Hydroformylation By Reacting Ethylenically Unsaturated Compound, Carbon Monoxide, And Gaseous Hydrogen Patents (Class 568/451)
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Publication number: 20130190537Abstract: Convert a mixture of synthesis gas and ethylene to a product stream that contains at least one C3 oxygenate using a supported, heterogeneous catalyst represented by formula RhaAgbSncXdYeOx. In the formula, X is at least one transition element other than rhodium or silver, and Y is at least one element selected from alkali metals and alkaline earth metals.Type: ApplicationFiled: September 26, 2011Publication date: July 25, 2013Applicant: Dow Global Technologies LLCInventors: Palanichamy Manikandan, Sreenivasa Rao, Phani Kiran Bollapragada
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Publication number: 20130190411Abstract: Use a transition metal-containing, Anderson-type heteropoly compound catalyst to convert synthesis gas to an oxygenate, especially an alcohol that contains from one carbon atom to six carbon atoms.Type: ApplicationFiled: September 26, 2011Publication date: July 25, 2013Applicant: Dow Global Technologies LLCInventors: Palanichamy Manikandan, David G. Barton, Dean M. Millar
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Patent number: 8492593Abstract: Amido-fluorophosphite compounds and catalyst systems comprising at least one amido-fluorophosphite ligand compound in combination with a transition metal are described. Moreover, the use of amido-fluorophosphite containing catalysts for transition metal catalyzed processes, especially to the hydroformylation of various olefins to produce aldehydes are also described.Type: GrantFiled: August 16, 2011Date of Patent: July 23, 2013Assignee: Eastman Chemical CompanyInventor: Thomas Allen Puckette
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Patent number: 8476476Abstract: In the hydroformylation of C5-C14 olefins with cobalt catalyst to produce C6-C15 oxygenates, where offgasses from the hydroformylation or cobalt removal step contain volatile cobalt compounds, the cobalt compounds are recovered by scrubbing the offgas with a liquid, and recycling the liquid to the cobalt removal step. Suitable scrubbing liquids are the organic cobalt-depleted hydroformylation reaction product or a downstream derivative thereof, or an aqueous solution of a Co2+ salt, preferably such salt of formic acid.Type: GrantFiled: August 19, 2009Date of Patent: July 2, 2013Assignee: ExxonMobil Chemical Patents Inc.Inventors: Eddy T. A. Van Driessche, Ronald D. Garton, Raphael F. Caers
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Publication number: 20130158282Abstract: The present invention relates to POSS-modified ligands and to the use thereof in catalytically effective compositions in hydroformylation.Type: ApplicationFiled: March 1, 2011Publication date: June 20, 2013Applicant: Evonik Oxeno GmbHInventors: Andrea Christiansen, Robert Franke, Dieter Hess, Dirk Fridag, Dieter Vogt, Christian Mueller, Michele Janssen
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Publication number: 20130150618Abstract: A mixing apparatus 100 for mixing at least two fluids, the mixing apparatus 100 comprising a shaft 120 rotatable about its longitudinal axis 121, a first 122 and a second 124 radially extending impeller mounted on the shaft 120 and respectively axially spaced apart, characterised in that the first impeller 122 comprises a plurality of curved blades 125 operable to move said fluids in an axial direction towards the second impeller 124, and the second impeller 124 comprises a plurality of curved blades 125 operable to move said fluids in an axial direction towards the first impeller 122.Type: ApplicationFiled: February 8, 2013Publication date: June 13, 2013Applicant: Lucite International UK LimitedInventor: Lucite International UK Limited
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Patent number: 8445728Abstract: The invention relates to a method for reprocessing a liquid product of a hydroformylation reaction, wherein the liquid phase produced in a release stage is supplied to a separating device from which a liquid flow containing rhodium is guided away via a filter, where solids thereby separated are taken out of the process and the filtrate obtained is guided back into the hydroformylation reaction.Type: GrantFiled: March 18, 2010Date of Patent: May 21, 2013Assignee: Oxea GmbHInventors: Wolfgang Greb, Rainer Lukas, Klaus Schmid, Wolfgang Zgorzelski, Jörg Arnold
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Patent number: 8404903Abstract: A process of controlling heavies in a recycle catalyst stream, particularly, for use in a continuous hydroformylation process of converting an olefin with synthesis gas in the presence of a hydroformylation catalyst to form an aldehyde product stream with subsequent separation of the catalyst for recycle to the hydroformylation step. Heavies are controlled, and preferably reduced, by means of feeding a recycle gas stream, taken as a portion of an over-head stream from a condenser, back to a vaporizer wherein the aldehyde product stream is separated.Type: GrantFiled: July 2, 2009Date of Patent: March 26, 2013Assignees: Dow Technology Investments, LLC, BASF SEInventors: Irvin B. Cox, Thomas C. Eisenschmid, Ronald R. Peterson, Rainer Papp, Ludwig Herk, Anthony G. Abatjoglou
