Patents by Inventor John G. Frye

John G. Frye 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: 6332968
    Abstract: Electrochemical processes using solid gas-impervious membranes are disclosed for gas cleanup by (A) providing an electrochemical cell comprising first and second zones separated by a solid gas-impervious membrane comprising a mixed metal oxide material of a perovskite structure having electron conductivity and oxygen ion conductivity, (B) passing a gas containing N2O, NO, NO2, SO2, SO3, or a mixture thereof, in contact with the membrane in the first zone, and (C) passing a gas capable of reacting with oxygen in contact with the membrane in the second zone. More particularly, the mixed metal oxide material of a perovskite structure comprises a combination of elements selected from the group consisting of lanthanides, alkaline earth metals, Y, Sc, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Zr, and Nb, oxides thereof, and mixtures of these metals and metal oxides. Advantageously a catalyst is present in the first zone.
    Type: Grant
    Filed: January 26, 2000
    Date of Patent: December 25, 2001
    Assignee: The Standard Oil Company
    Inventors: Terry J. Mazanec, Thomas L. Cable, John G. Frye, Jr., Wayne R. Kliewer
  • Patent number: 6291725
    Abstract: The present invention provides a process for preparation of low molecular weight polyols from high molecular weight polyols in a hydrogenolysis reaction under elevated temperature and hydrogen pressure. The process comprises providing in a reaction mixture the polyols, a base, and a metal catalyst prepared by depositing a transition metal salt on an inert support, reducing the metal salt to the metal with hydrogen, and passivating the metal with oxygen, and wherein the catalyst is reduced with hydrogen prior to the reaction. In particular, the process provides for the preparation of glycerol, propylene glycol, and ethylene glycol from sugar alcohols such as sorbitol or xylitol. In a preferred process, the metal catalyst comprises ruthenium which is deposited on an alumina, titania, or carbon support, and the dispersion of the ruthenium on the support increases during the hydrogenolysis reaction.
    Type: Grant
    Filed: March 3, 2000
    Date of Patent: September 18, 2001
    Assignees: Board of Trustees operating Michigan State University, Battelle Memorial Institute, Pacific Northwest Laboratory
    Inventors: Shubham P. Chopade, Dennis J. Miller, James E. Jackson, Todd A. Werpy, John G. Frye, Jr., Alan H. Zacher
  • Patent number: 6287432
    Abstract: Solid membranes comprising an intimate, gas-impervious, multi-phase mixture of an electronically-conductive material and an oxygen ion-conductive material and/or a mixed metal oxide of a perovskite structure are described. Electrochemical reactor components, such as reactor cells, and electrochemical reactors are also described. The reactor cells generally comprise first and second zones separated by an element having a first surface capable of reducing oxygen to oxygen ions, a second surface capable of reacting oxygen ions with an oxygen-consuming gas, an electron-conductive path between the first and second surfaces and an oxygen ion-conductive path between the first and second surfaces.
    Type: Grant
    Filed: June 14, 1999
    Date of Patent: September 11, 2001
    Assignee: The Standard Oil Company
    Inventors: Terry J. Mazanec, Thomas L. Cable, John G. Frye, Jr., Wayne R. Kliewer
  • Patent number: 6235797
    Abstract: An essentially nickel- and rhenium-free catalyst is described comprising ruthenium on a titania support where the titania is greater than 75% rutile. A catalytic system containing a nickel-free catalyst comprising ruthenium on a titania support where the titania is greater than 75% rutile, and a method using this catalyst in the hydrogenation of an organic compound in the aqueous phase is also described.
    Type: Grant
    Filed: September 3, 1999
    Date of Patent: May 22, 2001
    Assignee: Battelle Memorial Institute
    Inventors: Douglas C. Elliot, Todd A. Werpy, Yong Wang, John G. Frye, Jr.
  • Patent number: 6019885
    Abstract: An electrochemical process for extracting oxygen from an oxygen-containing gas which uses an electrochemical cell having two zones separated by a multi-component membrane made from intimate, gas-impervious, multi-phase mixture of an electronically conductive phase and an oxygen ion-conducting phase. In one zone a gas containing oxygen is passed in contact with the membrane. In the other zone a gas capable of reacting with oxygen is passed in contact with the membrane.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: February 1, 2000
    Assignee: The Standard Oil Company
    Inventors: Terry J. Mazanec, Thomas L. Cable, John G. Frye, Jr., Wayne R. Kliewer
  • Patent number: 5883266
    Abstract: The present invention is based upon the surprising discovery that a 5-carbon compound selected from the group of 4-oxopentanoic acid, at least one lactone of 4-oxopentanoic acid, and combinations thereof, may be hydrogenated with a bimetallic catalyst of a noble metal in combination with a second metal and preserve the pendant methyl group. It was further unexpectedly discovered that the same conditions of bimetallic catalyst in the presence of hydrogen are useful for catalyzing the different intermediate reactions for example angelicalactone to gamma-valerolactone and gamma-valerolactone to 1,4-pentanediol. Finally, it was surprising that levulinic acid could be converted to 2-methyltetrahydrofuran with heating in the presence of the bimetallic catalyst and hydrogen in a single process vessel. The method of the present invention unexpectedly produced a fuel or fuel component having 2-methyltetrahydrofuran either in a yield greater than 4.5 mol % or in combination with alcohols.
