Highly Effective Production of 5-Hydroxymethylfurfural from Fructose with a Slow-Release Effect of Proton of a Heterogeneous Catalyst,Energy & Fuels

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Highly Effective Production of 5-Hydroxymethylfurfural from Fructose with a Slow-Release Effect of Proton of a Heterogeneous Catalyst
Energy & Fuels ( IF 5.2 ) Pub Date : 2021-10-12 , DOI: 10.1021/acs.energyfuels.1c02693
Xiangbo Song _{1,

2,

3} , Yuhe Liao ₁ , Yuting Zhu _{1,

3} , Pengyao Sun _{1,

3} , Lungang Chen ₁ , Longlong Ma ₁ , Hongwei Yang ₄ , Chenguang Wang ₁

Affiliation

Highly effective production of 5-hydroxymethylfurfural (HMF) from biobased sugar is one of the vital steps for the synthesis of a fuel precursor. In this work, a slow-release effect of proton from a heterogeneous catalyst induced by 1-butyl-3-methylimidazole chloride ([Bmim]Cl) ionic liquids was found and employed to effectively convert biobased fructose to HMF. Under mild conditions of 100 °C and 60 min, a promising HMF yield of 94.6% with a fructose conversion of 99.1% could be achieved in a tetrahydrofuran solvent over the synergy of Amberlyst-15 with [Bmim]Cl, owing to the slow-release effect. Based on extensive control experiments and characterizations, a mechanism of slow release of proton induced by [Bmim]Cl was proposed to better understand the catalytic performance, mainly involving that proton in the −SO₃H group of Amberlyst-15 was gradually replaced by the [Bmim]⁺ of the [Bmim]Cl additive. Additionally, the effect of various parameters (e.g., different ionic liquids and solvents, the loading of the ionic liquid and catalyst, and reaction temperature and time) was systematically investigated. Meanwhile, the stability of Amberlyst-15 and [Bmim]Cl was tested; both could be reused four times. This work provides a novel and highly effective strategy for conversion of biomass-based feedstock toward fuel precursors.

中文翻译：

利用多相催化剂的质子缓释作用从果糖高效生产 5-羟甲基糠醛

从生物基糖高效生产 5-羟甲基糠醛 (HMF) 是合成燃料前体的重要步骤之一。在这项工作中，发现了由 1-丁基-3-甲基咪唑氯化物 ([Bmim]Cl) 离子液体诱导的多相催化剂的质子缓释作用，并将其用于有效地将生物基果糖转化为 HMF。在 100°C 和 60 分钟的温和条件下，由于 Amberlyst-15 与 [Bmim]Cl 的协同作用，在四氢呋喃溶剂中可实现 94.6% 的有希望的 HMF 产率和 99.1% 的果糖转化率，这是由于释放效果。基于广泛的控制实验和表征，提出了 [Bmim]Cl 诱导质子缓慢释放的机制，以更好地了解催化性能，主要涉及 -SO _{3 中的}质子Amberlyst-15的H基团逐渐被[Bmim]Cl添加剂的[Bmim] ⁺取代。此外，系统地研究了各种参数（例如，不同的离子液体和溶剂、离子液体和催化剂的负载以及反应温度和时间）的影响。同时测试了Amberlyst-15和[Bmim]Cl的稳定性；两者都可以重复使用四次。这项工作为将基于生物质的原料转化为燃料前体提供了一种新颖且高效的策略。

更新日期：2021-10-22

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