Synthesis of jet fuel range polycyclic alkanes and aromatics from furfuryl alcohol and isoprene

Abstract

Jet fuel range C₁₀ and C₁₅ polycyclic alkanes and aromatics were first synthesized with furfuryl alcohol and isoprene, two platform compounds which can be derived from lignocellulose. First, 4-hydroxycyclopent-2-enone (HCP) was selectively obtained from the aqueous phase rearrangement of furfuryl alcohol. Subsequently, C₁₀ and C₁₅ oxygenates with polycyclic carbon chain structures were obtained by the Diels–Alder (D–A) reaction of HCP and isoprene in the absence of any catalyst. After being hydrodeoxygenated under the co-catalysis of Ru/C + H-β, the C₁₀ and C₁₅ oxygenates were further converted into a mixture of methyl octahydroindene and dimethyl dodecahydrofluorene with high density (0.908 g mL⁻¹). As another option, the C₁₀ and C₁₅ oxygenates can also be converted into a mixture of indanes and fluorenes by the hydrogen transfer hydrodeoxygenation over a Mo modified Pd/SiO₂ catalyst without using any external hydrogen source.