One-Pot Synthesis of 2,5-Diformylfuran from Carbohydrate Derivatives by Sulfonated Resin and Hydrotalcite-Supported Ruthenium Catalysts

Takagaki, Atsushi; Takahashi, Miho; Nishimura, Shun; Ebitani, Kohki

doi:10.1021/cs200456t

Cited by 236 publications

(187 citation statements)

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“…The combination of solid acid and basic catalysts for the one-pot synthesis of furan derivatives from saccharides (mono and disaccharides) has also been reported as a very efficient way to valorize cellulosic biomass. [96][97][98][99][100] In this approach, the coexistence of acid and base without neutralization allows the production of HMF from glucose via a tandem-type reaction. First, the glucose undergoes isomerization into fructose catalyzed by a solid base and then, fructose is dehydrated into HMF by a solid acid (as presented in Fig.…”

Section: Conversion Of Cellulose and Hemicelullose Derivatives Into Pmentioning

confidence: 99%

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Recent advances on the utilization of layered double hydroxides (LDHs) and related heterogeneous catalysts in a lignocellulosic-feedstock biorefinery scheme

et al. 2017

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Layered double hydroxides (LDHs) and derived materials have been widely used as heterogeneous catalysts for different types of reactions either in gas or in liquid phase. Among these processes, the valorization/upgrading of lignocellulosic biomass and derived molecules have attracted enormous attention because it constitutes a pivotal axis in the transition from an economic model based on fossil resources to one based on renewable biomass resources with preference for biomass waste streams. Proof of this is the increasing amount of literature reports regarding the rational design and implementation of LDHs and related materials in catalytic processes such as: depolymerization, hydrogenation, selective oxidations, and C-C coupling reactions, among others, where biomass-derived compounds are used. The major aim of this contribution is to situate the most recent advances on the implementation of these types of catalysts into a lignocellulosic-feedstock biorefinery scheme, highlighting the versatility of LDHs and derived materials as multifunctional, tunable, cheap and easy to produce heterogeneous catalysts.

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Section: Conversion Of Cellulose and Hemicelullose Derivatives Into Pmentioning

confidence: 99%

“…In a more complex reaction system, a third heterogeneous catalyst (a hydrotalcite-supported ruthenium catalyst, Ru/HT) was implemented in order to drive the one-pot reaction to the selective oxidation of HMF into the corresponding dialdehyde, 2,5-diformylfuran (DFF) (a high-added value molecule), using glucose or fructose as saccharides 97 ( Fig. 8).…”

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confidence: 99%

Recent advances on the utilization of layered double hydroxides (LDHs) and related heterogeneous catalysts in a lignocellulosic-feedstock biorefinery scheme

et al. 2017

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“…6 A onepot catalytic process has been developed to remove the intermediate purification step in the multi-step syntheses. 6,8,9 However, the one-pot reaction generally requires a long reaction time extending to several tens of hours that often causes thermal degradation of the highly reactive furan ring molecules. 6,8 A set of catalysts in one pot could result in negative interference between catalysts, resulting in low efficiency of productivity.…”

Section: Introductionmentioning

confidence: 99%

One-flow syntheses of diverse heterocyclic furan chemicals directly from fructose via tandem transformation platform

et al. 2015

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The sustainable green chemistry associated with lignocellulosic biomass is of current interest for producing various chemical feedstocks via multi-step transformation processes. Here we introduce a chemical platform system for the multicomponent cascade transformation of natural lignocellulosic biomass resources. We demonstrate the concept by developing an integrated continuous two-step microfluidic system as a tandem transformation platform for direct conversion of fructose to diverse furan chemicals with excellent yields up to 99% via decarbonylation, etherification, oxidation and hydrogenolysis of a 5-hydroxymethylfurfural (HMF) intermediate. A sequential two-step process is utilized to complete the dehydration of fructose in the surface acid catalyst at 150°C for 6 min, which is followed by the four types of HMF conversion in a binary or ternary phase to produce furfuryl alcohol (94% yield), 5-ethoxymethylfurfural (99%), 2,5-diformylfuran (82%) and 2,5-dimethylfuran (90%) with magnetic-based heterogeneous catalysts at 70-150°C for 6-60 min. This innovative tandem microfluidic platform enables precise control of the reaction temperature and time for each individual biomass conversion step in a one-flow manner with no separation and purification steps for intermediates and catalysts.

