Hydroformylation By Reacting Ethylenically Unsaturated Compound, Carbon Monoxide And Gaseous Hydrogen Patents (Class 568/429)
  • Patent number: 11342516
    Abstract: An OLED including an organic layer that contains metal complex compounds that are useful as a phosphorescent emitter is disclosed. The metal complex compounds include ligands that incorporate fluorinated side chains and has at least one substituent R selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof, wherein R is directly bonded to an aromatic ring, In the compound, C having an F attached thereto is separated by at least one carbon atom from the aromatic ring.
    Type: Grant
    Filed: September 11, 2020
    Date of Patent: May 24, 2022
    Assignee: UNIVERSAL DISPLAY CORPORATION
    Inventors: Jui-Yi Tsai, Alexey Borisovich Dyatkin, Pierre-Luc T. Boudreault, Walter Yeager, Chuanjun Xia
  • Patent number: 10854826
    Abstract: An OLED including an organic layer that contains metal complex compounds that are useful as a phosphorescent emitter is disclosed. The metal complex compounds include ligands that incorporate fluorinated side chains and has at least one substituent R selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof, wherein R is directly bonded to an aromatic ring. In the compound, C having an F attached thereto is separated by at least one carbon atom from the aromatic ring.
    Type: Grant
    Filed: March 5, 2018
    Date of Patent: December 1, 2020
    Assignee: UNIVERSAL DISPLAY CORPORATION
    Inventors: Jui-Yi Tsai, Alexey Borisovich Dyatkin, Pierre-Luc T. Boudreault, Walter Yeager, Chuanjun Xia
  • Patent number: 10811620
    Abstract: An OLED including an organic layer that contains metal complex compounds that are useful as a phosphorescent emitter is disclosed. The metal complex compounds include ligands that incorporate fluorinated side chains and has at least one substituent R selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof, wherein R is directly bonded to an aromatic ring. In the compound, C having an F attached thereto is separated by at least one carbon atom from the aromatic ring.
    Type: Grant
    Filed: March 5, 2018
    Date of Patent: October 20, 2020
    Assignee: UNIVERSAL DISPLAY CORPORATION
    Inventors: Jui-Yi Tsai, Alexey Borisovich Dyatkin, Pierre-Luc T. Boudreault, Walter Yeager, Chuanjun Xia
  • Patent number: 9799838
    Abstract: Novel ligands for metal complex compounds that are useful as a phosphorescent emitter in organic light emitting devices that incorporate fluorinated side chains in the ligands are disclosed. Such metal complex has at least one substituent R selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof, wherein R is directly bonded to an aromatic ring, In the compound, C having an F attached thereto is separated by at least one carbon atom from the aromatic ring.
    Type: Grant
    Filed: June 9, 2016
    Date of Patent: October 24, 2017
    Assignee: Universal Display Corporation
    Inventors: Pierre-Luc T. Boudreault, Walter Yeager, Chuanjun Xia
  • Patent number: 9694341
    Abstract: The invention relates to a device for the continuous homogeneous catalytic reaction of a liquid with a gas and optionally a further fluid, wherein the device comprises at least one jet loop reactor having an external liquid circuit driven by at least one pump, and wherein the device has at least one membrane separation unit, preferably retaining the homogeneous catalyst, which membrane separation unit is arranged in the external liquid circuit of the jet loop reactor. The object thereof is to reduce the costs of the device. This is achieved by providing an additional apparatus, namely a gas separator, which is arranged in the external liquid circuit of the jet loop reactor and is installed for separating off gas from the external liquid circuit and feeding it back into the jet loop reactor.
    Type: Grant
    Filed: September 23, 2014
    Date of Patent: July 4, 2017
    Assignee: Evonik Degussa GmbH
    Inventors: Robert Franke, Bart Hamers
  • Patent number: 9480978
    Abstract: A functionalized nanomaterial having an average particles size of less than 10 nm comprising an iron oxide nanoparticle core and a bis(diarylphosphinomethyl) dopamine based ligand layer anchored to the iron oxide nanoparticle core is disclosed. In addition, a catalyst composition for use in a variety of chemical transformations wherein the bisphosphine groups of the functionalized nanomaterial chelate a catalytic metal is disclosed. In addition, a method for producing the functionalized nanomaterial and a method for the hydroformylation of olefins to aldehydes employing the functionalized nanomaterial with high conversion percentage and high selectivity are disclosed.