    Type: Grant
    Filed: January 16, 1998
    Date of Patent: March 16, 1999
    Assignee: Battelle Memorial Institute
    Inventors: Douglas C. Elliott, John G. Frye
  • Patent number: 5744015
    Abstract: An electrochemical process for producing unsaturated hydrocarbon compounds from unsaturated hydrocarbon compounds and for extracting oxygen from a gas containing N.sub.2 O, NO, NO.sub.2, SO.sub.2, or SO.sub.3 is described. The process is characterized by the use of mixed metal oxide materials having a perovskite structure represented by the formula:A.sub.s A'.sub.t B.sub.u B'.sub.v B".sub.w O.sub.xwherein A represents a lanthanide or Y, or a mixture thereof; A' represents an alkaline earth metal or a mixture thereof; B represents Fe; B' represents Cr or Ti, or a mixture thereof; and B" represents Mn, Co, V, Ni, or Cu, or a mixture thereof.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: April 28, 1998
    Inventors: Terry J. Mazanec, Thomas L. Cable, John G. Frye, Jr., Wayne R. Kliewer
  • Patent number: 5698749
    Abstract: Maleic acid, maleic anhydride or other hydrogenatable precursor are catalytically hydrogenated to 1,4-butanediol and tetrahydrofuran. It has been discovered that high yields of 1,4-butanediol are achieved when the hydrogenation catalyst comprises at least one noble metal of Group VIII of the Periodic Table and at least one of rhenium, tungsten or molybdenum on a carbon support wherein the carbon support has been contacted with an oxidizing agent prior to the deposition of the metals. This hydrogenation catalyst is prepared by the steps of(i) oxidizing the carbon support by contacting the carbon support with an oxidizing agent,(ii) impregnating in one or more impregnation steps comprising contacting the carbon support with a source of Group VIII metal and at least one metal selected from the group consisting of rhenium, tungsten and molybdenum being in at least one solution,(iii) after each impregnation step, drying at a temperature under about 150.degree. C.
    Type: Grant
    Filed: September 6, 1995
    Date of Patent: December 16, 1997
    Assignee: The Standard Oil Company
    Inventors: S. Erik Pedersen, John G. Frye, Jr., Thomas G. Attig, John R. Budge
  • Patent number: 5693212
    Abstract: Solid membranes comprising an intimate, gas-impervious, multi-phase mixture of an electronically-conductive material and an oxygen ion-conductive material and/or a mixed metal oxide of a perovskite structure are described. Electrochemical reactor components, such as reactor cells, and electrochemical reactors are also described for transporting oxygen from any oxygen-containing gas to any gas or mixture of gases that consume oxygen. The reactor cells generally comprise first and second zones separated by an element having a first surface capable of reducing oxygen to oxygen ions, a second surface capable of reacting oxygen ions with an oxygen-consuming gas, an electron-conductive path between the first and second surfaces and an oxygen ion-conductive path between the first and second surfaces. The element may further comprise (1) a porous substrate, (2) an electron-conductive metal, metal oxide or mixture thereof and/or (3) a catalyst.
    Type: Grant
    Filed: August 15, 1996
    Date of Patent: December 2, 1997
    Assignee: The Standard Oil Company
    Inventors: Terry J. Mazanec, Thomas L. Cable, John G. Frye, Jr., Wayne R. Kliewer
  • Patent number: 5591315
    Abstract: An electrochemical process for producing unsaturated hydrocarbon compounds from unsaturated hydrocarbon compounds and for extracting oxygen from a gas containing N.sub.2 O, NO, NO.sub.2, SO.sub.2, or SO.sub.3 is described. The process is characterized by the use of mixed metal oxide materials having a perovskite structure represented by the formula:A.sub.s A'.sub.t B.sub.u B'.sub.v B".sub.w O.sub.xwherein A represents a lanthanide or Y, or a mixture thereof; A' represents an alkaline earth metal or a mixture thereof; B represents Fe; B' represents Cr or Ti, or a mixture thereof; and B" represents Mn, Co, Vi, Ni or Cu, or a mixture thereof.
