Plural Stages Each Having Hydroformylation Patents (Class 568/453)
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Publication number: 20150133695Abstract: A process comprising contacting a reaction fluid, which contains at least one phosphorus acidic compound, with a buffer solution to neutralize at least some amount of the phosphorus acidic compound, wherein the buffer solution comprises at least one salt of an unsaturated aliphatic carboxylic acid.Type: ApplicationFiled: May 22, 2013Publication date: May 14, 2015Applicant: The Dow Chemical CompanyInventors: Michael A. Brammer, Rick B. Watson, Avery L. Watkins
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Patent number: 8389775Abstract: The invention relates to a process for preparing polyether alcohols, which comprises the steps a) reaction of an unsaturated natural oil or fat with a mixture of carbon monoxide and hydrogen, b) reaction of the mixture from step a) with hydrogen, c) reaction of the product from step b) with an alkylene oxide in the presence of a catalyst.Type: GrantFiled: January 26, 2009Date of Patent: March 5, 2013Assignee: BASF SEInventors: Darijo Mijolovic, Andrea Haunert, Andreas Kunst, Stephan Bauer, Qiang Miao, Berend Eling
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Patent number: 7615645Abstract: The invention relates to a method for the continuous production of aldehydes by the isomerising hydroformylation in a homogenous phase of olefin compositions by means of a synthesis gas, in the presence of a homogeneous rhodium catalyst that is complexed with an organophosphorus ligand containing oxygen atoms and/or nitrogen atoms and a free ligand. The production is carried out at high temperature and high pressure in a multi-stage reaction system consisting of at least two reaction zones. According to the method, the olefin composition is first reacted in a first reaction zone or a group of several first reaction zones at a total pressure of between 10 and 40 bar, using a synthesis gas with a CO/H2 molar ratio of between 4:1 and 1:2 until a 40 to 95% conversion of the ?-olefins is obtained.Type: GrantFiled: October 14, 2004Date of Patent: November 10, 2009Assignee: BASF AktiengesellschaftInventors: Martin Volland, Thomas Mackewitz, Wolfgang Ahlers, Ansgar Schäfer, Wolfgang Richter, Rocco Paciello
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Patent number: 7179947Abstract: A process for the catalytic hydroformylation of olefins having from 6 to 24 carbon atoms, in which the hydroformylation is carried out in one or more stage(s) and a mixture comprising at least one olefin and an aldehyde in a molar ratio of aldehyde to olefin of from 0.005:1 to 0.2:1 is used as feed in at least one of these stages which is carried out in the presence of an unmodified cobalt complex as catalyst.Type: GrantFiled: December 2, 2005Date of Patent: February 20, 2007Assignee: Oxeno Olefinchemie GmbHInventors: Hans-Gerd Lueken, Alfred Kaizik, Stefan Drees, Wilfried Bueschken, Wilhelm Droste
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Patent number: 6723884Abstract: Olefins having from 6 to 20 carbon atoms are hydroformylated by means of a continuous process in which a) an aqueous cobalt(II) salt solution is brought into intimate contact with hydrogen and carbon monoxide to form a hydroformylation-active cobalt catalyst, and the aqueous phase comprising the cobalt catalyst is brought into intimate contact with the olefins and, if desired, an organic solvent and also hydrogen and carbon monoxide in at least one reaction zone where the cobalt catalyst is extracted into the organic phase and the olefins are hydroformylated, b) the output from the reaction zone is treated with oxygen in the presence of acidic aqueous cobalt(II) salt solution, with the cobalt catalyst being decomposed to form cobalt(II) salts and these being backextracted into the aqueous phase; and the phases are subsequently separated, c) the aqueous cobalt(II) salt solution is recirculated in unchanged form to step a), wherein the cobalt(II) salt solution has a concentration of from 1.1 to 1.Type: GrantFiled: February 19, 2002Date of Patent: April 20, 2004Assignee: BASF AktiengesellschaftInventors: Armin Volker Grenacher, Hans Stepp
