Hydroformylation By Reacting Ethylenically Unsaturated Compound, Carbon Monoxide, And Gaseous Hydrogen Patents (Class 568/451)
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Patent number: 6187962Abstract: The invention relates to a hydroformylation process comprising the steps of: (a) contacting one or more ethylenically unsaturated compound(s) in a reaction zone with carbon monoxide and hydrogen gas in the presence of a solvent and a homogeneous catalyst based on a Group 8, 9 or 10 metal, and a non-ionically charged phosphorus ligand to form a crude hydroformylation product; (b) allowing a major portion of the solvent, wherein a major portion of the catalyst is dissolved, to separate and be withdrawn from the crude hydroformylation product in a phase separation zone; (c) removing from the separated hydroformylation product emerging from step (b) substantially all remaining catalyst dissolved therein with a non-aqueous extractant in an extraction zone.Type: GrantFiled: February 10, 1999Date of Patent: February 13, 2001Assignee: Shell Oil CompanyInventors: Peter Arnoldy, Cornelis Mark Bolinger, Eit Drent, Johan Van Gogh, Cornelis Hyacinthus Maria Van Der Hulst, Robert Moene
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Patent number: 6175043Abstract: The present invention provides an improved hydroformylation process in which the catalyst system is composed of a Group VIII metal and organic phosphite ligand having the structure P(OR)2-OR′O—P(OR)2 or P(OR)3, where R and R′ are organic residues which may be the same or different and where the R or R′ contain at least one C9 to C40 aliphatic group positioned as a tail extending away from the primary ligand structure rendering the ligand lipophilic.Type: GrantFiled: December 11, 1998Date of Patent: January 16, 2001Assignees: E. I. du Pont de Nemours and Company, DSM N.V.Inventor: Emilio Enrique Bunel
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Patent number: 6172267Abstract: A process for producing aldehydes, which comprises reacting a mono-olefinic compound with carbon monoxide and hydrogen in the presence of a Group VIII transition metal compound of a bisphosphite compound of the following formula (1) or (2)Type: GrantFiled: October 27, 1998Date of Patent: January 9, 2001Assignee: Mitsubishi Chemical CorporationInventors: Hisao Urata, Yasuhiro Wada, Yoshiyuki Tanaka, Naoki Suzuki, Hiroaki Itagaki
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Patent number: 6166262Abstract: Branched-chain olefins are prepared and used as feedstocks in the manufacture of detersive surfactants.Type: GrantFiled: October 13, 1998Date of Patent: December 26, 2000Assignee: The Procter & Gamble CompanyInventor: Daniel Stedman Connor
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Patent number: 6156936Abstract: A process for the hydroformylation of a feed comprising compounds having a single ethylenically unsaturated group by reaction thereof in the liquid phase with carbon monoxide and hydrogen in the presence of a catalyst system comprising a) a source of palladium cations;b) a source of anions;c) a source of at least one bidentate ligands of the formulaR.sup.1 R.sup.2 M.sup.1 RM.sup.2 R.sup.3 R.sup.4 (I)characterized in that the ethylenically unsaturated feed comprises one or more dienes and/or further multiply unsaturated alkenes to an amount of 0.005-5 wt % based on the total amount of ethylenically unsaturated compounds in the feed, and in that component b) of the catalyst system is a source of anions of an acid having a pKa value, measured in aqueous solution at 18.degree. C., of between -1 and 4.Type: GrantFiled: February 23, 1999Date of Patent: December 5, 2000Assignee: Shell Oil CompanyInventors: Eit Drent, Frederik Hendrik Van Der Steen, Robert Moene
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Patent number: 6153800Abstract: Process for the preparation of an aldehyde through hydroformylation of an unsaturated organic compound in the presence of a catalyst system comprising rhodium of iridium and a multidentate organic phosphite ligand, wherein a monodentate phosphine is present.The process according to the invention can advantageously be carried out for the preparation of methyl-5-formylvalerate, which is an intermediate product in the preparation of a caprolactam or adipic acid, which are in turn raw materials for the preparation of nylon-6 and nylon-6,6, respectively.Type: GrantFiled: May 3, 1999Date of Patent: November 28, 2000Assignees: DSM N.V., E.I. du Pont de Nemours and CompanyInventors: Onko J. Gelling, Peter C. Borman, Petrus W. N. M. Van Leeuwen
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Patent number: 6130358Abstract: This invention relates to a hydroformylation process for preparing an aldehyde, which comprises reacting an olefin with hydrogen and carbon monoxide in the presence of a catalyst solution comprising of rhodium, a hydroformylation solvent and a chlorophosphite compound having the general formula ##STR1##Type: GrantFiled: October 16, 1998Date of Patent: October 10, 2000Assignee: Eastman Chemical CompanyInventors: Ginette Struck Tolleson, Thomas Allen Puckette