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Patent number: 8389774Abstract: The invention relates to a device and a method for the continuous reaction of a liquid and a second fluid, wherein the device comprises at least two jet loop reactors interconnected in parallel and common outer liquid recirculation.Type: GrantFiled: July 9, 2009Date of Patent: March 5, 2013Assignee: Evonik Oxeno GmbHInventors: Marc Becker, Robert Franke, Wilfried Bueschken, Armin Boerner, Jens Holz
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Patent number: 8389775Abstract: The invention relates to a process for preparing polyether alcohols, which comprises the steps a) reaction of an unsaturated natural oil or fat with a mixture of carbon monoxide and hydrogen, b) reaction of the mixture from step a) with hydrogen, c) reaction of the product from step b) with an alkylene oxide in the presence of a catalyst.Type: GrantFiled: January 26, 2009Date of Patent: March 5, 2013Assignee: BASF SEInventors: Darijo Mijolovic, Andrea Haunert, Andreas Kunst, Stephan Bauer, Qiang Miao, Berend Eling
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Publication number: 20120277474Abstract: A continuous process for carbonylation of ethylene in a liquid phase using carbon monoxide, a co-reactant and a suitable catalyst system, including: (i) forming a liquid phase comprising the co-reactant and a suitable catalyst system obtainable by combining: (a) a group VIII metal/compound; (b) a ligand of general formula (I) ?and c) optionally, a source of anions; wherein Q1 is optionally phosphorous; (ii) forming a gaseous phase in contact with the liquid phase by providing at least an ethylene gas input feed stream and a carbon monoxide gas input feed stream wherein the ethylene:CO molar ratio entering the liquid phase from the input feed streams is greater than 2:1; (iii) reacting ethylene with carbon monoxide in the presence of the co-reactant, and of the suitable catalyst system in the liquid phase; wherein the ethylene:CO gas molar ratio in the gaseous phase is between 20:1 and 1000:1 or wherein the molar ratio of ethylene:CO in the liquid phase is greater than 10:1.Type: ApplicationFiled: December 15, 2010Publication date: November 1, 2012Applicant: LUCITE INTERNATIONAL UK LIMITEDInventors: Eastham Graham Ronald, Neil Tindale
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Publication number: 20120253080Abstract: Control of an in-series, multiple, e.g., two, reaction zone, hydroformylation process for producing normal (N) and iso (I) aldehydes at a N:I ratio, the process comprising contacting an olefinically unsaturated compound, e.g., propylene, with carbon monoxide, hydrogen and a catalyst comprising (A) a transition metal, e.g., rhodium, (B) an organobisphosphite, and (C) an organomonophosphite ligand, the contacting conducted in first and subsequent reaction zones and at hydroformylation conditions comprising an olefinically unsaturated compound partial pressure in each zone, the control exercised by decreasing the olefinically unsaturated compound partial pressure in the first reaction zone to decrease the N:I ratio or increasing the olefinically unsaturated compound partial pressure in the first reaction zone to increase the N:I ratio.Type: ApplicationFiled: December 15, 2010Publication date: October 4, 2012Inventors: Thomas C. Eisenschmid, Glenn A. Miller, Jeffrey S. Sawrey, Michael A. Brammer
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Patent number: 8247618Abstract: Oxidative recovery methods that use oxygen or air for recovery of homogeneous metal catalysts, such as cobalt catalysts, used in for example hydroformylation processes, can be hazardous. Explosive or flammable gas mixtures may be generated inside the process equipment, which can deflagrate upon any ignition source such as a static electricity discharge. The use of a flammable diluent has been found to be a very effective way of optimizing the recovery method, by bringing the resulting gas mixtures above their upper flammability limit. The offgas produced is then also easier to dispose of as a fuel, as compared to when a non-flammable diluent is used.Type: GrantFiled: March 31, 2008Date of Patent: August 21, 2012Assignee: ExxonMobil Chemical Patents Inc.Inventors: Kenneth J. Buturla, James T. Ritchie, Ronald D. Garton, Eddy T. A. Van Driessche
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Patent number: 8226829Abstract: Process for separating a dissolved complex catalyst of a metal of group 4, 5, 6, 7, 8, 9 or 10 of the Periodic Table of the Elements and/or any free organophosphorus ligand present from a nonaqueous hydroformylation reaction mixture which contains an aldehyde product and an organic solvent at least one membrane which is more permeable to the hydroformylation product than to the organophosphorus ligand, the separation being carried out under a carbon monoxide partial vapor pressure of more than 200 kPa.Type: GrantFiled: September 8, 2006Date of Patent: July 24, 2012Assignee: Evonik Oxenc GmbHInventors: Klaus-Diether Wiese, Goetz Baumgarten, Franz-Felix Kuppinger, Oliver Moeller, Dagmara Ortmann, Cornelia Borgmann, Wilfried Bueschken
