Patents by Inventor Michael A. Lilga
Michael A. Lilga 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).
-
Publication number: 20110306780Abstract: A method of reducing hydroxymethylfurfural (HMF) where a starting material containing HMF in a solvent comprising water is provided. H2 is provided into the reactor and the starting material is contacted with a catalyst containing at least one metal selected from Ni, Co, Cu, Pd, Pt, Ru, Ir, Re and Rh, at a temperature of less than or equal to 250° C. A method of hydrogenating HMF includes providing an aqueous solution containing HMF and fructose. H2 and a hydrogenation catalyst are provided. The HMF is selectively hydrogenated relative to the fructose at a temperature at or above 30° C. A method of producing tetrahydrofuran dimethanol (THFDM) includes providing a continuous flow reactor having first and second catalysts and providing a feed comprising HMF into the reactor. The feed is contacted with the first catalyst to produce furan dimethanol (FDM) which is contacted with the second catalyst to produce THFDM.Type: ApplicationFiled: June 30, 2011Publication date: December 15, 2011Inventors: Michael A. Lilga, Richard T. Hallen, Todd A. Werpy, James F. White, Johnathan E. Holladay, John G. Frye, JR., Alan H. Zacher
-
Publication number: 20110257419Abstract: A method of reducing hydroxymethylfurfural (HMF) where a starting material containing HMF in a solvent comprising water is provided. H2 is provided into the reactor and the starting material is contacted with a catalyst containing at least one metal selected from Ni, Co, Cu, Pd, Pt, Ru, Ir, Re and Rh, at a temperature of less than or equal to 250° C. A method of hydrogenating HMF includes providing an aqueous solution containing HMF and fructose. H2 and a hydrogenation catalyst are provided. The HMF is selectively hydrogenated relative to the fructose at a temperature at or above 30° C. A method of producing tetrahydrofuran dimethanol (THFDM) includes providing a continuous flow reactor having first and second catalysts and providing a feed comprising HMF into the reactor. The feed is contacted with the first catalyst to produce furan dimethanol (FDM) which is contacted with the second catalyst to produce THFDM.Type: ApplicationFiled: June 30, 2011Publication date: October 20, 2011Inventors: Michael A. Lilga, Richard T. Hallen, Todd A. Werpy, James F. White, Johnathan E. Holladay, John G. Frye, JR., Alan H. Zacher
-
Patent number: 7994347Abstract: A method of reducing hydroxymethylfurfural (HMF) where a starting material containing HMF in a solvent comprising water is provided. H2 is provided into the reactor and the starting material is contacted with a catalyst containing at least one metal selected from Ni, Co, Cu, Pd, Pt, Ru, Ir, Re and Rh, at a temperature of less than or equal to 250° C. A method of hydrogenating HMF includes providing an aqueous solution containing HMF and fructose. H2 and a hydrogenation catalyst are provided. The HMF is selectively hydrogenated relative to the fructose at a temperature at or above 30° C. A method of producing tetrahydrofuran dimethanol (THFDM) includes providing a continuous flow reactor having first and second catalysts and providing a feed comprising HMF into the reactor. The feed is contacted with the first catalyst to produce furan dimethanol (FDM) which is contacted with the second catalyst to produce THFDM.Type: GrantFiled: June 8, 2007Date of Patent: August 9, 2011Assignee: Battelle Memorial InstituteInventors: Michael A. Lilga, Richard T. Hallen, Todd A. Werpy, James F. White, Johnathan E. Holladay, John G. Frye, Jr., Alan H. Zacher
-
Publication number: 20100152469Abstract: A method of oxidizing hydroxymethylfurfural (HMF) includes providing a starting material which includes HMF in a solvent comprising water into a reactor. At least one of air and O2 is provided into the reactor. The starting material is contacted with the catalyst comprising Pt on a support material where the contacting is conducted at a reactor temperature of from about 50° C. to about 200° C. A method of producing an oxidation catalyst where ZrO2 is provided and is calcined. The ZrO2 is mixed with platinum (II) acetylacetonate to form a mixture. The mixture is subjected to rotary evaporation to form a product. The product is calcined and reduced under hydrogen to form an activated product. The activated product is passivated under a flow of 2% O2.Type: ApplicationFiled: February 24, 2010Publication date: June 17, 2010Applicant: BATTELLE MEMORIAL INSTITUTEInventors: Michael A. Lilga, Richard T. Hallen, Jianli Hu, James F. White, Michel J. Gray
-
