Production of 9-hydroxynonanoic acid from methyl oleate and conversion into lactone monomers for the synthesis of biodegradable polylactones

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 (1)H NMR, (13)C 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 (1)H NMR and GPC. The physical properties of these poly(nonanolactones) have been characterized by modulated differential scanning calorimetry (MDSC) and thermogravimetric analysis (TGA).