Kinetics of esterification of succinic anhydride with methanol by homogeneous catalysis

Abstract

Kinetic data on the esterification of succinic anhydride with methanol catalyzed by sulfuric acid have been obtained using a stirred batch reactor. In addition to get a precise ascertainment of the parameters the esterification of monomethyl succinate with methanol has been studied separately. Several experiments have been carried out with different initial molar ratios and different amounts of sulfuric acid at various temperatures. The conversion to dimethyl succinate at 30-65°C follows a first-order rate expression with respect to each component. A theoretical rate equation is derived by the following reaction mechanism:(1) succinic anhydride is protonated by sulfuric acid to form a reaction intermediate, (2) irreversible esterification to monomethyl succinate, (3) protonation of the monoester, and (4) the esterification to dimethyl succinate proceeds reversibly. The resultant kinetic equation fitted the experimental data quite well and is given by the expression:

Mono-substitution of symmetric diesters: selectivity of Mycobacterium smegmatis acyltransferase variants

“…For acids that are able to form 5-or 6-membered cyclic anhydrides, monoacylation is possible. 3,4 For other diacids both chemical and biocatalytic methods to form mono-esters have been developed. [5][6][7][8][9] All these methods lead to dicarboxylic acid derivatives with both acid and ester functionalities, i.e.…”

Kinetic Study and Model Assessment for n-Butyl Levulinate Production from Alcoholysis of 5-(Hydroxymethyl)furfural over Amberlite IR-120

“…The values of the estimated constants as well as the credible intervals are given in Tables S2.1 and S2.2 (Supporting Information (S2)). In Table S2.3, the estimated activation energies obtained from this work and found in literature − are displayed. It is not possible to compare the activation energies, because solvent/reactant and proposed models by other authors (reaction rate expression) were not the same.…”

“…Some kinetic models of sugar hydrolysis to levulinic acid and esterification (levulinic acid to alkyl levulinates and formic acid to alkyl formate) can be found in the literature. ,− However, the development of kinetic models for the alcoholysis of sugars to alkyl levulinates is scarce, and the kinetic constant comparison is difficult due to the different ways to derive reaction rates . The kinetic modeling of this system is complex because several reactions occur simultaneously in parallel and consecutive ways (Figure ).…”

Towards a Bio‐Based Industry: Benign Catalytic Esterifications of Succinic Acid in the Presence of Water

“…[8][9][10][11] Many acid catalysts have been reported in these reactions, [12] although only a few authors have dealt with the esterifica- tion of either succinic acid [13] or its cyclic anhydride. [14] The esterification reaction has been reported as being very sensitive to water environments due to different equilibrium steps in which water is involved (Scheme 1). [15] Water has been proved to affect the reaction activity, in homogeneous conditions, [14b, 16a] resulting in a decrease of the rate of esterification that has generally been attributed not only to reverse hydrolysis but also to a competitive protonation step involving the water and the alcohol (assuming the rate-determining step is the interaction between the protonated alcohol and the carboxylic acid).…”