    Type: Grant
    Filed: January 6, 2016
    Date of Patent: November 1, 2016
    Assignee: King Fahd University of Petroleum and Minerals
    Inventors: Mohammed Nasiruzzaman Shaikh, Zain Hassan Yamani
  • Patent number: 9397302
    Abstract: Novel ligands for metal complex compounds that are useful as a phosphorescent emitter in organic light emitting devices that incorporate fluorinated side chains in the ligands are disclosed. Such metal complex has at least one substituent R selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof, wherein R is directly bonded to an aromatic ring, In the compound, C having an F attached thereto is separated by at least one carbon atom from the aromatic ring.
    Type: Grant
    Filed: October 8, 2014
    Date of Patent: July 19, 2016
    Assignee: Universal Display Corporation
    Inventors: Pierre-Luc T. Boudreault, Walter Yeager, Chuanjun Xia
  • Publication number: 20150141699
    Abstract: A process for pyrolyzing a coal feed is described. A coal feed is pyrolyzed into a coal tar stream and a coke stream in a pyrolysis zone. The coal tar stream is separated into at least a pitch stream comprising aromatic hydrocarbons. The pitch stream is reacted in a reaction zone to add at least one functional group to an aromatic ring of the aromatic hydrocarbons in the pitch stream. The functionalized pitch stream is recycled to the pyrolysis zone.
    Type: Application
    Filed: August 26, 2014
    Publication date: May 21, 2015
    Inventors: Paul T. Barger, Maureen L. Bricker, Joseph A. Kocal, Matthew Lippmann, Kurt M. Vanden Bussche
  • Patent number: 8969627
    Abstract: A method for producing a 4,4?-diformyldiphenylalkane represented by the following formula (2), containing formylating a diphenylalkane represented by the following formula (1) with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride, in which the reaction temperature of the formylation is from ?50 to 5° C., from 5 to 30 mol of hydrogen fluoride is used per 1 mol of the diphenylalkane, and from 1.5 to 5 mol of boron trifluoride is used per 1 mol of the diphenylalkane: wherein R represents an alkanediyl group having from 1 to 6 carbon atoms, wherein R represents an alkanediyl group having from 1 to 6 carbon atoms.
    Type: Grant
    Filed: March 29, 2012
    Date of Patent: March 3, 2015
    Assignee: Mitsubishi Gas Chemical Company, Inc
    Inventor: Mitsuharu Kitamura
  • Publication number: 20140135533
    Abstract: Disclosed is a hydroformylation method having improved catalyst stability in a reaction. Advantageously, provided is a hydroformylation method in which a specific ?,?-unsaturated carbonyl compound is incorporated during a hydroformylation reaction to prevent alkyl phosphite decomposed from a phosphite ligand from acting as a catalyst poison, thereby improving a yield of reaction and inhibiting decomposition of ligand and catalyst.
    Type: Application
    Filed: June 4, 2012
    Publication date: May 15, 2014
    Applicant: LG CHEM, LTD.
    Inventors: Dong-Hyun Ko, Sung-Shik Eom, Moo-Ho Hong, O-Hak Kwon, Jae-Hui Choi, Dae-Chul Kim
  • Patent number: 8697918
    Abstract: The present invention relates to 2,6,10-trimethyl-3,5,9-undecatrienyl-1-aldehyde represented by formula (3), and a method for preparing this intermediate. The process route of the present invention is simple, the starting materials are available easily, and the cost is low.
