The kinetics for the epoxidation of methyl esters of palm olein (MEPOL) by peroxyformic acid and peroxyacetic acid generated in situ were studied. The rate-determining step was found to be the formation of peroxy acid. Epoxidized MEPOL (EpMEPOL), with almost complete conversion of the unsaturated carbon and negligible ringopening, can be synthesized by the in situ technique described.The kinetics of the oxirane cleavage of EpMEPOL by acetic acid were studied at various temperatures. The reaction was found to be first-order with respect to the epoxy concentration and second-order to the acetic acid concentration. The activation energy and the entropy of activation for the epoxidation of MEPOL were comparable to those for the oxirane cleavage of EpMEPOL by acetic acid, suggesting that the two reactions are competitive. The success of the epoxidation of MEPOL with only negligible oxirane cleavage is attributed to the heterogeneous nature of the system employed in the in situ technique.

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A variety of esters from the reactions of monoalcohols with palm olein were prepared, epoxidized byin situ peroxyacid techniques, and some of their physical properties were compared. The thermal oxidative stabilities of these esters andbis(2‐ethylhexyl) phthalate were studied. The esters were placed in an oven maintained at 120°C, and the loss of mass and acid, iodine, percent oxirane, hydroxyl, and peroxide values were monitored periodically. The epoxidized esters had higher densities and lower volatilities, and were more resistant toward oxidation than their unepoxidized counterparts. The stability of the oxirane was related to the initial acid value of the sample. Higher initial acid value resulted in a greater decrease in the oxirane content, indicating acid‐catalyzed cleavage of the oxirane ring.

Metathesis of ethyl oleate, catalyzed by WCI6 and SnMe4, provided diethyl 9-octadecenedioate (the desired starting material for the synthesis of civetone) in 99% yield. Dieckmann condensation of diethyl 9-octadecenedioate gave 2-ethoxycarbonyl-9-cycloheptadecenone (63% yield), the hydrolysis-decarboxylation reaction of which yielded civetone (93%). Identification of all products was by 1H nuclear magnetic resonance, infrared and mass spectroscopic data. This is the first report of the synthesis of civetone from palm oil-derived products.KEY WORDS : Civet, civetone, diethyl 9-oetadecenedioate, 2~ethoxycarbonyl-9-cyeloheptadecenone, ethyl oleate, metathesis, palm oil.Civetone (9-cis-cycloheptadecenone), commonly known as

10,11-Dioctyleicosane, a star-shaped hydrocarbon, has been successfully synthesized from 9-octadecene (a product from metathesis of methyl oleate or ethyl oleate) through dimerization followed by hydrogenation. The product was determined by 13C nuclear magnetic resonance spectroscopic and gas chromatography/mass spectrometric techniques. This hydrocarbon likely exhibits lubricating properties that can be used as high-performance functional fluids in automotive lubrication. We also report the presence of a novel product, a trimer that was formed during the synthesis. JAOCS 73, 333-336 (1996).KEY WORDS: Diethyl 9-octadecenedioate, 10,11-dioctyl eicosane, ethyl and methyl oleates, metathesis, 9-octadecene, palm oil, star-shaped hydrocarbon.