Synthesis, Purification, and Quantification of Fatty Acid Ethyl Esters After trans-Esterification of Large Batches of Tobacco Seed Oil

Abstract

Summary The goal of the study was to quantify fatty acid ethyl esters (FAEE’s) produced from two large batches of tobacco seed oil after trans-esterification by heating in ethanol with sulfuric acid catalyst. Purification of the combined ethyl ester reaction products by removing as much of the color and odor from the final product as possible was achieved via conventional column chromatography with amorphous silica and tandem elution of first hexane and then ethyl alcohol as the mobile phase. Gas chromatography was used to quantify specific FAEE’s in the purified material. Recovery of pure FAEE's in batch #1 was near 87%; while, recovery of FAEE’s in batch #2 was greater than 89% with mass yields greater than 400 g of ethyl esters per esterification trial. The FAEE’s possessed no detectable aroma and only a slight yellow color after this chromatographic treatment. Supercritical fluid chromatography with a mobile phase of methanol/acetonitrile modified carbon dioxide and an octadecyl bonded silica stationary phase were used to characterize the purity of each batch of fatty acid ethyl ester product. No free fatty acids nor glycerolrelated impurities were detected in the purified transesterified product.This is the first report describing the optimized trans-esterification of tobacco seed oil on a relatively large scale coupled with subsequent purification and isolation of the resultant ethyl esters. [Beitr. Tabakforsch. Int. 26 (2015) 205-213]