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1-n-Butyl-3-methylimidazolium-2-carboxylate: a versatile precatalyst for the ring-opening polymerization of ?-caprolactone and rac-lactide under solvent-free conditions.

ABSTRACT: The ring-opening polymerization of ?-caprolactone (?-CL) and rac-lactide (rac-LA) under solvent-free conditions and using 1-n-butyl-3-methylimidazolium-2-carboxylate (BMIM-2-CO2) as precatalyst is described. Linear and star-branched polyesters were synthesized by successive use of benzyl alcohol, ethylene glycol, glycerol and pentaerythritol as initiator alcohols, and the products were fully characterized by (1)H and (13)C{(1)H} NMR spectroscopy, gel permeation chromatography (GPC), and differential scanning calorimetry (DSC). BMIM-2-CO2 acts as an N-heterocyclic carbene precursor, resulting from in situ decarboxylation, either by heating under vacuo (method A) or by addition of NaBPh4 (method B). Possible catalytic and deactivation mechanisms are proposed.

SUBMITTER: Hoppe A 

PROVIDER: S-EPMC3628682 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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1-n-Butyl-3-methylimidazolium-2-carboxylate: a versatile precatalyst for the ring-opening polymerization of ε-caprolactone and rac-lactide under solvent-free conditions.

Hoppe Astrid A   Sadaka Faten F   Brachais Claire-Hélène CH   Boni Gilles G   Couvercelle Jean-Pierre JP   Plasseraud Laurent L  

Beilstein journal of organic chemistry 20130403

The ring-opening polymerization of ε-caprolactone (ε-CL) and rac-lactide (rac-LA) under solvent-free conditions and using 1-n-butyl-3-methylimidazolium-2-carboxylate (BMIM-2-CO2) as precatalyst is described. Linear and star-branched polyesters were synthesized by successive use of benzyl alcohol, ethylene glycol, glycerol and pentaerythritol as initiator alcohols, and the products were fully characterized by (1)H and (13)C{(1)H} NMR spectroscopy, gel permeation chromatography (GPC), and differen  ...[more]

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