Group Va Element (n, P, As, Sb, Or Bi) Containing Material Utilized (e.g., Arsenic Containing Ligand Utilized, Etc.) Patents (Class 568/454)
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Publication number: 20040152924Abstract: 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 hydrogenType: ApplicationFiled: March 31, 2004Publication date: August 5, 2004Inventors: Otto Erik Sielcken, Hubertus Adrianus Smits, Imre Toth
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Patent number: 6768028Abstract: A composition and a process for using the composition in hydroformylation of unsaturated organic compounds are disclosed. The composition comprises a Group VIII metal and a phosphite-containing polymer having repeat units derived from (1) a carbonyl compound, a monomer, and phosphochloridite; (2) phosphorus trichloride, a polyhydric alcohol, and an aromatic diol; or (3) combinations of (1) and (2). The process comprises contacting an unsaturated compound, in the presence of the composition disclosed herein, with a fluid comprising hydrogen.Type: GrantFiled: May 17, 2002Date of Patent: July 27, 2004Inventors: Wilson Tam, Kathryn Eileen Schwiebert, Joe Douglas Druliner
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Publication number: 20040143140Abstract: A continuous process for producing an aldehyde comprising 1) feeding an olefinically unsaturated compound, carbon monoxide, hydrogen and a rhodium-organobisphosphite complex catalyst to a hydroformylation reactor and 2) reacting an olefinically unsaturated compound with carbon monoxide and hydrogen in the presence of a rhodium-organobisphosphite complex catalyst, whereinType: ApplicationFiled: March 12, 2004Publication date: July 22, 2004Inventors: Otto Erik Sielcken, Hubertus Adrianus Smits, Imre Toth
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Publication number: 20040138508Abstract: A continuous hydroformylation process for forming an aldehyde comprising:Type: ApplicationFiled: March 4, 2004Publication date: July 15, 2004Inventors: Johan Thomas Tinge, Hubertus Adrianus Smits
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Patent number: 6753450Abstract: The invention relates to a process for the preparation of aldehydes in which at least one compound containing a vinyl or vinylidene group is reacted with carbon monoxide and hydrogen in the presence of a source of a metal from sub-group VIII and in the presence of a bidentate diphosphine ligand, where the diphosphine ligand has the general formula I in which A together with the phosphorus atom to which it is bonded, in each case forms a 2-phosphatricyclo[3.3.1.1{3,7}]decyl radical, in which one or more non-adjacent carbon atoms may be replaced by oxygen atoms and which is substituted or unsubstituted, and X is a bridging chain having 1 to 10 carbon atoms, and the molar ratio between the diphosphine ligand and the metal is at least 5. The process gives predominantly n-aldehydes.Type: GrantFiled: November 7, 2002Date of Patent: June 22, 2004Assignee: BASF AktiengesellschaftInventors: Wolfgang Ahlers, Michael Slany
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Patent number: 6747179Abstract: A method for carrying out a catalysis reaction in carbon dioxide comprising contacting a fluid mixture with a catalyst bound to a polymer, the fluid mixture comprising at least one reactant and carbon dioxide, wherein the reactant interacts with the catalyst to form a reaction product. A composition of matter comprises carbon dioxide and a polymer and a reactant present in the carbon dioxide. The polymer has bound thereto a catalyst at a plurality of chains along the length of the polymer, and wherein the reactant interacts with the catalyst to form a reaction product.Type: GrantFiled: August 18, 2000Date of Patent: June 8, 2004Assignees: North Carolina State University, The University of North Carolina at Chapel Hill, Regents of University of CaliforniaInventors: Joseph M. DeSimone, Eva Birnbaum, Ruben G. Carbonell, Stephanie Crette, James B. McClain, T. Mark McCleskey, Kimberly R. Powell, Timothy J. Romack, William Tumas
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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: 6700021Abstract: 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: GrantFiled: July 3, 2002Date of Patent: March 2, 2004Assignee: Celanese Chemicals Europe GmbHInventors: Hans Bohnen, Carl Dieter Frohning, Ernst Wiebus
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Patent number: 6693219Abstract: A process for stabilizing a fluorophosphite ligand in a hydroformylation reaction mixture having an &agr;-olefin, hydrogen, carbon monoxide and a catalyst composition having a combination of a rhodium containing compound and one or more fluorophosphite compounds having the general formula: wherein R1 and R2 are hydrocarbyl radicals which contain a total of up to about 40 carbon atoms, the process includes the step of adding to the reaction mixture an epoxide in a sufficient amount to reduce the degradation of the fluorophosphite ligand.Type: GrantFiled: May 15, 2002Date of Patent: February 17, 2004Assignee: Eastman Chemical CompanyInventors: Thomas Allen Puckette, Ginette Struck Tolleson, Thomas James Devon, Jerome L. Stavinoha, Jr.