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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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Patent number: 6310260Abstract: This invention relates to a process for separating one or more organophosphorus ligand degradation products, one or more reaction byproducts and one or more products from a continuously generated reaction product fluid comprising one or more unreacted reactants, a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more organophosphorus ligand degradation products, said one or more reaction byproducts, said one or more products, one or more polar solvents and one or more nonpolar solvents by phase separation wherein (i) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more products is expressed by a partition coefficient ratio Ef1 which is a value greater than about 2.5, (ii) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more organophosphorus ligand degradation products is expressed by a partition coefficient ratio Ef2 which is a value greater than about 2.Type: GrantFiled: March 15, 2000Date of Patent: October 30, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: John Nicholas Argyropoulos, Jeffrey Scott Kanel, Michael Leo Tulchinsky, David James Miller, Donald Lee Morrison, Paul Foley, David Robert Bryant, Ailene Gardner Phillips, Brian Michael Roesch, John Robert Briggs, Max Min Lee, John Michael Maher
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Patent number: 6307108Abstract: This invention relates to a process for separating one or more organophosphorus ligand degradation products, one or more reaction byproducts and one or more formylester products from a reaction product fluid comprising one or more unreacted unsaturated ester reactants, a metal-organophoshorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more organophosphorus ligand degradation products, said one or more reaction byproducts, said one or more products, a nonpolar solvent and a polar solvent by phase separation wherein (i) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more products is expressed by a partition coefficient ratio Ef1 which is a value greater than about 2.5 (ii) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more organophosphorus ligand degradation products is expressed by a partition coefficient ratio Ef2 which is a value greater than about 2.Type: GrantFiled: March 15, 2000Date of Patent: October 23, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: John Nicholas Argyropoulos, Jeffrey Scott Kanel, Michael Leo Tulchinsky, David James Miller, Donald Lee Morrison, Paul Foley, David Robert Bryant
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Patent number: 6307110Abstract: This invention relates to a process for separating one or more organophosphorus ligand degradation products, one or more reaction byproducts and one or more products from a continuously generated reaction product fluid comprising one or more unreacted reactants, a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more organophosphorus ligand degradation products, said one or more reaction byproducts, said one or more products, one or more nonpolar solvents and one or more polar solvents by phase separation wherein (i) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more products is expressed by a partition coefficient ratio Ef1which is a value greater than about 2.5, (ii) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more organophosphorus ligand degradation products is expressed by a partition coefficient ratio Ef2 which is a value greater than about 2.Type: GrantFiled: March 15, 2000Date of Patent: October 23, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: John Nicholas Argyropoulos, Jeffrey Scott Kanel, Michael Leo Tulchinsky, David James Miller, Donald Lee Morrison, Paul Foley, David Robert Bryant, Ailene Gardner Phillips, Brian Michael Roesch, John Robert Briggs, Max Min Lee, John Michael Maher
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Patent number: 6307109Abstract: 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, said one or more products, one or more nonpolar reaction solvents and one or more polar reaction solvents, in which said reaction product fluid exhibits phase behavior depicted by FIG. 1, wherein said process comprises (1) supplying said reaction product fluid from a reaction zone to a separation zone, (2) controlling concentration of said one or more nonpolar reaction solvents and said one or more polar reaction solvents, temperature and pressure in said separation zone sufficient to obtain by phase separation two immiscible liquid phases depicted by regions 2, 4 and 6 of FIG. 1 comprising a polar phase and a nonpolar phase and to prevent or minimize formation of three immiscible liquid phases depicted by region 5 of FIG. 1 and one homogeneous liquid phase depicted by regions 1, 3 and 7 of FIG.Type: GrantFiled: March 15, 2000Date of Patent: October 23, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Jeffrey Scott Kanel, David Robert Bryant, Brian Michael Roesch, Ailene Gardner Phillips
