Nitrogen Containing Material Utilized Patents (Class 568/455)
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Patent number: 9238607Abstract: The invention concerns a process for the catalytic production of unsaturated aldehydes by reacting an olefin in the presence of carbon monoxide and hydrogen, a rhodium compound and organic phosphorus-containing ligands in an organic solvent as well as a co-catalyst formed from a weak organic acid and an organic amine.Type: GrantFiled: January 20, 2015Date of Patent: January 19, 2016Assignee: EVONIK INDUSTRIES AGInventors: Matthias Beller, Ralf Jackstell, X. Fang
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Patent number: 9018420Abstract: The present invention provides a composition comprising: a) an inert porous support material, b) an ionic liquid, c) a metal selected from group 9 of the Periodic Table of the Elements, d) a phosphorus-containing organic ligand, e) at least one organic amine. The present invention further provides a process for hydroformylating olefin-containing hydrocarbon mixtures to aldehydes with addition of the inventive composition as a catalytically active composition, wherein: a) the water content of the olefin-containing hydrocarbon mixture is adjusted to not more than 20 ppm, b) the content of polyunsaturated compounds in the olefin-containing hydrocarbon mixture is adjusted to not more than 3000 ppm, c) a molar ratio of organic amines according to claims 10-13 to phosphorus-containing organic ligands according to claims 8-9 of at least 4:1 is established, d) a molar ratio of phosphorus-containing organic ligands according to claims 8-9 to rhodium of at least 10:1 is established.Type: GrantFiled: September 27, 2011Date of Patent: April 28, 2015Assignee: Evonik Oxeno GmbHInventors: Robert Franke, Nicole Brausch, Dirk Fridag, Andrea Christiansen, Marc Becker, Peter Wasserscheid, Marco Haumann, Michael Jakuttis, Sebastian Werner, Andreas Schoenweiz
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Patent number: 8969628Abstract: The invention relates to a method for enriching a homogenous catalyst from a process flow comprising said homogenous catalyst as a component, wherein the process flow is conducted over at least one membrane and wherein the membrane wholly or partially comprises a polymer that has planar polymer units connected to one another via a rigid link and wherein the linker is contorted, such that at least one planar polymer unit is connected to at least one second planar polymer unit via the link, in a non-co-planar arrangement. The invention furthermore relates to a method for producing tridecanal.Type: GrantFiled: February 23, 2010Date of Patent: March 3, 2015Assignee: Evonik Degussa GmbHInventors: Markus Priske, Goetz Baumgarten, Hans-Gerd Lueken, Alfred Kaizik, Klaus-Diether Wiese, Uwe Ernst, Patrick Muhlack
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Patent number: 8962893Abstract: Methods of purifying crude cyclopentadienyl magnesium compounds using a scavenging agent are provided. The purified cyclopentadienyl magnesium compounds have very low levels of metallic impurities.Type: GrantFiled: August 28, 2012Date of Patent: February 24, 2015Assignee: Rohm and Haas Electronic Materials LLCInventors: Deodatta Vinayak Shenai-Khatkhate, Stephen J. Manzik
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Patent number: 8921608Abstract: Industrially relevant product selectivities and reaction rates are obtained from rhodium catalyzed hydroformylation of propylene via the use of a novel induction period in which the supramolecular ligand assembly, the rhodium precatalyst and an initial substrate are allowed to form a hydroformylation catalyst that is more selective toward branched aldehydes. Upon heating this incubated mixture and addition of propylene, iso-butyraldehyde is obtained in higher concentrations and rates that are otherwise unattainable.Type: GrantFiled: March 15, 2013Date of Patent: December 30, 2014Assignee: Eastman Chemical CompanyInventors: David William Norman, Elaine Beatrice Mackenzie
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Publication number: 20130324767Abstract: 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: ApplicationFiled: May 31, 2012Publication date: December 5, 2013Applicant: Eastman Chemical CompanyInventors: David William Norman, Joost Nicolaas Hendrik Reek, Tatiana Renee Marie-Louise Besset
