Hydroformylation By Reacting Ethylenically Unsaturated Compound, Carbon Monoxide, And Gaseous Hydrogen Patents (Class 568/451)
  • Patent number: 7501548
    Abstract: 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: Grant
    Filed: March 10, 2006
    Date of Patent: March 10, 2009
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Stephen Harold Brown, Georges Marie Mathys
  • Publication number: 20090054696
    Abstract: 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: Application
    Filed: August 31, 2006
    Publication date: February 26, 2009
    Inventor: James Christoffel Crause
  • Patent number: 7495133
    Abstract: (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: Grant
    Filed: January 27, 2005
    Date of Patent: February 24, 2009
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Cornelia Borgmann, Detlef Selent, Armin Boerner, Klaus-Diether Wiese, Dagmara Ortmann, Oliver Moeller, Dieter Hess
  • Publication number: 20090048411
    Abstract: 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: Application
    Filed: August 5, 2008
    Publication date: February 19, 2009
    Inventors: Abraham Benderly, Scott Han, Mark Anthony Silvano, Donald Lee Zolotorofe
  • Patent number: 7485759
    Abstract: 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: Grant
    Filed: January 24, 2008
    Date of Patent: February 3, 2009
    Assignee: Dow Technology Investments LLC
    Inventors: John R. Briggs, Wei-Jun Peng, Brian M. Roesch, Anthony G. Abatjoglou, Donald L. Morrison
  • Patent number: 7446231
    Abstract: 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: Grant
    Filed: July 19, 2005
    Date of Patent: November 4, 2008
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Ronald R Peterson, Thomas C. Eisenschmid, David R. Bryant, Morteza Mokhtarzadeh
  • Patent number: 7442842
    Abstract: 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: Grant
    Filed: November 24, 2004
    Date of Patent: October 28, 2008
    Assignee: BASF SE
    Inventors: Christoph Jäkel, Martin Volland, Thomas Mackewitz, Rocco Paciello, Bernhard Breit, Wolfgang Seiche, Martine Weis, Christoph Waloch
  • Patent number: 7420092
    Abstract: 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: Grant
    Filed: November 7, 2005
    Date of Patent: September 2, 2008
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Yuichi Fujita, Fumitaka Utsumi
  • Patent number: 7405329
    Abstract: 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: Grant
    Filed: December 16, 2004
    Date of Patent: July 29, 2008
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Stephen Wayne Beadle, Ronald Dean Garton, Hubertus Joseph Beckers, Raphael Frans Caers, Arie Van Vliet, John J. Houben
  • Patent number: 7365234
    Abstract: 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: Grant
    Filed: March 16, 2007
    Date of Patent: April 29, 2008
    Assignee: University of Kansas
    Inventors: Bala Subramaniam, Jon A. Tunge, Hong Jin, Anindya Ghosh
  • Patent number: 7351868
    Abstract: 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: Grant
    Filed: June 28, 2004
    Date of Patent: April 1, 2008
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John R. Briggs, Wei-Jun Peng, Brian M. Roesch, Anthony G. Abatjoglou, Donald L. Morrison
  • Patent number: 7329783
    Abstract: 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: Grant
    Filed: June 28, 2006
    Date of Patent: February 12, 2008
    Assignee: Shell Oil Company
    Inventor: Wilhelmus Petrus Mul
  • Patent number: 7317130
    Abstract: 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: Grant
    Filed: August 7, 2003
    Date of Patent: January 8, 2008
    Assignee: OXENO Olefinchemie GmbH
    Inventors: Oliver Möller, Dirk Fridag, Cornelia Borgmann, Dieter Hess, Klaus-Diether Wiese
  • Patent number: 7294729
    Abstract: 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: Grant
    Filed: September 26, 2003
    Date of Patent: November 13, 2007
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Wei-Jun Peng, Johnathan E Holladay
  • Publication number: 20070219399
    Abstract: 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: Application
    Filed: March 16, 2007
    Publication date: September 20, 2007
    Applicant: University of Kansas
    Inventors: Bala Subramaniam, Jon A. Tunge, Hong Jin, Anindya Ghosh
  • Patent number: 7270985
    Abstract: 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: Grant
    Filed: September 14, 2004
    Date of Patent: September 18, 2007
    Assignee: Council of Scientific & Industrial Research
