Polyester That is Degradable by Sodium Bicarbonate After Oxidation of Sulfide to Sulfone: Polyester from Glyceraldehyde Ethylene-Thioacetal
DOI:
https://doi.org/10.59796/jcst.V16N4.2026.227Keywords:
β-elimination, glyceraldehyde, oxidative degradation, polyester, sodium bicarbonate, sulfone, thioacetalAbstract
Polyesters bearing the 2-thioethyl ester moiety degrade through oxidation to sulfone followed by b-elimination promoted by a base. The basicity of sodium carbonate is essential for the b-elimination process, while degradation using sodium bicarbonate has proven unsuccessful. To achieve highly selective degradation, novel polyesters were developed in which sodium bicarbonate can promote the b-elimination process. A thioacetal of glyceraldehyde was synthesized as the monomer for the preparation of a model ester and of polyesters. The model diester was prepared by reaction with benzoyl chloride. Quantitative oxidation of the model diester to the bis-sulfone and subsequent b-elimination using sodium bicarbonate solution were monitored by 1H-NMR spectroscopy. Polyesters were synthesized through reactions with terephthaloyl chloride and isophthaloyl chloride. The oxidative degradation of these polyesters was successfully carried out via oxidation followed by treatment with sodium bicarbonate solution.
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