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Publication number: 20130324713Abstract: Industrially relevant product selectivities and reaction rates are obtained from rhodium catalyzed hydroformylation of propylene via the use of a novel induction period in which the supramolecular ligand assembly, the rhodium precatalyst and an initial substrate are allowed to form a hydroformylation catalyst that is more selective toward branched aldehydes. Upon heating this incubated mixture and addition of propylene, iso-butyraldehyde is obtained in higher concentrations and rates that are otherwise unattainable.Type: ApplicationFiled: March 15, 2013Publication date: December 5, 2013Applicant: Eastman Chemical CompanyInventors: David William Norman, Elaine Beatrice Mackenzie
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Publication number: 20130324766Abstract: 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: ApplicationFiled: May 31, 2012Publication date: December 5, 2013Applicant: Eastman Chemical CompanyInventors: David William Norman, Joost Nicolaas Hendrik Reek, Tatiana Renee Marie-Louise Besset
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Publication number: 20130289313Abstract: The present invention provides a composition comprising: a) an inert porous support material, b) an ionic liquid, c) a metal selected from group 9 of the Periodic Table of the Elements, d) a phosphorus-containing organic ligand, e) at least one organic amine. The present invention further provides a process for hydroformylating olefin-containing hydrocarbon mixtures to aldehydes with addition of the inventive composition as a catalytically active composition, wherein: a) the water content of the olefin-containing hydrocarbon mixture is adjusted to not more than 20 ppm, b) the content of polyunsaturated compounds in the olefin-containing hydrocarbon mixture is adjusted to not more than 3000 ppm, c) a molar ratio of organic amines according to claims 10-13 to phosphorus-containing organic ligands according to claims 8-9 of at least 4:1 is established, d) a molar ratio of phosphorus-containing organic ligands according to claims 8-9 to rhodium of at least 10:1 is established.Type: ApplicationFiled: September 27, 2011Publication date: October 31, 2013Applicant: EVONIK OXENO GmbHInventors: Robert Franke, Nicole Brausch, Dirk Fridag, Andrea Christiansen, Marc Becker, Peter Wasserscheid, Marco Haumann, Michael Jakuttis, Sebastian Werner, Andreas Schoenweiz
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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: 20120253081Abstract: 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: ApplicationFiled: December 15, 2010Publication date: October 4, 2012Inventors: Thomas C. Eisenschmid, Jeffrey S. Sawrey, Glenn A. Miller, Michael A. Btammer
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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: 20110144392Abstract: 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: ApplicationFiled: August 11, 2009Publication date: June 16, 2011Inventor: Michael A. Brammer
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Publication number: 20110003959Abstract: The invention relates to a coordination complex system comprising a ligand having the formula: R1—SO2—NH—P (XR2)2 (1a); or R1—SO2—N?PH (XR2)2 (1b); or R1—SO(OH)?N—P(XR2)2 (1c); wherein X is independently O, S, NH, or a bond; R1 and R2 are independently selected from hydrogen and substituted or unsubstituted alkyl or aryl; wherein at least one equivalent of the ligand is complexed to an equivalent of a metal selected from a transition metal and lanthanide. The invention also relates to the use of said coordination complexes as catalysts in the hydroformylation, hydrogenation, transfer hydrogenation, hydrocyanation, polymerization, isomerization, carbonylation, cross-coupling, metathesis, CH activation, allylic substitution, aldol condensation, or Michael addition.Type: ApplicationFiled: November 19, 2008Publication date: January 6, 2011Inventors: Joost Nikolaas Hendrik Reek, Frederic William Patureau, Mark Kuil, Albertus Jacobus Sandee, Jurjen Meeuwissen