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Patent number: 6127582Abstract: A process for the hydroformylation of ethylenically unsaturated compounds with carbon monoxide and hydrogen in the presence of a catalyst system comprisinga) a source of platinum group metal cations;b) a source of non-halide anions;c) a source of at least one bidentate ligand of the formulaR.sup.1 R.sup.2 M.sup.1 RM.sup.2 R.sup.3 R.sup.4 (I)wherein M.sup.1 and M.sup.2 independently represent a phosphorus, arsenic or antimony atom, R represents a bivalent bridging group containing from 1-4 atoms in the bridge, R.sup.1 and R.sup.2 together represent a bivalent substituted or unsubstituted cyclic group whereby the two free valencies are linked to M.sup.1, and R.sup.3 and R.sup.4 independently represent a substituted or unsubstituted hydrocarbyl group, or together represent a bivalent substituted or unsubstituted cyclic group whereby the two free valencies are linked to M.sup.Type: GrantFiled: August 27, 1997Date of Patent: October 3, 2000Assignee: Shell Oil CompanyInventors: Cornelius Mark Bolinger, Peter Arnoldy, Wilhelmus Petrus Mul
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Patent number: 6114588Abstract: A method to produce dialcohols is provided, the method comprising the steps of:providing a feed stream comprising an alpha-alcohol-diolefin;reacting the feed stream with hydrogen and carbon monoxide in the presence of a catalyst system comprising a cobalt phosphine ligand complex under conditions effective to hydroformylate at least a portion of the diolefin in the feed stream; andrecovering the dialcohol from the reacted feed stream. This method is a one-step process to hydroformylate alpha-alcohol-diolefins such as 2,7-octadien-1-ol to produce a significant yield of dialcohols such as 1,9-nonanediol.Type: GrantFiled: June 11, 1998Date of Patent: September 5, 2000Assignee: Shell Oil CompanyInventors: Pui-Kwan Wong, Andrew Allison Moxey
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Patent number: 6107524Abstract: A process for the preparation of aldehydes or aldehydes and alcohols by hydroformylation of olefins containing more than 3 carbon atoms comprising a hydroformylation stage, in which the olefin is hydroformylated under a pressure of from 50 to 1000 bar and at a temperature of from 50.degree. to 180.degree. C.Type: GrantFiled: July 15, 1998Date of Patent: August 22, 2000Assignee: BASF AktiengesellschaftInventors: Rocco Paciello, Heinz-Josef Kneuper, Bernhard Geissler, Michael Roper
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Patent number: 6100432Abstract: A process for the purification of a substantially liquid effluent containing aldehydes and unconverted olefins coming from a hydroformylation reactor following low-pressure hydroformylation of C.sub.2 -C.sub.20 olefins or olefin mixtures containing different isomers of the respective olefins, said hydroformylation being catalyzed by means of a phosphorous rhodium catalyst homogeneously dissolved in the reaction medium and carried out at a temperature of from 50.degree. to 150.degree. C. and a pressure of from 2 to 30 bar.Type: GrantFiled: May 29, 1998Date of Patent: August 8, 2000Assignee: BASF AktiengesellschaftInventors: Franz Borgel, Rolf Muller, Roland Krokoszinski
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Patent number: 6090987Abstract: This invention relates to a method of stabilizing a metal-organophosphorus ligand complex catalyst against deactivation in a process which comprises reacting one or more reactants in the presence of a metal-organophosphorus ligand complex catalyst and optionally free organophosphorus ligand to produce a reaction product fluid comprising one or more products, and in which at least a portion of said process is conducted under separation conditions sufficient to effect at least some deactivation of the metal-organophosphorus ligand complex catalyst, which method comprises conducting the portion of said process that occurs under separation conditions in the presence of one or more alkadienes sufficient to prevent and/or lessen deactivation of the metal-organophosphorus ligand complex catalyst.Type: GrantFiled: July 6, 1998Date of Patent: July 18, 2000Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Ernst Billig, David Robert Bryant, Craig Alan Beasley, Donald Lee Morrison, Michael David Warholic, Kenneth Elwood Stockman
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Patent number: 6090986Abstract: Esters of branched C.sub.9 alcohols suitable as plasticizers are formed by esterification of a C.sub.9 alcohol produced by the aldol condensation from propanal and a C.sub.6 aldehyde and hydrogenation, the propanal optionally having been made from natural gas streams.Type: GrantFiled: October 27, 1997Date of Patent: July 18, 2000Assignee: Exxon Chemical Patents Inc.Inventors: Allen David Godwin, Richard Henry Schlosberg, Frank Hershkowitz, Michael G. Matturro, Gabor Kiss, Kirk Christian Nadler, Philippe Louis Buess, Richard C. Miller, Paul William Allen, Harry William Deckman, Raf Caers, Edmund John Mozeleski, Robert P Reynolds, Francis Joseph Healy
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Patent number: 6087481Abstract: The present invention relates to a process for the hydroformylation of terminal and internal olefins in a two-phase system using novel metal catalysts. The two-phase system consists of an aqueous and an organic phase. The metals belong to group VIII of the Periodic Table, e.g., Rh, Ru, Ir, Co or Pd. The ligands for the metals are novel phosphane-modified .beta.-cyclodextrins which are water-soluble.Type: GrantFiled: January 27, 1999Date of Patent: July 11, 2000Assignee: Studiengesellschaft Kohle mbHInventors: Manfred T. Reetz, Siegfried Waldvogel
