Patents by Inventor David Robert Bryant

David 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: 7196230
    Abstract: A novel organophosphorus composition and synthesis thereof, the composition being characterized by one phosphite moiety, one phosoxophite moiety, and a plurality of sterically bulky substituents. The novel composition finds utility as a ligand in Group VIII transition metal phosoxophite complex catalysts and complex catalyst precursors that are used in carbonylation processes, preferably, hydroformylation processes. Additionally, there is disclosed a novel method of preparing a phosphoromonochloridite composition that finds utility as a precursor to the novel phosoxophite composition.
    Type: Grant
    Filed: March 4, 2003
    Date of Patent: March 27, 2007
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Wei-Jun Peng, David Robert Bryant
  • Patent number: 6362367
    Abstract: This invention relates to a process for producing one or more organic acids in high purity which process comprises (i) oxidizing in a liquid oxidation reactor one or more organic liquids with essentially pure oxygen or oxygen-enriched air containing at least about 50% oxygen, at a temperature sufficiently stable to prevent cycling of reaction rate, to produce a crude reaction product fluid, and (ii) refining said crude reaction product fluid to give said one or more organic acids in high purity. The oxidation temperature is preferably controlled to within about ±3° C. of a target temperature. The organic acids described herein is useful in a variety of applications, such as intermediates in the manufacture of chemical compounds, pharmaceutical manufacture and the like.
    Type: Grant
    Filed: April 21, 1998
    Date of Patent: March 26, 2002
    Assignee: Union Carbide Chemicals & Plastics Technology Corp.
    Inventors: John Braithwaite, David Robert Bryant, David James Miller, John Earl Logsdon
  • Publication number: 20020010364
    Abstract: This invention relates to a process for producing one or more organic acids in high purity which process comprises (i) oxidizing in a liquid oxidation reactor one or more organic liquids with essentially pure oxygen or oxygen-enriched air containing at least about 50% oxygen, at a temperature sufficiently stable to prevent cycling of reaction rate, to produce a crude reaction product fluid, and (ii) refining said crude reaction product fluid to give said one or more organic acids in high purity. The oxidation temperature is preferably controlled to within about ±3° C. of a target temperature. The organic acids described herein is useful in a variety of applications, such as intermediates in the manufacture of chemical compounds, pharmaceutical manufacture and the like.
    Type: Application
    Filed: April 21, 1998
    Publication date: January 24, 2002
    Inventors: JOHN BRAITHWAITE, DAVID ROBERT BRYANT, DAVID JAMES MILLER, JOHN EARL LOGSDON
  • Publication number: 20020007096
    Abstract: This invention relates to processes for producing substituted or unsubstituted alkenols. The process subjects an alkadiene to reductive hydroformylation to selectively produce at least one substituted or unsubstituted alkenols. The process is particularly useful in producing pentenols from butadiene. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted alkenols as principal reaction products.
    Type: Application
    Filed: April 15, 1997
    Publication date: January 17, 2002
    Inventors: DIANE LEE PACKETT, JOHN ROBERT BRIGGS, DAVID ROBERT BRYANT, AILENE GARDNER PHILLIPS, DAVID JAMES SCHRECK, ANIL SAKHARAM GURAM, KURT DAMAR OLSON, THOMAS CARL EISENSCHMID
  • Patent number: 6310260
    Abstract: This invention relates to a process for separating one or more organophosphorus ligand degradation products, one or more reaction byproducts and one or more products from a continuously generated reaction product fluid comprising one or more unreacted reactants, a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more organophosphorus ligand degradation products, said one or more reaction byproducts, said one or more products, one or more polar solvents and one or more nonpolar solvents by phase separation wherein (i) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more products is expressed by a partition coefficient ratio Ef1 which is a value greater than about 2.5, (ii) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more organophosphorus ligand degradation products is expressed by a partition coefficient ratio Ef2 which is a value greater than about 2.