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Patent number: 7858787Abstract: A process for converting an olefin having x carbon atoms into an olefin having x+1 carbon atoms wherein the process comprises the steps of: (i) reacting an olefin having x carbon atoms with carbon monoxide and hydrogen in the presence of a hydroformylation catalyst to produce an alcohol having x+1 carbon atoms, and (ii) dehydrating the alcohol produced in step (i) in the presence of a dehydration catalyst to produce an olefin having x+1 carbon atoms characterized in that the hydroformylation catalyst used in step (i) is based on: (a) a source of cobalt, and (b) a ligand which contains phosphorus and nitrogen.Type: GrantFiled: September 18, 2007Date of Patent: December 28, 2010Assignee: Shell Oil CompanyInventors: Eit Drent, Roelof Van Ginkel, Willem Wabe Jager
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Patent number: 7781621Abstract: In a method for hydroformylating olefinically unsaturated compounds by means of a cobalt-based catalyst, used in a non-aqueous ionic liquid, liquid at a temperature below 100° C. and comprising at least one cation Q+ and at least one anion A?, said method comprising at least a stage of reaction under pressure and at least a stage of separation of the phases by decantation, recycling of the catalyst is improved: through the use of a ligand selected from among the Lewis bases, more particularly pyridine derivatives, and simultaneously through the addition of this ligand in a post-reaction stage. At the end of this process, the organic phase containing the reaction products can be recovered and the ionic liquid phase containing the catalyst can be recycled to the hydroformylation reactor.Type: GrantFiled: June 22, 2007Date of Patent: August 24, 2010Assignee: Institut Francais du PetroleInventors: Helene Olivier-Bourbigou, Lucien Saussine, Lionel Magna, David Proriol
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Patent number: 7531698Abstract: Tetraphosphorous ligands are combined with transition metal salts to form catalysts for use in hydroformylation, isomerization-hydroformylation, hydrocarboxylation, hydrocyan-ation, isomerization-formylation, hydroaminomethylation and similar related reactions.Type: GrantFiled: December 15, 2006Date of Patent: May 12, 2009Assignee: The Penn State Research FoundationInventors: Xumu Zhang, Yongjun Yan
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Patent number: 7270985Abstract: A process is disclosed to treat the protein hydrolysate, prepared conventionally from a proteinous source, with alkali metal hydride to obtain alcohol which is subsequently oxidized to obtain aldehyde under certain specified conditions, thereby converting large protein molecules into aldehyde based industrial products of much smaller molecular size.Type: GrantFiled: September 14, 2004Date of Patent: September 18, 2007Assignee: Council of Scientific & Industrial ResearchInventors: James Kanagaraj, Gopala Suseela Rajakumar, Sayeed Sadulla
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Patent number: 7217828Abstract: Phosphinines of formula (I) can be combined with metal salts to prepare hydroformylation catalysts. The phosphinine complexes have two phosphorus centers that may be substituted with a variety of hetero atoms or alkyl substituents to modify the ligand characteristics of the phosphinine. Phosphinine metal complexes are employed under normal hydroformylation reaction conditions. The preparatory routes to the phosphinine ligands of formula (I) allow for their convenient synthesis.Type: GrantFiled: August 5, 2004Date of Patent: May 15, 2007Assignee: OXENO Olefinchemie GmbHInventors: Detlef Selent, Armin Boerner, Renat Kadyrov, Cornelia Borgmann, Dieter Hess, Klaus-Diether Wiese, Dirk Roettger
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Patent number: 7115387Abstract: A process is disclosed to treat the protein hydrolysate, prepared conventionally from a proteinous source, with alkyl halide to obtain alcohol which is subsequently oxidized to obtain aldehyde under certain specified conditions, thereby converting large protein molecules into aldehyde based industrial products of much smaller molecular size.Type: GrantFiled: September 15, 2003Date of Patent: October 3, 2006Assignee: Council of Scientific & Industrial ResearchInventors: James Kanagaraj, Gopala Suseela Rajakumar, Sayeed Sadulla
