Synthesis of 5-hydroxymethylfurfural (HMF) by acid catalyzed dehydration of glucose–fructose mixtures

Pedersen, Asbjørn Toftgaard; Ringborg, Rolf Hoffmeyer; Grotkjær, Thomas; Pedersen, Sven; Woodley, John M.

doi:10.1016/j.cej.2015.03.094

Cited by 120 publications

(65 citation statements)

References 43 publications

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“…Typically,t heseh ydrolyses are carried out by using homogeneous acids (HCl, H 2 SO 4 ,e tc.) [9,10] The direct dehydration of fructose to 5-HMFw as also reported. [6,7] Considering the reaction pathway summarized in Scheme 1, levulinic acid (ine quimolar quantities as formic acid) is produced by the rehydration and subsequent oxidation of HMF molecules, previously generatedi nt he fructose dehydration.F ructose is obtained by isomerization of glucose molecules, with this step being considereda st he limiting step.…”

Section: Introductionsupporting

confidence: 53%

“…[10] This approach also allows us determine the homogeneous and heterogeneous contribution to the global kinetic. [10] This approach also allows us determine the homogeneous and heterogeneous contribution to the global kinetic.…”

Section: Resultsmentioning

confidence: 99%

“…[10] This approach also allows us determine the homogeneous and heterogeneous contribution to the global kinetic. [10,26] Different researchers have concluded that direct dehydration of glucose into HMF is also possible, but the typical kinetics are significantly slower than the corresponding to dehydration via previous isomerization. Thus, the glucose isomerizationt of ructose is ar eversible reaction, with first-order dependence.…”

Section: Resultsmentioning

confidence: 99%

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Aqueous‐Phase Transformation of Glucose into Hydroxymethylfurfural and Levulinic Acid by Combining Homogeneous and Heterogeneous Catalysis

Garcés¹,

Faba²,

Dı́az³

et al. 2019

ChemSusChem

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Homogeneous (HCl) and heterogeneous catalysts (various zeolites) were combined to enhance the upgrading of glucose into two different platform molecules: 5‐hydroxymethylfurfural (HMF) and levulinic acid (LA). β‐Zeolite was the most active material for the glucose isomerization to fructose, improving also the activity of HCl for the subsequent steps. Reaction time, temperature, and pH were then modified, identifying 140 °C, 200 ppm of HCl, and 5 h as the optimum conditions for HMF formation (41 % selectivity; 0.06 mol L−1) and 140 °C, 400 ppm of HCl, and 24 h for LA formation (34 % selectivity; 0.12 mol L−1). This new approach is also relevant because of significant changes to the mechanism for humins formation. All results are successfully fitted to a kinetic model simultaneously considering both catalytic mechanisms.

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Section: Introductionsupporting

confidence: 53%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Aqueous‐Phase Transformation of Glucose into Hydroxymethylfurfural and Levulinic Acid by Combining Homogeneous and Heterogeneous Catalysis

Garcés¹,

Faba²,

Dı́az³

et al. 2019

ChemSusChem

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“…This assumption is based on literature evidence for kinetic studies using glucose 8 only and recent studies by Woodley et al for fructose–glucose mixtures in water–acetone as the solvent. 37 In the latter, the reaction of glucose to HMF was required to obtain a better model description of the experimental data.…”

Section: Resultsmentioning

confidence: 99%

“…Recently, Woodley et al published a kinetic study on the conversion of glucose–fructose mixtures using HCl as the catalyst in an acetone–water mixture. 37 Kinetic studies are of prime importance for a proper design of the reactor section of LA processes and also allow selection of the best operating conditions to achieve maximum yields and volumetric production rates of LA.…”

Section: Introductionmentioning

confidence: 99%

Experimental and Kinetic Modeling Studies on the Conversion of Sucrose to Levulinic Acid and 5-Hydroxymethylfurfural Using Sulfuric Acid in Water

Soetedjo

Bovenkamp

Abdilla

et al. 2017

Ind. Eng. Chem. Res.

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We here report experimental and kinetic modeling studies on the conversion of sucrose to levulinic acid (LA) and 5-hydroxymethylfurfural (HMF) in water using sulfuric acid as the catalyst. Both compounds are versatile building blocks for the synthesis of various biobased (bulk) chemicals. A total of 24 experiments were performed in a temperature window of 80–180 °C, a sulfuric acid concentration between 0.005 and 0.5 M, and an initial sucrose concentration between 0.05 and 0.5 M. Glucose, fructose, and HMF were detected as the intermediate products. The maximum LA yield was 61 mol %, obtained at 160 °C, an initial sucrose concentration of 0.05 M, and an acid concentration of 0.2 M. The maximum HMF yield (22 mol %) was found for an acid concentration of 0.05 M, an initial sucrose concentration of 0.05 M, and a temperature of 140 °C. The experimental data were modeled using a number of possible reaction networks. The best model was obtained when using a first order approach in substrates (except for the reversion of glucose) and agreement between experiment and model was satisfactorily. The implication of the model regarding batch optimization is also discussed.

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Wood Adhesives Based on Natural Resources: A Critical Review: Part II. Carbohydrate‐Based Adhesives

Dunky¹

2021

Progress in Adhesion and Adhesives

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Synthesis of 5-hydroxymethylfurfural (HMF) by acid catalyzed dehydration of glucose–fructose mixtures

Cited by 120 publications

References 43 publications

Aqueous‐Phase Transformation of Glucose into Hydroxymethylfurfural and Levulinic Acid by Combining Homogeneous and Heterogeneous Catalysis

Aqueous‐Phase Transformation of Glucose into Hydroxymethylfurfural and Levulinic Acid by Combining Homogeneous and Heterogeneous Catalysis

Experimental and Kinetic Modeling Studies on the Conversion of Sucrose to Levulinic Acid and 5-Hydroxymethylfurfural Using Sulfuric Acid in Water

Wood Adhesives Based on Natural Resources: A Critical Review: Part II. Carbohydrate‐Based Adhesives

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