Patents by Inventor Johnathan E. Holladay

Johnathan E. Holladay 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: 9012699
    Abstract: Hydrogenolysis systems are provided that can include a reactor housing an Ru-comprising hydrogenolysis catalyst and wherein the contents of the reactor is maintained at a neutral or acidic pH. Reactant reservoirs within the system can include a polyhydric alcohol compound and a base, wherein a weight ratio of the base to the compound is less than 0.05. Systems also include the product reservoir comprising a hydrogenolyzed polyhydric alcohol compound and salts of organic acids, and wherein the moles of base are substantially equivalent to the moles of salts or organic acids. Processes are provided that can include an Ru-comprising catalyst within a mixture having a neutral or acidic pH. A weight ratio of the base to the compound can be between 0.01 and 0.05 during exposing.
    Type: Grant
    Filed: May 9, 2014
    Date of Patent: April 21, 2015
    Assignee: Battelle Memorial Institute
    Inventors: Johnathan E. Holladay, Danielle S. Muzatko, James F. White, Alan H. Zacher
  • Publication number: 20140249335
    Abstract: Hydrogenolysis systems are provided that can include a reactor housing an Ru-comprising hydrogenolysis catalyst and wherein the contents of the reactor is maintained at a neutral or acidic pH. Reactant reservoirs within the system can include a polyhydric alcohol compound and a base, wherein a weight ratio of the base to the compound is less than 0.05. Systems also include the product reservoir comprising a hydrogenolyzed polyhydric alcohol compound and salts of organic acids, and wherein the moles of base are substantially equivalent to the moles of salts or organic acids. Processes are provided that can include an Ru-comprising catalyst within a mixture having a neutral or acidic pH. A weight ratio of the base to the compound can be between 0.01 and 0.05 during exposing.
    Type: Application
    Filed: May 9, 2014
    Publication date: September 4, 2014
    Applicant: Battelle Memorial Institute
    Inventors: Johnathan E. Holladay, Danielle S. Muzatko, James F. White, Alan H. Zacher
  • Patent number: 8754266
    Abstract: Hydrogenolysis systems are provided that can include a reactor housing an Ru-comprising hydrogenolysis catalyst and wherein the contents of the reactor is maintained at a neutral or acidic pH. Reactant reservoirs within the system can include a polyhydric alcohol compound and a base, wherein a weight ratio of the base to the compound is less than 0.05. Systems also include the product reservoir comprising a hydrogenolyzed polyhydric alcohol compound and salts of organic acids, and wherein the moles of base are substantially equivalent to the moles of salts or organic acids. Processes are provided that can include an Ru-comprising catalyst within a mixture having a neutral or acidic pH. A weight ratio of the base to the compound can be between 0.01 and 0.05 during exposing.
    Type: Grant
    Filed: May 10, 2013
    Date of Patent: June 17, 2014
    Assignee: Battelle Memorial Institute
    Inventors: Johnathan E. Holladay, Danielle S. Muzatko, James F. White, Alan H. Zacher
  • Publication number: 20130253231
    Abstract: Hydrogenolysis systems are provided that can include a reactor housing an Ru-comprising hydrogenolysis catalyst and wherein the contents of the reactor is maintained at a neutral or acidic pH. Reactant reservoirs within the system can include a polyhydric alcohol compound and a base, wherein a weight ratio of the base to the compound is less than 0.05. Systems also include the product reservoir comprising a hydrogenolyzed polyhydric alcohol compound and salts of organic acids, and wherein the moles of base are substantially equivalent to the moles of salts or organic acids. Processes are provided that can include an Ru-comprising catalyst within a mixture having a neutral or acidic pH. A weight ratio of the base to the compound can be between 0.01 and 0.05 during exposing.
    Type: Application
    Filed: May 10, 2013
    Publication date: September 26, 2013
    Applicant: Battelle Memorial Institute
    Inventors: Johnathan E. Holladay, Danielle S. Muzatko, James F. White, Alan H. Zacher
  • Patent number: 8501963
    Abstract: The invention includes methods of processing an initial di-carbonyl compound by conversion to a cyclic compound. The cyclic compound is reacted with an alkylating agent to form a derivative having an alkylated ring nitrogen. The invention encompasses a method of producing an N-alkyl product. Ammonia content of a solution is adjusted to produce a ratio of ammonia to di-carboxylate compound of from about 1:1 to about 1.5:1. An alkylating agent is added and the initial compound is alkylated and cyclized. The invention includes methods of making N-methyl pyrrolidinone (NMP). Aqueous ammonia and succinate is introduced into a vessel and ammonia is adjusted to provide a ratio of ammonia to succinate of less than 2:1. A methylating agent is reacted with succinate at a temperature of from greater than 100° C. to about 400° C. to produce N-methyl succinimide which is purified and hydrogenated to form NMP.