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Patent number: 6049011Abstract: A dilute ethylene stream, e.g., one produced by steam cracking, is oxonated to yield propanal, without the need to separate other lower hydrocarbons.Type: GrantFiled: October 15, 1997Date of Patent: April 11, 2000Assignee: Exxon Chemical Patents Inc.Inventors: Gabor Kiss, Michael G Matturro, Harry William Deckman, Frank Hershkowitz, David R. Lumgair, Jr., Gary F Janda, Daniel N King
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Patent number: 6040483Abstract: Process for liquid-phase hydroformylation of at least one olefin by carbon oxide and hydrogen oxide in the presence of a catalytic composition that contains at least one compound of a transition metal, at least one phosphine oxide, and at least one organic-inorganic salt that does not contain tin or germanium; said salt is a quaternary ammonium salt and/or a quaternary phosphonium salt of general formula Q.sup.+ A.sup.-, in which Q.sup.+ represents an ammonium and/or a quaternary phosphonium and A.sup.- represents an anion. The process applies in particular to internal olefins.Type: GrantFiled: May 27, 1998Date of Patent: March 21, 2000Assignee: Institut Francais du PetroleInventors: Helene Olivier, Dominique Commereuc, Sebastien Drochon
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Patent number: 6025529Abstract: A process for preparing aldehydes by hydroformylation of olefins or olefinically unsaturated compounds in the presence of a catalyst of at least one rhodium compound and a nonaqueous ionic ligand liquid of the formula (Q.sup.+).sub.a A.sup.a-, where Q.sup.+ is a singly charged quaternary ammonium and/or phosphonium cation or the equivalent of a multiply charged ammonium and/or phosphonium cation and A.sup.a- is a sulfonated triarylphosphine.Type: GrantFiled: December 15, 1998Date of Patent: February 15, 2000Assignee: Celanese GmbHInventor: Helmut Bahrmann
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Patent number: 6020532Abstract: A process for preparing aldehydes by hydroformylating olefinically unsaturated compounds in the presence of a water-insoluble catalyst composition comprising rhodium complexes containing diphosphine ligands, wherein the diphosphine ligands present are compounds of the formula (I) ##STR1## wherein R.sup.1 is selected from the group consisting of carboxylate (COO.sup.-), sulfonate (SO.sub.3.sup.-), phosphonate (PO.sub.3.sup.2-) and 2-anmino ethtanebisphosphonate, R.sup.Type: GrantFiled: July 9, 1998Date of Patent: February 1, 2000Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Peter Lappe, Thomas Muller
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Patent number: 6018081Abstract: A hydroformylation process for preparating a terminal aldehyde involves reacting an ethylenically unsaturated organic compound with carbon monoxide and hydrogen in the presence of a catalyst system iridium or rhodium and a bidentate organic phosphite ligand wherein the two phosphorus atoms of the phopshite ligand are linked with a 2,2'-dihydroxyl-1,1'-binapthalene bridging group having the following structure (Q): ##STR1## in which R.sup.1 and R.sup.2 are substituents other than hydrogen and in which R.sup.3 and R.sup.4 are the same or different substituted monovalent aryl groups and/or any one of OR.sup.3 and OR.sup.4 connected to one phosphorus atom forms an --O--R.sup.5 --O-group, where R.sup.5 is a divalent organic group containing one or two aryl groups.Type: GrantFiled: April 28, 1997Date of Patent: January 25, 2000Assignees: DSM N.V., EI DuPont De Nemours and CompanyInventors: Patrick M. Burke, James M. Garner, Wilson Tam, Kristina A. Kreutzer, Antonius J. J. M. Teunissen, Carina S. Snijder, Carolina B. Hansen
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Patent number: 6015928Abstract: A single-stage process is described that includes simultaneously, in a mixture containing an olefin; synthesis gas; a cobalt catalyst in an organic phase; and an aqueous cobalt salt solution; hydroformylating the olefin, and forming and extracting into the organic phase the cobalt catalyst from the aqueous cobalt salt solution. An apparatus is also described that includes a means for carrying out the process. The process is particularly suitable for preparing aldehydes and alcohols.Type: GrantFiled: December 15, 1997Date of Patent: January 18, 2000Assignee: Huels AktiengesellschaftInventors: Dietmar Gubisch, Klaus Armbrust, Alfred Kaizik, Bernhard Scholz, Rudolf Nehring
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Patent number: 6013816Abstract: Process for the preparation of a linear .omega.-formyl-carboxylic acid or a corresponding linear formylnitrile compound starting from an internally unsaturated C.sub.4 -C.sub.12 carboxylic acid or a corresponding ester or nitrile by means of hydroformylation in the presence of carbon monoxide, hydrogen and a catalyst system, wherein the hydroformylation is carried out in an aqueous medium and in that the catalyst system comprises platinum and a water-soluble organic bidentate ligand.Type: GrantFiled: July 5, 1996Date of Patent: January 11, 2000Assignee: DSM NVInventors: Onko J. Gelling, Imre Toth
