Convenient thionation of triglycerides with lawessons reagent

Thionation using the Lawesson’s reagent (LR) led to quantitative and selective replacement of carbonyl groups (C=O) with thionocarbonyl groups (C=S). Mixtures of thionotriglycerides were obtained by reaction of 2,4-bis (p-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide in suspension with triglycerides (TG). With a molar ratio (LR)/(TG)=3∶2, there was complete exchange of C=O with C=S in the carboxylic groups of the TG. The yield is over 90%. The two P=S ligands in the LR confer a double reactivity, producing a high power of thionation. Fourier transform infrared spectroscopy was employed for quantitative and qualitative characterization of the thionated TG and for monitoring the progress of partial or total thionation as conditioned by the molar ratios of the starting compounds. Thus, with molar ration LR/TG of 0.108, 0.36, and 0.72, we obtained around 6, 20, and 40% of C=O conversion, respectively.