Facile synthesis of furfuryl ethyl ether in high yield via the reductive etherification of furfural in ethanol over Pd/C under mild conditions

Abstract

Furfuryl ethyl ether (FEE) was synthesized from furfural via reductive etherification in 81% yield over a Pd/C catalyst under mild conditions.

Synthesis of Biomass‐Derived Ethers for Use as Fuels and Lubricants

“…demonstrated that Pd supported on TiO 2 , Al 2 O 2 , SiO 2 , and active carbon are also effective for the reductive etherification of furfural with ethanol at 333 K with 0.3 MPa of H 2 . Yields of up to 81 % of furfuryl ethyl ether (FEE) were obtained over 0.7 wt % Pd/C with minor formation of 2‐(diethoxymethyl)furan (4 %), furfuryl alcohol (10 %), and tetrahydrofurfuryl alcohol (3 %) . The authors suggested that palladium hydride, formed in situ, catalyzes the formation of the key intermediate, 2‐(diethoxymethyl)furan .…”

“…The authors suggested that palladium hydride, formed in situ, catalyzes the formation of the key intermediate, 2‐(diethoxymethyl)furan . They also suggested that the key to achieving a high yield of ether is the balance between the proton‐donating ability and hydrogenolysis activity of palladium hydride, which requires tuning of Pd loading, hydrogen pressure, and reaction temperature …”

Synthesis of Ethyl‐4‐ethoxy Pentanoate by Reductive Etherification of Ethyl Levulinate in Ethanol on Pd/SiO2‐C Catalysts

“…have reported the reductive etherification of 5‐(hydroxymethyl)furfural catalyzed by a supported Pt/alumina catalyst in the presence of Amberlyst‐15. This method also applies to furfural in both methanol and ethanol by using carbon‐supported noble metal nanoparticles as the catalyst, albeit under different reaction conditions . We found that Pd/C can efficiently catalyze the reductive etherification of furfural in ethanol under mild conditions (0.3 MPa H 2 and 60 °C) .…”

“…Reductive etherification of carbonyl compounds provides an alternative methodology for the preparation of biomass‐derived ethers . Balakrishnan et al .…”

“…This method also applies to furfural in both methanol and ethanol by using carbon‐supported noble metal nanoparticles as the catalyst, albeit under different reaction conditions . We found that Pd/C can efficiently catalyze the reductive etherification of furfural in ethanol under mild conditions (0.3 MPa H 2 and 60 °C) . Tulchinsky and Briggs recently reported the synthesis of alkyl 4‐alkoxypentanoates by simultaneous esterification and reductive etherification by using levulinic acid as the precursor, where Pd/C was used as the catalyst under a hydrogen pressure of 100–700 psig (1 psig=6.895 kPa) at 200–220 °C .…”