ETHANOLAMINE AND PENTYL ACETATE INTERACTION CATALYZED BY CATION EXCHANGE RESIN: KINETIC INSIGHT
Keywords:ethanolamine; pentyl acetate; N-(2-hydroxyethyl)acetamide; 2-aminoethyl acetate; 2-(acetylamino)ethyl acetate; kinetic; aminolysis; transesterification; cation exchange resin
We report the scheme of ethanolamine, pentyl acetate, and their interaction products in transesterification, aminolysis, and O-N-acyl migration reactions catalyzed by H-cation exchange resin. The routes of N-(2-hydroxyethyl)acetamide, 2-aminoethyl acetate, and 2-(acetylamino)ethyl acetate formation indicate that N-(2-hydroxyethyl)acetamide is the final product. The determined rate constant values for the proposed quasi-homogeneous reaction model indicate the significant role of aminolysis reaction by ethanolamine and pentyl acetate interaction catalyzed by H-cation exchange resin. In particular, high values of the rate constant of aminolysis reactions indicate a high rate of amide formation during the interaction of ethanolamine and pentyl acetate, 2-aminoethyl acetate, or 2-(acetylamino)ethyl acetate. The proposed kinetic model adequately describes the N-(2-hydroxyethyl)acetamide obtaining process from ethanolamine and pentyl acetate. The values of the considered reactions' pre-exponential factors, rate constants, energy activation, entropy and enthalpy activation were calculated. In particular, the reaction of N-(2-hydroxyethyl)acetamide formation by aminolysis of pentyl acetate with ethanolamine has the lowest activation energy (15.8 kJ∙mol–1), and the reaction of 2-(acetylamino)ethyl acetate formation by N-(2-hydroxyethyl)acetamide with pentyl acetate transesterification has the highest activation energy (89.1 kJ∙mol–1). A linear relationship was revealed between the pre-exponential factor logarithms of reaction rate constants and activation energies and between the enthalpy and entropy activation. We assume the compensatory effect and the absence of an isokinetic relationship for the entire set of reactions. The study results are the basis for modeling the N-(2-hydroxyethyl)acetamide obtaining process from ethanolamine and pentyl acetate.
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