Bifunctional Imidazole-Benzenesulfonic Acid Deep Eutectic Solvent for Fructose Dehydration to 5-Hydroxymethylfurfural

Ruan, Chencong; Mo, Fan; Qin, Hao; Cheng, Hongye; Chen, Lifang; Qi, Zhiwen

doi:10.1007/s10562-020-03309-6

Cited by 20 publications

(11 citation statements)

References 45 publications

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“…During the experimental process, we observe that as the initial glucose concentration increased, the amount of humins or carbonaceous materials increased. It is interesting that no LA was detected in all the studied reaction mixtures, indicating that 5-HMF is relatively stable in the TEBAC/FA (1:2) DES environment and avoids further hydration reaction. , …”

Section: Results and Discussionmentioning

confidence: 92%

Insights into the Play of Novel Brønsted Acid-Based Deep Eutectic Solvents for the Conversion of Glucose into 5-Hydroxymethylfurfural without Additional Catalysts

Tao

Zhang

et al. 2022

Ind. Eng. Chem. Res.

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5-Hydroxymethylfurfural (5-HMF) is a versatile bio-platform chemical that connects biomass to a variety of different fuels, chemicals, and materials. In this work, novel Brønsted acid-based deep eutectic solvents (DESs) with both solvent and catalytic functionalities for glucose dehydration into 5-HMF were developed without the need of additional metal salt catalysts or heterogeneous catalysts. The types of hydrogen bond donor (HBD) and hydrogen bond acceptor (HBA), the ratio of HBD to HBA of the DES, heating time, reaction temperature, initial glucose concentration, and moisture content of the DES were systematically investigated to reveal the interplay of the DES in the conversion of glucose to 5-HMF. The most effective DES was found to be triethyl benzyl ammonium chloride (TEBAC)/formic acid (FA) (molar ratio: 2:1) with a 5-HMF yield of 30.5 ± 1.0% in glucose dehydration and approximately 100% glucose conversion (initial glucose concentration: 2.5 wt %) in 60 min at 150 °C. Most importantly, after five cycles, the TEBAC/FA (1:2) DES retained high stability and catalytic activity, with the yield of 5-HMF remaining 30.1 ± 0.5%. Interestingly, as the water content of the DES increased to 70%, the 5-HMF yield increased to 36.5 ± 1.0% along with an 8.01 ± 1.4% yield of levulinic acid. The finding of this study provided insights into the TEBAC/FA (1:2) DES with dual capabilities that might support more efficient bio-based commodity chemical production methods.

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Section: Results and Discussionmentioning

confidence: 92%

Insights into the Play of Novel Brønsted Acid-Based Deep Eutectic Solvents for the Conversion of Glucose into 5-Hydroxymethylfurfural without Additional Catalysts

Tao

Zhang

et al. 2022

Ind. Eng. Chem. Res.

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“…Hence, the catalytic efficiency of the dehydration reaction might be influenced by some dehydration parameters, including the DES acidity, d -fructose-to-catalyst mass ratio, dehydration temperature, dehydration duration, and so on. 5-HMF is very unstable in water, it easily undergoes a hydration reaction and degrades into levulinic acid and formic acid . Hence, a DES was selected as the solvent and catalyst in the reaction system.…”

Section: Resultsmentioning

confidence: 99%

A Hybrid Process for Valorization of d-Fructose to 2,5-Bis(hydroxymethyl)furan by Bridging Chemocatalysis and Biocatalysis in a Betaine:Benzenesulfonic Acid System

Jiang

et al. 2022

ACS Sustainable Chem. Eng.