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Patent number: 7060860Abstract: A process for hydroformylating olefinically unsaturated compounds by means of a cobalt-based catalyst is carried out in a non-aqueous ionic liquid which is a liquid at a temperature below 90° C. and comprises at least one ammonium and/or phosphonium and/or sulfonium cation Q+ and at least one anion A?; catalyst recycling is improved by using a ligand selected from the group consisting of Lewis bases and employing a depressurization step between the pressurized reaction step and the step for separating the phases by decanting. At the end of said depressurization step, the organic phase is separated in the decanting step and the non-aqueous ionic liquid containing the catalyst can be re-used.Type: GrantFiled: April 11, 2003Date of Patent: June 13, 2006Assignee: Institut Francais Du PetroleInventors: Lionel Magna, Hélène Olivier-Bourbigou, Lucien Saussine, Virginie Kruger-Tissot
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Patent number: 6982355Abstract: A process is disclosed for making high value olefins and alcohols from synthesis gas as well as a process for an improved yield of alpha-olefins from synthesis gas. The process for hydroformulation of olefins is also provided.Type: GrantFiled: August 23, 2004Date of Patent: January 3, 2006Assignee: Syntroleum CorporationInventor: Armen N. Abazajian
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Patent number: 6852661Abstract: A catalyst comprising at least one complex of a metal of transition group VIII comprising at least one monodentate, bidentate or multidentate phosphinamidite ligand in which the phosphorus atom and the oxygen atom of the phosphinamidite group form part of a 5- to 8-membered heterocycle can be used for the hydroformylation and hydrocyanation of compounds containing at least one ethylenically unsaturated double bond. The phosphinamidite ligand is, for example, represented by the following formulae wherein represents an optionally substituted 5- to 8-membered heterocycle wherein A represents carbon ring members; represents an optionally substituted N-bonded heterocycle wherein (Het) indicates optional ring heteroatoms in addition to the N; and B is a carbon-carbon single bond or a divalent bridging group.Type: GrantFiled: March 23, 2000Date of Patent: February 8, 2005Assignee: BASF AktiengesellschaftInventors: Wolfgang Ahlers, Heiko Maas, Michael Röper
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Patent number: 6677268Abstract: An improved catalyst based on cobalt and/or rhodium dissolved in a non-aqueous ionic solvent which is liquid at a temperature of less than 90° C. More particularly, the catalyst comprises at least one complex of cobalt and/or rhodium co-ordinated with at least one nitrogen-containing ligand and the non-aqueous ionic solvent comprises at least one quaternary ammonium and/or phosphonium cation and at least one inorganic anion.Type: GrantFiled: July 12, 2002Date of Patent: January 13, 2004Assignee: Institut Francais du PetroleInventors: Gerhard Hillebrand, Andre Hirschauer, Dominique Commereuc, Helene Olivier-Bourbigou, Lucien Saussine
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Patent number: 6642420Abstract: A process for the preparation of aldehydes and/or alcohols or amines by reacting olefins in the liquid phase with carbon monoxide and hydrogen, a part of these gases being dispersed in the form of gas bubbles in the reaction liquid and another part being dissolved in the reaction liquid, in the presence or absence of a primary or secondary amine and in the presence of a cobalt carbonyl, rhodium carbonyl, palladium carbonyl or ruthenium carbonyl complex dissolved homogeneously in the reaction liquid and having a phosphorus-, arsenic-, antimony- or nitrogen-containing ligand, at elevated temperatures and at 1 to 100 bar, wherein the reaction is carried out in a vertically arranged, tubular reactor comprising a reactor body and at least one circulation line, a part of the reaction liquid is fed continuously via the circulation line to at least one nozzle which is mounted in the upper part of the reactor body and is coordinated with a guide member, open at the top and bottom and bounded by parallel walls, in theType: GrantFiled: February 7, 2001Date of Patent: November 4, 2003Assignee: BASF AktiengesellschaftInventors: Peter Zehner, Armin Ulonska, Rocco Paciello
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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: 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: 5976408Abstract: An acrylonitrile derivative expressed by the following general formula I, a composition comprising the derivative and having an improved viscosity and optical anisotropy, and a liquid crystal display device: ##STR1## wherein rings A.sup.1 to A.sup.3 represent phenylene, cyclohexylene, dioxane, or pyrimidine, R.sup.Type: GrantFiled: December 19, 1997Date of Patent: November 2, 1999Assignee: Chisso CorporationInventors: Atsuko Fujita, Shuichi Matsui, Koichi Shibata, Kazutoshi Miyazawa, Yasuko Sekiguchi, Etsuo Nakagawa
