Acid-catalyzed rearrangement of biomass polycyclic sesquiterpene derivatives to high-performance alkyl-adamantanes

•Acid-catalyzed rearrangement to synthesize high-performance biomass-based alkyl-adamantanes is reported.•The rearrangement products have high density, low viscosity and high thermal oxidative stability.•The rearrangement products can improve the combustion performance of JP-10. Biomass-based aviation fuel is attractive for sustainable development. Herein, we report a facile route to synthesize alkyl-adamantanes (AAMs) via acid-catalyzed rearrangement of biomass polycyclic sesquiterpene derivatives (bio-PCS derivatives). The reaction conditions including catalysts, solvents, reaction temperature and reaction time were optimized. Notably, a total AAMs yield of 65.1% was achieved under the optimal conditions. The kinetics of rearrangement reaction was investigated, and the reaction rate constant (k) and apparent activation energy (Ea) were calculated based on the experimental kinetic data. The rearrangement products possess high density of 0.90 g/cm3, high net heat of combustion of 42.6 MJ/kg, low viscosity (22.5 mm2/s at −20℃) and high thermal oxidative stability. The blending of rearrangement products with JP-10 can significantly shorten the ignition delay time (IDT) of JP-10. This work provides a method to synthesize high-performance biomass-based AAMs.