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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Patent number: 8791305Abstract: The present invention relates to ligands and catalyst systems for the hydroformylation of short and long chain olefins, preferably for the hydroformylation of ally alcohol producing 4-hydroxybutyraldehyde. The ligands disclosed herein are all-trans phosphinomethyl-cyclobutane ligands, such as, for example, all-trans-1,2,3,4-tetra[bis-(3,5-xylyl)phosphinomethyl]-cyclobutane. The catalyst systems comprise these all-trans phosphinomethyl-cyclobutane ligands in combination with an organometallic rhodium complex such as, e.g., (acctylacetonato)-dicarbonyl-rhodium (I). The ligands and catalyst systems of the present invention may be employed in the hydroformylation of olefins, in particular in the hydroformylation of allylalcohol, and provide improved selectivity and high reaction yields.Type: GrantFiled: May 25, 2012Date of Patent: July 29, 2014Assignee: Umicore AG & Co. KGInventor: Dieter Arlt
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Patent number: 8779211Abstract: A process for producing 4-hydroxybutyraldehyde comprises reacting allyl alcohol with CO/H2 in a reactor in the presence of a catalyst system comprising rhodium complex and trans-1,2-bis[bis(3,5-di-n-alkylphenyl)phosphino]-cyclobutane at a pressure of about 50 psi or lower.Type: GrantFiled: May 29, 2013Date of Patent: July 15, 2014Assignee: Lyondell Chemical Technology, L.P.Inventors: Beaven S. Mandimutsira, Daniel F. White
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Patent number: 8741173Abstract: A combination of calixarene bisphosphite ligand and an organophosphine ligand. The combination can be employed with a catalytic metal to form a complex catalyst. The catalyst can be employed in ahydroforaiylation process for producing a mixture of aldehydes.Type: GrantFiled: September 21, 2011Date of Patent: June 3, 2014Inventors: Michael A. Brammer, Richard W. Wegman
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Patent number: 8710276Abstract: Disclosed are a catalyst composition for hydroformylation of olefin compounds, comprising a specific phosphine ligand and a transition metal catalyst, and a hydroformylation process using the same. Through a hydroformylation process using the catalyst composition according to the present invention, a suitable selectivity of iso-aldehyde can be maintained, catalyst stability can be improved, the amount of used ligand can be reduced and superior catalyst activity can be obtained.Type: GrantFiled: July 24, 2013Date of Patent: April 29, 2014Assignee: LG Chem, Ltd.Inventors: Dong Hyun Ko, Sung Shik Eom, O Hak Kwon, Hye Won Yang, Jae Hui Choi
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Patent number: 8710275Abstract: Modification of a unique supramolecular assembly of a pyridylphosphine ligand and a metal centered porphyrin complex is shown to give unprecedented selectivities to branched aldehydes via rhodium catalyzed hydroformylation of propylene and 1-octene. Use of magnesium in the porphyrin center provides the highest reported concentrations of iso-butyraldehyde and 2-methyl-octanal.Type: GrantFiled: May 31, 2012Date of Patent: April 29, 2014Assignee: Eastman Chemical CompanyInventors: David William Norman, Joost Nicolaas Hendrik Reek, Tatiana Renee Marie-Louise Besset
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Publication number: 20140114090Abstract: The present invention relates to ligands and catalyst systems for the hydroformylation of short and long chain olefins, preferably for the hydroformylation of ally alcohol producing 4-hydroxybutyraldehyde. The ligands disclosed herein are all-trans phosphinomethyl-cyclobutane ligands, such as, for example, all-trans-1,2,3, 4-tetra[bis-(3,5-xylyl)phosphinomethyl]-cyclobutane. The catalyst systems comprise these all-trans phosphinomethyl-cyclobutane ligands in combination with an organometallic rhodium complex such as, e.g., (acctylacetonato)-dicarbonyl-rhodium (I). The ligands and catalyst systems of the present invention may be employed in the hydroformylation of olefins, in particular in the hydroformylation of allylalcohol, and provide improved selectivity and high reaction yields.Type: ApplicationFiled: May 25, 2012Publication date: April 24, 2014Applicant: UMICORE AG & CO. KGInventor: Dieter Arlt
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Patent number: 8692027Abstract: Use of a unique supramolecular assembly of a pyridylphosphine ligand and a metal centered porphyrin complex is shown to give unprecedented selectivities to branched aldehydes via rhodium catalyzed hydroformylation of unsubstituted linear alpha-olefins such as propylene and 1-octene. Increasing the syngas pressure is shown to have a beneficial effect on branched aldehyde selectivity as is increasing the ratio of carbon monoxide to hydrogen used in the hydroformylation reaction.Type: GrantFiled: May 31, 2012Date of Patent: April 8, 2014Assignee: Eastman Chemical CompanyInventors: David William Norman, Joost Nicolaas Hendrik Reek, Tatiana Renee Marie-Louise Besset
