Bi (NO3)3·5H2O and cellulose mediated Cu-NPs — A highly efficient and novel catalytic system for aerobic oxidation of alcohols to carbonyls and synthesis of DFF from HMF

Baruah, Diganta; Hussain, Farhaz Liaquat; Suri, Mrinaly; Saikia, Ujwal Pratim; Sengupta, Pinaki; Dutta, Dipak Kumar; Konwar, Dilip

doi:10.1016/j.catcom.2016.01.003

Cited by 22 publications

(10 citation statements)

References 27 publications

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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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Section: Introductionmentioning

confidence: 99%

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

et al. 2017

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“…One-pot DFF synthesis from fructose under the catalysis of Cu-K-OMS-2 and a commercial catalyst Amberlyst 15 was studied. 3 . Cu-K-OMS-2-I, Cu-K-OMS-2-II, and Cu-K-OMS-2-III represent the catalysts prepared with different ratios of Cu to Mn in the catalysts as shown in Table 1.…”

Section: Catalystsmentioning

confidence: 99%

“…DFF can be produced by the oxidation of 5-hydroxymethylfurfural (HMF), and HMF can be produced from biomass resource [2]. Considering economy and sustainability, the aerobic oxidation approach to producing DFF from HMF is preferred [3], by using O 2 as oxidant. Developing heterogeneous catalysts has been paid more attention.…”

Section: Introductionmentioning

confidence: 99%

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A Non-Precious Metal Promoting the Synthesis of 5-Hydroxymethylfurfural

Zhao

Feng

et al. 2017

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Abstract:In this work, a new kind of catalyst was prepared for synthesis of 5-hydroxymethylfurfural. Copper ions were incorporated into manganese oxide octahedral molecular sieves (K-OMS-2). The catalysts Cu-K-OMS-2 were characterized by measuring FTIR spectra, scanning electron microscope images, X-ray diffraction patterns, and temperature-programmed desorption (TPD) and temperature-programmed reduction (TPR) profiles. Thermogravimetric analysis (TGA) demonstrated that the stability of Cu-K-OMS-2 is almost the same as that of K-OMS-2. XRD patterns showed that introducing copper ions did not change the structure of K-OMS-2, but copper ions had an effect on the morphology of K-OMS-2 as illustrated by SEM images. TPD profiles demonstrated that both K-OMS-2 and Cu-K-OMS-2 possess basic and acidic sites, and Cu-K-OMS-2 has weak acidic sites. One-pot synthesis of 2,5-diformylfuran (DFF) from fructose was investigated under the catalysis of Cu-K-OMS-2 together with a commercial catalyst Amberlyst 15. The effect of reaction time and temperature on the DFF yield was investigated, and reaction temperature had an effect on the DFF yield. The effect of atomic ratio of Cu to Mn of Cu-K-OMS-2 on the DFF yield was also investigated. The DFF yield was improved 34.7% by Cu-K-OMS-2 in comparison to K-OMS-2, indicating the promotion effect of copper on the DFF yield. Consecutive use of Cu-K-OMS-2 demonstrated that after 6 cycles, the loss of DFF yield was 6.3%, indicating a good reusability of Cu-K-OMS-2.

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“…10 Moreover, it has been shown that the reactivity of a nanomagnetic catalyst can be even better than a corresponding homogeneous catalyst. 11 For oxidation reactions, different metals like Fe, 12 Cu, 13 Co, 14 Bi, 15 and Au 16 have been used as a catalyst, but among them, palladium-based catalysts (both homogeneous and heterogeneous) have shown better activity. 17 For green and selective alcohol oxidation, different metals, oxidants, heterogeneous and homogeneous catalysts have been reported in literature up to now.…”

Section: Introductionmentioning

confidence: 99%

Green and selective oxidation of alcohols by immobilized Pd onto triazole functionalized $$\hbox {Fe}_{3}\hbox {O}_{4}$$ Fe 3 O 4

et al. 2018

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Carbonyl compounds were prepared by selective oxidation of alcohols in the presence of recoverable Fe 3 O 4 @SiO 2 @Pd magnetic nanocatalyst in aqueous media as a green solvent. Molecular oxygen served as an oxidant. The catalyst was removed from the reaction media by external magnetic field, washed with methanol, and reused for six more times without any considerable reduction in its reactivity. The chemoselectivity and regioselectivity of the catalyst can serve for selective oxidation of primary alcohols in the presence of secondary ones, and for oxidation of unhindered alcohols in the presence of hindered ones.

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Bi (NO3)3·5H2O and cellulose mediated Cu-NPs — A highly efficient and novel catalytic system for aerobic oxidation of alcohols to carbonyls and synthesis of DFF from HMF

Cited by 22 publications

References 27 publications

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

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

A Non-Precious Metal Promoting the Synthesis of 5-Hydroxymethylfurfural

Green and selective oxidation of alcohols by immobilized Pd onto triazole functionalized $$\hbox {Fe}_{3}\hbox {O}_{4}$$ Fe 3 O 4

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