Tin phosphate as a heterogeneous catalyst for efficient dehydration of glucose into 5-hydroxymethylfurfural in ionic liquid

Hou, Qidong; Zhen, Mengmeng; Liu, Le; Yu, C. X.; Huang, Fang; Zhang, Shiqiu; Li, Weizun; Mei, Ju

doi:10.1016/j.apcatb.2017.09.049

Cited by 162 publications

(91 citation statements)

References 82 publications

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“…Recently, HMF synthesis by sugar dehydration with ionic liquids (ILs) as solvents or using acidic ionic liquids [45][46][47] as catalysts has grown rapidly because of its unique and tunable properties. In fact, a 70% HMF yield with 1-ethyl-3-methylimidazolium chloride ([EMIM]Cl) as the reaction solvent can be obtained over a chromium (II) chloride catalyst [17]; a 83.4% HMF yield can be obtained over a chromium (II) chloride catalyst in 1,8-diazabicyclo [5.4.0]undec-7-ene-based ionic liquids [32]; a 48.4% HMF yield was observed over a germanium (IV) chloride catalyst in 1-butyl-3-methylimidazolium chloride ([BMIM]Cl) with glucose as the feedstock [34]; a 58.3% HMF yield can be obtained over a tin phosphate catalyst with the ionic liquid EMIMBr as the solvent [48]; a 67.3% HMF yield was reported over a 1-hydroxyethyl-3-methylimidazolium tetrafluoroborate ionic liquid catalyst in DMSO [38]. Only a 50.6% HMF yield with glucose as the feedstock was achieved in DMSO over the 1-carboxypropyl-3-methyl imidazoliumchloride ([CMIm]Cl) and ZrOCl 2 catalyst system by Hu et al, although a 95.7% HMF yield can be obtained with fructose as the feedstock over a [CMIm]Cl catalyst [16].…”

Section: Introductionmentioning

confidence: 99%

Selective Dehydration of Glucose into 5-Hydroxymethylfurfural by Ionic Liquid-ZrOCl2 in Isopropanol

Wang

et al. 2018

Catalysts

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In this work, a heterogeneous catalytic system consisting of [HO2CMMIm]Cl and ZrOCl2 in isopropanol is demonstrated to be effective for 5-hydroxymethylfurfural (HMF) synthesis with glucose as the feedstock. Various reaction conditions for HMF synthesis by glucose dehydration were investigated systematically. Under optimized reaction conditions, as high as 43 mol% HMF yield could be achieved. Increasing the water content to a level below 3.17% led to the production of HMF with a higher yield, while a lower HMF yield was observed when the water content was increased above 3.17%. In addition, the data also showed that ZrOCl2 could not only effectively convert glucose into intermediate species (which were not fructose, in contrast to the literature) but also catalyze the intermediate species’ in situ dehydration into HMF. [HO2CMMIm]Cl was used to catalyze the intermediate species’ in situ conversion to HMF. The kinetics data showed that a temperature increase accelerated the intermediate species’ dehydration reaction rate. The reaction of glucose dehydration was a strong endothermal reaction.

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Section: Introductionmentioning

confidence: 99%

Selective Dehydration of Glucose into 5-Hydroxymethylfurfural by Ionic Liquid-ZrOCl2 in Isopropanol

Wang

et al. 2018

Catalysts

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“…Solid acid catalysts, like sulfonate groups or phosphate-group-functionalized solid acids, are highly desirable from an economic and environmental point of view [19][20][21]. Catalysts possessing both Lewis/Brønsted acids sites exhibit bifunctional properties, and can be used for the one-pot synthesis of HMF from glucose [22][23][24]. Separation and purification of the intermediates is not necessary in the one-pot approach.…”

Section: -Hydroxymethylfurfural (Hmf)mentioning

confidence: 99%

“…Separation and purification of the intermediates is not necessary in the one-pot approach. Tin phosphate was prepared and used for converting glucose into HMF, and an HMF yield of 58.3% in the ionic liquid EMIMBr was obtained [22]. A polydivinylbenzene-based catalyst was used for the conversion of glucose to HMF, and HMF was obtained with stable yields [23].…”

