Selective fructose dehydration to 5-hydroxymethylfurfural from a fructose-glucose mixture over a sulfuric acid catalyst in a biphasic system: Experimental study and kinetic modelling

Guo, Wenze; Zheng, Zhaoke; Hacking, Jasper; Heeres, Hero J.; Yue, Jun

doi:10.1016/j.cej.2020.128182

Cited by 88 publications

(94 citation statements)

References 76 publications

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“…At 0.5 h, lower conversion (46%) and yield (47%) were observed. Further prolonging the reaction to 2 h, HMF yield was improved to 85%, but decreased to 63% at 2.5 h ( Figure 5 b), possibly because of humin formation from fructose decomposition [ 33 , 34 ]. Thus, the controlled experiments suggest that 160 °C/2 h is the most suitable condition to achieve the highest HMF yield over PorPOPS.…”

Section: Discussionmentioning

confidence: 99%

Mesoporous Porphyrin-Silica Nanocomposite as Solid Acid Catalyst for High Yield Synthesis of HMF in Water

et al. 2021

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Solid acid catalysts occupy a special class in heterogeneous catalysis for their efficiency in eco-friendly conversion of biomass into demanding chemicals. We synthesized porphyrin containing porous organic polymers (PorPOPs) using colloidal silica as a support. Post-modification with chlorosulfonic acid enabled sulfonic acid functionalization, and the resulting material (PorPOPS) showed excellent activity and durability for the conversion of fructose to 5-hydroxymethyl furfural (HMF) in green solvent water. PorPOPS composite was characterized by N2 sorption, FTIR, TGA, CHNS, FESEM, TEM and XPS techniques, justifying the successful synthesis of organic networks and the grafting of sulfonic acid sites (5 wt%). Furthermore, a high surface area (260 m2/g) and the presence of distinct mesopores of ~15 nm were distinctly different from the porphyrin containing sulfonated porous organic polymer (FePOP-1S). Surprisingly the hybrid PorPOPS showed an excellent yield of HMF (85%) and high selectivity (>90%) in water as compared to microporous pristine-FePOP-1S (yield of HMF = 35%). This research demonstrates the requirement of organic modification on silica surfaces to tailor the activity and selectivity of the catalysts. We foresee that this research may inspire further applications of biomass conversion in water in future environmental research.

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Section: Discussionmentioning

confidence: 99%

Mesoporous Porphyrin-Silica Nanocomposite as Solid Acid Catalyst for High Yield Synthesis of HMF in Water

et al. 2021

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“…Proving the highest conversion, fructose has been selected as the best sugar in its production through dehydration in an acid-catalyzed reacting medium (positive on "Reduce Derivatives"). 28,118 Production of HMF from glucose or fructose-glucose mixture is also the subject of various studies; [119][120][121] all of them agree on the significant catalytic complexity of the process (negative on " Catalysis"). Glucose is transformed into HMF through a first isomerization to fructose, then converted in a five-membered ring conformation (fructofuranose) and then undergone a series of three sequential dehydration to HMF, 122 requiring the presence of two different acid-catalytic activities: Lewis acidity for the isomerization and Brønsted acidity for the dehydration.…”

Section: Production From Precursors: 5-hmf Furfural and Derivatesmentioning

confidence: 99%

“…Glucose is transformed into HMF through a first isomerization to fructose, then converted in a five-membered ring conformation (fructofuranose) and then undergone a series of three sequential dehydration to HMF, 122 requiring the presence of two different acid-catalytic activities: Lewis acidity for the isomerization and Brønsted acidity for the dehydration. Thus, fructose is typically privileged for better yields and lower process complexity (positive on "Less Hazardous Chemical Syntheses"), but, on the other hand, glucose is an attractive precursor due to its higher availability and lower cost 119,123 (better on "Design for Energy Efficiency"). Mineral acids, metal salts, and various solid acids have been employed over these years, emphasizing the most excellent efficiency of Brønstedtype catalysts (H2SO4, zeolites, ion exchange resins, etc.)…”

Section: Production From Precursors: 5-hmf Furfural and Derivatesmentioning

confidence: 99%

Production of levulinic acid and alkyl levulinates: a process insight

et al. 2022

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“…According to early investigations of homogeneous acid catalysis [75] that reaction order is commonly assumed in the literature. An order range between 0.8 and 1.35 was derived from the analysis in acid fructose decomposition system to HMF and subsequent products (levulinic and formic acid) [76] . Figure A3 in the SI shows a constant initial rate constant without deviations by subsequent reactions for 40 % fructose solution at 60 °C.…”

Section: Resultsmentioning

confidence: 99%

Hydrolysis of Sucrose over Sulfonic Acid Resins

2021

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Sucrose hydrolysis on acidic ion‐exchange resins is a long‐established process in the sugar industry, but the formation of side products is less understood. A resin typically used in the industrial process (C124SH, Purolite) was investigated in a broad range of sucrose concentration (7 to 75 % w/w) and temperatures from 25 to 80 °C. Fructose is converted to 5‐hydroxymethylfurfural (HMF) due to a 1/2 order reaction. This is explained by the formation of a fructose disaccharide (monoanhydride) as an intermediate decomposing to HMF and fructose. Difructose dianhydrides (DFAs) are separately formed as prevailing by‐products. The color of the product mixture is correlated to HMF and found to be reduced by size exclusion inside the resins. Diffusional limitations of the total reaction are investigated by comparison of the entire resin bead with its size‐reduced forms obtained by milling. Without diffusion limitation the catalytic activity increases with the sugar concentration while the diffusion control leads to a maximal activity around 40 % w/w sugar. Diffusion coefficients of sucrose are calculated.

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Selective fructose dehydration to 5-hydroxymethylfurfural from a fructose-glucose mixture over a sulfuric acid catalyst in a biphasic system: Experimental study and kinetic modelling

Cited by 88 publications

References 76 publications

Mesoporous Porphyrin-Silica Nanocomposite as Solid Acid Catalyst for High Yield Synthesis of HMF in Water

Mesoporous Porphyrin-Silica Nanocomposite as Solid Acid Catalyst for High Yield Synthesis of HMF in Water

Production of levulinic acid and alkyl levulinates: a process insight

Hydrolysis of Sucrose over Sulfonic Acid Resins

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