    Type: Grant
    Filed: December 3, 2012
    Date of Patent: April 15, 2014
    Assignees: Shaoxing University, Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory
    Inventors: Runpu Shen, Chunlei Lv, Xiaoyue Jiang, Xuejun Lao, Weidong Ye, Luo Liu, Xiaohua Song, Chunlei Wu
  • Publication number: 20140094627
    Abstract: A method for producing a 4,4?-diformyldiphenylalkane represented by the following formula (2), containing formylating a diphenylalkane represented by the following formula (1) with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride, in which the reaction temperature of the formylation is from ?50 to 5° C., from 5 to 30 mol of hydrogen fluoride is used per 1 mol of the diphenylalkane, and from 1.5 to 5 mol of boron trifluoride is used per 1 mol of the diphenylalkane: wherein R represents an alkanediyl group having from 1 to 6 carbon atoms, wherein R represents an alkanediyl group having from 1 to 6 carbon atoms.
    Type: Application
    Filed: March 29, 2012
    Publication date: April 3, 2014
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY INC
    Inventor: Mitsuharu Kitamura
  • Publication number: 20140024860
    Abstract: The invention relates to a method for hydroformylation of unsaturated compounds such as olefins and alkynes using mixtures of synthesis gas (CO/H2), in which either the unsaturated compounds and a catalyst are heated to a reaction temperature of 60 to 200° C. and the synthesis gas is then added, or the unsaturated compounds and the catalyst are brought into contact with pure CO at normal temperature in a preformation step, then are heated to reaction temperature and on reaching the reaction temperature the CO is replaced by the synthesis gas. The pressure is 1 to 200 bar and the CO:H2 ratio in the synthesis gas is in the range from 1:1 to 50:1. The iridium catalyst used comprises a phosphorus-containing ligand in the iridium:ligand ratio in the range from 1:1 to 1:100. With high catalyst activities and low catalyst use, very high turnover frequencies are achieved.
    Type: Application
    Filed: October 24, 2011
    Publication date: January 23, 2014
    Applicant: Evonik Oxeno GmbH
    Inventors: Robert Franke, Matthias Beller, Ralf Jackstell, Reiko Jennerjahn, Irene Piras
  • Patent number: 8476476
    Abstract: 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: Grant
    Filed: August 19, 2009
    Date of Patent: July 2, 2013
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Eddy T. A. Van Driessche, Ronald D. Garton, Raphael F. Caers
  • Patent number: 8389774
    Abstract: 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: Grant
    Filed: July 9, 2009
    Date of Patent: March 5, 2013
    Assignee: Evonik Oxeno GmbH
    Inventors: Marc Becker, Robert Franke, Wilfried Bueschken, Armin Boerner, Jens Holz
  • Publication number: 20110028746
    Abstract: The present invention relates to a process for preparing aldehydes by reacting an ?,?-unsaturated carboxylic acid or a salt thereof with carbon monoxide and hydrogen in the presence of a catalyst comprising at least one complex of a metal of transition group VIII of the Periodic Table of the Elements with at least one compound of the formula (I), where Pn is pnicogen; W is a divalent bridging group having from 1 to 8 bridge atoms between the flanking bonds; R1 is a functional group capable of forming at least one intermolecular, noncovalent bond with the —X(?O)OH group of the compound of the formula (I); R2, R3 are each in each case optionally substituted alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl or together with the pnicogen atom and together with the groups Y2 and Y3 if present form an optionally fused and optionally substituted 5- to 8-membered heterocycle; a, b and c are each 0 or 1; and Y1,2,3 are each, independently of one another, O, S, NRa or SiRbRc, where Ra,b,c are each H or in each c
    Type: Application
    Filed: March 25, 2009
    Publication date: February 3, 2011
    Applicant: BASF SE
    Inventors: Jens Rudolph, Joachim Schmidt-Leithoff, Rocco Paciello, Bernhard Breit, Thomas Smejkal
  • Publication number: 20110003959
    Abstract: The invention relates to a coordination complex system comprising a ligand having the formula: R1—SO2—NH—P (XR2)2 (1a); or R1—SO2—N?PH (XR2)2 (1b); or R1—SO(OH)?N—P(XR2)2 (1c); wherein X is independently O, S, NH, or a bond; R1 and R2 are independently selected from hydrogen and substituted or unsubstituted alkyl or aryl; wherein at least one equivalent of the ligand is complexed to an equivalent of a metal selected from a transition metal and lanthanide. The invention also relates to the use of said coordination complexes as catalysts in the hydroformylation, hydrogenation, transfer hydrogenation, hydrocyanation, polymerization, isomerization, carbonylation, cross-coupling, metathesis, CH activation, allylic substitution, aldol condensation, or Michael addition.
