Direct transformation of carbohydrates to the biofuel 5-ethoxymethylfurfural by solid acid catalysts

Li, Hu; Saravanamurugan, Shunmugavel; Yang, Song; Riisager, Anders

doi:10.1039/c5gc01043h

Cited by 162 publications

(94 citation statements)

References 65 publications

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“…This hypothesis, however; needs to be checked by synthesizing nanoparticles of different size and shape. The low EL yield on glucose ethanolysis is ascribed to the formation of ethyl-D-glucopyranoside (EDGP) due to the presence of Brønsted acid sites, as shown in the reaction scheme ( Figure-6) 138 . The low EL yield on glucose ethanolysis is ascribed to the formation of ethyl-D-glucopyranoside (EDGP) due to the presence of Brønsted acid sites, as shown in the reaction scheme ( Figure-6) 138 .…”

Section: Synthesis Of El From Monosaccharides and Polysaccharidesmentioning

confidence: 99%

“…The low EL yield on glucose ethanolysis is ascribed to the formation of ethyl-D-glucopyranoside (EDGP) due to the presence of Brønsted acid sites, as shown in the reaction scheme ( Figure-6) 138 . In general, EDGP isomerization to EDFF is a difficult step as compared to the dehydration reaction and is suggested to be rate-limiting 138 . In general, EDGP isomerization to EDFF is a difficult step as compared to the dehydration reaction and is suggested to be rate-limiting 138 .…”

Section: Synthesis Of El From Monosaccharides and Polysaccharidesmentioning

confidence: 99%

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Catalytic and mechanistic insights into the production of ethyl levulinate from biorenewable feedstocks

et al. 2016

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The importance of ethyl levulinate (EL) as a fuel additive and a potential biomassderived platform molecule is noteworthy. EL is obtained from the esterification of levulinic acid (LA) in presence of ethanol. Besides LA, the acid-catalyzed ethanolysis reaction to produce EL is carried out on a variety of biomass-derived substrates which include; furfuryl alcohol (FAL), chloromethyl furfural, monosaccharides, polysaccharides and lignocellulosic biomass. The acid catalysts employed for such conversions covers a wide range of structure and properties. The nature of acid catalysts and the key intermediates formed during the reaction dictates the overall yield of the desired product. For example, in the ethanolysis reaction of FAL to produce EL, diethyl ether (DEE) and ethoxymethylfuran (EMF) produced as side products are suggested to influence the selectivity of EL. Similarly, in the ethanolysis of glucose, formation of ethyl-Dglucopyranoside (EDGP) resulted into a slow conversion to produce EL. The review, therefore; is focused on highlighting the importance of catalyst structure, acidity, reaction mechanism and the role of key intermediates in the production of EL from biorenewable resources.EL could either be synthesized directly from biomass or via the transformation of LA, or FAL 20 or chloromethyl furfural (CMF) 23 . All of the suggested reaction routes essentially contain an ethanolysis step in the presence of an acid catalyst. In general, an understanding of the mechanistic routes of product formation, dictates the development of a suitable process for achieving higher yield 24,25 . This could be further strengthened by the design of a suitable homogeneous acid, solid acid or ionic liquid based acid catalysts. On catalytic processing, EL could be converted into an array of higher value chemicals. This review comprehensively covers all the suggested ways of EL production and applications detailing key mechanistic insights, catalytic properties and reaction conditions. Importance of EL as a Fuel AdditiveAlkyl levulinates have shown considerable promises for blending in gasoline and diesel engines, owing to their reduced sulfur content, high lubricity, improved flow properties and flash point stability 20 . The candidate LA esters for this application are methyl, ethyl 26 and butyl levulinates, 23 measuring anti-knocking index of value 106.5, 107.5 and 102.5 respectively 27 . Out of three levulinates, methyl levulinate (ML) is miscible with water and is difficult to separate. With gasoline, ML is lesser miscible and under cold flow conditions is not suitable to blend.Compared to butyl levulinate (BL), EL shows better solubility with diesel range fuels containing higher aromatics 14 . Moreover, NOx emissions were lowered by about 4% on EL blend in diesel as compared to the BL blend. Higher NOx emissions could be attributed to the dilution of lube oil and deposits in combustion chamber, which was observed to be a major problem with BL blended fuels. Furthermore, when propanol or higher alcohols are used for the...

