Patents by Inventor Benjamin G. Harvey

Benjamin G. Harvey 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: 11118124
    Abstract: A diamondoid fuel comprising a cage structure including 10, 14, 18, or 22 carbons. The diamondoid fuel also includes one of one to four cyclopropyl groups bonded to the cage structure or two to four functional groups bonded to the cage structure where the functional groups are an alkyl group, an allyl group, a cyclopropyl group, or combinations thereof. Additionally, at least one functional group is an allyl group and at least one functional group is a cyclopropyl group.
    Type: Grant
    Filed: October 7, 2019
    Date of Patent: September 14, 2021
    Assignee: The United States of America, as Represented by the Secretary of the Navy
    Inventors: Benjamin G. Harvey, Matthew C. Davis
  • Patent number: 11117847
    Abstract: In the present method a reaction mixture is comprised of a source of adamantane, mixed with an alkane or cycloalkane. A Lewis acid catalyst is added to the reaction mixture which is heated and then purified. The resulting alkyl diamondoid mixtures have significantly higher densities and volumetric net heats of combustion while maintaining low viscosities which allow for use at low temperature.
    Type: Grant
    Filed: March 29, 2019
    Date of Patent: September 14, 2021
    Assignee: The United States of America, as Represented by the Secretary of the Navy
    Inventor: Benjamin G. Harvey
  • Patent number: 11078139
    Abstract: A method for making cyclopentadiene fuels comprising producing cyclopent-2-en-1-one or a mixture of cyclopent-2-en-1-one from a bio-based source. The cyclopent-2-en-1-one or the mixture of cyclopent-2-en-1-one is hydrogenated, thereby forming cyclopent-2-en-1-ol or a mixture of cyclopent-2-en-1-ol. The cyclopent-2-en-1-ol or the mixture of cyclopent-2-en-1-ol is dehydrated with a dehydrating agent, thereby forming cyclopentadiene or a mixture of cyclopentadiene. The cyclopentadiene or mixture of cyclopentadiene is converted to dicyclopentadiene or dihydrodicyclopentadiene. The dicyclopentadiene or dihydrodicyclopentadiene is hydrogenated, thereby forming tetrahydrodicyclopentadiene. The tetrahydrodicyclopentadiene is isomerized, thereby forming exo-tetrahydrodicyclopentadiene.
    Type: Grant
    Filed: September 4, 2019
    Date of Patent: August 3, 2021
    Assignee: The United States of America, as represented by the Secretary of the Navy
    Inventor: Benjamin G. Harvey
  • Patent number: 11027996
    Abstract: A method for making crown ether functionalized substrates, which includes modifying crown ether-based molecules by reacting with carboxylic acid functionalize chains. The crown ether-based molecules are then attached to substrates, thereby forming crown ether functionalized substrates.
    Type: Grant
    Filed: January 23, 2019
    Date of Patent: June 8, 2021
    Assignee: The United States of America, as Represented by the Secretary of the Navy
    Inventors: Gregory Stephen Ostrom, Benjamin G Harvey
  • Patent number: 10981846
    Abstract: A method for making a fuel includes reacting a conjugated diene or a mixture of conjugated dienes with a catalyst selected from the group consisting of a low valent iron catalyst stabilized with a pyridineimine ligand, an iron precatalyst coordinated to the pyridineimine ligand that is activated with a reducing agent, a low oxidation state Fe complex stabilized with a pyridineimine ligand and a coordinating ligand, and combinations thereof, thereby forming a substituted cyclooctadiene. The substituted cyclooctadiene is then hydrogenated, thereby forming cyclooctane fuel.
    Type: Grant
    Filed: August 16, 2019
    Date of Patent: April 20, 2021
    Assignees: The United States of America, as Represented by the Secretary of the Navy, The Trustees of Princeton University
    Inventors: Benjamin G. Harvey, Kyle E. Rosenkoetter, Paul Chirik, C. Rose Kennedy
  • Patent number: 10913898
    Abstract: This invention describes resins with phosphate cores and a simple, three-step process for their synthesis. Preferred resins are cyanate ester resins with bridging phosphate groups. These resins can be cured to produce thermoset polymers having Tgs of between 131 and >360° C. depending on the number of cyanate ester groups per phosphate and the substitution pattern of the aromatic rings. The high char yields of these resins, up to about 67%, coupled with the phosphate core means that these materials will have applications as fire-resistant polymers. Additionally, these materials can potentially be blended with conventional cyanate esters or other compatible thermosetting resins to improve the fire resistance of composite materials. Other applications may include use in fire-resistant circuit boards, or as surface coatings to reduce flammability of conventional composite materials or thermoplastics.
