The influence of the initial and catalyst concentrations on the dehydration of d-fructose

Kuster, B.F.M.; Baan, H.S. van der

doi:10.1016/s0008-6215(00)84806-5

Cited by 149 publications

(74 citation statements)

References 12 publications

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“…Studies have shown that the decomposition of glucose in acid is first order in glucose [21,22], so the observed dependence of CMF yield on initial glucose concentration, which would suggest a power law exponent of <1, requires an explanation. Kuster examined the loss of HMF from a 1 M solution in 2 M HCl at 95 C and found that the rehydration of HMF was accelerated by 38% in the presence of either glucose or fructose [23,24]. Van Dam and coworkers found that the decomposition of 1 M HMF in 1 M aqueous HClO 4 at 88 C was accelerated by use of 50% ethylene glycol as co-solvent, but not by addition of an equivalent volume of methanol [25].…”

Section: Primary Productsmentioning

confidence: 99%

“…In contrast, the formation of LA from HMF and glucose is reported to have reaction orders in substrate of 0.88 [30] and 1.09, [28] respectively. Further kinetic studies have been carried out on the formation of humic matter from cellulose [32] and water hyacinth [33], and the effects of the concentration of water [34], acid [24], and the initial concentration of saccharides have been investigated [24]. Despite these studies, the formation of humic matter remains poorly understood.…”

Section: Secondary Productsmentioning

confidence: 99%

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Experimental studies towards optimization of the production of 5-(chloromethyl)furfural (CMF) from glucose in a two-phase reactor

2016

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a b s t r a c t 5-(Chloromethyl)furfural (CMF) is rapidly being established as a renewable platform chemical of great promise. The effects of mass transfer, reaction temperature, Hansen solvent parameters, solvent fraction, and initial glucose concentrations on yields of CMF, 5-(hydroxymethyl)furfural (HMF), 2-(hydroxyacetyl) furan (HAF), levulinic acid (LA), and humic matter were investigated in a two-phase system of 6 M HCl and an organic solvent. The ability of the solvent to extract HMF from the aqueous phase is found to be critical to achieving high CMF yields. Effective solvents must possess at least a small degree of Hansen hydrogen bonding capacity, and a high polarity is beneficial. Yields of CMF and HAF decrease with increasing glucose concentration but the yield of HMF is largely unaffected. The maximum productivity of CMF is achieved at a glucose loading of ca. 1.5 M across all solvent fractions tested.

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Section: Primary Productsmentioning

confidence: 99%

Section: Secondary Productsmentioning

confidence: 99%

Experimental studies towards optimization of the production of 5-(chloromethyl)furfural (CMF) from glucose in a two-phase reactor

2016

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“…Conventionally, the reaction is carried out in water using a Brönsted acid with d-fructose as the preferred carbohydrate source [8][9][10][11][12][13][14][15][16][17][18][19][20]. Hydrochloric acid and sulfuric acid are the most commonly used Brönsted acids.…”

Section: Introductionmentioning

confidence: 99%

Experimental and modelling studies on the uncatalysed thermal conversion of inulin to 5-hydroxymethylfurfural and levulinic acid

Fachri

Abdilla

Rasrendra

et al. 2015

Sustain Chem Process

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Background: 5-Hydroxymethylfurfural (HMF), an important biobased platform chemical, is accessible by the acid catalysed conversion of biopolymers containing hexoses (cellulose, starch, inulin) and monomeric sugars derived thereof. We here report an experimental study on the uncatalysed, thermal conversion of inulin to HMF in aqueous solutions in a batch set-up. Results:The reactions were conducted in a temperature range of 153-187°C, an inulin loading between 0.03 and 0.12 g/mL and batch times between 18 and 74 min using a central composite experimental design. The highest experimental HMF yield in the process window was 35 wt% (45 mol%), which is 45% of the theoretical maximum (78 wt%). The HMF yields were modeled using a statistical approach and good agreement between experiment data and model was obtained. The possible autocatalytic role of formic acid (FA) and levulinic acid, two main byproducts, was probed by performing reactions in the presence of these acids and it was shown that particularly FA acts as a catalyst. Conclusions:Inulin is an interesting feed for the synthesis of HMF in water. A catalyst is not required, though autocatalytic effects of FA play a major role and also affect reaction rates and product yields. Graphical abstract:Chicory 5-hydroxymethylfurfural No catalystInulin

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“…[5,6] Therefore, much effort has been devoted to the dehydration of hexoses into 5-hydroxymethylfurfural (HMF), a versatile and key intermediate both in biofuel chemistry and the petroleum industry. [7][8][9] In literature, acidic catalysts have been employed for the d-fructose dehydration reaction, such as mineral acids, [10,11] strong acid cation exchange resins, [12][13][14] H-form zeolites, [14,16] supported heteropolyacids, [17] and metal ions. [18,19] In addition, several reaction media, including pure water and organic solvents, and also a number of biphasic water/organic systems, have been adopted.…”

Section: Introductionmentioning

confidence: 99%

Efficient and Selective Dehydration of Fructose to 5‐Hydroxymethylfurfural Catalyzed by Brønsted‐Acidic Ionic Liquids

2010

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The dehydration of D‐fructose and glucose has been studied with acidic ionic liquids as catalysts. A series of Brønsted‐acidic ionic liquids has been synthesized and tested in the dehydration of D‐fructose. The results showed that N‐methyl‐2‐pyrrolidonium methyl sulfonate [NMP]+[CH3SO3]− and N‐methyl‐2‐pyrrolidonium hydrogen sulfate [NMP]+[HSO4]− have high catalytic activity. Highly efficient and selective dehydration of D‐fructose to 5‐hydroxymethylfurfural (HMF) was achieved in dimethyl sulfoxide (DMSO) under mild conditions. For example, a 72.3 % yield of HMF with 87.2 % selectivity were obtained for 2 h at 90 °C in the presence of 7.5 mol % [NMP]+[CH3SO3]−. The effects of the reaction temperature, time, and solvent were investigated in detail. The catalyst and solvent can be recycled for the dehydration of D‐fructose. The Hammett method was used to determine the acidities of these ionic liquids, which indicated that the acidity and molecular structure have strong effects on the catalytic activity of ionic liquids. Based on the experimental results, a possible reaction mechanism for the dehydration of D‐fructose is proposed.

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The influence of the initial and catalyst concentrations on the dehydration of d-fructose

Cited by 149 publications

References 12 publications

Experimental studies towards optimization of the production of 5-(chloromethyl)furfural (CMF) from glucose in a two-phase reactor

Experimental studies towards optimization of the production of 5-(chloromethyl)furfural (CMF) from glucose in a two-phase reactor

Experimental and modelling studies on the uncatalysed thermal conversion of inulin to 5-hydroxymethylfurfural and levulinic acid

Efficient and Selective Dehydration of Fructose to 5‐Hydroxymethylfurfural Catalyzed by Brønsted‐Acidic Ionic Liquids

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