Preparing By Carbonylation (e.g., By Hydroformylation, Etc.) Patents (Class 568/909)
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Patent number: 7102038Abstract: A process for making a selectively branched alcohol composition contacting a lower olefin feed comprising linear olefins having at least 3 carbon atoms and a concentration of phosphorous-containing compounds with a sorbent comprising a metal or metal oxide on a support, thereby substantially reducing the concentration of phosphorous-containing compounds and producing a purified lower olefin feed. The purified lower olefin feed is skeletally isomerized and then treated to selectively hydrogenate dienes before hydroformylation to produce selectively branched alcohols.Type: GrantFiled: August 9, 2002Date of Patent: September 5, 2006Assignee: Shell Oil CompanyInventors: Brendan Dermont Murray, Paul Benjerman Himelfarb, Zaida Diaz, David Michael Singleton
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Patent number: 7057081Abstract: Methods are disclosed for converting propane and higher alkanes to their corresponding alcohols through a multi-step process with olefin as an intermediate. Methods are also disclosed for facilitating the transportation, purification or other treatment of propylene and higher olefins using a chemical conversion to the corresponding alcohol and reconversion to olefin. Methods are also disclosed for converting propane and higher alkanes to olefins using the corresponding alcohol as a temporary intermediate to minimize purification, transportation and/or other treatment costs.Type: GrantFiled: May 9, 2003Date of Patent: June 6, 2006Assignee: ConocoPhillips CompanyInventors: Joe D. Allison, Steven R. McDonald
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Patent number: 6963014Abstract: A process for preparing a C13-alcohol mixture comprises a) bringing a butene-containing C4-hydrocarbon stream containing less than 5% by weight, based on the butene fraction, of isobutene into contact with a nickel-containing heterogeneous catalyst at elevated temperature, b) isolating a C12-olefin fraction from the reaction mixture, c) hydroformylating the C12-olefin fraction by reaction with carbon monoxide and hydrogen in the presence of a cobalt catalyst and d) hydrogenating the product from c). The alcohol mixture is suitable for preparing surfactants by alkoxylation, glycosidation, sulfation, phosphation, alkoxylation and subsequent sulfation or alkoxylation and subsequent phosphation.Type: GrantFiled: November 17, 2000Date of Patent: November 8, 2005Assignee: BASF AktiengesellschaftInventors: Edgar Zeller, Marc Walter, Wolfgang Richter, Klaus Diehl, Michael Röper, Jürgen Tropsch
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Patent number: 6906230Abstract: The invention describes a process for the preparation of surfactant alcohols and surfactant alcohol ethers which are, inter alia, highly suitable as surfactants or for the preparation of surfactants. The process, starting from olefin mixtures having a defined minimum content of linear hexenes, gives mixtures having a predominant fraction of branched dodecenes, which are subsequently derivatized to give surfactant alcohols and then optionally alkoxylated. The surfactant alcohol mixture obtained in the process has a degree of branching of from 2.0 to 3.0 and in particular exhibits advantageous properties as regards ecotoxicity and biodegradability. A description is also given of the use of the surfactant alcohols and surfactant alcohol ethers as surfactants by glycosidation or polyglycosidation, sulfation or phosphation.Type: GrantFiled: March 17, 2000Date of Patent: June 14, 2005Assignee: BASF AktiengesellschaftInventors: Heiko Maas, Michael Röper, Marc Walter, Ralf Schulz, Jürgen Tropsch, Hans-Ulrich Jäger
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Publication number: 20040199023Abstract: 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: ApplicationFiled: March 28, 2003Publication date: October 7, 2004Inventors: Gregory Todd Whiteker, Jerzy Klosin, Kelli Jo Gardner
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Publication number: 20040152928Abstract: The invention pertains to a hydroformylation process for the conversion of an ethylenically unsaturated compound to an alcohol comprising a first step of reacting at an elevated temperature in a reactor the ethylenically unsaturated compound, carbon monoxide, hydrogen, and a phosphine-containing cobalt hydroformylation catalyst, which are dissolved in a solvent, followed by a second step of separating a mixture comprising the alcohol and heavy ends from a solution comprising the catalyst and the solvent, followed by a third step of recycling the solution to the reactor.Type: ApplicationFiled: December 16, 2003Publication date: August 5, 2004Inventors: Eit Drent, Jacoba Catherina Lucia Johanna Suykerbuyk
