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Melting Points and Viscosities of Fatty Acid Esters that are Potential Targets for Engineered Oilseed
Author(s) -
Yao Linxing,
Hammond Earl,
Wang Tong
Publication year - 2008
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-007-1159-9
Subject(s) - melting point , oleyl alcohol , chemistry , alcohol , isopropyl alcohol , candida antarctica , fatty alcohol , organic chemistry , viscosity , solvent , isopropyl , oleic acid , lipase , materials science , enzyme , biochemistry , composite material
Our previous isolation of branched‐chain fatty acid (BCFA) methyl esters from lanolin was improved and scaled up. Also, oleate esters of isopropanol, oleyl alcohol and normal alcohols of 1–12 carbons chain lengths were prepared. Esters were made by interesterification with sodium alcoholates and by esterification with Candida antarctica lipase. It proved easier to obtain pure esters by the enzymatic synthesis. Melting points and viscosities over the range of 0–70 °C were determined in order to better identify potential lubricant targets that might be produced by genetically modified oilseed crops. Isopropyl and butyl oleate have melting points of −33 and −32 °C, respectively and viscosities that range from ~17 cp (0 °C) to ~2.5 cp (70 °C). They should have suitable stability for lubricants. BCFA esters had viscosities similar to their straight chain analogs. Viscosities increased with alcohol chain length and decreased with temperature. The dependence of viscosity on temperature was fit with an equation based on Erying’s rate equation. Some esters with branched acid or branched alcohol moieties, and some oleate esters might be utilized as biolubricants or biofuels on the basis of their melting points and viscosities.