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Patent number: 5994591Abstract: A process for the hydroformylation of ethylenically unsaturated compounds with carbon monoxide and hydrogen in the presence of a catalyst system comprising:a) a source of palladium, platinum, or nickel cations;b) a source of anions, other than halide anions, such as unsubstituted alkyl sulfonic acids, aryl sulfonic acids, perfluorinated alkyl sulfonic acids, perfluorinated aryl sulfonic acids, boric acid derivatives or alkylated versions thereof;c) a source of at least one bidentate ligands of the formulaR.sup.1 R.sup.2 M.sup.1 RM.sup.2 R.sup.3 R.sup.4 (I)wherein M.sup.1 and M.sup.2 independently represent a phosphorus, arsenic or antimony atom, R represents a bivalent bridging group containing from 1-4 atoms in the bridge, R.sup.1 and R.sup.2 together represent a bivalent cyclic group whereby the two.cndot.free valencies are linked to M.sup.1, and R.sup.3 and R.sup.4 independently represent a hydrocarbyl group, or together represent a bivalent cyclic group whereby the two free valencies are linked to M.sup.Type: GrantFiled: July 23, 1998Date of Patent: November 30, 1999Assignee: Shell Oil CompanyInventors: Peter Arnoldy, Cornelis Mark Bolinger, Eit Drent, Jan J. Keijsper
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Patent number: 5986145Abstract: Cobalt or rhodium carbonyl compounds are removed from an aqueous solution of 3-hydroxypropanal by a process comprising the steps of:(a) contacting the 3-hydroxypropanal solution with oxygen under acidic conditions at a temperature within the range of about 5 to about 45.degree. C. to produce an oxidation product mixture comprising an aqueous solution of 3-hydroxypropanal, one or more water-soluble cobalt or rhodium species, and byproduct carbon monoxide;(b) removing byproduct carbon monoxide from the oxidation product mixture as it is generated; and(c) passing the oxidation product mixture in contact with an acidic ion exchange resin maintained at a temperature less than about 45.degree. C. and removing at least a portion of the soluble metal compounds from the oxidation product mixture.Type: GrantFiled: August 21, 1998Date of Patent: November 16, 1999Assignee: Shell Oil CompanyInventors: Joseph Broun Powell, Paul Richard Weider, Robert Lawrence Blackbourn, Stephen Blake Mullin
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Patent number: 5973174Abstract: A method is provided to prepare a cationic transition metal catalyst, the method including the steps of: providing a disubstituted phosphine selected from the group consisting of RPH and R.sub.1 R.sub.2 PH wherein R is a divalent group selected from substituted and nonsubstituted hydrocarbon groups, R.sub.1 and R.sub.2 are independently selected from substituted and nonsubstituted hydrocarbon groups; combining the disubstituted phosphine with a salt of the formula R.sub.3 X.sub.n wherein X is a good leaving group and is a weakly coordinating anion and R.sub.3 is a substituted or nonsubstituted aliphatic hydrocarbon and n is 1, 2, or 3 to form a phosphonium salt of a formula selected from R.sub.3 (RP.sup.+ H).sub.n nX.sup.- and R.sub.3 (R.sub.1 R.sub.2 P.sup.+ H).sub.n nX.sup.- ; and combining the phosphonium salt with a transition metal salt of the formula MY.sub.m wherein M is a transition metal, and Y is the anion of a weak acid thereby forming a cationic transition metal catalyst.Type: GrantFiled: November 24, 1998Date of Patent: October 26, 1999Assignee: Shell Oil CompanyInventors: Pui Kwan Wong, Manuel Soler Rodriguez, Andrew Allison Moxey
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Patent number: 5962744Abstract: A process comprising subjecting at least one compound containing at least one carbon--carbon double bond or at least one carbon--carbon triple bond, hydrogen and carbon monoxide, to a hydrocarbonylation reaction in supercritical carbon dioxide, in the presence of a Group VIII transition metal catalyst precursor, and a phosphite ligand.Type: GrantFiled: March 27, 1998Date of Patent: October 5, 1999Assignees: The Research Foundation of State University of New York, Mitsubishi Chemical CorporationInventors: Iwao Ojima, Hisao Urata
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Patent number: 5952530Abstract: This invention relates to a process for separating one or more products from a reaction product fluid comprising a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, a nonpolar solvent and said one or more products, wherein said process comprises (1) mixing said reaction product fluid with a polar solvent to obtain by phase separation a non-polar phase comprising said metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand and said nonpolar solvent and a polar phase comprising said one or more products and polar solvent, and (2) recovering said polar phase from said nonpolar phase; wherein said organophosphorus ligand has a partition coefficient between the nonpolar solvent and the polar solvent of greater than about 5, and said one or more products have a partition coefficient between the polar solvent and the nonpolar solvent of greater than about 0.5.Type: GrantFiled: February 2, 1998Date of Patent: September 14, 1999Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: John N. Argyropoulos, David Robert Bryant, Donald Lee Morrison, Kenneth Elwood Stockman
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Patent number: 5936130Abstract: A process for producing a rhodium complex solution, which comprises contacting an aqueous solution of a water-soluble rhodium compound and an organic solvent solution of a water-insoluble tertiary organic phosphorus compound, preferably in the presence of a C.sub.2-8 carboxylic acid, in a gas atmosphere containing carbon monoxide, followed by two phase separation, and recovering an organic solvent phase containing a rhodium-tertiary organic phosphorus compound complex.Type: GrantFiled: September 10, 1997Date of Patent: August 10, 1999Assignee: Mitsubishi Chemical CorporationInventors: Tomoyuki Mori, Masaki Takai, Tomohiko Inoue, Kazuyuki Yokoyama