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Publication number: 20040152923Abstract: 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: ApplicationFiled: December 16, 2003Publication date: August 5, 2004Inventors: Eit Drent, Willem Wabe Jager
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Patent number: 6762332Abstract: A process for the preparation of an alcohol from an olefin wherein the olefin is reacted with syngas in the presence of a catalyst system having a homogeneous hydroformylation catalyst and a heterogeneous catalyst having copper on a support.Type: GrantFiled: November 22, 2002Date of Patent: July 13, 2004Assignee: Shell Oil CompanyInventor: Jean-Paul Lange
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Patent number: 6756411Abstract: A process for producing oxygenated products from an olefin-rich feedstock comprise reacting, in a hydroformylation stage, a Fischer-Tropsch derived olefinic product comprising linear and methyl branched olefins, with carbon monoxide and hydrogen in the presence of a catalytically effective quantity of a hydroforhylation catalyst and under hydroformylation reaction conditions, to produce oxygenated products comprising linear and methyl branched aldehydes and/or alcohols. The Fischer-Tropsch derived olefinic product is that obtained by subjecting a synthesis gas comprising carbon monoxide (CO) and hydrogen (H2) to Fischer-Tropsch reaction conditions in the presence of a Fischer-Tropsch catalyst.Type: GrantFiled: October 28, 2002Date of Patent: June 29, 2004Assignee: Sasol Technology (Proprietary) LimitedInventors: Mark Justin Betts, Mark Eberhard Dry, Arie Geertsema, Gerhardus Johannes Hendricus Rall
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Patent number: 6737553Abstract: The invention describes a process for the preparation of novel surfactant alcohols and surfactant alcohol ethers by derivatization of olefins having from about 10 to 20 carbon atoms or of mixtures of such olefins to give alkanols, and optional subsequent alkoxylation, which comprises subjecting a C4-olefin mixture to metathesis, dimerizing the resulting olefins, and then derivatizing them to give surfactant alcohols, and optionally alkoxylating said alcohols. The olefin mixture obtained in the dimerization has a high proportion of branched components and less than 10% by weight of compounds which contain a vinylidene group. The invention further describes the use of the surfactant alcohols and surfactant alcohol ethers to give surfactants by glycosylation or polyglycosylation, sulfation or phosphation.Type: GrantFiled: June 18, 2001Date of Patent: May 18, 2004Assignee: BASF AktiengesellschaftInventors: Heiko Maas, Michael Röper, Marc Walter, Ralf Schulz, Jürgen Tropsch, Hans-Ulrich Jäger, Peter Schwab, Michael Schulz
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Patent number: 6723886Abstract: An apparatus and method is disclosed for producing alcohols, particularly methanol, according to an alcohol synthesis process. The apparatus comprises a catalytic distillation reactor where reactants are fed into the catalytic distillation reactor to undergo catalytic reaction to form methanol. Methanol production beyond the thermodynamic limit is achieved in the apparatus through use of multiple distillation stages, preferably at least three.Type: GrantFiled: May 16, 2002Date of Patent: April 20, 2004Assignee: ConocoPhillips CompanyInventors: Joe D. Allison, Harold A. Wright, Todd H. Harkins, Doug S. Jack
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Patent number: 6717018Abstract: A process for producing oxygenated products from an olefinic feedstock, which process includes reacting, in a hydroformylation reaction stage, an olefin feedstock with carbon monoxide and hydrogen at elevated temperature and superatmospheric pressure in the presence of a hydroformylation catalyst. The hydroformylation catalyst comprises a mixture of a metal, M, where M is cobalt (Co), rhodium (Rh), ruthenium (Ru) or palladium (Pd); carbon monoxide; and a bicyclic tertiary phosphine having a ligating phosphorus atom. The ligating phosphorus atom is neither in a bridgehead position nor a member of a bridge linkage. The process produces oxygenated products comprising aldehydes and/or alcohols.Type: GrantFiled: February 5, 2003Date of Patent: April 6, 2004Assignee: Sasol Technology (Proprietary) LimitedInventors: Jan Petrus Steynberg, Khedaren Govender, Petrus Johannes Steynberg
