Ruthenium nanoparticles supported on N-containing mesoporous polymer catalyzed aerobic oxidation of biomass-derived 5-hydroxymethylfurfural (HMF) to 2,5-diformylfuran (DFF)

Ghosh, Koushik; Molla, Rostam Ali; Iqubal, Md. Asif; Islam, Sk. Manirul

doi:10.1016/j.apcata.2016.03.035

Cited by 64 publications

(32 citation statements)

References 69 publications

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“…Indeed, HMF can be transformed in different ways: the carbonyl group can be oxidized to the carboxylic moiety, producing 5-hydroxymethyl-2-furancarboxylic acid (HMFCA); the oxidation of the hydroxymethyl group can then produce FDCA via 5-formyl-2-furancaboxylic acid (FFCA) intermediate formation. Moreover, the formation of 2,5-diformylfuran (DFF) can also be observed, mainly in the absence of an added base and with metals other than Au [ 6 , 7 , 8 ].…”

Section: Introductionmentioning

confidence: 99%

Selective Oxidation of HMF via Catalytic and Photocatalytic Processes Using Metal-Supported Catalysts

et al. 2018

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In this study, 5-hydroxymethylfurfural (HMF) oxidation was carried out via both the catalytic and the photocatalytic approach. Special attention was devoted to the preparation of the TiO2-based catalysts, since this oxide has been widely used for catalytic and photocatalytic application in alcohol oxidation reactions. Thus, in the catalytic process, the colloidal heterocoagulation of very stable sols, followed by the spray-freeze-drying (SFD) approach, was successfully applied for the preparation of nanostructured porous TiO2-SiO2 mixed-oxides with high surface areas. The versatility of the process made it possible to encapsulate Pt particles and use this material in the liquid-phase oxidation of HMF. The photocatalytic activity of a commercial titania and a homemade oxide prepared with the microemulsion technique was then compared. The influence of gold, base addition, and oxygen content on product distribution in the photocatalytic process was evaluated.

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Section: Introductionmentioning

confidence: 99%

Selective Oxidation of HMF via Catalytic and Photocatalytic Processes Using Metal-Supported Catalysts

et al. 2018

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“…In general, DFF is prepared by the oxidation of HMF [ 8 , 11 ]. The selective oxidation of the hydroxyl group into the aldehyde has been achieved using a variety of different methodologies including homogeneous [ 8 , 11 , 15 , 16 ] and heterogeneous [ 8 , 11 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 ] metal catalysis, a one-step procedure from fructose (DMSO, NaBr (cat. ), 150 °C, 50%) [ 38 ], using molybdovanadophosphoric heteropolyacids [ 39 , 40 ], using polyaniline-grafted vanadyl acetylacetonate [ 41 ], metal free procedures [ 42 , 43 , 44 ] and enzyme catalysis [ 45 ].…”

Section: Introductionmentioning

confidence: 99%

Oxidation of 5-Chloromethylfurfural (CMF) to 2,5-Diformylfuran (DFF)

et al. 2017

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2,5-Diformylfuran (DFF) is an important biorenewable building block, namely for the manufacture of new polymers that may replace existing materials derived from limited fossil fuel resources. The current reported methods for the preparation of DFF are mainly derived from the oxidation of 5-hydroxymethylfurfural (HMF) and, to a lesser extent, directly from fructose. 5-Chloromethylfurfural (CMF) has been considered an alternative to HMF as an intermediate building block due to its advantages regarding stability, polarity, and availability from glucose and cellulose. The only reported method for the transformation of CMF to DFF is restricted to the use of DMSO as the solvent and oxidant. We envisioned that the transformation could be performed using more attractive conditions. To that end, we explored the oxidation of CMF to DFF by screening several oxidants such as H2O2, oxone, and pyridine N-oxide (PNO); different heating methods, namely thermal and microwave irradiation (MWI); and also flow conditions. The combination of PNO (4 equiv.) and Cu(OTf)2 (0.5 equiv.) in acetonitrile was identified as the best system, which lead to the formation of DFF in 54% yield under MWI for 5 min at 160 °C. Consequently, a range of different heterogeneous copper catalysts were tested, which allowed for catalyst reuse. Similar results were also observed under flow conditions using copper immobilized on silica under thermal heating at 160 °C for a residence time of 2.7 min. Finally, HMF and 5,5′-oxybis(5-methylene-2-furaldehyde) (OBMF) were the only byproducts identified under the reaction conditions studied.

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“…27 Ruthenium is a potential oxidizing metal; various ruthenium supported heterogeneous catalysts were used for HMF oxidation to 2,5-diformylfuran (DFF). [28][29][30][31] However, ruthenium supported materials were not successful for HMF oxidation to FDCA because complete oxidization to FDCA was impossible or ruthenium leaching caused the ruthenium to be unusable. 32,33 Recently, Ru/C commercial catalyst showed the base free oxidation of HMF to FDCA with an 88% FDCA yield using high catalyst loading.…”

Section: Introductionmentioning

confidence: 99%

Base-free oxidation of 5-hydroxymethyl-2-furfural to 2,5-furan dicarboxylic acid over basic metal oxide-supported ruthenium catalysts under aqueous conditions

et al. 2018

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Polyethylene terephthalate (PET) is the third-largest globally produced polymer, and many efforts have been made to replace PET with a renewable polymer. One renewable alternative to PET is polyethylene furanoate (PEF), which is prepared using 2,5-furan dicarboxylic acid (FDCA) as a precursor instead of terephthalic acid (TPA). Biomass-derived hydroxymethyl-2-furfural (HMF) can be converted to 2,5-furan dicarboxylic acid (FDCA) through multiple oxidation reactions. Metal oxide-supported Ru catalyst prepared by simple methods for the oxidation of 5-hydroxymethylfurfural (HMF) to 2,5-furan dicarboxylic acid (FDCA) in the absence of a base under aqueous conditions is reported. This study clearly explains that the nature of basicity of the support has an important role on the selective oxidation of HMF to FDCA. Among the various materials studied magnesium oxide (MgO)-supported Ru catalyst afforded a 100% HMF conversion and more than 90% FDCA yield with 90 psi of O 2 at 160 • C in 4 h and it could be used 5 times without a significant drop of FDCA yields.

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Ruthenium nanoparticles supported on N-containing mesoporous polymer catalyzed aerobic oxidation of biomass-derived 5-hydroxymethylfurfural (HMF) to 2,5-diformylfuran (DFF)

Cited by 64 publications

References 69 publications

Selective Oxidation of HMF via Catalytic and Photocatalytic Processes Using Metal-Supported Catalysts

Selective Oxidation of HMF via Catalytic and Photocatalytic Processes Using Metal-Supported Catalysts

Oxidation of 5-Chloromethylfurfural (CMF) to 2,5-Diformylfuran (DFF)

Base-free oxidation of 5-hydroxymethyl-2-furfural to 2,5-furan dicarboxylic acid over basic metal oxide-supported ruthenium catalysts under aqueous conditions

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