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Biobased 2,5-bis(hydroxymethyl)furan is a versatile building block for the production of drugs, polymers, crown ethers, bioactive compounds, and value-added intermediates. To explore a more efficient route to synthesize 2,5-bis(hydroxymethyl)furan, a tandem transformation by quick dehydration with a deep eutectic solvent betaine:benzenesulfonic acid (Bet:BSA) and mild bioreduction with recombinant Escherichia coli (E. coli) DCF was developed for converting D-fructose into 2,5-bis(hydroxymethyl)furan. The 5-hydroxymethylfurfural yield reached 62.3 ± 1.6% (based on D-fructose) in Bet:BSA at 120 °C after a short time (2 min). D-Fructose-valorized 5-hydroxymethylfurfural was biologically transformed to 2,5-bis(hydroxymethyl)furan by newly constructed recombinant E. coli DCF containing reductase and formate dehydrogenase at 40 °C and pH 7.5 after 48 h, with a yield of 99.6 ± 0.1% (based on 5-hydroxymethylfurfural) in Bet:BSA-water containing the cosubstrate HCOONa (5-HMF-to-HCOONa molar ratio, 1:2.5). Meanwhile, 150 mM commercial 5-hydroxymethylfurfural was transformed into 2,5-bis(hydroxymethyl)furan in a yield of 94.4 ± 0.9%. An efficient hybrid process was constructed to valorize D-fructose to 2,5-bis(hydroxymethyl)furan in Bet:BSAwater, which has good industrial application potential.

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“…[31,32] Furthermore, ILs can play a dual role as solvent and catalyst for the intensification of reaction coupling separation. [33][34][35] Thus, the employment of bifunctional ILs is considered as promising route for direct dehydration of biomass derivatives to produce HMF and further transformation of HMF. These features infer ILs can be used as promising solvents/cosolvents and/or catalysts/cocatalysts to achieve target products of biomass processing for sustainable development, which will be discussed in detail in the following Sections 3 and 4.…”

Section: Ionic Liquidsmentioning

confidence: 99%

“…They are remarkable media to design various types of catalysts in the forms of complexes, clusters, ligands, gels, and ions within the reaction for facilitating their catalytic activity [31,32] . Furthermore, ILs can play a dual role as solvent and catalyst for the intensification of reaction coupling separation [33–35] . Thus, the employment of bifunctional ILs is considered as promising route for direct dehydration of biomass derivatives to produce HMF and further transformation of HMF.…”

Section: Ionic Liquids and Deep Eutectic Solventsmentioning

confidence: 99%

Advances of Ionic Liquids and Deep Eutectic Solvents in Green Processes of Biomass‐Derived 5‐Hydroxymethylfurfural

et al. 2022

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5-Hydroxymethylfurfural (HMF) is identified as an important bio-based platform chemical to bridge petroleum-based and biomass-based resources. It can be obtained through dehydration of various carbohydrates as well as converted to valueadded fuels and chemicals. As designer solvents, ionic liquids (ILs) and deep eutectic solvents (DESs) have been widely used in catalytic transformation of biomass derivatives to various chemicals. This Review summarizes recent progress in experimental and theoretical studies on dehydration of carbohy-drates such as fructose, glucose, sucrose, cellobiose, chitosan, cellulose, inulin, and even raw biomass to generate HMF using ILs and DESs as catalysts/cocatalysts and/or solvents/cosolvents. It also gives an overview of IL and DES-involved catalytic transformation of HMF to downstream products via oxidation, reduction, esterification, decarboxylation, and so forth. Challenges and prospects of ILs and DESs are also proposed for further production of HMF and HMF derivatives from biomass in green and sustainable processes.

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Bifunctional Imidazole-Benzenesulfonic Acid Deep Eutectic Solvent for Fructose Dehydration to 5-Hydroxymethylfurfural

Cited by 20 publications

References 45 publications

Insights into the Play of Novel Brønsted Acid-Based Deep Eutectic Solvents for the Conversion of Glucose into 5-Hydroxymethylfurfural without Additional Catalysts

Insights into the Play of Novel Brønsted Acid-Based Deep Eutectic Solvents for the Conversion of Glucose into 5-Hydroxymethylfurfural without Additional Catalysts

A Hybrid Process for Valorization of d-Fructose to 2,5-Bis(hydroxymethyl)furan by Bridging Chemocatalysis and Biocatalysis in a Betaine:Benzenesulfonic Acid System

Advances of Ionic Liquids and Deep Eutectic Solvents in Green Processes of Biomass‐Derived 5‐Hydroxymethylfurfural

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