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Patent number: 6660892Abstract: This invention is a process for synthesizing aliphatic 1,3-diols in one step by hydroformylation and hydrogenation of oxirane, carbon monoxide, and hydrogen employing a catalyst comprising a cobalt carbonyl compound and a cocatalyst metal compound ligated with a ligand in a ligand to cocatalyst metal atom molar ratio in the range of 0.2:1.0 to 0.6:1.0, optionally in the presence of a promoter, where recovery of product is preferably accomplished via water extraction of a diol rich phase from the bulk reaction mixture. The process modifications can, particularly in combination, be beneficial with respect to product recovery, catalyst recycle, and overall economics of a one-step process for producing aliphatic 1,3-diols.Type: GrantFiled: February 7, 2003Date of Patent: December 9, 2003Assignee: Shell Oil CompanyInventors: Joseph Broun Powell, Paul Richard Weider, John Frederick Knifton, Kevin Dale Allen, Lynn Henry Slaugh, Juan Pedro Arhancet
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Patent number: 6660889Abstract: 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: GrantFiled: March 12, 2001Date of Patent: December 9, 2003Assignees: Toyota Jidosha Kabushiki Kaisha, Genesis Research Institute, Inc.Inventors: Kaoru Fujimoto, Noritatsu Tsubaki
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Patent number: 6657092Abstract: Process for the preparation of a highly linear alcohol composition is provided comprising the steps of: (a) reacting carbon monoxide with hydrogen under Fischer-Tropsch reaction conditions in the presence of a Fischer-Tropsch catalyst comprising cobalt; (b) separating from the product of step (a) at least one hydrocarbon fraction comprising between 10 and 50% by weight of olefins containing 6 or more carbon atoms; (c) contacting one or more of the hydrocarbon fractions obtained in step (b) with carbon monoxide and hydrogen under hydroformylation conditions in the presence of a hydroformylation catalyst based on a source of cobalt and one or more alkyl phosphines; and (d) recovering the alcohol composition.Type: GrantFiled: June 11, 2002Date of Patent: December 2, 2003Assignee: Shell Oil CompanyInventors: Hendrik Dirkzwager, Laurent Alain Fenouil, Joannes Ignatius Geijsel, Arend Hoek, Frederik Hendrik Van Der Steen
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Patent number: 6653514Abstract: The invention pertains to a process of removing phosphorous-containing impurities and preferably also dienes, from an olefin stream using a sorbent selected from the group consisting of an acidic ion exchange resin, an acidic zeolite, an acidic alumina, a neutral alumina, and an activated carbon. The olefin stream preferably comprises primarily olefins having at least 6 carbon atoms.Type: GrantFiled: May 8, 2000Date of Patent: November 25, 2003Assignee: Shell Oil CompanyInventors: Brendan Dermot Murray, David Michael Singleton, Zaida Diaz
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Publication number: 20030195378Abstract: In a process for the hydroformylation of ethylenically unsaturated compounds, at least one complex of a metal of transition group VIII. with at least one phosphorus-, arsenic- or antimony-containing compound as ligand is used as hydroformylation catalyst, where the compound used as ligand in each case comprises two groups which comprise a P, As or Sb atom and at least two further hetero atoms and are bound to a xanthene-like molecular framework. New compounds of this type and catalysts which comprise at least one complex of a metal of transition group VIII. with at least one such compound as ligand are also provided.Type: ApplicationFiled: March 11, 2003Publication date: October 16, 2003Inventors: Wolfgang Ahlers, Dag Wiebelhaus, Rocco Paciello, Michael Bartsch, Robert Baumann, Dieter Vogt, Alison Hewat
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Publication number: 20030195368Abstract: The invention relates to the bisphosphites of the general formula(I), wherein R1, R2, R3, $4 R5 R6 represent H, an aliphatic, alicyclic, aliphatic-alicyclic, heterocyclic, aliphatic-heterocyclic, aromatic, aliphatic-aromatic hydrocarbon group with 1 to 50 carbon atoms, F, Cl, Br, I, —OR7, —COR7, —CO2R7, —CO2M, —SR7, —SO2R7, —SOR7, —SO3R7, —SO3M, —SO2NR7R8, NR7R8, N═CR7R8, NH2, wherein R1 to R6 are the same or different and can be covalently linked with each other, R7, R8 represent H, a substituted or unsubstituted, aliphatic or aromatic hydrocarbon group with 1 to 25 carbon atoms, which are the same or different, M represents an alkali metal, alkaline earth metal, ammonium, phosphonium ion; Q represents a bivalent, aliphatic alicyclic, aliphatic-alicyclic, heterocyclic, aromatic, aliphatic-aromatic hydrocarbon group with 1 to 50 carbons atoms, W, X represent aliphatic, alicyclic, aliphatic-alicyclic, heterocyclic, aliphatic-heterocyclic, aromatiType: ApplicationFiled: April 24, 2003Publication date: October 16, 2003Inventors: Dirk Rottger, Renat Kadyrov, Armin Borner, Detlef Selent, Dieter Hess
