Patents by Inventor Robert Bryant

Robert Bryant has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 5821389
    Abstract: This invention relates in part to processes for producing one or more substituted or unsubstituted hydroxyaldehydes, e.g., 6-hydroxyhexanals, which comprise subjecting one or more substituted or unsubstituted alkadienes, e.g., butadiene, to reductive hydroformylation in the presence of a reductive hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and hydroformylation in the presence of a hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce one or more substituted or unsubstituted hydroxyaldehydes. The substituted and unsubstituted hydroxyaldehydes produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof, e.g., epsilon caprolactone. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted hydroxyaldehydes as principal product(s) of reaction.
    Type: Grant
    Filed: April 15, 1997
    Date of Patent: October 13, 1998
    Assignee: Union Carbide Chemicals & Technology Corporation
    Inventors: John Robert Briggs, Diane Lee Packett, David Robert Bryant, Ailene Gardner Phillips, David James Schreck, Kurt Damar Olson, Erik Bruce Tjaden, Anil Sakharam Guram, Thomas Carl Eisenschmid, Elaine Susan Brigham
  • Patent number: 5789625
    Abstract: This invention relates to a process for separating one or more phosphorus acidic compounds from a reaction product fluid containing said one or more phosphorus acidic compounds, a metal-organophosphite ligand complex catalyst and optionally free organophosphite ligand which process comprises (a) treating said reaction product fluid with water sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said reaction product fluid and (b) treating the water which contains phosphorus acidic compounds removed from said reaction product fluid with an acid removal substance sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said water.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: August 4, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, James Clair Nicholson
  • Patent number: 5786517
    Abstract: This invention relates to a process for separating one or more phosphorus acidic compounds from a reaction product fluid containing said one or more phosphorus acidic compounds, a metal-organophosphite ligand complex catalyst and optionally free organophosphite ligand which process comprises treating said reaction product fluid with water sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said reaction product fluid.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: July 28, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, James Clair Nicholson
  • Patent number: 5767321
    Abstract: This invention relates to a process which comprises reacting one or more reactants in the presence of a metal-organopolyphosphite ligand complex catalyst to produce a reaction product fluid comprising one or more products, wherein said process is conducted at a free organopolyphosphite ligand concentration sufficient to prevent and/or lessen hydrolytic degradation of the organopolyphosphite ligand and deactivation of the metal-organopolyphosphite ligand complex catalyst.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: June 16, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Ernst Billig, David Robert Bryant
  • Patent number: 5763671
    Abstract: This invention relates to a process for separating one or more phosphorus acidic compounds from a hydroformylation reaction product fluid containing said one or more phosphorus acidic compounds, a metal-organophosphite ligand complex catalyst and optionally free organophosphite ligand which process comprises (a) treating said hydroformylation reaction product fluid with water sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said hydroformylation reaction product fluid and (b) treating the water which contains phosphorus acidic compounds removed from said hydroformylation reaction product fluid with an acid removal substance sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said water.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: June 9, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, James Clair Nicholson
  • Patent number: 5763677
    Abstract: This invention relates to a process for separating one or more phosphorus acidic compounds from a hydroformylation reaction product fluid containing said one or more phosphorus acidic compounds, a metal-organophosphite ligand complex catalyst and optionally free organophosphite ligand which process comprises (a) treating said hydroformylation reaction product fluid with water sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said hydroformylation reaction product fluid and (b) treating the water which contains phosphorus acidic compounds removed from said hydroformylation reaction product fluid with an ion exchange resin sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said water.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: June 9, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, James Clair Nicholson, Ernst Billig
  • Patent number: 5763679
    Abstract: This invention relates to a process which comprises reacting one or more reactants in the presence of a metal-organopolyphosphite ligand complex catalyst and optionally free organopolyphosphite ligand to produce a reaction product fluid comprising one or more products, wherein said process is conducted at a carbon monoxide partial pressure such that reaction rate increases as carbon monoxide partial pressure decreases and reaction rate decreases as carbon monoxide partial pressure increases and which is sufficient to prevent and/or lessen deactivation of the metal-organopolyphosphite ligand complex catalyst.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: June 9, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: James Clair Nicholson, David Robert Bryant, James Russell Nelson