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: October 30, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John Nicholas Argyropoulos, Jeffrey Scott Kanel, Michael Leo Tulchinsky, David James Miller, Donald Lee Morrison, Paul Foley, David Robert Bryant, Ailene Gardner Phillips, Brian Michael Roesch, John Robert Briggs, Max Min Lee, John Michael Maher
  • Patent number: 6307110
    Abstract: This invention relates to a process for separating one or more organophosphorus ligand degradation products, one or more reaction byproducts and one or more products from a continuously generated reaction product fluid comprising one or more unreacted reactants, a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more organophosphorus ligand degradation products, said one or more reaction byproducts, said one or more products, one or more nonpolar solvents and one or more polar solvents by phase separation wherein (i) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more products is expressed by a partition coefficient ratio Ef1which is a value greater than about 2.5, (ii) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more organophosphorus ligand degradation products is expressed by a partition coefficient ratio Ef2 which is a value greater than about 2.
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: October 23, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John Nicholas Argyropoulos, Jeffrey Scott Kanel, Michael Leo Tulchinsky, David James Miller, Donald Lee Morrison, Paul Foley, David Robert Bryant, Ailene Gardner Phillips, Brian Michael Roesch, John Robert Briggs, Max Min Lee, John Michael Maher
  • Patent number: 6307108
    Abstract: This invention relates to a process for separating one or more organophosphorus ligand degradation products, one or more reaction byproducts and one or more formylester products from a reaction product fluid comprising one or more unreacted unsaturated ester reactants, a metal-organophoshorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more organophosphorus ligand degradation products, said one or more reaction byproducts, said one or more products, a nonpolar solvent and a polar solvent by phase separation wherein (i) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more products is expressed by a partition coefficient ratio Ef1 which is a value greater than about 2.5 (ii) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more organophosphorus ligand degradation products is expressed by a partition coefficient ratio Ef2 which is a value greater than about 2.
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: October 23, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John Nicholas Argyropoulos, Jeffrey Scott Kanel, Michael Leo Tulchinsky, David James Miller, Donald Lee Morrison, Paul Foley, David Robert Bryant
  • Patent number: 6307109
    Abstract: This invention relates to a process for separating one or more products from a reaction product fluid comprising a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more products, one or more nonpolar reaction solvents and one or more polar reaction solvents, in which said reaction product fluid exhibits phase behavior depicted by FIG. 1, wherein said process comprises (1) supplying said reaction product fluid from a reaction zone to a separation zone, (2) controlling concentration of said one or more nonpolar reaction solvents and said one or more polar reaction solvents, temperature and pressure in said separation zone sufficient to obtain by phase separation two immiscible liquid phases depicted by regions 2, 4 and 6 of FIG. 1 comprising a polar phase and a nonpolar phase and to prevent or minimize formation of three immiscible liquid phases depicted by region 5 of FIG. 1 and one homogeneous liquid phase depicted by regions 1, 3 and 7 of FIG.
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: October 23, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Jeffrey Scott Kanel, David Robert Bryant, Brian Michael Roesch, Ailene Gardner Phillips
  • Patent number: 6303829
    Abstract: This invention relates to a process for separating one or more products from a reaction product fluid comprising a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more products, one or more nonpolar reaction solvents and one or more polar reaction solvents, wherein said process comprises (1) subjecting said reaction product fluid to fractional countercurrent extraction with at least two immiscible extraction solvents, said at least two immiscible extraction solvents comprising at least one nonpolar extraction solvent and at least one polar extraction solvent, to obtain a nonpolar phase comprising said metal-organophosphorus ligand complex catalyst, said optionally free organophosphorus ligand, said one or more nonpolar reaction solvents and said at least one nonpolar extraction solvent and a polar phase comprising said one or more products, said one or more polar reaction solvents and said at least one polar extraction solvent, and (2) recovering said polar
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: October 16, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Jeffrey Scott Kanel, John Nicholas Argyropoulos, Ailene Gardner Phillips, Brian Michael Roesch, John Robert Briggs, Max Min Lee, John Michael Maher, David Robert Bryant
  • Patent number: 6303830
    Abstract: This invention relates to a process for separating one or more organophosphorus ligand degradation products, one or more reaction byproducts and one or more formylester products from a reaction product fluid comprising one or more unreacted unsaturated ester reactants, a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more organophosphorus ligand degradation products, said one or more reaction byproducts, said one or more products, a polar solvent and a nonpolar solvent by phase separation wherein(i) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more products is expressed by a partition coefficient ratio Ef1 which is a value greater than about 2.5, (ii) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more organophosphorus ligand degradation products is expressed by a partition coefficient ratio Ef2 which is a value greater than about 2.