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Patent number: 5932772Abstract: This invention relates to a process for separating one or more products from a reaction product fluid comprising a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, a polar solvent and said one or more products, wherein said process comprises (1) mixing said reaction product fluid with a nonpolar solvent to obtain by phase separation a polar phase comprising said metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand and said polar solvent and a nonpolar phase comprising said one or more products and nonpolar solvent, and (2) recovering said nonpolar phase from said polar phase; wherein said organophosphorus ligand has a partition coefficient between the polar solvent and the nonpolar solvent of greater than about 10, and said one or more products have a partition coefficient between the nonpolar solvent and the polar solvent of greater than about 0.5.Type: GrantFiled: February 2, 1998Date of Patent: August 3, 1999Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: John N. Argyropoulos, David Robert Bryant, Donald Lee Morrison, Kenneth Elwood Stockman, Anthony George Abatjoglou
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Patent number: 5929289Abstract: The present invention provides a hydroformylation process comprising: (1) forming a reaction mixture containing: (a) an olefinic compound, (b) hydrogen, (c) carbon monoxide, (d) a phosphite in which each phosphorus atom is bonded to three oxygen atoms and at least one such oxygen atom is bonded to a carbon atom of an aromatic ring that is adjacent to another carbon atom of said ring having a pendant monovalent group having a steric hindrance at least as great as the steric hindrance of the isopropyl group, (e) a catalytic amount of rhodium, and (f) a Group VIII metal (other than a rhodium) in an amount sufficient to reduce the rhodium-catalyzed decomposition of the phosphite during the hydroformylation process; and (2) maintaining the reaction mixture under conditions at which the olefinic compound reacts with the hydrogen and carbon monoxide to form an aldehyde.Type: GrantFiled: March 3, 1998Date of Patent: July 27, 1999Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Anthony George Abatjoglou, David Robert Bryant, John Michael Maher
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Patent number: 5919987Abstract: An industrial preparation of aldehydes and/or alcohols from olefins of more than 3 carbon atoms by a catalytic hydroformylation of the olefin reactant at a pressure of from 50 to 1000 bar and a temperature of from 50 to 180.degree. C. in the presence of an uncomplexed rhodium catalyst homogeneously dissolved in the reaction medium. The catalytic activity of the rhodium is maintained, first by extracting it from the initially discharged reaction mixture by means of an aqueous solution of a nitrogen-containing complexing agent such as sulfonated or carboxylated pyridines, quinolines or the like. In a recycle of the complexed rhodium to be reused in the hydroformylation reaction, the aqueous rhodium-containing extract is fed to a precarbonylation stage where it subjected to a required precarbonylation in the presence of an essentially water-insoluble organic liquid and in the presence of carbon monoxide, synthesis gas or another gas mixture containing carbon monoxide at from 50 to 1000 bar and from 50 to 180.Type: GrantFiled: September 13, 1996Date of Patent: July 6, 1999Assignee: BASF AktiengesellschaftInventors: Heinz-Josef Kneuper, Maik Aron, Frank-Michael Korgitzsch, Michael Nilles, Wolfgang Harder, Michael Roper, Rocco Paciello
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Patent number: 5917095Abstract: This invention relates to a process for separating one or more phosphorus acidic compounds from a reaction product fluid containing said one or more phosphorus acidic compounds, a metal-organophosphorus ligand complex catalyst and optionally free organophosphorus ligand which process comprises (a) treating said reaction product fluid with water sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said reaction product fluid and (b) treating the water which contains phosphorus acidic compounds removed from said reaction product fluid with an acid removal substance sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said water.Type: GrantFiled: March 11, 1997Date of Patent: June 29, 1999Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: David Robert Bryant, James Clair Nicholson, John Robert Briggs, Diane Lee Packett, John Michael Maher
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Patent number: 5910600Abstract: A bisphosphite compound of the following formula (A): ##STR1## wherein --Ar--Ar-- is a bisarylene group represented by any one of the formulae (A-I) to (A-III) defined in the specification, and each of Z.sub.1 to Z.sub.4 is a C.sub.4-20 aromatic or heteroaromatic group which may have a substituent, wherein each of substituents on carbon atoms of an aromatic ring adjacent to the carbon atom bonded to the oxygen atom in each of Z.sub.1 to Z.sub.4, is a C.sub.0-2 group, and each pair of Z.sub.1 and Z.sub.2, and Z.sub.3 and Z.sub.4, are not bonded to each other.Type: GrantFiled: April 28, 1997Date of Patent: June 8, 1999Assignee: Mitsubishi Chemical CorporationInventors: Hisao Urata, Hiroaki Itagaki, Eitaro Takahashi, Yasuhiro Wada, Yoshiyuki Tanaka, Yasukazu Ogino