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Publication number: 20030176743Abstract: Olefins having from 2 to 8 carbon atoms are hydroformylated in a process in which (i) an olefin-containing feed in which a proportion of a saturated hydrocarbon having from 2 to 8 carbon atoms is present and also carbon monoxide and hydrogen are fed into a reaction zone and reacted in the presence of a hydroformylation catalyst, (ii) a stream consisting essentially of unreacted olefin and saturated hydrocarbon is separated off from the output from the reaction zone, (iii) the stream is separated into an olefin-enriched fraction and an olefin-depleted fraction by rectification, and (iv) at least part of the olefin-enriched fraction is recirculated to the reaction zone.Type: ApplicationFiled: December 26, 2002Publication date: September 18, 2003Inventors: Helmut Walz, Willi Schnmann, Rolf Mller, Roland Krokoszinski
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Publication number: 20030176742Abstract: 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: ApplicationFiled: November 14, 2002Publication date: September 18, 2003Inventors: Peter Arnoldy, Robert Hardy Ellison, Herman Pieter Charles Eduard Kuipers, Robert Moene, Frederik Hendrik Van Der Steen
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Publication number: 20030158446Abstract: A process for producing oxygenated products from an olefinic feedstock, which process includes reacting, in a hydroformylation reaction stage, an olefin feedstock with carbon monoxide and hydrogen at elevated temperature and superatmospheric pressure in the presence of a hydroformylation catalyst. The hydroformylation catalyst comprises a mixture of a metal, M, where M is cobalt (Co), rhodium (Rh), ruthenium (Ru) or palladium (Pd); carbon monoxide; and a bicyclic tertiary phosphine having a ligating phosphorus atom. The ligating phosphorus atom is neither in a bridgehead position nor a member of a bridge linkage. The process produces oxygenated products comprising aldehydes and/or alcohols.Type: ApplicationFiled: February 5, 2003Publication date: August 21, 2003Applicant: SASOL TECHNOLOGY (PROPRIETARY) LIMITEDInventors: Jan Petrus Steynberg, Khedaren Govender, Petrus Johannes Steynberg
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Publication number: 20030153791Abstract: 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: ApplicationFiled: December 16, 2002Publication date: August 14, 2003Inventors: Wolfgang Richter, Roland Krokoszinski, Rolf Muller, Michael McAtee
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Publication number: 20030144559Abstract: A process for the catalytic hydroformylation of olefins having from 3 to 24 carbon atoms, where the catalyst used comprises a metal of transition group 8 of the Periodic Table in the presence of a ligand represented by formula I: 1Type: ApplicationFiled: November 13, 2002Publication date: July 31, 2003Applicant: Degussa AGInventors: Dieter Hess, Dirk Roettger, Detlef Selent, Armin Boerner
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Publication number: 20030139630Abstract: The present invention relates to a process for the formylation of organic compounds.Type: ApplicationFiled: November 25, 2002Publication date: July 24, 2003Inventors: Hanns Wurziger, Guido Pieper, Norbert Schwesinger
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Publication number: 20030120118Abstract: A process for producing oxygenated products from an olefin-rich feedstock comprise reacting, in a hydroformylation stage, a Fischer-Tropsch derived olefinic product comprising linear and methyl branched olefins, with carbon monoxide and hydrogen in the presence of a catalytically effective quantity of a hydroforhylation catalyst and under hydroformylation reaction conditions, to produce oxygenated products comprising linear and methyl branched aldehydes and/or alcohols. The Fischer-Tropsch derived olefinic product is that obtained by subjecting a synthesis gas comprising carbon monoxide (CO) and hydrogen (H2) to Fischer-Tropsch reaction conditions in the presence of a Fischer-Tropsch catalyst.Type: ApplicationFiled: October 28, 2002Publication date: June 26, 2003Applicant: SASOL TECHNOLOGY (PROPRIETARY) LIMITEDInventors: Mark Justin Betts, Mark Eberhard Dry, Arie Geertsema, Gerhardus Johannes Hendricus Rall
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Patent number: 6573414Abstract: A process for preparing C9-alcohols comprises a) providing a C4-hydrocarbon stream comprising butene and butane; b) subjecting the C4-hydrocarbon stream to oligomerization over an olefin oligomerization catalyst and fractionating the resulting reaction mixture to give an octene-containing stream and a butene-depleted C4-hydrocarbon stream; c) subjecting the butene-depleted C4-hydrocarbon stream to steam reforming or partial oxidation to give carbon monoxide and hydrogen; d) hydroformylating the octene-containing stream by means of carbon monoxide and hydrogen in the presence of a hydroformylation catalyst to form C9-aldehydes, where the carbon monoxide used and/or the hydrogen used originate at least in part from step c); and e) catalytically hydrogenating the C9-aldehydes by means of hydrogen.Type: GrantFiled: July 18, 2002Date of Patent: June 3, 2003Assignee: BASF AktiengesellschaftInventors: Michael Richard McAtee, Rocco Paciello, Michael-Dieter Ulbrich
