Advances in the Catalytic Production of Valuable Levulinic Acid Derivatives

doi:10.1002/cctc.201200113

Paper

Advances in the Catalytic Production of Valuable Levulinic Acid Derivatives

Published Sep 1, 2012 · Jun Zhang, Shubin Wu, Bowen Li

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Abstract

Currently, the conversion of biomass to levulinic acid and its derivatives has been one of the hottest topics in the field of energy and resources, because it opens up a new avenue for achieving sustainable energy supply and chemicals production. Levulinic acid can be used as a platform chemical for the production of a wide range of value-added compounds, such as levulinate esters and g-valerolactone. This review mainly discusses the catalytic routes for synthesis of valuable levulinate esters and g-valerolactone under different efficient reaction systems. Meanwhile, some promising and valuable researching directions and effective catalysts are suggested based on the major challenges emerged in recent studies. With the gradual depletion of fossil resources and further deterioration of the environment and its ecosystem, abundant renewable biomass are regarded as a promising alternative to non-renewable natural resources for the sustainable production of biofuels and biochemicals in the future (Figure 1). Recently, extensive research has been performed worldwide to identify and study chemical or biological transformations for converting biomass into fuels and raw chemicals. Among these explorations, one attractive approach is the preparation and conversion of levulinic acid (LA), owing to its importance as one of the 12 important target chemicals that US-DOE selected in their biomass program. It is widely used in food, agriculture, drugs, cosmetics, spice industries, as well as its derivatives. With regard to sources of LA, the LA preparation method can be classified into two categories according to the raw material resources, based on previous studies, namely, furfuralcohol hydrolysis and biomass conversion. Both of these two methods were conducted under acidic conditions or with acid catalysts, while the materials including starch and cellulose were used as the reactant for method of biomass conversion. Besides, high purity, LA can be obtained by furfuralcohol hydrolysis with a suitable solvent and catalyst. Considerable research over the past years has focused on the catalytic conversion of biomass into LA by both batch processes and continuous technology. As for transformation pathways, if agricultural and forest wastes can be rationally utilized, many valuable chemicals can be created at the same time. Most importantly of all, it opens a new way for the production of biochemicals in an economical manner. Many kinds of raw materials such as lignocellulose, corn starch, and discarded cellulose are used extensively in this route. However, there still are some clear shortcomings, especially as the apparent LA yield is not high and the final reaction products are complicated. In subsequent research, glucose has also been adopted as a raw material to yield LA, and a desired yield of LA can be obtained with solid acids as catalyst. As the studies develop in depth, some valuable levulinic acid derivatives have been discovered by researchers in recent years, especially levulinate esters and g-valerolactone. As these compounds are widely applied in food and chemical industry, it is of great significance for us to do more research on the preparation of the above high value-added chemicals by means of heterogeneous or homogeneous reaction. The levulinate esters were produced by the esterification of LA between alcohols, such as methanol, ethanol, and butanol under acidic conditions. Meanwhile, g-valerolactone (GVL) is a selective hydrogenation and dehydration product of LA catalyzed by metal catalysts. Clearly, it is a research direction with great significance and many researchers are now working on this new aspect. Currently, there is no review of the catalytic preparation of levulinate esters and GVL to date. Given that the rapid progress on the catalytic conversion of biomass, this minireview mainly concentrates on describing the work reported over the last few years. Basic information about levulinic acid is given,

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Catalytic conversion of biomass into levulinic acid and its derivatives offers a promising sustainable energy supply and chemicals production solution, with potential for use in food, agriculture, and pharmaceutical industries.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Advances in the Catalytic Production of Valuable Levulinic Acid Derivatives

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References

Catalytic upgrading of levulinic acid to ethyl levulinate using reusable silica-included Wells-Dawson heteropolyacid as catalyst

Silica-included Wells-Dawson heteropolyacids are active and selective catalysts for the esterification reaction of levulinic acid and ethanol to ethyl levulinate, maintaining their structure and activity after three consecutive reaction cycles.

Solid acid catalysed formation of ethyl levulinate and ethyl glucopyranoside from mono- and disaccharides

The SO 3 H-SBA-15 catalyst effectively converts fructose to ethyl levulinate (57%), glucose to EDGP (80%) at 140°C, outperforming zeolites under identical reaction conditions.

