Solvent effect on xylose-to-furfural reaction in biphasic systems: combined experiments with theoretical calculations. Issue 21 (13th October 2021)

• Record Type: Journal Article
• Authors: Lin, Qixuan; Zhan, Qiwen; Li, Rui; Liao, Shouwei; Ren, Junli; Peng, Feng; Li, Libo
• Is Part Of: Green chemistry. Volume 23:Issue 21(2021)
• Page Start: 8510
• Page End: 8518
• Publication Date: 2021-10-13
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/d1gc02812j
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : The promotion efficiency of organic solvents in biphasic systems for furfural production is influenced by four factors, and the most important factor is the solvation free energy of furfural (Δ G sol-ff ) in organic solvents. Abstract : The present report focuses on the solvent effect on furfural production from xylose in biphasic systems with methods including combined experiments, molecular dynamics (MD) simulations and density functional theory (DFT) calculations. Six most effective and commonly used biphasic solvents for furfural production were comparatively analyzed and discussed based on the kinetic study, partition coefficient, degradation behavior of furfural in organic solvents, distribution of solvent molecules around xylose/furfural molecules, hydrogen bonding, moving trajectories of xylose/furfural, and the solvation free energy. During the hydrothermal reaction of xylose to furfural in biphasic systems, it was found that the conversion efficiency of biphasic systems can be ordered as DCM/H2 O > 2-MTHF/H2 O > 2-butanol/H2 O ≈ MIBK/H2 O > CPME/H2 O > toluene/H2 O according to the xylose conversion and furfural yield, which are dominated by the solvation free energy (Δ G sol ) of furfural in organic solvents, and also be affected by three other factors, namely, the maximum solubility of furfural in organic solvents, the Δ G sol value of organic solvents in water, and the side reaction of furfural in organic solvents. The degradation rate of furfural in 2-butanol was detected to be the fastest, and molecular dynamics simulation data showed that the hydrogen bonding between furfural and 2-butanol may accelerate the degradation of furfural. DCM has excellent extraction ability for furfural, and the maximum furfural yield in the DCM/H2 O system (81.64%) is much higher than that in other systems during the hydrothermal reaction without additional catalysts.