Mechanistic insights on catalytic conversion fructose to furfural on beta zeolite via selective carbon-carbon bond cleavage

Yang, Xiaohai; Zheng, Hongyan; Li, Xianqing; Zhu, Yulei; Li, Yongwang

doi:10.1016/j.mcat.2018.11.022

Cited by 41 publications

(27 citation statements)

References 50 publications

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“…FF is likely formed by the catalysis of Lewis acid sites for removing alcohol functional group in the course of LGO pyranose ring opening to form furan ring . A similar reaction pathway has been reported for the conversion of fructose to FF under catalysis of Lewis acid sites . In view of the low selectivity to side reactions, it seemed that the large pore size of Amberlyst 70 did not have predominant influence over the formation of DPs.…”

Section: Resultsmentioning

confidence: 56%

“…14 A similar reaction pathway has been reported for the conversion of fructose to FF under catalysis of Lewis acid sites. 44 In view of the low selectivity to side reactions, it seemed that the large pore size of Amberlyst 70 did not have predominant influence over the formation of DPs. In other words, the large pores allowed LGO and the products to enter and leave the catalyst matrix, and the dense Brønsted acid over the surface, formed by the high acid site amount (2.65 mmol/g) in a small area (S BET = 36 m 2 /g), contributed to the suppression of side reactions.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Clean Synthesis of 5-Hydroxymethylfurfural and Levulinic Acid by Aqueous Phase Conversion of Levoglucosenone over Solid Acid Catalysts

Huang

Kudo²,

Sperry

et al. 2019

ACS Sustainable Chem. Eng.

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Levoglucosenone (LGO) is an emerging biorenewable platform for the fine and commodity chemical industries. Herein, we report an aqueous phase conversion of LGO to 5-hydroxylmethylfurfural (HMF) and levulinic acid (LA) over solid acid catalyst. Several types of solid acid catalysts such as zeolites, strongly acidic ion-exchange resin, and sulfonated activated carbon were investigated for this reaction. Among the tested catalysts, ZSM-5 and Amberlyst 70 showed the best performances for selectively producing the target products, resulting in the highest total yield of HMF and LA at 72.2% on a molar basis. Factors decreasing the reaction selectivity were identified through the comparison of catalysts and kinetic analysis to the pore morphology, presence of Lewis acid sites, and formation of degradation products directly from LGO or its hydrated product. ZSM-5 and Amberlyst 70, after a single-batch experiment, contained deposits from the degradation products but could be reused with little loss in activity, although calcination was required for ZSM-5. The catalytic system, employing LGO as feedstock and recyclable solid acid catalysts, uses only water as reaction media and thus has the potential to be a clean route for producing the key building blocks HMF and LA.

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Section: Resultsmentioning

confidence: 56%

Section: ■ Results and Discussionmentioning

confidence: 99%

Clean Synthesis of 5-Hydroxymethylfurfural and Levulinic Acid by Aqueous Phase Conversion of Levoglucosenone over Solid Acid Catalysts

Huang

Kudo²,

Sperry

et al. 2019

ACS Sustainable Chem. Eng.

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show abstract

“…It is also presented in a small amount in the chicory reaction mixture. This can be explained by the reaction of fructose to furfural as a minor side reaction (Asakawa et al, 2019; Wang et al, 2019).…”

Section: Resultsmentioning

confidence: 99%

Continuous synthesis of 5‐hydroxymethylfurfural from biomass in on‐farm biorefinery

2022

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5‐hydroxymethylfurfural (HMF) is the object of extensive research in recent times. The challenge in the industrial production of HMF is the choice of cheap, hexose feedstock. This study compares continuous HMF synthesis from hexoses—fructose and glucose, and biomass—Miscanthus × giganteus and chicory roots. The experiments were conducted in technical‐scale biorefinery (TRL 6/7). In the first stage, optimal conditions for the production of HMF from hexoses were selected using sulfuric acid as a catalyst in an aqueous medium. The following conditions were chosen for fructose: temperature of 200°C, the reaction time of 18 min, and pH = 2, and for glucose: 210°C, 18 min, and pH = 3. Under these conditions, the HMF yield was 56.5 mol% (39.6 wt.%) from fructose and 18.1 mol% (12.6 wt.%) from glucose. From the biomass, the HMF yields were 36.7 and 16.2 wt.% for miscanthus and chicory roots, respectively. Some results from the conversion of biomass solutions are unexpected and show a need for further investigations. This work has demonstrated the capacity to produce HMF from biomass as part of an environmentally friendly process in a biorefinery. Further research in this field and process optimization will be a step forward in the sustainable production of bioplastics.

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“…Therefore, the fructose content of the product is of great importance for the HMF formation. The HMF formation from fructose is easier than glucose and is triggered at temperatures above 100°C (Cazor et al., 2006; Wang et al., 2019). In this study, the application of both processes at 108°C in the production of OPE and AC pekmez products increased the isomerization of glucose in this environment and caused an increase in the rate of HMF formation.…”

Section: Resultsmentioning

confidence: 99%

Sweet pomegranate pekmez production: Effect of different production methods and activated carbon treatment on some quality parameters and 5‐hydroxymethyl furfural formation

Altıok

Şen

Altıok

2021

Food Processing Preservation

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In the present study, “sweet pomegranate pekmez” (PP), was produced by three different methods as open pan evaporation (OPE), application of activated carbon prior to open pan evaporation (AC), and vacuum evaporation (VE). The effects of activated carbon treatment and production methods on pH, density, soluble solids, water activity, total phenolic content, HMF formation, mineral content, and texture characteristics were investigated. Textural properties of PP increased with increasing soluble solids content. HMF was not detected in AC and VE products. HMF content of OPE product was measured as 2.77 ± 0.28 mg.100 g. Activated carbon treatment resulted in significant reductions in mineral, HMF, and TPC contents of pekmez samples. HMF formation kinetics of PP was investigated at various accelerated storage temperatures. HMF formation was well described by the zero‐order reaction model among five kinetic models applied. The rate of reaction was determined as highly temperature‐dependent by an Arrhenius equation. Practical applications In recent years, consumer interest and demand for potentially health‐promoting products has motivated the production of such food products. In this context, in this study, sweet pomegranate pekmez is introduced as a potentially healthy product produced by different methods, and the production stages and conditions that may enlighten the industrial production of this traditional product are provided. In addition, the application of activated carbon used in the production of pekmez has been presented as an alternative method to reduce the potential formation of HMF during heat treatment.

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Mechanistic insights on catalytic conversion fructose to furfural on beta zeolite via selective carbon-carbon bond cleavage

Cited by 41 publications

References 50 publications

Clean Synthesis of 5-Hydroxymethylfurfural and Levulinic Acid by Aqueous Phase Conversion of Levoglucosenone over Solid Acid Catalysts

Clean Synthesis of 5-Hydroxymethylfurfural and Levulinic Acid by Aqueous Phase Conversion of Levoglucosenone over Solid Acid Catalysts

Continuous synthesis of 5‐hydroxymethylfurfural from biomass in on‐farm biorefinery

Sweet pomegranate pekmez production: Effect of different production methods and activated carbon treatment on some quality parameters and 5‐hydroxymethyl furfural formation

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