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“…Biorefineries have gained much attention due to the potential to serve as a source of carbon-based fuels and chemicals in a carbon-neutral fashion, 13 the CO 2 released during energy conversion is consumed during subsequent biomass regrowth. Lignocellulosic biomass encompassing municipal and animal wastes, forestry residues, and others is a special interest resource on account of being the most abundant, inedible, and inexpensive biomass.…”

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confidence: 99%

One-Pot Synthesis of Furans from Various Saccharides Using a Combination of Solid Acid and Base Catalysts

Tuteja

Nishimura

Ebitani

2012

Bulletin of the Chemical Society of Japan

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One-pot synthesis of furans from various saccharides such as arabinose, rhamnose, and lactose were performed over solid acid and base catalysts. The combination of Amberlyst-15 and hydrotalcite catalysts showed successful activity for corresponding furans formation such as 2-furaldehyde (furfural), 5-hydroxymethyl-2-furaldehyde (HMF), and 5-methyl-2-furaldehyde (MF) via one-pot synthesis including isomerization and dehydration reactions. Moreover, the acidbase pair catalysts were also found to display excellent activity for the transformation from mixed-sources of sugars to furans. It was indicated that the isomerization of saccharides and successive dehydration in the one-pot synthesis of furans will be a great approach in a biorefinery.Biorefineries have gained much attention due to the potential to serve as a source of carbon-based fuels and chemicals in a carbon-neutral fashion, 13 the CO 2 released during energy conversion is consumed during subsequent biomass regrowth. Lignocellulosic biomass encompassing municipal and animal wastes, forestry residues, and others is a special interest resource on account of being the most abundant, inedible, and inexpensive biomass. The challenge for effective utilization is to develop cost-effective processes for transformation of huge built carbohydrates into value-added chemical compounds. Furan derivatives such as 2-furaldehyde (furfural), 5-hydroxymethyl-2-furaldehyde (HMF), and 5-methyl-2-furaldehyde (MF) have the potential to be substitutes of building blocks derived from petrochemicals in the production of fine chemicals, pharmaceuticals, and polymers. 48 For instance, HMF can be converted to 2,5-diformylfuran, 2,5-furandicarboxylic acid, 2,5-dimethylfuran, and levulinic acid. 4,913 MF is a useful intermediate for the production of agricultural chemicals (pesticides) and fragrances, and is a common flavoring component in the food industry and is considered a potential antitumor agent.1417 Industrial solvents like 1,5-pentanediol, 1,4-butanediol, and building blocks such as succinic acid, maleic acid are the main products derived from furfural. 1821Recently, Lam et al. 22 and Binder et al. 23 have reported the synthesis of furfural from xylose in good yield using Nafion 117 and chromium halide with ionic liquid, respectively. Dehydration of xylose to furfural is investigated using various solid acid catalysts like sulfonic acid appended porous silicas, 24 metal oxide nanosheets, 25 ion-exchange resins, 26 and zeolites. 27Besides, the inorganic acids with subcritical water at 403 K, 28 organic acids such as oxalic, levulinic, and p-toluenesulfonic acids 2932 were also examined for dehydration of D-fructose. From the view point of reaction system activation, dehydration in watermethyl isobutyl ketone or watertoluene biphasic systems were also investigated with H-mordenite and Hfaujasite by Moreau et al. 33 Although the yield obtained is significant in the above-mentioned processes most of them involve use of high temperature, severe reaction conditions, and difficu...

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One-Pot Synthesis of 2,5-Diformylfuran from Carbohydrate Derivatives by Sulfonated Resin and Hydrotalcite-Supported Ruthenium Catalysts

Cited by 236 publications

References 31 publications

Recent advances on the utilization of layered double hydroxides (LDHs) and related heterogeneous catalysts in a lignocellulosic-feedstock biorefinery scheme

Recent advances on the utilization of layered double hydroxides (LDHs) and related heterogeneous catalysts in a lignocellulosic-feedstock biorefinery scheme

One-flow syntheses of diverse heterocyclic furan chemicals directly from fructose via tandem transformation platform

One-Pot Synthesis of Furans from Various Saccharides Using a Combination of Solid Acid and Base Catalysts

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