6533b870fe1ef96bd12cf161
RESEARCH PRODUCT
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
Gilles BoniAstrid HoppeLaurent PlasseraudJean-pierre CouvercelleClaire-hélène BrachaisFaten Sadakasubject
N-heterocarbene precursorLactideLetterOrganic ChemistryRing-opening polymerizationPentaerythritollcsh:QD241-441chemistry.chemical_compoundChemistryimidazolium-2-carboxylateschemistryPolymerizationlcsh:Organic chemistryBenzyl alcoholgreen polymerization reactionPolymer chemistryaliphatic polyestersOrganic chemistrylcsh:QorganocatalysisCarboxylatelcsh:ScienceCaprolactoneEthylene glycoldescription
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 1H and 13C{1H} 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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2013-04-01 | Beilstein Journal of Organic Chemistry |