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Patent number: 6566564Abstract: Process for the isomerization of precursor allyl alcohols to product allyl alcohols in the presence of tungsten oxo(VI) complexes comprising additional nitrogen-containing ligands at temperatures of from 50 to 300° C., wherein, in the catalyst, as well as the nitrogen bases known as additional nitrogen-containing ligands, or instead of these nitrogen bases, aminoalcohols such as triethanolamine, diethanolamine, monoethanolamine, tripropanolamine, dipropanolamine, 3-amino-1-propanol, 1-amino-2-propanol, 2-amino-1-propanol, butyldiethanolamine, methyldiisopropanolamine, N,N′-bis(2-hydroxybenzyl)-1,2-diaminoethane or N-(2-hydroxybenzyl)amine are present as additional nitrogen-containing ligands. The process is particularly suitable for the preparation of tertiary product allyl alcohols, such as linalool, by isomerizing primary or secondary allyl alcohols, such as geraniol and nerol.Type: GrantFiled: May 23, 2002Date of Patent: May 20, 2003Assignee: BASF AktiengesellschaftInventors: Klaus Ebel, Frank Stock
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Patent number: 6566565Abstract: The invention pertains to a process of making selectively branched alcohol compositions by oligomerizing a lower olefin feed. The lower olefin feed preferably comprises linear olefins having at least three carbon atoms.Type: GrantFiled: May 8, 2000Date of Patent: May 20, 2003Assignee: Shell Oil CompanyInventors: Brendan Dermot Murray, David Michael Singleton
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Patent number: 6566566Abstract: The invention describes a process for the preparation of surfactant alcohols and surfactant alcohol ethers which are, inter alia, highly suitable as surfactants or for the preparation of surfactants. The process, starting from olefin mixtures which comprise less than 30% by weight of linear hexene isomers and utilizing a catalyst which contains nickel, prepares olefin mixtures having a predominant fraction of branched dodecenes, which are subsequently derivatized to give surfactant alcohols and then optionally alkoxylated. The invention further relates to the use of the surfactant alcohols and surfactant alcohol ethers for the preparation of surfactants by glycosidation or polyglycosidation, sulfation or phosphation.Type: GrantFiled: September 10, 2001Date of Patent: May 20, 2003Assignee: BASF AktiengesellschaftInventors: Heiko Maas, Michael Röper, Marc Walter, Ralf Schulz, Jürgen Tropsch, Hans-Ulrich Jäger
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Patent number: 6555716Abstract: Aldehydes are prepared in a hydroformylation apparatus by the multiphase hydroformylation reaction of one or more olefins with hydrogen and carbon monoxide, where the continuous phase contains a solvent mixture and the hydroformylation catalyst is present in the continuous phase, at least one olefin is present in the dispersed phase, and the loading factor of the tube reactor is greater than or equal to 0.8.Type: GrantFiled: November 30, 2000Date of Patent: April 29, 2003Assignee: Oxeno Olefinchemie GmbHInventors: Guido Protzmann, Klaus-Diether Wiese, Wilfried Büschken, Dirk Röttger
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Publication number: 20030073750Abstract: Process for the preparation of a highly linear alcohol composition is provided comprising the steps of:Type: ApplicationFiled: June 11, 2002Publication date: April 17, 2003Inventors: Hendrik Dirkzwager, Laurent Alain Fenouil, Joannes Ignatius Geijsel, Arend Hoek, Frederik Hendrik Van Der Steen
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Patent number: 6521783Abstract: This invention relates in part to a processes for the conversion of a feedstock stream comprising carbon monoxide and hydrogen to a product stream comprising at least one of an ester, acid, acid anhydride and mixtures thereof. This invention also relates in part to processes for converting an alcohol and/or ether feedstock to oxygenated products, e.g., esters, acids, acid anhydrides and mixtures thereof. The processes and catalysts are especially suitable for the production of acetic acid and methyl acetate from a synthesis gas feedstock or from an alcohol and/or ether feedstock.Type: GrantFiled: July 10, 2000Date of Patent: February 18, 2003Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Richard William Wegman, David McNeill Somerville, Barry Brent Fish, Raymond Edwin Rooks, Chinsoo Stephen Lee, Paul Frank Bryan, William J. Bartley, David Michael Anthony Minahan, Fungau Ho
