Synthesis and low temperature characterization of iso‐oleic ester derivatives

Abstract

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.

Synthesis and Characterization of Iso-Undecenoic and Iso-Undecanoic Acids Based Polyol Esters

“…8−10 Because iso-unsaturated fatty acids (IUFAs) can be easily obtained by zeolite catalyzed skeletal isomerization of unsaturated fatty acids (UFAs) and also as byproducts in clay catalyzed polymerization of (UFAs) at high temperatures in the oleochemical industry, 11−13 synthesis of polyol esters using these iso-unsaturated fatty acids has become the area of interest for researchers in recent past, e.g., Ngo et al, have used isooleic acid to synthesize iso-oleic acid esters as lubricant base stocks by the reaction of different fatty alcohols, and they observed that the synthesized iso-oleic acid esters showed a lower pour point and cold flow properties and high thermal and oxidative stabilities. 14 Beimesch et al synthesized and studied lubricant properties of di-and tripentaerythritol esters of isostearic acid. 15 10-Undecenoic acid (UDA) is a C 11 -carbon terminal monounsaturated fatty acid and is produced by pyrolysis of ricinoleic acid, the major fatty acid present in castor oil.…”

Lipid Oxidation and Volatile Compounds of Almonds as Affected by Gaseous Chlorine Dioxide Treatment to Reduce Salmonella Populations

“…Phenolphthalein (0.01%) was added as an indicator. The mixture was stirred during titration until it remained pink for 10 s. 47 The acid value was calculated as oleic acid equivalent (%) using the following equation…”

Synthesis and Physicochemical Properties of Low Viscosity 2‐Ethylhexyl Alkyl Ethers Made from Palm‐Based Esters as Potential Biolubricant

“…T c was taken from the initial cooling cycle and recorded as the peak value. [ 20 ] DSC data were analyzed using the Pyris software Version 10.1.0.0412 (Perkin Elmer, U.S.).…”