Iron-catalyzed selective oxidation of 5-hydroxylmethylfurfural in air: A facile synthesis of 2,5-diformylfuran at room temperature

Feng, Cheng; Dai, Jianjun; Xu, Hua‐Jian; Guo, Qi; Fu, Yao

doi:10.1016/j.cclet.2015.07.001

Cited by 28 publications

(11 citation statements)

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“…As often reported, Fe salts had been usually used as catalysts for the oxidation of hydroxyl to aldehyde group, and they performed well in selectivity. [30][31][32] In our experiments of oxidizing HMF to DFF in the presence of K 2 S 2 O 8 , Fe(NO 3 ) 3 gave a high selectivity of 99%, but the HMF conversion was only 46.8% (Table 1, entry 3). Inspired by its high selectivity, here we performed some experiments to screen co-catalysts for enhancing the HMF conversion ( Fig.…”

Section: Catalyst Screeningmentioning

confidence: 78%

An efficient approach to produce 2,5‐diformylfuran from 5‐hydroxymethylfurfural using air as oxidant

Jia

Liu

et al. 2019

J of Chemical Tech & Biotech

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BACKGROUND 2,5‐Diformylfuran (DFF) is a versatile bio‐derived platform chemical. Multiple catalytic systems including homogeneous and heterogeneous catalysts have been studied for the oxidation of 5‐hydroxymethylfurfural (HMF) to DFF, but a more efficient and economical approach to produce DFF via HMF remains to be developed. RESULTS This study provides a practical approach to oxidizing HMF to DFF using Fe(NO3)3/Cu(NO3)2 as catalysts and air as oxidant with the assistance of K2S2O8. The typical oxidation of HMF to DFF was conducted under conditions of 4 wt% catalyst, 80 °C and 3 h, achieving an excellent DFF yield of over 99%. CONCLUSION In this oxidation reaction, Fe(NO3)3 played a crucial catalytic role by the redox cycle of Fe(III) and Fe(II), while Cu(NO3)2 functioned as a co‐catalyst to promote the redox cycle of Fe(II) and Fe(III) by the redox cycle of Cu(II) and Cu(I) with the assistance of oxygen. Meanwhile, NO2 released from the decomposition of Fe(NO3)3 during the redox cycle of Fe(II) and Fe(III) also participated in the oxidation of Fe(II) to Fe(III) by the redox cycle of NO2 and NO with the assistance of oxygen. Noteworthily, K2S2O8 provided an essential acidity to the oxidation of HMF to DFF through its decomposition product SO3. All these factors together ensured the efficient conversion of HMF and high selectivity of DFF. © 2019 Society of Chemical Industry

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Section: Catalyst Screeningmentioning

confidence: 78%

An efficient approach to produce 2,5‐diformylfuran from 5‐hydroxymethylfurfural using air as oxidant

Jia

Liu

et al. 2019

J of Chemical Tech & Biotech

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“…Hansen et al 22 reported 95 % yield of DFF after 24 h, using CuCl and TEMPO by working at room temperature and ambient oxygen pressure in the presence of 3 nitrogen containing promoters. More recently Fang et al 23 showed that Fe(III) salts assisted by TEMPO catalyzed the selective oxidation of HMF into DFF in 1,2dichloroethane at room temperature and ambient oxygen pressure achieving 92 % yield of DFF after 4h. These catalytic systems based on Cu or Fe salts, in spite of their good performances in the HMF oxidation, they can not address the catalyst recyclability, therefore the development of a truly heterogeneous recyclable catalyst would be of interest for the green production of DFF from HMF.…”

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confidence: 99%

Polymers from biomass: one pot two-step synthesis of furilydenepropanenitrile derivatives with MIL-100(Fe) catalyst

Rapeyko

Arias

Climent

et al. 2017

Catal. Sci. Technol.

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“…It is used in the synthesis of fungicides, drugs, and polymeric materials [85]. Several promising catalytic routes for 2,5-DFF production are reported in the literature [85][86][87][88][89][90][91]. The complete transformation of 5-HMF with a 90% yield of 2,5-DFF was achieved with V 2 O 5 /TiO 2 catalyst in the presence of air and toluene or methyl isobutyl ketone (MIBK) as the solvent.…”

Section: -Hmf Derivativesmentioning

confidence: 99%

“…A 45% yield of 2,5-DFF was observed without recovering the 5-HMF intermediates. Researchers also disclosed the potential of iron as a cheap catalyst for the production of 2,5-DFF from 5-HMF [87,88]. Mittal et al [89] reported the use of magnetic bi-functional WO 3 HO-VO (salen)-SiO 2 @Fe 2 O 3 nano-catalyst to directly synthesize 2,5-DFF from fructose.…”

Section: -Hmf Derivativesmentioning

confidence: 99%

Bio-Based Chemicals from Renewable Biomass for Integrated Biorefineries

2019

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The production of chemicals from biomass, a renewable feedstock, is highly desirable in replacing petrochemicals to make biorefineries more economical. The best approach to compete with fossil-based refineries is the upgradation of biomass in integrated biorefineries. The integrated biorefineries employed various biomass feedstocks and conversion technologies to produce biofuels and bio-based chemicals. Bio-based chemicals can help to replace a large fraction of industrial chemicals and materials from fossil resources. Biomass-derived chemicals, such as 5-hydroxymethylfurfural (5-HMF), levulinic acid, furfurals, sugar alcohols, lactic acid, succinic acid, and phenols, are considered platform chemicals. These platform chemicals can be further used for the production of a variety of important chemicals on an industrial scale. However, current industrial production relies on relatively old and inefficient strategies and low production yields, which have decreased their competitiveness with fossil-based alternatives. The aim of the presented review is to provide a survey of past and current strategies used to achieve a sustainable conversion of biomass to platform chemicals. This review provides an overview of the chemicals obtained, based on the major components of lignocellulosic biomass, sugars, and lignin. First, important platform chemicals derived from the catalytic conversion of biomass were outlined. Later, the targeted chemicals that can be potentially manufactured from the starting or platform materials were discussed in detail. Despite significant advances, however, low yields, complex multistep synthesis processes, difficulties in purification, high costs, and the deactivation of catalysts are still hurdles for large-scale competitive biorefineries. These challenges could be overcome by single-step catalytic conversions using highly efficient and selective catalysts and exploring purification and separation technologies.

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Iron-catalyzed selective oxidation of 5-hydroxylmethylfurfural in air: A facile synthesis of 2,5-diformylfuran at room temperature

Cited by 28 publications

References 50 publications

An efficient approach to produce 2,5‐diformylfuran from 5‐hydroxymethylfurfural using air as oxidant

An efficient approach to produce 2,5‐diformylfuran from 5‐hydroxymethylfurfural using air as oxidant

Polymers from biomass: one pot two-step synthesis of furilydenepropanenitrile derivatives with MIL-100(Fe) catalyst

Bio-Based Chemicals from Renewable Biomass for Integrated Biorefineries

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