Publication number: 20100152470Abstract: A method of oxidizing hydroxymethylfurfural (HMF) includes providing a starting material which includes HMF in a solvent comprising water into a reactor. At least one of air and O2 is provided into the reactor. The starting material is contacted with the catalyst comprising Pt on a support material where the contacting is conducted at a reactor temperature of from about 50° C. to about 200° C. A method of producing an oxidation catalyst where ZrO2 is provided and is calcined. The ZrO2 is mixed with platinum (II) acetylacetonate to form a mixture. The mixture is subjected to rotary evaporation to form a product. The product is calcined and reduced under hydrogen to form an activated product. The activated product is passivated under a flow of 2% O2.Type: ApplicationFiled: February 24, 2010Publication date: June 17, 2010Applicant: BATTELLE MEMORIAL INSTITUTEInventors: Michael A. Lilga, Richard T. Hallen, Jianli Hu, James F. White, Michel J. Gray
-
Patent number: 7700788Abstract: A method of oxidizing hydroxymethylfurfural (HMF) includes providing a starting material which includes HMF in a solvent comprising water into a reactor. At least one of air and O2 is provided into the reactor. The starting material is contacted with the catalyst comprising Pt on a support material where the contacting is conducted at a reactor temperature of from about 50° C. to about 200° C. A method of producing an oxidation catalyst where ZrO2 is provided and is calcined. The ZrO2 is mixed with platinum (II) acetylacetonate to form a mixture. The mixture is subjected to rotary evaporation to form a product. The product is calcined and reduced under hydrogen to form an activated product. The activated product is passivated under a flow of 2% O2.Type: GrantFiled: October 31, 2007Date of Patent: April 20, 2010Assignee: Battelle Memorial InstituteInventors: Michael A. Lilga, Richard T. Hallen, Jianli Hu, James F. White, Michel J. Gray
-
Patent number: 7687661Abstract: A process is disclosed for conversion of salts of ?-hydroxy carbonyl compounds forming useful conversion products including, e.g., ?,?-unsaturated carbonyl compounds and/or salts of ?,?-unsaturated carbonyl compounds. Conversion products find use, e.g., as feedstock and/or end-use chemicals.Type: GrantFiled: March 15, 2006Date of Patent: March 30, 2010Assignee: Battelle Memorial InstituteInventors: Michael A. Lilga, James F. White, Johnathan E. Holladay, Alan H. Zacher, Danielle S. Muzatko, Rick J. Orth
-
Publication number: 20080103318Abstract: A method of oxidizing hydroxymethylfurfural (HMF) includes providing a starting material which includes HMF in a solvent comprising water into a reactor. At least one of air and O2 is provided into the reactor. The starting material is contacted with the catalyst comprising Pt on a support material where the contacting is conducted at a reactor temperature of from about 50° C. to about 200° C. A method of producing an oxidation catalyst where ZrO2 is provided and is calcined. The ZrO2 is mixed with platinum (II) acetylacetonate to form a mixture. The mixture is subjected to rotary evaporation to form a product. The product is calcined and reduced under hydrogen to form an activated product. The activated product is passivated under a flow of 2% O2.Type: ApplicationFiled: October 31, 2007Publication date: May 1, 2008Inventors: Michael Lilga, Richard Hallen, Jianli Hu, James White, Michel Gray
-
Publication number: 20070287845Abstract: A method of reducing hydroxymethylfurfural (HMF) where a starting material containing HMF in a solvent comprising water is provided. H2 is provided into the reactor and the starting material is contacted with a catalyst containing at least one metal selected from Ni, Co, Cu, Pd, Pt, Ru, Ir, Re and Rh, at a temperature of less than or equal to 250° C. A method of hydrogenating HMF includes providing an aqueous solution containing HMF and fructose. H2 and a hydrogenation catalyst are provided. The HMF is selectively hydrogenated relative to the fructose at a temperature at or above 30° C. A method of producing tetrahydrofuran dimethanol (THFDM) includes providing a continuous flow reactor having first and second catalysts and providing a feed comprising HMF into the reactor. The feed is contacted with the first catalyst to produce furan dimethanol (FDM) which is contacted with the second catalyst to produce THFDM.Type: ApplicationFiled: June 8, 2007Publication date: December 13, 2007Applicant: BATTELLE MEMORIAL INSTITUTEInventors: Michael Lilga, Richard Hallen, Todd Werpy, James White, Johnathan Holladay, John Frye, Alan Zacher
-
