Document Detail


Production of 9-hydroxynonanoic Acid from methyl oleate and conversion into lactone monomers for the synthesis of biodegradable polylactones.
MedLine Citation:
PMID:  18271512     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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:
Guoguang Liu; Xiaohua Kong; Hayley Wan; Suresh Narine
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2008-02-14
Journal Detail:
Title:  Biomacromolecules     Volume:  9     ISSN:  1526-4602     ISO Abbreviation:  Biomacromolecules     Publication Date:  2008 Mar 
Date Detail:
Created Date:  2008-03-11     Completed Date:  2008-04-15     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100892849     Medline TA:  Biomacromolecules     Country:  United States    
Other Details:
Languages:  eng     Pagination:  949-53     Citation Subset:  IM    
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.
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MeSH Terms
Descriptor/Qualifier:
2-Propanol / chemistry
Biodegradation, Environmental
Calorimetry, Differential Scanning
Fatty Acids / chemical synthesis*,  chemistry
Hafnium / chemistry
Lactones / chemical synthesis*,  chemistry
Lanthanum / chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Oleic Acids / chemistry*
Spectroscopy, Fourier Transform Infrared
Thermogravimetry
Chemical
Reg. No./Substance:
0/1,11-dioxacycloicosane-2,12-dione; 0/9-hydroxynonanoic acid; 0/Fatty Acids; 0/Lactones; 0/Oleic Acids; 10099-58-8/lanthanum chloride; 112-62-9/methyl oleate; 13499-05-3/hafnium chloride; 67-63-0/2-Propanol; 7439-91-0/Lanthanum; 7440-58-6/Hafnium

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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