Mechanism of levulinic acid formation

Horvat, Jaroslav; Klaić, Branimir; Metelko, Biserka; Šunjić, Vitomir

doi:10.1016/s0040-4039(00)94793-2

Cited by 283 publications

(268 citation statements)

References 7 publications

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“…16 Additionally, pentoses such as xylose, the main component of the hemicellulose fraction, can be converted to levulinic acid. In this case the process involves the dehydration of xylose to furfural, subsequent hydrogenation to furfuryl alcohol which is finally hydrolyzed to levulinic acid (Scheme 1).…”

Section: Levulinic Acid As Platform For Fuel Additives and Liquid Hydmentioning

confidence: 99%

“…and in some cases in combination with the adjustment of the molecular weight via C-C coupling reactions (e.g aldolcondensation, ketonizacion, oligomerizatión) of reactive intermediates. These C-C coupling reactions are especially important when starting from biomass derivatives with C 5 -C 6 carbons (derived from monosacharides) and the final products are hydrocarbon fuels to be used in diesel engines (C 10 -C 20 ) and jets (C 9 -C 16 ).…”

Section: Introductionmentioning

confidence: 99%

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Conversion of biomass platform molecules into fuel additives and liquid hydrocarbon fuels

2014

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In this work some relevant processes for the preparation of liquid hydrocarbon fuels and fuel additives from cellulose, hemicellulose and triglycerides derived platform molecules are discussed. Thus, it is shown that a series of platform molecules such as levulinic acid, furans, fatty acids and polyols can be converted into a variety of fuel additives through catalytic transformations that include reduction, esterification, etherification, and acetalization reactions. Moreover, we will show that liquid hydrocarbon fuels can be obtained by combining oxygen removal processes (e.g. dehydration, hydrogenolysis, hydrogenation, decarbonylation/descarboxylation etc.) with the adjustment of the molecular weight via C-C coupling reactions (e.g. aldol condensation, hydroxyalkylation, oligomerization, ketonization) of the reactive platform molecules.

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Section: Levulinic Acid As Platform For Fuel Additives and Liquid Hydmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Conversion of biomass platform molecules into fuel additives and liquid hydrocarbon fuels

2014

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“…Elevated temperatures and aqueous reaction environment make the dehydration reaction steps thermodynamically more favorable. A proposed rehydration mechanism of 5-HMF into LA in acid environment is reported in Figure 2 [29]. Antal et al proposed that 5-HMF is produced from fructose via cyclic intermediates [19].…”

Section: Introductionmentioning

confidence: 99%

“…Elevated temperatures and aqueous reaction environment make the dehydration reaction steps thermodynamically more favorable. A proposed rehydration mechanism of 5-HMF into LA in acid environment is reported in Figure 2 [29]. Hydration of 5-HMF consists in the addition of a water molecule to the C2-C3 olefinic bond of the furan ring, leading to an unstable tricarbonyl intermediate, which quickly decomposes to LA and formic acid (HCOOH), in stoichiometric amount [22,30].…”

Section: Introductionmentioning

confidence: 99%

New Frontiers in the Catalytic Synthesis of Levulinic Acid: From Sugars to Raw and Waste Biomass as Starting Feedstock

et al. 2016

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Levulinic acid (LA) is one of the top bio-based platform molecules that can be converted into many valuable chemicals. It can be produced by acid catalysis from renewable resources, such as sugars, lignocellulosic biomass and waste materials, attractive candidates due to their abundance and environmentally benign nature. The LA transition from niche product to mass-produced chemical, however, requires its production from sustainable biomass feedstocks at low costs, adopting environment-friendly techniques. This review is an up-to-date discussion of the literature on the several catalytic systems that have been developed to produce LA from the different substrates. Special attention has been paid to the recent advancements on starting materials, moving from simple sugars to raw and waste biomasses. This aspect is of paramount importance from a sustainability point of view, transforming wastes needing to be disposed into starting materials for value-added products. This review also discusses the strategies to exploit the solid residues always obtained in the LA production processes, in order to attain a circular economy approach.

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“…This translates to the conversion of approximately 50% of the mass of 6-carbon sugars to LA, with 20% being converted to formic acid and 30% being incorporated in the residual "char" material which also contains all of the Klason lignin and the 50%, by mass, of pentoses that do not convert to furfural. Previously developed technologies that attempted to produce LA from lignocellulosics had high costs due to low LA yields (around 3% by mass) and significant tar formation due to the complexity of the glucose to LA pathway [64,66,67]. These yield claims have been supported by data from two pilot plants in the US, where various feedstocks, including agricultural residues, paper sludges, and the organic fraction of municipal waste have been processed [68], as well as by a 50 tonne per day commercial facility that is being commissioned in Caserta, Italy and will process waste paper, municipal wastes and agricultural residues.…”

Section: The Biofine Processmentioning

confidence: 99%