Publication number: 20070219390Abstract: A process and apparatus are disclosed for conversion of ?-hydroxy carbonyl compounds forming useful conversion products including, e.g., acrylic acid [CAS No. 79-10-7], acrylates, and acrylamide [CAS No. 79-06-01]. Conversion products find use, e.g., as feedstock and/or end-use chemicals.Type: ApplicationFiled: March 15, 2006Publication date: September 20, 2007Applicants: Battelle Memorial Institute, Cargill, IncorporatedInventors: Alan Zacher, Johnathan Holladay, Michael Lilga, James White, Danielle Muzatko, Rick Orth, Paraskevas Tsobanakis, Xiangsheng Meng, Timothy Abraham
-
Publication number: 20070219391Abstract: A process is disclosed for conversion of salts of ?-hydroxy carbonyl compounds forming useful conversion products including, e.g., ?,?-unsaturated carbonyl compounds and/or salts of ?,?-unsaturated carbonyl compounds. Conversion products find use, e.g., as feedstock and/or end-use chemicals.Type: ApplicationFiled: March 15, 2006Publication date: September 20, 2007Applicant: Battelle Memorial InstituteInventors: Michael Lilga, James White, Johnathan Holladay, Alan Zacher, Danielle Muzatko, Rick Orth
-
Publication number: 20070219397Abstract: A process is disclosed for conversion of ammonium salts of ?-hydroxy carbonyl compounds forming useful conversion products including, e.g., ?, ?-unsaturated carbonyl compounds and/or ammonium salts of ?, ?-unsaturated carbonyl compounds recovered at a high molar yield. Conversion products find use, e.g., as feedstock and/or end-use chemicals.Type: ApplicationFiled: March 15, 2006Publication date: September 20, 2007Applicants: Battelle Memorial Institute, Cargill, IncorporatedInventors: Johnathan Holladay, Alan Zacher, Michael Lilga, James White, Danielle Muzatko, Rick Orth, Paraskevas Tsobanakis, Xiangsheng Meng, Timothy Abraham
-
Patent number: 6992209Abstract: The invention includes a method of forming an alpha, beta-unsaturated compound. A carboxylic acid is mixed with an alpha-hydroxy acid or an alpha-hydroxy ester and is esterified to form an alpha-acyloxy derivative. The alpha-acyloxy derivative is transformed into an alpha, beta-unsaturated derivative. The invention additionally includes a process of forming an acrylate. Lactic acid or a lactic acid ester is reacted with a first portion of acetic acid in the presence of a first catalyst to produce the corresponding 2-acetoxy propionic acid or ester. A non-reacted portion of the acetic acid is recycled. The 2-acetoxy propionic acid or ester is transferred to a second vessel containing a second catalyst, and acetic acid is liberated from the 2-acetoxy propionic acid or ester to produce a corresponding acrylic acid or acrylate ester. The acid or ester is subsequently esterified by reaction with an alcohol to form a desired acrylate ester.Type: GrantFiled: December 9, 2002Date of Patent: January 31, 2006Assignee: Battelle Memorial InstituteInventors: Michael A. Lilga, Todd A. Werpy, Johnathan E. Holladay
-
Publication number: 20040110974Abstract: The invention includes a method of forming an alpha, beta-unsaturated compound. A carboxylic acid is mixed with an alpha-hydroxy acid or an alpha-hydroxy ester and is esterified to form an alpha-acyloxy derivative. The alpha-acyloxy derivative is transformed into an alpha, beta-unsaturated derivative. The invention additionally includes a process of forming an acrylate. Lactic acid or a lactic acid ester is reacted with a first portion of acetic acid in the presence of a first catalyst to produce the corresponding 2-acetoxy propionic acid or ester. A non-reacted portion of the acetic acid is recycled. The 2-acetoxy propionic acid or ester is transferred to a second vessel containing a second catalyst, and acetic acid is liberated from the 2-acetoxy propionic acid or ester to produce a corresponding acrylic acid or acrylate ester. The acid or ester is subsequently esterified by reaction with an alcohol to form a desired acrylate ester.Type: ApplicationFiled: December 9, 2002Publication date: June 10, 2004Inventors: Michael A. Lilga, Todd A. Werpy, Johnathan E. Holladay
-
Patent number: 6545175Abstract: The present invention provides compounds having the formula: wherein: n is 0 or 1; R4 through R12 are independently selected from hydrogen, C1 to C10 alkyl, C6 to C10 aryl, C1 to C10 alkoxy, C1 to C10 aryloxy, C1 to C10 aralkyl; and R1 through R3 are hydrogen, C1 to C10 alkyl, C6 to C10 aryl, or C1 to C10 aralkyl. Methods of making and using these compounds are also described. Methods of converting &agr;-hydroxy carboxylic esters and acids to acrylates are also described.Type: GrantFiled: October 19, 2000Date of Patent: April 8, 2003Assignee: Battelle Memorial InstituteInventors: Todd A. Werpy, Michael A. Lilga
-