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Patent number: 8211949Abstract: Novel mixtures of long-chain (C10-C20) olefins are functionalized by conversion to aldehydes using an OXO process, or to sulfates, sulfonates, sulfones, sulfides, or sulfoxides by direct sulfonation. The aldehydes may then be hydrogenated to form alcohols, or aminated to form amines or amides. The olefins starting mixture may be acquired as a byproduct of the tetramerization of ethylene in the presence of certain chromium-containing tetramerization catalysts. The functionalized mixtures, and derivatives prepared therefrom such as alkoxylates prepared from the alcohols, may be useful as surfactants that may offer improved performance in many applications, while their preparation based on a byproduct mixture reduces their cost and also reduces waste-handling issues for this non-targeted stream.Type: GrantFiled: September 16, 2008Date of Patent: July 3, 2012Assignee: Dow Global Technologies LLCInventors: Pierre T. Varineau, Brian W. Kolthammer, Aaron W. Sanders, David A. Wilson, Kara S. Weber, Robert Kirk Thompson, Cynthia L. Rand, Thomas C. Eisenschmid
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Patent number: 8178730Abstract: Mixed butene streams containing butene-1 and isobutylene and optionally butene-2 are hydroformylated under conditions that hydroformylates all the monomers to yield a mixture of valeraldehydes.Type: GrantFiled: September 21, 2011Date of Patent: May 15, 2012Assignee: ExxonMobil Chemical Patents Inc.Inventors: Raphael F. Caers, Eddy Theophile Van Driessche, Hubertus J. Beckers, Luc Roger Marc Martens, Georges Marie Mathys, John Richard Shutt
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Patent number: 8178729Abstract: Disclosed is a process for hydroformylation of ?-olefin wherein said ?-olefin is reached with carbon monoxide or carbon monoxide and hydrogen and/or a reducing agent in presence of a catalyst complex based on a rhodium precursor and a ligand mixture comprising at least 1% by weight of trphenylphosphine and at least 5% by weight of diphenylcyclohexylphosphine, tris-(o-tolyl)phosphine, tris-(p-tolyl)phosphine or (2-methyl-phenyl)diphenylphospine.Type: GrantFiled: March 15, 2006Date of Patent: May 15, 2012Assignee: Perstorp Specialty Chemicals ABInventors: Esko Karvinen, Juha Lehtonen, Joni Kunnas, Merja Harteva
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Patent number: 8173847Abstract: Aldehydes are produced by unmodified rhodium catalyzed hydroformylation process in a homogeneous organic phase using a solution of unmodified rhodium catalyst and an organic acid in a total amount, calculated as acid equivalent, of from greater than 3 moles to 3000 moles of acid per mole of rhodium. The organic acid is selected from: saturated aliphatic monocarboxylic acids having from 5 to 13 carbon atoms in the molecule; saturated aliphatic dicarboxylic acids having from 5 to 13 carbon atoms in the molecule; sulphonic acids having from 1 to 12 carbon atoms in the molecule; and combinations thereof. Use of the process can lead to either a significant increase in conversion without reducing selectivity for the desired aldehyde or a reduction in the specific use of rhodium.Type: GrantFiled: October 28, 2008Date of Patent: May 8, 2012Assignee: Oxea GmbHInventors: Andreas Fischbach, Klaus Schmid, Christoph Balzarek, Wolfgang Dukat, Sandra Fürmeier, Rainer Lukas, Horst Scholz, Edgar Storm
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Patent number: 8138379Abstract: The invention relates to a one-stage continuous process for hydroformylating olefins having at least 5 carbon atoms to the corresponding aldehydes and/or alcohols having at least 6 carbon atoms in the presence of unmodified cobalt catalysts in a process in which, in the presence of an aqueous phase and of an organic phase, catalyst formation, catalyst extraction and hydroformylation proceed in the same reactor, which is characterized in that more aqueous cobalt salt solution is fed into the reactor as an aqueous phase with the liquid reaction mixture and is discharged from the reactor with the gas phase, and in that the level of the aqueous bottom phase is kept constant by continuously conducting a portion of the aqueous bottom phase out of the reactor.Type: GrantFiled: October 28, 2008Date of Patent: March 20, 2012Assignee: Evonik Oxeno GmbHInventors: Hans-Gerd Lueken, Stefan Drees, Alfred Kaizik, Wilfried Bueschken