    Type: Grant
    Filed: February 24, 1995
    Date of Patent: January 7, 1997
    Assignee: The Standard Oil Company
    Inventors: Terry J. Mazanec, Thomas L. Cable, John G. Frye, Jr., Wayne R. Kliewer
  • Patent number: 5306411
    Abstract: Solid membranes comprising an intimate, gas-impervious, multi-phase mixture of an electronically-conductive material and an oxygen ion-conductive material and/or a mixed metal oxide of a perovskite structure are described. Electrochemical reactor components, such as reactor cells, and electrochemical reactors are also described for transporting oxygen from any oxygen-containing gas to any gas or mixture of gases that consume oxygen. The reactor cells generally comprise first and second zones separated by an element having a first surface capable of reducing oxygen to oxygen ions, a second surface capable of reacting oxygen ions with an oxygen-consuming gas, an electron-conductive path between the first and second surfaces and an oxygen ion-conductive path between the first and second surfaces. The element may further comprise (1) a porous substrate, (2) an electron-conductive metal, metal oxide or mixture thereof and/or (3) a catalyst.
    Type: Grant
    Filed: November 27, 1990
    Date of Patent: April 26, 1994
    Assignee: The Standard Oil Company
    Inventors: Terry J. Mazanec, Thomas L. Cable, John G. Frye, Jr., Wayne R. Kliewer
  • Patent number: 4793904
    Abstract: An electrocatalytic process is described for producing synthesis gas from light hydrocarbons such as methane or natural gas. The process generally comprises the steps of(A) providing an electrochemical cell comprising a solid electrolyte having a first surface coated with conductive metal, metal oxide or mixtures thereof capable of facilitating the reduction of oxygen to oxygen ions, and a second surface coated with conductive metal, metal oxide or mixtures thereof, provided that both coatings are stable at the operating temperatures,(B) heating the cell to a temperature of at least 1000.degree. C.,(C) passing an oxygen-containing gas in contact with the first conductive coating,(D) passing methane, natural gas or other light hydrocarbons in contact with the second conductive coating, and(E) recovering synthesis gas.
    Type: Grant
    Filed: October 5, 1987
    Date of Patent: December 27, 1988
    Assignee: The Standard Oil Company
    Inventors: Terry J. Mazanec, Thomas L. Cable, John G. Frye, Jr.
  • Patent number: 4705532
    Abstract: An alcohol composition suitable for mixing with gasoline comprises at least 30 percent by weight of methanol, the remainder of said composition comprising higher alcohols the distribution of which on a methanol-free basis isC.sub.2 --about 10 to 90 weight percent,C.sub.3 --about 15 to 60 weight percent,C.sub.4 --about 0.5 to 35 weight percent,C.sub.5 --about 0 to 15 weight percent,C.sub.6 --about 0 to 15 weight percent,and wherein the percent of C.sub.3 is equal to or greater than 1.25 times the percent of C.sub.4.The alcohol composition can be prepared from hydrogen and carbon monoxide under alcohol forming conditions in the presence of a catalyst containing copper and uranium and alkali or alkaline earth metal.
    Type: Grant
    Filed: January 30, 1987
    Date of Patent: November 10, 1987
    Assignee: The Standard Oil Company
    Inventors: Terry J. Mazanec, John G. Frye, Jr., Harley F. Hardman
  • Patent number: 4677091
    Abstract: Mixed metal oxide catalysts suitable for the production of alcohols from carbon monoxide and hydrogen are prepared by:(a) forming a solution of the metals in a polar organic solvent,(b) precipitating the metals from the solution either in the form of their oxides or a form thermally decomposable to the oxides,(c) calcining the precipitate to form the oxides and remove thermally decomposable components therefrom, and(d) where an anion other than oxide remains from step (c) removing same from the precipitate.Suitable polar organic solvents are ketones, esters, ethers and alcohols, particularly C.sub.1 to C.sub.10 alcohols. Preferably, the precipitated metals are washed with water to remove anions other than oxide. The method is particularly suitable for the production of catalysts containing metals such as uranium which are difficult to precipitate from aqueous solution.
    Type: Grant
    Filed: September 5, 1986
    Date of Patent: June 30, 1987
    Assignee: The Standard Oil Company
    Inventors: Terry J. Mazanec, John G. Frye, Jr.
  • Patent number: 4675306
    Abstract: Catalysts useful for the preparation of alcohols from synthesis gas and containing at leat three metal or metal oxide components are prepared by partially oxidizing an intermetallic compound or alloy with a metal oxidizing agent whereby the agent is incorporated into the catalyst.
    Type: Grant
    Filed: April 11, 1983
    Date of Patent: June 23, 1987
    Assignee: The Standard Oil Company
    Inventors: Terry J. Mazanec, John G. Frye, Jr.
