Esterification of Fatty Acids and Short-Chain Carboxylic
Acids with Stearyl Alcohol and Sterols
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Abstract
Esterification of tall oil fatty
acids by neutral components, such
as stearyl alcohol and sterols, is an undesired reaction; a potential
solution is to eliminate the neutral components by a competing esterification
with short-chain carboxylic acids. Esterification of fatty acids and
short-chain carboxylic acids with stearyl alcohol and sterols was
studied in a laboratory-scale glass reactor in the temperature range
of 60–140 °C. Linoleic acid (LA) was used as a model component
for fatty acid esterification with stearyl alcohol (StOH) and sitosterol
(SitOH). Linoleic acid underwent esterification with stearyl alcohol
and sitosterol. In the presence of short-chain carboxylic acids, such
as formic and acetic acid, the esterification of linoleic acid by
stearyl alcohol was efficiently suppressed because stearyl alcohol
reacted with the short-chain carboxylic acid. Formic acid catalyzed
the formation of dienes from sitosterol and campesterol. The esterification
and dehydration processes were verified by gas chromatographic analysis
and extensive kinetic studies. Mathematical models for esterification
and dehydration were developed and successfully applied to a selected
part of experimental data