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Issue 51, 2020, Issue in Progress

Bismuth subsalicylate, a low-toxicity catalyst for the ring-opening polymerization (ROP) of l-lactide (l-LA) with aliphatic diol initiators: synthesis, characterization, and mechanism of initiation

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Abstract

The ring-opening polymerization (ROP) of L-lactide (L-LA) was induced by the catalytic action of bismuth subsalicylate (BiSS) using linear aliphatic diols [HO(CH2)nOH, where n = 2, 3, 4, 5, 6, and 8] as initiators and chain transfer agents. The theoretical and experimental degree of polymerization (DP) in all samples of α,ω-hydroxy telechelic poly(L-lactide) (HOPLLAOH) had a good agreement in all samples, an effect attributed to the interaction of BiSS with HO(CH2)nOH inducing a transfer reaction. HOPLLAOH was synthesized and characterized by a range of analytical techniques, confirming the insertion of methylene groups from the initiator into the main chain of the polyester. The glass-transition temperature (Tg) of HOPLLAOH was found to be proportional to the number of methylene groups present in the diol. Various parameters regarding the ROP of L-LA were studied, such as temperature, time of reaction, amount of catalyst, and the nature of the diols. A kinetic study of the reaction allowed the determination of the rate constants (k) and activation energy (Ea). A mechanism of initiation is proposed based on a computational study using density functional theory (DFT), evidencing the role of the alkyl diol as an initiator, producing an alkoxide (Bi–OROH). This species then acts as a nucleophile, attacking the carbonyl group, inducing its insertion, and ultimately completing the ring-opening of L-LA.

Graphical abstract: Bismuth subsalicylate, a low-toxicity catalyst for the ring-opening polymerization (ROP) of l-lactide (l-LA) with aliphatic diol initiators: synthesis, characterization, and mechanism of initiation

Supplementary files

Article information


Submitted
20 Jun 2020
Accepted
10 Aug 2020
First published
20 Aug 2020

This article is Open Access

RSC Adv., 2020,10, 30815-30824
Article type
Paper

Bismuth subsalicylate, a low-toxicity catalyst for the ring-opening polymerization (ROP) of L-lactide (L-LA) with aliphatic diol initiators: synthesis, characterization, and mechanism of initiation

M. G. Ortiz-Aldaco, J. E. Báez and J. O. C. Jiménez-Halla, RSC Adv., 2020, 10, 30815 DOI: 10.1039/D0RA05413E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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