Abstract: | Ethylene glycol esters of soybean oil FA increased in viscosity much more slowly than methyl or glycerol esters when oxidized at 105°C in the presence of flowing air and colloidal copper. This increased stability was caused by a minor constituent of the ethylene glycol esters, which was shown by MS to be a mixed ethanediol fatty acylate p-toluenesulfonate (EFAT). The p-toluenesulfonate group came from the catalyst used in the formation of the ethylene glycol esters. EFAT was quantified by UV spectrometry, HPLC, or GC of the acyl group that it contains. EFAT could be synthesized in good yield by reacting ethylene glycol, a FA, and p-toluenesulfonic acid (TSA) in a 1∶1∶1 molar ratio using a benzene azeotrope to remove water of esterification. EFAT increased the time required for the polymerization of soybean oil by about 27 times but required concentrations of 2–5% by weight. EFAT made with a variety of FA were active in delaying viscosity increase. Ethyl and decyl p-toluenesulfonate were inactive. Replacing ethylene glycol by glycerol and 1,2-propylene glycol but not by 1,3-propylene glycol resulted in active EFAT. TSA itself delayed the polymerization of soybean oil, especially in the presence of free ethylene glycol and FA, but this probably was caused by formation of EFAT during the oxidation test. Colloidal copper could be replaced by cupric ion. EFAT-copper appeared to act as an antioxidant by destroying hydroperoxides without initiation of free radical chains. |