High yield production and purification of 5‐hydroxymethylfurfural

Abstract

Conversion of carbohydrates to 5-hydroxymethylfurfural (HMF) will provide a new step toward achieving renewable biomass-based chemicals and fuels platform. Recently, the excellent yield of HMF (91.0%) in dimethyl sulfoxide (DMSO) catalyzed by sulfonated carbon was demonstrated, but the separation of HMF from the reaction mixture remains challenging because of the high boiling point of DMSO. As a solution, herein, low boiling point solvent tetrahydrofuran (THF) mixed with DMSO was used for the fructose dehydration and high yield of HMF (98.0%) was still obtained. Besides, the stability of the sulfonated carbonaceous catalyst was also confirmed. More importantly, HMF from the reaction solution was successfully separated by using simple extraction method, and high purity of HMF (ca. 96.4%) was obtained. Compared with pure DMSO solvent, the combination of low boiling point THF with DMSO not only gives higher yield of HMF, but also improves the separation efficiency and reduces environmental risk.

Production of 5-Hydroxymethylfurfural from Fructose Catalyzed by Sulfonated Bamboo-Derived Carbon Prepared by Simultaneous Carbonization and Sulfonation

“…However, it also promoted the conversion of HMF to byproducts. At 150 °C, its yield decreased after 60 min, probably due to HMF decomposition to levulinic acid and HMF self-polymerization or cross-polymerization at high temperature (Wang et al 2013). It should be noted that no obvious increase of HMF yield was observed when the temperature was raised from 140 °C (92.3 % HMF yield in 60 min) to 150 °C.…”

“…The addition of a low boiling point solvent of THF into DMSO not only can increase the selectivity to HMF, but it also improves the separation efficiency (Wang et al 2013). On the one hand, in THF, fructose is very favorable to be converted into the furanoid form, which is much easier to generate HMF (West et al 2008;Zhu et al 2011;Wang et al 2013), and on the other hand, miscibility of THF with water can take the generated water away from liquid phase, preventing the side reactions due to the presence of water molecules (Chan and Zhang 2009;Cao et al 2011;Wang et al 2013). The influence of the volume ratio of THF/DMSO on fructose dehydration to HMF is shown in Table 2 (entries 4 to 8).…”

“…The HMF yield exhibited a slight increase from 88.3 % to 89.2 % as the volume ratio of THF/DMSO increased from 1/9 to 3/7, while no obvious change of fructose conversion occurred. However, HMF yield as well as fructose conversion decreased with further increase in the volume ratio of THF/DMSO, due to the decreased solubility of fructose as the volume ratio of THF/DMSO increases (Wang et al 2013). Therefore, THF/DMSO mixture in volume ratio of 3/7 was used as the suitable solvent for further investigation.…”

Characterization of Value-Added Non-Carbohydrate Compounds Solubilized during Acidic Hot Water Flowthrough Pretreatment of Poplar Wood

“…On the contrary, the addition of sulfuric acid in turn alleviated the selectivity of aromatic compounds. The HMF as an important platform intermediate for the production of the biofuel dimethylfuran (DMF) and other molecules (Rosatella et al 2011) could be extracted with low boiling point solvent tetrahydrofuran (THF) or diethyl ether for purification (Wang et al 2013).…”

Catalytic conversion of biorenewable-carbohydrate sources to 5-Hydroxymethylfurfural: a platform molecule for future chemical and energy

“…78 GTS was prepared in a similar manner like Glu-TsOH but with a slight modification by adding an inorganic salt, sodium sulfate. 77 , it was established that combination of low boiling point THF with DMSO not only gives higher yield of HMF, but also improves separation efficiency.…”