Isomerization of d-glucose into d-fructose with a heterogeneous catalyst in organic solvents

Despax, Solenne; Estrine, Boris; Hoffmann, Norbert; Bras, Jean Le; Marinković, Siniša; Мuzart, Jacques

doi:10.1016/j.catcom.2013.05.004

Cited by 64 publications

(57 citation statements)

References 27 publications

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“…On the other hand, the formation of organic acids and mannose seem to be favored in the presence of the organic solvents. The results obtained are in accordance with those previously reported by Despax et al., but glucose conversion and product yields are higher, which is probably due to the higher temperature employed in our study. Amongst the various solvents tested, sulfolane, an industrial solvent with various applications, appears to be the most favorable especially in its mixture with H 2 O as the obtained fructose yield is comparable to that in neat water.…”

Section: Resultssupporting

confidence: 94%

“…The increased selectivity towards fructose is attributed to the higher rate of fructose–aluminate complex formation compared with other sugars. The formation of relatively low amounts of mannose in our experiments, in accordance with the results presented previously by Despax et al., is probably taking place by the same mechanism through the formation of the corresponding mannose complexes but at a significantly lower rate.…”

Section: Resultssupporting

confidence: 93%

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Glucose to Fructose Isomerization in Aqueous Media over Homogeneous and Heterogeneous Catalysts

et al. 2016

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Isomerization of glucose to fructose is an important reaction with numerous applications in terms of biomass valorization. The reaction is catalyzed enzymatically but may also proceed under alkaline conditions, in which case it is accompanied by low selectivity and formation of byproducts. Solid Lewis acid and basic catalytic materials are being studied as alternative catalysts. In this work, the isomerization of glucose to fructose in aqueous media over homogeneous and heterogeneous catalysts has been investigated. The effect of polar aprotic solvents and their mixtures with water on glucose conversion and fructose selectivity was also studied. Sodium aluminate (NaAlO2) has been proven to be very effective, resulting in high fructose yield (52.1 %) and high selectivity (84.8 %). Among the various solid catalysts tested, MgO afforded glucose conversion of 44 %, with 75.8 % and 33.4 % fructose selectivity and yield, respectively, when the isomerization reaction was conducted in neat H2O.

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Section: Resultssupporting

confidence: 94%

Section: Resultssupporting

confidence: 93%

Glucose to Fructose Isomerization in Aqueous Media over Homogeneous and Heterogeneous Catalysts

et al. 2016

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“…[37] More recently,D espax et al revisited sodium aluminate as ac atalystf or glucose isomerization into fructose. [29] Fructose yields of 40 and 49 %a re reported for aqueous and organic solvents, respectively. The reason for the improved yield of fructose in the presence of complexing anionsh as been discussed in literature.…”

Section: Isomerization Over Basic Catalystsmentioning

confidence: 99%

“…[34,44] Therefore, isomerization is usually performed at temperatures not exceeding 110-120 8C. Owingt o good solubility,w ater is as olvent of choice for saccharides, thoughp olar organic solvents, such as DMF, [31, 32, 39b] DMSO, [29] DMSO/ethylene glycol, [29] and DMSO/propylene glycol, [29] have also been utilized. Interestingly,asolvent can potentially influence the kinetics of isomerization over as olid base, analogously to what was uncovered for glucose isomerization in the presence of NaOH.…”

Section: Isomerization Over Basic Catalystsmentioning

confidence: 99%

Catalytic Isomerization of Biomass‐Derived Aldoses: A Review

Delidovich

Palkovits

2016

ChemSusChem

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Invited for this month's cover are Irina Delidovich and Regina Palkovits from RWTH Aachen University. The mini‐installation of sugar cubes and granulated sugar with chemical equations of isomerization reactions written on it represents a renewable feedstock for producing a broad range of valuable products. Our Review summarizes recent advances on chemocatalytic isomerization. The Review itself is available at 10.1002/cssc.201501577.

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“…Other studies confirmed the role of fructose in the process of converting glucose to 5-HMF and investigated the mechanism [30][31][32].…”

Section: Metal Halide Catalyzed Glucose Conversion To 5-hmfmentioning

confidence: 88%

Differentiation of the Coordination Chemistry of Metal Chlorides in Catalytic Conversion of Glucose in Ionic Liquids

Zhang

2016

Green Chemistry and Sustainable Technology

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Catalytic aldose isomerization to ketose is an important reaction for the utilization of cellulosic biomass. However, a fundamental understanding and knowledge base involved in this reaction remains lacking in the literature. In this chapter, we provide a focused review of the most studied solvent-based catalytic system involving metal halides for glucose isomerization to fructose and further to 5-hydroxymethhylfurfral (5-HMF). Results from studies by different physical techniques are critically reviewed. A differentiation of the coordination chemistry of different metal chlorides obtained by various physical techniques is established to rationalize the drastically different catalytic pathways by the metal chloride catalysts. The performance of metal chloride catalysts for the isomerization of aldose to ketose is found to correlate with their coordination chemistry. Solvents play an important role in determining the coordination structures for the metal ions, which critically affect the catalysis of the metal chloride precursors. Undesired side products are related to the reaction pathways corresponding to the nature of the coordination of metal ions with different oxygen sources in the substrates and the products.

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Isomerization of d-glucose into d-fructose with a heterogeneous catalyst in organic solvents

Cited by 64 publications

References 27 publications

Glucose to Fructose Isomerization in Aqueous Media over Homogeneous and Heterogeneous Catalysts

Glucose to Fructose Isomerization in Aqueous Media over Homogeneous and Heterogeneous Catalysts

Catalytic Isomerization of Biomass‐Derived Aldoses: A Review

Differentiation of the Coordination Chemistry of Metal Chlorides in Catalytic Conversion of Glucose in Ionic Liquids

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