Acid-Catalyzed Production of 5-Hydroxymethyl Furfural from <scp>d</scp>-Fructose in Subcritical Water

Asghari, Feridoun Salak; Yoshida, Hiroyuki

doi:10.1021/ie051088y

Cited by 463 publications

(328 citation statements)

References 45 publications

(112 reference statements)

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“…Dehydration of xylose to furfural is investigated using various solid acid catalysts like sulfonic acid appended porous silicas, 24 metal oxide nanosheets, 25 ion-exchange resins, 26 and zeolites. 27 Besides, the inorganic acids with subcritical water at 403 K, 28 organic acids such as oxalic, levulinic, and p-toluenesulfonic acids 2932 were also examined for dehydration of D-fructose. From the view point of reaction system activation, dehydration in watermethyl isobutyl ketone or watertoluene biphasic systems were also investigated with H-mordenite and Hfaujasite by Moreau et al 33 Although the yield obtained is significant in the above-mentioned processes most of them involve use of high temperature, severe reaction conditions, and difficulty in recovery and reusability of catalyst.…”

mentioning

confidence: 99%

One-Pot Synthesis of Furans from Various Saccharides Using a Combination of Solid Acid and Base Catalysts

Tuteja

Nishimura

Ebitani

2012

Bulletin of the Chemical Society of Japan

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One-pot synthesis of furans from various saccharides such as arabinose, rhamnose, and lactose were performed over solid acid and base catalysts. The combination of Amberlyst-15 and hydrotalcite catalysts showed successful activity for corresponding furans formation such as 2-furaldehyde (furfural), 5-hydroxymethyl-2-furaldehyde (HMF), and 5-methyl-2-furaldehyde (MF) via one-pot synthesis including isomerization and dehydration reactions. Moreover, the acidbase pair catalysts were also found to display excellent activity for the transformation from mixed-sources of sugars to furans. It was indicated that the isomerization of saccharides and successive dehydration in the one-pot synthesis of furans will be a great approach in a biorefinery.Biorefineries have gained much attention due to the potential to serve as a source of carbon-based fuels and chemicals in a carbon-neutral fashion, 13 the CO 2 released during energy conversion is consumed during subsequent biomass regrowth. Lignocellulosic biomass encompassing municipal and animal wastes, forestry residues, and others is a special interest resource on account of being the most abundant, inedible, and inexpensive biomass. The challenge for effective utilization is to develop cost-effective processes for transformation of huge built carbohydrates into value-added chemical compounds. Furan derivatives such as 2-furaldehyde (furfural), 5-hydroxymethyl-2-furaldehyde (HMF), and 5-methyl-2-furaldehyde (MF) have the potential to be substitutes of building blocks derived from petrochemicals in the production of fine chemicals, pharmaceuticals, and polymers. 48 For instance, HMF can be converted to 2,5-diformylfuran, 2,5-furandicarboxylic acid, 2,5-dimethylfuran, and levulinic acid. 4,913 MF is a useful intermediate for the production of agricultural chemicals (pesticides) and fragrances, and is a common flavoring component in the food industry and is considered a potential antitumor agent.1417 Industrial solvents like 1,5-pentanediol, 1,4-butanediol, and building blocks such as succinic acid, maleic acid are the main products derived from furfural. 1821Recently, Lam et al. 22 and Binder et al. 23 have reported the synthesis of furfural from xylose in good yield using Nafion 117 and chromium halide with ionic liquid, respectively. Dehydration of xylose to furfural is investigated using various solid acid catalysts like sulfonic acid appended porous silicas, 24 metal oxide nanosheets, 25 ion-exchange resins, 26 and zeolites. 27Besides, the inorganic acids with subcritical water at 403 K, 28 organic acids such as oxalic, levulinic, and p-toluenesulfonic acids 2932 were also examined for dehydration of D-fructose. From the view point of reaction system activation, dehydration in watermethyl isobutyl ketone or watertoluene biphasic systems were also investigated with H-mordenite and Hfaujasite by Moreau et al. 33 Although the yield obtained is significant in the above-mentioned processes most of them involve use of high temperature, severe reaction conditions, and difficu...