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Patent number: 8680302Abstract: Disclosed is a practical method for efficiently producing an alcohol compound by hydrogenating an aldehyde by using a homogeneous copper catalyst which is an easily-available low-cost metal species. Specifically disclosed is a method for producing an alcohol compound, which is characterized in that a hydrogenation reaction of an aldehyde compound is performed in the presence of a homogeneous copper catalyst and a diphosphine compound.Type: GrantFiled: December 11, 2008Date of Patent: March 25, 2014Assignee: Takasago International CorporationInventor: Hideo Shimizu
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Publication number: 20140081050Abstract: Allyl alcohol, particularly from biobased sources such as glycerol, is hydroformylated to products including 4-hydroxybutyraldehyde and 4-hydroxy-2-methylpropionaldehyde by forming a homogeneous reaction mixture including allyl alcohol, a rhodium-based hydroformylation catalyst and a near critical liquefiable petroleum gas or mixture of such gases, reacting the near critical liquefiable petroleum gas (or gas mixture)-expanded allyl alcohol substrate with carbon monoxide and with hydrogen in the presence of the catalyst, and recovering substantially all of the petroleum gas or gases overhead by reducing the pressure and degassing the product mixture. Dense propane is especially useful as a single inert solvent/diluent, and substantially no other solvent/diluent is needed.Type: ApplicationFiled: February 14, 2012Publication date: March 20, 2014Applicant: THE UNIVERSITY OF KANSASInventors: Bala Subramaniam, Raghunath V. Chaudhari, Bibhas R. Sarkar
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Patent number: 8664451Abstract: Control of an in-series, multiple, e.g., two, reaction zone, hydroformylation process for producing normal (N) and iso (I) aldehydes at a N:I ratio, the process comprising contacting an olefinically unsaturated compound, e.g., propylene, with carbon monoxide, hydrogen and a catalyst comprising (A) a transition metal, e.g., rhodium, (B) an organobisphosphite, and (C) an organomonophosphite ligand, the contacting conducted in first and subsequent reaction zones and at hydroformylation conditions comprising an olefinically unsaturated compound partial pressure in each zone, the control exercised by decreasing the olefinically unsaturated compound partial pressure in the first reaction zone to decrease the N:I ratio or increasing the olefinically unsaturated compound partial pressure in the first reaction zone to increase the N:I ratio.Type: GrantFiled: December 15, 2010Date of Patent: March 4, 2014Assignee: Dow Technology Investments LLCInventors: Thomas C. Eisenschmid, Glenn A. Miller, Jeffrey S. Sawrey, Michael A. Brammer
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Publication number: 20140005440Abstract: A process for producing 4-hydroxybutyraldehyde comprises reacting allyl alcohol with CO/H2 in a reactor in the presence of a catalyst system comprising rhodium complex and trans-1, 2-bis[bis(3, 5-di-n-alkylphenyl)phosphino]-cyclobutane at a pressure of about 50 psi or lower.Type: ApplicationFiled: May 29, 2013Publication date: January 2, 2014Inventors: Beaven S. Mandimutsira, Daniel F. White
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Patent number: 8598389Abstract: A method of controlling a hydroformylation process for producing normal (N) and iso (I) aldehydes at a N:I ratio, the process comprising contacting an olefinically unsaturated compound, e.g., propylene, with synthesis gas and a catalyst comprising a transition metal, e.g., rhodium, and an organopolyphosphite and an organomonophosphite ligand, the contacting conducted at hydroformylation conditions comprising a synthesis gas partial pressure, the method comprising increasing the synthesis gas partial pressure in the first reaction zone to decrease the N:I ratio or decreasing the synthesis gas partial pressure in the first reaction zone to increase the N:I ratio.Type: GrantFiled: December 15, 2010Date of Patent: December 3, 2013Assignee: Dow Technology InvestmentsInventors: Thomas C. Eisenschmid, Jeffrey S. Sawrey, Glenn A. Miller, Michael A. Brammer
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Patent number: 8598390Abstract: A method of controlling an in-series, multiple, e.g., two, reaction zone, hydroformylation process for producing normal (N) and iso (I) aldehydes at a N:I ratio, the process comprising contacting an olefinically unsaturated compound with synthesis gas and a catalyst comprising (A) a transition metal, e.g., rhodium, (B) an organobisphosphite ligand, and (C) an organomonophosphite ligand, the contacting conducted in first and subsequent reaction zone(s) and at hydroformylation conditions comprising a transition metal concentration in each zone, the method comprising decreasing the transition metal concentration in the first reaction zone to decrease the N:I ratio or increasing the transition metal concentration in the first reaction zone to increase the N:I ratio.Type: GrantFiled: December 15, 2010Date of Patent: December 3, 2013Assignee: Dow Technology Investments LLCInventors: Thomas C. Eisenschmid, Jeffrey S. Sawrey, Glenn A. Miller, Michael A. Brammer
