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Synthesis and low temperature characterization of iso‐oleic ester derivatives
Author(s) -
Ngo Helen,
Latona Renee,
Wagner Karen M.,
Nuñez Alberto,
Ashby Richard,
Dunn Robert O.
Publication year - 2016
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/ejlt.201500468
Subject(s) - differential scanning calorimetry , oleic acid , melting point , chemistry , alkyl , thermogravimetric analysis , thermal stability , isopropyl , organic chemistry , cloud point , lauric acid , pour point , fatty acid , biochemistry , aqueous solution , physics , thermodynamics
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. Practical applications: Since saturated fats have high melting points, they are solids which can be harmful to our health and can cause damage to machinery. There is an urgent need to develop methods to produce fats with low melting points to replace the unwanted fats. In this paper, a series of modified branched‐chain fatty acid ester derivatives (i.e., iso‐oleic acid esters) that are liquid at room temperature with enhanced fluidity were synthesized. These ester fats have been found to perform much better than the original fatty acids and saturated fats. These findings are important as these iso‐oleic ester fats can potentially replace solid materials which are often problematic at low temperatures. Iso‐oleic ester derivatives containing bulky and branched‐chain alkyl groups exhibit reduce melting point in comparison to a smaller alkyl group such as methyl ester.