Levulinic acid, esterification

Fernandes DR, Rocha AS, Mai EF, Mota CJA, Teixeira da Silva V (2012) Levulinic acid esterification with ethanol to ethyl levulinate production over solid acid catalysts. Appl Catal A Gen 425 26 199-204... 

Another interesting HMF-derived compound is levulinic acid formed together with formic acid by solid acid catalysis. A one-pot cascade route from c.g. inulin seems feasible. Manzer et al. [37] give examples in which an esterification step with an alkene is coupled as well. The... 

Esterification, crotonic acid, 149 levulinic acid, 157 thiophene-2-carboxylic acid, 182 o-toluic acid, 162 Ester interchange, 152 Ethanolysis of ethyl iminoacetate, 159 Ether cleavage with HBr, 271... 

Carboxylation of levulinic acid. Carboxylation of levulinic acid (1) with MMC in DMF at 135° for 24 hr. followed by esterification affords dimethyl 3-ketoadipate (2) in 92% yield. ... 

Bart HJ, Reidetschlager J, Schatka K, Lehmann A (1994) Kinetics of esterification of levulinic acid with n-butanol by homogeneous catalysis. Ind Eng Chem Res 33 21-25... 

Maheria KC, Kozinski J, Dalai A (2013) Esterification of levulinic acid to n-butyl levulinate over various acidic zeolites. Catal Lett 143 1220-1225... 

Kinetics models for esterification of levulinic acid with 2-ethylhexanol using different catalysts... 

The kinetics of the esterification of levulinic acid with 2-ethylhexanol in the presence of the various catalyst has been investigated in an experimental, isothermal semibatch reactor. The kinetic equations and dieir parameters have been determined. 

Levulinic esters may be obtained by esterification of levulinic acid with suitable alcohols CH3-CO-CH2-CH2COOH + ROH =>CH3-C0-CH2-CH2C00R + H2OI... 

The reaction kinetics of levulinic acid with aliphatic alcohols is not sufficiently known. In general only Bart et al. [1] gave kinetic information concerning the esterification of levulinic acid with n-butyl alcohol in a presence of sulphuric acid as a catalyst. Their experiments were concerned with a reversible process, and kinetic equations obtained by them correspond to a second order reaction. 

Since the Bart s research [1] was limited to one selected catalyst, it seemed reasonable to widen the work to other catalyst used in industry. The goal of this work was to learn about the kinetics of esterification of levulinic acid with 2-ethylhexanol using different catalysts, based on wide range of experiments in a semibatch reactor. 

The selectivity of examined esterification reaction of levulinic acid with 2-ethylhexanol was very high. Chromatographic evaluation of randomly selected samples of a reaction mixture has shown only trace amounts of ethers, which are products of alcohol dehydration. 

Levuhnic acid is one of the products of selective dehydration of cellulosic biomass feedstocks. Levuhnic acid is produced when six-member ring carbohydrates derived from ceUulose are subjected to acid-catalyzed dehydration conditions (Fig. 9.6) [4, 43]. The other main product of this reaction is formic acid. Although levulinic acid has some potential use as a solvent or in the production of industrial and pharmaceutical chemicals, its current market is minimal [4]. Therefore, the conversion of levulinic acid to a directly usable biofuel has become an important area of interest. In particular, esterification, oxidation, hydrogenation, reductive amination, condensation, and enzymatic conversion have been tested as potential methods to produce useful compounds from levulinic acid [4,44,45]. 

Low-alkyl levulinates, and particularly ethyl levulinate (EL), can be advantageously used as oxygenated biofuels. They can be easily obtained by esterification of levulinic acid with a lower alcohol such as ethanol. Such reaction occurs even at room temperature, but the rate is very low and needs to be accelerated by either increasing... 

Intrinsic energy of FA can also be upgraded by means of etherification with short-chain alcohols, transformation of alkyl-furfuryl ethers into alkyl levulinates and esterification with short alkyl carboxylic acids. In the following, we wiU discuss the most... 

Kuwahara, Y., Kaburagi, W., Nemoto, K., Fujitani, T., 2014. Esterification of levulinic acid with ethanol over sulfated Si-doped Z1O2 sobd acid catalyst study of the structure—activity relationships. Catalysis Today 237, 18—28. 

Sen, SJVI., Giirbiiz, E.I., Wettstein, S.G., Martfn-Alonso, D., Dumesic, J.A., Maravelias, C.T., 2012b. Production of butene oligomers as transportation fuels using butene for esterification of levulinic acid from lignocellulosic biomass process synthesis and technoeconomic evaluation. Green Chemistry 14, 3289—3294. 

Alkyl levulinate esters 72 can be prepared by homogeneous acid-catalyzed Fischer esterification of LA [188], under solid acid catalysis [189, 190], by acid-catalyzed... 

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