Patents by Inventor Herman P. Benecke

Herman P. Benecke 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: 11466217
    Abstract: A process of producing a distillate fuel from coal includes: preparing a biomass-derived coal solvent; dissolving the coal in the biomass-derived solvent; and separating undissolved coal and mineral matter to produce a syncrude. In certain embodiments, the process further includes subjecting the syncrude to a hydrotreatment/hydrogenation process to produce a distillate fuel. In certain embodiments, the biomass-derived solvent is a hydrogen-donor solvent. A method to improve direct coal liquefaction includes: using a non-hydrogenated lipid in a direct coal liquefaction process to facilitate coal depolymerization. In certain embodiments, the lipid is a polyunsaturated biobased oil. A method for using a biomass-derived feedstock as a hydrogen donor includes: providing a biomass-derived feedstock; modifying the feedstock to improve its usefulness as a hydrogen donor; and conducting a transfer hydrogenation process using the modified feedstock as a hydrogen donor.
    Type: Grant
    Filed: September 19, 2016
    Date of Patent: October 11, 2022
    Assignee: Battelle Memorial Institute
    Inventors: Satya P. Chauhan, Daniel B. Garbark, Herman P. Benecke, H. Nicholas Conkle
  • Patent number: 10731105
    Abstract: A method for producing a triglyceride including fatty acids with vicinal diesters: (a) providing a triglyceride including fatty acids with epoxide groups; (b) reacting the epoxide groups with carboxylic acid salts under basic conditions to produce a triglyceride including fatty acids with vicinal ester/alkoxides; (c) protonating the vicinal ester/alkoxides to produce a triglyceride including fatty acids with vicinal ester/alcohols; and (d) reacting the vicinal ester/alcohols with carboxylic acids under acidic conditions to produce a triglyceride including fatty acids with vicinal diesters.
    Type: Grant
    Filed: May 31, 2016
    Date of Patent: August 4, 2020
    Assignee: Battelle Memorial Institute
    Inventors: Herman P. Benecke, Daniel B. Garbark
  • Publication number: 20190153328
    Abstract: A process of producing a distillate fuel from coal includes: preparing a biomass-derived coal solvent; dissolving the coal in the biomass-derived solvent; and separating undissolved coal and mineral matter to produce a syncrude. In certain embodiments, the process further includes subjecting the syncrude to a hydrotreatment/hydrogenation process to produce a distillate fuel. In certain embodiments, the biomass-derived solvent is a hydrogen-donor solvent. A method to improve direct coal liquefaction includes: using a non-hydrogenated lipid in a direct coal liquefaction process to facilitate coal depolymerization. In certain embodiments, the lipid is a polyunsaturated biobased oil. A method for using a biomass-derived feedstock as a hydrogen donor includes: providing a biomass-derived feedstock; modifying the feedstock to improve its usefulness as a hydrogen donor; and conducting a transfer hydrogenation process using the modified feedstock as a hydrogen donor.
    Type: Application
    Filed: September 19, 2016
    Publication date: May 23, 2019
    Inventors: SATYA P. CHAUHAN, DANIEL B. GARBARK, HERMAN P. BENECKE, H. Nicholas Conkle
  • Patent number: 10125079
    Abstract: Unique methods have been developed to convert polysaccharides into value-added products, such as levulinic acid and alkyl levulinates. The polysaccharides are heated in the presence of water, an alcohol, and an acid to cleave the polysaccharide, and the resulting monosacchrides or monosaccharide acetals or both are contacted with an acid in the presence of an alcohol at a higher temperature. Useful acids include Brønsted acid catalysts and Lewis acid catalysts including mineral acids, metal halides, immobilized heterogeneous catalysts functionalized with a Brønsted acid group or a Lewis acid group, or combinations thereof.
    Type: Grant
    Filed: January 11, 2017
    Date of Patent: November 13, 2018
    Assignee: Battelle Memorial Institute
    Inventors: Herman P. Benecke, Daniel B. Garbark
  • Publication number: 20180216028
    Abstract: A method for producing a triglyceride including fatty acids with vicinal diesters: (a) providing a triglyceride including fatty acids with epoxide groups; (b) reacting the epoxide groups with carboxylic acid salts under basic conditions to produce a triglyceride including fatty acids with vicinal ester/alkoxides; (c) protonating the vicinal ester/alkoxides to produce a triglyceride including fatty acids with vicinal ester/alcohols; and (d) reacting the vicinal ester/alcohols with carboxylic acids under acidic conditions to produce a triglyceride including fatty acids with vicinal diesters.
    Type: Application
    Filed: May 31, 2016
    Publication date: August 2, 2018
    Inventors: Herman P. Benecke, Daniel B. Garbark
  • Publication number: 20180194711
    Abstract: Unique methods have been developed to convert polysaccharides into value-added products, such as levulinic acid and alkyl levulinates. The polysaccharides are heated in the presence of water, an alcohol, and an acid to cleave the polysaccharide, and the resulting monosacchrides or monosaccharide acetals or both are contacted with an acid in the presence of an alcohol at a higher temperature. Useful acids include Brønsted acid catalysts and Lewis acid catalysts including mineral acids, metal halides, immobilized heterogeneous catalysts functionalized with a Brønsted acid group or a Lewis acid group, or combinations thereof.
