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Synthesis of five and six-membered cyclic glycerilic carbonates bearing exocyclic urethane functions

Nohra, Bassam and Candy, Laure and Blanco, Jean-François and Raoul, Yann and Mouloungui, Zephirin Synthesis of five and six-membered cyclic glycerilic carbonates bearing exocyclic urethane functions. (2013) European Journal of Lipid Science and Technology, vol. 115 (n° 1). pp. 111-122. ISSN 1438-7697

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Official URL: http://dx.doi.org/10.1002/ejlt.201200082

Abstract

Five (5CGC) and six (6CGC) membered cyclic glycerilic carbonates having exocyclic urethane functions, as potentialmonomers for polyurethanes and polycarbonates, were prepared by two different routes: ‘‘twosteps’’ and the ‘‘one-pot’’ synthesis. For the ‘‘two-steps’’ route, based on the consecutive aminolysis and transesterification reactions, a catalyst screening has been performed. Phosphazene showed the best catalytic activity and provided 5CGC and 6CGC in appreciable amounts whereas the other catalysts favored 5CGCformation. An increase inmolar ratio of dimethyl carbonate (DMC) increased the yield and the conversion. In the ‘‘one-pot’’ synthesis, where aminolysis and transesterification were simultaneous, a competition between products formation was demonstrated. In addition to the formation of monohydroxyurethanes and glycerilic cyclic carbonates (5CGC and 6CGC), the fast aminolysis of 6CGC and the slower aminolysis of 5CGC was responsible for a partial di-hydroxyurethanes production. The controlled and combined effects of catalyst and DMC excess acting as solvent and reagent allowed to selectively controlling the aminolysis and the transesterification reactions. The same reaction conditions were used for the synthesis of bicyclic carbonates. These new molecules enriched with urethane functions, provided novel and more environmentally friendly synthons for the synthesis of polyurethanes without the use of phosgene or isocyanate.

Item Type:Article
Additional Information:Thanks to Elsevier editor. The original PDF of the article can be found at European Journal of Lipid Science and Technology website : http://onlinelibrary.wiley.com/journal/10.1002/%28ISSN%291438-9312
Audience (journal):International peer-reviewed journal
Uncontrolled Keywords:
Institution:French research institutions > Centre National de la Recherche Scientifique - CNRS (FRANCE)
Université de Toulouse > Institut National Polytechnique de Toulouse - INPT (FRANCE)
French research institutions > Institut National de la Recherche Agronomique - INRA (FRANCE)
Université de Toulouse > Université Paul Sabatier-Toulouse III - UPS (FRANCE)
Other partners > Proléa (FRANCE)
Laboratory name:
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Deposited By: Vincent GERBAUD
Deposited On:28 Oct 2013 12:00

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