Heterocycles p. 1037 - 1044 (2009)
Update date:2022-08-11
Topics:
Luijkx, Gerard C.A.
Huck, Nina P.M.
Van Rantwijk, Fred
Maat, Leendert
Van Bekkum, Herman
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 Bronsted 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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Doi:10.1021/acs.inorgchem.0c01891
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