Title: Fast and selective sugar conversion to alkyl lactate and lactic acid with bifunctional carbon-silica catalysts
Authors: de Clippel, Filip *
Dusselier, Michiel *
Van Rompaey, Ruben
Vanelderen, Pieter
Dijkmans, Jan
Makshina, Ekaterina
Giebeler, Lars
Oswald, Steffen
Baron, Gino
Denayer, Joeri
Pescarmona, Paolo
Jacobs, Pierre
Sels, Bert # ×
Issue Date: 2012
Publisher: American Chemical Society
Series Title: Journal of the American Chemical Society vol:134 issue:24 pages:10089-10101
Abstract: A novel catalyst design for the conversion of mono- and disaccharides to lactic acid and its alkyl esters was developed. The design uses a mesoporous silica, here represented by MCM-41, which is filled with a polyaromatic to graphite-like carbon network. The particular structure of the carbon-silica composite allows the accommodation of a broad variety of catalytically active functions, useful to attain cascade reactions, in a readily tunable pore texture. The significance of a joint action of Lewis and weak Brønsted acid sites was studied here to realize fast and selective sugar conversion.
Lewis acidity is provided by grafting the silica component with Sn(IV), while weak Brønsted acidity originates from oxygencontaining functional groups in the carbon part. The weak Brønsted acid content was varied by changing the amount of carbon loading, the pyrolysis temperature, and the post-treatment procedure. As both catalytic functions can be tuned independently, their individual role and optimal balance can be searched for. It was thus demonstrated for the first time that the presence of weak Brønsted acid sites is crucial in accelerating the rate-determining (dehydration) reaction, that is, the first step in the reaction network from triose to lactate. Composite catalysts with well-balanced Lewis/Brønsted acidity are able to convert the trioses, glyceraldehyde and dihydroxyacetone, quantitatively into ethyl lactate in ethanol with an order of magnitude higher reaction rate when compared to the Sn grafted MCM-41 reference catalyst. Interestingly, the ability to tailor the pore architecture further allows the synthesis of a variety of amphiphilic alkyl lactates from trioses and long chain alcohols in moderate to high yields.
Finally, direct lactate formation from hexoses, glucose and fructose, and disaccharides composed thereof, sucrose, was also attempted. For instance, conversion of sucrose with the bifunctional composite catalyst yields 45% methyl lactate in methanol at slightly elevated reaction temperature. The hybrid catalyst proved to be recyclable in various successive runs when used in alcohol solvent.
ISSN: 0002-7863
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Centre for Surface Chemistry and Catalysis
* (joint) first author
× corresponding author
# (joint) last author

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