Patents by Inventor John G. Frye, Jr.

John G. Frye, Jr. 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: 6982328
    Abstract: The invention includes methods of processing plant material by adding water to form a mixture, heating the mixture, and separating a liquid component from a solid-comprising component. At least one of the liquid component and the solid-comprising component undergoes additional processing. Processing of the solid-comprising component produces oils, and processing of the liquid component produces one or more of glycerol, ethylene glycol, lactic acid and propylene glycol. The invention includes a process of forming glycerol, ethylene glycol, lactic acid and propylene glycol from plant matter by adding water, heating and filtering the plant matter. The filtrate containing starch, starch fragments, hemicellulose and fragments of hemicellulose is treated to form linear poly-alcohols which are then cleaved to produce one or more of glycerol, ethylene glycol, lactic acid and propylene glycol. The invention also includes a method of producing free and/or complexed sterols and stanols from plant material.
    Type: Grant
    Filed: March 3, 2003
    Date of Patent: January 3, 2006
    Assignees: Archer Daniels Midland Company, Battelle Memorial Institute
    Inventors: Todd A. Werpy, Andrew J. Schmidt, John G. Frye, Jr., Alan H. Zacher, James A. Franz, Mikhail S. Alnajjar, Gary G. Neuenschwander, Eric V. Alderson, Rick J. Orth, Charles A. Abbas, Kyle E. Beery, Anne M. Rammelsberg, Catherine J. Kim
  • Patent number: 6841085
    Abstract: Methods for hydrogenolysis are described which use a Re-containing multimetallic catalyst for hydrogenolysis of both C—O and C—C bonds. Methods and compositions for reactions of hydrogen over a Re-containing catalyst with compositions containing a 6-carbon sugar, sugar alcohol, or glycerol are described. It has been surprisingly discovered that reaction with hydrogen over a Re-containing multimetallic catalyst resulted in superior conversion and selectivity to desired products such as propylene glycol.
    Type: Grant
    Filed: October 23, 2001
    Date of Patent: January 11, 2005
    Assignee: Battelle Memorial Institute
    Inventors: Todd A. Werpy, John G. Frye, Jr., Alan H. Zacher, Dennis J. Miller
  • Patent number: 6706893
    Abstract: The present invention provides methods for making N-methylpyrrolidine and analogous compounds via hydrogenation. Novel catalysts for this process, and novel conditions/yields are also described. Other process improvements may include extraction and hydrolysis steps. Some preferred reactions take place in the aqueous phase. Starting materials for making N-methylpyrrolidine may include succinic acid, N-methylsuccinimide, and their analogs.
    Type: Grant
    Filed: October 25, 2002
    Date of Patent: March 16, 2004
    Assignee: Battelle Memorial Institute
    Inventors: Todd Werpy, John G. Frye, Jr., Yong Wang, Alan H. Zacher
  • Patent number: 6677385
    Abstract: Methods and compositions for reactions of hydrogen over a Re-containing catalyst with compositions containing a 5-carbon sugar, sugar alcohol, or lactic acid are described. It has been surprisingly discovered that reaction with hydrogen over a Re-containing multimetallic catalyst resulted in superior conversion and selectivity to desired products such as propylene glycol. A process for the synthesis of PG from lactate or lactic acid is also described.
    Type: Grant
    Filed: August 6, 2002
    Date of Patent: January 13, 2004
    Assignee: Battelle Memorial Institute
    Inventors: Todd A. Werpy, John G. Frye, Jr., Alan H. Zacher, Dennis J. Miller
  • Patent number: 6670300
    Abstract: A textured catalyst having a hydrothermally-stable support, a metal oxide and a catalyst component is described. Methods of conducting aqueous phase reactions that are catalyzed by a textured catalyst are also described. The invention also provides methods of making textured catalysts and methods of making chemical products using a textured catalyst.
    Type: Grant
    Filed: June 18, 2001
    Date of Patent: December 30, 2003
    Assignee: Battelle Memorial Institute
    Inventors: Todd Werpy, John G. Frye, Jr., Yong Wang, Alan H. Zacher
  • Patent number: 6670483
    Abstract: The present invention provides methods for making N-methylpyrrolidine and analogous compounds via hydrogenation. Novel catalysts for this process, and novel conditions/yields are also described. Other process improvements may include extraction and hydrolysis steps. Some preferred reactions take place in the aqueous phase. Starting materials for making N-methylpyrrolidine may include succinic acid, N-methylsuccinimide, and their analogs.
    Type: Grant
    Filed: October 25, 2002
    Date of Patent: December 30, 2003
    Assignee: Battelle Memorial Institute
    Inventors: Todd Werpy, John G. Frye, Jr., Yong Wang, Alan H. Zacher
  • Patent number: 6632951
    Abstract: The present invention provides methods for making N-methylpyrrolidine and analogous compounds via hydrogenation. Novel catalysts for this process, and novel conditions/yields are also described. Other process improvements may include extraction and hydrolysis steps. Some preferred reactions take place in the aqueous phase. Starting materials for making N-methylpyrrolidine may include succinic acid, N-methylsuccinimide, and their analogs.
    Type: Grant
    Filed: October 25, 2002
    Date of Patent: October 14, 2003
    Assignee: Battelle Memorial Institute
    Inventors: Todd Werpy, John G. Frye, Jr., Yong Wang, Alan H. Zacher
  • Patent number: 6603021
    Abstract: The present invention provides methods for making N-methylpyrrolidine and analogous compounds via hydrogenation. Novel catalysts for this process, and novel conditions/yields are also described. Other process improvements may include extraction and hydrolysis steps. Some preferred reactions take place in the aqueous phase. Starting materials for making N-methylpyrrolidine may include succinic acid, N-methylsuccinimide, and their analogs.
    Type: Grant
    Filed: June 18, 2001
    Date of Patent: August 5, 2003
    Assignee: Battelle Memorial Institute
    Inventors: Todd Werpy, John G. Frye, Jr., Yong Wang, Alan H. Zacher
  • Patent number: 6570043
    Abstract: The present invention provides a method of converting sugars to their corresponding sugar alcohols by catalytic hydrogenation in the aqueous phase. It has been found that surprisingly superior results can be obtained by utilizing a relatively low temperature (less than 120° C.), selected hydrogenation conditions, and a hydrothermally stable catalyst. These results include excellent sugar conversion to the desired sugar alcohol, in combination with long life under hydrothermal conditions.
    Type: Grant
    Filed: April 27, 2001
    Date of Patent: May 27, 2003
    Assignee: Battelle Memorial Institute
    Inventors: Douglas C. Elliott, Todd A. Werpy, Yong Wang, John G. Frye, Jr.
  • Patent number: 6479713
    Abstract: Methods and compositions for reactions of hydrogen over a Re-containing catalyst with compositions containing a 5-carbon sugar, sugar alcohol, or lactic acid are described. It has been surprisingly discovered that reaction with hydrogen over a Re-containing multimetallic catalyst resulted in superior conversion and selectivity to desired products such as propylene glycol. A process for the synthesis of PG from lactate or lactic acid is also described.
    Type: Grant
    Filed: October 23, 2001
    Date of Patent: November 12, 2002
    Assignee: Battelle Memorial Institute
    Inventors: Todd A. Werpy, John G. Frye, Jr., Alan H. Zacher, Dennis J. Miller
  • 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: 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