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: October 16, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John Nicholas Argyropoulos, Jeffrey Scott Kanel, Michael Leo Tulchinsky, David James Miller, Donald Lee Morrison, Paul Foley, David Robert Bryant
  • Patent number: 6300496
    Abstract: This invention relates in part to processes for producing one or more substituted or unsubstituted epsilon caprolactams, e.g., epsilon caprolactam, which comprise (a) converting one or more substituted or unsubstituted hydroxyaldehydes, e.g., 6-hydroxyhexanal, optionally in the presence of a catalyst or a catalyst and promoter, to one or more substituted or unsubstituted hydroxyamides, e.g. 6-hydroxycaproamide, and/or one or more substituted or unsubstituted epsilon caprolactam precursors, e.g.
    Type: Grant
    Filed: October 6, 1999
    Date of Patent: October 9, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Kurt Damar Olson, Thomas Carl Eisenschmid, David Robert Bryant, Arthur Roy Doumaux, Jr.
  • Patent number: 6294700
    Abstract: This invention relates to a process for separating one or more products from a reaction product fluid comprising a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more products, one or more polar reaction solvents and one or more nonpolar reaction solvents, wherein said process comprises (1) subjecting said reaction product fluid to fractional countercurrent extraction with at least two immiscible extraction solvents, said at least two immiscible extraction solvents comprising at least one polar extraction solvent and at least one nonpolar extraction solvent, to obtain a polar phase comprising said metal-organophosphorus ligand complex catalyst, said optionally free organophosphorus ligand, said one or more polar reaction solvents and said at least one polar extraction solvent and a nonpolar phase comprising said one or more products, said one or more nonpolar reaction solvents and said at least one nonpolar extraction solvent, and (2) recovering said nonpo
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: September 25, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Jeffrey Scott Kanel, John Nicholas Argyropoulos, Ailene Gardner Phillips, Brian Michael Roesch, John Robert Briggs, Max Min Lee, John Michael Maher, David Robert Bryant
  • Patent number: 6252121
    Abstract: This invention relates to a process for separating one or more cyclic products from a reaction product fluid comprising one or more cyclic reactants, a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, a non-polar solvent and said one or more cyclic products, wherein said process comprises: (1) reacting said one or more cyclic reactants in the presence of said metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand and non-polar solvent to form a multiphase reaction product fluid; and (2) separating said multiphase reaction product fluid to obtain a non-polar phase comprising said one or more cyclic reactants, metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand and non-polar solvent and a polar phase comprising said one or more cyclic products.
    Type: Grant
    Filed: July 27, 1999
    Date of Patent: June 26, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John Nicholas Argyropoulos, David Robert Bryant, Michael Leo Tulchinsky, Jeffrey Scott Kanel, Paul Foley, Barry Brent Fish
  • Patent number: 6187970
    Abstract: This invention relates in part to processes for producing one or more substituted or unsubstituted 1,6-hexanediols which comprise subjecting one or more substituted or unsubstituted penten-1-ols to reductive hydroformylation in the presence of a reductive hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce said one or more substituted or unsubstituted 1,6-hexanediols. The substituted and unsubstituted 1,6-hexanediols 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 1,6-hexanediols as principal product(s) of reaction.
    Type: Grant
    Filed: April 15, 1997
    Date of Patent: February 13, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John Robert Briggs, Diane Lee Packett, David Robert Bryant, Ailene Gardner Phillips, David James Schreck, Anil Sakharam Guram, Kurt Damar Olson, Thomas Carl Eisenschmid, Eric Bruce Tjaden
  • Patent number: 6090987
    Abstract: This invention relates to a method of stabilizing a metal-organophosphorus ligand complex catalyst against deactivation in a process which comprises reacting one or more reactants in the presence of a metal-organophosphorus ligand complex catalyst and optionally free organophosphorus ligand to produce a reaction product fluid comprising one or more products, and in which at least a portion of said process is conducted under separation conditions sufficient to effect at least some deactivation of the metal-organophosphorus ligand complex catalyst, which method comprises conducting the portion of said process that occurs under separation conditions in the presence of one or more alkadienes sufficient to prevent and/or lessen deactivation of the metal-organophosphorus ligand complex catalyst.
