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Heterogeneous Ketone Hydrodeoxygenation for the Production of Fuels and Feedstocks from Biomass
Author(s) -
Jenkins Rhodri W.,
Moore Cameron M.,
Semelsberger Troy A.,
Sutton Andrew D.
Publication year - 2017
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201601678
Subject(s) - hydrodeoxygenation , chemistry , catalysis , tetrahydrofuran , organic chemistry , molecule , biomass (ecology) , selectivity , oceanography , solvent , geology
In this work, we describe a simple, heterogeneous catalytic system for the hydrodeoxygenation (HDO) of 5‐nonanone and 2,5‐hexanedione, which we use as model compounds for more complex biomass‐derived molecules. We present the stepwise reduction of ketones by using supported metal and solid acid catalysts to identify the intermediates en route to hydrocarbons. Although monoketone HDO can be achieved rapidly using moderate conditions (Ni/SiO 2 .Al 2 O 3 , HZSM‐5, 200 °C, 1.38 MPa H 2 , 1 h), quantitative γ‐polyketone HDO requires higher pressures and longer reaction times (Pd/Al 2 O 3 , HZSM‐5, 2.76 MPa H 2 , 5 h), although these are more facile conditions than have been reported previously for γ‐polyketone HDO. Stepwise HDO of the γ‐polyketone shows the reaction pathway occurs through ring‐closure to a saturated tetrahydrofuran species intermediate, which requires increased H 2 pressure to ring‐open and subsequently to fully HDO. This work allows for further understanding of bio‐derived molecule defunctionalization mechanisms, and ultimately aids in the promotion of biomass as a feedstock for fuels and chemicals.