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Publication number: 20030022947Abstract: A process for preparing C9-alcohols comprises a) providing a C4-hydrocarbon stream comprising butene and butane; b) subjecting the C4-hydrocarbon stream to oligomerization over an olefin oligomerization catalyst and fractionating the resulting reaction mixture to give an octene-containing stream and a butene-depleted C4-hydrocarbon stream; c) subjecting the butene-depleted C4-hydrocarbon stream to steam reforming or partial oxidation to give carbon monoxide and hydrogen; d) hydroformylating the octene-containing stream by means of carbon monoxide and hydrogen in the presence of a hydroformylation catalyst to form C9-aldehydes, where the carbon monoxide used and/or the hydrogen used originate at least in part from step c); and e) catalytically hydrogenating the C9-aldehydes by means of hydrogen.Type: ApplicationFiled: July 18, 2002Publication date: January 30, 2003Inventors: Michael Richard McAtee, Rocco Paciello, Michael-Dieter Ulbrich
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Patent number: 6492568Abstract: The invention pertains to a process of removing phosphorus-containing impurities from an olefin stream using a sorbent comprising a metal. The olefin stream preferably comprises primarily olefins having at least 6 carbon atoms.Type: GrantFiled: May 8, 2000Date of Patent: December 10, 2002Assignee: Shell Oil CompanyInventors: Brendan Dermot Murray, Zaida Diaz, Glenn Charles Komplin
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Patent number: 6482992Abstract: Olefins are hydroformylated to give alcohols and/or aldehydes in a plurality of hydroformylation stages, each of which comprises: a) hydroformylating olefins having a carbon atom content of 6 to 24 carbon atoms in the presence of a cobalt- or rhodium catalyst in a reactor to the point of conversion of olefin reactant to product of 20 to 98%; b) removing the catalyst from the resulting liquid discharged from the reactor; c) separating the resulting liquid hydroformylation mixture into a low-boiler fraction comprising olefins and paraffins, and a bottoms fraction comprising aldehydes and/or alcohols; and d) reacting the olefins present in the low-boiler fraction in subsequent process stages comprising steps a, b and c and combining the bottoms fractions of process steps c) of all process stages.Type: GrantFiled: July 16, 2001Date of Patent: November 19, 2002Assignee: OXENO Olefinchemie GmbHInventors: Bernhard Scholz, Franz Nierlich, Alfred Kaizik, Dieter Hess, Wilfried Bueschken, Klaus-Diether Wiese, Dirk Roettger, Guido Protzmann
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Publication number: 20020161251Abstract: The invention provides a process for an improved oxirane hydroformylation catalyst, the improved oxirane hydroformylation catalyst, and a one step process for preparing a 1,3-diol in the presence of such a catalyst.Type: ApplicationFiled: April 23, 2002Publication date: October 31, 2002Inventors: John Frederick Knifton, Lynn Henry Slaugh, Paul Richard Weider, Talmadge Gail James, Joseph Broun Powell, Kevin Dale Allen, Timothy Scott Williams
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Publication number: 20020115892Abstract: In a process for the hydroformylation of ethylenically unsaturated compounds, at least one complex or compound of a metal of transition group VIII with at least one bidentate phosphine ligand is used as hydroformylation catalyst and at least one of the reaction steps following the hydroformylation reaction is carried out essentially in the absence of carbon monoxide and hydrogen and in the presence of at least one monodentate phosphine ligand.Type: ApplicationFiled: February 19, 2002Publication date: August 22, 2002Inventor: Thomas MacKewitz
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Patent number: 6410799Abstract: In a process for hydroformylation of olefinically unsaturated compounds using a catalyst based on cobalt and/or rhodium co-ordinated by at least one ligand selected from the group formed by nitrogen-containing or phosphorus-containing ligands used in a non-aqueous ionic solvent, which catalyst is liquid at a temperature of less than 90° C., in which the aldehydes formed are not or are only slightly soluble and which comprises at least one quaternary ammonium and/or phosphonium cation Q+ and at least one anion A−, the improvement of the invention consists in that in the cobalt and/or rhodium complex, the ligand also carries an ionic function (Q′)+(A′)− where Q and Q′ and/or A and A′ are chemically identical.Type: GrantFiled: August 23, 2001Date of Patent: June 25, 2002Assignee: Institut Francais du PetroleInventors: Frédéric Favre, Dominique Commereuc, Hélène Olivier-Bourbigou, Lucien Saussine
