Skip to Main content Skip to Navigation
New interface
Journal articles

Free-solvent Michael addition of glycerol to acrylic compounds

Abstract : In this paper, we report the study of the free-solvent nucleophilic addition of alcohols and glycerol to acrylic compounds, in the presence of catalytic bases. With acrylates, Michael addition and transesterification are in competition: only the PTC reaction with t-butyl acrylate gave trifunctionalized glycerol. With acrylonitrile, the cyanoethylation of glycerol varies with catalysts, temperature, time of reactions and amounts of acrylonitrile. Mono functionalisation of glycerol can be obtained in 28% yield. The optimization of the free-solvent Michael addition of glycerol to acrylonitrile (3.4 equiv., 4 mol% NaOH, 5 h) leads to TCEG (tricyanoethylglycerol, 88% yield, 99% purity) without HCl neutralisation, chlorinated solvents or purification (chromatography or distillation). TCEG can be used as a prochiral core of G(0.5) dendrimers.
Complete list of metadata
Contributor : LCP-A2MC UL Connect in order to contact the contributor
Submitted on : Thursday, May 4, 2017 - 11:32:30 AM
Last modification on : Friday, February 4, 2022 - 4:16:05 PM




Frederic Nadeau, Michele Sindt, Nicolas Oget. Free-solvent Michael addition of glycerol to acrylic compounds. New Journal of Chemistry, 2015, 39 (12), pp.9155-9161. ⟨10.1039/c5nj02223a⟩. ⟨hal-01518106⟩



Record views