Rearrangement of epoxy fatty esters to keto fatty esters

The rearrangement of fatty epoxyesters to ketoesters was studied. The isomerization is carried out in nonaqueous media and is catalyzed by acids. Esters containing one epoxy group per fatty acid chain are isomerized to the corresponding ketones in 70–90% yields using boron fluoride etherate catalyst in boiling dioxane. Conversion to ketonic products is measured either by chromatographic separation followed by IR analysis or by oximation. Principal byproducts are hydroxy derivatives. Fatty esters containing more than one epoxy group/fatty acid chain give low ketone yields. A laboratory of the E. Utiliz. Res. & Dev. Div., ARS, USDA.