title: Highly selective condensation of biomass-derived methyl ketones as a source of aviation fuel.
abstract: Aviation fuel (i.e., jet fuel) requires a mixture of C9 -C16 hydrocarbons having both a high energy density and a low freezing point. While jet fuel is currently produced from petroleum, increasing concern with the release of CO2 into the atmosphere from the combustion of petroleum-based fuels has led to policy changes mandating the inclusion of biomass-based fuels into the fuel pool. Here we report a novel way to produce a mixture of branched cyclohexane derivatives in very high yield (>94 %) that match or exceed many required properties of jet fuel. As starting materials, we use a mixture of n-alkyl methyl ketones and their derivatives obtained from biomass. These synthons are condensed into trimers via base-catalyzed aldol condensation and Michael addition. Hydrodeoxygenation of these products yields mixtures of C12 -C21 branched, cyclic alkanes. Using models for predicting the carbon number distribution obtained from a mixture of n-alkyl methyl ketones and for predicting the boiling point distribution of the final mixture of cyclic alkanes, we show that it is possible to define the mixture of synthons that will closely reproduce the distillation curve of traditional jet fuel.
authors.affiliation: Department of Chemical and Biomolecular Engineering, University of California, Berkeley, 107 Gilman Hall, Berkeley, CA 94720 (USA).
authors.forename: Eric R
authors.initials: ER
authors.lastname: Sacia
authors.affiliation: Department of Chemical and Biomolecular Engineering, University of California, Berkeley, 107 Gilman Hall, Berkeley, CA 94720 (USA).
authors.forename: Madhesan
authors.initials: M
authors.lastname: Balakrishnan
authors.affiliation: Department of Chemical and Biomolecular Engineering, University of California, Berkeley, 107 Gilman Hall, Berkeley, CA 94720 (USA).
authors.forename: Matthew H
authors.initials: MH
authors.lastname: Deaner
authors.affiliation: Department of Chemical and Biomolecular Engineering, University of California, Berkeley, 107 Gilman Hall, Berkeley, CA 94720 (USA).|Department of Chemistry, University of California, Berkeley, 107 Gilman Hall, Berkeley, CA 94720 (USA).
authors.forename: Konstantinos A
authors.initials: KA
authors.lastname: Goulas
authors.affiliation: Department of Chemistry, University of California, Berkeley, 107 Gilman Hall, Berkeley, CA 94720 (USA).
authors.forename: F Dean
authors.initials: FD
authors.lastname: Toste
authors.affiliation: Department of Chemical and Biomolecular Engineering, University of California, Berkeley, 107 Gilman Hall, Berkeley, CA 94720 (USA). bell@cchem.berkeley.edu.
authors.forename: Alexis T
authors.initials: AT
authors.lastname: Bell
mesh_terms: D000473:Alkanes / Q000737:chemistry; D000536:Aluminum Hydroxide / Q000737:chemistry; D018533:Biomass; D002384:Catalysis; D004736:Energy-Generating Resources; D007659:Ketones / Q000737:chemistry*; D008276:Magnesium Hydroxide / Q000737:chemistry
chemical_list: D000473:Alkanes; D007659:Ketones; C010467:hydrotalcite; D000536:Aluminum Hydroxide; D008276:Magnesium Hydroxide
keywords: CC coupling reactions; biofuels; heterogeneous catalysis; hydrogenation; jet fuel