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Patent number: 8129571Abstract: The invention relates to a process for the continuous preparation of aldehydes and/or alcohols having at least 6 carbon atoms by multistage hydroformylation of olefins or olefin mixtures having at least 5 carbon atoms in the presence of unmodified cobalt complexes, in which at least two reactors are operated at different temperatures in the temperature range from 100 to 220° C. and pressures of from 100 to 400 bar, which is characterized in that a) one reactor is operated at temperatures above 160° C.Type: GrantFiled: October 28, 2008Date of Patent: March 6, 2012Assignee: Evonik Oxeno GmbHInventors: Hans-Gerd Lueken, Alfred Kaizik, Stefan Drees, Wilfried Bueschken
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Patent number: 8119004Abstract: A liquid-liquid extraction process that uses counterflowing liquid phases, especially in conjunction with a reciprocating plate extraction column, wherein one of the liquid phases has a lower density than the other and is at least partially saturated with a dispersible gas, requires less plate stack height or a smaller column diameter when plate-to-plate spacing is non-uniform rather than uniform and such non-uniform plate-to-plate spacing includes greater plate-to-plate spacing proximate to raffinate liquid discharge than proximate to feed of the lower density liquid phase.Type: GrantFiled: July 26, 2007Date of Patent: February 21, 2012Assignee: Dow Global Technologies LLCInventors: Timothy C. Frank, John J. Anderson
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Patent number: 8110709Abstract: The present invention relates to a process for the hydroformylation of ethylenically unsaturated compounds by reaction with carbon monoxide and hydrogen in the presence of a catalytically active fluid which comprises a dissolved metal complex of a metal of transition group VIII of the Periodic Table of the Elements with at least one phosphoramidite compound as ligand, wherein the fluid is brought into contact with a base.Type: GrantFiled: October 22, 2004Date of Patent: February 7, 2012Assignee: BASF SEInventors: Rainer Papp, Wolfgang Ahlers, Thomas Mackewitz, Rocco Paciello, Martin Volland
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Patent number: 8022256Abstract: Mixed butene streams containing butene-1 and isobutylene and optionally butene-2 are hydroformylated under conditions that hydroformylates all the monomers to yield a mixture of valeraldehydes. Higher temperatures and/or longer residence times and/or higher partial pressure of carbon monoxide than in conventional processes are used to ensure hydroformylation of all the monomers.Type: GrantFiled: September 17, 2004Date of Patent: September 20, 2011Assignee: ExxonMobil Chemical Patents Inc.Inventors: Raphael F. Caers, Eddy Theophile Van Driessche, Hubertus J. Beckers, Luc Roger Marc Martens, Georges Maria Mathys, John Richard Shutt
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Patent number: 7977447Abstract: A method for forming a monomeric carbonate includes the step of combining a monofunctional alcohol or a difunctional diol with an ester-substituted diaryl carbonate to form a reaction mixture. Similarly, a method for forming a monomeric ester includes the step of combining a monofunctional carboxylic acid or ester with an ester-substituted diaryl carbonate to form a reaction mixture. These methods further include the step of allowing the reaction mixtures to react to form a monomeric carbonate or a monomeric ester, respectively.Type: GrantFiled: December 24, 2008Date of Patent: July 12, 2011Assignee: Sabic Innovative Plastics IP B.V.Inventors: Hatem Abdallah Belfadhel, Hans-Peter Brack, Ricardo Godoy-Lopez, Dennis James Patrick Maria Willemse
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Publication number: 20110137071Abstract: Mixed butene streams containing butene-1 and isobutylene and optionally butene-2 are hydroformylated under conditions that hydroformylates all the monomers to yield a mixture of valeraldehydesType: ApplicationFiled: February 17, 2011Publication date: June 9, 2011Inventors: Raphael F. Caers, Eddy Theophile Van Driessche, Hubertus J. Beckers, Luc Roger Mare Martens, Georges Marie Mathys, John Richard Shutt
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Publication number: 20110112216Abstract: The invention is directed to a process and apparatus for carrying out reactions with reaction mixtures comprising different physical phases. In a first aspect, the present invention is directed to a process for carrying out chemical reactions comprising a step wherein a reaction mixture comprising at least two different physical phases, wherein at least one of these phases being liquid, is subjected to the action of Dean vortices, which Dean vortices result from said liquid flowing through a channel having at least two curvatures, wherein the channel comprises for at least a fraction of its total length a smooth inner surface.Type: ApplicationFiled: June 10, 2009Publication date: May 12, 2011Applicant: NEDERLANDSE ORGANISATIE VOOR TOEGEPAST- NATUURWETENSCHAPPELIJK ONDERZOEK TNOInventors: Annemieke Van De Runstraat, Peter Geerdink, Earl Lawrence Vincent Goetheer
