Production of furans from C5 and C6 sugars in the presence of polar organic solvents
About: This article is published in Sustainable Energy and Fuels.The article was published on 2022-01-01 and is currently open access. It has received 15 citations till now. The article focuses on the topics: Polar & Reactivity (psychology).
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TL;DR: An efficient heterogeneous acid catalyst was prepared via the growth of a thiol-functionalized third-generation dendrimer on the surface of cellulose employing thiolene click chemistry, followed by the formation of sulfonic acid groups via the oxidation of thiol groups as discussed by the authors .
Abstract: An efficient heterogeneous acid catalyst was prepared via the growth of a thiol-functionalized third-generation dendrimer on the surface of cellulose employing thiol–ene click chemistry, followed by the formation of sulfonic acid groups via the oxidation of thiol groups.
14 citations
TL;DR: In this paper , a direct conversion reaction of glucose to 5-hydroxymethylfurfural (HMF) was studied using metal organic framework (MOF) as Lewisacid catalysts and a polyoxometalate (POM), silicotungstic acid, as a Brønsted type acid with a mixture of 1% glucose solution in γ-valerolactone (GVL)•10% H2O at 140 °C.
Abstract: The direct conversion reaction of glucose to 5‐hydroxymethylfurfural (HMF) is studied using metal organic framework (MOF) as Lewis‐acid catalysts and a polyoxometalate (POM), silicotungstic acid, as a Brønsted‐type acid with a mixture of 1% glucose solution in γ‐valerolactone (GVL)‐10% H2O at 140 °C. The study is carried out with two routes: one using MOF and POM tandem catalysts added independently and the other through the synthesis of a composite material denoted POM@MOF. The activity tests show that the profiles of the conversion and yield of HMF achieved in both routes are similar, with the reactions with MIL‐53(Al) and MIL‐101(Cr) catalysts producing the highest yield of HMF (40% after 8 h of reaction). Stability tests are performed on the POM@MOF catalysts based on MIL‐53(Al) and MIL‐101(Cr). MIL‐53(Al) and HSiW@MIL‐101(Cr) can be reused, showing a progressive loss in HMF yield due to the leaching of POM.
5 citations
TL;DR: In this paper , the degree of open structures (DOS) was determined by quantifying the formed carbonyl species by means of quantitative 19F NMR and potentiometric titration, and the progress of polymerization and ring opening were monitored by DSC and FT-IR spectroscopy.
Abstract: The chemistry of biomass-derived furans is particularly sensitive to ring openings. These side reactions occur during furfuryl alcohol polymerization. In this work, the furan ring-opening was controlled by changing polymerization conditions, such as varying the type of acidic initiator or the water content. The degree of open structures (DOS) was determined by quantifying the formed carbonyl species by means of quantitative 19F NMR and potentiometric titration. The progress of polymerization and ring opening were monitored by DSC and FT-IR spectroscopy. The presence of additional water is more determining on ring opening than the nature of the acidic initiator. Qualitative structural assessment by means of 13C NMR and FT-IR shows that, depending on the employed conditions, poly(furfuryl alcohol) samples can be classified in two groups. Indeed, either more ester or more ketone side groups are formed as a result of side ring opening reactions. The absence of additional water during FA polymerization preferentially leads to opened structures in the PFA bearing more ester moieties.
4 citations
TL;DR: In this paper , Schiff-based macromolecular architectures were used to generate tough and ductile materials via the creation of Schiff-Based macromolescular architectures for poly(furfuryl alcohol) polymers.
Abstract: Poly(furfuryl alcohol) is a bio-based thermoset resin with a limited application portfolio due to its brittleness. Side ring-opening reactions that occur during polymerization lead to carbonyl moieties. Such unique self-generated functionality was exploited to generate tough and ductile materials via the creation of Schiff-based macromolecular architectures.
3 citations
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TL;DR: A critical review of the effects of 5-hydroxymethylfurfural (HMF) on microorganisms and humans can be found in this paper, where the authors provide an overview of the effect of HMF on micro organisms and humans, HMF production and functional group transformations.
1,402 citations
TL;DR: A critical review of the literature on furfural, a promising, rich platform for lignocellulosic biofuels, presents new results and analysis in this area and highlights challenges and areas that need improvement.
Abstract: Furfural offers a promising, rich platform for lignocellulosic biofuels. These include methylfuran and methyltetrahydrofuran, valerate esters, ethylfurfuryl and ethyltetrahydrofurfuryl ethers as well as various C(10)-C(15) coupling products. The various production routes are critically reviewed, and the needs for improvements are identified. Their relative industrial potential is analysed by defining an investment index and CO(2) emissions as well as determining the fuel properties for the resulting products. Finally, the most promising candidate, 2-methylfuran, was subjected to a road trial of 90,000 km in a gasoline blend. Importantly, the potential of the furfural platform relies heavily on the cost-competitive production of furfural from lignocellulosic feedstock. Conventional standalone and emerging coproduct processes-for example, as a coproduct of cellulosic ethanol, levulinic acid or hydroxymethyl furfural-are expensive and energetically demanding. Challenges and areas that need improvement are highlighted. In addition to providing a critical review of the literature, this paper also presents new results and analysis in this area.
