A combined experimental and computational study of the esterification reaction of glycerol with acetic acid

Abstract

This work describes theoretical and experimental studies on glycerol esterification to obtain acetins focusing on the obtained isomers. The reaction of glycerol with acetic acid was carried out on Amberlyst 36 wet. Density functional theory calculations on the level of M06-2X functional and 6-311+G(d,p) basis set are carried out and the most stable structures of the reactants and products are located by considering a large number of conformers. The thermodynamics is discussed in terms of the calculated reaction Gibbs free energy. The AIM theory was used to characterize reactants and products. The glycerol esterification with acetic acid is found to be thermodynamically favored, with exothermal property. These agree well with experiments and allow us to explain the relative selectivity of products.

A fully bio‐based monomer derived from undecylenic acid, glycerol, and CO2 useful for the synthesis of polyhydroxyurethanes

“…Thus, the carboxylic acid is activated toward a nucleophilic attack from the glycerol. Then, the reaction continues with water elimination, and the ester is formed 23 . The esterification reaction between glycerol and UA can produce mono‐, di‐, and triglycerides 24 .…”

“…Then, the reaction continues with water elimination, and the ester is formed. 23 The esterification reaction between glycerol and UA can produce mono-, di-, and triglycerides. 24 An excess of UA and a high temperature were used to favor the production of triglyceride product.…”

Esterification of Succinic Acid Using Sulfated Zirconia Supported on SBA‐15

“…It is widely accepted that Brønsted acid sites catalyze esterification reactions. Accordingly, ion‐exchange resins are the most commonly used catalysts and have been proved to be effective in liquid‐phase esterification reactions 61–63. However, the yield data shown in Fig.…”

Enhanced recovery and recycling of catalyst by post‐impregnation of γ‐Al2O3 with 12‐tungstophosphoric acid for esterification reaction

“…The proton of the catalyst attaches to the lone pair of oxygen of the carbonyl group. The carbon which is double‐bonded to oxygen gets a partially positive charge . A tetrahedral intermediate is produced by nucleophilic attack of 1‐hexanol to the carbocation.…”