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UC Davis team optimizes levulinic ester self-condensation process for production of cellulosic gasoline

A team at UC Davis has optimized the levulinic ester self-condensation reaction and the efficient conversion of its products—which are highly branched cyclopentadienes—into a mixture of substituted cyclopentanes with high octane ratings and excellent density and flow properties.

In a paper in the RSC journal Green Chemistry, they reported that the optimized process delivered C8–C10 plus C12 and C13 products in high yield with very good fuel properties which, being only four efficient steps removed from raw biomass, may provide a competitive basis for cellulosic gasoline production.

The production of bio-based fuels by the condensation of biogenic aldehydes or ketones with carbohydrate-derived platform molecules, often furfurals, followed by hydrodeoxygenation generally leads to C9+ products. The application of this approach has given rise to dozens of papers describing routes to diesel-type fuels, which consist mainly of linear alkanes in the C10–C20 range.

The paraffinic fraction of motor gasoline, on the other hand, is comprised of hydrocarbons up to about C12, a key characteristic of which is the extent of branching in the carbon chains. In general, the more highly branched the molecule, the higher the performance of the fuel, as measured by the antiknock index, expressed in terms of research octane number or “RON”.

… To date, few reports of cellulosic biomass-derived alkanes sufficiently branched to serve as biogasoline or even mid-performance gasoline blendstocks have surfaced. Those that do emerge generally involve the cracking, pyrolysis, or gasification of biomass or its derivatives in combination with catalytic upgrading or reforming methods commonly employed in the petroleum industry, i.e. essentially using biomass as a feed for refinery practices.

—Li et al.

In earlier work, the researchers had shown that it is possible to produce branched C7-C10 hydrocarbons in processes using levulinic acid derived from cellulosic biomass. The new work describes the optimization of one of the levulinic-acid-based pathways to yield C8–C13 branched hydrocarbons characteristic of motor gasoline.

Resources

  • Zheng Li, Andrew L. Otsukia and Mark Mascal (2018) “Production of cellulosic gasoline via levulinic ester self-condensation” Green Chemistry doi: 10.1039/C8GC01432A

Comments

Engineer-Poet

Hydrodeoxygenation means supplying external hydrogen.  While this process appears clever (I don't know enough chemistry to tell), I have to wonder how much of the energy of the final product comes from hydrogen?  A majority, I suspect based on my own calculations.  How would this hydrogen be sourced?  That's going to matter a great deal.

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