The Cascade Transformation of Furfural to Cyclopentanone: A Critical Evaluation Concerning Feasible Process Development

Furfural is a fascinating bio-based platform molecule that can be converted into useful cyclic compounds, among others. In this work, the hydrogenative rearrangement-dehydration of furfural towards cyclopentanone using a commercially available Pt/C catalyst was investigated in terms of its reaction performance to assess its feasibility as an industrial process. However, acquiring an acceptable cyclopentanone yield proved very difficult, and the reaction was constrained by unforeseen parameters, such as the relative liquid volume in the reactor and the substrate concentration. Most strikingly, the sacrificial formation of furanoic oligomers that precipitated onto the catalyst’s surface was a troublesome key factor that mediated the product’s selectivity versus the carbon mass balance. By applying a biphasic water–toluene solvent system, the yield of cyclopentanone was somewhat improved to a middling 59%, while tentatively positive distributions of reaction components over these solvent phases were observed, which could be advantageous for anticipated down-stream processing. Overall, the sheer difficulty of controlling this one-pot cascade transformation towards a satisfactory product output under rather unfavorable reaction parameters renders it unsuitable for industrial process development, and a multi-step procedure for this chemical transformation might be considered instead.