    Type: Grant
    Filed: July 1, 2011
    Date of Patent: August 6, 2013
    Assignee: Battelle Memorial Institute
    Inventors: Todd A. Werpy, John G. Frye, Jr., James F. White, Johnathan E. Holladay, Alan H. Zacher
  • Publication number: 20110306780
    Abstract: 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: Application
    Filed: June 30, 2011
    Publication date: December 15, 2011
    Inventors: Michael A. Lilga, Richard T. Hallen, Todd A. Werpy, James F. White, Johnathan E. Holladay, John G. Frye, JR., Alan H. Zacher
  • Publication number: 20110263874
    Abstract: The invention includes methods of processing an initial di-carbonyl compound by conversion to a cyclic compound. The cyclic compound is reacted with an alkylating agent to form a derivative having an alkylated ring nitrogen. The invention encompasses a method of producing an N-alkyl product. Ammonia content of a solution is adjusted to produce a ratio of ammonia to di-carboxylate compound of from about 1:1 to about 1.5:1. An alkylating agent is added and the initial compound is alkylated and cyclized. The invention includes methods of making N-methyl pyrrolidinone (NMP). Aqueous ammonia and succinate is introduced into a vessel and ammonia is adjusted to provide a ratio of ammonia to succinate of less than 2:1. A methylating agent is reacted with succinate at a temperature of from greater than 100° C. to about 400° C. to produce N-methyl succinimide which is purified and hydrogenated to form NMP.
    Type: Application
    Filed: July 1, 2011
    Publication date: October 27, 2011
    Inventors: Todd A. Werpy, John G. Frye, JR., James F. White, Johnathan E. Holladay, Alan H. Zacher
  • Publication number: 20110257419
    Abstract: 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: Application
    Filed: June 30, 2011
    Publication date: October 20, 2011
    Inventors: Michael A. Lilga, Richard T. Hallen, Todd A. Werpy, James F. White, Johnathan E. Holladay, John G. Frye, JR., Alan H. Zacher
  • Patent number: 7994347
    Abstract: 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: Grant
    Filed: June 8, 2007
    Date of Patent: August 9, 2011
    Assignee: Battelle Memorial Institute
    Inventors: Michael A. Lilga, Richard T. Hallen, Todd A. Werpy, James F. White, Johnathan E. Holladay, John G. Frye, Jr., Alan H. Zacher
  • Patent number: 7973177
    Abstract: The invention includes methods of processing an initial di-carbonyl compound by conversion to a cyclic compound. The cyclic compound is reacted with an alkylating agent to form a derivative having an alkylated ring nitrogen. The invention encompasses a method of producing an N-alkyl product. Ammonia content of a solution is adjusted to produce a ratio of ammonia to di-carboxylate compound of from about 1:1 to about 1.5:1. An alkylating agent is added and the initial compound is alkylated and cyclized. The invention includes methods of making N-methylpyrrolidinone (NMP). Aqueous ammonia and succinate is introduced into a vessel and ammonia is adjusted to provide a ratio of ammonia to succinate of less than 2:1. A methylating agent is reacted with succinate at a temperature of from greater than 100° C. to about 400° C. to produce N-methyl succinimide which is purified and hydrogenated to form NMP.
    Type: Grant
    Filed: February 9, 2010
    Date of Patent: July 5, 2011
    Assignee: Battelle Memorial Institute
    Inventors: Todd A. Werpy, John G. Frye, Jr., James F. White, Johnathan E. Holladay, Alan H. Zacher
  • Patent number: 7939681
    Abstract: Methods are described for converting carbohydrates including, e.g., monosaccharides, disaccharides, and polysaccharides in ionic liquids to value-added chemicals including furans, useful as chemical intermediates and/or feedstocks. Fructose is converted to 5-hydroxylmethylfurfural (HMF) in the presence of metal halide and acid catalysts. Glucose is effectively converted to HMF in the presence of chromium chloride catalysts. Yields of up to about 70% are achieved with low levels of impurities such as levulinic acid.
