Green process for production of 5-hydroxymethylfurfural from carbohydrates with high purity in deep eutectic solvents

Zuo, Miao; Le, Kai; Li, Zheng; Jiang, Yetao; Zeng, Xianhai; Tang, Xing; Sun, Yong

doi:10.1016/j.indcrop.2017.01.027

Cited by 122 publications

(82 citation statements)

References 46 publications

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“…ChCl, a low‐cost, biodegradable and safe quaternary ammonium salt, can also be extracted from biomass and can form a deep eutectic solvent (DES) system if combined with hydrogen donors such as carboxylic acids, alcohols and hexoses . Therefore, ChCl‐based DES systems such as ChCl/oxalic acid, ChCl/citric acid, ChCl/fructose and ChCl/glucose, which are increasingly studied, consume significant amounts of ChCl. In an attempt to further enhance the HMF yield, we investigated the dehydration of fructose in a ChCl aqueous solution (CAS), which, to the best of our knowledge, has not been previously applied for the valorization of biomass (Figure ).…”

Section: Resultsmentioning

confidence: 99%

Development of Betaine‐Based Sustainable Catalysts for Green Conversion of Carbohydrates and Biomass into 5‐Hydroxymethylfurfural

Feng

Gao

et al. 2019

ChemSusChem

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Renewable and sustainable betaine‐based catalysts (BX) derived from the betaine sugar industry or ChCl were developed for the production of 5‐hydroxymethylfurfural (HMF) from various carbohydrates. The HMF yields in the BX‐based media reached up to 88 %, 66 %, 37 % and 53 %, for the conversion of fructose, glucose, cellulose, and lignocellulosic biomass, respectively. In addition, choline‐O‐sulfate was synthesized and demonstrated to be an efficient catalyst for the conversion of fructose to HMF. From the perspective of green and sustainable chemistry, this work demonstrates benefits not only in the preparation of sustainable catalysts but also the green production of HMF from biomass.

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Section: Resultsmentioning

confidence: 99%

Development of Betaine‐Based Sustainable Catalysts for Green Conversion of Carbohydrates and Biomass into 5‐Hydroxymethylfurfural

Feng

Gao

et al. 2019

ChemSusChem

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“…Therefore, numerous biomass‐derived polyols/polyacids are able to be used as the HBDs . For instance, fructose (HBD) and choline chloride (ChCl, HBA) can form a deep eutectic mixture at different molar ratios, in which fructose could be in situ converted to HMF with a yield greater than 90% in the presence of acid catalysts . Interestingly, a novel solvent‐free system was demonstrated in these cases for the conversion of fructose to HMF, and the high HMF yield is mainly attributed to the stabilization of HMF by the hydrogen‐bonding interactions in the deep eutectic mixture …”

Section: Introductionmentioning

confidence: 99%

Efficient synthesis of bio‐based monomer 2,5‐bishydroxymethylfuran by the solvent‐free hydrogenation of 5‐hydroxymethylfurfural‐based deep eutectic mixture

Wang

Wei

Feng

et al. 2020

J of Chemical Tech & Biotech

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BACKGROUND: Biomass holds the promise to provide a sustainable future for the chemical industry. 2, 5-Bishydroxymethylfuran (BHMF) is a versatile bio-based diol with a broad range of potential applications in many polymeric materials, artificial fibers and drugs. However, the controlling of the BHMF selectivity in hydrogenation of biomass-derived 5-hydroxymethylfurfural (HMF) with complex transformation pathways is always a great challenge especially under solvent-free conditions in which many side reactions may occur due to its rich reducible groups.RESULTS: A facile and effective approach was developed for the selective synthesis of BHMF by solvent-free hydrogenation of a deep eutectic mixture consisting of HMF (75 wt%) and choline chloride (ChCl), by which a BHMF selectivity up to 94.6% was gained at full HMF conversion over Raney Co at 100°C in 4 h. In addition, the HMF conversion and selectivity toward BHMF can be regulated and controlled through altering the strength of hydrogen-bonding interactions of HMF-based deep eutectic mixtures (ChCl-HMF mixtures). CONCLUSION:We developed an effective approach that allows the solvent-free synthesis of BHMF via hydrogenation of HMFbased deep eutectic mixtures. The extraordinary BHMF selectivity in the solvent-free hydrogenation of HMF is reasonably attributed to the hydrogen-bonding interactions formed between ChCl and HMF/BHMF which greatly suppresses the side reactions of HMF and the over-reduction of BHMF. Scheme 1. Hydrogenation of 5-hydroxymethylfurfural (HMF) to 2,5-bishydroxymethylfuran (BHMF) and probable over-reduction products. MFA, 5-methylfurfuryl alcohol; BHMTHF, 2,5-bis-(hydroxymethyl)tetrahydrofuran; DMF, 2,5-dimethylfuran.Synthesis of bio-based monomer 2,5-bishydroxymethylfuran www.soci.org

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“…Shi et al [19] investigated the direct conversion of cellulose into 5-HMF using concentrated NaHSO4 and ZnSO4 as co-catalysts in a biphasic system, and observed 53 mol % yield of 5-HMF. Zuo [20] investigated the dehydration of fructose conversion to 5-HMF by using homogeneous and heterogeneous Brönsted acids, and found that higher 5-HMF yields were produced through lower concentrations of inorganic acid (extremely-low HCl and H2SO4, 90.3% and 82.8%, respectively); however, the conversion of 5-HMF to byproducts was enhanced in this solvent system [21]. Moreover, the interaction between DMSO and carbohydrates also benefited the conversion of carbohydrates to 5-HMF [22].…”

Section: Introductionmentioning

confidence: 99%

Conversion of Carbohydrates into Platform Chemicals Catalyzed by Alkaline Ionic Liquids

Zhang

Wang

et al. 2017

Catalysts

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Green process for production of 5-hydroxymethylfurfural from carbohydrates with high purity in deep eutectic solvents

Cited by 122 publications

References 46 publications

Development of Betaine‐Based Sustainable Catalysts for Green Conversion of Carbohydrates and Biomass into 5‐Hydroxymethylfurfural

Development of Betaine‐Based Sustainable Catalysts for Green Conversion of Carbohydrates and Biomass into 5‐Hydroxymethylfurfural

Efficient synthesis of bio‐based monomer 2,5‐bishydroxymethylfuran by the solvent‐free hydrogenation of 5‐hydroxymethylfurfural‐based deep eutectic mixture

Conversion of Carbohydrates into Platform Chemicals Catalyzed by Alkaline Ionic Liquids

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