Efficient Production of 5-Methoxymethyl-2-furfural from Fructose Catalyzed by Amide-Modified Resin

5-Methoxymethyl-2-furfural (MMF) serves as a crucial biobased platform molecule that can be transformed into various high-value chemicals and biobased polyester monomers. However, the current production of MMF still faces several challenges, such as low yield and prolonged reaction time. In this study, we prepared a series of amide-modified strongly acidic resin catalysts and discovered that they have a higher efficiency in converting fructose to prepare MMF in 1-Butyl-3-methylimidazolium chloride ([BMIM]Cl) and methanol. Among the synthesized catalysts, DB757-NMP demonstrated superior performance, achieving an MMF yield of approximately 61.5% under the optimized conditions, with a combined yield of HMF and MMF reaching about 66.6%. The catalyst formation mechanism was analyzed using FTIR, and NMR, confirming the transformation of proton between NMP and the sulfonic acid groups of the resin, which collectively promoted the conversion of fructose to MMF. In addition, we investigated main reasons for catalyst deactivation and successfully restored catalytic activity through regeneration. The regenerated catalyst could be reused for three times with only a slight decrease in MMF yield. The results suggested that DB757-NMP is a more sufficient and recyclable catalyst for the production of MMF from fructose. This work presented a simple and environmentally benign approach for the synthesis of MMF.