    Type: Application
    Filed: January 11, 2017
    Publication date: July 12, 2018
    Inventors: Herman P. Benecke, Daniel B. Garbark
  • Publication number: 20170044090
    Abstract: This invention relates to a ring opening method. The method includes reacting an epoxidized fatty acid ester with an alcohol to open an epoxy ring of the ester. A salt of tetrafluoroboric acid is used as a catalyst in the reaction. In another embodiment, the invention relates to a method of producing a polyurethane. An epoxidized fatty acid ester is reacted with an alcohol to open an epoxy ring of the ester, thereby to produce a polyol. A salt of tetrafluoroboric acid is used as a catalyst in the reaction. The polyol is then reacted with an isocyanate to produce a polyurethane. In a further embodiment, the polyol is used to produce a product selected from polyurethanes, coatings, adhesives, sealants, elastomers and lubricants.
    Type: Application
    Filed: October 29, 2014
    Publication date: February 16, 2017
    Applicant: Solazyme, Inc.
    Inventors: Herman P. Benecke, Jeffrey T. Cafmeyer, Daniel B. Garbark
  • Publication number: 20160168475
    Abstract: Systems, methods, and apparatuses are provided for upgrading a bio-oil by reaction with an olefin in the presence of a catalyst. For example, upgraded bio-oil may have improved miscibility with hydrophobic fuels.
    Type: Application
    Filed: July 8, 2014
    Publication date: June 16, 2016
    Inventors: Zia Abdullah, Herman P. Benecke, Daniel B. Garbark, Rachid Taha
  • Publication number: 20160145285
    Abstract: Methods are provided for producing bio-oil polyols, alkoxylating bio-oil polyols to provide polyols, and for employing the alkoxylated bio-oil polyols for making polymers or copolymers of polyesters or polyurethanes. Compositions and methods are provided for incorporating bio-oils into phenolic resins such as phenol-formaldehyde resin and phenol-formaldehyde-urea resin, as well as hot melt adhesive compositions.
    Type: Application
    Filed: June 11, 2014
    Publication date: May 26, 2016
    Inventors: Daniel B. Garbark, Herman P. Benecke, Megan S. Moore, Mark J. Perry, Jeffrey T. Cafmeyer
  • Patent number: 9290698
    Abstract: The invention provides for new flame retardant non-furan dicarboxylic acid (FDCA) based polyols; oligomers and polymers made from these new polyols with flame retardation properties; and methods of using them as a part or all of the flame retardation composition/material, such as foams and binders.
    Type: Grant
    Filed: July 15, 2011
    Date of Patent: March 22, 2016
    Assignee: Battelle Memorial Institute
    Inventors: Herman P. Benecke, Daniel B. Garbark
  • Publication number: 20160032196
    Abstract: Vapor phase catalytic reactors and methods for using the same for upgrade of fuels produced by fast pyrolysis of biomass are disclosed.
    Type: Application
    Filed: March 15, 2014
    Publication date: February 4, 2016
    Inventors: Zia Abdullah, Slawomir Winecki, G. Bradley Chadwell, Michael A. O'Brian, Russell K. Smith, Stephanie Flamberg, James E. Dvorsky, Rachid Taha, James E. Mathis, Herman P. Benecke, Daniel B. Garbark
  • Publication number: 20150045576
    Abstract: Unique methods have been developed to convert saccharides into value-added products such as alkyl lactates, lactic acid, alkyl levulinates, levulinic acid, and optionally alkyl formate esters and/or hydroxymethylfurfural (HMF). Useful catalysts include Lewis acid catalysts and Brønsted acid catalysts including mineral acids, metal halides, immobilized heterogeneous catalysts functionalized with a Brønsted acid group or a Lewis acid group, or combinations thereof. The saccharides are contacted with the catalyst in the presence of various alcohols.
    Type: Application
    Filed: August 6, 2014
    Publication date: February 12, 2015
    Inventors: Herman P. Benecke, Daniel Garbark
  • Patent number: 8940914
    Abstract: Disclosed are compositions and methods for the production of mono-esters and di-esters from the reaction of HMF and a reactant selected from a diacid or a diacid derivative; typical reactants are PAN, phthaloyl dichloride, dimethyl phthalate, maleic acid, and maleic anhydride or mono-esters that can be prepared from HMF and MAN.