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Patent number: 7939694Abstract: The present invention relates to a method for preparing aldehydes by reacting olefins with a synthesis gas including carbon monoxide and hydrogen, and to an apparatus therefore. More particularly, the present invention relates to a method for preparing aldehydes, characterized by spraying and supplying olefins, synthesis gas including carbon monoxide and hydrogen, and a catalyst composition into an oxo reactor through a nozzle, and to an apparatus therefore. According to the present invention, the hydroformylation efficiency can be improved, thereby obtaining desirable aldehydes with a high yield.Type: GrantFiled: May 29, 2008Date of Patent: May 10, 2011Assignee: LG Chem, Ltd.Inventors: Moo-Ho Hong, Dong-Hyun Ko, Sang-Oeb Na, Sung-Shik Eom, Sang-Gi Lee, O-Hark Kwon, Dae-Chul Kim, Jae-Hui Choi
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Patent number: 7935850Abstract: Increasing the propylene content of the propylene feed delivered to a continuous hydroformylation process from the 95 mole % maximum level that is usual in typical chemical grade propylene to at least 97 mole %, for example to the 97.5% level obtainable from the conversion of oxygenates to olefins or the 99.5% level of polymer grade propylene, enables adjustments to be made in the syngas feed to the process. This leads to surprising improvements in hydroformylation product yield, in reactor capacity utilization and in the reduction of amounts of waste gases.Type: GrantFiled: January 28, 2005Date of Patent: May 3, 2011Assignee: ExxonMobil Chemical Patents Inc.Inventors: Raphael Frans Caers, Eddy Theophyle Andrea Van Driessche
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Patent number: 7910782Abstract: In a hydroformylation reaction, the circulation and recovery of cobalt carbonyl in a cobalt catalyst cycle using carbonylate as an intermediate and acidification thereof, is improved by supplying an aqueous sulfuric acid solution containing less than 16% wt of sulfuric acid to the carbonylate to control sulfuric acid concentration in the carbonylate/acid mixture, before accounting for any acid consuming reaction, to a value of from 2% to 10% by weight. Single step and multistage liquid/liquid extraction techniques as well as vapor/liquid extraction techniques followed by the absorption of cobalt from the vapor in an organic liquid both benefit from this improvement.Type: GrantFiled: March 28, 2008Date of Patent: March 22, 2011Assignee: ExxonMobil Chemical Patents Inc.Inventors: Eddy T. A. Van Driessche, Arie Van Vliet, Raphael Frans Caers, Hubertus Joseph Beckers, Ronald Dean Garton, Bertrand Raymond Da Cruz, Michel J. P. Lepagnol, Edwin Kooke
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Patent number: 7875254Abstract: The invention relates to improvements in internal loop reactors. The reactor of the invention is characterized by a plurality of cooling tubes which form the annulus between the riser and the downcomer path of said internal loop reactor. The reactor also provides improvements in hydroformylation reactions using the improved reactor.Type: GrantFiled: January 5, 2010Date of Patent: January 25, 2011Assignee: ExxonMobil Chemical Patents Inc.Inventors: Ronald Dean Garton, Matthew Findlay, Krishnan Sankaranarayanan, Arie Van Vliet
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Publication number: 20100256422Abstract: Aldehydes are produced by unmodified rhodium catalyzed hydroformylation process in a homogeneous organic phase using a solution of unmodified rhodium catalyst and an organic acid in a total amount, calculated as acid equivalent, of from greater than 3 moles to 3000 moles of acid per mole of rhodium. The organic acid is selected from: saturated aliphatic monocarboxylic acids having from 5 to 13 carbon atoms in the molecule; saturated aliphatic dicarboxylic acids having from 5 to 13 carbon atoms in the molecule; sulphonic acids having from 1 to 12 carbon atoms in the molecule; and combinations thereof. Use of the process can lead to either a significant increase in conversion without reducing selectivity for the desired aldehyde or a reduction in the specific use of rhodium.Type: ApplicationFiled: October 28, 2008Publication date: October 7, 2010Inventors: Andreas Fischbach, Klaus Schmid, Christoph Batzarek, Wolfgang Dukat, Sandra Fürmeier, Rainer Lukas, Horst Scholz, Edgar Storm
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Publication number: 20100249464Abstract: The invention relates to a one-stage continuous process for hydroformylating olefins having at least 5 carbon atoms to the corresponding aldehydes and/or alcohols having at least 6 carbon atoms in the presence of unmodified cobalt catalysts in a process in which, in the presence of an aqueous phase and of an organic phase, catalyst formation, catalyst extraction and hydroformylation proceed in the same reactor, which is characterized in that more aqueous cobalt salt solution is fed into the reactor as an aqueous phase with the liquid reaction mixture and is discharged from the reactor with the gas phase, and in that the level of the aqueous bottom phase is kept constant by continuously conducting a portion of the aqueous bottom phase out of the reactor.Type: ApplicationFiled: October 28, 2008Publication date: September 30, 2010Applicant: Evonik Oxeno GmbHInventors: Hans-Gerd Lueken, Stefan Drees, Alfred Kaizik, Wilfried Bueschken