    Type: Grant
    Filed: November 1, 2018
    Date of Patent: February 9, 2021
    Assignee: The United States of America as Represented by the Secretary of the Navy
    Inventors: Benjamin G. Harvey, Andrew P. Chafin, Michael D. Garrison
  • Patent number: 10710941
    Abstract: A diamondoid fuel comprising a cage structure including 10, 14, 18, or 22 carbons. The diamondoid fuel also includes one of one to four cyclopropyl groups bonded to the cage structure or two to four functional groups bonded to the cage structure where the functional groups are an alkyl group, an allyl group, a cyclopropyl group, or combinations thereof. Additionally, at least one functional group is an allyl group and at least one functional group is a cyclopropyl group.
    Type: Grant
    Filed: November 1, 2018
    Date of Patent: July 14, 2020
    Assignee: The United States of America, as represented by the Secretary of the Navy
    Inventors: Benjamin G. Harvey, Matthew C. Davis
  • Patent number: 10711215
    Abstract: A method to generate dioxolanes from renewable feedstocks, and more specifically, these oxygenated hydrocarbons can be used as gasoline-range fuels and diesel additives.
    Type: Grant
    Filed: August 24, 2015
    Date of Patent: July 14, 2020
    Assignee: The Government of the United States of America as represented by the Secretary of the Navy
    Inventors: Benjamin G. Harvey, Heather A. Meylemans
  • Patent number: 10669400
    Abstract: A method for preparing fire resistant polymeric materials including, providing at least one first polyphenol having three or more phenolic groups, reacting at least one first polyphenol having three or more phenolic groups with at least one halophosphate and at least one first base to produce at least one second phenol having at least one phosphate group, and converting at least one second phenol having at least one phosphate group to a thermoplastic or thermosetting fire resistant polymeric material.
    Type: Grant
    Filed: November 15, 2017
    Date of Patent: June 2, 2020
    Assignee: The United States of America, as Represented by the Secretary of the Navy
    Inventors: Benjamin G Harvey, Matthew C Davis
  • Patent number: 10604711
    Abstract: A method for making an alkyl cyclobutane fuel, which includes obtaining a solution of at least one alpha olefin. A catalyst is added to the solution, thereby generating a mixture of dimers. The mixture is hydrogenated, thereby converting the dimers to hydrogenated dimers. The mixture is purified to produce an alkyl cyclobutane fuel.
    Type: Grant
    Filed: August 9, 2018
    Date of Patent: March 31, 2020
    Assignee: The United States of America, as Represented by the Secretary of the Navy
    Inventors: Benjamin G. Harvey, David Morris
  • Patent number: 10323198
    Abstract: A process for making high density fuels having the potential to increase the range and/or loiter time of Navy platforms. Derivation of these fuels from a sustainable source will decrease the carbon footprint of the Department of Defense (DoD) and reduce reliance on nonsustainable petroleum sources. Fuels based on ziza-anes have volumetric net heats of combustion up to ca. 18% higher than conventional Navy jet fuel (JP-5). Moreover, ziza-anes can be generated from sustainable biomass sugars via fermentation.
    Type: Grant
    Filed: October 21, 2015
    Date of Patent: June 18, 2019
    Assignee: The United States of America as Represented by the Secretary of the Navy
    Inventor: Benjamin G Harvey
  • Patent number: 10287237
    Abstract: A method for converting vanillin to bis(cyanate) ester monomers, comprising treating vanillin with a reductive coupling agent to form at least one olefin. The olefin or olefins are treated with hydrogen and a metal catalyst to hydrogenate said olefin. The hydrogenated olefin or olefins are treated with at least one cyanogen halide and a base in an organic solvent to afford at least one olefin monomer. The olefin monomer or monomers are purified by recrystallization or precipitation from an organic solvent.
    Type: Grant
    Filed: October 12, 2017
    Date of Patent: May 14, 2019
    Assignee: The United States of America, as Represented by the Secretary of the Navy
    Inventors: Michael E. Wright, Benjamin G. Harvey
  • Patent number: 10253336
    Abstract: A process for making high density fuels having the potential to increase the range and/or loiter time of Navy platforms. Derivation of these fuels from a sustainable source will decrease the carbon footprint of the Department of Defense (DoD) and reduce reliance on nonsustainable petroleum sources. Fuels based on longifolene have volumetric net heats of combustion up to 17% higher than conventional Navy jet fuel (JP-5). Moreover, longifolene can be generated from sustainable biomass sugars via fermentation.
    Type: Grant
    Filed: October 21, 2015
    Date of Patent: April 9, 2019
    Assignee: The United States of America as Represented by the Secretary of the Navy
    Inventor: Benjamin G Harvey
  • Patent number: 10252966
    Abstract: A series of renewable bisphenols has been synthesized from creosol (2-methoxy-4-methylphenol) through stoichiometric condensation with short chain aldehydes. Creosol can be readily produced from lignin, potentially allowing for the large scale synthesis of bisphenol A replacements from abundant waste biomass. The renewable bisphenols were isolated in good yield and purity without resorting to solvent intense purification methods. Zinc acetate was shown to be selective catalyst for ortho-coupling of formaldehyde but was unreactive with more sterically demanding aldehydes. Dilute HCl and HBr solutions were shown to be effective catalysts for the selective coupling of aldehydes in the position meta to the phenol. Acid solutions could be recycled and used multiple times without decreases in activity or yield.