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Patent number: 6683118Abstract: According to the inventive method, the hydroformylation of the olefinically unsaturated compounds is carried out in the presence of an aqueous, water-soluble catalyst solution containing rhodium complex compounds, in a reaction column.Type: GrantFiled: April 30, 2002Date of Patent: January 27, 2004Assignee: Celanese Chemicals Europe GmbHInventor: Wolfgang Hofs
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Patent number: 6677268Abstract: An improved catalyst based on cobalt and/or rhodium dissolved in a non-aqueous ionic solvent which is liquid at a temperature of less than 90° C. More particularly, the catalyst comprises at least one complex of cobalt and/or rhodium co-ordinated with at least one nitrogen-containing ligand and the non-aqueous ionic solvent comprises at least one quaternary ammonium and/or phosphonium cation and at least one inorganic anion.Type: GrantFiled: July 12, 2002Date of Patent: January 13, 2004Assignee: Institut Francais du PetroleInventors: Gerhard Hillebrand, Andre Hirschauer, Dominique Commereuc, Helene Olivier-Bourbigou, Lucien Saussine
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Patent number: 6664427Abstract: The invention relates to a process for the making organic aldehyde compounds from an unsaturated compound by hydroformylation and in the presence of a catalyst system comprising a Group VIII metal and a bidentate phosphorus ligand having two trivalent phosphorus atoms bound to salicylanilide groups.Type: GrantFiled: August 29, 2002Date of Patent: December 16, 2003Assignee: E. I. du Pont de Nemours and CompanyInventors: Patrick M. Burke, James Michael Garner, Wilson Tam
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Patent number: 6642420Abstract: A process for the preparation of aldehydes and/or alcohols or amines by reacting olefins in the liquid phase with carbon monoxide and hydrogen, a part of these gases being dispersed in the form of gas bubbles in the reaction liquid and another part being dissolved in the reaction liquid, in the presence or absence of a primary or secondary amine and in the presence of a cobalt carbonyl, rhodium carbonyl, palladium carbonyl or ruthenium carbonyl complex dissolved homogeneously in the reaction liquid and having a phosphorus-, arsenic-, antimony- or nitrogen-containing ligand, at elevated temperatures and at 1 to 100 bar, wherein the reaction is carried out in a vertically arranged, tubular reactor comprising a reactor body and at least one circulation line, a part of the reaction liquid is fed continuously via the circulation line to at least one nozzle which is mounted in the upper part of the reactor body and is coordinated with a guide member, open at the top and bottom and bounded by parallel walls, in theType: GrantFiled: February 7, 2001Date of Patent: November 4, 2003Assignee: BASF AktiengesellschaftInventors: Peter Zehner, Armin Ulonska, Rocco Paciello
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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: 20030171623Abstract: 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: ApplicationFiled: January 22, 2002Publication date: September 11, 2003Inventors: Thomas Allen Puckette, Ginette Struck Tolleson
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Patent number: 6617474Abstract: A process for the hydroformylation of an olefinically unsaturated compound in the liquid phase by reaction, in a reaction section, with carbon monoxide and hydrogen in the presence of a polar phase comprising: a non-aqueous ionic liquid which is at least partly miscible with the reaction products and comprises a salt of general formula Q+A−, in which Q+ represents a quaternary ammonium and/or phosphonium and A− represents an anion; and a catalyst comprising a compound or a complex of a transition metal of groups 8, 9 and 10, optionally co-ordinated with a ligand containing at least one atom of phosphorus, arsenic, antimony or nitrogen, comprises addition to the medium, after the reaction section, of an organic solvent in a manner such as to improve the separation by demixing of the crude reaction products from the said polar phase, which is recycled to the reaction section.Type: GrantFiled: January 24, 2002Date of Patent: September 9, 2003Assignee: Institut Francais du PetroleInventors: Frédéric Favre, Dominique Commereuc, Hélène Olivier-Bourbigou