    Inventors: James Kanagaraj, Gopala Suseela Rajakumar, Sayeed Sadulla
  • Patent number: 7259279
    Abstract: 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: Grant
    Filed: November 15, 2005
    Date of Patent: August 21, 2007
    Assignee: Oxea GmbH
    Inventors: Dietmar Thiel, Carl Dieter Frohning
  • Patent number: 7232931
    Abstract: 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: Grant
    Filed: December 5, 2002
    Date of Patent: June 19, 2007
    Assignee: OXENO Olefinchemie GmbH
    Inventors: Walter Toetsch, Alfred Kaizik, Hermann-Josef Schulte-Althoff
  • Patent number: 7227045
    Abstract: 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: Grant
    Filed: May 10, 2004
    Date of Patent: June 5, 2007
    Assignee: Shell Oil Company
    Inventors: Joachim Ansorge, Hendrik Dirkzwager, Joannes Ignatius Geijsel, Abdul Razak Mohamad Ali, Timothy Michael Nisbet, Laurent Alain Michel Fenouil
  • Patent number: 7223374
    Abstract: 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: Grant
    Filed: February 10, 2006
    Date of Patent: May 29, 2007
    Assignee: Institut Francais du Petrole
    Inventors: Lionel Magna, Hélène Olivier-Bourbigou, Lucien Saussine, Virginie Kruger-Tissot
  • Patent number: 7217848
    Abstract: 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: Grant
    Filed: November 29, 2004
    Date of Patent: May 15, 2007
    Assignee: Dow Global Technologies Inc.
    Inventor: Wei-Jun Peng
  • Patent number: 7208635
    Abstract: 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: Grant
    Filed: January 16, 2003
    Date of Patent: April 24, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Richter, Rolf Müller, Roland Krokoszinski
  • Patent number: 7196230
    Abstract: 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: Grant
    Filed: March 4, 2003
    Date of Patent: March 27, 2007
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Wei-Jun Peng, David Robert Bryant
  • Patent number: 7193116
    Abstract: 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: Grant
    Filed: August 7, 2003
    Date of Patent: March 20, 2007
    Assignee: OXENO Olefinchemie GmbH
    Inventors: Oliver Moeller, Klaus-Diether Wiese, Dieter Hess, Cornelia Borgmann, Alfred Kaizik, Dirk Fridag
  • Patent number: 7179947
    Abstract: 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: Grant
    Filed: December 2, 2005
    Date of Patent: February 20, 2007
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Hans-Gerd Lueken, Alfred Kaizik, Stefan Drees, Wilfried Bueschken, Wilhelm Droste
  • Patent number: 7173138
    Abstract: 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: Grant
    Filed: March 28, 2002
    Date of Patent: February 6, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Ahlers, Rocco Paciello, Dieter Vogt, Peter Hofmann
  • Patent number: 7169950
    Abstract: 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: Grant
    Filed: February 13, 2002
    Date of Patent: January 30, 2007
    Assignee: DSM Fine Chemicals Austria NFG GmbH & Co KG
    Inventors: Alexander Sajtos, Engelbert Kloimstein, Curt Zimmermann
  • Patent number: 7145042
    Abstract: 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: Grant
    Filed: September 12, 2003
    Date of Patent: December 5, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Volland, Wolfgang Ahlers, Klaus Ebel, Rocco Paciello, Michael Röper, Thomas Mackewitz, Volker Böhm, Xavier Sava, Oliver Löber, Oliver Bey, Jürgen Stephan, Frank Haese
  • Patent number: 7115387
    Abstract: 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: Grant
    Filed: September 15, 2003
    Date of Patent: October 3, 2006
    Assignee: Council of Scientific & Industrial Research
    Inventors: James Kanagaraj, Gopala Suseela Rajakumar, Sayeed Sadulla
  • Patent number: 7102034
    Abstract: 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: Grant
    Filed: December 8, 2004
    Date of Patent: September 5, 2006
    Assignee: Celanese Chemicals Europe GmbH
    Inventors: 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
  • Patent number: 7102033
    Abstract: 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: Grant
    Filed: April 11, 2002
    Date of Patent: September 5, 2006
    Assignee: DSM IP Assets B.V.
    Inventors: Otto Erik Sielcken, Hubertus Adrianus Smits, Imre Toth
  • Patent number: 7087797
    Abstract: 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: Grant
    Filed: April 11, 2002
    Date of Patent: August 8, 2006
    Assignee: DSM IP Assets B.V.
