title: From biomass to chemicals: synthesis of precursors of biodegradable surfactants from 5-hydroxymethylfurfural.
abstract: 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.
authors.affiliation: Instituto de Tecnología Química (UPV-CSIC), Universitat Politècnica de València, Avda dels Tarongers s/n, 46022, Valencia, Spain.
authors.forename: K S
authors.initials: KS
authors.lastname: Arias
authors.forename: Saud I
authors.initials: SI
authors.lastname: Al-Resayes
authors.forename: Maria J
authors.initials: MJ
authors.lastname: Climent
authors.forename: Avelino
authors.initials: A
authors.lastname: Corma
authors.forename: Sara
authors.initials: S
authors.lastname: Iborra
mesh_terms: D020003:1-Octanol / Q000737:chemistry*; D018533:Biomass; D002384:Catalysis; D005662:Furaldehyde / Q000031:analogs & derivatives* / Q000737:chemistry; D012822:Silicon Dioxide / Q000737:chemistry; D012964:Sodium / Q000737:chemistry; D013501:Surface-Active Agents / Q000737:chemistry*; D017641:Zeolites / Q000737:chemistry*
chemical_list: C509968:MCM-41; D013501:Surface-Active Agents; D017641:Zeolites; C008046:5-hydroxymethylfurfural; D012822:Silicon Dioxide; D012964:Sodium; D005662:Furaldehyde; D020003:1-Octanol