    Type: Grant
    Filed: April 11, 2013
    Date of Patent: April 9, 2019
    Assignee: The United States of America as Represented by the Secretary of the Navy
    Inventors: Benjamin G. Harvey, Heather A. Meylemans
  • Patent number: 10246655
    Abstract: A process for making high density fuels having the potential to increase the range and/or loiter time of Navy platforms. Derivation of these fuels from a sustainable source will decrease the carbon footprint of the Department of Defense (DoD) and reduce reliance on nonsustainable petroleum sources. Fuels based on santalenes have volumetric energy densities greater than JP-5 and F-76 and can be produced from biomass sugars.
    Type: Grant
    Filed: October 21, 2015
    Date of Patent: April 2, 2019
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: Benjamin G Harvey
  • Patent number: 10246654
    Abstract: A process for making high density fuels having the potential to increase the range and/or loiter time of Navy platforms. Derivation of these fuels from a sustainable source will decrease the carbon footprint of the Department of Defense (DoD) and reduce reliance on nonsustainable petroleum sources. Fuels based on barbatene and thujopsene have volumetric energy densities comparable to JP-10 and can be produced from biomass sugars.
    Type: Grant
    Filed: October 21, 2015
    Date of Patent: April 2, 2019
    Assignee: The United States of America as Represented by the Secretary of the Navy
    Inventor: Benjamin G Harvey
  • Patent number: 10155906
    Abstract: This invention describes resins with phosphate cores and a simple, three-step process for their synthesis. Preferred resins are cyanate ester resins with bridging phosphate groups. These resins can be cured to produce thermoset polymers having Tgs of between 131 and >360° C. depending on the number of cyanate ester groups per phosphate and the substitution pattern of the aromatic rings. The high char yields of these resins, up to about 67%, coupled with the phosphate core means that these materials will have applications as fire-resistant polymers. Additionally, these materials can potentially be blended with conventional cyanate esters or other compatible thermosetting resins to improve the fire resistance of composite materials. Other applications may include use in fire-resistant circuit boards, or as surface coatings to reduce flammability of conventional composite materials or thermoplastics.
    Type: Grant
    Filed: September 6, 2016
    Date of Patent: December 18, 2018
    Assignee: The United States of America as Represented by the Secretary of the Navy
    Inventors: Benjamin G. Harvey, Andrew P. Chafin, Michael D. Garrison
  • Patent number: 10113130
    Abstract: High density renewable diesel and jet fuels have been generated by blending multicyclic sesquiterpanes with a synthetic paraffinic kerosene (5-methylundecane). The sesquiterpanes impart high density and volumetric net heat of combustion to the blends, while inclusion of the modestly branched paraffin decreases the viscosity and increases the cetane number of the blends. A surrogate diesel fuel including 65% sesquiterpanes and 35% 5-methylundecane had a cetane number of 45.7, a density of 0.853 g/ml, and a volumetric net heat of combustion (NHOC) of 133,593 btu/gal. By increasing the amount of paraffin to 60% by volume, a jet fuel surrogate was prepared with a cetane number of 57.0, a density of 0.806 g/ml, a ?20° C. viscosity of 7.9 est, and a NHOC of 124,257 btu/gal. The results show that full-performance and even ultra-performance fuels can be generated by combining bio-derived sesquiterpanes and paraffins.
    Type: Grant
    Filed: February 29, 2016
    Date of Patent: October 30, 2018
    Assignee: The United States of America, as Represented by the Secretary of the Navy
    Inventor: Benjamin G Harvey
  • Patent number: 10106475
    Abstract: A method for converting cedarwood oil into high density fuels including, hydrogenating cedarwood oil in the presence of at least one hydrogenation catalyst to generate hydrogenated cedarwood oil, removing the hydrogenation catalyst from the hydrogenated cedarwood oil, purifying the hydrogenated cedarwood oil to produce a first high density fuel, isomerizing the first high density fuel in the presence of at least one acid catalyst to generate a hydrocarbon mixture including adamantanes, and distilling the adamantane mixture to produce a second alkyl-adamantane high density fuel.
    Type: Grant
    Filed: August 18, 2017
    Date of Patent: October 23, 2018
    Assignee: The United States of America as Represented by the Secretary of the Navy
    Inventors: Benjamin G. Harvey, Kale Warren Harrison
  • Patent number: 10053643
    Abstract: A process for making high density fuels having the potential to increase the range and/or loiter time of Navy platforms. Derivation of these fuels from a sustainable source will decrease the carbon footprint of the Department of Defense (DoD) and reduce reliance on nonsustainable petroleum sources. Fuels derived from bisabolene can have volumetric net heats of combustion comparable to JP-10 and can be produced from biomass sugars.
    Type: Grant
    Filed: October 21, 2015
    Date of Patent: August 21, 2018
    Assignee: The United States of America as Represented by the Secretary of the Navy
    Inventor: Benjamin G Harvey