Sulfonated polyaniline as a solid organocatalyst for dehydration of fructose into 5-hydroxymethylfurfural

Dai, Jinhang; Zhu, Liangfang; Tang, Dianyong; Fu, Xun; Tang, Jinqiang; Guo, Xiawei; Hu, Changwei

doi:10.1039/c6gc03604j

Cited by 72 publications

(34 citation statements)

References 53 publications

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“…Despite a number of examples demonstrating the successful conversion of fructose into HMF, most of them do not meet practical requirements, due to the high cost of the refined input carbohydrate substrates (mostly, fructose and sucrose). If naturally abundant glucose or polyglucosides can be converted selectively into HMF in high yields, the process could become industrially viable and so the high‐yielding conversion of glucose into fructose is desirable.…”

Section: Conversion Of Carbohydrates In Water and Organic Solventsmentioning

confidence: 99%

“…), which additionally support the dehydration of fructose. [64][65][66] Despite an umber of examples demonstrating the successful conversion of fructosei nto HMF, [28,33,34,[67][68][69] most of them do not meet practical requirements,d ue to the high cost of the refined input carbohydrate substrates (mostly,f ructosea nd sucrose). If naturally abundant glucoseo rp olyglucosides can be converted selectively into HMF in high yields, the process Scheme2.Proposed mechanism for Lewis acid catalyzed glucose-fructose isomerization.…”

Section: Hmf and Its Derivativesmentioning

confidence: 99%

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Acid‐Catalyzed Conversion of Carbohydrates into Value‐Added Small Molecules in Aqueous Media and Ionic Liquids

2018

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Biomass is the only realistic major alternative source (to crude oil) of hydrocarbon substrates for the commercial synthesis of bulk and fine chemicals. Within biomass, terrestrial sources are the most accessible, and therein lignocellulosic materials are most abundant. Although lignin shows promise for the delivery of certain types of organic molecules, cellulose is a biopolymer with significant potential for conversion into high-volume and high-value chemicals. This review covers the acid-catalyzed conversion of lower value (poly)carbohydrates into valorized organic building-block chemicals (platform molecules). It focuses on those conversions performed in aqueous media or ionic liquids to provide the reader with a perspective on what can be considered a best case scenario, that is, that the overall process is as sustainable as possible.

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Section: Conversion Of Carbohydrates In Water and Organic Solventsmentioning

confidence: 99%

Section: Hmf and Its Derivativesmentioning

confidence: 99%

Acid‐Catalyzed Conversion of Carbohydrates into Value‐Added Small Molecules in Aqueous Media and Ionic Liquids

2018

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“…Common solid acid catalysts include carbon-based solid acids, molecular sieves, ion-exchange resins, and heteropoly acids [71]. Degradation of monosaccharide, starch, cellulose, and other biomasses to HMF using solid acid catalysts has been investigated ( Table 2) [72][73][74][75][76], but degradation of chitin biomass using solid acid catalysts has rarely been reported. Kalane et al [77] combined a solid acid catalyst with different concentrations of acetic acid to catalyze chitosan conversion to HMF by "green" synthesis.…”

Section: Hmf Production From Chitin Biomass By Lewis Acidsmentioning

confidence: 99%

Production of 5-Hydroxymethylfurfural from Chitin Biomass: A Review

Zhou

Shen

et al. 2020

Molecules

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Chitin biomass, a rich renewable resource, is the second most abundant natural polysaccharide after cellulose. Conversion of chitin biomass to high value-added chemicals can play a significant role in alleviating the global energy crisis and environmental pollution. In this review, the recent achievements in converting chitin biomass to high-value chemicals, such as 5-hydroxymethylfurfural (HMF), under different conditions using chitin, chitosan, glucosamine, and N-acetylglucosamine as raw materials are summarized. Related research on pretreatment technology of chitin biomass is also discussed. New approaches for transformation of chitin biomass to HMF are also proposed. This review promotes the development of industrial technologies for degradation of chitin biomass and preparation of HMF. It also provides insight into a sustainable future in terms of renewable resources.

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“…Notably, polyaniline (PAN) has recently received particular interest in catalytic applications as a heterogeneous organic support owing to its facile synthesis, air-stable performance, good dispersion of active species, and the pseudo-homogeneous character in organic solvents [20,[37][38][39][40][41][42][43][44]. In our group, we found that the functionalized PANs exhibited promising catalytic performance towards the dehydration of fructose into furans [45][46][47]. Considering the advantages and characteristics of PAN, we are expecting to incorporate the Mo-involved redox sites into the PAN "supports" such that the bifunctions of oxidation and dehydration could be combined, and even strengthened in a single inorganic-organic hybrid catalyst.…”

Section: Introductionmentioning

confidence: 97%

One-Pot Synthesis of 2,5-Diformylfuran from Fructose by Bifunctional Polyaniline-Supported Heteropolyacid Hybrid Catalysts

Liu

Dai

et al. 2019

Catalysts

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We report the preparation of bifunctional hybrid catalysts by supporting H3PMo12O40 (PMo12) heteropolyacid (HPA) on polyaniline (PAN) or formyl-functionalized PAN (F-PAN) for the “one-pot” and “one-step” synthesis of 2,5-diformylfuran (DFF) from fructose via 5-hydroxymethylfurfural (HMF) intermediate. We show that the PMo12 HPA is the main active species for both fructose dehydration and HMF oxidation owing to its Brønsted acidic and redox characters. However, the anchoring of PMo12 on PAN reduces the Brønsted acidity by acid–base interaction between protons in HPA and quinoid diimine structure in PAN, thereby reducing the dehydration performance. We demonstrate that the catalytic dehydration performance of the hybrid catalyst could be strengthened by grafting formyl groups on PAN before HPA anchoring. The highest DFF yield of 76.7% is obtained by conducting the “one-pot” reaction over the 40-PMo12/F3-PAN catalyst at 413 K for 7 h in air, wherein the side-reactions of fructose or HMF degradation and HMF rehydration have been significantly reduced. This hybrid catalyst is reusable without significant activity loss, highlighting the designing of stable inorganic–organic hybrid catalysts for producing valuable hexose-derived platform chemicals.

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Sulfonated polyaniline as a solid organocatalyst for dehydration of fructose into 5-hydroxymethylfurfural

Abstract: Sulfonated polyaniline with mutually reactive sulfonic acid groups and amine/imine represents an organocatalyst for effective production of 5-hydroxymethylfurfural (HMF) from carbohydrates in low-boiling solvents with complete restriction of HMF rehydration.

Cited by 72 publications

References 53 publications

Acid‐Catalyzed Conversion of Carbohydrates into Value‐Added Small Molecules in Aqueous Media and Ionic Liquids

Acid‐Catalyzed Conversion of Carbohydrates into Value‐Added Small Molecules in Aqueous Media and Ionic Liquids

Production of 5-Hydroxymethylfurfural from Chitin Biomass: A Review

One-Pot Synthesis of 2,5-Diformylfuran from Fructose by Bifunctional Polyaniline-Supported Heteropolyacid Hybrid Catalysts

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