Preparation of 5-methylfurfural from starch in one step by iodide mediated metal-free hydrogenolysis

Yang, Peng; Li, Xianghua; Gao, Tian; Li, Teng; Yang, Weiran

doi:10.1039/c9gc01645g

Cited by 44 publications

(31 citation statements)

References 45 publications

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“…Peng et al developed a novel one-pot metal-free strategy to synthesize 5MF from starch using HCl and NaI in the presence of H 2 . The method described above gave an 80.8% yield of 5MF starting from HMF in a biphasic system [152]. The utilization of polyvinylpyrrolidone as a capping agent for Pd NPs increased the 5MF selectivity up to 90%.…”

Section: Hmf To 5mfmentioning

confidence: 98%

Energy Densification of Biomass-Derived Furfurals to Furanic Biofuels by Catalytic Hydrogenation and Hydrodeoxygenation Reactions

Vinod¹,

Dutta²

2021

Sustainable Chemistry

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The concomitant hydrolysis and dehydration of biomass-derived cellulose and hemicellulose to furfural (FUR) and 5-(hydroxymethyl)furfural (HMF) under acid catalysis allows a dramatic reduction in the oxygen content of the parent sugar molecules with a 100% carbon economy. However, most applications of FUR or HMF necessitate synthetic modifications. Catalytic hydrogenation and hydrogenolysis have been recognized as efficient strategies for the selective deoxygenation and energy densification of biomass-derived furfurals generating water as the sole byproduct. Efficient and eco-friendly catalysts have been developed for the selective hydrogenation of furfurals affording renewable furanic compounds such as 2-methylfuran, 2,5-dimethylfuran and 2-methyltetrahydrofuran with potential applications as biofuel, solvent and chemical feedstock. Hydrogen gas or hydrogen donor molecules, required for the above processes, can also be renewably obtained from biomass using catalytic processes, enabling a circular economy. In this review, the recent developments in the energy densification of furfurals to furanic compounds of commercial significance are elaborated, emphasizing the role of catalyst and the reaction parameters employed. Critical discussion on sourcing hydrogen gas required for the processes, using hydrogen donor solvents, catalyst design and the potential markets of furanic intermediates have been made. Critical evaluations of the accomplishments and challenges in this field are also provided.

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Section: Hmf To 5mfmentioning

confidence: 98%

Energy Densification of Biomass-Derived Furfurals to Furanic Biofuels by Catalytic Hydrogenation and Hydrodeoxygenation Reactions

Vinod¹,

Dutta²

2021

Sustainable Chemistry

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“…Based on the properties and experimental studies of Sn x PW, a possible catalytic mechanism is proposed (Peng et al, 2019), which primarily can be divided into three steps, as shown in Scheme 2: first, starch molecules are hydrolyzed under acidic conditions to break the glycosidic bond and produce glucose; second, glucose is isomerized to fructose; finally, the fructose molecules undergo a dehydration reaction and shed three water molecules to form HMF. In the second process, Snn + electrophilically attacks glucose molecules and acts on the oxygen atom of the aldehyde group to form an intermediate, which then isomerizes to fructose.…”

Section: Catalytic Mechanismmentioning

confidence: 99%

Catalytic Conversion of Starch to 5-Hydroxymethylfurfural by Tin Phosphotungstate

et al. 2021

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Heteropoly acids containing Brønsted and Lewis acids show excellent catalytic activity. Brønsted acids promote the depolymerization of polysaccharides (such as starch and cellulose) into glucose, while Lewis acids catalyze the conversion of glucose to 5-hydroxymethylfurfural (HMF). Designing stable Brønsted-Lewis acid-containing bifunctional heterogeneous catalysts is crucial for the efficient catalytic conversion of polysaccharides to HMF. In this study, a series of Brønsted -Lewis acid bifunctional catalysts (SnxPW, X = 0.10–0.75) were investigated for the conversion of cassava starch to HMF. The structure of the catalysts was characterized by X-ray diffraction, Fourier transform infrared spectroscopy, Pyridine Fourier transform infrared spectroscopy, and X-ray photoelectron spectroscopy. The acid strength and acid capacity were also investigated. The effects of reaction time, temperature, catalyst concentration, and cassava starch concentration on the selectivity, conversion rate, and yield were examined. The results showed that, among the analyzed catalysts, Sn0.1PW presented the best ability under the test conditions for catalyzing the conversion of starch to HMF. At the optimized conditions of a reaction temperature of 160°C, a catalyst dosage of 0.50 mmol/gstarch, and a 1 h reaction time, the starch conversion rate was 90.61%, and the selectivity and yield of HMF were 59.77 and 54.12%, respectively. Our findings contribute to the development of HMF production by the dehydration of carbohydrates.

