Catalytic Conversion of Carbohydrates to Furanic Derivatives in the Presence of Choline Chloride

Jérôme, François; Vigier, Karine De Oliveira

doi:10.3390/catal7070218

Cited by 19 publications

(3 citation statements)

References 34 publications

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“…Interestingly, K D had a maximum value of 4 between 40 min and 60 min of reaction. This value is similar to, or even higher than, other investigations of biphasic systems, although they may have used different solvents [32][33][34].…”

Section: Chemical Reaction Model For the Conversion Of Sucrose To Hmfsupporting

confidence: 79%

Reaction Mechanism of the Microwave-Assisted Synthesis of 5-Hydroxymethylfurfural from Sucrose in Sugar Beet Molasses

et al. 2021

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5-hydroxymethylfurfural (HMF) stands out among the chemical products derived from biomass as a building block in the chemical industry. The conventional production of HMF is usually carried out from fructose, glucose, or other monosaccharides as feedstock, but sugar beet molasses, a by-product of the sugar industry containing sucrose (45–55%), is promising. This exploratory study used three aqueous stock solutions and one biphasic system as the sources of sucrose. The dehydration of sucrose to 5-hydroxymethylfurfural was assisted by microwave heating and subcritical water conditions. The maximum yield of HMF was 27.8 mol % for the aqueous solution of synthetic sucrose at 80 min of treatment. Although HMF yield was 7.1 mol % in the aqueous sugar beet molasses solution, it increased 2-fold after clarification (15.1 mol %) and 1.6-fold in the biphasic system (11.4 mol %). These are favorable outcomes since this is an exploratory investigation. The pseudo-first-order model fitted experimental data from the conversion of the sucrose from the stock solutions, and kinetic parameters were estimated and compared. The estimated reaction rate constant showed that inversion of sucrose is faster than fructose dehydration to HMF, but the latter reaction was the rate-determining step only for the biphasic system. The maximum partition coefficient value was four between 40 min and 60 min of reaction, calculated at room temperature. These predictions help investigators to estimate conversions and selectivity when pilot plants need to be simulated.

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Section: Chemical Reaction Model For the Conversion Of Sucrose To Hmfsupporting

confidence: 79%

Reaction Mechanism of the Microwave-Assisted Synthesis of 5-Hydroxymethylfurfural from Sucrose in Sugar Beet Molasses

et al. 2021

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“…With optimized conditions identified in water (Table 1, entry 4) and in LMM (Table 2, entry 7), [19] we next studied the generality of the alcohol substrate for this oxidation reaction. As for the reactions in water, benzylic alcohol derivatives with a MeO group at the ortho ‐, meta ‐, and para ‐positions ( 1 b – d ) reacted smoothly, affording the corresponding aldehydes 2 b – d in 79–87 % yield (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Selective Aerobic Oxidation of Alcohols in Low Melting Mixtures and Water and Use for Telescoped One‐Pot Hybrid Reactions

et al. 2022

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An efficient, selective and sustainable protocol was developed for the CuCl 2 /TEMPO/TMEDA‐catalyzed aerobic oxidation of activated alcohols to the corresponding carbonyl compounds using water or the environmentally friendly low melting mixture (LMM) d ‐fructose‐urea as the reaction medium. Such oxidation reactions proceed under mild (room temperature or 40 °C) and aerobic conditions, with the carbonyl derivatives isolated in up to 98 % yield and within 4 h reaction time when using the above‐mentioned LMM. The potential application of this methodology is demonstrated by setting up useful telescoped, one‐pot two‐step hybrid transformations for the direct conversion of primary alcohols either into secondary alcohols or into valuable nitroalkenes, by combining oxidation processes with nucleophilic additions promoted by highly polarized organometallic compounds (Grignard and organolithium reagents) or with nitroaldol (Henry) reactions, respectively.

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“…32,33 Therefore, in the present study, we try to obtain a better extraction of HMF using aqueous DES (ChCl-urea) and introducing NaCl into the aqueous solution. Jeŕome et al 34 indicated that the yield and selectivity of HMF can also be enhanced in aqueous ChCl solution using MIBK as the extraction solvent. Furthermore, to our best knowledge, there is still no liquid−liquid equilibrium (LLE) data available for the combination of systems containing HMF, aqueous DES (ChCl-urea) solution, and organic solvent in the absence and presence of NaCl.…”

Section: Introductionmentioning

confidence: 99%

Choline Chloride Urea Effect on Liquid–Liquid Equilibria of 5-Hydroxymethylfurfural–Water–Organic Solvent Systems in the Absence and Presence of Sodium Chloride

et al. 2021

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Deep eutectic solvent (DES) has demonstrated its ability to improve the yield and selectivity in the 5-hydroxymethylfurfural (HMF) production process. Liquid−liquid extraction is a beneficial process in HMF production to recover HMF from the reaction medium. In the present study, the effect of DES (choline chloride urea) on the liquid−liquid equilibria (LLE) of HMF−water−organic solvent (methyl isobutyl ketone (MIBK) or 2pentanol) systems in the absence and presence of sodium chloride (NaCl) was investigated at 313.15 K and atmospheric pressure (0.1 MPa). The tie-lines of the multicomponent systems were measured using several analytical methods. According to the experimental results, the extraction performance decreased with an increase in DES concentration. However, the addition of 10 wt % NaCl into the HMF aqueous DES solution can induce stronger liquid− liquid phase splitting, enhancing the separation factors and distribution coefficients of HMF by around 2.7 and 1.6 times, respectively. Additionally, MIBK showed better extraction performance in the presence of DES and NaCl with the separation factors 2.6 times higher than those of 2-pentanol and the HMF distribution coefficients above 1.8. The LLE of the multicomponent systems were correlated well with the nonrandom two-liquid (NRTL) model.

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Catalytic Conversion of Carbohydrates to Furanic Derivatives in the Presence of Choline Chloride

Cited by 19 publications

References 34 publications

Reaction Mechanism of the Microwave-Assisted Synthesis of 5-Hydroxymethylfurfural from Sucrose in Sugar Beet Molasses

Reaction Mechanism of the Microwave-Assisted Synthesis of 5-Hydroxymethylfurfural from Sucrose in Sugar Beet Molasses

Selective Aerobic Oxidation of Alcohols in Low Melting Mixtures and Water and Use for Telescoped One‐Pot Hybrid Reactions

Choline Chloride Urea Effect on Liquid–Liquid Equilibria of 5-Hydroxymethylfurfural–Water–Organic Solvent Systems in the Absence and Presence of Sodium Chloride

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