Polyesters synthesized from 9-hydroxynonanoic acid derived from lipid materials.

摘要

The feasibility of a method based on ozonolysis and hydrogenation reactions for the production of 9-hydroxynonanoic acid from methyl oleate and polyols was demonstrated. Pure 9-hydroxynonanoic acid (9-HNA) was obtained by either recrystallization or silica gel column chromatography. The structure of 9-hydroxynonanoic acid was confirmed by 1H NMR, 13C NMR, FTIR and HR-MS. The methodologies have also been demonstrated to be amenable to 100 gram scales to synthesize 9-hydroxynonanoic acid. 9-hydroxynonanoic acid was converted to 1, 11-dioacycloicosane-2,12-dione (dilactone), which is a potential monomer for synthesis of polyesters. The structure of 1,11-dioacycloicosane-2,12-dione (dilactone) was identified by 1H NMR, 13C NMR, FTIR and GC-MS. Aliphatic polyesters were synthesized via ring opening polymerization of these dilactones. The structure and the number average molecular weight (Mn) of the polyesters were calculated by 1H NMR and GPC. Some physical properties of the polyesters were characterized by DSC and TGA.