Preparation of highly pure cyclo-polylactides by optimization of the copper-catalyzed azide-alkyne cycloaddition reaction

R. Liénard; T. Josse; J. De Winter; F. Dubois; P. Gerbaux; O. Coulembier

doi:10.14314/polimery.2017.283

Published : 2021-01-15

Vol. 62 No. 4 (2017)

Preparation of highly pure cyclo-polylactides by optimization of the copper-catalyzed azide-alkyne cycloaddition reaction

R. Liénard T. Josse J. De Winter F. Dubois P. Gerbaux O. Coulembier

DOI: https://doi.org/10.14314/polimery.2017.283

Abstract

This work reports on the preparation of highly pure cyclo-polylactides (Mn ≈ 4 000 g • mol^-1) by the optimization of the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction applied on α-azide-ω-alkyne linear polylactide (PLA) precursors. By adjusting parameters such as the rate of reactant addition and the catalyst loading, monocyclic PLA's with a degree of purity of 93 % are obtained in few minutes. Highly pure monocycles (purity as high as 99.9 %) are also possibly prepared in few hours.

Keywords

lactide ; ring-opening polymerization ; copper-catalyzed azide-alkyne cycloaddition ; cyclization laktyd ; polimeryzacja z otwarciem pierścienia ; cykloaddycja azydek-alkin katalizowana miedzią ; cyklizacja

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Liénard, R., Josse, T., De Winter, J., Dubois, F., Gerbaux, P., & Coulembier, O. (2021). Preparation of highly pure cyclo-polylactides by optimization of the copper-catalyzed azide-alkyne cycloaddition reaction. Polimery, 62(4), 283–290. https://doi.org/10.14314/polimery.2017.283

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R. Liénard help@libcom.pl

Affiliation
University of Mons (UMONS), Laboratory of Polymeric and Composite Materials (LPCM), Center of Innovation and Research in Materials and Polymers (CIRMAP), Place du Parc 23, 7000 Mons, Belgium

T. Josse

Affiliation
University of Mons (UMONS), Laboratory of Polymeric and Composite Materials (LPCM), Center of Innovation and Research in Materials and Polymers (CIRMAP), Place du Parc 23, 7000 Mons, Belgium

J. De Winter

Affiliation
University of Mons (UMONS), Organic Synthesis and Mass Spectrometry Laboratory (S2MOS), Place du Parc 23, 7000 Mons, Belgium

F. Dubois

Affiliation
University of Mons (UMONS), Laboratory of Polymeric and Composite Materials (LPCM), Center of Innovation and Research in Materials and Polymers (CIRMAP), Place du Parc 23, 7000 Mons, Belgium; present address: Department Materials Research and Technology, National Composite Center-Luxembourg, Luxembourg Institute of Science and Technology LIST, Luxembourg

P. Gerbaux

Affiliation
University of Mons (UMONS), Organic Synthesis and Mass Spectrometry Laboratory (S2MOS), Place du Parc 23, 7000 Mons, Belgium

O. Coulembier

Affiliation
University of Mons (UMONS), Laboratory of Polymeric and Composite Materials (LPCM), Center of Innovation and Research in Materials and Polymers (CIRMAP), Place du Parc 23, 7000 Mons, Belgium