    Type: Application
    Filed: November 19, 2008
    Publication date: January 6, 2011
    Inventors: Joost Nikolaas Hendrik Reek, Frederic William Patureau, Mark Kuil, Albertus Jacobus Sandee, Jurjen Meeuwissen
  • Patent number: 7858787
    Abstract: A process for converting an olefin having x carbon atoms into an olefin having x+1 carbon atoms wherein the process comprises the steps of: (i) reacting an olefin having x carbon atoms with carbon monoxide and hydrogen in the presence of a hydroformylation catalyst to produce an alcohol having x+1 carbon atoms, and (ii) dehydrating the alcohol produced in step (i) in the presence of a dehydration catalyst to produce an olefin having x+1 carbon atoms characterized in that the hydroformylation catalyst used in step (i) is based on: (a) a source of cobalt, and (b) a ligand which contains phosphorus and nitrogen.
    Type: Grant
    Filed: September 18, 2007
    Date of Patent: December 28, 2010
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Roelof Van Ginkel, Willem Wabe Jager
  • Patent number: 7714179
    Abstract: Processes for preparing a C5 aldehyde and propene are disclosed, the processes comprising: (a) providing a feedstream, the feedstream comprising butane, 1-butene, 2-butene and 1,3-butadiene, the 1,3-butadiene present in the feedstream in an amount up to 1000 ppm; (b) contacting the feedstream with hydrogen and carbon monoxide in the presence of a hydroformylation catalyst to form a 2-butene-rich butane stream and a C5 aldehyde; (c) separating the 2-butene-rich butane stream and the C5 aldehyde; and (d) contacting the 2-butene-rich butane stream with ethene in the presence of a metathesis catalyst to form a propene-containing hydrocarbon stream.
    Type: Grant
    Filed: August 6, 2005
    Date of Patent: May 11, 2010
    Assignee: BASF SE
    Inventors: Marcus Sigl, Markus Schubert, Jürgen Stephan, Rainer Papp, Frank Poplow
  • Patent number: 7531697
    Abstract: (Hetero)aromatic are prepared from halogen-substituted (hetero)aromatic compounds in the presence of a base and a palladium catalyst having a nonpyrophoric monodentate phosphane ligand. The phosphane ligand structure includes two radical groups having a tertiary carbon attached directly to phosphorous and one radical group having a primary carbon attached to the phosphorous.
    Type: Grant
    Filed: March 2, 2006
    Date of Patent: May 12, 2009
    Assignee: Degussa GmbH
    Inventors: Juan Jose Almena Perea, Axel Monsees, Renat Kadyrov, Thomas Riermeier, Kai Rossen, Wolf-Ruediger Krahnert, Matthias Beller, Stefan Klaus, Alexander Zapf
  • 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: 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: 7164045
    Abstract: The present invention is generally directed to electroluminescent Ir(III) compounds with phosphinoalkoxides and phenylpyridines or phenylpyrimidines, and devices that are made with the Ir(III) compounds.
    Type: Grant
    Filed: April 13, 2005
    Date of Patent: January 16, 2007
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Vladimir Grushin, Viacheslav A. Petrov
  • Patent number: 7161043
    Abstract: Process for the carbonylation of optionally substituted ethylenically unsaturated compounds by reaction with carbon monoxide and a coreactant in the presence of a catalyst system. The catalyst system includes (a) a source of Pt group metal cations, (b) a certain bidentate diphosphine composition.