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Publication number: 20130317256Abstract: Disclosed are a catalyst composition for hydroformylation of olefin compounds, comprising a specific phosphine ligand and a transition metal catalyst, and a hydroformylation process using the same. Through a hydroformylation process using the catalyst composition according to the present invention, a suitable selectivity of iso-aldehyde can be maintained, catalyst stability can be improved, the amount of used ligand can be reduced and superior catalyst activity can be obtained.Type: ApplicationFiled: July 24, 2013Publication date: November 28, 2013Applicant: LG CHEM, LTD.Inventors: Dong Hyun KO, Sung Shik EOM, O Hak KWON, Hye Won YANG, Jae Hui CHOI
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Patent number: 8586800Abstract: A gas phase catalytic hydroformylation process for producing at least one aldehyde product in the presence of a transition metal-ligand complex hydroformylation catalyst and water vapor. Surprisingly, catalyst activity can be sustained by having traces of water vapor in the feed stream. Additionally, additional ligand can be added to replace lost ligand to maintain activity. In addition, it has been found that treatment of the catalyst with a buffer can rejuvenate catalyst activity.Type: GrantFiled: October 6, 2010Date of Patent: November 19, 2013Inventor: Richard W. Wegman
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Publication number: 20130274525Abstract: The present invention relates to a method of supplementing the catalyst in continuous hydroformylation during ongoing operation.Type: ApplicationFiled: April 11, 2013Publication date: October 17, 2013Applicant: BASF SEInventors: Edgar Zeller, Armin Ulonska, Arthur Höhn, Volker Uhrig, Rene Magnie, Reimund Fattler
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Publication number: 20130261344Abstract: The extraction process for removing metal salts from an organic hydroformylation reaction fluid (“HRF”) prior to returning the HRF to a reaction zone of a hydroformylation process, the extraction process comprising the step of contacting the HRF with an aqueous buffer solution, is improved by contacting the HRF with water in addition to that present in the aqueous buffer solution, i.e., with added water.Type: ApplicationFiled: November 3, 2011Publication date: October 3, 2013Inventors: Glenn A. Miller, Michael A. Brammer, Donald L. Campbell, JR., Thomas C. Eisenschmid, Adrian Lord, Jens Rudolph, Hans-Rüdiger Reech, Hans-Günter Thelen, Maximilian Walter
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Patent number: 8541627Abstract: An improved hydroformylation catalyst cycle is disclosed wherein the cobalt catalyst is recycled to the hydroformylation reaction mainly as a water soluble carbonyl salt, obtained from extraction of the acidic form of the homogeneous cobalt carbonyl catalyst from the hydroformylation product with an aqueous solution of a salt of a weaker acid. The organic product after extraction is submitted to a further demetalling step in the presence of a dilute acid and an oxidant. The water from this further demetalling step is suitable for use in the upstream extraction step. A free water phase present in the hydroformylation reaction product may be separated upstream from the extraction step and is suitable for use in the further demetalling step, such that the catalyst cycle has no waste water stream.Type: GrantFiled: August 19, 2009Date of Patent: September 24, 2013Assignee: ExxonMobil Chemical Patents Inc.Inventors: Eddy T. A. Van Driessche, Ronald D. Garton, Corey W. Reed
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Patent number: 8513468Abstract: A process for removing degradation acids from a catalyst solution comprising a phosphorus-containing hydroformylation ligand used in a hydroformylation reaction is described. The process involves using a supported epoxy compound. Also described is a hydroformylation process that includes the degradation acids removal process.Type: GrantFiled: December 30, 2010Date of Patent: August 20, 2013Assignee: Eastman Chemical CompanyInventor: Yun-Shan Liu
