title: Production of 9-hydroxynonanoic Acid from methyl oleate and conversion into lactone monomers for the synthesis of biodegradable polylactones.
abstract: 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).
authors.affiliation: Alberta Lipid Utilization Program, Department of Agricultural Food and Nutritional Science, 4-10 Agriculture/Forestry Centre, University of Alberta, Edmonton, Alberta T6G 2P5, Canada.
authors.forename: Guoguang
authors.initials: G
authors.lastname: Liu
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Kong
authors.forename: Hayley
authors.initials: H
authors.lastname: Wan
authors.forename: Suresh
authors.initials: S
authors.lastname: Narine
mesh_terms: D019840:2-Propanol / Q000737:chemistry; D001673:Biodegradation, Environmental; D002152:Calorimetry, Differential Scanning; D005227:Fatty Acids / Q000138:chemical synthesis* / Q000737:chemistry; D006195:Hafnium / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D007811:Lanthanum / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009829:Oleic Acids / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared; D013818:Thermogravimetry
chemical_list: C528064:1,11-dioxacycloicosane-2,12-dione; D005227:Fatty Acids; D007783:Lactones; D009829:Oleic Acids; C028521:lanthanum chloride; C005576:methyl oleate; D007811:Lanthanum; C044004:hafnium chloride; C528063:9-hydroxynonanoic acid; D019840:2-Propanol; D006195:Hafnium