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Patent number: 5723680Abstract: Aldehydes and/or alcohols are prepared by the hydroformylation of olefins of more than 3 carbon atoms by means of a bare rhodium catalyst dissolved homogeneously in the reaction medium, at superatmospheric pressure and at elevated temperatures, and separation of the rhodium catalyst from the liquid reaction mixture, by a process in which a magnetizable, inorganic pigment coated with a polymeric binder is used for separating the homogeneously dissolved, bare rhodium catalyst from the hydroformylation medium, and this pigment, after it has been laden with the rhodium contained in the hydroformylation medium, is separated from the liquid hydroformylation medium by applying an external magnetic field.Type: GrantFiled: April 18, 1997Date of Patent: March 3, 1998Assignee: BASF AktiengesellschaftInventors: Claudius Kormann, Heinz-Josef Kneuper
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Patent number: 5705521Abstract: A family of compounds has been found to be useful for right-shifting hemoglobin towards a low oxygen affinity state. The effect has particular application in radiation oncology applications. The compounds are capable of acting on hemoglobin in whole blood.Type: GrantFiled: June 7, 1995Date of Patent: January 6, 1998Assignee: The Center for Innovative TechnologyInventor: Donald J. Abraham
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Patent number: 5696297Abstract: Aldehydes or aldehydes and alcohols are prepared by hydroformylation of olefins of more than 3 carbon atoms by a process comprising the stage of hydroformylation by means of a rhodium catalyst homogeneously dissolved in the reaction medium, the separation of the rhodium catalyst from the discharge from the hydroformylation reaction and the recycling of the rhodium separated from the hydroformylation discharge to the hydroformylation stage, wherein the rhodium catalyst is extracted from the hydroformylation discharge into the aqueous phase by means of an aqueous solution of a water-soluble, phosphorus-containing complexing agent selected from the group consisting of the mono- or polysulfonated mono- and oligophosphines and/or from the group consisting of the mono- or polycarboxylated mono- or oligophosphines or the mono- or polysulfonated oligophosphites and the aldehyde or the aldehyde and the alcohol are isolated from the extracted hydroformylation discharge, the aqueous rhodium-containing extract is fed toType: GrantFiled: August 2, 1995Date of Patent: December 9, 1997Assignee: BASF AktiengesellschaftInventors: Heinz-Josef Kneuper, Rocco Paciello, Michael Roper
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Patent number: 5689010Abstract: Aldehydes with a higher number of carbon atoms and high selection are prepared by reacting olefins, in particular from petrochemical refinery products, by a hydroformylation with aldol condensation using a mixed catalyst of rhodium-carbonyl-phosphines and Mannich catalyst.Type: GrantFiled: April 29, 1996Date of Patent: November 18, 1997Assignee: BASF AktiengesellschaftInventors: Rocco Paciello, Franz Merger, Michael Roper, Heinz-Josef Kneuper
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Patent number: 5684167Abstract: 2-Hydroxy-4-methyltetrahydrofuran is prepared by reacting 2-methyl-2-propen-1-ol with hydrogen and carbon monoxide in the presence of:(a) a rhodium compound, and(b) tris(substituted aryl)phosphite having an electronic parameter (.nu.-value) of 2080 to 2090 cm.sup.-1 and a steric parameter (.theta.-value) of 135.degree. to 190.degree. and having formula (1): ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently of each other represent a substituted aryl group having at least 7 carbon atoms, the ratio of said rhodium compound (a) to said tris(substituted aryl) phosphite (b) ranging from 110 to 1000 moles per 1 gram atom of rhodium in said rhodium compound (a).Type: GrantFiled: June 7, 1996Date of Patent: November 4, 1997Assignee: Kuraray Co., Ltd.Inventors: Toshihiro Omatsu, Takashi Onishi, Yasuo Tokitoh
