland Krokoszinski, Willi Schönmann
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Patent number: 6822122Abstract: Disclosed is a method for the hydroformylation of olefins comprising 2 to 8 atoms, whereby a) an inflow containing olefins and a gas mixture containing hydrogen and carbon monoxide are fed into a reaction zone and reacted in the presence of a hydroformylation catalyst, b) the reaction product which is released from the raw hydroformylation product is redirected into the reaction zone during the extraction of a gaseous recovery flow. The inventive method is characterised in that c) the recovery flow is brought into intimate contact with a wash liquid in order to eliminate the unreacted olefins contained therein, the wash liquid being a vented hydroformylation product, and the olefin-charged wash liquid and the raw hydroformylation product are redirected for regeneration. Said inventive method enables unreacted olefins to be reclaimed to a large extent from the recovery flow.Type: GrantFiled: December 16, 2002Date of Patent: November 23, 2004Assignee: BASF AktiengesellschaftInventors: Wolfgang Richter, Roland Krokoszinski, Rolf Müller, Michael McAtee
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Patent number: 6818797Abstract: The invention pertains to a process for the hydroformylation of an ethylenically unsaturated compound in the presence of an acid with a pKa<+3, and a catalyst of a group VIII metal and a bidentate ligand of the formula: R1R2—P—X—P—R3R4 (I) wherein P is a phosphorus atom, X represents a bivalent organic bridging group, R1, R2, R3 and R4 represent independently a substituted or unsubstituted hydrocarbyl group, or R1 and R2 together with the phosphorus atom to which they are bonded and/or R3 and R4 together with the phosphorus atom to which they are bonded represent a bivalent substituted or unsubstituted cyclic group, characterized in that the process is performed in the presence of a mono tert-phosphine, wherein the ratio moles of mono tert-phosphine:moles of acid is from about 1:1 to about 10:1.Type: GrantFiled: December 16, 2003Date of Patent: November 16, 2004Assignee: Shell Oil CompanyInventors: Eit Drent, Willem Wabe Jager
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Publication number: 20040186323Abstract: The present invention relates to a continuous hydroformylation process for the production of an aldehyde by hydroformylation of an olefin which comprises: providing a hydroformylation zone containing a charge of a liquid reaction medium having dissolved therein a rhodium hydroformylation catalyst comprising rhodium in combination with carbon monoxide and a ligand; supplying the olefin to the hydroformylation zone; maintaining temperature and pressure conditions in the hydroformylation zone conducive to hydroformylation of the olefin; recovering from the liquid hydroformylation medium a hydroformylation product comprising aldehyde; recovering from the hydroformylation zone a stream comprising the rhodium catalyst; contacting at least a portion of the stream with a solid acidic absorbent under process conditions which allow at least some of the rhodium to become bound to the absorbent; subjecting the rhodium bound to the absorbent, under process conditions which allow desorption of the metal, to a fluid strippiType: ApplicationFiled: April 30, 2004Publication date: September 23, 2004Inventors: James Andrew Banister, George Edwin Harrison