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Patent number: 5892127Abstract: This invention relates in part to processes for selectively producing one or more substituted or unsubstituted 1,6-hexanedials, e.g., adipaldehyde, which comprise: (a) subjecting one or more substituted or unsubstituted alkadienes, e.g., butadiene, or a mixture comprising one or more substituted or unsubstituted alkadienes to hydroformylation in the presence of a hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and at an alkadiene partial pressure and/or a carbon monoxide partial pressure sufficient to selectively produce one or more substituted or unsubstituted pentenals or a reaction mixture comprising one or more substituted or unsubstituted pentenals; and (b) subjecting said one or more substituted or unsubstituted pentenals or said reaction mixture comprising one or more substituted or unsubstituted pentenals to hydroformylation in the presence of a hydroformylation catalyst, e.g.Type: GrantFiled: April 15, 1997Date of Patent: April 6, 1999Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Diane Lee Packett, John Robert Briggs, David Robert Bryant, Ailene Gardner Phillips
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Patent number: 5892119Abstract: This invention relates to a process for separating one or more phosphorus acidic compounds from a reaction product fluid containing said one or more phosphorus acidic compounds, a metal-organophosphorus ligand complex catalyst and optionally free organophosphorus ligand which process comprises (a) treating said reaction product fluid with water sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said reaction product fluid and (b) treating the water which contains phosphorus acidic compounds removed from said reaction product fluid with an ion exchange resin sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said water.Type: GrantFiled: March 11, 1997Date of Patent: April 6, 1999Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: David Robert Bryant, James Clair Nicholson, Ernst Billig, John Robert Briggs, Diane Lee Packett, John Michael Maher
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Patent number: 5886236Abstract: This invention relates in part to processes for producing one or more substituted or unsubstituted aldehyde acid salts, e.g., epsilon caprolactam, which comprises subjecting said one or more substituted or unsubstituted unsaturated acid salts, e.g., pentenoic acid salts, to hydroformylation in the presence of a hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce one or more substituted or unsubstituted aldehyde acid salts and/or one or more substituted or unsubstituted epsilon caprolactam precursors. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted aldehyde acid salts as the principal product(s) of reaction.Type: GrantFiled: April 15, 1997Date of Patent: March 23, 1999Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Thomas Carl Eisenschmid, John Robert Briggs, Diane Lee Packett, Kurt Damar Olson, John Michael Maher
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Patent number: 5886237Abstract: This invention relates in part to processes for selectively producing one or more substituted or unsubstituted alkenals. The process hydroformylates at least one substituted or unsubstituted alkadienes, e.g., butadiene, or a mixture of one or more substituted or unsubstituted alkadienes in the presence of a hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and at an alkadiene and/or carbon monoxide partial pressure sufficient to selectively produce at least one substituted or unsubstituted alkenals, e.g., pentenals. The substituted and unsubstituted alkenals produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof, e.g., hydrogenation to alkenols, particularly pentenols. This invention also relates to reaction mixtures containing one or more substituted or unsubstituted alkenals or alkenols as principal product(s) of those reactions.Type: GrantFiled: April 15, 1997Date of Patent: March 23, 1999Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Diane Lee Packett, John Robert Briggs, David Robert Bryant, Ailene Gardner Phillips
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Patent number: 5886235Abstract: This invention relates to a process for separating one or more phosphorus acidic compounds from a reaction product fluid containing said one or more phosphorus acidic compounds, a metal-organophosphorus ligand complex catalyst and optionally free organophosphorus ligand which process comprises treating said reaction product fluid with water sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said reaction product fluid.Type: GrantFiled: March 11, 1997Date of Patent: March 23, 1999Assignee: Union Carbide Chemicals & Plastics Technology Corporation.Inventors: David Robert Bryant, James Clair Nicholson, John Robert Briggs, Diane Lee Packett, John Michael Maher
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Patent number: 5880311Abstract: Catalyst particles are contacted with a liquid and a gas in a vertically extending cylindrical vessel. The particles and liquid are placed in the vessel into which the gas and liquid are continuously fed from the bottom thereof so that an upwardly flowing mixture comprising the particles, liquid and gas is formed. The mixture is introduced into a gas separating zone disposed adjacent to an upper portion of the vessel to separate the mixture by gravity into a gas phase, a supernatant liquid phase and a phase rich in the catalyst particles. The gas and supernatant phases are continuously withdrawn from the separating zone while the catalyst particles-rich phase is continuously recycled to the bottom of the vessel by gravity.Type: GrantFiled: March 30, 1995Date of Patent: March 9, 1999Assignee: Tonen CorporationInventors: Fumihiko Uemura, Hideki Sugiyama, Chieko Nagasawa, Takeshi Minami, Kazuhiko Hamato, Noriyuki Yoneda, Akihisa Yamaguchi
