Synthesis of 3-substituted furans from 3-C-substituted hexuloses

Fayet, Catherine; Gelas, Jacques

doi:10.1016/s0008-6215(00)90136-8

Cited by 24 publications

(22 citation statements)

References 21 publications

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“…It is notable that Fayet and Gelas first reported the dehydration of fructose, glucose and polysaccharides in immonium and ammonium salts (also called ionic liquids). 25 For fructose, up to 70% HMF yield was achieved in the ionic liquid systems at 120 °C for 30 min. HMF yields from glucose and saccharose were about 5% and 30% under similar conditions.…”

Section: Developing Stage From 1980 To 2000mentioning

confidence: 97%

Hydroxymethylfurfural production from bioresources: past, present and future

2014

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5-Hydroxymethylfurfural (HMF) has been known as a product from hexose dehydration for over 100 years and is considered to be one of the most promising platform molecules that can be converted into a variety of interesting chemicals. HMF, together with furfural and 2,5-furandicarboxylic acid (FDCA) are derivatives of furan compounds, which were listed as the top 10 value-added bio-based chemicals by the US Department of Energy. The great and increasing interest in the production of furan derivatives from biomass resources is due to the great potential of furan derivatives as feedstock for bulk chemicals and fuels. HMF can be synthesized by dehydration of all types of C6 carbohydrates, including monomeric and polymeric carbohydrates, such as fructose, glucose, sucrose, starch, inulin, cellulose, and raw biomass.Numerous improvements and milestones have been made in the dehydration process during the past 130 years. The big challenge for the process of HMF production is its suitability for industrial scale yet being cost efficient. This perspective article will review the HMF development timeline, focusing on the important events, landmark contributions, engineering and practical challenges of HMF production.

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Section: Developing Stage From 1980 To 2000mentioning

confidence: 97%

Hydroxymethylfurfural production from bioresources: past, present and future

2014

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“…As early as 1983, it has been reported that the fructose can be efficiently converted to 5-HMF in a molten salt, pyridinium chloride. 62 However, almost no other research about this process has been reported in ILs in the following twenty years.…”

Section: Conversion Of Biomass To 5-hmf In Ilsmentioning

confidence: 99%

Recent advances in ionic liquid catalysis

2011

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“…We started our work to use a number of ILs and two pyridinium salts as both catalysts and solvents for the conversion of fructose to HMF at 80 • C for 1 h, including 1-H-3-methyl imidazolium chloride ([HMim]Cl), 25 1-butyl-3-methyl imidazolium hydrosulfate ([BMim]HSO 4 ), ethylammonium nitrate (EtNH 3 NO 3 ), 1,1,3,3-tetramethylguanidinium trifluoroacetate (TMG TFA), 1,1,3,3-tetramethylguanidinium lactate (TMG LAC), ChoCl-based deep eutectic mixtures which also belong to ILs (Table S1 in the ESI †), 23,26,27 pyridine hydrochloride (PyHCl), and pyridine p-toluenesulfate (PyTSA). 28 They include Brønsted acids, Lewis acids (ChoCl/metal chlorides), and bases (ChoCl/urea, TMG TFA and TMG LAC). The results are presented in Fig.…”

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confidence: 99%

Conversion of fructose to 5-hydroxymethylfurfural using ionic liquids prepared from renewable materials

et al. 2008

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Efficient conversion of fructose to 5-hydroxymethylfurfural is a key step for using carbohydrates to produce liquid fuels and value-added chemicals. Here we show that some ionic liquids synthesized from cheap renewable materials are very efficient for the conversion of fructose to HMF. The yield and selectivity could be higher than 90% as the reaction was conducted in an ethyl acetate/renewable IL biphasic system and the separation process had no cross-contamination. Moreover, the IL can be reused easily.Diminishing fossil fuel reserves and growing concerns about global warming indicate that sustainable resources are needed in the near future. 1 Biomass is abundant, renewable, and is distributed widely in nature, which are promising alternatives for the sustainable supply of liquid fuels and valuable intermediates (such as alcohols, aldehydes, ketones, and carboxylic acids) to the chemical industry for production of drugs and polymeric materials. 2 Carbohydrates comprise the main class of biomass compounds. 3 Utilization of biomass requires efficient methods to convert carbohydrates into a variety of chemical compounds. 4 It is known that the direct production of useful organic compounds from five and six-carbon carbohydrates is difficult. 5-Hydroxymethylfurfural (HMF 2), which is obtained from carbohydrates (e.g. glucose, sucrose and fructose (1)) by dehydration, is an important "bridge" for efficient use of carbohydrates (Scheme 1). 4-6 As a versatile intermediate, HMF can be converted to 2,5-furandicarboxyl acid (3), 2,5-dihydroxy methylfuran (4), 2,5-bis(hydroxymethyl)tetrahydrofuran (5), dimethylfuran (6) and other liquid alkanes by oxidation, hydrogenation,

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Synthesis of 3-substituted furans from 3-C-substituted hexuloses

Cited by 24 publications

References 21 publications

Hydroxymethylfurfural production from bioresources: past, present and future

Hydroxymethylfurfural production from bioresources: past, present and future

Recent advances in ionic liquid catalysis

Conversion of fructose to 5-hydroxymethylfurfural using ionic liquids prepared from renewable materials

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