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Patent number: 5672766Abstract: A method for producing aldehydes, which comprises reacting an olefinic unsaturated compound with carbon monoxide and hydrogen for hydroformylation in the presence of a rhodium-phosphite complex catalyst to obtain a reaction product solution containing the rhodium-phosphite complex catalyst and an aldehyde product, and separating from the reaction product solution at least one component selected from the group consisting of carbon monoxide, hydrogen, an unreacted olefinic unsaturated compound, the aldehyde product, a solvent, a medium-boiling by-product and a high-boiling by-product by a separating operation, wherein at least one separating operation is carried out substantially in the absence of water, and the temperature and the residence time in the separating operation are selected to be within such ranges that value P calculated from the following formula (1) would be at most 1:P=5.0.times.10.sup.3 .times.exp?-5000/(T.sub.1 +273)!.times..theta.T.sub.1(1)where T.sub.1 is the maximum temperature (.degree.C.Type: GrantFiled: December 7, 1995Date of Patent: September 30, 1997Assignee: Mitsubishi Chemical CorporationInventors: Tomoyuki Mori, Masaki Takai, Tomohiko Inoue
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Method for lowering oxygen affinity of hemoglobin in redcell suspensions, in whole blood and in vivo
Patent number: 5661182Abstract: Drug compounds are used as allosteric modifiers of hemoglobin present in red blood cells. The compounds bind to only a single pair of symmetry related sites in the central water cavity of hemoglobin at the Lys 99.alpha., Arg 141.alpha., and Asn 108 .beta. residues. When one of the drug compounds is bound to hemoglobin, it will join three separate sub-units of the hemoglobin molecule and stabilize the hemoglobin in a lower oxygen affinity state. Because the compounds used in this method are either not bound by serum albumin or only interact to small degrees with serum albumin, the compounds are active in whole blood and in vivo. The process of allosterically modifying hemoglobin towards a low oxygen affinity state in whole blood and in vivo could be used in a wide variety of applications including in treatments for ischemia, heart disease, wound healing, Alzheimer's, depression, schizophrenia, adult respiratory distress syndrome (ARDS), etc.Type: GrantFiled: June 7, 1995Date of Patent: August 26, 1997Assignee: Virginia Commonwealth UniversityInventors: Donald J. Abraham, Claude Poyart -
Patent number: 5618983Abstract: A hydroformylation process for the production of linear aldehydes from linear olefins, by the reaction of the olefin with hydrogen and carbon monoxide in a solvent containing a catalyst having a platinum component or palladium component, a bidentate diaryl phosphine component where the bridging group is ferrocenyl or 3 to 6 carbon atoms, and a metal promoter component.Type: GrantFiled: August 25, 1995Date of Patent: April 8, 1997Assignees: E. I. Du Pont de Nemours and Company, DSM N. V.Inventor: Patrick M. Burke
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Patent number: 5488174Abstract: Process for the hydroformylation of ethylenically unsaturated compounds, by reaction with carbon monoxide and hydrogen in the presence of a catalyst based on a metal of the platinum group, a source of anions and a bidentate ligand of the formula R.sup.1 R.sup.2 M.sup.1 RM.sup.2 R.sup.3 R.sup.4 wherein M.sup.1 and M.sup.2 are phosphorus, arsenic or antimony, R is a bivalent organic bridging group with 1 to 4 atoms in the bridge, R.sup.1 and R.sup.2 together represent a bivalent cyclic group and R.sup.3 and R.sup.4 independently represent an optionally substituted hydrocarbyl group or together have the same meaning as R.sup.1 and R.sup.2.Type: GrantFiled: August 12, 1994Date of Patent: January 30, 1996Assignee: Shell Oil CompanyInventors: Eit Drent, Dennis H. L. Pello, Jacoba C. L. J. Suykerbuyk
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Patent number: 5471004Abstract: The present invention relates to a process for producing an .alpha.,.beta.-unsaturated aldehyde which comprises subjecting an allyl-hexamethylenetetraammonium derivative to hydrolysis in water and an organic solvent homogeneously immiscible with water. The resulting .alpha.,.beta.-unsaturated aldehyde is useful as medicaments, flavorings, etc., or as raw materials for their production.Type: GrantFiled: June 14, 1994Date of Patent: November 28, 1995Assignee: Takeda Chemical Industries, Ltd.Inventors: Tatsuhiko Kaneko, Noritaka Kuroda, Kenichi Kashiwa
