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Photoinduced cycloaddition of biomass derivatives to obtain high-performance spiro-fuel.
- Source :
- Green Chemistry; 11/7/2019, Vol. 21 Issue 21, p5886-5895, 10p
- Publication Year :
- 2019
-
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<superscript>−1</superscript> which is 16.8% higher than that of conventional aviation kerosene (ca. 0.78 g mL<superscript>−1</superscript>), 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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 14639262
- Volume :
- 21
- Issue :
- 21
- Database :
- Complementary Index
- Journal :
- Green Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 139350514
- Full Text :
- https://doi.org/10.1039/c9gc02790d