Premium
From Biomass to Chemicals: Synthesis of Precursors of Biodegradable Surfactants from 5‐Hydroxymethylfurfural
Author(s) -
Arias K. S.,
AlResayes Saud I.,
Climent Maria J.,
Corma Avelino,
Iborra Sara
Publication year - 2013
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201200513
Subject(s) - chemistry , acetal , yield (engineering) , catalysis , 5 hydroxymethylfurfural , selectivity , organic chemistry , zeolite , pulmonary surfactant , alkyl , heterogeneous catalysis , biomass (ecology) , materials science , biochemistry , oceanography , metallurgy , geology
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.