    Type: Grant
    Filed: July 6, 2007
    Date of Patent: May 10, 2011
    Assignee: Battelle Memorial Institute
    Inventors: Haibo Zhao, Johnathan E. Holladay, Zongchao C. Zhang
  • Publication number: 20100317879
    Abstract: Methods are described for converting carbohydrates including, e.g., monosaccharides, disaccharides, and polysaccharides in ionic liquids to value-added chemicals including furans, useful as chemical intermediates and/or feedstocks. Fructose is converted to 5-hydroxylmethylfurfural (HMF) in the presence of metal halide and acid catalysts. Glucose is effectively converted to HMF in the presence of chromium chloride catalysts. Yields of up to about 70% are achieved with low levels of impurities such as levulinic acid.
    Type: Application
    Filed: August 24, 2010
    Publication date: December 16, 2010
    Applicant: BATTELLE MEMORIAL INSTITUTE
    Inventors: Haibo Zhao, Johnathan E. Holladay, Zongchao C. Zhang
  • Patent number: 7772412
    Abstract: The invention includes a method of dehydration of a sugar using a dehydration catalyst and a co-catalyst within a reactor. A sugar is introduced and H2 is flowed through the reactor at a pressure of less than or equal to about 300 psig to convert at least some of the sugar into an anhydrosugar product. The invention includes a process for producing isosorbide. A starting material comprising sorbitol is flowed into a reactor. H2 is counter flowed through the reactor. The starting material is exposed to a catalyst in the presence of a co-catalyst which comprises at least one metal. The exposing is conducted at a hydrogen pressure of less than or equal to 300 psig within the reactor and the hydrogen removes at least some of any water present during the exposing and inhibits formation of colored byproducts.
    Type: Grant
    Filed: January 26, 2006
    Date of Patent: August 10, 2010
    Assignee: Battelle Memorial Institute
    Inventors: Johnathan E. Holladay, Jianli Hu, Xinjie Zhang, Yong Wang
  • Publication number: 20100145072
    Abstract: The invention includes methods of processing an initial di-carbonyl compound by conversion to a cyclic compound. The cyclic compound is reacted with an alkylating agent to form a derivative having an alkylated ring nitrogen. The invention encompasses a method of producing an N-alkyl product. Ammonia content of a solution is adjusted to produce a ratio of ammonia to di-carboxylate compound of from about 1:1 to about 1.5:1. An alkylating agent is added and the initial compound is alkylated and cyclized. The invention includes methods of making N-methylpyrrolidinone (NMP). Aqueous ammonia and succinate is introduced into a vessel and ammonia is adjusted to provide a ratio of ammonia to succinate of less than 2:1. A methylating agent is reacted with succinate at a temperature of from greater than 100° C. to about 400° C. to produce N-methyl succinimide which is purified and hydrogenated to form NMP.
    Type: Application
    Filed: February 9, 2010
    Publication date: June 10, 2010
    Applicant: BATTELLE MEMORIAL INSTITUTE
    Inventors: Todd A. Werpy, John G. Frye, JR., James F. White, Johnathan E. Holladay, Alan H. Zacher
  • Patent number: 7728156
    Abstract: The invention includes a method of treating a solid acid catalyst. After exposing the catalyst to a mixture containing a sugar alcohol, the catalyst is washed with an organic solvent and is then exposed to a second reaction mixture. The invention includes a process for production of anhydrosugar alcohol. A solid acid catalyst is provided to convert sugar alcohol in a first sample to an anhydrosugar alcohol. The catalyst is then washed with an organic solvent and is subsequently utilized to expose a second sample. The invention includes a method for selective production of an anhydrosugar. A solid acid catalyst is provided within a reactor and anhydrosugar alcohol is formed by flowing a starting sugar alcohol into the reactor. The acid catalyst is then exposed to an organic solvent which allows a greater amount of additional anhydrosugar to be produced than would occur without exposing the acid catalyst to the organic solvent.