    Type: Grant
    Filed: July 19, 2005
    Date of Patent: January 9, 2007
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 7087795
    Abstract: The invention relates to a hydroformylation method, whereby the homogeneous liquid reactor discharge is first supplied to a gas/liquid separator and then run through an extraction column with a counter-current of synthesis gas and finally fed to an evaporator. The invention is characterised in that the homogeneous liquid mass flow is supplied to the upper section of the extraction column at a temperature above 90° C.
    Type: Grant
    Filed: November 27, 2002
    Date of Patent: August 8, 2006
    Assignee: Celanese Chemicals Europe GmbH
    Inventors: Thomas Krumrey, Kurt Schalapski, Robert Rapier, John Steinbach, Bak Shah, Mark Hewlett
  • Patent number: 7084089
    Abstract: Process for the carbonylation of optionally substituted ethylenically unsaturated compounds by reaction with carbon monoxide and a coreactant in the presence of a catalyst system. The catalyst system includes (a) a source of Pt group metal cations, (b) a certain bidentate diphosphine composition. In addition a method to prepare such a bidentate diphosphine composition is described.
    Type: Grant
    Filed: July 31, 2002
    Date of Patent: August 1, 2006
    Assignee: Shell Oil Company
    Inventors: Michael Rolf Eberhard, Paul Gerard Pringle
  • 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: 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: 7015360
    Abstract: This invention relates to asymmetric hydroformylation (hf) processes in which a prochiral or chiral compound is contacted in the presence of an optically active metal-ligand complex catalyst to produce an optically active aldehyde or product derived from an optically active aldehyde. The invention encompasses novel ligands and catalysts for use in such processes.
    Type: Grant
    Filed: March 28, 2003
    Date of Patent: March 21, 2006
    Assignee: Dow Global Technologies, Inc.
    Inventors: Gregory Todd Whiteker, Jerzy Klosin, Kelli Jo Gardner
  • 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: 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: 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: 6960695
    Abstract: A hydroformylation process comprising reacting a compound having at least one olefinic carbon-to-carbon bond with hydrogen and carbon monoxide in the presence of a cobalt catalyst, the hydroformylation process being carried out in one or more reactors, at least one of which comprises a gas cap region and a liquid-containing region while in use, characterized in that a sulphur-containing additive is present on the inside walls of the gas cap region of the at least one-reactor which comprises a gas cap region and a liquid-containing region. The sulphur-containing additive suppresses the formation of methane during the hydroformylation process.
    Type: Grant
    Filed: October 31, 2003
    Date of Patent: November 1, 2005
    Assignee: Shell Oil Company
    Inventors: Robert Hardy Ellison, Eric Kragtwijk, Frederik Hendrik Van Der Steen
  • Patent number: 6852661
    Abstract: A catalyst comprising at least one complex of a metal of transition group VIII comprising at least one monodentate, bidentate or multidentate phosphinamidite ligand in which the phosphorus atom and the oxygen atom of the phosphinamidite group form part of a 5- to 8-membered heterocycle can be used for the hydroformylation and hydrocyanation of compounds containing at least one ethylenically unsaturated double bond. The phosphinamidite ligand is, for example, represented by the following formulae wherein represents an optionally substituted 5- to 8-membered heterocycle wherein A represents carbon ring members; represents an optionally substituted N-bonded heterocycle wherein (Het) indicates optional ring heteroatoms in addition to the N; and B is a carbon-carbon single bond or a divalent bridging group.
    Type: Grant
    Filed: March 23, 2000
    Date of Patent: February 8, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Ahlers, Heiko Maas, Michael Röper
  • Patent number: 6846960
    Abstract: Disclosed is a process for reducing fluoride content in a process utilizing a fluorophosphite-containing transition metal catalyst.
    Type: Grant
    Filed: September 16, 2002
    Date of Patent: January 25, 2005
    Assignee: Eastman Chemical Company
    Inventors: Ginette Struck Tolleson, Thomas Allen Puckette
  • Patent number: 6806391
    Abstract: Process for the carbonylation of optionally substituted ethylenically unsaturated compounds by reaction with carbon monoxide and a coreactant in the presence of a catalyst system. The catalyst system includes (a) a source of Pt group metal cations, (b) a certain bidentate diphosphine composition.
