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 degrees C), competitive flow characteristics (210-773 cP at 40 degrees C and 31-66 cP at 100 degrees C) and superior low-temperature performance properties (-27 to -70 degrees C) suitable for exploitation in various applications such as lubricants, cosmetics, and pharmaceuticals.