Hydrochloric Acid → Azelaic Acid

Participants

Reaction Steps

A mixture of linoleic acid (562.4 mg, 2 mmol) and oleic acid (565.7 mg, 2 mmol) was treated with sodium orthovanadate (18.9 mg, 0.1 mmol) and 30% w/v hydrogen peroxide (6 ml) in tertiary butanol (20 ml) in a manner analogous to that in Example 9. In this example, the pH of the reaction mixture was about 6 to 7 after the addition of catalyst. The pH was adjusted to about 2 to 3 with concentrated hydrochloric acid before heating was commenced. After heating, the resulting product was further processed and analyzed in a manner analogous to that in Example 1. The analytical results showed that essentially all of the linoleic acid had been cleaved to produce hexanoic acid and azelaic acid, whereas only 6% of the oleic acid was cleaved to produce pelargonic acid and azelaic acid.

Provenance & Evidence