Facile synthesis, characterization, and ab-initio DFT simulations of energy efficient NN′ dialkyl 1,4 benzene dicarboxamide monomers recovered from PET bottle waste

Aminolytic chemical recycling is performed for obtaining NN ' diethyl 1,4 benzene dicarboxamide, NN ' dibutyl 1,4 benzene dicarboxamide, and NN ' dihexyl 1,4 benzene dicarboxamide from Polyethylene terephthalate bottle waste. The compounds were characterized through Fourier transform Infrared spectroscopy, Raman spectroscopy, UV-Visible spectroscopy, H-1 NMR, C-13 NMR, mass spectrometry, and elemental analysis. Thermal properties were also analyzed with the help of thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). Density Functional Theory (DFT) study has been performed at GGA-BLYP (Becke's and Lee-Yang-Parr) functional using SZ basis set to investigate the vibrational frequencies and physical parameters. Experimental vibrational frequencies were found in good accord with the experimental values. Calorific values of the products have been determined using bomb calorimeter as per standard ASTM D240. The values have been correlated with increment of methylene units from NN ' diethyl BdCA to NN ' dihexyl BdCA using standard molar enthalpies of carbon and hydrogen. SEM and EDX analysis of the char residues after combustion has also been carried out to insight the effect of N-alkyl chain length on calorific values. The calorific values of the recovered compounds are comparable to commercial solid fuels and the compounds may find potential applications in aerospace industry.