Journal
JOURNAL OF PHYSICAL CHEMISTRY A
Volume 125, Issue 23, Pages 4943-4956Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jpca.1c00850
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Funding
- Eastman Chemical Company
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In this study, the esterification of TMCD and TPA was shown to proceed through an intramolecular acyl-transfer mechanism from the tin complex. These findings provide crucial insights into polyester synthesis and the prevention of undesirable side reactions during production.
Polyesters synthesized from 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD) and terephthalic acid (TPA) are improved alternatives to toxic polycarbonates based on bisphenol A. In this work, we use omega B97X-D/LANL2DZdp calculations, in the presence of a benzaldehyde polarizable continuum model solvent, to show that esterification of TMCD and TPA will reduce and subsequently dehydrate a dimethyl tin oxide catalyst, becoming ligands on the now four-coordinate complex. This reaction then proceeds most plausibly by an intramolecular acyl-transfer mechanism from the tin complex, aided by a coordinated proton donor such as hydronium. These findings are a key first step in understanding polyester synthesis and avoiding undesirable side reactions during production.
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