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Photoinduced cycloaddition of biomass derivatives to obtain high-performance spiro-fuel

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Abstract

The photoinduced conversion of biomass-derived chemicals to high value chemicals and advanced fuels is of great significance but still challenging. Herein, a green and efficient self-sensitized [2 + 2] cycloaddition process is developed to convert biomass-derived β-pinene and isophorone to spirocyclic molecules, which cannot be achieved by thermal catalytic conversion. The photoreaction can take place with isophorone as the self-sensitizer, with high selectivity and a yield of up to 91.1%. A triplet sensitization mechanism is disclosed by a combination of triplet quenching, phosphorescence quenching, Stern–Volmer kinetic analysis, DFT calculations and photochemical kinetic studies. When combined with hydrodeoxygenation, spiro-fuel is obtained with an overall yield of 85.0% showing a high density of 0.911 g mL−1 which is 16.8% higher than that of conventional aviation kerosene (ca. 0.78 g mL−1), along with excellent cryogenic properties. Notably the self-sensitized cycloaddition strategy can be extended to a wide range of biomass derived α,β-unsaturated ketones and alkenes. Thus, this work provides a promising ring-increasing route to upgrade low-density bio-derived feedstocks to high-density hydrocarbons.

Graphical abstract: Photoinduced cycloaddition of biomass derivatives to obtain high-performance spiro-fuel

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Publication details

The article was received on 08 Aug 2019, accepted on 12 Sep 2019 and first published on 13 Sep 2019


Article type: Paper
DOI: 10.1039/C9GC02790D
Green Chem., 2019, Advance Article

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    Photoinduced cycloaddition of biomass derivatives to obtain high-performance spiro-fuel

    J. Xie, L. Pan, G. Nie, J. Xie, Y. Liu, C. Ma, X. Zhang and J. Zou, Green Chem., 2019, Advance Article , DOI: 10.1039/C9GC02790D

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