Lubricating and Waxy Esters. 6. Synthesis and Physical Properties of (E)‑Didec-9-enyl Octadec-9-enedioate and Branched Derivatives

A fatty aliphatic “Jojoba-like” ester, didec-9-enyl octadec-9-enedioate, was synthesized by Steglish esterification, and C3-branched derivatives were prepared from its epoxide by a solvent-free epoxide ring-opening and one-pot normal condensation reaction. The thermal stability, phase transition behavior, solid fat content, and flow behavior were investigated using thermogravimetric analysis, differential scanning calorimetry, p-NMR, and rotational rheometry, respectively. These properties were predictably varied as a function of branching, explained by the combined effects of mass, hydroxyl groups, and geometric steric hindrances imposed by the protuberant branches. The compounds demonstrated high thermal stability (>230 °C), competitive flow characteristics (210–773 cP at 40 °C and 31–66 cP at 100 °C) and superior low-temperature performance properties (−27 to −70 °C) suitable for exploitation in various applications such as lubricants, cosmetics, and pharmaceuticals.