Publication number: 20020025449Abstract: The electroactive product of the present invention is a metal cyanide film on a substrate, wherein the improvement is the metal cyanide film having a flux throughput capacity greater than 0.54 millicoulombs/second-cm2 as measured by the specific cyclic voltammetry procedure. The improved metal cyanide film generally has a flux throughput capacity greater than that of unimproved metal cyanide film wherein the improved metal cyanide film was deposited at a slow rate. The present invention enjoys the advantages of greater cation equivalent loading capacity, and achieving ion separations using half the amount of electricity as other electrochemical ion separations.Type: ApplicationFiled: August 17, 1999Publication date: February 28, 2002Inventors: JOHANES H. SUKAMTO, MARK F. BUEHLER, SCOT D. RASSAT, RICK J. ORTH, MICHAEL A. LILGA, RICHARD T. HALLEN
-
Patent number: 5786505Abstract: A method of selectively oxidizing an organic compound in a single vessel comprises: a) combining an organic compound, an acid solution in which the organic compound is soluble, a compound containing two oxygen atoms bonded to one another, and a metal ion reducing agent capable of reducing one of such oxygen atoms, and thereby forming a mixture; b) reducing the compound containing the two oxygen atoms by reducing one of such oxygen atoms with the metal ion reducing agent to, 1) oxidize the metal ion reducing agent to a higher valence state, and 2) produce an oxygen containing intermediate capable of oxidizing the organic compound; c) reacting the oxygen containing intermediate with the organic compound to oxidize the organic compound into an oxidized organic intermediate, the oxidized organic intermediate having an oxidized carbon atom; d) reacting the oxidized organic intermediate with the acid counter ion and higher valence state metal ion to bond the acid counter ion to the oxidized carbon atom and therebyType: GrantFiled: July 3, 1996Date of Patent: July 28, 1998Assignee: Battelle Memorial InstituteInventors: Donald M. Camaioni, Michael A. Lilga
-
Patent number: 5708246Abstract: The present invention is the addition of a semiconductor material and energy to the reaction mixture of organic, acid (for example, trifluoroacetate), and oxygen. A transition metal ion may be added to the reaction mixture. The semiconductor material converts energy to oxidants thereby promoting oxidation of the organic. Alternatively, using metal in combination with exposure to light may be used.Type: GrantFiled: August 28, 1996Date of Patent: January 13, 1998Assignee: Battelle Memorial InstituteInventors: Donald M. Camaioni, Michael A. Lilga
-
Patent number: 5585515Abstract: A method of selectively oxidizing an organic compound in a single vessel comprises: a) combining an organic compound, an acid solution in which the organic compound is soluble, a compound containing two oxygen atoms bonded to one another, and a metal ion reducing agent capable of reducing one of such oxygen atoms, and thereby forming a mixture; b) reducing the compound containing the two oxygen atoms by reducing one of such oxygen atoms with the metal ion reducing agent to, 1) oxidize the metal ion reducing agent to a higher valence state, and 2) produce an oxygen containing intermediate capable of oxidizing the organic compound; c) reacting the oxygen containing intermediate with the organic compound to oxidize the organic compound into an oxidized organic intermediate, the oxidized organic intermediate having an oxidized carbon atom; d) reacting the oxidized organic intermediate with the acid counter ion and higher valence state metal ion to bond the acid counter ion to the oxidized carbon atom and therebyType: GrantFiled: April 30, 1993Date of Patent: December 17, 1996Assignee: Battelle Memorial InstituteInventors: Donald M. Camaioni, Michael A. Lilga
-
Patent number: 5118447Abstract: A method is disclosed for denitrification of nitrates and nitrates present in aqueous waste streams. The method comprises the steps of (1) identifying the concentration nitrates and nitrites present in a waste stream, (2) causing formate to be present in the waste stream, (3) heating the mixture to a predetermined reaction temperature from about 200.degree. C. to about 600.degree. C., and (4) holding the mixture and accumulating products at heated and pressurized conditions for a residence time, thereby resulting in nitrogen and carbon dioxide gas, and hydroxides, and reducing the level of nitrates and nitrites to below drinking water standards.Type: GrantFiled: April 12, 1991Date of Patent: June 2, 1992Assignee: Battelle Memorial InstituteInventors: John L. Cox, Richard T. Hallen, Michael A. Lilga