Olefins can be found in nature as terpenes or unsaturated fatty acids, which are derived from vegetable oils and animal fats. Such alkenes can be oxidatively cleaved into mono- or dicarbonyls, i.e. aldehydes or carboxylic acids, which can be used in polymer, plasticizer and stabilizer production. These products are also useful as intermediate building blocks for subsequent reactions.
Expensive and often toxic transition-metal complexes derived from Ru, W or Os are known to catalyse these specific oxidative cleavages, with the help of reactive and relatively hazardous oxidants like NaIO4 or ozone. First-row transition-metal complexes are only known to cleave very activated substrates like styrene-derivatives. Permanganate may also be used for these reactions, yet it has to be used in stoichiometric amounts.
Here, we present a study towards the use of more benign methods to oxidatively cleave internal double bonds, using Fe-catalysts and hydrogen peroxide in the oxidative cleavage of unsaturated fatty acids. Ultimately, such procedures can be seen as green alternatives for the production of chemical building blocks from renewable vegetable oils and animal fats.