    Type: Grant
    Filed: January 26, 2006
    Date of Patent: June 1, 2010
    Assignee: Battelle Memorial Institute
    Inventors: Jianli Hu, Johnathan E. Holladay, Xinjie Zhang, Yong Wang
  • Patent number: 7687661
    Abstract: 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: Grant
    Filed: March 15, 2006
    Date of Patent: March 30, 2010
    Assignee: Battelle Memorial Institute
    Inventors: Michael A. Lilga, James F. White, Johnathan E. Holladay, Alan H. Zacher, Danielle S. Muzatko, Rick J. Orth
  • Patent number: 7674916
    Abstract: The invention includes methods of processing an initial di-carbonyl compound by conversion to a cyclic compound. The cyclic compound is reacted with an alkylating agent to form a derivative having an alkylated ring nitrogen. The invention encompasses a method of producing an N-alkyl product. Ammonia content of a solution is adjusted to produce a ratio of ammonia to di-carboxylate compound of from about 1:1 to about 1.5:1. An alkylating agent is added and the initial compound is alkylated and cyclized. The invention includes methods of making N-methyl pyrrolidinone (NMP). Aqueous ammonia and succinate is introduced into a vessel and ammonia is adjusted to provide a ratio of ammonia to succinate of less than 2:1. A methylating agent is reacted with succinate at a temperature of from greater than 100° C. to about 400° C. to produce N-methyl succinimide which is purified and hydrogenated to form NMP.
    Type: Grant
    Filed: March 19, 2007
    Date of Patent: March 9, 2010
    Assignee: Battelle Memorial Institute
    Inventors: Todd A. Werpy, John G. Frey, Jr., James F. White, Johnathan E. Holladay, Alan H. Zacher
  • Patent number: 7649099
    Abstract: The invention includes methods of producing dianhydrosugars. A polyol is reacted in the presence of a first catalyst to form a monocyclic sugar. The monocyclic sugar is transferred to a second reactor where it is converted to a dianhydrosugar alcohol in the presence of a second catalyst. The invention includes a process of forming isosorbide. An initial reaction is conducted at a first temperature in the presence of a solid acid catalyst. The initial reaction involves reacting sorbitol to produce 1,4-sorbitan, 3,6-sorbitan, 2,5-mannitan and 2,5-iditan. Utilizing a second temperature, the 1,4-sorbitan and 3,6-sorbitan are converted to isosorbide. The invention includes a method of purifying isosorbide from a mixture containing isosorbide and at least one additional component. A first distillation removes a first portion of the isosorbide from the mixture. A second distillation is then conducted at a higher temperature to remove a second portion of isosorbide from the mixture.
    Type: Grant
    Filed: January 26, 2006
    Date of Patent: January 19, 2010
    Assignee: Battelle Memorial Institute
    Inventors: Johnathan E. Holladay, Jianli Hu, Yong Wang, Todd A. Werpy, Xinjie Zhang
  • Patent number: 7615652
    Abstract: The invention includes methods for producing dianhydrosugar alcohol by providing an acid catalyst within a reactor and passing a starting material through the reactor at a first temperature. At least a portion of the staring material is converted to a monoanhydrosugar isomer during the passing through the column. The monoanhydrosugar is subjected to a second temperature which is greater than the first to produce a dianhydrosugar. The invention includes a method of producing isosorbide. An initial feed stream containing sorbitol is fed into a continuous reactor containing an acid catalyst at a temperature of less than 120° C. The residence time for the reactor is less than or equal to about 30 minutes. Sorbitol converted to 1,4-sorbitan in the continuous reactor is subsequently provided to a second reactor and is dehydrated at a temperature of at least 120° C. to produce isosorbide.
    Type: Grant
    Filed: January 26, 2006
    Date of Patent: November 10, 2009
    Assignee: Battelle Memorial Institute
    Inventors: Johnathan E. Holladay, Jianli Hu, Yong Wang, Todd A. Werpy
  • Publication number: 20090264687
    Abstract: Hydrogenolysis systems are provided that can include a reactor housing an Ru-comprising hydrogenolysis catalyst and wherein the contents of the reactor is maintained at a neutral or acidic pH. Reactant reservoirs within the system can include a polyhydric alcohol compound and a base, wherein a weight ratio of the base to the compound is less than 0.05. Systems also include the product reservoir comprising a hydrogenolyzed polyhydric alcohol compound and salts of organic acids, and wherein the moles of base are substantially equivalent to the moles of salts or organic acids. Processes are provided that can include an Ru-comprising catalyst within a mixture having a neutral or acidic pH. A weight ratio of the base to the compound can be between 0.01 and 0.05 during exposing.
    Type: Application
    Filed: April 16, 2008
    Publication date: October 22, 2009
    Inventors: Johnathan E. Holladay, Danielle S. Muzatko, James F. White, Alan H. Zacher