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Biomass‐Derived Chemicals: Synthesis of Biodegradable Surfactant Ether Molecules from Hydroxymethylfurfural
Author(s) -
Arias Karen S.,
Climent Maria J.,
Corma Avelino,
Iborra Sara
Publication year - 2014
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.201300531
Subject(s) - chemistry , catalysis , lewis acids and bases , yield (engineering) , brønsted–lowry acid–base theory , zeolite , organic chemistry , 5 hydroxymethylfurfural , adsorption , mordenite , heterogeneous catalysis , pulmonary surfactant , fatty alcohol , materials science , biochemistry , metallurgy
A new class of biodegradable anionic surfactants with structures based on 5‐alkoxymethylfuroate was prepared starting from 5‐hydroxymethylfurfural (HMF), through a one‐pot–two‐steps process which involves the selective etherification of HMF with fatty alcohols using heterogeneous solid acid, followed by a highly selective oxidation of the formyl group with a gold catalyst. The etherification step was optimized using aluminosilicates as acid catalysts with different pore topologies (H‐Beta, HY, Mordenite, ZSM‐5, ITQ‐2, and MCM‐41), different active sites (Bronsted or Lewis) and different adsorption properties. It was shown that highly hydrophobic defect‐free H‐Beta zeolites with Si/Al ratios higher than 25 are excellent acid catalysts to perform the selective etherification of HMF with fatty alcohols, avoiding the competitive self‐etherification of HMF. Moreover, the 5‐alkoxymethylfurfural derivatives obtained can be selectively oxidized to the corresponding furoic salts in excellent yield using Au/CeO 2 as catalyst and air as oxidant, at moderated temperatures. Both H‐Beta zeolite and Au/CeO 2 could be reused several times without loss of activity.