Conversion of carbohydrates biomass into levulinate esters using heterogeneous catalysts

Sulfated metal oxides (SO 4 2 - /TiO 2 ) show high selectivity and yield of methyl levulinate from carbohydrates, with potential for environmentally benign conversion and reusability.

Hydrogen-independent reductive transformation of carbohydrate biomass into γ-valerolactone and pyrrolidone derivatives with supported gold catalysts.

This study successfully developed a reusable solid catalyst for base-free g-valerolactone production from biomass hydrolysis, reducing energy consumption and processing costs while maintaining a sustainable process.

Levulinic esters from the acid-catalysed reactions of sugars and alcohols as part of a bio-refinery

Protecting reactive functional groups of sugars and reaction intermediates through acetalisation and etherification in methanol medium effectively suppresses humin formation and enhances levulinic ester production in bio-refineries.

Production of liquid hydrocarbon fuels by catalytic conversion of biomass-derived levulinic acid

The RuRe/C catalyst effectively converts biomass-derived levulinic acid to -valerolactone, offering a cost-effective route for converting ligno-cellulosic biomass to liquid hydrocarbon fuels.

Ethyl levulinate: a potential bio-based diluent for biodiesel which improves cold flow properties.

Ethyl levulinate improves cold flow properties in biodiesel fuels with high saturated fatty acid content, but does not significantly affect acid value or oxidative stability.

Experimental and kinetic modeling studies on the biphasic hydrogenation of levulinic acid to γ-valerolactone using a homogeneous water-soluble Ru–(TPPTS) catalyst

Biphasic hydrogenation of levulinic acid to -valerolactone using a water-soluble Ru-(TPPTS) catalyst produces quantitative GVL yields at 45 bar, 90°C, and 80 min reaction time, with a recyclable catalyst.

Citations

Zirconium-Containing Metal–Organic Frameworks (MOFs) as Catalysts for Biomass Conversion

Zr-containing metal-organic frameworks (MOFs) UiO-66 and MOF-808 show potential as catalysts for converting biomass-derived products into valuable chemicals, with their chemical properties varying based on their hydration state and biomass source.

Impact of steric hindrance in levulinic acid esterification to levulinate esters: kinetic and thermodynamic studies

Increasing alcohol alkyl chain length and branching decreases the rate of levulinate ester formation, likely due to steric effects and larger structural rearrangements.

Metal-Exchanged Phosphomolybdic Acid Salts-Catalyzed Esterification of Levulinic Acid

Metal-exchanged phosphomolybdic acid salts, specifically iron and aluminum, are effective catalysts for converting levulinic acid into valuable alkyl levulinate, offering a promising alternative to traditional soluble and corrosive Brnsted acid catalysts.

Hydrothermal liquefaction for producing liquid fuels and chemicals from biomass-derived platform compounds: a review

Hydrothermal liquefaction of biomass-derived platform compounds offers potential for sustainable fuel production by converting complex organic materials into valuable liquid products.

Utilizing environment-friendly eugenol as a diluent with trioctylamine for the reactive extraction of aqueous levulinic acid

Eugenol, a green alternative, is a suitable diluent for reactive extraction of aqueous levulinic acid, with MeOH also showing potential as a diluent.

Extraction of Levulinic Acid from Aqueous Solution Using Trioctylamine at Different Temperatures

Trioctylamine effectively separates levulinic acid from aqueous solutions, with higher extraction efficiencies possible at higher acid concentrations.

Metal-organic frameworks as potential catalysts for biodiesel production and biomass conversion: Mechanism and characteristics

Metal-organic frameworks (MOFs) show potential as catalysts for biomass conversion and biodiesel production, offering versatile performance attributes and promoting green chemistry practices.

Direct methanol oxygen-ion conducting solid oxide fuel cell with an integrated in-situ cracking reactor

This study developed a novel cell design with an in-situ cracking reactor, enhancing power generation performance and stability in oxygen-ion conducting solid oxide fuel cells powered by methanol.

Conversion of Biomass-Derived Molecules into Alkyl Levulinates Using Heterogeneous Catalysts

Heterogeneous catalysts with various strategies can efficiently convert biomass-derived molecules into alkyl levulinates, providing valuable products for fuel additives, flavoring agents, and fragrances.