Ionic Liquid-Mediated Formation of 5-Hydroxymethylfurfural—A Promising Biomass-Derived Building Block

Zakrzewska, Małgorzata E.; Bogel‐Łukasik, Ewa; Bogel‐Łukasik, Rafał

doi:10.1021/cr100171a

Cited by 768 publications

(532 citation statements)

References 106 publications

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“…We speculate that the H 3 O þ ions, which are reversibly generated in hot water owing to the increased ionization constant of water at higher temperatures 23,24 , can catalyse the hydrolysis of the ball-milled cellulose to glucose. HMF can be formed by the dehydration of fructose 3,4,25 , which is an isomer of glucose. The presence of Pb(II) decreased the yields of glucose and HMF, and resulted in the formation of lactic acid ( Supplementary Fig.…”

Section: Resultsmentioning

confidence: 99%

Chemical synthesis of lactic acid from cellulose catalysed by lead(II) ions in water

et al. 2013

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The direct transformation of cellulose, which is the main component of lignocellulosic biomass, into building-block chemicals is the key to establishing biomass-based sustainable chemical processes. Only limited successes have been achieved for such transformations under mild conditions. Here we report the simple and efficient chemocatalytic conversion of cellulose in water in the presence of dilute lead(II) ions, into lactic acid, which is a high-value chemical used for the production of fine chemicals and biodegradable plastics. The lactic acid yield from microcrystalline cellulose and several lignocellulose-based raw biomasses is 460% at 463 K. Both theoretical and experimental studies suggest that lead(II) in combination with water catalyses a series of cascading steps for lactic acid formation, including the isomerization of glucose formed via the hydrolysis of cellulose into fructose, the selective cleavage of the C3-C4 bond of fructose to trioses and the selective conversion of trioses into lactic acid.

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Section: Resultsmentioning

confidence: 99%

Chemical synthesis of lactic acid from cellulose catalysed by lead(II) ions in water

et al. 2013

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“…The full solubilization of LS in [Bmim]Cl results in an acidic solution, which is anticipated to be potential reaction media for acid-catalyzed conversions. The dehydration of carbohydrate to produce valuable chemicals, such as HMF, is a typical acid-catalyzed process; [3] furthermore, the catalytic conversion of carbohydrate is attracting extensive attention because of the good solubility of carbohydrates in ILs and the unique properties of ILs for catalysis. [17] The first thought that comes to mind is whether LS is an effective catalyst for the dehydration of carbohydrates.…”

Section: Resultsmentioning

confidence: 99%

“…For example, 5-hydroxymethylfurfural (HMF) has been recognized as a versatile and key precursor for the production of fine chemicals, polymeric materials, and biofuels. [3] In recent years, the preparation of HMF through the dehydration of biomass-based sugars has received much attention, especially in ionic liquids (ILs), due to the good solubility of carbohydrates in ILs. [3] Since Zhao et al [4] reported that chromium(II) chloride could catalyze the dehydration of glucose into HMF in 1-ethyl-3-methylimidazolium chloride ([Emim]Cl) with a good yield, much effort has been devoted to developing more efficient and environmentally friendly processes for the conversion of cellulose and glucose into HMF.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Conversion of Inulin and Fructose into 5‐Hydroxymethylfurfural by Lignosulfonic Acid in Ionic Liquids

Xie¹,

Zhao²,

Wang³

2012

ChemSusChem

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In this work, we found that lignosulfonic acid (LS), which is a waste byproduct from the paper industry, in ionic liquids (ILs) can catalyze the dehydration of fructose and inulin into 5‐hydroxymethylfurfural (HMF) efficiently, which is a promising potential substitute for petroleum‐based building blocks. The effects of reaction time, temperature, catalyst loading, and reusability of the catalytic system were studied. It was found that a 94.3 % yield of HMF could be achieved in only 10 min at 100 °C under mild conditions. The reusability study of the LS–IL catalytic system after removal of HMF by ethyl acetate extraction demonstrated that the catalytic activity decreased from 77.4 to 62.9 % after five cycles and the catalytic activity could be recovered after simply removing the accumulated humins by filtration after adding ethanol to the LS–ILs. The integrated utilization of a biorenewable feedstock, catalyst, and ILs is an example of an ideal green chemical process.

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“…IL treatment of lignocellulosics and related compounds, with or without catalysts, is being increasingly studied, and various useful low-molecular-weight compounds have been produced (Zakrzewska et al 2010;Dashtban et al 2014;Ito et al 2016;Yokoyama and Miyafuji 2016). In previous studies, 5-HMF, furfural, and 2-hydroxyacetylfuran (2-HAF) (Fig.…”

Section: Introductionmentioning

confidence: 99%

Production of Furan Compounds from Cryptomeria japonica using Pyridinium Chloride under Various Conditions

et al. 2017

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was treated with pyridinium chloride ([Py]Cl)-water mixtures under various conditions to determine the optimum conditions for efficient production of furan compounds, such as 2-hydroxyacetylfuran (2-HAF), 5-hydroxymethylfurfural (5-HMF), and furfural. The maximum total yield of furan compounds, i.e., 9.24 wt.%, was obtained by the treatment of C. japonica with a 90% [Py]Cl and 10% water (w/w) solution for 30 min at 120 °C with a sample loading of 6 wt.%. The highest yield of 2-HAF from C. japonica was obtained by treatment for 3 min at 160 °C without the addition of water, although the total yield of furan compounds was lower than that obtained under the optimum treatment conditions. Scale-up of this process for efficient production of furan compounds from C. japonica was successfully performed under the optimum treatment conditions. In addition, the yields of 2-HAF and 5-HMF increased when ball-milled C. japonica containing low-crystallinity cellulose was treated under the optimum conditions.

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Ionic Liquid-Mediated Formation of 5-Hydroxymethylfurfural—A Promising Biomass-Derived Building Block

Cited by 768 publications

References 106 publications

Chemical synthesis of lactic acid from cellulose catalysed by lead(II) ions in water

Chemical synthesis of lactic acid from cellulose catalysed by lead(II) ions in water

Catalytic Conversion of Inulin and Fructose into 5‐Hydroxymethylfurfural by Lignosulfonic Acid in Ionic Liquids

Production of Furan Compounds from Cryptomeria japonica using Pyridinium Chloride under Various Conditions

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