Nitrogen Containing Material Utilized Patents (Class 568/455)
  • Patent number: 9238607
    Abstract: 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: Grant
    Filed: January 20, 2015
    Date of Patent: January 19, 2016
    Assignee: EVONIK INDUSTRIES AG
    Inventors: Matthias Beller, Ralf Jackstell, X. Fang
  • Patent number: 9018420
    Abstract: 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: Grant
    Filed: September 27, 2011
    Date of Patent: April 28, 2015
    Assignee: Evonik Oxeno GmbH
    Inventors: Robert Franke, Nicole Brausch, Dirk Fridag, Andrea Christiansen, Marc Becker, Peter Wasserscheid, Marco Haumann, Michael Jakuttis, Sebastian Werner, Andreas Schoenweiz
  • Patent number: 8969628
    Abstract: 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: Grant
    Filed: February 23, 2010
    Date of Patent: March 3, 2015
    Assignee: Evonik Degussa GmbH
    Inventors: Markus Priske, Goetz Baumgarten, Hans-Gerd Lueken, Alfred Kaizik, Klaus-Diether Wiese, Uwe Ernst, Patrick Muhlack
  • Patent number: 8962893
    Abstract: 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: Grant
    Filed: August 28, 2012
    Date of Patent: February 24, 2015
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Deodatta Vinayak Shenai-Khatkhate, Stephen J. Manzik
  • Patent number: 8921608
    Abstract: 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: Grant
    Filed: March 15, 2013
    Date of Patent: December 30, 2014
    Assignee: Eastman Chemical Company
    Inventors: David William Norman, Elaine Beatrice Mackenzie
  • Publication number: 20130324767
    Abstract: 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: Application
    Filed: May 31, 2012
    Publication date: December 5, 2013
    Applicant: Eastman Chemical Company
    Inventors: David William Norman, Joost Nicolaas Hendrik Reek, Tatiana Renee Marie-Louise Besset
  • Publication number: 20130324713
    Abstract: 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: Application
    Filed: March 15, 2013
    Publication date: December 5, 2013
    Applicant: Eastman Chemical Company
    Inventors: David William Norman, Elaine Beatrice Mackenzie
  • Publication number: 20130324766
    Abstract: 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: Application
    Filed: May 31, 2012
    Publication date: December 5, 2013
    Applicant: Eastman Chemical Company
    Inventors: David William Norman, Joost Nicolaas Hendrik Reek, Tatiana Renee Marie-Louise Besset
  • Publication number: 20130289313
    Abstract: 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: Application
    Filed: September 27, 2011
    Publication date: October 31, 2013
    Applicant: EVONIK OXENO GmbH
    Inventors: Robert Franke, Nicole Brausch, Dirk Fridag, Andrea Christiansen, Marc Becker, Peter Wasserscheid, Marco Haumann, Michael Jakuttis, Sebastian Werner, Andreas Schoenweiz
  • Publication number: 20120259142
    Abstract: 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: Application
    Filed: December 15, 2010
    Publication date: October 11, 2012
    Inventors: Thomas C. Eisenschmid, Glenn A. Miller, Jeffrey S. Sawrey, Michael A. Brammer
  • Publication number: 20120253081
    Abstract: 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: Application
    Filed: December 15, 2010
    Publication date: October 4, 2012
    Inventors: Thomas C. Eisenschmid, Jeffrey S. Sawrey, Glenn A. Miller, Michael A. Btammer
  • Publication number: 20120197025
    Abstract: 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: Application
    Filed: August 26, 2010
    Publication date: August 2, 2012
    Applicant: Evonik Oxeno GmbH
    Inventors: Andrea Christiansen, Robert Franke, Dirk Fridag, Dieter Hess, Burkard Kreidler, Dieter Vogt, Laura Bini, Michele Janssen, Bart Hamers
  • Publication number: 20110144392
    Abstract: 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: Application
    Filed: August 11, 2009
    Publication date: June 16, 2011
    Inventor: Michael A. Brammer
  • Publication number: 20110003959
    Abstract: 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: Application
    Filed: November 19, 2008
    Publication date: January 6, 2011
    Inventors: Joost Nikolaas Hendrik Reek, Frederic William Patureau, Mark Kuil, Albertus Jacobus Sandee, Jurjen Meeuwissen
  • Patent number: 7858787
    Abstract: 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: Grant
    Filed: September 18, 2007
    Date of Patent: December 28, 2010
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Roelof Van Ginkel, Willem Wabe Jager
  • Patent number: 7781621
    Abstract: 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: Grant
    Filed: June 22, 2007