Section: -Hydroxymethylfurfural (Hmf)mentioning

confidence: 99%

Sn-Based Porous Coordination Polymer Synthesized with Two Ligands for Tandem Catalysis Producing 5-Hydroxymethylfurfural

et al. 2019

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5-Hydroxymethylfurfural (HMF) is a biomass-derived important platform compound. Developing an efficient catalyst for producing HMF from a biomass source is important. Herein, using the ligands 5-sulfoisophthalic acid (SPA) and imidazole (Imd), a tin-based porous coordination polymer was synthesized, namely SPA-Imd-TinPCP. This novel material possesses a multifunctional catalysis capability. The coordinated tin (IV) can catalyze the isomerization of glucose to fructose. The ligand imidazole, as an additional base site, can catalyze glucose isomerization. The sulfonic group of the ligand SPA can catalyze the dehydration of fructose to HMF. SPA-Imd-TinPCP was used as a catalyst for the conversion of glucose to HMF. HMF yields of 59.5% in dimethyl sulfoxide (DMSO) and 49.8% in the biphasic solvent of water/tetrahydrofuran were obtained. Consecutive use of SPA-Imd-TinPCP demonstrated that, after reusing it five times, there was no significant activity loss in terms of the glucose conversion and HMF yield.Abstract: 5-Hydroxymethylfurfural (HMF) is a biomass-derived important platform compound. Developing an efficient catalyst for producing HMF from a biomass source is important. Herein, using the ligands 5-sulfoisophthalic acid (SPA) and imidazole (Imd), a tin-based porous coordination polymer was synthesized, namely SPA-Imd-TinPCP. This novel material possesses a multifunctional catalysis capability. The coordinated tin (IV) can catalyze the isomerization of glucose to fructose. The ligand imidazole, as an additional base site, can catalyze glucose isomerization. The sulfonic group of the ligand SPA can catalyze the dehydration of fructose to HMF. SPA-Imd-TinPCP was used as a catalyst for the conversion of glucose to HMF. HMF yields of 59.5% in dimethyl sulfoxide (DMSO) and 49.8% in the biphasic solvent of water/tetrahydrofuran were obtained. Consecutive use of SPA-Imd-TinPCP demonstrated that, after reusing it five times, there was no significant activity loss in terms of the glucose conversion and HMF yield.

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“…Hou et al. obtained a HMF yield of 58.30 % under the catalysis of tin phosphate . Unlike glucose, fructose can be efficiently converted to HMF with HMF yield as high as 90.00 %.…”

Section: Introductionmentioning

confidence: 99%

Isomerization Kinetics of Glucose to Fructose in Aqueous Solution with Magnesium‐Aluminum Hydrotalcites

Wang

Zhang

et al. 2020

ChemistrySelect

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Mg−Al hydrotalcites for catalyzing glucose isomerization to fructose are prepared. Effects of atom ratios of Mg/Al ranging from 1 to 4 and calcination temperatures from 250–650 °C on catalytic performance were examined systematically. It was found that the hydrotalcite (Mg2Al1LDH) calcined at 450 °C with an atom ratio of Mg/Al=2 is an excellent catalyst for glucose isomerization. Characterizations by SEM, EDS, TEM, XRD, FTIR, TG and BET demonstrated that the formed oxide condensed phase as well as the interaction with the alumina helps promote glucose isomerization reaction due to their appropriate basic sites at high calcination temperature. With Mg2Al1‐450 as the catalyst, kinetic model analysis confirmed that the reaction of glucose isomerization to fructose was an exothermal reversible reaction; both the forward and reverse reactions are quasi‐first‐order reactions with activation energies of 71.82 kJ/mol and 48.15 kJ/mol, respectively, while the side reaction is a zero‐order reaction with an activation energy of 94.22 kJ/mol. Therefore, high isomerization reaction temperature is not beneficial to enhance the yield and selectivity of fructose.

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Tin phosphate as a heterogeneous catalyst for efficient dehydration of glucose into 5-hydroxymethylfurfural in ionic liquid

Cited by 162 publications

References 82 publications

Selective Dehydration of Glucose into 5-Hydroxymethylfurfural by Ionic Liquid-ZrOCl2 in Isopropanol

Selective Dehydration of Glucose into 5-Hydroxymethylfurfural by Ionic Liquid-ZrOCl2 in Isopropanol

Sn-Based Porous Coordination Polymer Synthesized with Two Ligands for Tandem Catalysis Producing 5-Hydroxymethylfurfural

Isomerization Kinetics of Glucose to Fructose in Aqueous Solution with Magnesium‐Aluminum Hydrotalcites

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