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Patent number: 6369283Abstract: This invention relates in part to processes for producing one or more substituted or unsubstituted unsaturated alcohols which comprise reacting one or more substituted or unsubstituted alkadienes with carbon monoxide and hydrogen in the presence of a metal-ligand complex catalyst and a promoter and optionally free ligand to produce said one or more substituted or unsubstituted unsaturated alcohols. The substituted and unsubstituted unsaturated alcohols produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted unsaturated alcohols as principal product(s) of reaction.Type: GrantFiled: November 2, 2000Date of Patent: April 9, 2002Assignee: Union Carbide Chemicals & Plastics Technology Corp.Inventors: Anil Sakharam Guram, John Robert Briggs, Kurt Damar Olson, Thomas Carl Eisenschmid, Daine Lee Packett, Erik Bruce Tjaden
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Patent number: 6365783Abstract: Provided is a process for producing alcohols or aldehydes by reacting monoolefins with carbon monoxide and hydrogen with less formation of by-products. The process comprises the step of reacting a monoolefin with carbon monoxide and hydrogen in the presence of a cobalt carbonyl catalyst until the conversion of monoolefin reaches 50-90% (the first reaction step), the step of separating unreacted monoolefin from the reaction mixture obtained in the first reaction step (the step of separation of unreacted monoolefin) and the step of reacting the separated unreacted monoolefin with carbon monoxide and hydrogen in the presence of a cobalt carbonyl catalyst (the second reaction step), wherein at least one of the first reaction step and the second reaction step is carried out in the presence of water.Type: GrantFiled: May 25, 2000Date of Patent: April 2, 2002Assignee: Kyowa Yuka Co., Ltd.Inventors: Yorozu Yokomori, Tsukasa Hayashi, Toshiaki Ogata, Junichi Yamada, Seiji Saito
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Patent number: 6365782Abstract: A method of producing tricyclodecane dicarbaldehyde and/or pentacyclopentadecane dicarbaldehyde by the hydroformylation of dicyclopentadiene and/or tricyclopentadiene. The tricyclodecane dicarbaldehyde and/or pentacyclopentadecane dicarbaldehyde in the hydroformylation product liquid are extracted with an extraction solvent comprising a polyhydric alcohol having 2 to 6 carbon atoms. With such extraction, the tricyclodecane dicarbaldehyde and/or pentacyclopentadecane dicarbaldehyde transfer into the extraction solvent while retaining the catalyst components in the hydroformylation solvent. The controlled extraction atmosphere with an oxygen concentration of 1000 ppm or lower prevents the rhodium compound from transferring into the extraction solvent, thereby avoiding the loss of expensive rhodium.Type: GrantFiled: July 3, 2000Date of Patent: April 2, 2002Assignee: Mitsbushi Gas Chemical Company, Inc.Inventors: Kenichi Nakamura, Kazuhiro Yamada, Takashi Fujii, Takashi Motoi
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Patent number: 6359179Abstract: A process for the direct carbonylation of saturated hydrocarbons has been developed. The process involves contacting the saturated hydrocarbons, which contain at least one primary, secondary or tertiary carbon atom, with carbon monoxide in the presence of a solid strong acid catalyst to produce an oxygenated saturated hydrocarbon. In a specific embodiment isobutane is reacted with carbon monoxide using sulfated zirconia as the catalyst to produce methylisopropyl ketone. The oxygenated hydrocarbon can subsequently be hydrogenated to give a reduced oxygenated saturated hydrocarbon. The hydrogenation can also be done simultaneously with the carbonylation, i.e., reductive carbonylation.Type: GrantFiled: December 22, 1999Date of Patent: March 19, 2002Assignee: UOP LLCInventors: Laszlo T. Nemeth, Jeffrey C. Bricker, Jules Rabo, Ralph D. Gillespie
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Publication number: 20020028976Abstract: Alpha-olefins are dimerized to form branched-chain feedstocks for detersive surfactants.Type: ApplicationFiled: September 6, 2001Publication date: March 7, 2002Inventor: Daniel Stedman Connor
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Publication number: 20020028974Abstract: Olefins are hydroformylated to give alcohols and/or aldehydes in a plurality of hydroformylation stages, each of which comprises:Type: ApplicationFiled: July 16, 2001Publication date: March 7, 2002Applicant: OXENO Olefinchemie GmbHInventors: Bernhard Scholz, Franz Nierlich, Alfred Kaizik, Dieter Hess, Wilfried Bueschken, Klaus-Diether Wiese, Dirk Roettger, Guido Protzmann