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Patent number: 5434312Abstract: 1,3-Butadiene is hydroformylated at 60.degree. to 150.degree. C. and 1 to 20 MPa in the presence of an aqueous solution which contains, as catalyst, at least one water-soluble rhodium compound and at least one water-soluble organic phosphine. A pH of 8 to 11 is maintained in the aqueous catalyst solution to increase the selectivity of the reaction with respect to the formation of n-five carbon aldehydes and their secondary products. The latter, in particular, can be hydrogenated to 2-propylheptanol, useful as the alcohol component of phthalic ester plasticizers.Type: GrantFiled: September 2, 1994Date of Patent: July 18, 1995Assignee: Hoechst AktiengesellschaftInventors: Bernhard Fell, Peter Hermanns
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Patent number: 5432191Abstract: A family of compounds has been found to be useful for right-shifting hemoglobin towards a low oxygen affinity state. The compounds are capable of acting on hemoglobin in whole blood. In addition, the compounds can maintain the oxygen affinity in blood during storage and can restore the oxygen affinity of outdated blood.Type: GrantFiled: July 30, 1993Date of Patent: July 11, 1995Assignee: The Center for Innovative TechnologyInventors: Donald J. Abraham, Mona Mahran, Ahmed Mehanna, Ramnarayan Randad, Gajanan S. Joshi, Jayashree Panikker
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Patent number: 5387719Abstract: A process for the preparation of aldehydes by hydroformylation of olefins having more than 7 carbon atoms, comprising hydroformylation by means of a rhodium catalyst dissolved homogeneously in the reaction medium, removal of the rhodium catalyst from the hydroformylation reaction product, and recycling of the rhodium separated off from the hydroformylation product into the hydroformylation step, in which the rhodium catalyst is extracted from the hydroformylation product into the aqueous phase by means of an aqueous solution of a nitrogen-containing complexing agent from the group comprising of sulfonated pyridines, sulfonated quinolines, substituted or unsubstituted, sulfonated or sulfonated substituent-carrying 2,2'-bipyridines, 1,10-phenanthrolines, 2,2'-biquinolines, 2,2',6',2"-terpyridines and porphines, and/or from the group comprising of carboxylated pyridines, carboxylated quinolines, substituted or unsubstituted, carboxylated or carboxylated substituent-carrying 2,2'-bipyridines, 1,10-phenanthrolinesType: GrantFiled: September 14, 1993Date of Patent: February 7, 1995Assignee: BASF AktiengesellschaftInventors: Heinz-Josef Kneuper, Michael Roeper, Rocco Paciello
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Patent number: 5290803Abstract: A family of compounds has been found to be useful for right-shifting hemoglobin towards a low oxygen affinity state. The compounds are capable of acting on hemoglobin in whole blood. In addition, the compounds can maintain the oxygen affinity in blood during storage and can restore the oxygen affinity of outdated blood.Type: GrantFiled: January 19, 1993Date of Patent: March 1, 1994Assignee: The Center of Innovative TechnologyInventors: Donald J. Abraham, Mona Mahran, Ahmed Mehanna, Ramnarayan Randad
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Patent number: 5248785Abstract: A family of compounds has been found to be useful for right-shifting hemoglobin towards a low oxygen affinity state. The compounds are capable of acting on hemoglobin in whole blood. In addition, the compounds can maintain the oxygen affinity in blood during storage and can restore the oxygen affinity of outdated blood.Type: GrantFiled: May 18, 1992Date of Patent: September 28, 1993Assignees: Virginia Commonwealth University, Center for Innovative TechnologyInventors: Donald J. Abraham, Ramnarayan Randad
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Patent number: 5183943Abstract: A process for improving the catalytic activity of a partially deactivated solubilized rhodium - tertiary organophosphine complex hydroformylation catalyst.Type: GrantFiled: March 18, 1991Date of Patent: February 2, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: David R. Bryant, James E. Babin, James C. Nicholson, Donald J. Weintritt, Jr.
