Olefin Metathesis Reaction of Oleic Acid in Palm Oil

• Main Author: MARIA GUSTAVINI (NIM : 10513005), EVA
• Format: Final Project
• Language: Indonesia
• Online Access: https://digilib.itb.ac.id/gdl/view/27009
• Institution: Institut Teknologi Bandung

<p align="justify">Petroleum is one of the fuel sources needed by humans. In Indonesia, petroleum productions and reserves are decreasing every year. This is inversely related to the consumption of petroleum in Indonesia which tends to increase every year. Thus, an alternative form of renewable energy required. One of them is by developing alternative energy from vegetable oil with high oleic acid content such as palm oil. This research tried to conduct ethenolysis reaction of commercial palm oil with ethylene gas and second generation Grubbs catalyst. Oleic acid might be a source of hydrocarbon compounds that have characteristics of gasoline, kerosene or diesel by double bond termination reactions and esterification/hydrogenation reactions. The breaking of the oleic acid double bond may be carried out through the reaction of olefin metathesis with the homogeneous catalyst. Oleic acid's olefin metathesis reaction can produce &#945;-olefin compounds which are the starting materials of biofuel compounds because it has characteristics of gasoline and kerosene. Research on renewable energy derived from palm oil is very good to be developed in Indonesia because Indonesia is one of the largest palm oil producing countries in the world. In this reasearch, we conducted an ethenolysis reaction of a commercial palm-cooking oil containing 45% oleic acid ethylene gas and a second generation Grubbs catalyst. As a result, there is a mixture of decene and 9-decenoate compounds as well as other heavy fraction compounds such as 9-octadecene and 9-octadecedioate which are the products of self-metathesis reaction of oleic acid. The separation of the mild fraction of the mixture was carried out through a vacuum distillation using a kuegelrohr apparatus. The distillation is carried out by heating at a temperature of 175oC which is the decene's boiling point. The result was fraction that have characteristics of colorless, viscous, and distinctive smell. The results of H1 NMR (500 MHz) measurements of the product indicate the presence of an internal double bond. This indicates that decene can not be isolated. The mild fraction that was successfully separated is a 9-nonadecene compound. To separate the heavy fractions from the mixture, an esterification reaction of the remaining mixture was carried out with methanol and NaOH catalyst. The result were three products separated by gravity column chromatography with an eluent of n-Hexane: Ethyl acetate = 95:5. The results of H1 NMR (500 Mhz) and C13 NMR (125 MHz) measurements showed that the esterification product is 9-octadecene, methyl palmitate, and methyl-9-octadecedioate.<p align="justify">