Publication: A DFT investigation of methanolysis and hydrolysis of triacetin
Issued Date
2010-09-01
Resource Type
ISSN
01661280
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2-s2.0-77955087581
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Mahidol University
Rights Holder(s)
SCOPUS
Bibliographic Citation
Journal of Molecular Structure: THEOCHEM. Vol.955, No.1-3 (2010), 23-32
Suggested Citation
Taweetham Limpanuparb, Kraiwan Punyain, Yuthana Tantirungrotechai A DFT investigation of methanolysis and hydrolysis of triacetin. Journal of Molecular Structure: THEOCHEM. Vol.955, No.1-3 (2010), 23-32. doi:10.1016/j.theochem.2010.05.022 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/28647
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Title
A DFT investigation of methanolysis and hydrolysis of triacetin
Abstract
The thermodynamic and kinetic aspects of the methanolysis and hydrolysis reactions of glycerol triacetate or triacetin, a model triacylglycerol compound, were investigated by using Density Functional Theory (DFT) at the B3LYP/6-31++G(d,p) level of calculation. Twelve elementary steps of triacetin methanolysis were studied under acid-catalyzed and base-catalyzed conditions. The mechanism of acid-catalyzed methanolysis reaction which has not been reported yet for any esters was proposed. The effects of substitution, methanolysis/hydrolysis position, solvent and face of nucleophilic attack on the free energy of reaction and activation energy were examined. The prediction confirmed the facile position at the middle position of glycerol observed by NMR techniques. The calculated activation energy and the trends of those factors agree with existing experimental observations in biodiesel production. © 2010 Elsevier B.V.