New route for synthesis of jet-range cycloalkanes and aromatics from lignocellulose-derived platforms
Researchers in China report the synthesis of jet-fuel range C10 and C15 polycyclic alkanes and aromatics with furfuryl alcohol and isoprene, two platform compounds which can be derived from lignocellulose. An open-access paper on their work appears in the RSC journal Green Chemistry.
Cycloalkanes (especially polycycloalkanes) and aromatics—with their higher density and volumetric heat values—are two main components of aviation fuels. The aromatic hydrocarbons in fuel also ensure the shrinkage of aged elastomer seals and prevent fuel leakage.
In this work, two three-step routes were developed for the synthesis of renewable polycyclic alkanes and aromatics, respectively. First, 4-hydroxycyclopent-2-enone (HCP) was synthesized by 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. Finally, a mixture of methyl octahydroindene and dimethyl dodecahydrofluorene were produced by the hydrodeoxygenation of the C10 and C15 oxygenates under the co-catalysis of Ru/C and acidic zeolites.
As another option, the C10 and C15 oxygenates can also be converted to a mixture of alkylated indans and fluorenes by the transfer hydrodeoxygenation over the Mo modified Pd/SiO2 catalyst without using any external hydrogen source.—Xu et al.
Strategy for the synthesis of C10 and C15 polycyclic alkane and aromatics with furfuryl alcohol and isoprene from lignocellulose. Xu et al.
Jingyuan Xu, Guangyi Li, Ai-Qin Wang, Cong Yu, Xiaodong Wang and Ning Li (2022) “Synthesis jet fuel range polycyclic alkanes and aromatics from furfuryl alcohol and isoprene” Green Chemistry doi: 10.1039/D2GC00189F