Kinetics and quantum chemical aspects of the mechanism of the guanidine (TBD) catalyzed aminolysis of cyclocarbonate containing soybean oil triglycerides as the model process of green chemistry of polyurethanes

Abstract

The kinetic regularities and the mechanism of the catalytic action of 1,5,7-triazabicyclo[4.4.0]decene-5 (TBD) in the reaction of n-butylaminolysis of cyclocarbonate-containing triglyceride based on soybean oil in DMSO have been studied. It is shown via DFT quantum chemical calculations of the model reaction of ethylene carbonate with methylamine under the action of TBD that the process proceeds by the bifunctional catalysis mechanism, whereby the catalyst molecule takes part in a number of equilibrium processes, resulting in a proton transfer from the amine molecule to cyclocarbonate. Within the framework of calculations by the DFT method, the effect of the solvent (DMSO) is first taken into account in the catalysis mechanism of the hydroxyurethane formation reaction. Based on the quantum chemical calculations of the model structures of the linoleic and oleic fragments of the oligomer, the anomalies of the kinetic curves of the reactions under investigation have been interpreted.