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Patent number: 6610891Abstract: A method of producing aldehydes in a hydroformylation system wherein an olefinic compound is reacted with hydrogen and carbon monoxide in a hydroformylation reaction in the presence of a catalyst is provided. The hydroformylation system includes a reactor and a downstream catalyst process path. The temperature in the reactor and downstream catalyst process path is less than approximately 100° C., and preferably less than approximately 85° C., and most preferably less than approximately 80° C., such that formation of high boiler components from the reaction are substantially minimized. Further, the method of the present invention reduces degradation or decomposition of the catalyst, and in particular the ligand compound.Type: GrantFiled: December 3, 1999Date of Patent: August 26, 2003Assignee: Mitsubishi Chemical CorporationInventors: Lionel O'Young, Masaki Takai, Tooru Tsukahara, Akio Nakanishi
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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: 20030158427Abstract: A process for preparing compounds of the formula I 1Type: ApplicationFiled: January 6, 2003Publication date: August 21, 2003Inventors: Hansgeorg Ernst, Klaus Henrich
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Patent number: 6583324Abstract: A process for producing an aldehyde, which comprises a reaction step of producing an aldehyde by reacting an olefinic compound with carbon monoxide and hydrogen in the presence of a rhodium complex catalyst comprising at least rhodium and an organic phosphite in a reaction zone, a separation step of obtaining a catalyst solution containing the rhodium complex catalyst by separating the aldehyde from a reaction solution taken from the reaction zone, and a recycling step of recycling the catalyst solution into the reaction zone, wherein the aldehyde is separated from the reaction solution in such a manner as to make an aldehyde concentration from 0.5 to 99 wt % in the catalyst solution.Type: GrantFiled: September 18, 2001Date of Patent: June 24, 2003Assignee: Mitsubishi Chemical CorporationInventors: Masaki Takai, Iwao Nakajima, Tooru Tsukahara, Yoshiyuki Tanaka, Hisao Urata, Akio Nakanishi
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Patent number: 6566558Abstract: In a process for the hydroformylation of alkanes, alkenes or trialkylboranes under supercritical or near-critical conditions, hydroformylation is effected using a heterogeneous catalyst in a continuous flow reactor containing a supercritical or near-critical reaction medium. Selectivity of product formation may be achieved by independently varying one of more of the temperature, pressure, catalyst, mole ratios of hydrogen and carbon monoxide and flow rate.Type: GrantFiled: March 12, 2001Date of Patent: May 20, 2003Assignee: Thomas Swan & Co., LimitedInventors: Martyn Poliakoff, Nicola J. Meehan, Stephen K. Ross, Stefan Wieland, Stefan Roeder
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Publication number: 20030092935Abstract: In a process for the hydroformylation of ethylenically unsaturated compounds, at least one ethylenically unsaturated compound is reacted with carbon monoxide and hydrogen in the presence of a ligand-metal complex of ruthenium, rhodium, palladium, iridium and/or platinum, where the ligand-metal complex comprises a monophosphine, monophosphinite or monophosphinamidite ligand of the formula I 1Type: ApplicationFiled: November 7, 2002Publication date: May 15, 2003Inventor: Wolfgang Ahlers
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Patent number: 6559344Abstract: 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: GrantFiled: February 19, 2002Date of Patent: May 6, 2003Assignee: BASF AktiengesellschaftInventor: Thomas Mackewitz
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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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Patent number: 6525143Abstract: This invention relates to dendritic macromolecules and their use in metal-dendritic macroligand complex catalyzed processes, e.g., hydroformylation. The use of metal-dendritic macroligand complex catalysts in such processes facilitates the separation of desired product from catalyst, for example, by membrane filtration.Type: GrantFiled: November 16, 2001Date of Patent: February 25, 2003Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Michael Leo Tulchinsky, David James Miller