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Patent number: 8513469Abstract: A continuous hydroformylation process for producing at least one aldehyde product by utilizing a transition metal and a ligand mixture comprising an organopolyphosphite and an organomonophosphine, with improved stability of the organopolyphosphite ligand. The process involves reacting one or more olefinically-unsaturated compounds with carbon monoxide and hydrogen in the presence of an organopolyphosphite ligand and an organomonophosphine ligand, at least one of such ligands being bonded to a transition metal to form a transition metal-ligand complex hydroformylation catalyst. Surprisingly the addition of the organomonophosphine to a Rh/organopolyphosphite catalyst system did not result in a significant loss of reaction rate.Type: GrantFiled: December 10, 2009Date of Patent: August 20, 2013Inventor: Michael A. Brammer
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Patent number: 8507731Abstract: A process for hydroformylating an ?-olefin to produce two or more aldehydes comprising a normal aldehyde and one or more iso-aldehydes with a target molar ratio of the normal aldehyde to one or more iso-aldehydes in a selectable range from 3/1 to 60/1. The process uses a transition metal-ligand complex catalyst comprising a symmetric calixarene bisphosphite ligand. The target N/I ratio is selected by controlling carbon monoxide partial pressure.Type: GrantFiled: August 11, 2009Date of Patent: August 13, 2013Inventor: Michael A. Brammer
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Publication number: 20130204024Abstract: A combination of calixarene bisphosphite ligand and an organophosphine ligand. The combination can be employed with a catalytic metal to form a complex catalyst. The catalyst can be employed in a hydroforaiylation process for producing a mixture of aldehydes.Type: ApplicationFiled: September 21, 2011Publication date: August 8, 2013Applicant: DOW TECHNOLOGY INVESTMENTS LLCInventors: Michael A. Brammer, Richard W. Wegman
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Patent number: 8466306Abstract: A compound comprising a sulfonated dihydrocarbyl(arylalkyl)phosphine of formula R1R2PR3—(SO3M)n, wherein the R1 and R2 are selected individually from alkyl, aralkyl, and alicyclic groups, and R3 is a divalent or polyvalent arylalkylene radical such that the alkyl moiety is bonded to the phosphorus atom and the aryl moiety is bonded to the alkyl and is also substituted with one or more sulfonate groups; M is a monovalent cation, and n ranges from 1 to 3. The compound is useful as a ligand in transition metal-ligand complex catalysts that are capable of catalyzing the hydroformylation of an olefinically-unsaturated compound with carbon monoxide and hydrogen to form one or more corresponding aldehyde products. The ligand is incapable of alkyl-aryl exchange, thereby leading to reduced ligand usage and improved ligand and transition metal, e.g., rhodium, recovery and recycling.Type: GrantFiled: January 9, 2009Date of Patent: June 18, 2013Assignee: Dow Global Technologies LLCInventors: Michael L. Tulchinsky, Ronald R. Peterson
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Patent number: 8461394Abstract: A process for preparing a C5 aldehyde mixture from a hydrocarbon mixture comprising at least one linear butene by terminal hydroformylation under isomerizing conditions, using a catalyst system comprising rhodium, a bisphosphite ligand, and an amine.Type: GrantFiled: April 28, 2009Date of Patent: June 11, 2013Assignee: Evonik Oxeno GmbHInventors: Hans-Gerd Lueken, Dirk Fridag, Udo Lenz, Hermann-Josef Schulte-Althoff, Klaus-Diether Wiese, Alfred Kaizik, Patrick Muhlack, Wilfried Bueschken, Frank Hoeper
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Patent number: 8445728Abstract: The invention relates to a method for reprocessing a liquid product of a hydroformylation reaction, wherein the liquid phase produced in a release stage is supplied to a separating device from which a liquid flow containing rhodium is guided away via a filter, where solids thereby separated are taken out of the process and the filtrate obtained is guided back into the hydroformylation reaction.Type: GrantFiled: March 18, 2010Date of Patent: May 21, 2013Assignee: Oxea GmbHInventors: Wolfgang Greb, Rainer Lukas, Klaus Schmid, Wolfgang Zgorzelski, Jörg Arnold
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Patent number: 8426651Abstract: The present invention relates to a catalyst composition for hydroformylation and a method for preparing aldehydes using the same, wherein the catalyst composition for hydroformylation comprises: a triaryl phosphine ligand; a phosphine oxide or phosphine sulfide ligand having a specific chemical formula; and a transition metal catalyst. The catalyst composition provides high catalyst activity and stability and selectivity to normal aldehydes when used in the hydroformylation for preparing aldehydes from olefins.Type: GrantFiled: April 22, 2011Date of Patent: April 23, 2013Assignee: LG Chem, Ltd.Inventors: Jae Hui Choi, Dong Hyun Ko, Sung Shik Eom, Moo Ho Hong, O Hark Kwon, Dae Chul Kim
