Synthesis of biomass-derived methylcyclopentane as a gasoline additive via aldol condensation/hydrodeoxygenation of 2,5-hexanedione

Sacia, Eric R.; Deaner, Matthew H.; Louie, Ying “Lin”; Bell, Alexis T.

doi:10.1039/c4gc02292k

Synthesis of biomass-derived methylcyclopentane as a gasoline additive via aldol condensation/hydrodeoxygenation of 2,5-hexanedione

Journal Article · Thu Jan 22 23:00:00 EST 2015 · Green Chemistry

DOI:https://doi.org/10.1039/c4gc02292k· OSTI ID:1571040

Sacia, Eric R. ^[1]; Deaner, Matthew H. ^[1]; Louie, Ying “Lin” ^[1]; Bell, Alexis T. ^[1]

Univ. of California, Berkeley, CA (United States)

A novel approach to produce biomass-derived gasoline is the hydrolysis of 2,5-dimethylfuran (DMF) to produce 2,5-hexanedione followed by base-catalyzed intramolecular aldol condensation of this product to form 3-methylcyclopent-2-enone (MCP). By proper choice of catalysts and conditions, MCP yields of 98% can be achieved. Here, we further show that hydrogenation of MCP over Pt/NbOPO₄ gives methylcyclopentane with virtually quantitative yields. Methylcyclopentane is an attractive gasoline substitute for ethanol, since its octane number is similar to ethanol and its gravimetric energy density is 58% higher.

View Accepted Manuscript (DOE)

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1571040

Journal Information:: Green Chemistry, Journal Name: Green Chemistry Journal Issue: 4 Vol. 17; ISSN GRCHFJ; ISSN 1463-9262

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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