  • Patent number: 5763680
    Abstract: This invention relates to a process for separating one or more phosphorus acidic compounds from a reaction product fluid containing said one or more phosphorus acidic compounds, a metal-organophosphite ligand complex catalyst and optionally free organophosphite ligand which process comprises (a) treating said reaction product fluid with water sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said reaction product fluid and (b) treating the water which contains phosphorus acidic compounds removed from said reaction product fluid with an ion exchange resin sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said water.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: June 9, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, James Clair Nicholson, Ernst Billig
  • Patent number: 5763670
    Abstract: This invention relates to a hydroformylation process which comprises reacting one or more olefinic unsaturated compounds with carbon monoxide and hydrogen in the presence of a metal-organopolyphosphite ligand complex catalyst to produce a reaction product fluid comprising one or more aldehydes, wherein said hydroformylation process is conducted at a free organopolyphosphite ligand concentration sufficient to prevent and/or lessen hydrolytic degradation of the organopolyphosphite ligand and deactivation of the metal-organopolyphosphite ligand complex catalyst.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: June 9, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Ernst Billig, David Robert Bryant
  • Patent number: 5756855
    Abstract: The present invention provides a hydroformylation process comprising: (1) forming a reaction mixture containing: (a) an olefinic compound, (b) hydrogen, (c) carbon monoxide, (d) a phosphite in which each phosphorus atom is bonded to three oxygen atoms and at least one such oxygen atom is bonded to a carbon atom of an aromatic ring that is adjacent to another carbon atom of said ring having a pendant monovalent group having a steric hindrance at least as great as the steric hindrance of the isopropyl group, (e) a catalytic amount of rhodium, and (f) a Group VIII metal (other than a rhodium) in an amount sufficient to reduce the rhodium-catalyzed decomposition of the phosphite during the hydroformylation process; and (2) maintaining the reaction mixture under conditions at which the olefinic compound reacts with the hydrogen and carbon monoxide to form an aldehyde.
    Type: Grant
    Filed: August 19, 1994
    Date of Patent: May 26, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Anthony George Abatjoglou, David Robert Bryant, John Michael Maher
  • Patent number: 5744649
    Abstract: This invention relates to a process for separating one or more phosphorus acidic compounds from a hydroformylation reaction product fluid containing said one or more phosphorus acidic compounds, a metal-organophosphite ligand complex catalyst and optionally free organophosphite ligand which process comprises treating said hydroformylation reaction product fluid with water sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said hydroformylation reaction product fluid.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: April 28, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, James Clair Nicholson
  • Patent number: 5744650
    Abstract: This invention relates to a process which comprises reacting one or more reactants in the presence of a metal-organopolyphosphite ligand complex catalyst and optionally free organopolyphosphite ligand to produce a reaction product fluid comprising one or more products, wherein said process is conducted at (a) a carbon monoxide partial pressure such that reaction rate increases as carbon monoxide partial pressure decreases and reaction rate decreases as carbon monoxide partial pressure increases and which is sufficient to prevent and/or lessen deactivation of the metal-organopolyphosphite ligand complex catalyst and (b) a temperature such that the temperature difference between reaction product fluid temperature and inlet coolant temperature is sufficient to prevent and/or lessen cycling of carbon monoxide partial pressure, hydrogen partial pressure, total reaction pressure, reaction rate and/or temperature during said process.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: April 28, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: James Clair Nicholson, David Robert Bryant, James Russell Nelson
  • Patent number: 5741945
    Abstract: This invention relates to processes which comprise reacting one or more reactants in the presence of a metal-organopolyphosphite ligand complex catalyst and optionally free organopolyphosphite ligand, and an amount of a sterically hindered organophosphorus ligand different from the organopolyphosphite ligand of said metal-organopolyphosphite ligand complex catalyst, to produce one or more products. The sterically hindered organophosphorus ligands are useful as indicators of organopolyphosphite ligand depletion in said processes.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: April 21, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, Tak Wai Leung