    Type: Grant
    Filed: July 6, 1998
    Date of Patent: July 18, 2000
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Ernst Billig, David Robert Bryant, Craig Alan Beasley, Donald Lee Morrison, Michael David Warholic, Kenneth Elwood Stockman
  • Patent number: 5952530
    Abstract: This invention relates to a process for separating one or more products from a reaction product fluid comprising a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, a nonpolar solvent and said one or more products, wherein said process comprises (1) mixing said reaction product fluid with a polar solvent to obtain by phase separation a non-polar phase comprising said metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand and said nonpolar solvent and a polar phase comprising said one or more products and polar solvent, and (2) recovering said polar phase from said nonpolar phase; wherein said organophosphorus ligand has a partition coefficient between the nonpolar solvent and the polar solvent of greater than about 5, and said one or more products have a partition coefficient between the polar solvent and the nonpolar solvent of greater than about 0.5.
    Type: Grant
    Filed: February 2, 1998
    Date of Patent: September 14, 1999
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John N. Argyropoulos, David Robert Bryant, Donald Lee Morrison, Kenneth Elwood Stockman
  • Patent number: 5932772
    Abstract: This invention relates to a process for separating one or more products from a reaction product fluid comprising a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, a polar solvent and said one or more products, wherein said process comprises (1) mixing said reaction product fluid with a nonpolar solvent to obtain by phase separation a polar phase comprising said metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand and said polar solvent and a nonpolar phase comprising said one or more products and nonpolar solvent, and (2) recovering said nonpolar phase from said polar phase; wherein said organophosphorus ligand has a partition coefficient between the polar solvent and the nonpolar solvent of greater than about 10, and said one or more products have a partition coefficient between the nonpolar solvent and the polar solvent of greater than about 0.5.
    Type: Grant
    Filed: February 2, 1998
    Date of Patent: August 3, 1999
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John N. Argyropoulos, David Robert Bryant, Donald Lee Morrison, Kenneth Elwood Stockman, Anthony George Abatjoglou
  • Patent number: 5929289
    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: March 3, 1998
    Date of Patent: July 27, 1999
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Anthony George Abatjoglou, David Robert Bryant, John Michael Maher
  • Patent number: 5925754
    Abstract: This invention relates to a composition comprising (a) epsilon caprolactam and (b) one or more of 5-?4,5-di(3-carboxypropyl)-2-pyridyl!pentanoic acid or salt or amide, 4-?4,5-di(2-carboxypropyl)-2-pyridyl!-2-methylbutanoic acid or salt or amide, 2-?2-(2-carboxybutyl)-5-(1-carboxypropyl)-4-pyridyl!butanoic acid or salt or amide, 5-?3,5-di(3-carboxypropyl)-2-pyridyl!pentanoic acid or salt or amide, 4-?3,5-di(2-carboxypropyl)-2-pyridyl!-2-methylbutanoic acid or salt or amide, 2-?-2-(2-carboxybutyl)-5-(1-carboxypropyl)-3-pyridyl!butanoic acid or salt or amide, 5-amino-4-methylpentanamide, 4-amino-3-ethylbutanamide, 5-?4,5-di(4-hydroxybutyl)-2-pyridyl!pentanol, 4-?4,5-di(2-methoxypropyl)-2-pyridyl!-2-methylbutanol, 2-?2-(2-methoxybutyl)-5-(1-methoxypropyl)-4-pyridyl!butanol, 5-?3,5-di(4-hydroxybutyl)-2-pyridyl!pentanol, 4-?3,5-di(2-methoxypropyl)-2-pyridyl!-2-methylbutanol, 2-?2-(2-methoxybutyl)-5-(1-methoxypropyl)-3-pyridyl!butanol, 5-amino-4-methyl-1-pentanol, 5-imino-2-methyl-1-pentanamine, 5-amino-2-methyl-1-p
    Type: Grant
    Filed: October 23, 1997
    Date of Patent: July 20, 1999
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John Michael Maher, David Robert Bryant, Johnathan Eugene Holladay, Thomas Carl Eisenschmid, John Robert Briggs, Kurt Damar Olson
  • Patent number: 5917095
    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-organophosphorus ligand complex catalyst and optionally free organophosphorus 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: March 11, 1997
    Date of Patent: June 29, 1999
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, James Clair Nicholson, John Robert Briggs, Diane Lee Packett, John Michael Maher