467 / 2018-09-06 08:38:43

Synthesis of jet fuel range high density polycycloalkanes with lignocellulosic platform compounds

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With the increase of social concern to the energy and environmental problems, the synthesis of renewable jet fuel with lignocellulose has drawn a lot of attention. During the past years, great efforts have been devoted to the production of jet fuel range hydrocarbons with the lignocellulosic platform compounds. However, most of the reported work about the lignocellulosic bio-jet fuel is concentrated on the production of C8-C16 chain alkanes. Compared with conventional jet fuels (the mixtures of chain alkanes and cyclic hydrocarbons), these alkanes have lower densities (or volumetric heat values). In real application, they must be blended with conventional jet fuel to meet the specification of aviation fuels. As a solution this problem, it is still necessary to development some new routes for the synthesis of jet fuel range cyclic hydrocarbons (especially polycycloalkanes) with lignocellulosic platform compounds.
Synthesis of jet fuel range cycloalkanes with cyclopentanone. Cyclopentanone is the aqueous phase selective hydrogenation product of furfural which has been produced in industrial scale by the hydrolysis/dehydration of hemicellulose. In this work, bi(cyclopentane) and tri(cyclopentane) were selectively synthesized by the self adol condensation or the aldol condensation/hydrogenation of cyclopentanone followed by HDO under solvent-free conditions.
Synthesis of jet fuel range cycloalkanes with cyclopentanol. Cyclopentanol is the by-product in the manufacture of cyclopentanone by the aqueous phase selective hydrogenation of furfural. In some recent reports, cyclopentanol was selectively produced by the aqueous phase hydrogenation of furfural. In this work, we developed three routes for the synthesis of jet fuel range polycycloalkanes with cyclopentanol. Firstly, a mixture of C10 and C15 oxygenates was synthesized by the Guerbet reaction of cyclopentanol under the co-catalysis of Raney metal and solid base. After the HDO of these oxygenates, a mixture of bi(cyclopentane) and tri(cyclopentane) was produced. Secondly, we also developed a new route for the synthesis of decalin by the dimerization/rearrangement of cyclopentene (from the dehydration of cyclopentanol) followed by hydrogenation. As another option, we also prepared the decalin by the self-aldol condensation of cyclopentanone, followed by hydrogenation, dehydration/isomerization and hydrogenation.
In summary, a series of jet fuel range polycycloalkanes (such as di(cyclopentane), di(cyclopentane) and decalin) were synthesis with cyclopentanone and cyclopentanol from the aqueous phase selective hydrogenation of furfural. These polycycloalkanes have high densities. As a potential application, they can be used as fuel additives to improve the volumetric heat values of conventional bio-jet fuels.