Recent advances in heterogeneous catalytic transfer hydrogenation/hydrogenolysis for valorization of biomass-derived furanic compounds

Fang, Wenting; Riisager, Anders

doi:10.1039/d0gc03931d

Cited by 145 publications

(85 citation statements)

References 171 publications

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“…The production of chemicals from a renewable resource is one of the essential tasks for sustainable chemistry ( Corma et al, 2007 ; Besson et al, 2014 ; Mika et al, 2017 ; Fang et al, 2020 ; Xu et al, 2020 ). As the 5-hydroxymethylfurfural (HMF) could be obtained easily by the dehydration of hexoses ( Yu and Tsang, 2017 ; Fan et al, 2019 ; Kang et al, 2019 ; Chang et al, 2021 ; Das and Mohanty, 2021 ; Guo et al, 2021 ; Tempelman et al, 2021 ), a class of compounds abundant in nature, the transformation of HMF is one of the hot topics for sustainable chemistry ( Averochkin et al, 2021 ; Bielski and Grynkiewicz, 2021 ; Fang and Riisager, 2021 ). Many studies had focused on the conversion of HMF to various products with potential or practice applications.…”

Section: Introductionmentioning

confidence: 99%

Tungsten Promoted Ni/Al2O3 as a Noble-Metal-Free Catalyst for the Conversion of 5-Hydroxymethylfurfural to 1-Hydroxy-2,5-Hexanedione

et al. 2022

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The conversion of 5-hydroxymethylfurfural (HMF) to 1-hydroxy-2,5-hexanedione (HHD) represented a typical route for high-value utilization of biomass. However, this reaction was often catalyzed by the noble metal catalyst. In this manuscript, W promoted Ni/Al2O3 was prepared as a noble-metal-free catalyst for this transformation. The catalysts were characterized by XRD, XPS, NH3-TPD, TEM, and EDS-mapping to study the influence of the introduction of W. There was an interaction between Ni and W, and strong acid sites were introduced by the addition of W. The W promoted Ni/Al2O3 showed good selectivity to HHD when used as a catalyst for the hydrogenation of HMF in water. The influences of the content of W, temperature, H2 pressure, reaction time, and acetic acid (AcOH) were studied. NiWOx/Al2O3-0.5 (mole ratio of W:Ni = 0.5) was found to be the most suitable catalyst. The high selectivity to HHD was ascribed to the acid sites introduced by W. This was proved by the fact that the selectivity to HHD was increased a lot when AcOH was added just using Ni/Al2O3 as catalysts. 59% yield of HHD was achieved on NiWOx/Al2O3-0.5 at 393 K, 4 MPa H2 reacting for 6 h, which was comparable to the noble metal catalyst, showing the potential application in the production of HHD from HMF.

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Section: Introductionmentioning

confidence: 99%

Tungsten Promoted Ni/Al2O3 as a Noble-Metal-Free Catalyst for the Conversion of 5-Hydroxymethylfurfural to 1-Hydroxy-2,5-Hexanedione

et al. 2022

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“…Furfural and 5-hydroxymethylfurfural (HMF) have received significant attention as promising platform chemicals due to their versatile utility in the synthesis of various commodity chemicals and fuels [1][2][3]. These platform chemicals can be easily transformed into value-added chemicals, such as 2-methylfuran, 2,5dimethylfuran, and other furans via chemical conversions or fermentation [4][5][6]. Since aromatic heterocycle furans are present in a variety of chiral natural products, pharmaceuticals, and other intermediates, a plethora of enantioselective methodologies has been developed for the synthetic community [7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Catalytic Enantioselective Reactions of Biomass-Derived Furans

Nam¹,

Yang²,

Ryu³

2022

Furan Derivatives - Recent Advances and Applications

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In this chapter, recent developments with regard to catalytic enantioselective reactions of furans, derived from biomass such as unsubstituted furan, 2-methylfuran, 2,5-dimethylfuran, and furfural are described. Although several review articles have dealt with the Diels-Alder reactions of furans, there have been no articles highlighting enantioselective versions. The resulting products derived from the catalytic enantioselective reaction of furan are often found as core structures in natural products and pharmaceuticals with important pharmacological activities. After recognizing the valuable skeleton of chiral furan derivatives, numerous attempts have been made to synthesize them by utilizing enantioselective cycloaddition reactions, Friedel-Crafts reactions, and nucleophilic addition reactions. Enantioselective cyclization reactions using furans as the 4π diene component provided chiral dihydrofuran derivatives. On the other hand, Friedel-Crafts and nucleophilic addition reactions served various furan derivatives with a chiral carbon atom in the α-position.

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“…As expected, the key role of biobased technologies is to replace the key existing products of oil-based refinement with renewables [ 4 , 6 , 7 ]. The tremendous synthetic potential explains the unprecedented scale of research in the fields of synthesis and application of furanic platform chemicals for the production of biofuels, chemicals, polymers and other industrially important products, which was evidenced by the increasing number of relevant publications (partially since 2010, Figure 1 ) and was highlighted in many recent reviews [ 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

Intermolecular Diels-Alder Cycloadditions of Furfural-Based Chemicals from Renewable Resources: A Focus on the Regio- and Diastereoselectivity in the Reaction with Alkenes

Galkin

Ananikov

2021

IJMS

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A recent strong trend toward green and sustainable chemistry has promoted the intensive use of renewable carbon sources for the production of polymers, biofuels, chemicals, monomers and other valuable products. The Diels-Alder reaction is of great importance in the chemistry of renewable resources and provides an atom-economic pathway for fine chemical synthesis and for the production of materials. The biobased furans furfural and 5-(hydroxymethyl)furfural, which can be easily obtained from the carbohydrate part of plant biomass, were recognized as “platform chemicals” that will help to replace the existing oil-based refining to biorefining. Diels-Alder cycloaddition of furanic dienes with various dienophiles represents the ideal example of a “green” process characterized by a 100% atom economy and a reasonable E-factor. In this review, we first summarize the literature data on the regio- and diastereoselectivity of intermolecular Diels-Alder reactions of furfural derivatives with alkenes with the aim of establishing the current progress in the efficient production of practically important low-molecular-weight products. The information provided here will be useful and relevant to scientists in many fields, including medical and pharmaceutical research, polymer development and materials science.

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Recent advances in heterogeneous catalytic transfer hydrogenation/hydrogenolysis for valorization of biomass-derived furanic compounds

Abstract: Catalytic transfer hydrogenation/hydrogenolysis can valorize renewable compounds derived from biomass. Different catalysts have the ability to transfer hydrogen from hydrogen-donor molecules thereby avoiding the use of hazardous gaseous hydrogen.

Cited by 145 publications

References 171 publications

Tungsten Promoted Ni/Al2O3 as a Noble-Metal-Free Catalyst for the Conversion of 5-Hydroxymethylfurfural to 1-Hydroxy-2,5-Hexanedione

Tungsten Promoted Ni/Al2O3 as a Noble-Metal-Free Catalyst for the Conversion of 5-Hydroxymethylfurfural to 1-Hydroxy-2,5-Hexanedione

Catalytic Enantioselective Reactions of Biomass-Derived Furans

Intermolecular Diels-Alder Cycloadditions of Furfural-Based Chemicals from Renewable Resources: A Focus on the Regio- and Diastereoselectivity in the Reaction with Alkenes

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