A Proposal to Synthesize Modified Churchanes for Mixtures with JP-10 to Enhance Energy Density

Propulsion Research, LLC, in collaboration with Florida State University (FSU), the U.S. Air Force Academy (USAFA), and the National Renewable Energy Laboratory (NREL), proposes the scalable production of biorenewable cyclopentadiene (CPD) and the development of a pilot-scale Diels-Alder reactor for the synthesis of high-energy density (HED) fuels. The project focuses on producing advanced strained hydrocarbons—churchanes and 1,3-bishomocubane—that enhance energy density and solubility in JP-10-based mixtures. HED fuels such as JP-10 and RJ-5 rely on CPD or its dimer, dicyclopentadiene, for synthesis. Our approach leverages CPD as a conjugated diene in a Diels-Alder reaction with dienophiles such as p-benzoquinone. The resulting intermediates undergo a photochemical reaction to yield novel strained hydrocarbons. A flow photochemistry process developed at FSU will be instrumental in scaling up these reactions, ensuring high throughput and energy efficiency. Key technical innovations include: Scalable CPD Production: Building on established renewable CPD synthesis methods, we aim to transition from lab-scale to pilot-scale production, Diels-Alder Reactor Development: Implementing an optimized reactor to enable efficient synthesis of churchanes and 1,3-bishomocubane, Photochemical Flow Processing: Using FSU’s advanced reactor to improve yield and throughput of churchandione derivatives, and Fuel Compatibility Optimization: Enhancing solubility and performance through structural modifications, including Corey-Chaykovsky epoxidation and selective functionalization This effort will establish a scalable, renewable pathway for HED fuel production, reducing reliance on petrochemical sources. The proposed molecules exhibit high strain energy (?80 kcal/mol for 1,3-bishomocubane), making them attractive alternatives to JP-10 and RJ-5. Moreover, the streamlined synthesis minimizes energy-intensive distillation steps, improving overall efficiency. Phase I goals are: demonstrate scalable CPD production, construct and validate the pilot-scale Diels-Alder reactor, optimize photochemical processing for high-yield churchane synthesis, and evaluate solubility and energetic properties for fuel applications. By leveraging cutting-edge flow chemistry and renewable feedstocks, this project will advance HED fuel technology to meet the Navy’s operational energy needs.