Conversion of fructose into 5-hydroxymethylfurfural catalyzed by recyclable sulfonic acid-functionalized metal–organic frameworks

Chen, Jinzhu; Li, Kegui; Chen, Limin; Liu, Ruliang; Huang, Xing; Ye, Daiqi

doi:10.1039/c3gc42414f

Cited by 280 publications

(227 citation statements)

References 47 publications

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“…7c), resulting in the activation energy and pre-exponential factor of 43.6 kJ·mol -1 and 1.4×10 6 h -1 . The calculated activation energy was much lower than that reported by ) in acetone-water catalyzed by ion exchange resin Dowex 50wx8-10 ( Qi et al 2008), and slightly lower than that reported by ) in DMSO catalyzed by sulfonic acid-functionalized metal-organic framework (Chen et al 2014), indicating that SBC catalyst can effectively lower the activation energy and lead to a higher reaction rate.…”

Section: Kinetic Studymentioning

confidence: 49%

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Production of 5-Hydroxymethylfurfural from Fructose Catalyzed by Sulfonated Bamboo-Derived Carbon Prepared by Simultaneous Carbonization and Sulfonation

Shen

Chen

2016

BioResources

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A novel sulfonated bamboo-derived carbon (SBC) was prepared through a one-pot simultaneous carbonization and sulfonation method using ptoluenesulfonic acid as the sulfonating agent. This method was used in place of the two-step method of high temperature carbonization followed by sulfonation, in order to reduce energy consumption and avoid the use of substantial amounts of strong liquid acid. The as-prepared catalyst bearing SO3H, COOH, and phenolic OH groups demonstrated efficient catalytic activity in the dehydration of fructose to 5-hydroxymethylfurfural (HMF), achieving 92.1% HMF yield in a mixture of tetrahydrofuran (THF) and dimethylsulfoxiden (DMSO) (volume ratio of THF/DMSO 3/7). The mixture had a fructose concentration of 0.08 g·mL -1 with a catalyst amount of 10% weight of fructose at 140 °C in 60 min. No distinct activity drop was observed after the initial deactivation during 5 recycling runs, confirming a good stability of the prepared catalyst. Moreover, kinetic data showed that SBC promoted fructose dehydration to HMF may follow pseudo-first order kinetics with the activation energy of 43.6 kJ·mol -1 under investigated conditions. The convenient catalyst preparation method and excellent catalytic performance of the catalyst provide an easy-handling and ecofriendly strategy for crude biomass utilization in catalyst production.

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Section: Kinetic Studymentioning

confidence: 49%

“…According to ongoing studies, fructose dehydration to HMF obeys a pseudo-first order process (Chen et al 2014 …”

Section: Kinetic Studymentioning

confidence: 99%

Production of 5-Hydroxymethylfurfural from Fructose Catalyzed by Sulfonated Bamboo-Derived Carbon Prepared by Simultaneous Carbonization and Sulfonation

Shen

Chen

2016

BioResources

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“…Xu et al (2015a) also used the same catalyst in DMSO for HMF production with 79.6% HMF selectivity. Other catalysts such as FePO4 (Yang et al 2015b), Nb2O5 , graphite derivatives (Nie et al 2014), and sulfonic acidfunctionalized metal-organic frameworks MOF-SO3H (Chen et al 2014) have also been developed to produce HMF. In addition, a variety of biomass-derived carbonaceous solid acid materials have been demonstrated to be efficient for HMF production from fructose.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Conversion of Biomass-derived Carbohydrates into 5-Hydroxymethylfurfural using a Strong Solid Acid Catalyst in Aqueous γ-Valerolactone

Li¹,

Xu²,

Zhang³

et al. 2016

BioResources

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Selective conversion of biomass-derived carbohydrates into 5-hydroxymethylfurfural (HMF) is of great significance for biomass conversion. In this study, a novel solid Brønsted acid was prepared simply by the copolymerization of paraformaldehyde and p-toluenesulfonic acid and then used to catalyze the conversion of various carbohydrates into HMF in γ-valerolactone-water (GVL/H2O) reaction medium for the first time. The catalyst exhibited strong acidity, good water resistance, and high thermal stability. The present work focuses on the effects of various reaction parameters, including reaction temperature, time, water concentration, solvent, fructose level, and catalyst loading, on fructose dehydration. The catalyst exhibited excellent catalytic performance for HMF production from fructose in GVL and furnished a high HMF yield of 78.1% at 130 °C in 30 min. The recycling experiments suggested that the solid acid catalyst could be recycled at least seven times without a noticeable decrease in the catalytic activity. In addition, an attempt to study the one-step conversion of sucrose, glucose, and cellulose into HMF and furfural was performed using the same catalytic system.

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“…One is the filling of -SO 3 H groups in the pores that narrows the initially existing pores, in other words, the pore blockage contributes to the gradual disappearance of small pores. Another is the corrosion of the polymeric skeleton, especially in the presence of excessive chlorosulfonic acid, causing the decrease of mesopores [39]. An obvious evidence for the corrosion process is the formation of a large amount of macropores.…”

Section: Characterizationmentioning

confidence: 99%

Hypercrosslinked organic polymer based carbonaceous catalytic materials: Sulfonic acid functionality and nano-confinement effect

Wang

Chen

et al. 2015

Applied Catalysis B: Environmental

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Conversion of fructose into 5-hydroxymethylfurfural catalyzed by recyclable sulfonic acid-functionalized metal–organic frameworks

Abstract: Sulfonic acid-functionalized metal–organic frameworks are efficiently used as recyclable solid acid catalysts for the fructose-to-HMF transformation.

Cited by 280 publications

References 47 publications

Production of 5-Hydroxymethylfurfural from Fructose Catalyzed by Sulfonated Bamboo-Derived Carbon Prepared by Simultaneous Carbonization and Sulfonation

Production of 5-Hydroxymethylfurfural from Fructose Catalyzed by Sulfonated Bamboo-Derived Carbon Prepared by Simultaneous Carbonization and Sulfonation

Catalytic Conversion of Biomass-derived Carbohydrates into 5-Hydroxymethylfurfural using a Strong Solid Acid Catalyst in Aqueous γ-Valerolactone

Hypercrosslinked organic polymer based carbonaceous catalytic materials: Sulfonic acid functionality and nano-confinement effect

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