NaBr/DMSO‐Induced Synthesis of 2,5‐Diformylfuran from Fructose or 5‐(Hydroxymethyl)furfural

Laugel, Caroline; Estrine, Boris; Bras, Jean Le; Hoffmann, Norbert; Marinković, Siniša; Мuzart, Jacques

doi:10.1002/cctc.201400023

Cited by 64 publications

(60 citation statements)

References 19 publications

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“…The peak at 374 nm has a molar absorptivity of 1.254×10 4 m −1 cm −1 . In an attempt to intensify absorption, we oxidized CMF to 2,5‐diformylfuran (DFF) 14 in a single step by Kornblum reaction and condensed 14 directly with angelica lactone. Under mild conditions this led to a mono‐adduct of the angelica lactone nucleophile, giving derivative 15 , while under more forcing conditions, twofold reaction was observed, giving 16 as a red solid (Scheme ).…”

Section: Methodsmentioning

confidence: 99%

Butenolide Derivatives of Biobased Furans: Sustainable Synthetic Dyes

Mascal

Saska

et al. 2019

Angewandte Chemie

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The dye and pigment manufacturing industry is one of the most polluting in the world. Each year, over one million tons of petrochemical colorants are produced globally, the synthesis of which generates a large amount of waste. Naturally occurring, plant‐based dyes, on the other hand, are resource intensive to produce (land, water, energy), and are generally less effective as colorants. Between these two extremes would be synthetic dyes that are fully sourced from biomass‐derived intermediates. The present work describes the synthesis of such compounds, containing strong chromophores that lead to bright colors in the yellow to red region of the visible spectrum. The study was originally motivated by an early report of an unidentified halomethylfurfural derivative which resulted from hydrolysis in the presence of barium carbonate, now characterized as a butenolide of 5‐(hydroxymethyl)furfural (HMF). The method has been generalized for the synthesis of dyes from other biobased platform molecules, and a mechanism is proposed.

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Section: Methodsmentioning

confidence: 99%

Butenolide Derivatives of Biobased Furans: Sustainable Synthetic Dyes

Mascal

Saska

et al. 2019

Angewandte Chemie

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“…CMF can be oxidized directly to the corresponding acid chloride by reaction with tert ‐butyl hypochlorite (route d), which forms spontaneously on mixing tert ‐butanol and commercial bleach . The acid chloride can be derivatized as shown in route e, and the primary chloride can be substituted as shown for example in route f. CMF can also be converted directly to 2,5‐diformylfuran (route g), which can be likewise oxidized to the diacid chloride of furan 2,5‐dicarboxylic acid (FDCA) (route h) . This diacid chloride, unlike FDCA, is freely soluble in common organic solvents and is a precursor to a range of FDCA derivatives (e.g.…”

Section: Methodsmentioning

confidence: 99%

5‐(Chloromethyl)furfural is the New HMF: Functionally Equivalent But More Practical in Terms of its Production From Biomass

Mascal

2015

ChemSusChem

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5-(Chloromethyl)furfural (CMF) is a disruptive innovation in the biorefinery. Chemically, it is at least as versatile as the well-known HMF but, unlike HMF, it is accessible in high yield directly from cellulosic biomass due to its lipophilicity and stability under acidic conditions, which facilitate isolation. It has a rich derivative chemistry that includes biofuels, renewable polymers, specialty chemicals, and value-added agrochemical and pharmaceutical products.

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“…There are several reports on the one‐pot transformation of carbohydrates into DFF from C6 carbohydrates in DMSO catalytic systems. Estrine and co‐workers were the first to report the one‐step conversion of fructose into DFF in DMSO without the use of a metal catalyst . This work is based on previous results indicating that the dehydration of fructose occurs in DMSO at high temperatures without a catalyst .…”

Section: Catalytic Conversion Of C6 Carbohydrates Into Chemicalsmentioning

confidence: 99%

One‐Pot Conversion of Carbohydrates into Furan Derivatives via Furfural and 5‐Hydroxylmethylfurfural as Intermediates

2016

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Recently, there has been growing interest in the transformation of renewable biomass into value-added fuels and chemicals. The catalytic conversion of naturally abundant carbohydrates can generate two-important furan chemicals: 5-hydroxymethylfurfural (HMF) from C6 carbohydrates and furfural from C5 carbohydrates. Both HMF and furfural have received great interest as precursors in the synthesis of commodity chemicals and liquid fuels. In recent years, a trend has emerged to integrate sequential catalytic processes involving multistep reactions for the direct one-pot transformation of carbohydrates into the aimed fuels and chemicals. One-pot reactions have remarkably unique and environmentally friendly benefits, including the fact that isolation and purification of intermediate compounds can be avoided. Herein, the present article aims to review recent advances in the one-pot conversion of carbohydrates into furan derivatives via furfural and HMF as intermediates. Special attention will be paid to the catalytic systems, mechanistic insight, reaction pathways, and catalyst stability. It is expected that this review will guide researchers to develop effective catalytic systems for the one-pot transformation of carbohydrates into furan derivatives.

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NaBr/DMSO‐Induced Synthesis of 2,5‐Diformylfuran from Fructose or 5‐(Hydroxymethyl)furfural

Cited by 64 publications

References 19 publications

Butenolide Derivatives of Biobased Furans: Sustainable Synthetic Dyes

Butenolide Derivatives of Biobased Furans: Sustainable Synthetic Dyes

5‐(Chloromethyl)furfural is the New HMF: Functionally Equivalent But More Practical in Terms of its Production From Biomass

One‐Pot Conversion of Carbohydrates into Furan Derivatives via Furfural and 5‐Hydroxylmethylfurfural as Intermediates

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