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Research article2022Peer reviewedOpen access

A combined photobiological-photochemical route to C-10 cycloalkane jet fuels from carbon dioxide via isoprene

Rana, Anup; Gomes, Leandro Cid; Rodrigues, Joao S.; Yacout, Dalia M. M.; Arrou-Vignod, Hugo; Sjolander, Johan; Vedin, Nathalie Proos; El Bakouri, Ouissam; Stensjo, Karin; Lindblad, Peter; Andersson, Leena; Sundberg, Cecilia; Berglund, Mathias; Lindberg, Pia; Ottosson, Henrik

Abstract

The hemiterpene isoprene is a volatile C-5 hydrocarbon with industrial applications. It is generated today from fossil resources, but can also be made in biological processes. We have utilized engineered photosynthetic cyanobacteria for direct, light-driven production of bio-isoprene from carbon dioxide, and show that isoprene in a subsequent photochemical step, using either near-UV or simulated or natural solar light, can be dimerized into limonene, paradiprene, and isomeric C10H16 hydrocarbons (monoterpenes) in high yields under photosensitized conditions (above 90% after 44 hours with near-UV and 61% with simulated solar light). The optimal sensitizer in our experiments is di(naphth-1-yl)methanone which we use with a loading of 0.1 mol%. It can also easily be recycled for subsequent photodimerization cycles. The isoprene dimers generated are a mixture of [2 + 2], [4 + 2] and [4 + 4] cycloadducts, and after hydrogenation this mixture is nearly ideal as a drop-in jet fuel. Importantly the photodimerization can be carried out at ambient conditions. However, the high content of hydrogenated [2 + 2] dimers in our isoprene dimer mix lowers the flash point below the threshold (38 degrees C); yet, these dimers can be converted thermally into [4 + 2] and [4 + 4] dimers. When hydrogenated these monoterpenoids fully satisfy the criteria for drop-in jet fuels with regard to energy density, flashpoint, kinematic viscosity, density, and freezing point. Life-cycle assessment results show a potential to produce the fuel in an environmentally sustainable way.

Published in

Green Chemistry
2022, Volume: 24, number: 24, pages: 9602-9619
Publisher: ROYAL SOC CHEMISTRY