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Synthesis and low temperature characterization of iso-oleic ester derivatives

Helen Ngo, Renee Latona, Karen M Wagner, Alberto Nunez, Richard Asby, Robert O Dunn
European Journal of Lipid Science and Technology 2016 v.118 no.12 pp. 1915-1925
alcohols, chemical derivatives, differential scanning calorimetry, esterification, esters, fluid mechanics, melting, melting point, pour point, synthesis, temperature, thermal stability, thermogravimetry
Three new iso-oleic ester derivatives (i.e., isopropyl ester (IOA-iPrE, 6), n-butyl ester (IOA-n-BuE, 7), and 2-ethylhexyl ester (IOA-2-EHE, 8)) were synthesized from iso-oleic acid (IOA, 4) using a standard esterification method. These esterified alcohols were chosen because of their bulky and branched-chain alkyl groups which can reduce melting point in comparison to a smaller alkyl group such as methyl ester. The differential scanning calorimetry (DSC), cloud point and pour point results showed that esters 6, 7, and 8 had much lower melting transition temperatures and cold flow properties than the methyl (IOA–FAME, 5) and parent 4. The oxidative and thermal stability by pressure (P-DSC) and thermogravimetric analysis (TGA) results also showed a very similar trend where the bulkier and branched-chain alkyl esters had better stability than the smaller headgroup esters.