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Patent number: 6515161Abstract: A hydroformylation process is disclosed which employs multidentate phosphite ligands in a catalyst composition. In particular, the ligands have heteroatom-containing substituents on the carbon attached to the ortho position of the terminal phenol group.Type: GrantFiled: August 30, 2000Date of Patent: February 4, 2003Assignee: E. I. du Pont de Nemours and CompanyInventors: Kristina Ann Kreutzer, Wilson Tam, John Ronald Boyles, J Michael Garner
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Publication number: 20030018220Abstract: A process for stabilizing a fluorophosphite ligand in a hydroformylation reaction mixture having an &agr;-olefin, hydrogen, carbon monoxide and a catalyst composition having a combination of a rhodium containing compound and one or more fluorophosphite compounds having the general formula: 1Type: ApplicationFiled: May 15, 2002Publication date: January 23, 2003Applicant: Eastman Chemical CompanyInventors: Thomas Allen Puckette, Ginette Struck Tolleson, Thomas James Devon, Jerome L. Stavinoha
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Patent number: 6509505Abstract: Phosphabenzene compounds of the formula (I) where the radicals R1 to R13 are, independently of one another, hydrogen, COOM, SO3M, NR3X, NR2, OR, COOR or SR (where M=hydrogen, NH4 or alkali metal, X=anion, R=hydrogen or C1-C6-alkyl), or C1-C12-alkyl, C6-C12-aryl, C7-C12-aralkyl, C7-C12-alkaryl or C3-C6-heteroaromatics, where the alkyl, aryl, alkaryl and aralkyl radicals may bear the abovementioned radicals as substituents and two or more of the radicals may be joined to form aliphatic or fused-on rings, where at least one of the radicals R4 and R8 and at least one of the radicals R9 and R13 is not hydrogen, can be used for preparing hydroformylation catalysts.Type: GrantFiled: September 11, 2001Date of Patent: January 21, 2003Assignee: BASF AktiengesellschaftInventors: Rocco Paciello, Thomas Mackewitz, Michael Röper, Bernhard Breit
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Patent number: 6500991Abstract: Aldehydes are prepared by a process, which comprises: hydroformylating olefins having 3 to 21 carbon atoms under an atmosphere of CO/H2 in the presence of a rhodium catalyst in a hydroformylation reactor; and upon discharging the reaction product from the reactor, a) separating the discharged material into a gaseous phase and a liquid phase, b) separating the liquid phase into a top fraction containing unconverted olefins and aldehydes and a bottoms fraction containing the rhodium catalyst, and c) cooling the bottoms fraction below the temperature of the material discharged from the hydroformylation reactor and feeding a gas containing carbon monoxide into the bottoms fraction.Type: GrantFiled: September 25, 2001Date of Patent: December 31, 2002Assignee: Oxeno Olefinchemie GmbHInventors: Klaus-Diether Wiese, Martin Trocha, Dirk Röettger, Walter Töetsch, Alfred Kaizik, Wilfried Büschken
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Patent number: 6492564Abstract: The invention relates to a catalytic process for carrying out multiphase reactions in a tubular reactor, with the catalyst being present in the continuous phase and at least one starting material in a disperse phase and the loading factor B of the tubular reactor being equal to or greater than 0.8. The process is especially suitable in particular for the hydroformylation of olefins. The aldehydes thus prepared can ideally be used for the preparation of alcohols, carboxylic acids or in aldol condensations.Type: GrantFiled: June 2, 2000Date of Patent: December 10, 2002Assignee: OXENO Olefinchemie GmbHInventors: Klaus-Diether Wiese, Guido Protzmann, Juergen Koch, Dirk Roettger, Martin Trocha
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Publication number: 20020177737Abstract: A composition and a process for using the composition in hydroformylation of unsaturated organic compounds are disclosed. The composition comprises a Group VIII metal and a phosphite-containing polymer having repeat units derived from (1) a carbonyl compound, a monomer, and phosphochloridite; (2) phosphorus trichloride, a polyhydric alcohol, and an aromatic diol; or (3) combinations of (1) and (2). The process comprises contacting an unsaturated compound, in the presence of the composition disclosed herein, with a fluid comprising hydrogen.Type: ApplicationFiled: May 17, 2002Publication date: November 28, 2002Inventors: Wilson Tam, Kathryn Eileen Schwiebert, Joe Douglas Druliner
