Isomerization-hydroboration-oxidation strategy: Access to long chain AB- and AA-type oleyl based monomers and polymers thereof

Prakash Sudhir Sane (1) , Thomas Lebarbé (2) , Etienne Grau (1, 3) , Henri Cramail (1, 3)

1 LCPO - Laboratoire de Chimie des Polymères Organiques
2 ITERG - Institut des Corps Gras
3 Team 2 LCPO : Biopolymers & Bio-sourced Polymers

A strategy to convert by isomerization-hydroboration-oxidation reaction the internal double bond of oleic acid to a terminal alcohol function, leading to linear long-chain ,-difunctional substrates has been investigated. Using this strategy, oleic acid-based AB- and AA-monomers were prepared and characterized by FTIR-ATR and NMR spectroscopy. Thermoplastic aliphatic linear polyesters, polycarbonates, and polyurethanes were then synthesized by reacting the so-formed bio-based monomers via polycondensation in bulk, using 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as an organocatalyst. Thus, starting from easily available bio-based starting compound, the synthesis of linear long methylene chain aliphatic polyesters, polycarbonates, and polyurethanes (by isocyanate free route) is reported. The structural and thermal characterizations of the synthesized polymers were performed by means of NMR, SEC, DSC, and TGA experiments.

Mots clés: Carbamate; Fatty acid esters; Isomerization; RENEWABLE RESOURCES; SEMICRYSTALLINE POLYESTERS; METHYL OLEATE; OILS; METATHESIS; CONVERSION; CHEMISTRY; CHEMICALS; FATS

Domaines: Polymères; Matériaux; Chimie

Prakash Sudhir Sane, Thomas Lebarbé, Etienne Grau, Henri Cramail. Isomerization-hydroboration-oxidation strategy: Access to long chain AB- and AA-type oleyl based monomers and polymers thereof. European Journal of Lipid Science and Technology, 2016, 118 (11), pp.1620-1629. ⟨10.1002/ejlt.201600064⟩. ⟨hal-01411518⟩