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Paper | Special issue | Vol 77, No. 2, 2009, pp.1037-1044
Published online: 29th September, 2008
DOI: 10.3987/COM-08-S(F)81
Ether Formation in the Hydrogenolysis of Hydroxymethylfurfural over Palladium Catalysts in Alcoholic Solution

Gerard C. A. Luijkx, Nina P. M. Huck, Gred van Rantwijk, Leendert Maat,* and Herman van Bekkum*

*Faculty of Chemical Engineering, Delft University of Technology, Julianalaan 136, 2628 BL Delft, The Netherlands

Abstract

5-Hydroxymethylfurfural, a product from renewable feedstock, was subjected to hydrogenolysis over palladium catalysts in 1-propanol aiming at the synthesis of 2,5-dimethylfuran, a potential transportation fuel enhancer. Intermediates are 5-hydroxymethyl-2-(propyloxymethyl)furan, formed with high selectivity, and 5-methyl-2-(propyloxymethyl)furan. Acetals are assumed to be initially formed. Acetalisation and hydrogenolysis are catalysed by traces of a Brønsted acid. Important variables are the palladium support and the solvent. In 2-propanol also ether formation takes place. In 1,4-dioxane mainly 2,5-bis(hydroxymethyl)furan is formed, in water ring opening becomes a major reaction. The formation of some side-products is discussed.

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