Transition-metal Catalyzed Oxidative Cleavage of Unsaturated Fatty Acids

✍ Scribed by Rüsch, M. ;Klaas, Gen. ;Bavaj, P. ;Warwel, S.

• Publisher: John Wiley and Sons
• Year: 1995
• Weight: 700 KB
• Volume: 97
• Category: Article
• ISSN: 0931-5985
• DOI: 10.1002/lipi.19950971002

✦ Synopsis

Transition-metal Catalyzed Oxidative Cleavage of Unsaturated Fatty Acids * M . R u s c h gen. K l a a s . I? B a v a j a n d S . W a r w e / * * Institiit fur Biochrmie und Technologie der Fette, H . I? Kaufrnann-lnstitut, Bundrsanstalt fur Crtreide-, Kartoffelund Fettforschung, Munster The oxidative cleavage of the C=C-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 dircct oxidative cleavage of internal C=C-bonds still lacks selectivity, two-step reactions are feasible. The first possibility is to convert natural. internal unsaturated fatty acids to w-unsaturated ones. These iu-unsaturated fatty acids can be cleaved by Ru/acac),lCH,COOOH or Rc:OdH:O? with ylelds up to 80%.

[n 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.