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Patent number: 5126304Abstract: The invention relates to a method for the preparation of a catalyst for water gas and hydroformylation reactions, which catalyst includes as active components a ruthenic carbonyl and a heterocyclic base on a solid carrier. The catalyst is formed by one or more successive reactions in which the ruthenic carbonyl is fixed from a gas phase onto the carrier and the heterocyclic base is fixed onto the carrier either from a gas phase in the same was as in the case of the ruthenic carbonyl, or from a solution or melt of the heterocyclic base.Type: GrantFiled: December 21, 1990Date of Patent: June 30, 1992Assignee: Neste OyInventors: Pipsa Hirva, Tapani Pakkanen, Tapani Venalainen, Outi Krause, Leila Alvila
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Patent number: 5122539Abstract: Compounds of the general structural formula: ##STR1## wherein X, Y and Z may each be CH.sub.2, NH, or O, R.sub.2-6 are either hydrogen, halogen, or a substituted or unsubstituted C.sub.1, C.sub.2, or C.sub.3 alkyl group and these moieties maybe the same or different, or alkyl moieties of aliphatic or aromatic rings incorporating two of the R.sub.2-6 sites, R.sub.7-8 are hydrogen, methyl, or ethyl groups and these moieties may be the same or different, or alkyl moieties as part of an aliphatic ring connecting R.sub.7 and R.sub.8, and R.sub.9 is a hydrogen, loweralkyl such as methyl, ethyl or propyl, or a salt cation such as sodium, potassium, or ammonium are useful for right-shifting hemoglobin towards a low oxygen affinity state. The compounds are capable of acting on hemoglobin in whole blood. In addition, the compounds can maintain the oxygen affinity in blood during storage and can restore the oxygen affinity of outdated blood.Type: GrantFiled: May 20, 1991Date of Patent: June 16, 1992Assignee: Center for Innovative TechnologyInventors: Donald J. Abraham, Mona Mahran, Ahmed Mehanna, Ramnarayan Randad
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Patent number: 5118867Abstract: The preparation of aldehydes by hydroformylation of olefinically unsaturated compounds. The reaction is carried out in the presence of a catalyst system which contains rhodium and an ammonium salt of a sulfonated phosphorous acid triester which is soluble in organic media.Type: GrantFiled: December 21, 1990Date of Patent: June 2, 1992Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Bernhard Fell, Georgios Papadogianakis
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Patent number: 5049695Abstract: Allosteric hemoglobin modifier compounds having the general formula ##STR1## wherein X and Z may be CH.sub.2, NH or O.Type: GrantFiled: February 12, 1990Date of Patent: September 17, 1991Assignees: Center for Innovative Technology, Virginia Commonwealth UniversityInventors: Donald J. Abraham, Ahmed Mehanna, Ramnarayan Randad, Mona Mahran
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Patent number: 5041685Abstract: The present invention concerns a procedure for preparing alcohols and aldehydes from alkenes and synthesis gas by a heterogeneous reaction in which the catalyst system is composed of Ru.sub.3 (CO).sub.12 and a heterocyclic base in suspension or absorbed in a fixed carrier.Type: GrantFiled: October 25, 1989Date of Patent: August 20, 1991Assignee: Neste OyInventors: Leila Alvila, Outi Krause, Tapani Pakkanen, Tapani Venalainen
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Patent number: 5024983Abstract: The catalyst system is characterized in that it comprises:at least one platinum complex of formula LPtX.sub.2 in which L is an organic compound containing at least two phosphorus atoms capable of coordinating platinum and X is a halogen atom, andat least one combination formed between iron and an alkene carbonate, the alkene group preferably containing from 2 to 6 carbon atoms.The process for its preparation is characterized in that at least one combination formed between iron adn the alkene carbonate is reacted with at least one platinum complex of formula LPtX.sub.2 in at least one solvent for the said complex, at a temperature of between 10.degree. C. and the boiling point of the said solvent. The combination of iron and of an alkene carbonate may be formed by electrochemical reduction.Type: GrantFiled: March 15, 1989Date of Patent: June 18, 1991Assignee: NorsolorInventors: Eric Paumard, Sylvain Mutez, Andre Mortreux, Francis Petit