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Patent number: 5874638Abstract: A hydroformylation process for unsaturated compounds such as monoolefins and diolefins is carried out in an ionic medium in which the catalytic species is dissolved, but in which the reaction products (aldehydes) formed are only slightly soluble or are insoluble. The ionic medium is liquid at a temperature below 90.degree. C. and comprises at least one quaternary ammonium and/or phosphonium cation and at least one anion which is preferably selected from the group formed by tetrafluoroborate when the cation is ammonium, hexafluorophosphate, hexafluoroantimonate, hexafluoroarsenate, perfluoroalkylsulphonates, fluorosulphonate, bis-perfluoroalkylsulphonyl amides or dichlorocuprate, tetrachlorocuprate, tetrachloroaluminate, or trichlorozincate. At the end of the reaction, the organic phase is separated out and the polar phase containing the catalyst is used again.Type: GrantFiled: December 2, 1996Date of Patent: February 23, 1999Assignee: Institut Francais du PetroleInventors: Yves Chauvin, Helene Olivier, Lothar Mussmann
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Patent number: 5874639Abstract: This invention relates to a process which comprises reacting one or more reactants in the presence of a metal-organopolyphosphorus ligand complex catalyst and optionally free organopolyphosphorus ligand to produce a reaction product fluid comprising one or more products, wherein said process is conducted at a carbon monoxide partial pressure such that reaction rate increases as carbon monoxide partial pressure decreases and reaction rate decreases as carbon monoxide partial pressure increases and which is sufficient to prevent and/or lessen deactivation of the metal-organopolyphosphorus ligand complex catalyst.Type: GrantFiled: March 11, 1997Date of Patent: February 23, 1999Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: James Clair Nicholson, David Robert Bryant, James Russell Nelson, John Robert Briggs, Diane Lee Packett, John Michael Maher
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Patent number: 5874641Abstract: A hydroformylation catalyst composition comprising iridium or rhodium and a bidentate organic phosphite ligand wherein the two phosphorus atoms of the phopshite ligand are linked with a 2,2'-dihydroxyl-1,1'-binapthalene bridging group having the following structure (Q): ##STR1## in which R.sup.1 and R.sup.2 are substituents other than hydrogen.Type: GrantFiled: April 28, 1997Date of Patent: February 23, 1999Assignees: DSM N.V., E. I. du Pont de Nemours and CompanyInventors: Patrick M. Burke, James M. Garner, Wilson Tam, Kristina A. Kreutzer, Antonius J.J.M. Teunissen, Carina S. Snijder, Carolina B. Hansen
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Patent number: 5874640Abstract: This invention relates to a process for separating one or more phosphorus acidic compounds from a reaction product fluid containing said one or more phosphorus acidic compounds, a metal-organophosphorus ligand complex catalyst and optionally free organophosphorus ligand which process comprises treating said reaction product fluid with an aqueous buffer solution sufficient to neutralize and remove at least some amount of said one or more phosphorus acidic compounds from said reaction product fluid.Type: GrantFiled: March 11, 1997Date of Patent: February 23, 1999Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: David Robert Bryant, Tak Wai Leung, Ernst Billig, Thomas Carl Eisenschmid, James Clair Nicholson, John Robert Briggs, Diane Lee Packett, John Michael Maher
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Patent number: 5847228Abstract: The invention relates to a process for the hydroformylation of an olefin chosen from the alkenes represented by the formula CnH.sub.2n in which n is an integer less than or equal to 30, or chosen from functionalized olefins, by a CO/H.sub.2 gas mixture in a two-phase medium, this process consisting in placing in contact, on the one hand, an aqueous solution containing a catalytic system consisting of a water-soluble transition metal complex and a water-soluble phosphine, and, on the other hand, an olefin, in heating the reaction mixture obtained with stirring, after it has been placed under a pressure of the CO/H.sub.2 gas mixture, in which process a modified cyclodextrin is introduced into the aqueous solution containing the catalytic system.Type: GrantFiled: July 17, 1997Date of Patent: December 8, 1998Assignee: Centre National de la Recherche ScientifiqueInventors: Eric Monflier, Andre Mortreux, Yves Castanet
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Patent number: 5841003Abstract: An alkanediol such as 1,3-propanediol is prepared in a process which involves reacting an alkylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of a non-phosphine-ligated cobalt catalyst and a lipophilic ruthenium promoter to produce an intermediate product mixture containing a hydroxyalkanal in an amount less than 15 wt %; extracting the hydroxyalkanal from the intermediate product mixture into an aqueous liquid at a temperature less than about 100.degree. C. and separating the aqueous phase containing hydroxyalkanal from the organic phase containing cobalt catalyst; hydrogenating the hydroxyalkanal in the aqueous phase to an alkanediol; and recovering the alkanediol.The process enables the production of an alkanediol such as 1,3-propanediol in high yields and selectivity without the use of a phosphine ligand-modified cobalt catalyst.Type: GrantFiled: July 23, 1996Date of Patent: November 24, 1998Assignee: Shell Oil CompanyInventors: Lynn Henry Slaugh, Paul Richard Weider, Joseph Broun Powell
