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Open AccessArticle

1,3-Dioxolan-4-Ones as Promising Monomers for Aliphatic Polyesters: Metal-Free, in Bulk Preparation of PLA

1
Department of Chemistry, University of Milan, Via Golgi 19, 20133 Milan, Italy
2
CRC Materiali Polimerici (LaMPo), Department of Chemistry, University of Milan, Via Golgi 19, 20133 Milan, Italy
*
Author to whom correspondence should be addressed.
Polymers 2020, 12(10), 2396; https://doi.org/10.3390/polym12102396
Received: 24 September 2020 / Revised: 13 October 2020 / Accepted: 15 October 2020 / Published: 18 October 2020
(This article belongs to the Special Issue Biodegradable and Biobased Polymers Obtained via Step Polymerization)
The first example of solvent-free, organocatalyzed, polymerization of 1,3-dioxolan-4-ones, used as easily accessible monomers for the synthesis of polylactic acid (PLA), is described here. An optimization of reaction conditions was carried out, with p-toluensulfonic acid emerging as the most efficient Brønsted acid catalyst. The reactivity of the monomers in the tested conditions was studied following the monomer conversion by 1H NMR and the molecular weight growth by SEC analysis. A double activation polymerization mechanism was proposed, pointing out the key role of the acid catalyst. The formation of acetal bridges was demonstrated, to different extents depending on the nature of the aldehyde or ketone employed for lactic acid protection. The polymer shows complete retention of stereochemistry, as well as good thermal properties and good polydispersity, albeit modest molecular weight. View Full-Text
Keywords: PLA; 1,3-dioxolan-4-one; organocatalysis; Brønsted acid; lactide PLA; 1,3-dioxolan-4-one; organocatalysis; Brønsted acid; lactide
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Gazzotti, S.; Ortenzi, M.A.; Farina, H.; Silvani, A. 1,3-Dioxolan-4-Ones as Promising Monomers for Aliphatic Polyesters: Metal-Free, in Bulk Preparation of PLA. Polymers 2020, 12, 2396.

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