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