Synthesis of aviation fuel from bio-derived isophorone

Abstract

Using photochemical [2 + 2] cycloaddition, a cyclobutane dione was generated from isophorone, a condensate of bio-acetone.

Bio‐Based Cycloalkanes: The Missing Link to High‐Performance Sustainable Jet Fuels

“…The higher densities of the isophorone‐based fuels result in volumetric NHOCs ranging from 35.0‐38.8 MJ L ‐1 . These values are 5‐17% higher than the minimum value for Jet‐A [289] . However, none of these fuels meet the Jet‐A viscosity requirement (<8.0 mm 2 s −1 at −20 °C) and would require blending with conventional fuels.…”

“…[17,288] Compared to cyclopentane with a strain energy of 5.4 kJ mol À 1 , cyclobutane offers 27.2 kJ mol À 1 of ring strain energy, while not suffering from the relatively low thermal stability of cyclopropane rings. [17] Ryan et al [289] generated a cyclobutane containing fuel blend via [2 + 2]-cycloaddition [290][291][292][293][294] of isophorone. Previous work on photochemical [2 + 2]-cycloaddition of isophorone with bio-derived olefins [295] demonstrated the benefit of isophorone's enone functionality, which allows it to absorb long wavelengths (> 310 nm), circumventing the need for a photosensitizer.…”

“…These values are 5-17% higher than the minimum value for Jet-A . [289] However, none of these fuels meet the Jet-A viscosity requirement (< 8.0 mm 2 s À 1 at À 20°C) and would require blending with conventional fuels.…”

“…Compared to cyclopentane with a strain energy of 5.4 kJ mol −1 , cyclobutane offers 27.2 kJ mol −1 of ring strain energy, while not suffering from the relatively low thermal stability of cyclopropane rings [17] . Ryan et al [289] . generated a cyclobutane containing fuel blend via [2+2]‐cycloaddition [290–294] of isophorone.…”

Metabolically engineered Caldicellulosiruptor bescii as a platform for producing acetone and hydrogen from lignocellulose

“…For example, ethanol can be utilized as a fuel, but also as a source of ethylene via catalytic dehydration (Morschbacker, 2009). Acetone provides yet another platform compound, with many industrial uses as well as catalytic routes to fuels such as isopropanol (Rahman & Salem, 2014) and jet fuel (Ryan et al, 2020).…”