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Patent number: 5840993Abstract: The invention relates to cobalt carbonyl catalysts of the formula (I) ##STR1## where R is --CH(CH.sub.2 OCH.sub.2 CH.sub.3).sub.2 or --C.sub.2 H.sub.4 (OCH.sub.2 CH.sub.2).sub.n OY, with n=1 to 12 and Y=H or CH.sub.3, and also a process for their preparation and their use as hydroformylation catalysts.Type: GrantFiled: February 26, 1998Date of Patent: November 24, 1998Assignee: Hoechst AGInventors: Uwe Ritter, Norbert Winkhofer, Herbert Roesky
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Patent number: 5821389Abstract: This invention relates in part to processes for producing one or more substituted or unsubstituted hydroxyaldehydes, e.g., 6-hydroxyhexanals, which comprise subjecting one or more substituted or unsubstituted alkadienes, e.g., butadiene, to reductive hydroformylation in the presence of a reductive hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and hydroformylation in the presence of a hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce one or more substituted or unsubstituted hydroxyaldehydes. The substituted and unsubstituted hydroxyaldehydes produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof, e.g., epsilon caprolactone. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted hydroxyaldehydes as principal product(s) of reaction.Type: GrantFiled: April 15, 1997Date of Patent: October 13, 1998Assignee: Union Carbide Chemicals & Technology CorporationInventors: John Robert Briggs, Diane Lee Packett, David Robert Bryant, Ailene Gardner Phillips, David James Schreck, Kurt Damar Olson, Erik Bruce Tjaden, Anil Sakharam Guram, Thomas Carl Eisenschmid, Elaine Susan Brigham
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Patent number: 5817850Abstract: The synthesis of new sterically hindered ferrocene bis(phosphonites) of formula I ##STR1## the synthesis of the corresponding transition-metal complexes and the use of these complexes in transition-metal-catalyzed reactions are described.Type: GrantFiled: October 30, 1997Date of Patent: October 6, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Stephen D. Pastor, Sai P. Shum
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Patent number: 5817883Abstract: This invention relates in part to processes for producing one or more substituted or unsubstituted hydroxyaldehydes, e.g., 6-hydroxyhexanals, which comprise subjecting one or more substituted or unsubstituted alkadienes, e.g., butadiene, to hydrocarbonylation in the presence of a hydrocarbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and hydroformylation in the presence of a hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce one or more substituted or unsubstituted hydroxyaldehydes. The substituted and unsubstituted hydroxyaldehydes produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof, e.g., epsilon caprolactone. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted hydroxyaldehydes as principal product(s) of reaction.Type: GrantFiled: April 15, 1997Date of Patent: October 6, 1998Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: John Robert Briggs, Kurt Damar Olson, Erik Bruce Tjaden, Anil Sakharam Guram, Diane Lee Packett, Thomas Carl Eisenschmid, Elaine Susan Brigham
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Patent number: 5817884Abstract: A process for preparing aldehydes by hydroformylation of olefinically unsaturated compounds with hydrogen and carbon monoxide in a homogeneous phase in the presence of a catalyst system comprising organometallic complex compounds and ligands of these complex compounds in molar excess, and separating off the catalyst system from the hydroformylation reaction mixture by pressure filtration on a semipermeable membrane of an aromatic polyamide, the mass molar ratio of the ligands present in excess to the aldehydes prepared is 9-30, preferably 10-25, in particular 10-15, with the ligands present in excess not being alkylammonium or arylammonium salts of sulfonated, carboxylated or phosphonated aromatic diphosphines which by maintaining the molar mass ratio, not only are high activation and selectivity values obtained in the hydroformylation itself, but also excellent retention values for the catalyst system are obtained in the membrane filtration step.Type: GrantFiled: May 14, 1997Date of Patent: October 6, 1998Assignee: Hoechst AktiengesellschaftInventor: Helmut Bahrmann
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Patent number: 5811590Abstract: A process is provided for the hydroformylation of ethylenically unsaturated compounds having at least 4 carbon atoms by reaction thereof with carbon monoxide and hydrogen in the presence of a solvent and a catalyst system obtainable by combining:a) a source of Group VIII metal cations;b) a source of anions; andc) a source of phosphine ligands,wherein the solvent is a C.sub.1, to C.sub.10 alkane or alkene having two or more cyano groups attached.Type: GrantFiled: October 16, 1996Date of Patent: September 22, 1998Assignee: Shell Oil CompanyInventors: Peter Arnoldy, Arnoldus Maria Iping