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Patent number: 6486359Abstract: The invention relates to a catalyst which comprises at least one complex of a metal of group VIII, which comprises at least one uni-, bi- or multidentate phosphinite ligand in which the phosphorus atom and the oxygen atom of the phosphinite group are part of a 5- to 8-membered heterocycle, and to processes for hydroformylation and hydrocyanation of compounds which contain at least one ethylenic double bond in the presence of a catalyst of this type.Type: GrantFiled: December 12, 2000Date of Patent: November 26, 2002Assignee: BASF AktiengesellschaftInventors: Heiko Maas, Rocco Paciello, Michael Röper, Jakob Fischer
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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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Patent number: 6472565Abstract: The invention relates to a method for producing aldehydes by reacting monoolefins, conjugated and non-conjugated polyolefins, cycloolefins, or derivatives of these classes of compounds with carbon monoxide and hydrogen (hydroformylation) in the presence of rhodium or rhodium compounds and a non-aqueous liquid of the formula (Q30 )aAa−, wherein Q+represents a singly charge ammonium cation that is optionally substituted with organic radicals, and Aa−represents the anion of a sulphonated or carboxylated triester of phosphoric acid.Type: GrantFiled: October 23, 2001Date of Patent: October 29, 2002Assignee: Celanese Chemicals Europe GmbHInventors: Helmut Bahrmann, Hans Bohen
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Patent number: 6469216Abstract: In an improved process for hydroformylation of olefinically unsaturated compounds using a catalyst based on cobalt and/or rhodium employed in a two-phase medium, a catalyst based on cobalt and/or rhodium is used dissolved in a non-aqueous ionic solvent which is liquid at a temperature of less than 90° C., in which the aldehydes formed are slightly soluble or insoluble. More particularly, the catalyst comprises at least one complex of cobalt and/or rhodium co-ordinated with at least one nitrogen-containing ligand and the non-aqueous ionic solvent comprises at least one quaternary ammonium and/or phosphonium cation and at least one inorganic anion. At the end of the reaction, the organic phase is generally separated and the ionic non-aqueous solvent phase containing the catalyst can be re-used.Type: GrantFiled: December 7, 2000Date of Patent: October 22, 2002Assignee: Institut Francais du PetroleInventors: Gerhard Hillebrand, André Hirschauer, Dominique Commereuc, Hélène Olivier-Bourbigou, Lucien Saussine
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Patent number: 6455740Abstract: Process to separate a group 8-10 metal/phosphite ligand complex from an organic liquid mixture, wherein the following steps are performed (1) contacting the organic liquid with a support having bonded thereto an organophosphine ligand and separating the organic mixture which is poor in group 8-10 metal/phosphite ligand complex, (2) contacting the thus obtained loaded support with an organic solvent and carbon monoxide and separating the thus obtained organic solvent rich in group 8-10 metal/phosphite ligand complex, and (3) reusing the support obtained in step (2) in step (1).Type: GrantFiled: February 8, 2000Date of Patent: September 24, 2002Assignee: DSM N.V.Inventors: Nicolaas L. H. L. Broeders, Onko J. Gelling, Hendrik F. Martens, Klaas Timmer, Harmen A. Meinema
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Patent number: 6452055Abstract: This invention relates to a process for the catalytic hydroformylation of olefins by reaction of an olefin with hydrogen and carbon monoxide in a liquid, aqueous-organic reaction medium in the presence of a water-soluble hydroformylation catalyst, characterized in that for a substantial period of the hydroformylation reaction, the aqueous-organic medium is present in the form of a microemulsion, which is made up of an oil phase containing the olefin or the olefin and its hydroformylation products, an aqueous phase containing the water-soluble complex catalyst, and a nonionic surfactant.Type: GrantFiled: January 5, 2001Date of Patent: September 17, 2002Assignee: Sasol Germany GmbHInventors: Herbert Koch, Reinhard Schomaecker, Marco Haumann
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Patent number: 6444856Abstract: In a process for preparing aldehydes and/or alcohols having from 6 to 30 carbon atoms by hydroformylation of olefins by means of synthesis gas in the presence of a catalyst at from 120° C. to 210° C. and pressures of from 100 to 400 bar, a reaction mixture comprising olefins, synthesis gas and catalyst or catalyst precursor is, according to the present invention, introduced at high velocity into a high-pressure reactor via a nozzle having an adjustable flow cross section.Type: GrantFiled: May 31, 2001Date of Patent: September 3, 2002Assignee: BASF AktiengesellschaftInventors: Armin Volker Grenacher, Hans-Georg Hein, Hans Stepp, Hans-Jürgen Fröhlich, Willi Schönmann, Gerhard Borchert