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Section: Synthesis Of El From Monosaccharides and Polysaccharidesmentioning

confidence: 99%

Section: Synthesis Of El From Monosaccharides and Polysaccharidesmentioning

confidence: 99%

Catalytic and mechanistic insights into the production of ethyl levulinate from biorenewable feedstocks

et al. 2016

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“…By contrast, the transformation of glucose to EMF is much difficult owing to the demand of isomerization into fructose firstly, and the above developed catalysts had low reactivity. Presently, two combined catalyst systems consisting of zeolite and Amberlyst exhibited good catalytic activity for EMF synthesis from glucose [19,20]. Although significant advances have been made from persistent research, obstacles of using the heterogeneous catalysts include the complex preparation of the catalyst, expensive catalyst cost, and/or limited substrate adaptability.…”

Section: Introductionmentioning

confidence: 99%

Insights into the Metal Salt Catalyzed 5-Ethoxymethylfurfural Synthesis from Carbohydrates

Gao

Tao

et al. 2017

Catalysts

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Abstract:The use of common metal salts as catalysts for 5-ethoxymethylfurfural (EMF) synthesis from carbohydrate transformation was performed. Initial screening suggested AlCl 3 as an efficient catalyst for EMF synthesis (45.0%) from fructose at 140 • C. Interestingly, CuSO 4 and Fe 2 (SO 4 ) 3 were found to yield comparable EMF at lower temperature of 110 to 120 • C, and high yields of ethyl levulinate (65.4-71.8%) were obtained at 150 • C. However, these sulfate salts were inactive in EMF synthesis from glucose and the major product was ethyl glucoside with around 80% yield, whereas EMF of 15.2% yield could be produced from glucose using CrCl 3 . The conversion of sucrose followed the accumulation of the reaction pathways of fructose and glucose, and a moderate yield of EMF could be achieved.

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“…It could be speculated that the active sites of the catalyst partially covered by organic matter led to the decrease in the conversion. 50,51 Furthermore, FT-IR and XRD was carried out to fully understand the reasons of catalyst deactivation. Fig.…”

Section: Recyclability Of the Catalystsmentioning

confidence: 99%

Polyoxometalate-MgF₂hybrids as heterogeneous solid acid catalysts for efficient biodiesel production

et al. 2017

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A series of highly active and stable Keggin heteropolyacid catalysts were prepared through mixing of 12-tungstophosphoric acid (TPA) with magnesium fluoride (MgF 2 ). Among those acidic catalysts, the Mg 20 F 39 TPA-1.0 hybrid with moderate acidity (0.96 mmol g À1) and good dispersion of active sites presented pronounced catalytic performance in esterification of oleic acid (up to 95% oleic acid conversion). Particularly, Mg 20 F 39 TPA-1.0 was also efficient for the transesterification of Jatropha oil with a high acid value, giving biodiesel in 93% yield. Moreover, the catalyst showed good durability and reusability for at least five consecutive cycles.

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Direct transformation of carbohydrates to the biofuel 5-ethoxymethylfurfural by solid acid catalysts

Abstract: Biomass-based mono-, di- and polysaccharides are directly converted to the biofuel 5-ethoxymethylfurfural (EMF) in ethanol by solid acid zeolite catalysts or by a combined zeolite–Amberlyst catalyst system in a one-pot, two-step process.

Cited by 162 publications

References 65 publications

Catalytic and mechanistic insights into the production of ethyl levulinate from biorenewable feedstocks

Catalytic and mechanistic insights into the production of ethyl levulinate from biorenewable feedstocks

Insights into the Metal Salt Catalyzed 5-Ethoxymethylfurfural Synthesis from Carbohydrates

Polyoxometalate-MgF₂hybrids as heterogeneous solid acid catalysts for efficient biodiesel production

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Direct transformation of carbohydrates to the biofuel 5-ethoxymethylfurfural by solid acid catalysts

Abstract: Biomass-based mono-, di- and polysaccharides are directly converted to the biofuel 5-ethoxymethylfurfural (EMF) in ethanol by solid acid zeolite catalysts or by a combined zeolite–Amberlyst catalyst system in a one-pot, two-step process.

Cited by 162 publications

References 65 publications

Catalytic and mechanistic insights into the production of ethyl levulinate from biorenewable feedstocks

Catalytic and mechanistic insights into the production of ethyl levulinate from biorenewable feedstocks

Insights into the Metal Salt Catalyzed 5-Ethoxymethylfurfural Synthesis from Carbohydrates

Polyoxometalate-MgF2hybrids as heterogeneous solid acid catalysts for efficient biodiesel production

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Polyoxometalate-MgF₂hybrids as heterogeneous solid acid catalysts for efficient biodiesel production