Diesters from Oleic Acid: Synthesis, Low Temperature Properties, and Oxidation Stability

Several diesters were prepared from commercially available oleic acid and common organic acids. The key step in the three step synthesis of oleochemical diesters entails a ring opening esterification of alkyl 9,10-epoxyoctadecanoates (alkyl: propyl, isopropyl, octyl, 2-ethylhexyl) using propionic and octanoic acids without the need for either solvent or catalyst. Each synthetic diester was evaluated for both low temperature operability and oxidation stability through measurement of cloud point, pour point, oxidation onset temperature, and signal maximum temperature. It was discovered that increasing chain length of the mid-chain ester and branching in the end-chain ester had a positive influence on the low temperature properties of diesters. Improved oxidation stability is achieved when the chain length of the mid-chain ester is decreased. Additionally, the mid-chain ester plays a larger role in oxidation stability than the end-chain ester. These products may prove useful in the search for bio-based industrial materials, such as lubricants, surfactants, and fuel additives.