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Patent number: 6440891Abstract: The catalyst comprises at least one bi- or more highly dentate phosphonite ligand of the general formula I or salts and mixtures thereof and is useful in a process for hydroformylating compounds containing at least one ethylenically unsaturated double bond by reaction with carbon monoxide and hydrogen.Type: GrantFiled: August 29, 2000Date of Patent: August 27, 2002Assignee: BASF AktiengesellschaftInventors: Heiko Maas, Rocco Paciello, Michael Röper, Jakob Fischer, Wolfgang Siegel
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Patent number: 6437192Abstract: A hydroformylation process comprising the steps of: (a) reacting a conjugated C4 to C20 alkadiene with CO and H2 in the presence of a catalyst composition to form a product comprising at least one alkenal wherein said catalyst composition comprises a Group VIII metal or Group VIII metal compound and at least one phosphonite ligand having a structure: wherein R1, R2 and R3 are independently selected from the group consisting of hydrogen, alkyl of 1 to 20 carbon atoms, aralkyl of 7 to 15 carbon atoms and aryl of 6 to 10 carbon atoms, and wherein X1 and X2 are independently selected from the group consisting of a direct bond and alkylidene of 1 to 20 carbon atoms; and then (a) recovering at least one alkenal. The process is particularly useful to produce pentenals from butadiene.Type: GrantFiled: November 17, 2000Date of Patent: August 20, 2002Assignee: E. I. Du Pont de Nmeours and CompanyInventor: Emilio E Bunel
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Patent number: 6420611Abstract: A composition comprising a Group VIII metal and a phosphite-containing polymer having repeat units derived from (1) a carbonyl compound, a monomer, and phosphochloridite; (2) phosphorus trichloride, a polyhydric alcohol, and an aromatic diol; or (3) combinations of (1) and (2).Type: GrantFiled: September 20, 1999Date of Patent: July 16, 2002Assignee: E. I. du Pont de Nemours and CompanyInventors: Wilson Tam, Kathryn Eileen Schwierbert
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Patent number: 6403837Abstract: A process for preparing aldehydes having from 4 to 25 carbon atoms by catalytic hydroformylation of the corresponding olefins, wherein the catalyst used comprises a metal of transition group 8 of the Periodic Table in the presence of a ligand A of the formula I where X=As, Sb or P and R1,R2,R3: are each a substituted or unsubstituted aliphatic, cycloaliphatic or aromatic hydrocarbon radical having from 1 to 50 carbon atoms, where two of the radicals R1, R2, R3 can be covalently linked with the proviso that at least one of the hydrocarbon radicals R1, R2, R3 contains a heteroatom selected from the group consisting of O, S, N, F, Cl, Be, I, Se and Te, and a ligand B of the formula II where R4, R5, R6: are each a substituted or unsubstituted aliphatic, cycloaliphatic or aromatic hydrocarbon having from 1 to 50 carbon atoms, where two of the radicals R4, R5 and R6 can be covalently linked.Type: GrantFiled: November 9, 2000Date of Patent: June 11, 2002Assignee: Oxeno Olefinchemie GmbHInventors: Dieter Hess, Dirk Roettger, Detlef Selent, Armin Boerner
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Patent number: 6399834Abstract: The present invention relates to methods for producing chiral aldehydes by the enantioselective hydroformylation of prochiral substrates with the aid of a catalyst consisting of a transition metal and a chiral ligand, characterized in that said chiral ligand is a compound of general formula 1 wherein the rings R7-R10 drawn with dotted lines are optional and one or more of rings R1-R6 or R7-R10 are substituted with one or more independently selected substituents of general formula —(CH2)x(CF2)yF(x=0-5; y=1-12) or their branched isomers. In particular, the invention relates to the conducting of the mentioned methods in compressed (liquid or supercritical) carbon dioxide as the reaction medium.Type: GrantFiled: May 15, 2001Date of Patent: June 4, 2002Assignee: Studiengesellschaft Kohle mbHInventors: Walter Leitner, Sabine Kainz, Daniel Koch, Giancarlo Francio
