Production of 9-Hydroxynonanoic Acid from Methyl Oleate and Conversion into Lactone Monomers for the Synthesis of Biodegradable Polylactones

摘要

The feasibility of a previously established method based on ozonolysis and hydrogenation reactions for the production of 9-hydroxynonanoic acid from oleic acid has been demonstrated.Metal catalyzed lactonization conditions have been used to convert 9-hydroxynonanoic acid into 1,11-dioxacycloicosane-2,12-dione,which is a potential monomer in the synthesis of polylactones.The structure of 9-hydroxynonanoic acid and 1,11-dioxacycloicosane-2,12-dione has been confirmed by ~1H NMR,13C NMR,and FTIR.In addition,9-hydroxynonanoic acid was analyzed by high-resolution mass spectroscopy and 1,11-dioxacycloicosane-2,12-dione was analyzed by GC-MS.Aliphatic poly(nonanolactones) have been synthesized via ring-opening polymerization of the dilactone.The structure and number average molecular weight (M_n) of the poly(nonanolactones) have been calculated by ~1H NMR and GPC.The physical properties of these poly(nonanolactones) have been characterized by modulated differential scanning calorimetry (MDSC) and thermogravimetric analysis (TGA).