Synthesis Synthesis Preparation

Experimental and Methods

Materials

All chemicals and solvents used in this study such as hexane, ethanol, hydrogen peroxide, toluene and acetic acid were analar grade and were used without further purification. Oleic acid (OA), Linoleic acid (LA), p-toluenesulfonic acid (PTSA), oleyl alcohol (OL) and oleoyl chloride (OLC) were acquired from Fisher and Merck.

Synthesis Reactions

Monoepoxidation of Linoleic Acid (MELA) (2)

Linoleic acid (LA) 1 (1.4 g) was fluxed in 10 mL toluene and 120 mg of Novozym 435® lipase was added to the solution. During stirring the reaction for 15 min, 30% H2O2 (15 μL) was added and the addition was repeated every 15 min for 7 h. after complited the reaction the lipase Novozym 435® was filtered and the mixture of

The mixture was heated at 110 ºC and for 7 h. The mixture was washed with the water and was dried by using anhydrous sodium sulphate [18].

Synthesis of oleyl 9,(12)-oleoyloxy-10,(13)-oleioxyoctadecanoate (OLOLOODT) (5)

OLHYOODT 4 (2.5g; 0.003 mol), pyridine (1.66 g; 0.002 mol) and CCl4 (10 mL) were mixed and heated at 60 °C. OLC (16.2 g; 0.013 mol) was adding during 1 h, and the reaction mixture was refluxed for (5.5 h). The mixture was washed with the water and was dried by using anhydrous sodium sulphate [19].

Characterization

FTIR and 1H and 13C NMR

FTIR of the products was recorded on a Perkin Elmer Spectrum GX spectrophotometer in the range 400-4000 cm-1. FTIR was used to measure functional groups of the synthesis products. A very thin film of products was applied to NaCl cells (25 mmi.d × 4 mm thickness) for analysis. 1H and 13C NMR analysis was performed with NMR spectroscopy model Joel FCP 400 MHz with the solvent CDCl3. 1H and 13C NMR of the products were recorded on a Bruker 300 NMR spectrophotometer