Investigation of the Initiating and Catalytic Behavior of Tri-n-butyltin(IV) n-Butoxide in Ring-Opening Polymerization of ε-Caprolactone and Transesterification of Poly(L-lactic acid)

Winita Punyodom; Puttinan Meepowpan; Boontharika Thapsukhon; Manita Dumklang; Wanich Limwanich

doi:https://doi.org/10.12982/CMJS.2022.003

Investigation of the Initiating and Catalytic Behavior of Tri-n-butyltin(IV) n-Butoxide in Ring-Opening Polymerization of ε-Caprolactone and Transesterification of Poly(L-lactic acid)

Winita Punyodom, Puttinan Meepowpan, Boontharika Thapsukhon, Manita Dumklang and Wanich Limwanich
* Author for corresponding; e-mail address: wanich.lim@gmail.com
Volume: Vol.49 No.1 (Special Issue I : Jan 2022)
Research Article
DOI: https://doi.org/10.12982/CMJS.2022.003
Received: 4 June 2021, Revised: 12 June 2021, Accepted: 5 July 2021, Published: -

Citation: Punyodom W., Meepowpan P., Thapsukhon B. and Limwanich M.D. .W., Investigation of the Initiating and Catalytic Behavior of Tri-n-butyltin(IV) n-Butoxide in Ring-Opening Polymerization of ε-Caprolactone and Transesterification of Poly(L-lactic acid), Chiang Mai Journal of Science, 2022; 49(1): e2022003. DOI 10.12982/CMJS.2022.003.

Abstract

Tri-n-butyltin(IV) n-butoxide (nBu₃SnOnBu) was successfully synthesized and utilized as a stable and homogeneous initiator for the small-scale synthesis of biodegradable polymers in our laboratory. From our previous works, the initiating performance of nBu₃SnOnBu in the ring-opening polymerization (ROP) of cyclic ester monomers was completely investigated by differential scanning calorimetry (DSC). It was found that nBu₃SnOnBu acted as the slow initiator in the ROP of ε-caprolactone (ε-CL) due to its high steric hindrance around the active center. Moreover, it could be used in the stereoselective ROP of racemic-lactide (rac-LA). The synthesized nBu₃SnOnBu showed higher stereoselectivity than the conventional tin(II) octoate (Sn(Oct)₂) system. In this present work, the effectiveness of nBu₃SnOnBu in scaled-up (250 g) of the synthesis of poly(ε-caprolactone) (PCL) was further investigated comparing to small-scale polymerization (4 g). Furthermore, the catalytic performance of this nBu₃SnOnBu in the transesterification of high molecular weight poly(L-lactic acid) (PLA) was also investigated for the first time. The transesterification of PLA with 0.05 M and 0.10 M of soluble nBu3SnOnBu catalyst in CHCl₃ was successfully investigated by the gel permeation chromatography (GPC) technique. It was found that the molecular weight of PLA dramatically decreased with increasing time and nBu₃SnOnBu concentration. From the kinetics study, nBu₃SnOnBu acted as a highly active transesterification catalyst for PLA. From a mechanistic study, the transesterification mechanism of PLA with nBu₃SnOnBu catalyst was proposed through intramolecular transesterification.

Keywords: poly(L-lactic acid), transesterification, biodegradable polymer, tin(IV) alkoxide, kinetics

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