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Patent number: 6303830Abstract: This invention relates to a process for separating one or more organophosphorus ligand degradation products, one or more reaction byproducts and one or more formylester products from a reaction product fluid comprising one or more unreacted unsaturated ester reactants, a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more organophosphorus ligand degradation products, said one or more reaction byproducts, said one or more products, a polar solvent and a nonpolar solvent by phase separation wherein(i) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more products is expressed by a partition coefficient ratio Ef1 which is a value greater than about 2.5, (ii) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more organophosphorus ligand degradation products is expressed by a partition coefficient ratio Ef2 which is a value greater than about 2.Type: GrantFiled: March 15, 2000Date of Patent: October 16, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: John Nicholas Argyropoulos, Jeffrey Scott Kanel, Michael Leo Tulchinsky, David James Miller, Donald Lee Morrison, Paul Foley, David Robert Bryant
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Patent number: 6303829Abstract: 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, said one or more products, one or more nonpolar reaction solvents and one or more polar reaction solvents, wherein said process comprises (1) subjecting said reaction product fluid to fractional countercurrent extraction with at least two immiscible extraction solvents, said at least two immiscible extraction solvents comprising at least one nonpolar extraction solvent and at least one polar extraction solvent, to obtain a nonpolar phase comprising said metal-organophosphorus ligand complex catalyst, said optionally free organophosphorus ligand, said one or more nonpolar reaction solvents and said at least one nonpolar extraction solvent and a polar phase comprising said one or more products, said one or more polar reaction solvents and said at least one polar extraction solvent, and (2) recovering said polarType: GrantFiled: March 15, 2000Date of Patent: October 16, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Jeffrey Scott Kanel, John Nicholas Argyropoulos, Ailene Gardner Phillips, Brian Michael Roesch, John Robert Briggs, Max Min Lee, John Michael Maher, David Robert Bryant
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Patent number: 6294700Abstract: 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, said one or more products, one or more polar reaction solvents and one or more nonpolar reaction solvents, wherein said process comprises (1) subjecting said reaction product fluid to fractional countercurrent extraction with at least two immiscible extraction solvents, said at least two immiscible extraction solvents comprising at least one polar extraction solvent and at least one nonpolar extraction solvent, to obtain a polar phase comprising said metal-organophosphorus ligand complex catalyst, said optionally free organophosphorus ligand, said one or more polar reaction solvents and said at least one polar extraction solvent and a nonpolar phase comprising said one or more products, said one or more nonpolar reaction solvents and said at least one nonpolar extraction solvent, and (2) recovering said nonpoType: GrantFiled: March 15, 2000Date of Patent: September 25, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Jeffrey Scott Kanel, John Nicholas Argyropoulos, Ailene Gardner Phillips, Brian Michael Roesch, John Robert Briggs, Max Min Lee, John Michael Maher, David Robert Bryant
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Patent number: 5481044Abstract: .alpha.-alkyl aldehydes having 8 to 17 carbon atoms are obtained from terminal olefins containing one less carbon atom. The olefins are first isomerized in the presence of iron carbonyl and then, without separating out the iron compound, hydroformylated in the presence of rhodium as catalyst.Type: GrantFiled: December 15, 1994Date of Patent: January 2, 1996Assignee: Hoechst AktiengesellschaftInventors: Jurgen Weber, Helmut Springer