    Type: Grant
    Filed: July 31, 2002
    Date of Patent: October 19, 2004
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Publication number: 20040199024
    Abstract: The present invention relates to a process for hydroformylating in the presence of a catalyst comprising at least one complex of a metal of transition group VIII with mono-phosphorus compounds which are capable of dimerizing via noncovalent bonds as ligands, to such catalysts and to their use.
    Type: Application
    Filed: March 23, 2004
    Publication date: October 7, 2004
    Inventors: Thomas Mackewitz, Martin Volland, Rocco Paciello, Ansgar Schafer, Bernhard Breit, Wolfgang Seiche
  • Publication number: 20040199023
    Abstract: This invention relates to asymmetric hydroformylation (hf) processes in which a prochiral or chiral compound is contacted in the presence of an optically active metal-ligand complex catalyst to produce an optically active aldehyde or product derived from an optically active aldehyde. The invention encompasses novel ligands and catalysts for use in such processes.
    Type: Application
    Filed: March 28, 2003
    Publication date: October 7, 2004
    Inventors: Gregory Todd Whiteker, Jerzy Klosin, Kelli Jo Gardner
  • Patent number: 6777579
    Abstract: A hydroformylation process is provided that involves reacting a compound having at least one olefinic carbon-to-carbon bond with hydrogen and carbon monoxide in the presence of a cobalt catalyst and a sulfur-containing additive which suppresses the formation of cobalt carbide in the reaction mixture.
    Type: Grant
    Filed: November 14, 2002
    Date of Patent: August 17, 2004
    Assignee: Shell Oil Company
    Inventors: Peter Arnoldy, Robert Hardy Ellison, Herman Pieter Charles Eduard Kuipers, Robert Moene, Frederik Hendrik Van Der Steen
  • Publication number: 20040152923
    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:
    Type: Application
    Filed: December 16, 2003
    Publication date: August 5, 2004
    Inventors: Eit Drent, Willem Wabe Jager
  • Publication number: 20040092754
    Abstract: The invention relates to a method for producing 2- and 2,5-substituted derivatives of 4-(trifluoromethyl)-phenol and 4-(2-trifluoromethyl)-phenyl)-2-tetrahydropyranyl) ether and to novel derivatives. Said method is characterised in that a compound of formula (2) 4-(trifluoromethylphenyl)-2-(tetrahydropyranyl) ether is reacted with an electrophile E-X or a combination of electrophiles E-X and E-Y in the presence of a base, X and Y having the meanings given in the description.
    Type: Application
    Filed: June 30, 2003
    Publication date: May 13, 2004
    Inventors: Bernd Schafer, Herve Geneste
  • Patent number: 6720457
    Abstract: Olefins having from 5 to 24, in particular from 5 to 12, carbon atoms are hydroformylated by reacting an olefin or a mixture of olefins in the presence of an unmodified cobalt catalyst in a single-stage process in a reactor at a temperature of from 100° C. to 220° C. and a pressure of from 100 bar to 400 bar, to obtain an aldehyde, an alcohol or a mixture thereof. An aqueous bottom phase and an organic phase are present in the reactor, the aqueous bottom phase is mixed with the organic phase, and a concentration of the cobalt catalyst, calculated as metallic cobalt, in the aqueous bottom phase is in the range from 0.4 to 1.7% by mass based on the total weight of the aqueous bottom phase. A level of the aqueous bottom phase in the reactor is kept constant during steady-state operation.
    Type: Grant
    Filed: July 24, 2002
    Date of Patent: April 13, 2004
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Stefan Drees, Bernhard Scholz, Alfred Kaizik, Walter Toetsch, Wilfried Bueschken, Martin Trocha
  • Publication number: 20040059161
    Abstract: Disclosed is a process for reducing fluoride content in a process utilizing a fluorophosphite-containing transition metal catalyst.
