The effect of solvent addition on fructose dehydration to 5-hydroxymethylfurfural in biphasic system over zeolites

“…This approach has been implemented many times in two-phase systems consisted of water and butanol ( Fig. 1) [13][14], tetrahydrofuran, acetonitryl, methylisobutylketon, and others [39][40][41][42][43].…”

Section: Resultsmentioning

confidence: 99%

The Nature and Mechanism of Selectivity Decrease of the Acid-catalyzed Fructose Conversion with Increasing the Carbohydrate Concentration

Chernyak¹,

Tarabanko²,

Смирнова³

et al. 2015

J. Sib. Fed. Univ. Chem.

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“…These results can be attributed to condensation reactions between HMF and sugar. Ordomsky et al (2012) also explained that an intensive interaction of the organic solvent with the catalyst was another major factor. In addition, using a large amount of organic solvent in the chemical process would increase production costs.…”

Section: Effect Of Volume Ratio Of Thf To H2omentioning

confidence: 99%

Catalysis of Glucose to 5-Hydroxymethylfurfural using Sn-Beta Zeolites and a Brønsted Acid in Biphasic Systems

Yang¹,

Wang²,

Lyu³

et al. 2015

BioResources

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Selective and efficient dehydration of glucose to 5-hydroxymethylfurfural (HMF) has been a widely explored concept recently, especially from the perspective of employing environmentally benign heterogeneous catalysts. However, there has been a relative paucity of data regarding the application of Sn-Beta zeolites, a category of catalysts that are very innocuous, inexpensive, and effective, toward evaluating bio-based conversions. Sn-Beta was shown to possess good Lewis acidity for catalyzing glucose isomerization to fructose in aqueous media at low pH and accelerating dehydration of glucose to HMF in a biphasic system with high yields. Sn-Beta zeolite with NH4F as the mineralizing agent (Sn-Beta-F) was a more effective catalyst for the selective dehydration of glucose to HMF. An optimal HMF yield of 53.0% was obtained over Sn-Beta-F zeolite in an acidic environment (pH 1) after 70 min at 190 °C. The reaction system was also effective for conversion of cellulose to HMF with a yield of 32.2% preliminarily.

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“…20,22 In this study, various catalysts were prepared by sulfation of different supports. These catalysts were SO 4 2 . The precipitate was washed with deionized water until the pH of the solution became 7.…”

Section: ■ Introductionmentioning

confidence: 99%

Fructose Dehydration to 5-Hydroxymethylfurfural over Sulfated TiO₂–SiO₂, Ti-SBA-15, ZrO₂, SiO₂, and Activated Carbon Catalysts

Kılıç

2015

Ind. Eng. Chem. Res.

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Different sulfated catalysts including SO 4 /TiO 2 −SiO 2 , SO 4 /Ti-SBA-15, SO 4 /ZrO 2 , SO 4 /AC, and SO 4 /SiO 2 were tested in fructose dehydration to 5-hydroxymethylfurfural (HMF). Reactions were carried out in dimethyl sulfoxide (DMSO) at 110°C. Characterization results indicated that no sulfur leaching was observed from SO 4 /ZrO 2 , SO 4 /TiO 2 −SiO 2 , and SO 4 /Ti-SBA-15 catalysts in the reaction tests. The SO 4 /TiO 2 −SiO 2 catalyst had a high amount of strong acid sites and the highest amount of Bronsted sites. The highest selectivity to HMF at high conversion, that is, 89% selectivity at 77% fructose conversion was obtained over this catalyst. It preserved its activity after four times reuse. ■ INTRODUCTIONDiminishing fossil fuel reserves and CO 2 emission problems force people to find alternative and sustainable resources to produce valuable chemicals. Production of these chemicals from biomass is an environmentally friendly process compared to a petroleum based process. 5-Hydroxymethylfurfural (HMF) is one of the key intermediates in order to convert the biomass to valuable chemicals such as polymers, biofuels, and bulk chemicals. 1 The most effective way of producing HMF is by carbohydrate conversion, especially dehydration of fructose.Fructose dehydration reaction occurs on the acid sites of the catalyst. Acid concentration, type of acid sites, and acid strength of the catalyst affect the product distribution significantly. 2−4 It is reported that fructose conversion to intermediates takes place on the Lewis sites, whereas Bronsted sites are responsible for the HMF formation from these intermediates. 5 Various acid catalysts including homogeneous (ionic liquids, mineral and organic acids) and heterogeneous types have been investigated. Because of the product contamination and recovery problems, heterogeneous catalysts are generally preferred. Wide ranges of heterogeneous catalysts (e.g., resins, metal sulfates, metal phosphates, heteropolyacids, zeolites, niobic acid based catalysts) have been tested. 3,6−15 However, no satisfactory yields have been achieved yet. Some of the catalysts have low stabilities due to leaching and some of them are not selective and promote side product formation such as formic acid and levulinic acid. Therefore, there are still studies pursued to find a stable, active, selective, and cheap heterogeneous catalyst for fructose dehydration to HMF.Sulfur ions and sulfate groups create Bronsted and strong acid sites when loaded on a support, such as iron oxide, alumina, titania, and zirconia. They were very active in fructose dehydration. 7,17 However, they leached during the reaction in different solvents. Solvent type also affects HMF yield. Different types of solvents from environmentally benign alcohols and water to the high-boiling-point polar aprotic solvents (dimethyl sulfoxide (DMSO) and dimethylamide (DMA)) have been investigated. High yields of HMF have been achieved by using high-boiling-point solvents such as DMSO and DMA. 9 Zirconia is known as ...

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The effect of solvent addition on fructose dehydration to 5-hydroxymethylfurfural in biphasic system over zeolites

Cited by 192 publications

References 32 publications

The Nature and Mechanism of Selectivity Decrease of the Acid-catalyzed Fructose Conversion with Increasing the Carbohydrate Concentration

The Nature and Mechanism of Selectivity Decrease of the Acid-catalyzed Fructose Conversion with Increasing the Carbohydrate Concentration

Catalysis of Glucose to 5-Hydroxymethylfurfural using Sn-Beta Zeolites and a Brønsted Acid in Biphasic Systems

Fructose Dehydration to 5-Hydroxymethylfurfural over Sulfated TiO₂–SiO₂, Ti-SBA-15, ZrO₂, SiO₂, and Activated Carbon Catalysts

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The effect of solvent addition on fructose dehydration to 5-hydroxymethylfurfural in biphasic system over zeolites

Cited by 192 publications

References 32 publications

The Nature and Mechanism of Selectivity Decrease of the Acid-catalyzed Fructose Conversion with Increasing the Carbohydrate Concentration

The Nature and Mechanism of Selectivity Decrease of the Acid-catalyzed Fructose Conversion with Increasing the Carbohydrate Concentration

Catalysis of Glucose to 5-Hydroxymethylfurfural using Sn-Beta Zeolites and a Brønsted Acid in Biphasic Systems

Fructose Dehydration to 5-Hydroxymethylfurfural over Sulfated TiO2–SiO2, Ti-SBA-15, ZrO2, SiO2, and Activated Carbon Catalysts

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Fructose Dehydration to 5-Hydroxymethylfurfural over Sulfated TiO₂–SiO₂, Ti-SBA-15, ZrO₂, SiO₂, and Activated Carbon Catalysts