Abstract
Conversion of carbohydrate into 5-hydroxymethylfurfural (5- HMF), a versatile, key renewable platform compound is regarded as an important transformation in biomass-derived carbohydrate chemistry. A variety of ILs, not only acidic but also alkaline ILs, were synthesized and used as catalyst in the production of 5-HMF from disaccharide. Several factors including reaction temperature, IL dosage, solvent and reaction time,were found to influence the yield of 5-HMF from cellobiose. Of the ILs tested, hydroxy-functionalized ionic liquid (IL), 1-hydroxyethyl-3-methylimidazolium tetrafluoroborate ([AEMIM]BF4) showed the highest catalytic activity and selectivity. 5-HMF yield of 68.71% from sucrose was obtained after 6 hrs at 160 °C. At the same condition with cellobiose as substrate, 5-HMF yield was 24.73%. In addition, 5-HMF also exhibited good stablity in this reaction system. Moreover, a kinetic analysis was carried out in both acidic and alkaline IL-catalyzed system, suggesting main side reaction in the conversion of fructose catalyzed by acidic and alkaline IL was polymerization of fructose and 5-HMF degradation, respectively.
Highlights
Solvent 2-Butanol dimethyl acetamide (DMAc) NMP DMSO DMSO DMSO DMSO DMSO DMSO DMSO bubbling COX and NOX through the solution alternately[26,27,28,29], to our knowledge there have been little reports of the use of alkaline ILs as a catalyst for the conversion of carbohydrates to 5-HMF
Among different kinds of solvents used for the conversion of sucrose with [MIMPS]3PW12O40 as catalyst (P < 0.05) (Table 1, entry 1–4), a comparable high yield of 5-HMF was obtained using 2-Butanol as solvent (Table 1, entry 1), compared to DMAc, NMP and DMSO (Table 1, entry 2–4), consistent with the results in a previous study[30]
The 5-HMF yield, catalyzed by alkaline ILs (Table 1, entry 5–8) was invariably higher than that obtained with the acidic catalyst (Table 1, entry 1–4)
Summary
Solvent 2-Butanol DMAc NMP DMSO DMSO DMSO DMSO DMSO DMSO DMSO bubbling COX and NOX through the solution alternately[26,27,28,29], to our knowledge there have been little reports of the use of alkaline ILs as a catalyst for the conversion of carbohydrates to 5-HMF. In the present study, Brønsted acidic IL, 1-(3-sulfonic acid) propyl-3-methylimidazolium phosphotungstate ([MIMPS]3PW12O40), and a variety of alkaline ILs, 1-butyl-3-methylimidazolium hydroxide ([BMIM]OH), 1-ethyl-3-methylimidazolium hydroxide ([EMIM]OH), 1-butyl-3-methylimidazolium carbonate ([BMIM] HCO3) and hydroxy-functionalized IL, 1-hydroxyethyl-3-methylimidazolium tetrafluoroborate ([AEMIM]BF4) were synthesized and used as catalyst in the conversion of disacharide (sucrose and cellobiose) to 5-HMF, which has not been reported. Kinetic analysis on reaction catalyzed by different ILs was carried out to identify the catalytic effect of different ILs-catalyst on the conversion of dissacharide to 5-HMF
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