A study of fatty acid methyl esters with epoxy or alkyne functionalities |
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Authors: | Johan Samuelsson Mats Johansson |
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Affiliation: | (1) Department of Polymer Technology, Royal Institute of Technology, SE-100 44 Stockholm, Sweden |
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Abstract: | Described are the physical and chemical properties of the methyl esters of two uncommon fatty acids: vernolic acid, containing
an epoxy group, and crepenynic acid, containing a triple bond. The incorporation of an epoxy or alkyne group into the fatty
acid structure is shown to greatly affect the properties compared to conventional unsaturated fatty acids. The methyl esters
have been characterized and compared with ordinary fatty acid methyl esters (i.e., methyl oleate and linoleate) with respect
to spectroscopic characterization 1H nuclear magnetic resonance (NMR)], 13C NMR, and Fourier transform infrared), rheological properties, and oxidative reactivity (using chemiluminescence). Both methyl
vernoleate and methyl crepenynate could successfully be produced by transesterification under basic conditions without reaction
of the epoxy or alkyne groups. Rheological measurements showed that the methyl esters had a significantly lower viscosity
compared to their triglyceride analogs. Smaller differences were seen when comparing the different methyl esters where methyl
vernoleate had the highest viscosity due to the presence of the more polar oxirane group. Very large differences were found
with respect to the oxidation rate of the different methyl esters. Methyl crepenynate was shown to oxidize extremely rapidly,
whereas methyl vernoleate was very stable toward oxidation. |
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Keywords: | Alkyne characterization chemiluminescence crepenynic acid epoxy methyl esters NMR oxidation vernolic acid viscosity |
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