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ChemSusChem. 2017 Feb 22;10(4):711-719. doi: 10.1002/cssc.201601727. Epub 2017 Feb 7.

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

Li S1,2, Chen F1,2, Li N1,3, Wang W1, Sheng X1,2, Wang A1,3, Cong Y1, Wang X1, Zhang T1,3.

Author information

1
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, P. R. China.
2
University of Chinese Academy of Sciences, Beijing, 10049, P. R. China.
3
iChEM, Collaborative Innovation Centre of Chemistry for Energy Materials, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, P. R. China.

Abstract

A series of renewable C9 -C12 triketones with repeating [COCH2 CH2 ] 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/TiO2 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 ).

KEYWORDS:

aqueous-phase hydrogenation; diketones; jet fuel; lignocellulose; triketones

PMID:
28052535
DOI:
10.1002/cssc.201601727
[Indexed for MEDLINE]

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