(282f) Towards the Upscale Production of Diformylxylose As a Solvent and a Platform Chemical

The chemical industry is facing increasing pressure to replace fossil-based and often toxic solvents with renewable alternatives. We recently introduced diformylxylose (DFX) as a promising bioderived polar aprotic solvent with properties resembling fossil fuel-derived analogues in benchmark reactions.[1] Additionally, DFX has been shown to act as a platform chemical to produce furfural, xylitol and other aldehyde-protected xylose derivatives.[2] Although an acid-catalyzed one-step reaction was proposed to obtain DFX from commercial xylose and formalin, scalability and economic feasibility still require significant improvement.

In this study, various effective reaction systems were discovered to scale up DFX production in organic and/or aqueous solutions catalyzed by homogenous acid or heterogenous catalysts, attaining a DFX yield of up to 86%. An optimized aqueous system is of particular interest as it is more environmentally friendly and xylose containing water is often considered waste in biorefineries. In our scenario, the waste can be converted to a value-added chemical despite a slightly lower yield (ca. 60%). To improve the DFX yield, organic solvents are being explored as in-situ extractants in a biphasic reaction. Apart from that, the synthesis of DFX with acid in 2-Me-THF was optimized and successfully scaled up. The identified conditions were tested in a 15L reactor and yielded ca. 3 kg of DFX after a 3h reaction. A continuous process was also designed using ASPEN Plus based on the experimental data with solvent recycling, achieving a cost of production at 2.5 USD/kg on par with commercial alternatives. Additionally, a new heterogeneous method was identified to replace unrecyclable acid, showing comparable DFX yield and productivity. The cost-effectiveness and flexibility of DFX synthesis shown here could facilitate its large-scale production and the industrialisation of a new bio-based solvent.

References

[1] Anastasia O. Komarova, Dick GR, Luterbacher J. Diformylxylose as a New Polar Aprotic Solvent Produced from Renewable Biomass. Green Chem 2021. https://doi.org/10.1039/d1gc00641j.

[2] Questell-Santiago YM, Yeap JH, Talebi Amiri M, Le Monnier BP, Luterbacher JS. Catalyst Evolution Enhances Production of Xylitol from Acetal-Stabilized Xylose. ACS Sustain Chem Eng 2020;8:1709–14. https://doi.org/10.1021/acssuschemeng.9b06456.