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Publication number: 20100234628Abstract: The present invention relates to a process for the preparation of indium acetate comprising the steps: (a) reacting an indium compound with an alkaline compound in a protic solvent to obtain an iridium containing precipitate, where the reaction is conducted in the presence of at least one component (i) selected from oxalic acid, a salt of oxalic acid, formic acid and a salt of formic acid, (b) reacting the precipitate in the presence of at least (i) one compound selected from oxalic acid, a salt of oxalic acid, formic acid and a salt of formic acid, and (ii) CH3CO2H and/or CH3(CO)O(CO)CH3 to give an iridium acetate containing solution. The invention also relates to indium acetate having a low halide content, to an indium containing precipitate and to uses of the iridium containing precipitate of the present invention and the iridium acetate of the present invention.Type: ApplicationFiled: May 24, 2006Publication date: September 16, 2010Inventors: Ralf Karch, Bernd Kayser, Andreas Rivas-Nass, Jurgen Bodo Widmer, Roland Winde, Eileen Worner
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Patent number: 7781620Abstract: A hydroformylation process comprising reacting, in a reactor system comprising one or more feed streams, a reaction environment and an output stream, 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 the reaction environment, which comprises 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 a temperature which is at least 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 140° C. to 220° C., and the temperature of the earlier reaction zone is at least 130° C., and wherein water is added into the reactor system.Type: GrantFiled: December 19, 2007Date of Patent: August 24, 2010Assignee: Shell Oil CompanyInventor: Wilhelmus Petrus Mul
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Publication number: 20100210880Abstract: The invention relates to a process for the continuous preparation of aldehydes and/or alcohols having at least 6 carbon atoms by multistage hydroformylation of olefins or olefin mixtures having at least 5 carbon atoms in the presence of unmodified cobalt complexes, in which at least two reactors are operated at different temperatures in the temperature range from 100 to 220° C. and pressures of from 100 to 400 bar, which is characterized in that a) one reactor is operated at temperatures above 160° C.Type: ApplicationFiled: October 28, 2008Publication date: August 19, 2010Applicant: Evonik Oxeno GmbHInventors: Hans-Gerd Lueken, Alfred Kaizik, Stefan Drees, Wilfried Bueschken
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Patent number: 7767770Abstract: A method for producing a mixture of ethylene and carbon monoxide by contacting ethane and an oxygen source with a catalyst comprising synthetic cryptomelane or octahedral molecular sieve. The method further comprises condensing the alkyl propionate with formaldehyde to produce an alkyl methacrylate.Type: GrantFiled: September 17, 2009Date of Patent: August 3, 2010Assignee: Rohm and Haas CompanyInventors: Scott Han, Daniel J. Martenak, Lei Jin, Steven Lawrence Suib
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Publication number: 20100190874Abstract: The invention relates to a process of making a syngas mixture containing hydrogen, carbon monoxide and carbon dioxide, comprising a step of contacting a gaseous feed mixture containing carbon dioxide and hydrogen with a catalyst, which catalyst substantially consists of Mn oxide and an oxide of at least one member selected from the group consisting of Crl Ni, La, Ce, W, and Pt. This process enables hydrogenation of carbon dioxide into carbon monoxide with high selectivity, and good catalyst stability over time and under variations in processing conditions. The process can be applied separately, but can also be integrated with other processes, both up-stream and/or down-stream; like methane reforming or other synthesis processes for making products like alkanes, aldehydes, or alcohols.Type: ApplicationFiled: April 23, 2008Publication date: July 29, 2010Inventors: Agaddin M.Kh. Mamedov, Abdulaziz A.M. Al-Jodai, Ijaz C. Ahmed, Mubarak Bashir
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Publication number: 20100185018Abstract: The present invention relates to a method for preparing aldehydes by reacting olefins with a synthesis gas including carbon monoxide and hydrogen, and to an apparatus therefore. More particularly, the present invention relates to a method for preparing aldehydes, characterized by spraying and supplying olefins, synthesis gas including carbon monoxide and hydrogen, and a catalyst composition into an oxo reactor through a nozzle, and to an apparatus therefore. According to the present invention, the hydroformylation efficiency can be improved, thereby obtaining desirable aldehydes with a high yield.Type: ApplicationFiled: May 29, 2008Publication date: July 22, 2010Applicant: LG CHEM, LTD.Inventors: Moo-Ho Hong, Dong-Hyun Ko, Sang-Oeb Na, Sung-Shik Eom, Sang-Gi Lee, O-Hark Kwon, Dae-Chul Kim, Jae-Hui Choi
