Hydrodeoxygenation of the Angelica Lactone Dimer, a Cellulose‐Based Feedstock: Simple, High‐Yield Synthesis of Branched C₇–C₁₀ Gasoline‐like Hydrocarbons

Abstract

Dehydration of biomass‐derived levulinic acid under solid acid catalysis and treatment of the resulting angelica lactone with catalytic K2CO3 produces the angelica lactone dimer in excellent yield. This dimer serves as a novel feedstock for hydrodeoxygenation, which proceeds under relatively mild conditions with a combination of oxophilic metal and noble metal catalysts to yield branched C7–C10 hydrocarbons in the gasoline volatility range. Considering that levulinic acid is available in >80 % conversion from raw biomass, a field‐to‐tank yield of drop‐in, cellulosic gasoline of >60 % is possible.

Hydrodeoxygenation processes: Advances on catalytic transformations of biomass-derived platform chemicals into hydrocarbon fuels

“…A stepwise pathway to produce branched C 7 -C 10 gasoline-like hydrocarbons in high yields has also been recently reported by (Mascal et al, 2014). The three-step process proceeds through the formation of an angelica lactone dimer which serves as a novel feedstock for hydrodeoxygenation.…”

Role of Re Species and Acid Cocatalyst on Ir-ReOx/SiO2in the C-O Hydrogenolysis of Biomass-Derived Substrates

“…In addition, Ir-ReO x catalysts were recently applied to the synthesis of branched C7-C10 gasolinelike hydrocarbons from the angelica lactone dimer. [47] The Ir-ReOx catalysts have also been applied to the selective hydrogenation of unsaturated aldehydes to unsaturated alcohols, [48] and the dehydrogenation of vicinal diols to α-hydroxy ketones. [33] The Ir-MoOx catalyst has been used for the aqueous-phase hydrogenation of acetic acid.…”

“…It is expected that the complete C–O bond hydrogenolysis catalyzed by Ir‐ReO x and acid cocatalysts will be applicable to the conversion of cellulose and hemicellulose to n ‐hexane and n ‐pentane, which is regarded as the production of bio‐naphtha. In addition, Ir‐ReO x catalysts were recently applied to the synthesis of branched C 7 –C 10 gasoline‐like hydrocarbons from the angelica lactone dimer …”

Cyclopentanone as an Alternative Linking Reactant for Heterogeneously Catalyzed Furfural Aldol Condensation

“…The enolization of CPO is stabilized by the inductive effect of the side carbon atoms, so the aldol condensation should be enhanced and the retro‐aldolization is minimized. Finally, the total hydrogenation of these products would produce branched derivatives, which increases their quality as gasoline substitutes …”