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Patent number: 8404902Abstract: The invention relates to a method for separating 1-butene from C4-containing hydrocarbon mixtures, comprising isobutene and 1-butene, by hydroformylation, wherein the catalytic system used is made of one of the transition metals of the group 8 to 10, preferably rhodium, and a bisphosphite ligand of the formula (I), where X is a divalent substituted or unsubstituted bisalkylene or bisarylene group having one or more heteroatom(s), Y is a divalent substituted or unsubstituted bisarylene or bisalkylene group having one or more heteroatom(s), Z is oxygen or NR9, and R1, R2, R3, R4 are identical or different, substituted or unsubstituted, linked, unlinked or condensed aryl or heteroaryl groups, and R9 is hydrogen or a substituted or unsubstituted alkyl or aryl group having one or more heteroatom(s), wherein the bisphosphite ligand of the formula (I) is used in an excess of a molar ratio of 100:1 to 1:1 to the transition metal, and that with a 1-butene conversion of more than 95% less than 5% of the present isobuteType: GrantFiled: April 28, 2009Date of Patent: March 26, 2013Assignee: Evonik Oxeno GmbHInventors: Burkard Kreidler, Klaus-Diether Wiese, Dieter Hess, Detlef Selent, Armin Boerner
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Patent number: 8404903Abstract: A process of controlling heavies in a recycle catalyst stream, particularly, for use in a continuous hydroformylation process of converting an olefin with synthesis gas in the presence of a hydroformylation catalyst to form an aldehyde product stream with subsequent separation of the catalyst for recycle to the hydroformylation step. Heavies are controlled, and preferably reduced, by means of feeding a recycle gas stream, taken as a portion of an over-head stream from a condenser, back to a vaporizer wherein the aldehyde product stream is separated.Type: GrantFiled: July 2, 2009Date of Patent: March 26, 2013Assignees: Dow Technology Investments, LLC, BASF SEInventors: Irvin B. Cox, Thomas C. Eisenschmid, Ronald R. Peterson, Rainer Papp, Ludwig Herk, Anthony G. Abatjoglou
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Patent number: 8394978Abstract: A compound comprising a sulfonated triorganophosphine of formula R1R2PR3[SO3M)]n, wherein R1 and R2 are selected individually from alkyl, aralkyl, and alicyclic groups; wherein R3 represents a branched divalent or polyvalent, alkylene or alicyclic radical that is bonded to the phosphorus atom and to one or more sulfonate substituents, and further wherein R3 does not contain any aryl moieties; M represents a monovalent cation; and n is an integer representing a total number of sulfonated substituents. The compound is useful as a ligand in transition metal-ligand complex catalysts that are capable of catalyzing the hydroformylation of an olefinically-unsaturated compound with carbon monoxide and hydrogen to form one or more corresponding aldehyde products. The ligand is incapable of alkyl-aryl exchange, thereby leading to reduced ligand usage and improving ligand and transition metal, e.g., rhodium, recovery and recycling, as compared with prior art ligands.Type: GrantFiled: January 9, 2009Date of Patent: March 12, 2013Assignee: Dow Global Technologies LLCInventors: Michael L. Tulchinsky, Anthony G. Abatjoglou
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Publication number: 20120259142Abstract: A method of controlling an in-series, multiple, e.g., two, reaction zone, hydroformylation process for producing normal (N) and iso (I) aldehydes at a N:I ratio, the process comprising contacting an olefinically unsaturated compound with synthesis gas and a catalyst comprising (A) a transition metal, e.g., rhodium, (B) an organobisphosphite ligand, and (C) an organomonophosphite ligand, the contacting conducted in first and subsequent reaction zone(s) and at hydroformylation conditions comprising a transition metal concentration in each zone, the method comprising decreasing the transition metal concentration in the first reaction zone to decrease the N:I ratio or increasing the transition metal concentration in the first reaction zone to increase the N:I ratio.Type: ApplicationFiled: December 15, 2010Publication date: October 11, 2012Inventors: Thomas C. Eisenschmid, Glenn A. Miller, Jeffrey S. Sawrey, Michael A. Brammer
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Publication number: 20120197025Abstract: The invention relates to the synthesis of tetraphenol-substituted structures, in particular meta-substituted xylenes. Said tetraphenol-type structures are reacted to obtain organic phosphorus compounds, in particular organophosphites. The invention further relates to the production of catalytically active compositions which contain transition metals in addition to the aforementioned organic phosphorus compounds. According to another subject matter of the invention, said catalytically active compositions are used in chemical reactions with small molecules, e.g. HCN, CO, hydrogen, and amines.Type: ApplicationFiled: August 26, 2010Publication date: August 2, 2012Applicant: Evonik Oxeno GmbHInventors: Andrea Christiansen, Robert Franke, Dirk Fridag, Dieter Hess, Burkard Kreidler, Dieter Vogt, Laura Bini, Michele Janssen, Bart Hamers