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Patent number: 6399534Abstract: This invention relates to multidentate organic phosphite ligands and their compositions with Group VIII metals.Type: GrantFiled: July 26, 2001Date of Patent: June 4, 2002Assignee: E. I. du Pont de Nemours and CompanyInventors: Emilio E. Bunel, Helen S. M. Lu, Kenneth Gene Moloy, Shawn H. Phillips, Kathryn E. Schwiebert, Wilson Tam, Nora Radu
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Publication number: 20020065437Abstract: Aldehydes are prepared by a process, which comprises:Type: ApplicationFiled: September 25, 2001Publication date: May 30, 2002Inventors: Klaus-Diether Wiese, Martin Trocha, Dirk Roettger, Walter Totsch, Alfred Kaizik, Wilfried Buschken
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Patent number: 6388142Abstract: The invention relates to a method for producing aldehydes by reacting one olefine containing 3 to 12 carbon atoms with hydrogen and carbon monoxide in the presence of one rhodium catalyst. The invention is characterized in that (a) the rhodium catalyst is present in an aqueous phase, whereby the aqueous phase contains i) rhodium in an elemental or bonded form, ii) one trisulfonated triaryl phosphine, and iii) one crown etherl (b) the olefine is present in the reaction conditions in a liquid organic phase which cannot be mixed with the aqueous phase.Type: GrantFiled: May 16, 2000Date of Patent: May 14, 2002Assignee: Celanese Chemicals Europe GmbHInventors: Sandra Bogdanovic, Klaus Kuhlein
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Patent number: 6388141Abstract: The present invention relates to processes for the preparation of oxo products by the hydroformylation of substrates having C═C double bonds using unmodified rhodium catalysts in a reaction mixture essentially consisting of the substrates, the catalyst and carbon dioxide in a supercritical state (scCO2). In particular, the invention relates to such processes for the preparation of products which contain substantial proportions of branched i-oxo products. Further, the invention relates to such processes for the hydroformylation of substrates which do not correspond to the general formula CnH2n. The invention further relates to such processes in which the separation of product and catalyst is effected using the special solvent properties of scCO2.Type: GrantFiled: January 13, 2000Date of Patent: May 14, 2002Assignee: Studiengesellschaft Kohle mbHInventors: Walter Leitner, Daniel Koch
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Publication number: 20020049355Abstract: A process for producing an aldehyde, which comprises a reaction step of producing an aldehyde by reacting an olefinic compound with carbon monoxide and hydrogen in the presence of a rhodium complex catalyst comprising at least rhodium and an organic phosphite in a reaction zone, a separation step of obtaining a catalyst solution containing the rhodium complex catalyst by separating the aldehyde from a reaction solution taken from the reaction zone, and a recycling step of recycling the catalyst solution into the reaction zone, wherein the aldehyde is separated from the reaction solution in such a manner as to make an aldehyde concentration from 0.5 to 99 wt % in the catalyst solution.Type: ApplicationFiled: September 18, 2001Publication date: April 25, 2002Applicant: MITSUBISHI CHEMICAL CORPORATIONInventors: Masaki Takai, Iwao Nakajima, Tooru Tsukahara, Yoshiyuki Tanaka, Hisao Urata, Akio Nakanishi
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Patent number: 6369257Abstract: Supported bis(phosphorus) ligands are disclosed for use in hydroformylation reactions, including the hydroformylation of olefins. Catalysts are formed when the ligands are complexed with a catalytically active metal (e.g., rhodium or iridium).Type: GrantFiled: February 16, 2001Date of Patent: April 9, 2002Assignee: E. I. du Pont de Nemours and CompanyInventors: Emilio E. Bunel, Patrick Michael Burke, Joe Douglas Druliner, Leo Ernest Manzer, Kenneth Gene Moloy, Manxue Wang
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Patent number: 6350819Abstract: This invention relates to dendritic macromolecules and their use in metal-dendritic macroligand complex catalyzed processes, e.g., hydroformylation. The use of metal-dendritic macroligand complex catalysts in such processes facilitates the separation of desired product from catalyst, for example, by membrane filtration.Type: GrantFiled: October 27, 2000Date of Patent: February 26, 2002Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Michael Leo Tulchinsky, David James Miller