title: Synthesis of Renewable Triketones, Diketones, and Jet-Fuel Range Cycloalkanes with 5-Hydroxymethylfurfural and Ketones.
abstract: A series of renewable C9-C12triketones with repeating [COCH2CH2] 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/TiO2catalyst. 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).
authors.affiliation: State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, P. R. China.|University of Chinese Academy of Sciences, Beijing, 10049, P. R. China.
authors.forename: Shanshan
authors.initials: S
authors.lastname: Li
authors.affiliation: State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, P. R. China.|University of Chinese Academy of Sciences, Beijing, 10049, P. R. China.
authors.forename: Fang
authors.initials: F
authors.lastname: Chen
authors.affiliation: State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, P. R. China.|iChEM, Collaborative Innovation Centre of Chemistry for Energy Materials, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, P. R. China.
authors.forename: Ning
authors.initials: N
authors.lastname: Li
authors.affiliation: State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, P. R. China.
authors.forename: Wentao
authors.initials: W
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, P. R. China.|University of Chinese Academy of Sciences, Beijing, 10049, P. R. China.
authors.forename: Xueru
authors.initials: X
authors.lastname: Sheng
authors.affiliation: State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, P. R. China.|iChEM, Collaborative Innovation Centre of Chemistry for Energy Materials, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, P. R. China.
authors.forename: Aiqin
authors.initials: A
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, P. R. China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Cong
authors.affiliation: State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, P. R. China.
authors.forename: Xiaodong
authors.initials: X
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, P. R. China.|iChEM, Collaborative Innovation Centre of Chemistry for Energy Materials, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, P. R. China.
authors.forename: Tao
authors.initials: T
authors.lastname: Zhang
mesh_terms: D002384:Catalysis; D003516:Cycloparaffins / Q000138:chemical synthesis*; D005662:Furaldehyde / Q000031:analogs & derivatives* / Q000737:chemistry; D055772:Green Chemistry Technology / Q000379:methods*; D006838:Hydrocarbons / Q000737:chemistry; D006865:Hydrogenation; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D003516:Cycloparaffins; D006838:Hydrocarbons; D007659:Ketones; C008046:5-hydroxymethylfurfural; C029662:JP5 jet fuel; D005662:Furaldehyde
keywords: aqueous-phase hydrogenation; diketones; jet fuel; lignocellulose; triketones