Ring‐opening polymerization of lactones using binaphthyl‐diyl hydrogen phosphate as organocatalyst and resulting monosaccharide functionalization of polylactones |
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| Authors: | Yong Miao Yupin Phuphuak Cyril Rousseau Till Bousquet André Mortreux Suwabun Chirachanchai Philippe Zinck |
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| Institution: | 1. Université Lille Nord de France, F‐59000 Lille, France;2. Ecole Nationale Supérieure de Chimie de Lille, Unité de Catalyse et Chimie du Solide, CCM, F‐59652 Villeneuve d'Ascq, France;3. Université de Lille 1, Science et Technologie, Unité de Catalyse et Chimie du Solide, CCM, F‐59655 Villeneuve d'Ascq, France;4. Centre National de la Recherche Scientifique, UMR 8181, F‐59652 Villeneuve d'Ascq, France;5. The Petroleum and Petrochemical College, Chulalongkorn University, Bangkok, Thailand;6. Center for Petroleum, Petrochemical, and Advanced Materials, Chulalongkorn University, Bangkok, Thailand;7. Centre National de la Recherche Scientifique, UMR 8181, Université d'Artois, Faculté des Sciences Jean Perrin, rue Jean Souvraz, SP18, 62307 Lens Cedex, France |
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| Abstract: | Binaphthyl‐diyl hydrogen phosphate has been assessed for the first time as a catalyst for the ring‐opening polymerization of ε‐caprolactone (CL) and δ‐valerolactone (VL). In the presence of benzyl alcohol as coinitiator at 40–60 °C, the polymerization is quantitative and controlled both in terms of dispersity and of number‐average molecular weight corresponding to the monomer/initiator ratio. The use of a selectively protected D ‐glucose derivative bearing the primary C6 hydroxyl group as initiator leads to the quantitative end‐functionalization of the polyesters in rather short reaction times (ca. 10 min at 60 °C for δ‐VL) with dispersities around 1.08–1.10. Methyl‐α‐D ‐glucopyranoside has been used as a carbohydrate polyol initiator in bulk. The initiation efficiency is partial, leading to hydrophilic carbohydrates functionalized polylactones in a one‐step procedure. © 2013 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013 |
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| Keywords: | biopolymers catalysis cationic polymerization ring‐opening polymerization polyesters |
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