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Patent number: 5476968Abstract: A N,N'-bis(p-hydroxymethylphenyl)benzidine compound having the following formula (I): ##STR1## wherein R.sub.1 represents a hydrogen atom, a methyl group or a methoxy group; R.sub.2 represents an alkyl group having one to four carbon atoms, a methoxy group or an ethoxy group; and R.sub.3 represents a hydrogen atom or a methyl group, is intended to be used as a charge transporting material of an electrophotographic photoreceptor. A method for preparing the compound includes formylating a N,N'-diphenylbenzidine derivative having the following formula (II): ##STR2## by the conventional Viismeier reaction to obtain a N,N'-bis(p-formylphenyl) benzidine derivative of the following formula (III): ##STR3## and reducing the derivative with a boron hydride salt or an aluminum hydride salt.Type: GrantFiled: August 22, 1994Date of Patent: December 19, 1995Assignee: Fuji Xerox Co., Ltd.Inventors: Akira Imai, Katsumi Nukada
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Patent number: 5462986Abstract: Mixtures of isomeric decyl alcohols prepared by hydroformylation of mixtures of butene-1 and butene-2 in two stages to give aldehyde mixtures, and condensation of the aldehyde mixtures to form an aldol mixture, followed by separation and hydrogenation. The first stage of the hydroformylation proceeds in the presence of rhodium catalysts dissolved in water, the second stage in the presence of cobalt catalysts homogeneously dissolved in the reaction medium. The mixture of isomeric decyl alcohols, when esterified with phthalic acid, yields a mixture of isomeric decyl phthalates which are useful as plasticizers.Type: GrantFiled: February 14, 1995Date of Patent: October 31, 1995Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Wolfgana Greb, Peter Heymanns, Peter Lappe, Thomas Muller, Jurgen Szameitat, Ernst Wiebus
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Patent number: 5463147Abstract: Mixtures of isomeric decyl alcohols prepared by hydroformylation of mixtures of butene-1 and butene-2 in two stages to give aldehyde mixtures, and condensation of the aldehyde mixtures to form an aldol mixture, followed by separation and hydrogenation. The first stage of the hydroformylation proceeds in the presence of rhodium catalysts dissolved in water, the second stage in the presence of cobalt catalysts homogeneously dissolved in the reaction medium. The mixture of isomeric decyl alcohols, when esterified with phthalic acid, yields a mixture of isomeric decyl phthalates which are useful as plasticizers.Type: GrantFiled: September 23, 1994Date of Patent: October 31, 1995Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Wolfgang Greb, Peter Heymanns, Peter Lappe, Thomas Muller, Jurgen Szameitat, Ernst Wiebus
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Patent number: 5426238Abstract: A method for producing an aldehyde, which comprises reacting an olefin with carbon monoxide and hydrogen in a hydroformylation reaction zone in the presence of a rhodium catalyst having an organophosphorus compound as a ligand, wherein a reaction solution withdrawn from the hydroformylation reaction zone, which contains an unreacted olefin, an aldehyde product and the catalyst, is countercurrently contacted with carbon monoxide and hydrogen in a contact tower to separate and recover the unreacted olefin without substantially deactivating the rhodium catalyst and supplying the recovered unreacted olefin together with the carbon monoxide and the hydrogen to the hydroformylation reaction zone.Type: GrantFiled: May 26, 1994Date of Patent: June 20, 1995Assignee: Mitsubishi Kasei CorporationInventors: Tomoyuki Mori, Akio Ueda, Kouichi Fujita
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Patent number: 5410091Abstract: An improved process for the hydroformylation of olefins with carbon monoxide and hydrogen in the presence of a hydroformylation catalyst in a continuous tubular reactor, the improvement comprising:a. employing an rhodium hydroformylation catalyst;b. maintaining the reaction temperature at less than about 145.degree. C.; andc. maintaining the pressure at less than 450 psig and the partial pressure therein attributable to carbon monoxide no greater than about 90% of the total pressure;whereby the hydroformylated olefin product is rich in normal aldehydes.Type: GrantFiled: June 2, 1994Date of Patent: April 25, 1995Assignee: Quimica Oxal C.A.Inventor: Charles S. Nall
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Patent number: 5367106Abstract: In a primary process for hydroformylating olefins in the presence of a rhodium-containing catalyst solution to produce aldehydes and a gaseous effluent comprising unreacted olefin is vented, the improvement which comprises employing the effluent as a reactant feed for a coupled secondary hydroformylation process conducted jointly therewith in which the catalyst solution is cycled back and forth between the primary and secondary hydroformylation processes.Type: GrantFiled: September 20, 1993Date of Patent: November 22, 1994Assignee: Hoechst Celanese CorporationInventors: Jerry D. Unruh, Wendell L. Pieper, Milo C. Pass
