A process for efficient conversion of fructose into 5-hydroxymethylfurfural in ammonium salts

Cao, Qing; Guo, Xingcui; Guan, Jing; Mu, Xindong; Zhang, Dongke

doi:10.1016/j.apcata.2011.06.018

Cited by 57 publications

(45 citation statements)

References 37 publications

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“…When the initial fructose concentration was increased from 25 to 125 gL -1 the HMF conversion remained almost constant at 100%; however, the HMF yields decreased from 66 to 55%. This result is in agreement with reports in the literature that increasing the fructose concentration leads to higher rates of condensation reactions, with formation of larger amounts of humins (Rosatella et al, 2011;Roman-Leshkov et al, 2006;Cao et al, 2011). The option for working with 125 g L -1 of fructose in the further experiments was based on the greater productivity of a higher feed concentration for an industrial process, measured by the amount of HMF produced per unit reactor volume and thus a more favorable process economics (Cao et al, 2011).…”

Section: Effect Of Reaction Conditions Using Water/acetonesupporting

confidence: 80%

Production of 5-Hydroxymethylfurfural (Hmf) via Fructose Dehydration: Effect of Solvent and Salting-Out

Gomes

Pereira

Ribeiro

et al. 2015

Braz. J. Chem. Eng.

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-5-Hydroxymethylfurfural (HMF) is a key renewable platform compound for production of fuels and chemical intermediates. The production of 5-hydroxymethylfurfural (HMF) from fructose dehydration was studied using H 3 PO 4 as catalyst, in organic/water system with different solvents (acetone, 2-butanol and ethyl ether). The effect of fructose concentration, temperature and acid concentration was investigated in acetone/water medium. The increase in fructose concentration favors the formation of condensation products and rehydration products are favored at high acid concentration. The solvents exhibited similar performance when the volume ratio of organic to aqueous phase was 1:1, but when this ratio increases to 2:1, the HMF yield obtained with ether was much lower. NaCl addition to the aqueous phase promoted the extraction of HMF to the organic phase, with an HMF yield of 80% in the case of 2:1 acetone/water medium.

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Section: Effect Of Reaction Conditions Using Water/acetonesupporting

confidence: 80%

Production of 5-Hydroxymethylfurfural (Hmf) via Fructose Dehydration: Effect of Solvent and Salting-Out

Gomes

Pereira

Ribeiro

et al. 2015

Braz. J. Chem. Eng.

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“…1,5,7,[9][10][11][12][13][14][15][16][17][18][19][20][21] These methods have been widely investigated and many types of acid catalysts have been explored, such as mineral acid (such as HCl, H 2 SO 4 ), 3,5,11,22 organic acids (such as oxalic acid, citric acid, maleic acid, formic acid), 22,23 transition metal ions, 24,25 H-moredenites/ zeolites, 26 solid metal phosphates, 13,16 and strong acid cation exchanged resins. [17][18][19] As we know, homogenous acids are inexpensive and act as high activity for the acid-catalyzed dehydration reactions, but they have the drawbacks in terms of separation and recycling in addition to the equipment corrosion.…”

Section: Introductionmentioning

confidence: 99%

High yield production and purification of 5‐hydroxymethylfurfural

et al. 2013

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Conversion of carbohydrates to 5-hydroxymethylfurfural (HMF) will provide a new step toward achieving renewable biomass-based chemicals and fuels platform. Recently, the excellent yield of HMF (91.0%) in dimethyl sulfoxide (DMSO) catalyzed by sulfonated carbon was demonstrated, but the separation of HMF from the reaction mixture remains challenging because of the high boiling point of DMSO. As a solution, herein, low boiling point solvent tetrahydrofuran (THF) mixed with DMSO was used for the fructose dehydration and high yield of HMF (98.0%) was still obtained. Besides, the stability of the sulfonated carbonaceous catalyst was also confirmed. More importantly, HMF from the reaction solution was successfully separated by using simple extraction method, and high purity of HMF (ca. 96.4%) was obtained. Compared with pure DMSO solvent, the combination of low boiling point THF with DMSO not only gives higher yield of HMF, but also improves the separation efficiency and reduces environmental risk.

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“…The addition of a low boiling point solvent of THF into DMSO not only can increase the selectivity to HMF, but it also improves the separation efficiency (Wang et al 2013). On the one hand, in THF, fructose is very favorable to be converted into the furanoid form, which is much easier to generate HMF (West et al 2008;Zhu et al 2011;Wang et al 2013), and on the other hand, miscibility of THF with water can take the generated water away from liquid phase, preventing the side reactions due to the presence of water molecules (Chan and Zhang 2009;Cao et al 2011;Wang et al 2013). The influence of the volume ratio of THF/DMSO on fructose dehydration to HMF is shown in Table 2 (entries 4 to 8).…”

Section: Production Of Hmf From Fructosementioning

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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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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A process for efficient conversion of fructose into 5-hydroxymethylfurfural in ammonium salts

Cited by 57 publications

References 37 publications

Production of 5-Hydroxymethylfurfural (Hmf) via Fructose Dehydration: Effect of Solvent and Salting-Out

Production of 5-Hydroxymethylfurfural (Hmf) via Fructose Dehydration: Effect of Solvent and Salting-Out

High yield production and purification of 5‐hydroxymethylfurfural

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

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