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A Combined Photobiological-Photochemical Route to C10 Cycloalkane Jet Fuels from Carbon Dioxide via Isoprene
preprintsubmitted on 18.02.2021, 18:35 and posted on 19.02.2021, 12:59 by Anup Rana, Leandro Cid Gomes, João Rodrigues, Hugo Arrou-Vignod, Johan Sjölander, Nathalie Proos Vedin, Ouissam El Bakouri, Karin Stensjö, Peter Lindblad, Leena Andersson, Mathias Berglund, Pia Lindberg, Henrik Ottosson
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 photosynthetic cyanobacteria for direct, light-driven production of bio-isoprene from carbon dioxide, and show that isoprene in a subsequent photochemical step, using simulated or natural solar light, can be dimerized into limonene, paradiprene, and isomeric C10H16 hydrocarbons (monoterpenes) in very high yields (above 90% after 44 hours) under sensitized conditions. The optimal sensitizer in our experiments is di(naphth-1-yl)methanone which we can use with a loading of merely 0.1 mol%, and it is easily 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 jet fuel drop-in. Importantly, the photodimerization can be carried out at ambient conditions. The high content of hydrogenated [2+2] dimers in our isoprene dimer mix lowers the flash point below the threshold (38 °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.