Preparation of 5-hydroymethylfurfural by dehydration of fructose in the presence of acidic ionic liquid

Bao, Quanxi; Qiao, Ke; Tomida, Daisuke; Yokoyama, Chiaki

doi:10.1016/j.catcom.2007.12.002

Cited by 149 publications

(106 citation statements)

References 19 publications

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“…[21,22] Recently, room temperature ionic liquids (ILs) have also been employed in the dehydration of hexoses into HMF. [8,[23][24][25][26][27] The neutral ILs were used as reaction media in which catalysts and substrates were dissolved. For example, the IL [Emim]Cl was an effective solvent in the dehydration of d-fructose to HMF with a metal chloride as catalyst, in which a 70 % yield of HMF was achieved.…”

Section: Introductionmentioning

confidence: 99%

“…[24] On the other hand, Bao et al reported that the Lewis acidic 3-allyl-1-(4-sulfurylchloride butyl)-imidazolium trifluoromethanesulfonate ([ASCBI][Tf]) effectively catalyzed the dehydration of d-fructose under microwave irradiation. [25] Moreover, special ILs, such as 1-H-3-methyl imidazolium chloride and choline chloride/citric acid, have also been used as both solvent and catalyst for the reaction, with a reported IL to d-fructose molar ratio of 12 or 5, respectively. [26,27] However, in these reported works, the ILs mainly played a role as the solvent and were consumed in considerably large amounts.…”

Section: Introductionmentioning

confidence: 99%

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Efficient and Selective Dehydration of Fructose to 5‐Hydroxymethylfurfural Catalyzed by Brønsted‐Acidic Ionic Liquids

2010

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The dehydration of D‐fructose and glucose has been studied with acidic ionic liquids as catalysts. A series of Brønsted‐acidic ionic liquids has been synthesized and tested in the dehydration of D‐fructose. The results showed that N‐methyl‐2‐pyrrolidonium methyl sulfonate [NMP]+[CH3SO3]− and N‐methyl‐2‐pyrrolidonium hydrogen sulfate [NMP]+[HSO4]− have high catalytic activity. Highly efficient and selective dehydration of D‐fructose to 5‐hydroxymethylfurfural (HMF) was achieved in dimethyl sulfoxide (DMSO) under mild conditions. For example, a 72.3 % yield of HMF with 87.2 % selectivity were obtained for 2 h at 90 °C in the presence of 7.5 mol % [NMP]+[CH3SO3]−. The effects of the reaction temperature, time, and solvent were investigated in detail. The catalyst and solvent can be recycled for the dehydration of D‐fructose. The Hammett method was used to determine the acidities of these ionic liquids, which indicated that the acidity and molecular structure have strong effects on the catalytic activity of ionic liquids. Based on the experimental results, a possible reaction mechanism for the dehydration of D‐fructose is proposed.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Efficient and Selective Dehydration of Fructose to 5‐Hydroxymethylfurfural Catalyzed by Brønsted‐Acidic Ionic Liquids

2010

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“…Among the current renewable and sustainable alternatives, the 5-hydroxymethylfurfural (HMF) converted from sugars is a versatile and key intermediate in biofuel and petroleum chemistry [95,96]. The ionic liquids have been already reported for the production of HMF [97][98][99] and very recently the application of the polyacids based catalyst with excellent efficiency and very good selectivity was reported [100]. The combination of both catalysts seems to be the next logical step, targeting higher stability and more importantly higher productivity by applying it in heterogeneous in-flow reactions.…”

Section: Where Is the Future?mentioning

confidence: 99%

Hybrid Organic-Inorganic Materials Based on Polyoxometalates and Ionic Liquids and Their Application in Catalysis

Ivanova

2014

ISRN Chemical Engineering

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An overview of the recent advances in the field of polyoxometalate, ionic liquid hybrids, is proposed with a special attention paid to their application in catalysis, more precisely biphasic and heterogeneous catalysis. Both components of the hybrids are separately outlined pointing to their useful properties and potential for catalysis, followed by the description of the hybrids preparation and synergy between components in a large range of organic transformations. And finally a vision on the future developments is proposed.

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“…The best yields of HMF from glucose and fructose are achieved with homogeneous ionic liquid catalyst systems where ionic liquid is either catalyst or solvent [17,56,58]. Glucose has been efficiently converted to HMF in a homogeneous ionic liquid catalyst system containing Lewis acids (metal chlorides), whereas acidic ionic liquids have demonstrated to efficiently dehydrate fructose [56,58].…”

Section: Homogeneous Catalysismentioning

confidence: 99%

“…Glucose has been efficiently converted to HMF in a homogeneous ionic liquid catalyst system containing Lewis acids (metal chlorides), whereas acidic ionic liquids have demonstrated to efficiently dehydrate fructose [56,58].…”

Section: Homogeneous Catalysismentioning

confidence: 99%

The Challenge of Efficient Synthesis of Biofuels from Lignocellulose for Future Renewable Transportation Fuels

Mäki‐Arvela

Salminen

Riittonen

et al. 2012

International Journal of Chemical Engineering

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Dehydration of sugars to 5-hydroxymethylfurfural (HMF) has recently been under intensive study by a multitude of research groups. On the other hand, when lignocellulosic biomass is applied as the starting material, very few studies can be found in the open literature. The direct synthesis of HMF, in line with the idea of “one-pot” synthesis strategy from lignocellulose, is demanding since the overall process should encompass dissolution, hydrolysis, and dehydration steps in a single processing unit. Ionic liquid-assisted methods to produce hydroxymethyl-furfural directly from lignocellulosic biomass are reported here together with a short overview of the most important biofuels. In reality, HMF is not suitable to be used as a single-component fuel as such, and, consequently, methods to produce HMF derivatives suitable as liquid fuels are reported.

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Preparation of 5-hydroymethylfurfural by dehydration of fructose in the presence of acidic ionic liquid

Cited by 149 publications

References 19 publications

Efficient and Selective Dehydration of Fructose to 5‐Hydroxymethylfurfural Catalyzed by Brønsted‐Acidic Ionic Liquids

Efficient and Selective Dehydration of Fructose to 5‐Hydroxymethylfurfural Catalyzed by Brønsted‐Acidic Ionic Liquids

Hybrid Organic-Inorganic Materials Based on Polyoxometalates and Ionic Liquids and Their Application in Catalysis

The Challenge of Efficient Synthesis of Biofuels from Lignocellulose for Future Renewable Transportation Fuels

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