1,113 citations
TL;DR: A review of the most relevant chemical routes for converting furfural to chemicals, bio-fuels, and additives is presented in this article, focusing not only on industrially produced chemicals derived from fur, but also on other not yet commercialised products that have a high potential for commercialisation as commodities.
Abstract: The production of future transportation fuels and chemicals requires the deployment of new catalytic processes that transform biomass into valuable products under competitive conditions. Furfural has been identified as one of the most promising chemical platforms directly derived from biomass. With an annual production close to 300 kTon, furfural is currently a commodity chemical, and the technology for its production is largely established. The aim of this review is to discuss the most relevant chemical routes for converting furfural to chemicals, biofuels, and additives. This review focuses not only on industrially produced chemicals derived from furfural, but also on other not yet commercialised products that have a high potential for commercialisation as commodities. Other chemicals that are currently produced from oil but can also be derived from furfural are also reviewed. The chemical and engineering aspects such as the reaction conditions and mechanisms, as well as the main achievements and the challenges still to come in the pursuit of advancing the furfural-based industry, are highlighted.
1,079 citations
TL;DR: The acid-catalysed dehydration of hexoses results in the formation of 5-hydroxymethylfurfural (HMF) Fructose and inulin are especially good starting materials as discussed by the authors.
Abstract: The acid-catalysed dehydration of hexoses results in the formation of 5-hydroxymethylfurfural (HMF) Fructose and inulin are especially good starting materials A review is given of the many methods to produce HMF The reaction kinetics are dealt with in the sections: raw material, hydrolysis and reversion, catalysts, reaction temperature and time, the concentration and the risk of polymerization and the solvent and HMF stability Manufacturing processes are illustrated for fructose as the starting material: aqueous systems with homogeneous acid catalysis or those using ion-exchangers as catalyst, systems using dimethyl sulfoxide as the solvent and those using other organic solvents A short treatment is given on processes starting with glucose, work up procedures and the formation of levulinic acid and other in situ-formed HMF-derivatives
5-Hydroxymethylfurfural Ein Uberblick uber seine Herstellung
Die saurekatalysierte Dehydratisierung von Hexosen resultiert in der Bildung von 5%-Hydroxymethylfurfural (HMF) Fructose und Inulin sind besonders gute Ausgangsmaterialien Es wird ein Uberblick uber die zahlreichen Methoden zur Herstellung von HMF gegeben Die Reaktionskinetik ist eingeteilt in die Abschnitte “Rohmaterial, Hydrolyse und Reversion, Katalysatoren, Reaktionstemperatur und -zeit, Konzentration und das Risiko der Polymerisierung und das Losungsmittel und die Stabilitat” Die Herstellungsverfahren werden fur Fructose als Ausgangsmaterial illustriert: Wasrige Systeme mit homogener Saurekatalyse oder unter Verwendung von Ionenaustauschern als Katalysatoren, Systeme unter Verwendung von Dimethyl-sulfoxid als Losungsmittel und solche, die andere Losungsmittel verwenden Ein kurzer Hinweis wird auf Verfahren gegeben, die mit Glucose beginnen, Aufarbeitungsverfahren sowie auf die Bildung von Lavulinsaure und andere in situ gebildeten HMF-Derivaten
662 citations
TL;DR: In this paper, a tin-containing, high-silica molecular sieve with the zeolite beta topology (Sn-Beta) can efficiently catalyze the isomerization of glucose to fructose in aqueous media at low pH.
Abstract: Conversion of carbohydrates to 5-(hydroxymethyl)furfural (HMF) may provide a step forward toward achieving a renewable biomass-based chemicals and fuels platform. Recently, we reported that a tin-containing, high-silica molecular sieve with the zeolite beta topology (Sn-Beta) can efficiently catalyze the isomerization of glucose to fructose in aqueous media at low pH. Herein, we describe the combination of Sn-Beta with acid catalysts in a one vessel, biphasic reactor system to synthesize HMF from carbohydrates such as glucose, cellobiose, and starch with high efficiency. HMF selectivities over 70% were obtained using this “one-pot” biphasic water/tetrahydrofuran (THF) reactor system. The key to successfully achieving the conversions/selectivities reported is that Sn-Beta is able to convert glucose to fructose at pH near 1 and in saturated aqueous salt solutions.
604 citations