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Patent number: 5362917Abstract: A method for controlling a hydroformylation reaction for producing an aldehyde by subjecting an olefin, a feed oxo gas containing hydrogen and carbon monoxide, and a recycled gas withdrawn from a reactor and returned to the reactor, to a hydroformylation reaction in the reactor in the presence of a catalyst, which comprises:setting out a target value for the partial pressure of carbon monoxide in the reaction system to control the hydroformylation reaction;detecting the partial pressure of carbon monoxide corresponding to the target value; andcomparing the detected partial pressure of carbon monoxide with the target value to adjust a flow rate of a discharged gas from the reactor; orcomparing the detected partial pressure of carbon monoxide with the target value to adjust a flow rate of the feed oxo gas.Type: GrantFiled: September 24, 1993Date of Patent: November 8, 1994Assignee: Mitsubishi Kasei CorporationInventors: Morimasa Ogawa, Genichi Emoto, Akio Ueda, Takao Kibayashi, Keitaro Nakata, Tsuneo Inoue
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Patent number: 5336473Abstract: An apparatus for removing cobalt values from the crude product of a cobalt-catalyzed hydroformylation reaction wherein an overhead stripper-reactor reflux product is recycled to a location on the stripper-reactor which is capable of forming a stripping zone in the upper portion of the stripper-reactor and a reaction zone in the lower portion of the stripper-reactor.Type: GrantFiled: May 11, 1993Date of Patent: August 9, 1994Assignee: Exxon Chemical Patents Inc.Inventors: Kirk C. Nadler, Thomas R. Broussard, Joseph K. Pitre
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Patent number: 5105018Abstract: A process for hydroformylation of an olefin, which comprises reacting an olefin with carbon monoxide and hydrogen in the presence of a rhodium catalyst having a trivalent organic phosphorus compound as a ligand, wherein the hydroformylation reaction is conducted by two stage reactor systems i.e., a first stage reactor system comprising a reactor or reactors having a mixing characteristic of the liquid phase being substantially of complete mixing type, and a second stage reactor system being a reaction system of a catalyst solution circulating type and comprising a reactor or reactors having a mixing characteristic of piston flow type wherein when the mixing characteristic of the liquid phase is represented by a diffusion model, a non-dimensional number U (hereafter referred to as a "flow mixing parameter") defined by the formula (I):U.tbd.uL/2E (I)wherein u is an average flow velocity (cm/sec), L is the length (cm) of the reaction layer, and E is an average diffusion coefficient (cm.sup.Type: GrantFiled: October 12, 1990Date of Patent: April 14, 1992Assignee: Mitsubishi Kasei CorporationInventors: Chihiro Miyazawa, Hiroshi Mikami
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Patent number: 4390729Abstract: Complexes of the formula[(R.sub.2 DQ).sub.b P.sup.+ R.sup.1.sub.4-b ].sub.g.(MX.sub.n).sub.sare disclosed in which R is selected from an alkyl group containing 1 to 30 carbon atoms and an aryl group containing from 6 to 10 carbon atoms; Q is a divalent organic radical selected from an alkylene group and an alkylene group the carbon chain of which is interrupted by an ether oxygen or phenylene group, wherein the alkylene group contains from 1 to 30 carbon atoms; R.sup.1 represents an alkyl group containing from 1 to 30 carbon atoms, wherein said R.sup.1 groups can be the same or different; D is a member selected from P and N; Z.sup.- is an anion; M is a Group VIII metal; X is an anion or organic ligand satisfying the coordination sites of the metal; b times g is 1 to 6; n is 2 to 6; and s is 1 to 3. Processes of using such complexes are also disclosed.Type: GrantFiled: November 3, 1980Date of Patent: June 28, 1983Assignee: Exxon Research and Engineering Co.Inventor: Alexis A. Oswald
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Patent number: 4210426Abstract: A process for recovering propene and propene/propane mixtures from the off-gases obtained from the hydroformylation of propene involves contacting the off-gases with a liquid absorbent comprising at least one of the liquid substances formed during the hydroformylation of propene to absorb the propene and propane and thereafter desorbing these gases from said liquid substances.Type: GrantFiled: November 7, 1978Date of Patent: July 1, 1980Assignee: Chemische Werke Huls AktiengesellschaftInventor: Srinivasan Sridhar