Biomimetic processes II. Carbocationic polymerization of isopentenyl alcohol: A model for the synthesis of natural rubber?

Thibault Forestier (1) , Pamela Pasetto (1) , Frédéric Peruch (1, 2) , Alain Deffieux (1, 2) , Judit E. Puskas (3)

1 LCPO - Laboratoire de Chimie des Polymères Organiques
2 Team 1 LCPO : Polymerization Catalyses & Engineering
3 Univ Akron, Dept Polymer Sci

Natural rubber (poly(1.4-cis-isoprene), NR), a polymer of considerable industrial importance due to its exceptional properties, is exclusively produced from the cultivation of Hevea brasiliensis. After numerous attempts by polymer chemists to try to synthesize polyisoprene with very similar structures. none have been produced that exhibit such excellent properties. In this paper we analyze a new bio-inspired route towards NR based oil the carbocationic polymerization of isopentenyl pyrophosphate (IPP) (the natural monomer) and its derivatives. We report in ail initial study, the carbocationic polymerization of isopentenyl alcohol (IPOH) under various polymerization conditions. It is shown that oligomers are produced via 1,2 addition and not via the expected 1,4 addition.

Mots clés: natural rubber; cationic polymerization; isopentenyl alcohol; mechanistic study

Domaines: Polymères

Thibault Forestier, Pamela Pasetto, Frédéric Peruch, Alain Deffieux, Judit E. Puskas. Biomimetic processes II. Carbocationic polymerization of isopentenyl alcohol: A model for the synthesis of natural rubber?. Materials Science and Engineering: C, 2009, 29 (2), pp.357-362. ⟨10.1016/j.msec.2008.06.025⟩. ⟨hal-00380385⟩