Technical Abstract: 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, iso-propyl, octyl, 2-ethylhexyl) using propionic and octanoic acids without the need for either solvent or catalyst. Each synthetic diester was evaluated for both cold flow behavior 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 ester side chain and branching in the ester head group has a positive influence on the low temperature properties of diesters. Improved oxidation stability is achieved when the chain length of the ester side chain is decreased. Additionally, the ester side chain plays a larger role in oxidation stability than the ester head group, which may be due to the secondary versus primary nature of the ester linkages. These products may prove useful in the search for bio-based industrial materials, such as lubricants, surfactants, and fuel additives.