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Lubricating and Waxy Esters. 6. Synthesis and Physical Properties of (E)‑Didec-9-enyl Octadec-9-enedioate and Branched Derivatives
journal contribution
posted on 2014-12-24, 00:00 authored by Shaojun Li, Laziz Bouzidi, Suresh S. NarineA 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.
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thermogravimetric analysisstabilityPhysical PropertiesWaxy Estersderivativedideccompoundexploitationaliphatic6. Synthesisflow behaviorcontentSteglish esterificationlubricanthydroxyl groupscosmeticBranched DerivativesAscanning calorimetryprotuberant branchespharmaceuticalOctadeccPfunctionoctadecrheometrycharacteristicsteric hindrancesepoxideLubricatingapplicationphase transition behaviorperformancecondensation reaction
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