Efficient process for conversion of fructose to 5-hydroxymethylfurfural with ionic liquids

Qi, Xinhua; Watanabe, Masaru; Aida, Taku Michael; Smith, Richard L.

doi:10.1039/b905975j

Cited by 284 publications

(227 citation statements)

References 27 publications

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“…6b), resulting in an activation energy and pre-exponential factor of 138 kJ mol -1 and 4.7 9 10 17 min -1 , respectively. This activation energy is considerably higher than provided by Qi et al [19] (115 kJ mol -1 ) for the conversion of D-glucose to HMF in an ionic liquid ([BMIM]Cl) using CrCl 3 as the catalysts, though considerably lower than the value reported by Girisuta et al [20] for the conversion of D-glucose in water using sulphuric acid as the catalyst (152 kJ mol -1 ).…”

Section: Kinetic Studiescontrasting

confidence: 42%

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The Catalytic Conversion of d-Glucose to 5-Hydroxymethylfurfural in DMSO Using Metal Salts

et al. 2012

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A wide range of metal halides and triflates were examined for the conversion of D-glucose to HMF in DMSO. Chromium and aluminium salts were identified as the most promising catalysts. The effect of process variables like initial D-glucose concentration (0.1-1.5 M), reaction time (5-360 min) and reaction temperature (100-140°C) on the yield of HMF were examined at a fixed Al(OTf) 3 concentration (50 mM). Highest yields of HMF (60 mol%) were obtained using 1 M D-glucose (16 wt%), Al(OTf) 3 (5 mol%) at a temperature of 140°C. A reaction pathway involving initial isomerisation of D-glucose to D-fructose followed by a number of dehydration steps is proposed. Kinetic analysis reveals that the reaction is second order in D-glucose with an activation energy of 138 kJ mol -1 .

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Section: Kinetic Studiescontrasting

confidence: 42%

“…6a) compared to a first order approach (R 2 \ 0.9 for T [ 100°C). Kinetic data for the catalytic reaction are scarce, the only example reported so far is for an ionic liquid system with CrCl 3 as the catalysts [19]. Here, a reaction order of one in D-glucose was found.…”

Section: Kinetic Studiesmentioning

confidence: 92%

The Catalytic Conversion of d-Glucose to 5-Hydroxymethylfurfural in DMSO Using Metal Salts

et al. 2012

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“…Nafion 117 (20 wt % loading vs. xylose) produced the highest furfural yield at 60 %, with a selectivity of 66 % in 2 h at 150 8C (Table 1, entry 5), although a yield of 59 % was also achieved at 175 8C after only 0.5 h with 20 wt % catalyst loading versus xylose (Table 1, entry 6). The higher yield of Nafion 117 with increasing catalyst loading can be attributed to the greater number of available sulfonic acid sites [13,14] per unit weight relative to SAC-13, the weight of which mainly comprises the amorphous silica support. Also, the reduced yield of SAC-13 compared to Nafion 117 might be due to the interaction of the Nafion polymer with the silanol groups, which would decrease the availability of the sulfonic acid groups to participate in catalysis.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Furfural from Xylose by Heterogeneous and Reusable Nafion Catalysts

et al. 2011

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Nafion 117 has been proven as a robust and reusable heterogeneous catalyst for the dehydration of 9.1 % (w/w) xylose in dimethyl sulfoxide (DMSO) to yield 60 % furfural in 2 h at 150 °C. The catalytic high activity promoted shorter reaction times to limit the formation of side‐products which otherwise would lead to decreased yields. Within the allowable operating temperature range of Nafion (125 to 175 °C), the reaction was kinetically controlled. In corroboration with AFM and SEM imaging, ATR–FTIR confirmed that the Nafion catalytic activity remained unchanged after 15 repeated uses. With excellent chemical and thermal stability under the conditions for xylose dehydration compared to existing solid acid catalysts, this reusable Nafion system could be a step towards the more economical production of furfural from renewable biomass, an intermediate chemical for the preparation of value‐added chemicals.

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“…[6] Therefore, research into the production of HMF from fructose has been studied extensively for a long time. Many catalysts, such as acidic resin, [7] Lewis acids, [8] mineral acids, [9] organic carboxylic acids, [5a] and acidic ILs, [10] have been applied to this conversion successfully. Regardless of these developments, it remains a challenge to obtain HMF from carbohydrates in terms of efficiency and greenness.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Conversion of Inulin and Fructose into 5‐Hydroxymethylfurfural by Lignosulfonic Acid in Ionic Liquids

Xie¹,

Zhao²,

Wang³

2012

ChemSusChem

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In this work, we found that lignosulfonic acid (LS), which is a waste byproduct from the paper industry, in ionic liquids (ILs) can catalyze the dehydration of fructose and inulin into 5‐hydroxymethylfurfural (HMF) efficiently, which is a promising potential substitute for petroleum‐based building blocks. The effects of reaction time, temperature, catalyst loading, and reusability of the catalytic system were studied. It was found that a 94.3 % yield of HMF could be achieved in only 10 min at 100 °C under mild conditions. The reusability study of the LS–IL catalytic system after removal of HMF by ethyl acetate extraction demonstrated that the catalytic activity decreased from 77.4 to 62.9 % after five cycles and the catalytic activity could be recovered after simply removing the accumulated humins by filtration after adding ethanol to the LS–ILs. The integrated utilization of a biorenewable feedstock, catalyst, and ILs is an example of an ideal green chemical process.

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Efficient process for conversion of fructose to 5-hydroxymethylfurfural with ionic liquids

Cited by 284 publications

References 27 publications

The Catalytic Conversion of d-Glucose to 5-Hydroxymethylfurfural in DMSO Using Metal Salts

The Catalytic Conversion of d-Glucose to 5-Hydroxymethylfurfural in DMSO Using Metal Salts

Synthesis of Furfural from Xylose by Heterogeneous and Reusable Nafion Catalysts

Catalytic Conversion of Inulin and Fructose into 5‐Hydroxymethylfurfural by Lignosulfonic Acid in Ionic Liquids

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