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“…[7,8,9,10] On the other hand, many works are also devoted to the access of furaldehyde derivatives such as 5-hydroxymethylfurfural (HMF) from biomass derived carbohydrates for the development of new generation of biofuels or as renewable raw materials for chemistry in pharmaceutical or materials chemistry. [11,12,13,14] Over the last decade, works about furan-based conjugated derivatives brought out relevant benefits of the furan cycle for the development of semi-conducting materials for optoelectronic devices. [15,16,17,18] The insertion of low aromaticity cycle such as furan into a conjugated chain allows to increase the rigidity and the planarity of the structure and thus to enhance the electronic delocalization along the conjugated systems.…”

Section: Introductionmentioning

confidence: 99%

“…Lignin is a very important sustainable feedstock strongly worked for the development of methoxy‐benzaldehyde derivatives such as vanillin and syringaldehyde [7,8,9,10] . On the other hand, many works are also devoted to the access of furaldehyde derivatives such as 5‐hydroxymethylfurfural (HMF) from biomass derived carbohydrates for the development of new generation of biofuels or as renewable raw materials for chemistry in pharmaceutical or materials chemistry [11,12,13,14] . Over the last decade, works about furan‐based conjugated derivatives brought out relevant benefits of the furan cycle for the development of semi‐conducting materials for optoelectronic devices [15,16,17,18] .…”

Section: Introductionmentioning

confidence: 99%

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Exploring the Electronic Properties of Extended Benzofuran‐Cyanovinyl Derivatives Obtained from Lignocellulosic and Carbohydrate Platforms Raw Materials

et al. 2021

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Two series of linear extended benzofuran derivatives associating cyanovinyl unit and phenyl or furan moieties obtained from benzaldehyde-lignocellulosic (Be series) or furaldehyde-saccharide (Fu series) platforms were prepared in order to investigate their emission and electrochemical properties. For the fluorescence in solution and solid states, contrasting results between the two series were demonstrated. For Be series a net aggregation induced emission effect was observed with high fluorescence quantum yield for the solid state. A [2 + 2] cycloaddition under irradiation at 350 nm was also revealed for one derivative of Be series. In contrast, for Fu series the fluorescence in solution is higher than in the solid state. The X-ray crystallography studies for the compounds reveal the formation of strong π-π stacking for the derivatives without emissive property in the solid state and the presence of essentially lateral contacts for emissive compounds. Taking advantage of the propensity to develop 2D π-stacking mode for the more extended derivative with a central furan cycle, organic field effect transistors presenting hole mobility have been made.

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Preparation of 5-methylfurfural from starch in one step by iodide mediated metal-free hydrogenolysis

Abstract: Starch is available in large quantities and at cheap price, especially that from stale rice, root and tuber crops, etc. A metal-free approach to convert starch to 5-methylfurfural using HCl, NaI and H2 in a biphasic solvent system has been developed.

Cited by 44 publications

References 45 publications

Energy Densification of Biomass-Derived Furfurals to Furanic Biofuels by Catalytic Hydrogenation and Hydrodeoxygenation Reactions

Energy Densification of Biomass-Derived Furfurals to Furanic Biofuels by Catalytic Hydrogenation and Hydrodeoxygenation Reactions

Catalytic Conversion of Starch to 5-Hydroxymethylfurfural by Tin Phosphotungstate

Exploring the Electronic Properties of Extended Benzofuran‐Cyanovinyl Derivatives Obtained from Lignocellulosic and Carbohydrate Platforms Raw Materials

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