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Patent number: 7737315Abstract: 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: January 28, 2009Date of Patent: June 15, 2010Assignee: ExxonMobil Chemical Patents Inc.Inventors: Stephen Harold Brown, Georges Marie Mathys
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Publication number: 20100145104Abstract: Modular reactor panel (1) for catalytic processes, comprising a feed header (5), a product header (7) and adjacent channels (3), each channel (3) having a length, running from an entrance end to an exit end, and wherein the entrance ends are directly connected to and open into the feed header (5) and the exit ends are directly connected to and open into the product header (7) and wherein the feed header (5) has at least one connection (9) to a feed line (51) and the product header (7) has at least one connection to a product line (55) and wherein part (21) of at least one of the feed header (5) and the product header (7) is detachable giving access to the channel ends and reactor comprising a housing (47) containing one or more of said reactor panels (1, 29), the reactor further comprising a feed line (51) and a product line (55), the panels (29) being connected to the feed line (51) and to product line (55).Type: ApplicationFiled: June 25, 2008Publication date: June 10, 2010Applicant: SAUDI BASIC INDUSTRIES CORPORATIONInventor: Peter Hubertus Kosters
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Patent number: 7728178Abstract: This invention relates to a process for the production of aldehydes/alcohols and alkyl benzene. According to the invention, a hydrocarbon feed stream containing olefins and paraffins having an average number of carbon atoms from 10 to 18 per molecule, typically derived from the condensation product of a Fischer-Tropsch reaction is subjected to a hydroformylation reaction to provide a hydroformylation product containing aldehydes/alcohols and paraffins. An aldehyde/alcohol product is separated from the paraffins in the hydroformylation product to provide an aldehyde/alcohol product stream and a paraffin stream. The paraffin stream separated from the hydroformylation product is then subjected to a dehydrogenation reaction to form a dehydrogenation product containing olefins and paraffins, and the dehydrogenation product is subjected to an alkylation reaction to convert olefins to alkyl benzene.Type: GrantFiled: August 31, 2006Date of Patent: June 1, 2010Assignee: Sasol Technology (Proprietary) LimitedInventors: Ivan Philip Greager, James Christoffel Crause
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Publication number: 20100130792Abstract: The present invention relates to a catalyst composition that includes a bis-phosphite ligand, a poly-phosphite ligand or a mono-phosphite ligand, and a transition metal catalyst, and a hydroformylation reaction using the same. The catalyst composition has the excellent catalytic activity, and the normal/iso (N/I) selectivity of aldehyde generated by the hydroformylation reaction using the same is increased.Type: ApplicationFiled: April 8, 2008Publication date: May 27, 2010Applicant: LG CHEM, LTD.Inventors: Jae-Hui Choi, Dong-Hyun Ko, Sung-Shik Eom, Ji-Joong Moon, Sang-Gi Lee, O-Hark Kwon
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Publication number: 20100105956Abstract: The invention relates to improvements in internal loop reactors. The reactor of the invention is characterized by a plurality of cooling tubes which form the annulus between the riser and the downcomer path of said internal loop reactor. The reactor also provides improvements in hydroformylation reactions using the improved reactor.Type: ApplicationFiled: January 5, 2010Publication date: April 29, 2010Inventors: Ronald Dean Garton, Matthew Findlay, Krishnan Sankaranarayanan, Arie Van Vliet
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Patent number: 7674937Abstract: This invention is directed to a class of compounds that can be both monodentate and bidentate in their association with a transition metal to form a catalyst for reactions such as the hydroformylation of olefins to produce aldehydes. The compounds contain two phosphorus atoms having different steric and/or electronic nature. In hydroformylation catalysts, the compounds advantageously can produce a variable n/iso product mixture of aldehyde products that can be varied by simply changing process variables such as [H2]/[CO] partial pressure gas ratio or temperature/inert gas partial pressure.Type: GrantFiled: May 28, 2008Date of Patent: March 9, 2010Assignee: Eastman Chemical CompanyInventors: Ginette Struck Tolleson, Thomas Allen Puckette
