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Lubricating and Waxy Esters. VI. Effect of Symmetry about Ester on Crystallization of Linear Monoester Isomers

Trent Centre for Biomaterials Research, Departments of Physics & Astronomy and Chemistry, Trent University, 1600 West Bank Drive, Peterborough, ON K9J 7B8, Canada
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Symmetry 2014, 6(3), 655-676; https://doi.org/10.3390/sym6030655
Received: 21 May 2014 / Revised: 22 July 2014 / Accepted: 31 July 2014 / Published: 7 August 2014
(This article belongs to the Special Issue Chemical Applications of Symmetry)
The crystal structure development of jojoba-like esters incorporating either 1-decenoic acid and/or 1-decenol, namely octadec-9-enyl dec-9-enoate (JLE-281), and its isomer dec-9-enyl oleate (JLE-282) was investigated to reveal the effect of symmetry about the ester group on crystallization of aliphatic fatty monoesters. The phase transformation path was investigated with temperature-time resolved X-ray diffraction during stepped isothermal crystallization, and while cooling from the melt at a fixed rate. Startling differences in phase behavior were uncovered between the isomers. When stepped isothermals were used, selective extinctions occurred at a transition temperature for JLE-281 but not for JLE-282. The extinctions, which are due to dramatic changes in the electronic density of certain families of planes, indicate a phase transition attributed to a brusque rearrangement of the oxygen atoms in the crystal subcell. The phase transition did not occur when the JLEs were cooled continuously. The crucial role played by the position of the alkyl chain and its orientation relative to the easy rotation site of the C–O bond in the phase trajectories of the JLEs was particularly highlighted. View Full-Text
Keywords: jojoba-like wax esters; symmetry; terminal double bond; X-ray diffraction; differential scanning calorimetry; crystallization; crystal structure; polymorphism jojoba-like wax esters; symmetry; terminal double bond; X-ray diffraction; differential scanning calorimetry; crystallization; crystal structure; polymorphism
MDPI and ACS Style

Bouzidi, L.; Li, S.; Narine, S.S. Lubricating and Waxy Esters. VI. Effect of Symmetry about Ester on Crystallization of Linear Monoester Isomers. Symmetry 2014, 6, 655-676.

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