Righetti Grazia Isa C, Di Pietro Maria Enrica, Leonardi Gabriella, Sinibaldi Arianna, Mezzetta Andrea, Guazzelli Lorenzo, Mele Andrea
Department of Chemistry, Materials and Chemical Engineering "G. Natta", Politecnico di Milano, Piazza L. da Vinci 32, 20133 Milano, Italy.
Dipartimento di Farmacia, Università di Pisa, Via Bonanno 6, 56126 Pisa, Italy.
ACS Sustain Chem Eng. 2025 Apr 2;13(18):6518-6527. doi: 10.1021/acssuschemeng.4c10788. eCollection 2025 May 12.
The potential of 5-hydroxymethylfurfural (HMF) as a platform chemical for sustainable biobased products is widely recognized. However, its practical applications are often constrained by stability challenges. This study examines the solubility and chemical stability of HMF in 15 paradigmatic deep eutectic solvents (DES), formed by combining five hydrogen bond acceptors (HBAs: betaine, choline chloride, choline acetate, L-carnitine, and l-proline) and three hydrogen bond donors (HBDs: glycerol, ethylene glycol, and levulinic acid). Our findings reveal that HMF demonstrates high solubility and remarkable stability across the studied DES. Only a few cases of HMF degradation were observed and discussed, with specific degradation pathways identified in certain solvent mixtures. Notably, the HBAs within the DES play a crucial role in significantly enhancing the stability of HMF, establishing a foundation for its use as a renewable synthon in organic chemistry using environmentally benign solvents. These findings represent a significant step forward in aligning the synthetic design with the principles of green chemistry.
5-羟甲基糠醛（HMF）作为可持续生物基产品的平台化学品的潜力已得到广泛认可。然而，其实际应用常常受到稳定性挑战的限制。本研究考察了HMF在15种典型的低共熔溶剂（DES）中的溶解度和化学稳定性，这些低共熔溶剂由五种氢键受体（HBA：甜菜碱、氯化胆碱、醋酸胆碱、L-肉碱和L-脯氨酸）和三种氢键供体（HBD：甘油、乙二醇和乙酰丙酸）组合而成。我们的研究结果表明，HMF在所研究的DES中表现出高溶解度和显著的稳定性。仅观察并讨论了少数几例HMF降解情况，并在某些溶剂混合物中确定了特定的降解途径。值得注意的是，DES中的HBA在显著提高HMF的稳定性方面起着关键作用，为其在使用环境友好型溶剂的有机化学中用作可再生合成子奠定了基础。这些研究结果代表了在使合成设计符合绿色化学原则方面向前迈出的重要一步。