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Publication number: 20120190894Abstract: A gas phase catalytic hydroformylation process for producing at least one aldehyde product in the presence of a transition metal-ligand complex hydroformylation catalyst and water vapor. Surprisingly, catalyst activity can be sustained by having traces of water vapor in the feed stream. Additionally, additional ligand can be added to replace lost ligand to maintain activity. In addition, it has been found that treatment of the catalyst with a buffer can rejuvenate catalyst activity.Type: ApplicationFiled: October 6, 2010Publication date: July 26, 2012Inventor: Richard W. Wegman
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Patent number: 8226829Abstract: Process for separating a dissolved complex catalyst of a metal of group 4, 5, 6, 7, 8, 9 or 10 of the Periodic Table of the Elements and/or any free organophosphorus ligand present from a nonaqueous hydroformylation reaction mixture which contains an aldehyde product and an organic solvent at least one membrane which is more permeable to the hydroformylation product than to the organophosphorus ligand, the separation being carried out under a carbon monoxide partial vapor pressure of more than 200 kPa.Type: GrantFiled: September 8, 2006Date of Patent: July 24, 2012Assignee: Evonik Oxenc GmbHInventors: Klaus-Diether Wiese, Goetz Baumgarten, Franz-Felix Kuppinger, Oliver Moeller, Dagmara Ortmann, Cornelia Borgmann, Wilfried Bueschken
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Patent number: 8178729Abstract: Disclosed is a process for hydroformylation of ?-olefin wherein said ?-olefin is reached with carbon monoxide or carbon monoxide and hydrogen and/or a reducing agent in presence of a catalyst complex based on a rhodium precursor and a ligand mixture comprising at least 1% by weight of trphenylphosphine and at least 5% by weight of diphenylcyclohexylphosphine, tris-(o-tolyl)phosphine, tris-(p-tolyl)phosphine or (2-methyl-phenyl)diphenylphospine.Type: GrantFiled: March 15, 2006Date of Patent: May 15, 2012Assignee: Perstorp Specialty Chemicals ABInventors: Esko Karvinen, Juha Lehtonen, Joni Kunnas, Merja Harteva
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Patent number: 8178730Abstract: Mixed butene streams containing butene-1 and isobutylene and optionally butene-2 are hydroformylated under conditions that hydroformylates all the monomers to yield a mixture of valeraldehydes.Type: GrantFiled: September 21, 2011Date of Patent: May 15, 2012Assignee: ExxonMobil Chemical Patents Inc.Inventors: Raphael F. Caers, Eddy Theophile Van Driessche, Hubertus J. Beckers, Luc Roger Marc Martens, Georges Marie Mathys, John Richard Shutt
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Patent number: 8134031Abstract: An extraction process for a non-aqueous hydroformylation product composition to separate an aldehyde product and to recover a hydroformylation catalyst. The process involves mixing a non-aqueous hydroformylation product composition containing a mixture of formyl-substituted fatty acid triglyceride esters derived from hydroformylating a seed oil, a transition metal-organophosphine ligand wherein the organophosphine is ionically-charged, optionally free ionically-charged organophosphine ligand, and a polar organic solubilizing agent with water and an extraction solvent having low water solubility to recover an organic phase containing the mixture of formyl-substituted fatty acid triglycerides and the low solubility extraction solvent and an aqueous phase containing the transition metal-organophosphine ligand, optional free ligand, the organic solubilizing agent, and water. Optionally, the low solubility extraction solvent can be prepared in situ in the hydroformylation step.Type: GrantFiled: May 30, 2008Date of Patent: March 13, 2012Assignee: Dow Global Technologies LLCInventor: Wei-Jun Peng
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Publication number: 20120059195Abstract: The present invention relates to a catalyst composition for hydroformylation reaction and a hydroformylation process using the same. In the hydroformylation process using the catalyst composition according to the present invention, increased catalytic stability and high catalytic activity can be obtained, and the selectivity of iso-aldehyde produced can be desirably controlled.Type: ApplicationFiled: July 28, 2011Publication date: March 8, 2012Applicant: LG Chem, Ltd.Inventors: Jae-Hui Choi, Dong-Hyun Ko, O-Hak Kwon, Sung-Shik Eom, Moo-Ho Hong, Hye-Won Yang
