In:
Green Chemistry, Royal Society of Chemistry (RSC), Vol. 24, No. 24 ( 2022), p. 9602-9619
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 C 10 H 16 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 °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.
Type of Medium:
Online Resource
ISSN:
1463-9262
,
1463-9270
Language:
English
Publisher:
Royal Society of Chemistry (RSC)
Publication Date:
2022
detail.hit.zdb_id:
1485110-6
detail.hit.zdb_id:
2006274-6
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