A combined photobiological–photochemical route to C₁₀ cycloalkane jet fuels from carbon dioxide via isoprene

Abstract

The hemiterpene isoprene is a volatile C5 hydrocarbon with industrial applications. It is generated today from fossil resources, but can also be made in biological processes. We have utilized engineered...

Light-driven (cross-)dimerization of terpenes as a route to renewable C15–C30crudes for fuel and lubricant oil applications

“…On the basis of our previous study, 35 1,1-dinapthylmethanone 8 was used as photosensitizer. Additionally, screening with three other aromatic ketone derivatives (benzophenone, xanthone and thioxanthone) was performed for dimerization of myrcene in search of a better photosensitizer.…”

“…The photosensitizer 8 exhibits a broad absorption band within the range of 300–400 nm (Fig. S2B†), 35,41 which might enable the dimerization to be carried out under simulated and natural sunlight. Therefore, mixtures of myrcene and α-phellandrene with 8 were irradiated under simulated sunlight with an intensity of 1 sun equivalent (AM 1.5 G) and using a flat coiled FEP tubing (CMS IV, Fig.…”

“…The photosensitizer 8 was prepared as previously described. 35 The synthesis of myrcene epoxide was performed by following the method reported by Hioki et al 43…”

“…33 Since cycloalkanes are reported as high energy density combustion fuels, 34 our group has recently reported on a fruitful route to solar jet fuels, where the photobiologically produced isoprene is subject to photosensitized dimerization. 35 Herein, we apply the photochemical dimerization approach to mono- and sesquiterpenes bearing conjugated diene units, i.e. α-phellandrene 1 , myrcene 2 and ocimene 3 .…”

Designer Biosynthetic Jet Fuels Derived from Isoprene and α-Olefins

“…This five-carbon conjugated hydrocarbon can be directly produced through fermentation 20 or derived from other biobased molecules including isoprenol, 21−24 mesaconic/itaconic acid, 25,26 and mevalanolactone. 27,28 Isoprene can be readily converted to jet fuel blendstocks through catalytic 29−33 and photochemical 34 cycloadditions as well as oligomerization reactions. 35−37 Cycloalkanes prepared through these routes exhibit high densities and heats of combustion, while maintaining low viscosities.…”