1 research outputs found
Etherification Reactions of Furfuryl Alcohol in the Presence of Orthoesters and Ketals: Application to the Synthesis of Furfuryl Ether Biofuels
Strategies
for the efficient transformation of abundant and sustainable
bioderived molecules, such as furfuryl alcohol (FAlc), into higher
value products are currently a vibrant research area. Herein, we demonstrate
that furfuryl ethers, which are of significant interest as biorenewable
fuel additives, are efficiently produced employing an etherification
reaction of furfuryl alcohol and short chain alkyl alcohols in the
presence of a recyclable ZSM-5 catalyst and an orthoester, such as
trimethyl orthoformate (TMOF) or triethyl orthoformate (TEOF), used
as a sacrificial reagent. These etherification reactions proceed at
temperatures significantly lower than those of the previous etherification
procedures, and they provide the furfuryl ether products in high yield.
Importantly, the low temperature employed improves the selectivity
by minimizing the formation of hydrolysis products and the competing
polymerization reactions leading to humin byproducts. By carrying
out the reaction in higher alcohol solvents, such as ethanol, 1-propanol,
and 1-butanol, we are able to capitalize on the ability of ZSM-5 to
catalyze the orthoester exchange reaction of TMOF or TEOF to produce
the corresponding furfuyl ethers in a novel, telescoped orthoester
exchange–etherification reaction sequence. Finally, we also
demonstrate that the etherification reaction proceeds efficiently
in the presence of acetals and ketals, such as dimethoxypropane and
diethoxypropane. This latter development is highly significant given
the greater scope for the regeneration of acetal and ketal reagents