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Vinyl monomers such as styrene may undergo undesired polymerization reactions during the industrial processes in which they are synthesized and purified. To avoid this undesired phenomenon, polymerization inhibitors such as (2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl (TEMPO) and its analogues can be used. An inhibitor and stability screening setup built in-house was used to compare the effectiveness of thirteen TEMPO analogues in inhibiting the polymerization of styrene in toluene at 130 °C. The data show that the substituent in the 4′-position in the cyclic structure of the TEMPO molecules strongly influenced their effectiveness in inhibiting polymerization. Computational methods based on the density functional theory (DFT) approach have been utilized to understand the reactivity of the TEMPO analogues. The global reactivity descriptors derived from the DFT calculations indicate that the TEMPO analogues with high global electrophilicity are more effective than those with low global electrophilicity in inhibiting the polymerization. The data suggest that the solubility of the TEMPO analogues in toluene and the keto–enol tautomerism of certain molecules may also affect their ability to inhibit styrene polymerization.
Journal of Polymer Research – Springer Journals
Published: Oct 31, 2017
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