Arylsulfonic acid functionalized hollow mesoporous carbon spheres for efficient conversion of levulinic acid or furfuryl alcohol to ethyl levulinate

Song, Daiyu; An, Sai; Lü, Bo; Guo, Yihang; Leng, Jinhua

doi:10.1016/j.apcatb.2015.05.047

Cited by 141 publications

(91 citation statements)

References 46 publications

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“…The alcoholysis of FAL to EL catalyzed by ZSM‐5 adopted the similar reaction pathway as reported in the previous mechanistic studies . With the catalysis of chitosan‐Ru, hydrogenation of the produced EL afforded 4‐HPs, which was further converted to GVL through the lactonization , …”

Section: Resultsmentioning

confidence: 99%

Production of γ‐Valerolactone from One‐Pot Transformation of Biomass‐Derived Carbohydrates Over Chitosan‐Supported Ruthenium Catalyst Combined with Zeolite ZSM‐5

Wang

Zhang

2020

Eur J Org Chem

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It remains as a challenge to directly transform the biomass‐derived C5 carbohydrates, such as furfural (FF) and its upstream product xylose and hemicellulose, to γ‐valerolactone (GVL), a versatile renewable chemical platform, due to various restrictions in the current synthetic strategies. Using formic acid as green hydrogen source, we synthesized the recyclable chitosan‐Ru/PPh3 catalyst system, effective for both the hydrogenation of FF to furfuryl alcohol (FAL) and the reduction of levulinic acid (LA) or ethyl levulinate (EL) to GVL, affording up to 99 % product yields. The combination of chitosan‐Ru/PPh3 with ZSM‐5 could successfully achieve up to 79 % yield of GVL from one‐pot conversion of FF under mild condition. Preliminary studies indicated that this method could also be applied to the direct conversion of biomass‐derived C5 carbohydrates such as xylose and hemicellulose to GVL in 37 % or 30 % yield, respectively.

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Section: Resultsmentioning

confidence: 99%

Production of γ‐Valerolactone from One‐Pot Transformation of Biomass‐Derived Carbohydrates Over Chitosan‐Supported Ruthenium Catalyst Combined with Zeolite ZSM‐5

Wang

Zhang

2020

Eur J Org Chem

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“…In addition, esterification reaction of LA to yield EL, leads to difficult product separation in aqueous phase. For example, Guo and co-workers have suggested 1,4 ethanol addition on EMF to produce EL as the major pathway 89,103 . EL produced can be upgraded to GVL 34,37 and this route, in-terms of obtained high yield, shows merit over the direct LA 13 conversion to GVL.…”

Section: Synthesis Of El From Falmentioning

confidence: 99%

“…In addition, sulfonated acid catalysts are observed to be thermally stable 89 . This problem could be resolved by having hydrophobic sulfur complexes on the surface of the metal oxide.…”

Section: Introductionmentioning

confidence: 99%

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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“…However, extremely strong Brønsted acid sites lead to the formation of oligomeric condensation products of FAL, such as homogenous H 2 SO 4 or benzenesulfonic acid. Thus, the Brønsted acid density should be controlled at an appropriate level (e.g., 4800 μequiv

_{normalH^{+}}

per gram of Amberlyst) ,…”

Section: Alcoholysis Of Furfuryl Alcohol To Alkyl Levulinatementioning

confidence: 99%

Alcoholysis: A Promising Technology for Conversion of Lignocellulose and Platform Chemicals

et al. 2017

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In the catalytic conversion of lignocellulose to valuable products, the first entry point is to break down these biopolymers to sugar units or aromatic monomers, which is conventionally achieved by hydrolysis in water medium. Recent years have seen tremendous progress in the alcoholysis process, which has remarkable advantages, such as the avoidance of treating waste water, suppression of humins or chars, and enhancement of reaction rate and product yield. Advances have been focused on the alcoholysis of cellulose, hemicellulose, and lignin to alkyl glucosides, xylosides, and aromatic monomers, respectively. Alcoholysis of the platform molecule furfuryl alcohol (FAL) to alkyl levulinate (AL) and integrated alcoholysis of cellulose and furfural into AL are also summarized. This Minireview highlights the comparisons between alcoholysis and hydrolysis, the reaction mechanism of alcoholysis, and future challenges for industrial applications.

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Arylsulfonic acid functionalized hollow mesoporous carbon spheres for efficient conversion of levulinic acid or furfuryl alcohol to ethyl levulinate

Cited by 141 publications

References 46 publications

Production of γ‐Valerolactone from One‐Pot Transformation of Biomass‐Derived Carbohydrates Over Chitosan‐Supported Ruthenium Catalyst Combined with Zeolite ZSM‐5

Production of γ‐Valerolactone from One‐Pot Transformation of Biomass‐Derived Carbohydrates Over Chitosan‐Supported Ruthenium Catalyst Combined with Zeolite ZSM‐5

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

Alcoholysis: A Promising Technology for Conversion of Lignocellulose and Platform Chemicals

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