    Date of Patent: August 24, 2010
    Assignee: Institut Francais du Petrole
    Inventors: Helene Olivier-Bourbigou, Lucien Saussine, Lionel Magna, David Proriol
  • Patent number: 7531698
    Abstract: 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: Grant
    Filed: December 15, 2006
    Date of Patent: May 12, 2009
    Assignee: The Penn State Research Foundation
    Inventors: Xumu Zhang, Yongjun Yan
  • Patent number: 7270985
    Abstract: 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: Grant
    Filed: September 14, 2004
    Date of Patent: September 18, 2007
    Assignee: Council of Scientific & Industrial Research
    Inventors: James Kanagaraj, Gopala Suseela Rajakumar, Sayeed Sadulla
  • Patent number: 7217828
    Abstract: 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: Grant
    Filed: August 5, 2004
    Date of Patent: May 15, 2007
    Assignee: OXENO Olefinchemie GmbH
    Inventors: Detlef Selent, Armin Boerner, Renat Kadyrov, Cornelia Borgmann, Dieter Hess, Klaus-Diether Wiese, Dirk Roettger
  • Patent number: 7115387
    Abstract: 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: Grant
    Filed: September 15, 2003
    Date of Patent: October 3, 2006
    Assignee: Council of Scientific & Industrial Research
    Inventors: James Kanagaraj, Gopala Suseela Rajakumar, Sayeed Sadulla
  • Patent number: 7060860
    Abstract: 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: Grant
    Filed: April 11, 2003
    Date of Patent: June 13, 2006
    Assignee: Institut Francais Du Petrole
    Inventors: Lionel Magna, Hélène Olivier-Bourbigou, Lucien Saussine, Virginie Kruger-Tissot
  • Patent number: 6982355
    Abstract: 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: Grant
    Filed: August 23, 2004
    Date of Patent: January 3, 2006
    Assignee: Syntroleum Corporation
    Inventor: Armen N. Abazajian
  • Patent number: 6852661
    Abstract: 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: Grant
    Filed: March 23, 2000
    Date of Patent: February 8, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Ahlers, Heiko Maas, Michael Röper
  • Patent number: 6677268
    Abstract: 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: Grant
    Filed: July 12, 2002
    Date of Patent: January 13, 2004
    Assignee: Institut Francais du Petrole
    Inventors: Gerhard Hillebrand, Andre Hirschauer, Dominique Commereuc, Helene Olivier-Bourbigou, Lucien Saussine
  • Patent number: 6642420
    Abstract: 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 the
    Type: Grant
    Filed: February 7, 2001
    Date of Patent: November 4, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Zehner, Armin Ulonska, Rocco Paciello
  • Patent number: 6107524
    Abstract: 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: Grant
    Filed: July 15, 1998
    Date of Patent: August 22, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Rocco Paciello, Heinz-Josef Kneuper, Bernhard Geissler, Michael Roper
  • Patent number: 6040483
    Abstract: 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: Grant
    Filed: May 27, 1998
    Date of Patent: March 21, 2000
    Assignee: Institut Francais du Petrole
    Inventors: Helene Olivier, Dominique Commereuc, Sebastien Drochon
  • Patent number: 5976408
    Abstract: 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: Grant
    Filed: December 19, 1997
    Date of Patent: November 2, 1999
    Assignee: Chisso Corporation
    Inventors: Atsuko Fujita, Shuichi Matsui, Koichi Shibata, Kazutoshi Miyazawa, Yasuko Sekiguchi, Etsuo Nakagawa
  • Patent number: 5723680
    Abstract: 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: Grant
    Filed: April 18, 1997
    Date of Patent: March 3, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Claudius Kormann, Heinz-Josef Kneuper
  • Patent number: 5705521
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: January 6, 1998
    Assignee: The Center for Innovative Technology
    Inventor: Donald J. Abraham
  • Patent number: 5696297
    Abstract: 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 to
    Type: Grant
    Filed: August 2, 1995
    Date of Patent: December 9, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz-Josef Kneuper, Rocco Paciello, Michael Roper
  • Patent number: 5689010
    Abstract: 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: Grant
    Filed: April 29, 1996
    Date of Patent: November 18, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Rocco Paciello, Franz Merger, Michael Roper, Heinz-Josef Kneuper
  • Patent number: 5684167
    Abstract: 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: Grant
    Filed: June 7, 1996
    Date of Patent: November 4, 1997
    Assignee: Kuraray Co., Ltd.
