Diamondoid fuels

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  • Publication Date:
    September 14, 2021
  • Additional Information
    • Patent Number:
      11118,124
    • Appl. No:
      16/595101
    • Application Filed:
      October 07, 2019
    • 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.
    • 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 making a diamondoid fuel, comprising: in a solvent comprising a chloroalkene solvent; reacting a halogenated diamondoid with allyl halogen in the presence of a Lewis acid, thereby forming a mixture of diamondoids including diamondoid substituted with alpha.gamma dihaloalkane, diamondoid substituted with beta.beta dihaloalkane, or a combination thereof; and reacting the mixture of diamondoids with one of i) a reducing metal or ii) a strong base, thereby removing halogens and forming the diamondoid fuel comprising diamondoid substituted with cyclopropyl groups, propargyl groups, allyl groups, or a combination thereof.
    • Claim:
      2. The method of claim 1 further including: separating the cyclopropyl substituted diamondoid fuel from the mixture; and cross-linking the allyl substituted diamondoid fuel, thereby forming a polymeric diamondoid fuel.
    • Claim:
      3. The method of claim 1 , further including cross-linking the propargyl substituted diamondoid fuel, thereby forming a polymeric diamondoid fuel.
    • Claim:
      4. The method of claim 1 , wherein the halogenated diamondoid is selected from the group consisting of a bromo-diamondoid, a fluoro-diamondoid, a chloro-diamondoid, an iodo-diamondoid, and combinations thereof; wherein the halogenated diamondoid includes a range of 1 to 4 halogens; and wherein the halogenated diamondoid includes a cage structure including 10 carbons, 14 carbons, 18 carbons, or 22 carbons.
    • Claim:
      5. The method of claim 1 , wherein reacting the halogenated diamondoid with the allyl halogen occurs at a temperature ranging from about −80° C. to about 30° C. for a time ranging from about 15 minutes to about 24 hours.
    • Claim:
      6. The method of claim 1 , the chloroalkane solvent selected from the group consisting of methylene chloride, tetrachloroethane, 1,2-dichloroethane, 1,1-dichloroethane, and combinations thereof.
    • Claim:
      7. The method of claim 1 , wherein the Lewis acid is selected from the group consisting of AlCl 3 , AlBr 3 , BF 3 , FeCl 3 , and combinations thereof.
    • Claim:
      8. The method of claim 1 , wherein the allyl halogen is selected from the group consisting of allyl bromide, allyl idodide, allyl chloride, and combinations thereof.
    • Claim:
      9. The method of claim 1 , wherein the reducing metal is zinc, aluminum, magnesium, lithium, sodium, potassium, calcium, and combinations thereof.
    • Claim:
      10. The method of claim 2 , wherein the cyclopropyl substituted diamondoid fuel is separated by fractional distillation, crystallization, or selective removal of the allyl substituted diamondoid fuel using a reversible binding absorbent.
    • Claim:
      11. The method of claim 1 , further including cross-linking the cyclopropyl substituted diamondoid fuel and the allyl substituted diamondoid fuel using a thiol-ene reaction, or an olefin metathesis reaction to form a polymeric fuel.
    • Claim:
      12. The method of claim 2 , wherein the cross-linking is performed using anionic polymerization, free radical polymerization, Ziegler-Natta polymerization, or thermal polymerization.
    • Claim:
      13. The method of claim 2 , wherein the cross-linking is performed using heat, alkyne cyclotrimerization, alkyne metathesis, or an alkene metathesis.
    • Claim:
      14. The method of claim 1 , wherein the strong base is potassium tert-butoxide, alkali alkoxides, alkaline alkoxides, or combinations thereof.
    • Patent References Cited:
      3437701 April 1969 Capaldi
      3457318 July 1969 Borchert
      5019660 May 1991 Chapman
      7304190 December 2007 Liu
      2004/0077898 April 2004 Yamaguchi






    • Other References:
      Acid Catalyzed Rearrangement of Tetrahydrotricycloopentadiene for Synthesis of High Density Alkyl Diamondoid Fuel Jiawei Xie Xiangwen Zhang Junjian Xie Jisheng Xu Lun Pan Ji Jun Zou Fuel 239 (2019) 652-658 (Year: 2019). cited by examiner
      Electronic and Vibrational Properties of Diamondoid Oligomers J Phys Chem C 2017 121, 27082-27088 C. Tyborski R. Gillen, A Fokin T. Koso N. Fokina, H Hausmann V. Rodionov P. Schreiner C. Thomsen J. Maultzsch (Year: 2017). cited by examiner
      Synthesis of Admanatane J Org Chem 1981 46 5447-5449 (Year: 1981). cited by examiner
      Synthesis of Alpha Silylmethyl Alpha Beta Unsaturated Iminies by Rhodium Catalysed Silylmination of Primary Alkyl Sutstituted Terminal Alkynes Journal Orgnaic Chemistry y Fukumoto h Shimizu A. Tashiro N. Chatani J Org Chem 2014 9 8221-8227 (Year: 2014). cited by examiner
      Yoshiya Fukumoto et al., Synthesis of α-Silylmethyl-α,β-Unsaturated Imines by the Rhodium-Catalyzed Silylimination of Primary-Alkyl-Substituted Terminal Alkynes. cited by applicant
      Tadashi Sasaki et al., Synthesis of Adamantane Derivatives Reaction of 1-Adamantyl Chloride with Trimethylsilyl Pseudohalide, J. Org. Chem., Jun. 4, 1981, 46, 5445-5447, ACS Pub. cited by applicant
      Christoph Tyborski et al., Electronic and Vibrational Properties of Diamondoid Oligomers, J. Phys. Chem. C, 11/72017, 121, 27082-27088. cited by applicant
    • Primary Examiner:
      Weiss, Pamela H
    • Attorney, Agent or Firm:
      Naval Air Warfare Center Weapons Division
      Pangallo, Matthew D.
      Nissim, Stuart H.
    • Accession Number:
      edspgr.11118124