    Type: Grant
    Filed: July 20, 2012
    Date of Patent: January 27, 2015
    Assignee: Battelle Memorial Institute
    Inventors: Herman P. Benecke, Jerry L. King, II, Alex Walter Kawczak, Donald W. Zehnder, II, Erica E. Hirschl
  • Publication number: 20130150475
    Abstract: The invention provides for new flame retardant non-furan dicarboxylic acid (FDCA) based polyols; oligomers and polymers made from these new polyols with flame retardation properties; and methods of using them as a part or all of the flame retardation composition/material, such as foams and binders.
    Type: Application
    Filed: July 15, 2011
    Publication date: June 13, 2013
    Applicant: BATTELLE MEMORIAL INSTITUTE
    Inventors: Herman P. Benecke, Daniel B. Garbark
  • Patent number: 8378056
    Abstract: New polyols; oligomers, and polymers made from the polyols; and binders made from the new polyols, oligomers, or polymers that can be used in binders, where the binders typically include one or more polyols, and a polyfunctional acid or a polyfunctional nitrile.
    Type: Grant
    Filed: August 23, 2012
    Date of Patent: February 19, 2013
    Assignee: Battelle Memorial Institute
    Inventors: Herman P. Benecke, Daniel B. Garbark, Alex W. Kawczak, Michael C. Clingerman
  • Publication number: 20120316307
    Abstract: New polyols; oligomers, and polymers made from the polyols; and binders made from the new polyols, oligomers, or polymers that can be used in binders, where the binders typically include one or more polyols, and a polyfunctional acid or a polyfunctional nitrile.
    Type: Application
    Filed: August 23, 2012
    Publication date: December 13, 2012
    Applicant: Battelle Memorial Institute
    Inventors: Herman P. Benecke, Daniel B. Garbark, Alex W. Kawczak, Michael C. Clingerman
  • Patent number: 8309676
    Abstract: New polyols; oligomers, and polymers made from the polyols; and binders made from the new polyols, oligomers, or polymers that can be used in binders, where the binders typically include one or more polyols, and a polyfunctional acid or a polyfunctional nitrile.
    Type: Grant
    Filed: November 10, 2009
    Date of Patent: November 13, 2012
    Assignee: Battelle Memorial Institute
    Inventors: Herman P. Benecke, Daniel B. Garbark, Alex W. Kawczak, Michael C. Clingerman
  • Patent number: 8247582
    Abstract: Disclosed are compositions and methods for the production of mono-esters and di-esters from the reaction of HMF and a reactant selected from a diacid or a diacid derivative; typical reactants are PAN, phthaloyl dichloride, dimethyl phthalate, maleic acid, and maleic anhydride or mono-esters that can be prepared from HMF and MAN.
    Type: Grant
    Filed: February 7, 2007
    Date of Patent: August 21, 2012
    Assignee: Battelle Memorial Institute
    Inventors: Herman P. Benecke, Jerry L. King, II, Alex Walter Kawczak, Donald W. Zehnder, II, Erica E. Hirschl
  • Patent number: 8148501
    Abstract: Absorbent hydrogels are formed by reacting a protein meal base, a radical initiator and a polymerizable monomer. Optionally, a cross-linking agent and/or a radical accelerant, such as tetramethylethylenediamine (TMEDA) or sodium bisulfite (NaHSO3), is also added to the mixture. Preferably, the radical initiator is ammonium persulfate (APS) or potassium persulfate (KPS), and the cross-linking agent is preferably trifunctional trimethylolpropane trimethacrylate (TMPTMA) or methylene bis acrylamide (MBA). The polymerizable monomer is preferably acrylic acid, or a combination of acrylic acid and acrylamide. The as-formed hydrogel is washed in order to extract non-reactant components from the gel and then dried. The resultant absorbent and superabsorbent hydrogels have high water uptake ratios, and can be utilized for a variety of applications.
    Type: Grant
    Filed: February 23, 2009
    Date of Patent: April 3, 2012
    Assignee: Battelle Memorial Institute
    Inventors: Herman P. Benecke, Bhima R. Vijayendran, Kevin B. Spahr
  • Publication number: 20110028314
    Abstract: Absorbent hydrogels are formed by reacting a protein meal base, a radical initiator and a polymerizable monomer. Optionally, a cross-linking agent and/or a radical accelerant, such as tetramethylethylenediamine (TMEDA) or sodium bisulfite (NaHSO3), is also added to the mixture. Preferably, the radical initiator is ammonium persulfate (APS) or potassium persulfate (KPS), and the cross-linking agent is preferably trifunctional trimethylolpropane trimethacrylate (TMPTMA) or methylene bis acrylamide (MBA). The polymerizable monomer is preferably acrylic acid, or a combination of acrylic acid and acrylamide. The as-formed hydrogel is washed in order to extract non-reactant components from the gel and then dried. The resultant absorbent and superabsorbent hydrogels have high water uptake ratios, and can be utilized for a variety of applications.
    Type: Application
    Filed: February 23, 2009
    Publication date: February 3, 2011
    Applicant: BATTELLE MEMORIAL INSTITUTE
    Inventors: Herman P Benecke, Bhima R Vijayendran, Kevin B Spahr