Oxidative cleavage of the double bond of monoenic fatty chains in two steps: A new promising route to azelaic acid and other industrial products

We describe a process for the production of azelaic and pelargonic acids an d omega-hydroxynonanoic and pelargonic acids by oxidative cleavage of the d ouble bond of respectively oleic acid and oleyl alcohol in two reaction ste ps. In the first step the monoenic reagents react with hydrogen peroxide in the presence of pertungstic acid, as the catalyst, giving a diol, as the r eaction product, that can be easily separated and purified. The key factors influencing this reaction have been studied. The second step is the oxidat ive cleavage with molecular oxygen of the diol formed in the first step, in the presence of catalyst formed in situ from tungstic acid and cobalt acet ate. The nature of the catalyst, probably a poly(oxametalate), has been stu died; factors affecting conversion and yields have been examined and the po ssible mechanisms discussed.