Diels–Alder Cycloaddition of Cyclopentadiene with α‑Olefins for the Synthesis of High-Performance Sustainable Aviation Fuels

• Published in: Energy & fuels 2024-10, Vol.38 (19), p.18763-18768
• Main Authors: Woodroffe, Josanne-Dee, Zhang, Derek D., Harvey, Benjamin G.
• Format: Article
• Language: English
• Subjects: Bioenergy, Biofuels, and Biorefinery
• ISSN: 0887-0624; 1520-5029
• DOI: 10.1021/acs.energyfuels.4c03203

A series of alkyl-substituted bicycloheptanes were synthesized by Diels–Alder cycloaddition of cyclopentadiene and C5–C8 α-olefins. The reactions were conducted with three equivalents of the α-olefin to ensure a high conversion to the cross-coupled product and did not require the use of a solvent or catalyst. The resulting products were then hydrogenated over 10% Pd/C and distilled to yield jet fuel blendstocks. The saturated hydrocarbons exhibited densities ranging from 0.861 to 0.872 g mL–1 (11.1–12.5% higher than the lower limit for Jet-A), gravimetric net heats of combustion ranging from 42.8 to 43.3 MJ kg–1 (comparable to Jet-A), and −20 °C kinematic viscosities ranging from 5.49 to 18.00 mm2 s–1. Cyclopentadiene can be readily derived from crude biomass sources including hemicellulose, while C5–C8 olefins can be produced from biomass through Fischer–Tropsch catalysis or oligomerization of bio-based ethylene. Thus, this work provides a route to generate molecularly designed biosynthetic fuels with potential applications as blending agents to increase the performance of sustainable aviation fuels.