Synthesis of waxes from vegetable oil derived self-metathesized aliphatic esters

•Wax ester from the oil of the jojoba plant self-metathesized.•The monoester oligomers products compare very favorably with commercial waxes.•The oligomers inherited narrow range of thermal properties from the natural oil.•High potential for specialized viscous fluids to hard brittle solids applications.

Five wax ester oligomers of oleyl oleate (monomer to pentamer) produced from the self-metathesis of oleyl oleate derived from soybean oil were separated from the crude metathesis product by column chromatography. The purified compounds contained trans- and cis- configurations with a trans/cis ratio ranging from 3.6 for the monomer to 6.6 for the pentamer. The thermal transition behaviour of the oligomers as revealed by DSC was directly related to their trans- and cis- composition. Although odd/even effects presented predictable deviations, the crystallization and melting characteristics such as temperature and enthalpy scaled predictably with molecular size, and demonstrated a diminishing effect of incremental increases in monomer units. As determined by TGA, and except for the monomer which started to evaporate at ∼200 °C, the oligomers presented excellent thermal stability with onsets of degradation higher than 360 °C. The thermal transition characteristics of the monoester oligomers are comparable to commercial waxes and show potential for their use in a large range of wax applications ranging from viscous fluids to hard brittle solids. Furthermore, the thermal transitions occurred over narrow temperature spans, a feature that is useful for applications requiring collimated melting and crystallization ranges.