  • Patent number: 4666944
    Abstract: A catalylst is disclosed which has the formulaCu.sub.a ZrMn.sub.b Y.sub.c A.sub.d O.sub.xwhereinY is selected from the group consisting of Al, Zn, Ce, Cr, Co, Pd, Pt, Rh, Ag, Ru, Re, Os, Ta, Nb or a mixture of two or more thereof,A is an alkali or alkaline earth metal or a mixture of alkali and/or alkaline earth metals,a is from about 0.1 to about 3,b is from about 0.01 to about 3,c is from 0 to about 3,d is from about 0.02 to about 2.5, andx is the number of oxygens needed to fulfill the valence requirements of the other elements. A process for making alcohol mixtures is also disclosed which comprises contacting a gaseous reactant containing hydrogen and carbon monoxide (e.g., synthesis gas) with the foregoing catalyst.
    Type: Grant
    Filed: September 4, 1985
    Date of Patent: May 19, 1987
    Assignee: The Standard Oil Company
    Inventors: Terry J. Mazanec, John G. Frye, Jr.
  • Patent number: 4657887
    Abstract: A catalyst composition containing alkali metal or alkaline earth metal uranate suitable for the conversion of mixtures of carbon monoxide and hydrogen has the formulaCu.sub.a U M.sub.b A.sub.c O.sub.xwhere M is one or more metals selected from the group consisting of Th, Pd, Mn, Cr, Fe, Co, Zn, Ce, V, Ru, Rh, Al, Re, Os, Pt, Ir, Ag, Ti, La and Zr, A is an alkaline or alkali earth metal anda is from 0.01 to 5.0;b is from 0 to 5.0 with the proviso that when M is Th the value of b is less than 1;c is a number up to 5.0 selected so that the catalyst composition contains more than 2 percent by weight of Metal A;x is a number such that the valence requirements of the other elements for oxygen are satisfied.The catalyst composition can be used to prepare an alcohol composition containing at least 30 percent by weight of methanol, the remainder of said composition comprising higher alcohols, the distribution of which on a methanol-free basis isC.sub.2 -10 to 90 weight percentC.sub.3 -15 to 60 weight percentC.sub.
    Type: Grant
    Filed: July 15, 1985
    Date of Patent: April 14, 1987
    Assignee: The Standard Oil Company
    Inventors: Harley F. Hardman, Terry J. Mazanec, John G. Frye, Jr.
  • Patent number: 4616000
    Abstract: A ruthenium-free catalyst suitable for the conversion of carbon monoxide and hydrogen to alcohols, particularly methanol, comprises a mixture of metal oxides of the metals copper and beryllium where the atomic ratio of copper to beryllium is from about 0.01 to 1 to 20.0 to 1. A further metal M such as Th or Al may also be present, the atomic ratio of the metal M to beryllium being from about 0.1 to 1 to 7.5 to 1.The catalyst can be employed as convert carbon monoxide and hydrogen at elevated temperature and pressure, for example 100.degree. to 500.degree. C. and 150 to 4000 psig, to a product rich in alcohols and low in acids and hydrocarbons.
    Type: Grant
    Filed: August 9, 1985
    Date of Patent: October 7, 1986
    Assignee: The Standard Oil Company
    Inventors: Terry J. Mazanec, John G. Frye, Jr., Harley F. Hardman
  • Patent number: 4608447
    Abstract: Methanol is converted into alcohols containing at least two carbon atoms by reaction with hydrogen and/or carbon monoxide at elevated temperature and superatmospheric pressure in the presence, as catalyst, of (i) an oxide of Th and/or U and (ii) one or more alkali metals the latter being present in an amount of at least 1% by weight. Preferably the catalyst is free of hydrogenating metals. The methanol can be prepared by reaction of hydrogen and carbon monoxide in the presence of a methanol-forming catalyst.
    Type: Grant
    Filed: March 1, 1985
    Date of Patent: August 26, 1986
    Assignee: The Standard Oil Company
    Inventors: Terry J. Mazanec, Gary V. Goeden, John G. Frye, Jr.
  • Patent number: 4559316
    Abstract: A catalyst is disclosed which has the formulaCu.sub.a ZrMn.sub.b Y.sub.c A.sub.d O.sub.xwhereinY is selected from the group consisting of Al, Zn, Ce, Cr, Co, Pd, Pt, Rh, Ag, Ru, Re, Os, Ta, Nb or a mixture of two or more thereof,A is an alkali or alkaline earth metal or a mixture of alkali and/or alkaline earth metals,a is from about 0.1 to about 3,b is from about 0.01 to about 3,c is from 0 to about 3,d is from about 0.02 to about 2.5, andx is the number of oxygens needed to fulfill the valance requirements of the other elements. A process for making alcohol mixtures is also disclosed which comprises contacting a gaseous reactant containing hydrogen and carbon monoxide (e.g., synthesis gas) with the foregoing catalyst.
    Type: Grant
    Filed: September 21, 1984
    Date of Patent: December 17, 1985
    Assignee: The Standard Oil Company
    Inventors: Terry J. Mazanec, John G. Frye, Jr.