| Reduction of vernonia oil methyl esters (VOME) into epoxy fatty alcohol and diols was achieved with lithium aluminum hydride (LAH), under reflux and room temperature conditions, by using hexane and tetrahydrofuran (THF) as solvents. The reactions of VOME with LAH in hexane gave cis-12,13-epoxy- cis-9-octadecenol as a major product with an isolated yield of 73.62%, whereas the reactions with LAH in THF gave isomers of 12(13)-hydroxy- cis-9-octadecenol as the major products with an isolated yield of 95.1%. LAH was similarly reacted with vernonia oil (VO) to give the same products. The sodium salt of the epoxy alcohol (sodium alkoxide), was reacted with chloroacetic acid sodium salt at room temperature, in dimethylsulphoxide (DMSO) as a solvent, to give cis-15,16-epoxy-cis -en-3-oxadocosane with an isolated yield of 90.63%, whereas the reaction of the alkoxide with epichlorohydrin gave 1,2,16,17-diepoxy-13-en-4-oxacosane with an isolated yield of 95%. MALDI-TOFMS, 1H-NMR, 13C-NMR, GC/MS, and IR were used to characterize these products. In an effort to develop a simple and relatively time-saving analytical methodology for the dectection of surfactants, MALDI-TOFMS was used for the characterization and detection limits of seventeen commercial nonylphenol ethoxylates all having the general formula 4-(C9H19)-C6H4-(OCH 2CH2)n-OH, including SurfonicRTMN-10, N-31.5, N-40, N-60, N-85, N-95, N-100, N-102, N-120, N-150, N-200, N-300, N-400, N-550, N-700, N-800 and N-1000, using alpha-cyano-4-hydroxycinnamic acid (CHCA) as the matrix. |
