Abstract
AbstractThe oxidative cleavage of the CC‐bond converts unsaturated fatty acids to carboxylic and dicarboxylic acids. The only method currently used in oleochemistry is ozonolysis. The high energy consumption of ozonolysis makes a transition‐metal catalyzed alternative with a cheaper secondary oxidant attractive. Here we report new methods for ruthenium‐, rhenium‐ and tungsten‐catalyzed oxidations with peracetic acid and hydrogen peroxide. Whereas the direct oxidative cleavage of internal CC‐bonds still lacks selectivity, two‐step reactions are feasible. The first possibility is to convert natural, internal unsaturated fatty acids to ω‐unsaturated ones. These ω‐unsaturated fatty acids can be cleaved by Ru/acac)3/CH3COOOH or Re2O7/H2O2 with yields up to 80 %. In the second two‐step procedure the fatty acid first is hydroxylated and the diol is cleaved: the overall yield for this method is 80 %, too.
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