A novel route towards high yield 5-hydroxymethylfurfural from fructose catalyzed by a mixture of Lewis and Brönsted acids

Liu, Yingxin; Li, Zhenbin; Yang, Yao; Hou, Yaxin; Wei, Zuojun

doi:10.1039/c4ra04906c

Cited by 23 publications

(10 citation statements)

References 47 publications

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“…Hereby, the yield and selectivity of HMF were found to be primarily controlled by the solvent compositions because of their determination on predominant existence of tautomers . In that case, recent progresses on the tautomeric distributions of glucose and fructose in various solvents (e. g., methanol; N,N‐dimethylformamide (DMF); aqueous solutions containing tetrahydrofuran (THF), ethanol, or DMSO; lower alcohols/DMSO‐ d 6 mixtures; ZnCl 2 molten salt hydrate medium; and typical basic, neutral and acidic deep eutectic solvents (DES)) through quantitative 13 C NMR spectra analysis might be useful for predicating the reactivity of glucose and fructose in various solvents. In addition, theoretical calculations also exhibit promise for indicating the tautomer distributions of hexose .…”

Section: Insights Into the Complex Reaction Network Of Glucose‐to‐hmfmentioning

confidence: 99%

Controlling the Reaction Networks for Efficient Conversion of Glucose into 5‐Hydroxymethylfurfural

Zhu

et al. 2020

ChemSusChem

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Biomass-derived hexose constitutes the main component of lignocellulosic biomass for producing value-added chemicals and biofuels. However, the reaction network of hexose is complicated, which makes the highly selective synthesis of one particular product challenging in biorefinery. This Review focuses on the selective production of 5-hydroxymethylfurfural (HMF) from glucose on account of its potential significance as an important platform molecule. The complex reaction network involved in glucose-to-HMF transformations is briefly summarized. Special emphasis is placed on analyzing the complexities of feedstocks, intermediates, (side-) products, catalysts, solvents, and their impacts on the reaction network. The strategies and representative examples for adjusting the reaction pathway toward HMF by developing multifunctional catalysts and promoters, taking advantage of solvent effects and process intensification, and synergizing all measures are comprehensively discussed. An outlook is provided to highlight the challenges and opportunities faced in this promising field. It is expected to provide guidance to design practical catalytic processes for advancing HMF biorefinery.

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Section: Insights Into the Complex Reaction Network Of Glucose‐to‐hmfmentioning

confidence: 99%

Controlling the Reaction Networks for Efficient Conversion of Glucose into 5‐Hydroxymethylfurfural

Zhu

et al. 2020

ChemSusChem

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“…Based on these facts, the production of HMF from fructose has been extensively studied. Traditional mineral acids such as H2SO4 and H3PO4 are efficient for fructose dehydration (Qi et al 2014;Liu et al 2014). However, they are highly corrosive and difficult to recycle, so they cannot meet the principles of green chemistry.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Conversion of Biomass-derived Carbohydrates into 5-Hydroxymethylfurfural using a Strong Solid Acid Catalyst in Aqueous γ-Valerolactone

Li¹,

Xu²,

Zhang³

et al. 2016

BioResources

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Selective conversion of biomass-derived carbohydrates into 5-hydroxymethylfurfural (HMF) is of great significance for biomass conversion. In this study, a novel solid Brønsted acid was prepared simply by the copolymerization of paraformaldehyde and p-toluenesulfonic acid and then used to catalyze the conversion of various carbohydrates into HMF in γ-valerolactone-water (GVL/H2O) reaction medium for the first time. The catalyst exhibited strong acidity, good water resistance, and high thermal stability. The present work focuses on the effects of various reaction parameters, including reaction temperature, time, water concentration, solvent, fructose level, and catalyst loading, on fructose dehydration. The catalyst exhibited excellent catalytic performance for HMF production from fructose in GVL and furnished a high HMF yield of 78.1% at 130 °C in 30 min. The recycling experiments suggested that the solid acid catalyst could be recycled at least seven times without a noticeable decrease in the catalytic activity. In addition, an attempt to study the one-step conversion of sucrose, glucose, and cellulose into HMF and furfural was performed using the same catalytic system.

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“…Indeed, when reaction was carried out in water/dioxane mixtures, ∼ 60 and ∼80% HMF yields have been obtained from fructose and 90% high-fructose corn syrup (HFCS 90), respectively. Although the presence of water can partially facilitate the hydration of HMF to levulinic acid and humins, ,, carrying out the reaction in pure dioxane has been reported to afford low (∼30%) HMF yields, − presumably due to the low solubility of the fructose starting materials in this solvent. , …”

Section: Resultsmentioning

confidence: 99%

Matching the Activity of Homogeneous Sulfonic Acids: The Fructose-to-HMF Conversion Catalyzed by Hierarchically Porous Sulfonic-Acid-Functionalized Porous Organic Polymer (POP) Catalysts

Agrawal

Chakraborty

et al. 2019

ACS Sustainable Chem. Eng.

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Three HO3S-functionalized porous organic polymers (HO3S-POPs) with high surface areas (500–700 m2/g) and a broad range of porosity profiles were synthesized and tested against homogeneous-acid analogs and commercially available acid resins to evaluate their relative catalytic activities in the acid-catalyzed conversion of fructose to HMF. Comparison of fructose conversions and HMF yields demonstrates that the sulfonated POPs with hierarchical porosity can achieve catalytic activities that rival those of their homogeneous counterparts. The associated HMF selectivities represent optimized values that increase with higher temperature and faster heating, both of which can reduce the reaction time and limit product decomposition. Due to their intrinsically high mesoporosity and number of accessible acid sites, these HO3S-POPs also outperform the commercially available Amberlyst 15 resin catalyst and its crushed variant.

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A novel route towards high yield 5-hydroxymethylfurfural from fructose catalyzed by a mixture of Lewis and Brönsted acids

Abstract: The formed fructose-phosphate-AlCl3 complex dehydrates along the pathway to 5-HMF in the presence of a high proton concentration provided by H2SO4, leading to a high yield of 5-HMF.

Cited by 23 publications

References 47 publications

Controlling the Reaction Networks for Efficient Conversion of Glucose into 5‐Hydroxymethylfurfural

Controlling the Reaction Networks for Efficient Conversion of Glucose into 5‐Hydroxymethylfurfural

Catalytic Conversion of Biomass-derived Carbohydrates into 5-Hydroxymethylfurfural using a Strong Solid Acid Catalyst in Aqueous γ-Valerolactone

Matching the Activity of Homogeneous Sulfonic Acids: The Fructose-to-HMF Conversion Catalyzed by Hierarchically Porous Sulfonic-Acid-Functionalized Porous Organic Polymer (POP) Catalysts

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