Nouvelle méthode de préparation du 5-hydroxyméthyl-2-furaldéhyde par action de sels d'ammonium ou d'immonium sur les mono-, oligo- et poly-saccharides. Accès direct aux 5-halogénométhyl-2-furaldéhydes

Fayet, Catherine; Gelas, Jacques

doi:10.1016/0008-6215(83)88406-7

Cited by 66 publications

(13 citation statements)

References 22 publications

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“…This bond is easily hydrolyzed upon heating in ILs whereby the single units of fructose and glucose are exposed to further reaction. [40] Early work by Fayet and Gelas [38] explored the dehydration of sucrose in pyridinium-based ILs resulting in an HMF yield of 30 %. Since no other catalyst was present, it is reasonable to believe that the fructose unit was easily converted to HMF whereas the glucose remained unreacted.…”

Section: Glucosementioning

confidence: 99%

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Synthesis of 5‐(Hydroxymethyl)furfural in Ionic Liquids: Paving the Way to Renewable Chemicals

et al. 2011

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The synthesis of 5-(hydroxymethyl)furfural (HMF) in ionic liquids is a field that has grown rapidly in recent years. Unique dissolving properties for crude biomass in combination with a high selectivity for HMF formation from hexose sugars make ionic liquids attractive reaction media for the production of chemicals from renewable resources. A wide range of new catalytic systems that are unique for the transformation of glucose and fructose to HMF in ionic liquids has been found. However, literature examples of scale-up and process development are still scarce, and future research needs to complement the new chemistry with studies on larger scales in order to find economically and environmentally feasible processes for HMF production in ionic liquids. This Minireview surveys important progress made in catalyst development for the synthesis of HMF in ionic liquids, and proposes future research directions in process technology.

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Section: Glucosementioning

confidence: 99%

“…The first reported example of fructose conversion to HMF in ILs is a somewhat overlooked publication from the early 1980s. [38] Fructose was converted to HMF in pyridinium-and ammoniumbased ILs with halides, trifluoroacetate, and tosylate as anions.…”

Section: Fructosementioning

confidence: 99%

Synthesis of 5‐(Hydroxymethyl)furfural in Ionic Liquids: Paving the Way to Renewable Chemicals

et al. 2011

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“…[4] The formation of HMF from fructose is achieved readily at elevated temperatures in high-boiling molecular solvents or ionic liquids with or without an acid catalyst. [5][6][7][8][9][10] The most important industrial method for fructose production is by the enzymatic isomerization of glucose syrup, a process yielding only about 50 % fructose. [11] Direct conversion of the obtained aqueous glucose/fructose mixture would be problematical since the dehydration in water suffers from side reactions by which HMF is rehydrated to leuvulinic acid and formic acid.…”

Section: Introductionmentioning

confidence: 99%

Metal‐Free Dehydration of Glucose to 5‐(Hydroxymethyl)furfural in Ionic Liquids with Boric Acid as a Promoter

Ståhlberg

Rodríguez-Rodríguez

Fristrup

et al. 2011

Chemistry A European J

190

139

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The dehydration of glucose and other hexose carbohydrates to 5-(hydroxymethyl)furfural (HMF) was investigated in imidazolium-based ionic liquids with boric acid as a promoter. A yield of up to 42% from glucose and as much as 66% from sucrose was obtained. The yield of HMF decreased as the concentration of boric acid exceeded one equivalent, most likely as a consequence of stronger fructose-borate chelate complexes being formed. Computational modeling with DFT calculations confirmed that the formation of 1:1 glucose-borate complexes facilitated the conversion pathway from glucose to fructose. Deuterium-labeling studies elucidated that the isomerization proceeded via an ene-diol mechanism, which is different to that of the enzyme-catalyzed isomerization of glucose to fructose. The introduced non-metal system containing boric acid provides a new direction in the search for catalyst systems allowing efficient HMF formation from biorenewable sources.

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“…[143] In the initial work reported in this field, fructose was converted to HMF in 70 % yield using pyridinium chloride, however they found that glucose yielded only 5 % HMF under similar conditions. [144] In the next stage of development, dehydration of fructose was studied in ionic liquids 1-butyl-3methylimidazolium tetrafluoroborate and 1-butyl-3-methylimidazolium hexafluorophosphate, using DMSO as a co solvent, in the presence of an acid catalyst (Amberlyst-15). [145] In this work Lansalot-Matras et al, reported that only trace amounts of HMF is formed in pure DMSO under catalyst free conditions and addition of IL enhanced the yield to 36 % after [118] Methylimidazolium chloride Soybean straw and corn straw hydrolysis, 70 8C [119] 3-Propylsulfonic-triethylammonium hydrogensulfate Cellulose hydrolysis at 100 8C 99 % TRS yield [109] 4-Butylsulfonic-trimethylammonium hydrogensulfate Cellulose hydrolysis to glucose, at 80-120 8C.…”

Section: Dehydration Of Carbohydrates To Renewable Feedstock Chemicalmentioning

confidence: 99%

Ionic Liquids in Biomass Processing

Amarasekara

2018

Israel Journal of Chemistry

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The ionic liquids have emerged as new solvents and catalysts for processing biomass to value added chemicals and fuels. This review will present the recent developments in applications of ionic liquids in lignocellulosic biomass pretreatments, depolymerization, biodiesel synthesis, dehydration of carbohydrates to renewable feedstock chemicals as well as further transformations of biomass derived feedstocks such as furfural, 5‐hydroxymethylfurfural and levulinic acid to value added chemicals. In addition, the recycling of ionic liquids used in biomass processing is also discussed in the review.

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Nouvelle méthode de préparation du 5-hydroxyméthyl-2-furaldéhyde par action de sels d'ammonium ou d'immonium sur les mono-, oligo- et poly-saccharides. Accès direct aux 5-halogénométhyl-2-furaldéhydes

Cited by 66 publications

References 22 publications

Synthesis of 5‐(Hydroxymethyl)furfural in Ionic Liquids: Paving the Way to Renewable Chemicals

Synthesis of 5‐(Hydroxymethyl)furfural in Ionic Liquids: Paving the Way to Renewable Chemicals

Metal‐Free Dehydration of Glucose to 5‐(Hydroxymethyl)furfural in Ionic Liquids with Boric Acid as a Promoter

Ionic Liquids in Biomass Processing

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