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Publication number: 20020019574Abstract: A process for producing alcohols, to obtain a straight-chain alcohol having a carbon number of n (where n=3 to 6), a branched chain alcohol having a carbon number of n (where n=3 to 6) and a branched chain alcohol having a carbon number of 2n (where n=3 to 6) from a mixed aldehyde comprising a straight-chain aldehyde having a carbon number of n (where n=3 to 6) and a branched chain aldehyde having a carbon number of n (where n=3 to 6) in an optional proportion, which comprises supplying the mixed aldehyde to a distillation column, withdrawing from the bottom of the column an aldehyde rich in the straight-chain aldehyde, dimerizing the straight-chain aldehyde, followed by hydrogenation to obtain the branched chain alcohol having a carbon number of 2n, while obtaining, as a fraction from the top of the column, an aldehyde rich in the branched chain aldehyde and having a straight-chain aldehyde concentration in the fraction of at least 30 wt %, subjecting the fraction to hydrogType: ApplicationFiled: May 20, 1999Publication date: February 14, 2002Inventors: AKIO UEDA, ATSUHIRO ADACHI
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Publication number: 20020007096Abstract: This invention relates to processes for producing substituted or unsubstituted alkenols. The process subjects an alkadiene to reductive hydroformylation to selectively produce at least one substituted or unsubstituted alkenols. The process is particularly useful in producing pentenols from butadiene. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted alkenols as principal reaction products.Type: ApplicationFiled: April 15, 1997Publication date: January 17, 2002Inventors: DIANE LEE PACKETT, JOHN ROBERT BRIGGS, DAVID ROBERT BRYANT, AILENE GARDNER PHILLIPS, DAVID JAMES SCHRECK, ANIL SAKHARAM GURAM, KURT DAMAR OLSON, THOMAS CARL EISENSCHMID
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Patent number: 6331656Abstract: In a process for the hydroformylation of olefins having from 12 to 100 carbon atoms in the presence of a cobalt carbonyl catalyst at pressures of from 100 to 400 bar and at from 100 to 200° C., depressurization and recovery of the cobalt catalyst by extraction with an aqueous acid solution in the presence of atmospheric oxygen, (a) the extraction is carried out in the presence of a polymeric emulsion breaker selected from the group consisting of alkoxylated compounds containing amino, imino or OH groups, and (b) to achieve complete phase separation in the organic phase still containing small amounts of aqueous phase, the formation of relatively large droplets of the dispersed aqueous phase is effected in a coalescence stage.Type: GrantFiled: March 4, 1999Date of Patent: December 18, 2001Assignee: BASF AktiengesellschaftInventors: Heinrich-Josef Blankertz, Armin Volker Grenacher, Friedrich Sauer, Harald Schwahn, Willi Schönmann, Michael Röper
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Patent number: 6331657Abstract: A process for preparing higher oxo alcohols from mixtures of isomeric olefins having from 5 to 24 carbon atoms by two-stage hydroformylation in the presence of a cobalt catalyst or rhodium catalyst at elevated temperature and at elevated pressure, which comprises selectively hydrogenating the first hydroformylation stage reaction mixture, separating the hydrogenation mixture in a distillation into crude alcohol and low-boilers predominantly consisting of olefins, passing these low-boilers to the second hydroformylation stage, again selectively hydrogenating the second hydroformylation stage reaction mixture, separating the hydrogenation mixture in one distillation into crude alcohol and low-boilers, working up the crude alcohol by distillation to pure alcohol and taking off at least some of the low-boilers to discharge saturated hydrocarbons.Type: GrantFiled: September 15, 1999Date of Patent: December 18, 2001Assignee: Oxeno Olefinchemie GmbHInventors: Alfred Kaizik, Bernhard Scholz, Walter Toetsch, Wilfried Bueschken, Franz Nierlich
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Patent number: 6310261Abstract: The invention relates to a method for the production of aldehydes or aldehydes and alcohols by hydroformylation of olefins in the presence of a complexing catalyst homogeneously dissolved in a reaction mixture, containing a metal of Group VIIIa of the periodic table of the elements and a phosphorus-free, polydentate nitrogen compound suitable for complex formation as ligand at temperatures ranging from 50 to 100° C.Type: GrantFiled: July 3, 2000Date of Patent: October 30, 2001Assignee: BASF AktiengesellschaftInventors: Bernhard Geissler, Michael Röper, Edgar Zeller, Rocco Paciello, Jürgen Decker, Hartwig Voss, Norbert Mahr
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Patent number: 6239318Abstract: The invention relates to a process for the selective hydrogenation of reaction mixtures from the hydroformylation of C5 to C24 olefins using hydrogen and a supported catalyst which, as active components, comprises copper, nickel and chromium.Type: GrantFiled: September 15, 1999Date of Patent: May 29, 2001Assignee: Oxeno Olefinchemie GmbHInventors: Joachim Schuler, Alfred Kaizik, Bernhard Scholz, Wilfried Bueschken, Wilhelm Droste