From biomass to chemicals: synthesis of precursors of biodegradable surfactants from 5-hydroxymethylfurfural.

K S Arias, Saud I Al-Resayes, Maria J Climent, Avelino Corma, Sara Iborra

Instituto de Tecnología Química (UPV-CSIC), Universitat Politècnica de València, Avda dels Tarongers s/n, 46022, Valencia, Spain.

ChemSusChem 2013 Jan

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The selective acetalization of 5-hydroxymethylfurfural (HMF) with long-chain alkyl alcohols has been performed to obtain precursors of molecules with surfactant properties. If direct acetalization of HMF with n-octanol is performed in the presence of strong acids (homogeneous and heterogeneous catalysts), an increase in etherification versus acetalization occurs. Beta zeolite catalyzes both reactions. However, if the acidity of a zeolite (Beta) was controlled by partial exchange of H(+) with Na(+), the dioctyl acetal of HMF can be achieved in 95% yield by transacetalization. It is possible to achieve a high yield in a very short reaction time through a two-step one-pot process, which includes the synthesis of the dimethyl acetal of HMF followed by transacetalization with n-octanol. The one-pot process could be extended to other alcohols that contain 6-12 carbon atoms to afford 87-98% yield of the corresponding dialkyl acetal with a selectivity higher than 96%. The optimized catalyst with an adequate Na content (1.5NaBeta) could be recycled without loss of activity or selectivity. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

K S Arias, Saud I Al-Resayes, Maria J Climent, Avelino Corma, Sara Iborra. From biomass to chemicals: synthesis of precursors of biodegradable surfactants from 5-hydroxymethylfurfural. ChemSusChem. 2013 Jan;6(1):123-31