    Inventors: Toshihiro Omatsu, Takashi Onishi, Yasuo Tokitoh
  • Patent number: 5672766
    Abstract: 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: Grant
    Filed: December 7, 1995
    Date of Patent: September 30, 1997
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Tomoyuki Mori, Masaki Takai, Tomohiko Inoue
  • Patent number: 5661182
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: August 26, 1997
    Assignee: Virginia Commonwealth University
    Inventors: Donald J. Abraham, Claude Poyart
  • Patent number: 5618983
    Abstract: 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: Grant
    Filed: August 25, 1995
    Date of Patent: April 8, 1997
    Assignees: E. I. Du Pont de Nemours and Company, DSM N. V.
    Inventor: Patrick M. Burke
  • Patent number: 5488174
    Abstract: 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: Grant
    Filed: August 12, 1994
    Date of Patent: January 30, 1996
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Dennis H. L. Pello, Jacoba C. L. J. Suykerbuyk
  • Patent number: 5471004
    Abstract: 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: Grant
    Filed: June 14, 1994
    Date of Patent: November 28, 1995
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Tatsuhiko Kaneko, Noritaka Kuroda, Kenichi Kashiwa
  • Patent number: 5434312
    Abstract: 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: Grant
    Filed: September 2, 1994
    Date of Patent: July 18, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Bernhard Fell, Peter Hermanns
  • Patent number: 5432191
    Abstract: 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: Grant
    Filed: July 30, 1993
    Date of Patent: July 11, 1995
    Assignee: The Center for Innovative Technology
    Inventors: Donald J. Abraham, Mona Mahran, Ahmed Mehanna, Ramnarayan Randad, Gajanan S. Joshi, Jayashree Panikker
  • Patent number: 5387719
    Abstract: 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-phenanthrolines
    Type: Grant
    Filed: September 14, 1993
    Date of Patent: February 7, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz-Josef Kneuper, Michael Roeper, Rocco Paciello
  • Patent number: 5290803
    Abstract: 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: Grant
    Filed: January 19, 1993
    Date of Patent: March 1, 1994
    Assignee: The Center of Innovative Technology
    Inventors: Donald J. Abraham, Mona Mahran, Ahmed Mehanna, Ramnarayan Randad
  • Patent number: 5248785
    Abstract: 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: Grant
    Filed: May 18, 1992
    Date of Patent: September 28, 1993
    Assignees: Virginia Commonwealth University, Center for Innovative Technology
    Inventors: Donald J. Abraham, Ramnarayan Randad
  • Patent number: 5183943
    Abstract: A process for improving the catalytic activity of a partially deactivated solubilized rhodium - tertiary organophosphine complex hydroformylation catalyst.
    Type: Grant
    Filed: March 18, 1991
    Date of Patent: February 2, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David R. Bryant, James E. Babin, James C. Nicholson, Donald J. Weintritt, Jr.
  • Patent number: 5126304
    Abstract: 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: Grant
    Filed: December 21, 1990
    Date of Patent: June 30, 1992
    Assignee: Neste Oy
    Inventors: Pipsa Hirva, Tapani Pakkanen, Tapani Venalainen, Outi Krause, Leila Alvila
  • Patent number: 5122539
    Abstract: 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: Grant
    Filed: May 20, 1991
    Date of Patent: June 16, 1992
    Assignee: Center for Innovative Technology
    Inventors: Donald J. Abraham, Mona Mahran, Ahmed Mehanna, Ramnarayan Randad
  • Patent number: 5118867
    Abstract: 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: Grant
    Filed: December 21, 1990
    Date of Patent: June 2, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Bahrmann, Bernhard Fell, Georgios Papadogianakis
  • Patent number: 5049695
    Abstract: Allosteric hemoglobin modifier compounds having the general formula ##STR1## wherein X and Z may be CH.sub.2, NH or O.
    Type: Grant
    Filed: February 12, 1990
    Date of Patent: September 17, 1991
    Assignees: Center for Innovative Technology, Virginia Commonwealth University
    Inventors: Donald J. Abraham, Ahmed Mehanna, Ramnarayan Randad, Mona Mahran
  • Patent number: 5041685
    Abstract: 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: Grant
    Filed: October 25, 1989
    Date of Patent: August 20, 1991
    Assignee: Neste Oy
    Inventors: Leila Alvila, Outi Krause, Tapani Pakkanen, Tapani Venalainen
  • Patent number: 5024983
    Abstract: 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: Grant
    Filed: March 15, 1989
    Date of Patent: June 18, 1991
    Assignee: Norsolor
    Inventors: Eric Paumard, Sylvain Mutez, Andre Mortreux, Francis Petit