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Publication number: 20100036003Abstract: A hydroformylation process comprising reacting, in a reactor system comprising one or more feed streams, a reaction environment and an output stream, 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 the reaction environment, which comprises 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 a temperature which is at least 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 140° C. to 220° C., and the temperature of the earlier reaction zone is at least 130° C., and wherein water is added into the reactor system.Type: ApplicationFiled: December 19, 2007Publication date: February 11, 2010Inventor: Wilhelmus Petrus Mul
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Patent number: 7652173Abstract: 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: GrantFiled: August 31, 2006Date of Patent: January 26, 2010Assignee: Sasol Technology (Proprietary) LimitedInventor: James Christoffel Crause
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Publication number: 20100010270Abstract: In a method for hydroformylating olefinically unsaturated compounds by means of a cobalt-based catalyst, used in a non-aqueous ionic liquid, liquid at a temperature below 100° C. and comprising at least one cation Q+ and at least one anion A?, said method comprising at least a stage of reaction under pressure and at least a stage of separation of the phases by decantation, recycling of the catalyst is improved: through the use of a ligand selected from among the Lewis bases, more particularly pyridine derivatives, and simultaneously through the addition of this ligand in a post-reaction stage. At the end of this process, the organic phase containing the reaction products can be recovered and the ionic liquid phase containing the catalyst can be recycled to the hydroformylation reactor.Type: ApplicationFiled: June 22, 2007Publication date: January 14, 2010Applicant: IFPInventors: Helene Olivier-Bourbigou, Lucien Saussine, Lionel Magna, David Proriol
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Patent number: 7615645Abstract: The invention relates to a method for the continuous production of aldehydes by the isomerising hydroformylation in a homogenous phase of olefin compositions by means of a synthesis gas, in the presence of a homogeneous rhodium catalyst that is complexed with an organophosphorus ligand containing oxygen atoms and/or nitrogen atoms and a free ligand. The production is carried out at high temperature and high pressure in a multi-stage reaction system consisting of at least two reaction zones. According to the method, the olefin composition is first reacted in a first reaction zone or a group of several first reaction zones at a total pressure of between 10 and 40 bar, using a synthesis gas with a CO/H2 molar ratio of between 4:1 and 1:2 until a 40 to 95% conversion of the ?-olefins is obtained.Type: GrantFiled: October 14, 2004Date of Patent: November 10, 2009Assignee: BASF AktiengesellschaftInventors: Martin Volland, Thomas Mackewitz, Wolfgang Ahlers, Ansgar Schäfer, Wolfgang Richter, Rocco Paciello
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Patent number: 7582802Abstract: Propylene streams obtained by the conversion of oxygenates to olefins are used as feeds for hydroformylation. The streams may contain measurable amounts of dimethyl ether without adversely impacting the hydroformylation.Type: GrantFiled: January 28, 2005Date of Patent: September 1, 2009Assignee: ExxonMobil Chemical Patents Inc.Inventors: Raphael Frans Caers, Hubertus Joseph Beckers, Eddy Theophyle Andrea Van Driessche, Luc Roger Marc Martens, John Stephen Godsmark, John Richard Shutt
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Publication number: 20090118548Abstract: A non-aqueous hydroformylation process with liquid catalyst recycle involving a hydroformylation step and one or more stages of phase separation to recover a high molecular weight aldehyde product with efficient recovery of rhodium catalyst. The process includes a hydroformylation step to prepare a non-aqueous hydroformylation reaction product composition comprising one or more aldehyde products, one or more conjugated polyolefins, a rhodium-organophosphorus ligand complex, free organophosphorus ligand, and an organic solubilizing agent for said complex and said free ligand, and thereafter one or more stages of phase separation using added water under a carbon monoxide gas, hydrogen gas, or a mixture thereof. The process requires a specific range of total pressure for the hydroformylation, a specific range of total pressure for at least one of the separation stages, and a minimum sum of the total pressure of the hydroformylation step and the total pressure of the separation stage containing said gas.Type: ApplicationFiled: April 17, 2007Publication date: May 7, 2009Inventors: Wei-Jun Peng, Kurt D. Olson, Donald L. Morrison, Brian M. Roesch, Donald L. Bunning, Jeffrey G. Hippler, Vincent J. Stricker