Synthesis, chemistry and applications of 5-hydroxymethyl-furfural and its derivatives

Lewkowski, J.

doi:10.3998/ark.5550190.0002.102

Cited by 418 publications

(159 citation statements)

References 48 publications

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“…In 1901 Yoder et al [122] reportedly, employed concentrated sulfuric acid, instead of hydrobromic acid, and obtained similar results. However, recent reports [111] indicate that the conversion of HMF into 2,5-furandicarboxylic acid is a well-known synthesis route [114,[123][124][125]. Notwithstanding, the optimisation of these processes for the conversion of 2,5-FDCA into value-added chemicals and products has been dogged with challenges such as design optimisation as well as process integration [126].…”

Section: 5-furandicarboxylic Acid (Fdca)mentioning

confidence: 99%

Sustainable Chemicals: A Brief Survey of the Furans

et al. 2020

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Whether it is in the textiles, paints and coatings, energy sector, polymers, plastics, woods, sugar chemistry, pharmacy, aerospace and the automotive industries, the multiplicity of applications of furans and their derivatives, have made steady, impressive, and progressive impacts over the last 9 decades. After World War II, due to the shift in focus towards the petroleum-based chemical feedstocks, research, and development studies of these impressive class of lignocellulosic-derived chemicals, slowed down markedly. The trend, however, has reversed remarkably in recent time, due to the pursuit for "green" and sustainable chemical feedstocks, coupled with the increasing concerns over climate change, volatile oil prices and the attendant undesirable environmental issues, associated with fossil hydrocarbons. Chemicals obtained from "green" inedible lignocellulosic biomass, such as: the furans and their derivatives, ranks amongst the most promising, sustainable, and industrially applicable alternatives to various petroleum-derived chemicals; further offering an enormous assortment of unique compounds/materials, and properties analogous to and even exceeding those derived from fossil hydrocarbons. This article reviews selected progresses, so far made, in the field of furans and its derivatives and their application portfolios; while recognising the immense contributions of Peters and Dunlop, who in no small measures, advanced the furan chemical industry during their research efforts at the Oat Hull Research Centre at the Quaker Oats Company, Cedar Rapids, USA.

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Section: 5-furandicarboxylic Acid (Fdca)mentioning

confidence: 99%

Sustainable Chemicals: A Brief Survey of the Furans

et al. 2020

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“…We explained this finding by considering that under acidic conditions, 5-HMF can undergo dimerization forming 5,5′(oxy-bis(methylene))bis-2-furfural (Che et al, 2012; Galkin et al, 2016). Accordingly, the dimer can be converted back to 5-HMF simply by hydrolysis (Lewkowski, 2001). For this reason, we determined the yield in 5-HMF in both cases also after performing hydrolysis by adding 250 μL of water and stirring for 20 min prior to the spectroscopic determination.…”

Section: Resultsmentioning

confidence: 99%

Task-Specific Organic Salts and Ionic Liquids Binary Mixtures: A Combination to Obtain 5-Hydroxymethylfurfural From Carbohydrates

2019

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The increase in energy demand and depletion of fossil fuels are among major issues of modern society. Valorization and transformation of raw materials in products of industrial value represent a challenge. This justifies the growing interest of scientific research toward the identification of suitable media and methodologies able to pursue above goals, paying attention to matter of sustainability. On this subject, we studied sulfonic-acid functionalized diimidazolium salts as catalysts for the conversion of fructose and sucrose to 5-hydroxymethylfurfural (5-HMF) in an ionic liquid mixture. In general, using these salts allowed us to obtain 5-HMF in good yields from both substrates in mild conditions. Indeed, at 60°C and in the presence of 20 mol% of catalyst, 5-HMF yields of 60 and 30% were obtained from fructose and sucrose, respectively. The catalytic system was recycled and used up to six times observing no appreciable loss in yield for the first four cycles. Moreover, we gathered mechanistic information by in situ 1 H NMR monitoring the dehydration of fructose. To dissect the role of acidity on the reaction, we determined the Hammett acidity function of each salt. Comparison of these results with yields and reactivity observed in the presence of related monocationic salts and with a dicationic salt bearing only one sulfonic acid group, allowed stating that the reactivity observed is the result of the combined action of acidity and structural features of the catalysts. Overall, the approach proposed here could contribute to pave the way to increase sustainability in the raw material valorization processes.

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“…Scheme 2. Synthesis of FDCA from hexose derivates [9,14,15]. (a) Mucic acid route, (b) conjugated hexose route.…”

Section: Single Noble Metal Catalystsmentioning

confidence: 99%

“…5-hydroxymethylfurfural (HMF), a versatile intermediate dehydrated from abundant C 6 carbohydrates, can be converted to high valueadded chemicals (Scheme 1) by oxidation, hydrogenation, polymerization, and ring-opening reactions of its furan ring, aldehyde and alcohol groups [5,6]. For instance, the oxidation products of HMF comprise 2,5-diformylfuran (DFF), 5-hydroxymethyl-2-furan carboxylic acid (HMFCA), 5-formyl-2-furancarboxylic acid (FFCA) and 2,5-furandicarboxylic acid (FDCA), which could be widely used in fine chemicals, pharmacy, chiral catalysis, molecular recognition, and polymers [7][8][9][10]. Especially, as one of the top-12 valueadded platform chemicals from biomass listed by the U.S. Department of Energy, FDCA is able to make up of the terephthalic acid, a large-scale monomer of the commercial polyethylene terephthalate [4,[11][12][13].…”

Section: Introductionmentioning

confidence: 99%