High density turbine and diesel fuels derived from adamantane

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  • Publication Date:
    September 14, 2021
  • Additional Information
    • Patent Number:
      11117,847
    • Appl. No:
      16/369829
    • Application Filed:
      March 29, 2019
    • 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.
    • Inventors:
      The United States of America, as Represented by the Secretary of the Navy (Arlington, VA, US)
    • Assignees:
      The United States of America, as Represented by the Secretary of the Navy (Washington, DC, US)
    • Claim:
      1. A method for synthesizing an alkyl-adamantane mixture, comprising: providing a reaction mixture of a source of adamantane with at least one alkane and a Lewis acid catalyst; reacting the mixture by heating the reaction mixture to produce a mixture of alkyl adamantanes; removing unreacted at least one alkane by distillation; and removing unreacted adamantane via distillation, sublimation, or crystallization.
    • Claim:
      2. The method according to claim 1 , wherein said source of adamantane comprises adamantane, one or more alkyl adamantanes, or combinations thereof.
    • Claim:
      3. The method according to claim 1 , wherein said at least one alkane is an alkane or cycloalkane having from 2-40 carbon atoms.
    • Claim:
      4. The method according to claim 3 , wherein said at least one alkane is n-hexane, n-heptane, n-octane, n-nonane, or n-decane.
    • Claim:
      5. The method according to claim 1 , wherein said at least one alkane is selected from the group consisting of mineral spirits, naphtha, petroleum ether, kerosene, diesel fuel, vegetable derived triglycerides, animal derived triglycerides, vegetable derived fatty acids, animal derived fatty acids, methyl esters, synthetic paraffinic kerosenes, hydrotreated fatty acids, hydrotreated esters, and mixtures thereof.
    • Claim:
      6. The method according to claim 1 , wherein the molar ratio of said at least one alkane:source of adamantane in the mixture is from about 2:1 to about 5:1.
    • Claim:
      7. The method according to claim 1 , wherein the Lewis acid catalyst is present in the amount of from about 0.001-50 mol %.
    • Claim:
      8. The method according to claim 7 , wherein the Lewis acid catalyst is AlCl 3 , AlBr 3 , AlI 3 , metal triflates or metalloid triflates.
    • Claim:
      9. The method according to claim 7 , wherein the Lewis acid catalyst is a heterogeneous acid.
    • Claim:
      10. The method according to claim 7 , wherein the Lewis acid catalyst is a Lewis acidic ionic liquid.
    • Claim:
      11. The method according to claim 1 , wherein the reaction mixture is heated at a temperature ranging between about ambient and about 200 degrees C.
    • Claim:
      12. The method according to claim 1 , wherein the reaction mixture is heated for a time period from about 10 minutes to about 7 days.
    • Claim:
      13. The method according to claim 1 , further comprising refining the alkyl adamantane mixture by fractional distillation to yield high density fuel blends.
    • Claim:
      14. An alkyl adamantane mixture produced by the method of claim 1 .
    • Claim:
      15. The alkyl adamantane mixture of claim 14 having a cetane number greater than about 40.
    • Claim:
      16. The alkyl adamantane mixture of claim 14 comprising an alkyl adamantanes of C10-C12, C10-C13, C10-C14, C10-C15, C10-C16, or C10-C17.
    • Claim:
      17. The alkyl adamantane mixture of claim 14 having a density from about 0.90 to about 0.94 g/mL.
    • Claim:
      18. The alkyl adamantane mixture of claim 14 having a volumetric net heat of combustion greater than or equal to about 135.0 kBtu/gal.
    • Claim:
      19. A high density fuel comprised of about 1% to about 70% of at least one alkyl-adamantane mixture of claim 14 .
    • Claim:
      20. The high density fuel of claim 19 having density of at least 0.775 g/mL and a NHOC of at least 120,000 Btu/gal.
    • Patent References Cited:
      3382288 May 1968 Schneider
      3646233 February 1972 Moore
      3928480 December 1975 Tabushi
      5043503 August 1991 Del Rossi
      5345020 September 1994 Shen
      2008/0319241 December 2008 Huang
      2015/0011810 January 2015 Harvey
      2015/0344385 December 2015 Huang
    • Primary Examiner:
      Fadhel, Ali Z
    • Attorney, Agent or Firm:
      Naval Air Warfare Center Weapons Division
      Nissim, Stuart H.
    • Accession Number:
      edspgr.11117847