Production of a renewable 1,3-diene containing a functional group from a furfural–acetone adduct in a fixed-bed reactor

Abstract

The synthesis of functionalized 1,3-dienes has received increasing attention due to their importance in the practical development of high-performance elastomers. In the present work, furfural and acetone, acting as renewable feedstocks, are first employed to produce a functionalized 1,3-diene containing a furan group (1-(2-furyl)-1,3-butadiene, F-diene). After selective hydrogenation of the CO group, the aldol adduct (4-(2-furanyl)-3-buten-2-ol, FAH) shows a nearly complete conversion, with an excellent selectivity (as high as 92%) towards F-diene over ceria-based catalysts in a fixed bed. BET, TEM, XRD, XPS, Raman, TPD, TPR and TGA were conducted to identify the relationship between the catalytic performance and catalyst structure. A plausible reaction pathway for the dehydration of FAH over ceria-based catalysts was proposed using a radical mechanism, which suggested the importance of the Ce⁴⁺–Ce³⁺ redox cycle for the dehydration of FAH to F-diene. Furthermore, the ceria-based catalysts exhibited a notable carbon resistance.