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Publication number: 20120035377Abstract: Organophosphorus compounds, catalytic systems comprising a metallic element forming a complex with the organophosphorus compounds and methods of hydrocyanation and of hydroformylation employed in the presence of the catalytic systems are described.Type: ApplicationFiled: March 5, 2010Publication date: February 9, 2012Applicant: Rhodia OperationsInventors: Sergio Mastroianni, Igor Mikhel, Paul Pringle
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Patent number: 8110709Abstract: The present invention relates to a process for the hydroformylation of ethylenically unsaturated compounds by reaction with carbon monoxide and hydrogen in the presence of a catalytically active fluid which comprises a dissolved metal complex of a metal of transition group VIII of the Periodic Table of the Elements with at least one phosphoramidite compound as ligand, wherein the fluid is brought into contact with a base.Type: GrantFiled: October 22, 2004Date of Patent: February 7, 2012Assignee: BASF SEInventors: Rainer Papp, Wolfgang Ahlers, Thomas Mackewitz, Rocco Paciello, Martin Volland
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Publication number: 20120029242Abstract: A continuous hydroformylation process for producing at least one aldehyde product by utilizing a transition metal and a ligand mixture comprising an organopolyphosphite and an organomonophosphine, with improved stability of the organopolyphosphite ligand. The process involves reacting one or more olefinically-unsaturated compounds with carbon monoxide and hydrogen in the presence of an organopolyphosphite ligand and an organomonophosphine ligand, at least one of such ligands being bonded to a transition metal to form a transition metal-ligand complex hydroformylation catalyst. Surprisingly the addition of the organomonophosphine to a Rh/organopolyphosphite catalyst system did not result in a significant loss of reaction rate.Type: ApplicationFiled: December 10, 2009Publication date: February 2, 2012Inventor: Michael A. Brammer
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Patent number: 8053605Abstract: The present invention relates to a catalyst composition that includes a triphenylphosphine ligand, a monodentate phosphine ligand, a monodentate phosphine oxide ligand, and a transition metal catalyst, and a hydroformylation process using the same. In the hydroformylation process using the catalyst composition according to the present invention, the high catalytic activity can be obtained, and the selectivity (N/I selectivity) in respects to normal- or iso-aldehyde can be desirably controlled.Type: GrantFiled: June 5, 2008Date of Patent: November 8, 2011Assignee: LG Chem, Ltd.Inventors: Jae-Hui Choi, Dong-Hyun Ko, Sung-Shik Eom, Sang-Gi Lee, Moo-Ho Hong, O-Hark Kwon
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Patent number: 8049043Abstract: Mixed butene streams containing butene-1 and isobutylene and optionally butene-2 are hydroformylated under conditions that hydroformylates all the monomers to yield a mixture of valeraldehydes.Type: GrantFiled: February 17, 2011Date of Patent: November 1, 2011Assignee: ExxonMobil Chemical Patents Inc.Inventors: Raphael F. Caers, Eddy Theophile Van Driessche, Hubertus J. Beckers, Luc Roger Mare Martens, Georges Marie Mathys, John Richard Shutt
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Patent number: 8022256Abstract: Mixed butene streams containing butene-1 and isobutylene and optionally butene-2 are hydroformylated under conditions that hydroformylates all the monomers to yield a mixture of valeraldehydes. Higher temperatures and/or longer residence times and/or higher partial pressure of carbon monoxide than in conventional processes are used to ensure hydroformylation of all the monomers.Type: GrantFiled: September 17, 2004Date of Patent: September 20, 2011Assignee: ExxonMobil Chemical Patents Inc.Inventors: Raphael F. Caers, Eddy Theophile Van Driessche, Hubertus J. Beckers, Luc Roger Marc Martens, Georges Maria Mathys, John Richard Shutt
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Patent number: 8017810Abstract: A hydroformylation process for the production of alcohols comprising reacting, in a reactor system comprising one or more feed streams, a reaction environment and an output stream, a feedstock composition comprising a compound having at least one olefinic carbon-to-carbon bond with hydrogen and carbon monoxide in the presence of an organophosphine modified cobalt hydroformylation catalyst, wherein the hydroformylation process is carried out in the reaction environment which comprises at least two reaction zones, comprising a first reaction zone, a second reaction zone and, optionally, one or more later reaction zones, wherein the molar ratio of hydrogen to carbon monoxide entering the first reaction zone is in the range of from 0.5 to 1.65, and wherein water is added into the reactor system.Type: GrantFiled: May 22, 2008Date of Patent: September 13, 2011Assignee: Shell Oil CompanyInventor: Wilhelmus Peter Mul
