Synthesis of Renewable Triketones, Diketones, and Jet-Fuel Range Cycloalkanes with 5-Hydroxymethylfurfural and Ketones

Graphical Green triketones : Renewable C 9 –C 12 triketones with repeating [COCH 2 CH 2 ] units are synthesized in high carbon yields (ca. 90 %) over a cost-effective and reusable Au/TiO 2 catalyst. The triketones as obtained can be used as feedstocks in the production of conducting or semi-conducting polymers. Furthermore, they can also be converted to diketones or jet-fuel range branched cycloalkanes with high densities and low freezing points. A series of renewable C 9 –C 12 triketones with repeating [COCH 2 CH 2 ] units were synthesized in high carbon yields (ca. 90 %) by the aqueous-phase hydrogenation of the aldol-condensation products of 5-hydroxylmethylfurfural (HMF) and ketones over an Au/TiO 2 catalyst. Compared with the reported routes, this new route has many advantages such as being environmentally friendly, having fewer steps, using a cheaper and reusable catalyst, etc. The triketones as obtained can be used as feedstocks in the production of conducting or semi-conducting polymers. Through a solvent-free intramolecular aldol condensation over solid-base catalysts, the triketones were selectively converted to diketones, which can be used as intermediates in the synthesis of useful chemicals or polymers. As another application, the tri- and diketones can also be utilized as precursors for the synthesis of jet-fuel range branched cycloalkanes with low freezing points (224–248 K) and high densities (ca. 0.81 g mL −1 ).