One-Pot Synthesis of 5-(Ethoxymethyl)furfural from Glucose Using Sn-BEA and Amberlyst Catalysts

Abstract

5-(Ethoxymethyl)furfural (EMF) was produced from glucose in ethanol in a single reactor at 90 °C. The reaction proceeds via the isomerization of glucose to fructose with zeolite Sn-Beta, a Lewis acid catalyst. Fructose is converted to 5-(hydroxymethyl)furfural, which is then etherified to EMF using a Brønsted acid catalyst, Amberlyst 131. An EMF yield of 31% was achieved.

State of the art of Lewis acid-containing zeolites: lessons from fine chemistry to new biomass transformation processes

“…40a Unfortunately, the achieved yields of furfural are very low (20%wt) due to the reaction is carried out in a single aqueous phase, and then, the formed furfural can undergo undesired degradation reactions in presence of Brönsted acids. 61 This is a very interesting reaction because EMF has been proposed as a potential biofuel alternative, presenting an energy density similar to gasoline (30.3 MJ/L). 62 Taking as a reference the previous work of Nikolla et al, 60 where high HMF yields can be achieved by combining Lewis and Brönsted acids, Tsapatsis et al are able to introduce a new catalytic step to efficiently transform HMF into EMF using the Brönsted acid catalyst (Amberlyst 131, see Figure 10).…”

Insights into the Metal Salt Catalyzed 5-Ethoxymethylfurfural Synthesis from Carbohydrates

“…By contrast, the transformation of glucose to EMF is much difficult owing to the demand of isomerization into fructose firstly, and the above developed catalysts had low reactivity. Presently, two combined catalyst systems consisting of zeolite and Amberlyst exhibited good catalytic activity for EMF synthesis from glucose [19,20]. Although significant advances have been made from persistent research, obstacles of using the heterogeneous catalysts include the complex preparation of the catalyst, expensive catalyst cost, and/or limited substrate adaptability.…”

Zeolite Catalysis for Biomass Conversion

“…Promising yields can also be obtained using solid Brønsted acids instead of mineral acids. For a system employing a combination of Sn-BEA with Amberlyst-131 in ethanol at temperatures as low as 90 °C, ethoxymethylfurfural was obtained in yields up to 31 % from glucose [ 78 ]. A signifi cant factor contributing to this moderate yield is the competing retroaldol reaction, which will be discussed later in this chapter.…”