Document Type : Original Article

Authors

• Abdol Hossein Masoudi Gazi
• Gholam Reza Moradi Robati

Chemistry department of Tirtash Tobacco Research and Eduction center, Tirtash ,Iran

Abstract

Triacetin (1,3-Diacetyloxypropan-2-yl acetate) serves as a plasticizer in the manufacturing of cellulose acetate cigarette filters, composed of cellulose acetate fibers, plug wrap paper, hotmelt adhesive, and triacetin. Quantum chemical calculations and thermodynamic analyses were performed using Density Functional Theory (DFT) at the B3LYP level with the 6-311++G** basis set to examine triacetin's structure and its interactions with cigarette smoke chemical components. Results, corrected for intramolecular basis set superposition error (BSSE), revealed that bond formation primarily occurs through oxygen and hydrogen atoms. Among the studied complexes, triacetin exhibited the highest stability with hydrogen cyanide and the lowest stability with carbon monoxide, based on interaction energy values. All interactions showed nonspontaneous adsorption (ΔG > 0), with positive ΔH values indicating endothermic behavior for triacetin-carbon monoxide and triacetin-benzene complexes, while other interactions were exothermic (negative ΔH). Natural Bond Orbital (NBO) analysis and Quantum Theory of Atoms in Molecules (QTAIM) demonstrated covalent characteristics for C-O, C-C, and C-H bonds in triacetin, alongside van der Waals interactions in its complexes. Notably, a unique cage critical point (CCP) was observed in the triacetin-formaldehyde complex, and a dihydrogen bond was identified in the triacetin-benzene interaction. These findings enhance our understanding of triacetin’s behavior and interactions, contributing to the optimization of cigarette filter manufacturing.

Keywords

• Triacetin
• Density Functional Theory
• NBO
• QTAIM