Several explosions have occurred during laboratory distillation of isopropanol [1, 2, 4, 5], some with a sample stored for 5 years in a part empty can
[5]. No cause was apparent, but presence of traces of ketone(s) promoting peroxidation is a probability. Previously, the presence of 0.36M peroxide
had been reported in a 99.5% pure sample of isopropanol stored for several months in a partially full clear glass bottle in strong daylight [3]. The
reformation of peroxides in de-peroxided isopropanol 'within a few days' had been noted [2]. It appears that the tertiary H on the 2-position is
susceptible to autoxidation, and that 2-propanol must be classed as peroxidisable. 2-Hydroperoxy-2-hydroxypropane has, in fact, been isolated from
photocatalysed oxidation of isopropanol. |