Conversion of glucose into 5-hydroxymethylfurfural catalyzed by acid–base bifunctional heteropolyacid-based ionic hybrids,Green Chemistry

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Conversion of glucose into 5-hydroxymethylfurfural catalyzed by acid–base bifunctional heteropolyacid-based ionic hybrids
Green Chemistry ( IF 9.3 ) Pub Date : 2018-02-20 00:00:00 , DOI: 10.1039/c7gc03821f
Pingping Zhao _{1,

2,

3,

4} , Yunyun Zhang _{1,

2,

3,

4} , Yong Wang _{1,

2,

3,

4} , Hongyou Cui _{1,

2,

3,

4} , Feng Song _{1,

2,

3,

4} , Xiuyu Sun _{1,

2,

3,

4} , Lipeng Zhang _{1,

2,

3,

4}

Affiliation

The design of stable acid–base bifunctional heterogeneous catalysts has become crucial for efficient catalytic conversion of renewable biomass to high value-added chemicals. Heteropolyacids (HPAs) are of great interest due to their unique tunable structures and suitable acidity. In this study, a series of acid–base bifunctional ionic hybrid catalysts [MimAM]_nH_3−nPW₁₂O₄₀ (n = 1–3) were synthesized by the ion exchange method using an amino-functionalized imidazolium ionic liquid and H₃PW₁₂O₄₀ as precursors. The introduction of the ionic liquid resulted in a varied Lewis–Brønsted acidity for [MimAM]_nH_3−nPW₁₂O₄₀. The synergistic effect of dual acidic properties endowed [MimAM]H₂PW₁₂O₄₀ with more efficiency for glucose dehydration in THF/H₂O–NaCl with 53.9% HMF yield. A unique sequential hydrogen transfer mechanism is proposed to understand the efficient heterogeneous catalysis. Among them, the absence of fructose and levoglucosenone in glucose dehydration may come from the formation of stabilized intermediates 1,2-enediol and anhydrosugars due to the existence of an effective hydrogen bond between O–H and O [double bond, length as m-dash]

W on the heteropoly anion; the reversible process between glucose dehydration and anhydrosugar hydration is responsible for the absence of HMF during the early stage of reaction. This work provides a deep understanding of the HPA-catalyzed conversion of glucose to HMF.

中文翻译：

酸基双官能杂多酸基离子杂化物催化将葡萄糖转化为5-羟甲基糠醛

稳定的酸碱双功能多相催化剂的设计对于将可再生生物质高效催化转化为高附加值化学品至关重要。杂多酸（HPA）由于其独特的可调结构和适当的酸度而备受关注。在这项研究中，使用氨基官能化的咪唑鎓离子液体和H，通过离子交换法合成了一系列酸碱双官能离子杂化催化剂[MimAM] _n H _{3− n} PW ₁₂ O ₄₀（n = 1–3）。₃ PW ₁₂ O ₄₀作为前体。离子液体的引入导致[MimAM] _n的Lewis-Brønsted酸度发生变化H _{3- n} PW ₁₂ O ₄₀。双酸性质的协同作用赋予[MimAM] H ₂ PW ₁₂ O ₄₀更高的THF / H ₂ O-NaCl葡萄糖脱水能力，HMF收率达53.9％。为了理解有效的多相催化作用，提出了一种独特的顺序氢转移机理。其中，由于OH和O之间存在有效的氢键，葡萄糖脱水中不存在果糖和左旋葡糖酮的原因可能是稳定的中间体1,2-烯二醇和脱水糖的形成。 [双键，长度为m-破折号]