    Type: Application
    Filed: September 16, 2002
    Publication date: March 25, 2004
    Inventors: Ginette Struck Tolleson, Thomas Allen Puckette
  • Publication number: 20040054211
    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: Application
    Filed: September 16, 2002
    Publication date: March 18, 2004
    Inventors: Ginette Struck Tolleson, Thomas Allen Puckette
  • Patent number: 6700021
    Abstract: The present invention relates to a process for preparing aldehydes by reaction of olefinically unsaturated compounds with carbon monoxide and hydrogen, wherein, during the process, rhodium is added in the form of a reaction product from the reaction of metallic rhodium and/or more than one rhodium compound with rhodium-complexing compounds and with carbon monoxide and hydrogen, the use of said reaction product in catalytic processes and also the preparation of a catalytic composition with addition of said reaction product.
    Type: Grant
    Filed: July 3, 2002
    Date of Patent: March 2, 2004
    Assignee: Celanese Chemicals Europe GmbH
    Inventors: Hans Bohnen, Carl Dieter Frohning, Ernst Wiebus
  • Publication number: 20040024258
    Abstract: Process for the carbonylation of optionally substituted ethylenically unsaturated compounds by reaction with carbon monoxide and a coreactant in the presence of a catalyst system.
    Type: Application
    Filed: July 31, 2002
    Publication date: February 5, 2004
    Inventors: Eit Drent, Michael Rolf Eberhard, Paul Gerard Pringle
  • Patent number: 6680414
    Abstract: The present invention provides a process, which includes: in a homogeneous liquid phase including water, and over a fixed-bed catalyst, continuously hydrogenating at least one hydroformylation product obtained from a hydroformylation of one or more C4-16 olefins to produce at least one output mixture; wherein the fixed-bed catalyst includes at least one element of transition group eight of the Periodic Table of the Elements; wherein the output mixture includes at least one corresponding alcohol and from 0.05 to 10% by weight of water; and wherein in a steady-state operation of the process, from 3 to 50% more hydrogen is fed to the hydrogenation than is consumed by the hydrogenation.
    Type: Grant
    Filed: December 14, 2001
    Date of Patent: January 20, 2004
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Cord Knoop, Bernhard Scholz, Alfred Kaizik, Dietmar Gubisch, Joachim Schuler, Walter Tötsch, Wilfried Büschken
  • Patent number: 6660889
    Abstract: A Fischer-Tropsch reaction is conducted using a synthesis gas (mixture of carbon monoxide and hydrogen) as a raw material to synthesize hydrocarbons containing a large amount of olefin. These hydrocarbons are separated into a light fraction and a heavy fraction by means of a heat exchanger and an oxo process is conducted with respect to the olefin contained in the light fraction with a cobalt catalyst. As a result, an oxygenated fuel containing alcohol, aldehyde, etc. is manufactured. The oxygenated fuel made by such a manufacturing method is excellent in lubricity and oxidation stability, has a high cetane number, and is also capable of suppressing generation of soot when the oxygenated fuel is combusted.
    Type: Grant
    Filed: March 12, 2001
    Date of Patent: December 9, 2003
    Assignees: Toyota Jidosha Kabushiki Kaisha, Genesis Research Institute, Inc.
    Inventors: Kaoru Fujimoto, Noritatsu Tsubaki
  • Publication number: 20030176742
    Abstract: A hydroformylation process is provided that involves reacting a compound having at least one olefinic carbon-to-carbon bond with hydrogen and carbon monoxide in the presence of a cobalt catalyst and a sulfur-containing additive which suppresses the formation of cobalt carbide in the reaction mixture.
    Type: Application
    Filed: November 14, 2002
    Publication date: September 18, 2003
    Inventors: Peter Arnoldy, Robert Hardy Ellison, Herman Pieter Charles Eduard Kuipers, Robert Moene, Frederik Hendrik Van Der Steen
  • Publication number: 20030153791
    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: Application
    Filed: December 16, 2002
    Publication date: August 14, 2003
    Inventors: Wolfgang Richter, Roland Krokoszinski, Rolf Muller, Michael McAtee