Formation of 5-(Hydroxymethyl)furfural by Stepwise Dehydration over TiO<sub>2</sub> with Water-Tolerant Lewis Acid Sites

Noma, Ryouhei; Nakajima, Kiyotaka; Kamata, Keigo; Kitano, Masaaki; Hayashi, Shigenobu; Hara, Michikazu

doi:10.1021/acs.jpcc.5b03290

Cited by 85 publications

(88 citation statements)

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“…We have previously reported that the conversion of glucose and xylose to HMF and furfural over Lewis acid sites on Nb 2 O 5 and TiO 2 surfaces is based on step‐wise dehydration via the formation of dicarbonyl compounds typically represented by 3‐deoxyglucosone . In the case of glucose conversion, the Lewis acid sites facilitated the subsequent dehydration of 3‐deoxyglucosone to yield HMF as a main product.…”

Section: Resultsmentioning

confidence: 99%

“…It should be noted that the D-content of the resultant LA could be determined with 2 H NMR in Figure 7 and with the HPLC profile of the reaction mixture to be We have previously reported that the conversion of glucose and xylose to HMF and furfural over Lewis acid sites on Nb 2 O 5 and TiO 2 surfaces is based on step-wise dehydration via the formation of dicarbonyl compounds typically represented by 3deoxyglucosone. [49][50][51] In the case of glucose conversion, the Lewis acid sites facilitated the subsequent dehydration of 3deoxyglucosone to yield HMF as a main product. Although YNbO 4 also converted glucose to 3-deoxyglucosone in the first step, the retro-aldol reaction of 3-deoxyglucosone is more preferable than subsequent dehydration in the next step, which leads to the formation LA as a final product.…”

Section: Resultsmentioning

confidence: 99%

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Lewis Acid and Base Catalysis of YNbO₄ Toward Aqueous‐Phase Conversion of Hexose and Triose Sugars to Lactic Acid in Water

et al. 2019

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Amphoteric YNbO4 was synthesized by the simple coprecipitation using (NH4)3[Nb(O2)4] and Y(NO3)3, and examined as a new solid acid‐base bifunctional catalyst for various reactions including aqueous‐phase conversion of glucose to lactic acid. After drying the white precipitate at 353 K for 3 h, the resultant oxide is an amorphous YNbO4 with high densities of Lewis acid sites (0.18 mmol g−1) and base sites (0.38 mmol g−1). Negatively‐charged lattice oxygen of amorphous YNbO4 functioned as Lewis base sites that promote a Claisen‐Schmidt‐type condensation reaction with acetylacetone and benzaldehyde with comparable activity to reference catalysts. Amorphous YNbO4 can also be applicable to the production of lactic acid from glucose in water, which gives relatively high yields (19.6 %) compared with other reference catalysts. Mechanistic studies using glucose‐1‐d and 2H nuclear magnetic resonance spectroscopy (NMR) revealed that YNbO4 first converts glucose to two carbohydrates (glyceraldehyde and pyruvaldehyde) through dehydration via the formation of 3‐deoxyglucosone and subsequent retro‐aldolization, and these intermediates are then converted to lactic acid by both dehydration and isomerization through hydride transfer.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Lewis Acid and Base Catalysis of YNbO₄ Toward Aqueous‐Phase Conversion of Hexose and Triose Sugars to Lactic Acid in Water

et al. 2019

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“…Biodiesel synthesis and utilisation of glycerol are also important topics [75,76], though only one process has been industrialised for biodiesel production on ZnO-Al 2 O 3 catalysts. Note that the solid acids and bases applicable to biomass conversions should be water-tolerant catalysts [77,78].…”

Section: Biomass Transformation Reactionsmentioning

confidence: 99%

Heterogeneous Catalysis on Metal Oxides

2017

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This review article contains a reminder of the fundamentals of heterogeneous catalysis and a description of the main domains of heterogeneous catalysis and main families of metal oxide catalysts, which cover acid-base reactions, selective partial oxidation reactions, total oxidation reactions, depollution, biomass conversion, green chemistry and photocatalysis. Metal oxide catalysts are essential components in most refining and petrochemical processes. These catalysts are also critical to improving environmental quality. This paper attempts to review the major current industrial applications of supported and unsupported metal oxide catalysts. Viewpoints for understanding the catalysts' action are given, while applications and several case studies from academia and industry are given. Emphases are on catalyst description from synthesis to reaction conditions, on main industrial applications in the different domains and on views for the future, mainly regulated by environmental issues. Following a review of the major types of metal oxide catalysts and the processes that use these catalysts, this paper considers current and prospective major applications, where recent advances in the science of metal oxide catalysts have major economic and environmental impacts.

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“…These materials are abundant and cheap, and express water-tolerant Lewis acid sites and tunable acid-base properties with promising glucose-upgrading abilities [31,32]. Recently, we have shown that tungstite (WO 3 ·H 2 O) is also a viable contender [33].…”

Section: Introductionmentioning

confidence: 99%

Early Transition Metal Doped Tungstite as an Effective Catalyst for Glucose Upgrading to 5-Hydroxymethylfurfural

2018

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Glucose valorization to 5-hydroxymethylfurfural (HMF) remains challenging in the transition towards renewable chemistry. Lewis acidic tungstite is a viable, moderately active catalyst for glucose dehydration to HMF. Literature reports a multistep mechanism involving Lewis acid catalyzed isomerization to fructose, which is then dehydrated to HMF by Brønsted acid sites. Doping tungstite with titanium and niobium improves activity by optimizing the ratio between Lewis and Brønsted acid sites. Graphical AbstractKeywords Biomass · Glucose · 5-Hydroxymethylfurfural · Tungsten oxide · Doping

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Formation of 5-(Hydroxymethyl)furfural by Stepwise Dehydration over TiO₂ with Water-Tolerant Lewis Acid Sites

Cited by 85 publications

References 48 publications

Lewis Acid and Base Catalysis of YNbO₄ Toward Aqueous‐Phase Conversion of Hexose and Triose Sugars to Lactic Acid in Water

Lewis Acid and Base Catalysis of YNbO₄ Toward Aqueous‐Phase Conversion of Hexose and Triose Sugars to Lactic Acid in Water

Heterogeneous Catalysis on Metal Oxides

Early Transition Metal Doped Tungstite as an Effective Catalyst for Glucose Upgrading to 5-Hydroxymethylfurfural

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Formation of 5-(Hydroxymethyl)furfural by Stepwise Dehydration over TiO2 with Water-Tolerant Lewis Acid Sites

Cited by 85 publications

References 48 publications

Lewis Acid and Base Catalysis of YNbO4 Toward Aqueous‐Phase Conversion of Hexose and Triose Sugars to Lactic Acid in Water

Lewis Acid and Base Catalysis of YNbO4 Toward Aqueous‐Phase Conversion of Hexose and Triose Sugars to Lactic Acid in Water

Heterogeneous Catalysis on Metal Oxides

Early Transition Metal Doped Tungstite as an Effective Catalyst for Glucose Upgrading to 5-Hydroxymethylfurfural

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Formation of 5-(Hydroxymethyl)furfural by Stepwise Dehydration over TiO₂ with Water-Tolerant Lewis Acid Sites

Lewis Acid and Base Catalysis of YNbO₄ Toward Aqueous‐Phase Conversion of Hexose and Triose Sugars to Lactic Acid in Water

Lewis Acid and Base Catalysis of YNbO₄ Toward Aqueous‐Phase Conversion of Hexose and Triose Sugars to Lactic Acid in Water