    Inventors: Otto Erik Sielcken, Hubertus Adrianus Smits, Imre Toth
  • Patent number: 7081553
    Abstract: 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: Grant
    Filed: March 28, 2003
    Date of Patent: July 25, 2006
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Dominic T. Clausi, Eddy T. van Driessche, Ronald D. Garton, James T. Ritchie, Nico A. de Munck
  • Patent number: 7081554
    Abstract: 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: Grant
    Filed: March 28, 2003
    Date of Patent: July 25, 2006
    Assignee: ExxonMobil Chemical Patent Inc.
    Inventors: Ronald D. Garton, James T. Ritchie, Raphael Frans Caers
  • Patent number: 7074955
    Abstract: 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: Grant
    Filed: June 12, 2003
    Date of Patent: July 11, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Hammon, Jochen Meschke, Ulrich Rauh, Klaus Joachim Müller-Engel, Peter Schlemmer, Volker Schliephake
  • Patent number: 7015361
    Abstract: 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: Grant
    Filed: February 13, 2002
    Date of Patent: March 21, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Zehner, Michael Nilles
  • Patent number: 7002044
    Abstract: 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: Grant
    Filed: August 15, 2003
    Date of Patent: February 21, 2006
    Assignee: The University of Connecticut
    Inventors: Can Erkey, Xing Dong
  • Patent number: 6995293
    Abstract: 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: Grant
    Filed: September 3, 2003
    Date of Patent: February 7, 2006
    Assignee: Celanese Chemicals Europe GmbH
    Inventors: Hans Bohnen, Jurgen Herwig, Dietmar Hoff, Peter Wasserscheid, Roy van Hal
  • Patent number: 6995292
    Abstract: 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: Grant
    Filed: September 16, 2002
    Date of Patent: February 7, 2006
    Assignee: Eastman Chemical Company
    Inventors: Ginette Struck Tolleson, Thomas Allen Puckette
  • Patent number: 6982355
    Abstract: 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: Grant
    Filed: August 23, 2004
    Date of Patent: January 3, 2006
    Assignee: Syntroleum Corporation
    Inventor: Armen N. Abazajian
  • Patent number: 6969777
    Abstract: 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: Grant
    Filed: June 27, 2001
    Date of Patent: November 29, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Walz, Willi Schönmann, Rolf Müller, Roland Krokoszinski
  • Patent number: 6946580
    Abstract: 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 strippi
    Type: Grant
    Filed: May 29, 2002
    Date of Patent: September 20, 2005
    Assignee: Davy Process Technology Limited
    Inventors: James Andrew Banister, George Edwin Harrison
  • Patent number: 6921829
    Abstract: The invention generally relates to a method of formylating organic compounds in a microreactor.
    Type: Grant
    Filed: May 28, 2001
    Date of Patent: July 26, 2005
    Assignee: Merck Patent GmbH
    Inventors: Hanns Wurziger, Guido Pieper, Norbert Schwesinger
  • Patent number: 6914162
    Abstract: 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: Grant
    Filed: June 27, 2001
    Date of Patent: July 5, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Richter, Roland Krokoszinski, Rolf Müller, Bernhard Geissler
  • Patent number: 6906225
    Abstract: 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: Grant
    Filed: July 22, 2004
    Date of Patent: June 14, 2005
    Assignee: Eastman Chemical Company
    Inventors: Thomas Allen Puckette, Ginette Struck Tolleson
  • Patent number: 6881867
    Abstract: 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: Grant
    Filed: September 17, 2001
    Date of Patent: April 19, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Ahlers, Dag Wiebelhaus, Rocco Paciello, Michael Bartsch, Robert Baumann, Dieter Vogt, Alison Hewat
  • Patent number: 6849769
    Abstract: 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: Grant
    Filed: September 11, 2001
    Date of Patent: February 1, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Röper, Heinrich-Josef Blankertz, Armin Volker Grenacher, Roland Krokoszinski, Willi Schönmann
  • Patent number: 6822122
    Abstract: 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: Grant
    Filed: December 16, 2002
    Date of Patent: November 23, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Richter, Roland Krokoszinski, Rolf Müller, Michael McAtee
  • Patent number: 6818797
    Abstract: 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: Grant
    Filed: December 16, 2003
    Date of Patent: November 16, 2004
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Willem Wabe Jager
  • Publication number: 20040186323
    Abstract: 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 strippi
    Type: Application
    Filed: April 30, 2004
    Publication date: September 23, 2004
    Inventors: James Andrew Banister, George Edwin Harrison