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mentioning

confidence: 99%

One-Pot Synthesis of Furans from Various Saccharides Using a Combination of Solid Acid and Base Catalysts

Tuteja

Nishimura

Ebitani

2012

Bulletin of the Chemical Society of Japan

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“…According to them, the use of a strong acid such as HCl accelerates the rehydration of HMF to levulinic and formic acids. High HMF selectivities were also obtained when using H 3 PO 4 in glucose dehydration performed in biphasic system (Chheda et al, 2007) and in fructose dehydration in subcritical water (Asghari and Yoshida, 2006).…”

Section: Effect Of Reaction Conditions Using Water/acetonementioning

confidence: 89%

Production of 5-Hydroxymethylfurfural (Hmf) via Fructose Dehydration: Effect of Solvent and Salting-Out

Gomes

Pereira

Ribeiro

et al. 2015

Braz. J. Chem. Eng.

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-5-Hydroxymethylfurfural (HMF) is a key renewable platform compound for production of fuels and chemical intermediates. The production of 5-hydroxymethylfurfural (HMF) from fructose dehydration was studied using H 3 PO 4 as catalyst, in organic/water system with different solvents (acetone, 2-butanol and ethyl ether). The effect of fructose concentration, temperature and acid concentration was investigated in acetone/water medium. The increase in fructose concentration favors the formation of condensation products and rehydration products are favored at high acid concentration. The solvents exhibited similar performance when the volume ratio of organic to aqueous phase was 1:1, but when this ratio increases to 2:1, the HMF yield obtained with ether was much lower. NaCl addition to the aqueous phase promoted the extraction of HMF to the organic phase, with an HMF yield of 80% in the case of 2:1 acetone/water medium.

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“…But due to the stability of cotton fiber structure and limited hydronium ions, only some cotton can give rise to monosaccharides, other parts of the chain form oligomers [24] [25]. Monosaccharides and oligomers reacted along different paths: (ⅰ) Glucose splitting into four-carbon sugar, phloroglucinol, furan, organic acids, aldehydes and so on [26] [27]. These substances formed soluble polymer by intermolecular dehydration and aromatization.…”

Section: Chemical Characteristics Of Hydrothermal Carbonization Productsmentioning

confidence: 99%

Evolution of Waster Cotton Fiber Hydro-Char Physicochemical Structure during Hydrothermal Carbonation

Shi¹,

Zhang²,

Zhang³

et al. 2017

Preprint

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Abstract：In order to study the hydrothermal behavior of cotton fiber, the carbonization process and structural evolution of discarded cotton fiber (WCF) under hydrothermal conditions were discussed use microcrystalline cellulose (MCC) and glucose as model compounds. The results showed that high temperature was beneficial to the hydrolysis of discarded cotton fiber, and the yield of the sugar was 4.5% which was lower than that of MCC 6.51%.WFC and MCC are carbonized in 240~260 ℃ and 220~240 ℃ respectively, while the carbonation temperature of glucose is lower than 220 ℃. The quality ratio of C/O in WCF and glucose hydrothermal products is 5.79 and 5.85 respectively; three kinds of hydrothermal carbonization products have similar crystal structure and oxygen-containing functional groups, and the WCF carbonization products contain a lot of irregular particles while the main products of glucose carbonization are 0.5 μm carbon microspheres (CMCC). The results show that glucose is an important intermediate product of WCF hydrolysis carbonation, and there are two main paths of cotton fiber hydrothermal carbonization: some cotton fibers are completely hydrolyzed into glucose and the nucleation is formed, and then the carbon microspheres are grown; for the other part, the glucose ring of the polysaccharide oligosaccharide formed by the incomplete hydrolysis of cotton fiber in the hydrothermal environment of high temperature and pressure breaks, then forms the particulate matters.

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Acid-Catalyzed Production of 5-Hydroxymethyl Furfural from d-Fructose in Subcritical Water

Cited by 463 publications

References 45 publications

One-Pot Synthesis of Furans from Various Saccharides Using a Combination of Solid Acid and Base Catalysts

One-Pot Synthesis of Furans from Various Saccharides Using a Combination of Solid Acid and Base Catalysts

Production of 5-Hydroxymethylfurfural (Hmf) via Fructose Dehydration: Effect of Solvent and Salting-Out

Evolution of Waster Cotton Fiber Hydro-Char Physicochemical Structure during Hydrothermal Carbonation

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