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Unveiling the catalytic effects of Brønsted acidic ionic liquid on quantitative α-glucose conversion to 5-HMF: Experimental and computational studies

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  • Abdullayev, Yusif
  • Ahmadov, Orkhan
  • Valadova, Gunay
  • Karimli, Ayan
  • Autschbach, Jochen

Abstract

Effective biomass conversion to 5-HMF(5-hydroxymethylfurfural) is still a challenge and needs to be improved because of the 5-HMF importance as building blocks for valuable monomers and fuel precursors. We suggest for the first time utilization of low-cost metal-free Brønsted acidic Ionic liquid (IL) N,N-Diethyl-1,4-phenylenediamine hydrogen sulfate, [DPhDA]HSO4 as a catalyst for the α-glucose dehydration to 5-HMF. Quantitative α-glucose conversion is achieved via optimizing the reaction condition: 91.4% 5-HMF yield with 30 mol% [DPhDA]HSO4 in the presence of DMSO as a solvent at 160 °C in 30 min (TOF 6.1 h−1). 3-fold increase in reaction time leads to higher (94%) 5-HMF yield at 160 °C with lower TOF 1.6 h−1. The IL surprising catalytic performance is scrutinized with its amphiprotic nature (availability of basic and acidic spots in its structure (Fig. 1)). Further computational mechanistic studies revealed the function of the catalytic sites in the α-glucose dehydration. We calculated five-membered ring formation and water extrusion in one concerted transition state (TS2A, ΔG‡ = 38.8 kcal/mol) following the α-glucose ring-opening (TS1, ΔG‡ = 20.4 kcal/mol). Further four steps (sp3-s, C–H bond cleavages (TS3, TS6) and dehydroxylation (TS4A, TS5)) are quite straightforward to reach the product (5-HMF).

Suggested Citation

  • Abdullayev, Yusif & Ahmadov, Orkhan & Valadova, Gunay & Karimli, Ayan & Autschbach, Jochen, 2021. "Unveiling the catalytic effects of Brønsted acidic ionic liquid on quantitative α-glucose conversion to 5-HMF: Experimental and computational studies," Renewable Energy, Elsevier, vol. 171(C), pages 383-390.
    • Handle: RePEc:eee:renene:v:171:y:2021:i:c:p:383-390
    DOI: 10.1016/j.renene.2021.02.119
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    1. Qian, Yong & Zhu, Lifeng & Wang, Yue & Lu, Xingcai, 2015. "Recent progress in the development of biofuel 2,5-dimethylfuran," Renewable and Sustainable Energy Reviews, Elsevier, vol. 41(C), pages 633-646.
    2. Jan-Georg Rosenboom & Diana Kay Hohl & Peter Fleckenstein & Giuseppe Storti & Massimo Morbidelli, 2018. "Bottle-grade polyethylene furanoate from ring-opening polymerisation of cyclic oligomers," Nature Communications, Nature, vol. 9(1), pages 1-7, December.
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    1. Niakan, Mahsa & Masteri-Farahani, Majid & Seidi, Farzad, 2022. "Efficient glucose-to-HMF conversion in deep eutectic solvents over sulfonated dendrimer modified activated carbon," Renewable Energy, Elsevier, vol. 200(C), pages 1134-1140.

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