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Patent number: 8017811Abstract: A hydroformylation process for the production of alcohols comprising reacting, in a reactor system comprising one or more feed streams, a reaction environment and an output stream, a feedstock composition comprising a compound having at least one olefinic carbon-to-carbon bond with hydrogen and carbon monoxide in the presence of an organophosphine modified cobalt hydroformylation catalyst, wherein the hydroformylation process is carried out in the reaction environment, which comprises at least two reaction zones, wherein the at least two reaction zones comprise an earlier reaction zone and a later reaction zone, wherein the temperature of the later reaction zone is at a temperature which is at least 2° C. greater than the temperature in the earlier reaction zone, and the temperature of the later reaction zone is in the range of from 140° C. to 220° C., and the temperature of the earlier reaction zone is at least 130° C.Type: GrantFiled: May 22, 2008Date of Patent: September 13, 2011Assignee: Shell Oil CompanyInventor: Wilhelmus Peter Mul
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Patent number: 8003816Abstract: The invention relates to a bisphosphite of the formula I where X=a divalent substituted or unsubstituted bisalkylene or bisarylene radical, Y=a divalent substituted or unsubstituted bisarylene or bisalkylene radical, Z=oxygen or NR9, and R1, R2, R3, R4 are identical or different, substituted or unsubstituted, linked, unlinked or fused aryl or heteroaryl radicals and R9 is hydrogen or a substituted or unsubstituted alkyl or aryl radical, a process for preparing it and also the use of this phosphite in catalysis in particular in the catalytic hydroformylation of olefins or organic compounds having C—C double bonds.Type: GrantFiled: November 13, 2007Date of Patent: August 23, 2011Assignee: Evonik Oxeno GmbHInventors: Detlef Selent, Armin Boerner, Burkard Kreidler, Dieter Hess, Klaus-Diether Wiese
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Publication number: 20110201844Abstract: The present invention relates to a catalyst composition for hydroformylation and a method for preparing aldehydes using the same, wherein the catalyst composition for hydroformylation comprises: a triaryl phosphine ligand; a phosphine oxide or phosphine sulfide ligand having a specific chemical formula; and a transition metal catalyst. The catalyst composition provides high catalyst activity and stability and selectivity to normal aldehydes when used in the hydroformylation for preparing aldehydes from olefins.Type: ApplicationFiled: April 22, 2011Publication date: August 18, 2011Inventors: Jae Hui Choi, Dong Hyun Ko, Sung Shik Eom, Moo Ho Hong, O Hark Kwon, Dae Chul Kim
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Publication number: 20110130595Abstract: A process for preparing a C5 aldehyde mixture from a hydrocarbon mixture comprising at least one linear butene by terminal hydroformylation under isomerizing conditions, using a catalyst system comprising rhodium, a bisphosphite ligand, and an amine.Type: ApplicationFiled: April 28, 2009Publication date: June 2, 2011Applicant: Evonik Oxeno GmbHInventors: Hans-Gerd Lueken, Dirk Fridag, Udo Lenz, Hermann-Josef Schulte-Althoff, Klaus-Diether Wiese, Alfred Kaizik, Patrick Muhlack, Wilfried Bueschken, Frank Hoeper
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Patent number: 7943801Abstract: The present invention relates to a catalyst composition that includes a bis-phosphite ligand, a poly-phosphite ligand or a mono-phosphite ligand, and a transition metal catalyst, and a hydroformylation reaction using the same. The catalyst composition has the excellent catalytic activity, and the normal/iso (N/I) selectivity of aldehyde generated by the hydroformylation reaction using the same is increased.Type: GrantFiled: April 8, 2008Date of Patent: May 17, 2011Assignee: LG Chem, Ltd.Inventors: Jae-Hui Choi, Dong-Hyun Ko, Sung-Shik Eom, Ji-Joong Moon, Sang-Gi Lee, O-Hark Kwon
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Patent number: 7935850Abstract: Increasing the propylene content of the propylene feed delivered to a continuous hydroformylation process from the 95 mole % maximum level that is usual in typical chemical grade propylene to at least 97 mole %, for example to the 97.5% level obtainable from the conversion of oxygenates to olefins or the 99.5% level of polymer grade propylene, enables adjustments to be made in the syngas feed to the process. This leads to surprising improvements in hydroformylation product yield, in reactor capacity utilization and in the reduction of amounts of waste gases.Type: GrantFiled: January 28, 2005Date of Patent: May 3, 2011Assignee: ExxonMobil Chemical Patents Inc.Inventors: Raphael Frans Caers, Eddy Theophyle Andrea Van Driessche