  • Patent number: 5741944
    Abstract: This invention relates to a process for separating one or more phosphorus acidic compounds from a hydroformylation reaction product fluid containing said one or more phosphorus acidic compounds, a metal-organophosphite ligand complex catalyst and optionally free organophosphite ligand which process comprises treating said hydroformylation reaction product fluid with an aqueous buffer solution sufficient to neutralize and remove at least some amount of said one or more phosphorus acidic compounds from said hydroformylation reaction product fluid.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: April 21, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, Tak Wai Leung, Ernst Billig, Thomas Carl Eisenschmid, James Clair Nicholson
  • Patent number: 5741943
    Abstract: This invention relates to a hydroformylation process which comprises reacting one or more olefinic unsaturated compounds with carbon monoxide and hydrogen in the presence of a metal-organopolyphosphite ligand complex catalyst and optionally free organopolyphosphite ligand, and an amount of a sterically hindered organophosphorus ligand different from the organopolyphosphite ligand of said metal-organopolyphosphite ligand complex catalyst, to produce one or more aldehydes. The sterically hindered organophosphorus ligands are useful as indicators of organopolyphosphite ligand depletion in said hydroformylation process.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: April 21, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, Tak Wai Leung
  • Patent number: 5741942
    Abstract: This invention relates to a process for separating one or more phosphorus acidic compounds from a reaction product fluid containing said one or more phosphorus acidic compounds, a metal-organophosphite ligand complex catalyst and optionally free organophosphite ligand which process comprises treating said reaction product fluid with an aqueous buffer solution sufficient to neutralize and remove at least some amount of said one or more phosphorus acidic compounds from said reaction product fluid.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: April 21, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, Tak Wai Leung, Ernst Billig, Thomas Carl Eisenschmid, James Clair Nicholson
  • Patent number: 5731473
    Abstract: This invention relates to a process which comprises reacting one or more reactants in the presence of a metal-organophosphite ligand complex catalyst and dissolved water and optionally free organophosphite ligand to produce a reaction product fluid comprising one or more products, wherein said process is conducted in the presence of carbon dioxide in an amount sufficient not to effect substantial degradation of any said organophosphite ligand and/or substantial deactivation of said metal-organophosphite ligand complex catalyst.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: March 24, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, James Clair Nicholson, Donald Leroy Bunning, Thomas Carl Eisenschmid, Donald Lee Morrison
  • Patent number: 5731472
    Abstract: This invention relates to a method of stabilizing a metal-organopolyphosphite ligand complex catalyst against deactivation in a process which comprises reacting one or more reactants in the presence of a metal-organopolyphosphite ligand complex catalyst and optionally free organopolyphosphite ligand to produce a reaction product fluid comprising one or more products, which method comprises conducting said process in the presence of one or more free heterocyclic nitrogen compounds sufficient to prevent and/or lessen deactivation of the metal-organopolyphosphite ligand complex catalyst.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: March 24, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Tak Wai Leung, David Robert Bryant, Bernard Leslie Shaw
  • Patent number: 5728893
    Abstract: This invention relates to a process for producing one or more products in a staged reactor having more than one reactive stage which process comprises reacting in said staged reactor one or more reactants with carbon monoxide in the presence of a metal-organophosphorus ligand complex catalyst and optionally free organophosphorus ligand to produce said one or more products, wherein said metal-organophosphorus ligand complex catalyst does not undergo substantial deactivation in the presence of solely carbon monoxide and/or effects a change in normal product selectivity of less than 0.2 percent of normal product per 1 pound per square inch of carbon monoxide partial pressure and/or effects a change in reaction rate of less than 2 percent per 1 pound per square inch of carbon monoxide partial pressure.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: March 17, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Michael Carl Becker, David Robert Bryant, Donald LeRoy Bunning, James Clair Nicholson, Ernst Billig
  • Patent number: 5681473
    Abstract: This invention relates to membrane separation of organic solubilized rhodium-organophosphite complex catalyst and free organophosphite ligand from a homogeneous non-aqueous hydroformylation reaction mixture, said mixture also containing, in addition to said catalyst and free ligand, aldehyde product and an organic solvent.
    Type: Grant
    Filed: May 5, 1995
    Date of Patent: October 28, 1997
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Jay Fingeret Miller, David Robert Bryant, Kenneth Look Hoy, Nancy Ellen Kinkade, Rachel Hilda Zanapalidou