III International Conference

SYNTHESIS OF OXIRANES FROM RENEWABLE RAW MATERIALSCOMPONENTSPP-II-112Selivanova N.V., Khlebnikova T.B., Mattsat Yu.V., Tolstikov A.G., Pai Z.P.Boreskov Institute of Catalysis SB RAS, Novosibirsk, RussiaE-mail: natas@catalysis.ruUtilization of renewable raw materials, such as industrial wood residue, offerspossibilities of manufacturing of epoxy compounds of commercial value. The field ofapplication of epoxides is rather wide. Epoxides are efficient plasticizers (modifiers,stabilizing agents and diluents) of plastics and epoxy resins as well as preqursors in thesynthesis of different pharmaceutical products [1]. One of the most promising processes forpreparing of epoxides from raw materials is the method of phase-transfer catalysis, providingdirect oxidation of different organic substrates in the presence of peroxopolyoxotungstatebased catalysts [2].The present work reports screening of substrates of different nature (unsaturated aliphaticcompounds, terpenoids and coumarins) in the reaction of oxidation by H 2 O 2 in a two-phasesolution in the presence of methyltri-n-octylammonium tetrakis(oxodiperoxotungsto)-phosphate.It was established that epoxidation of oleic and ricinoleic acids and their ethers provides90 % selectivity with respect to epoxide.Epoxidation of coumarins was performed using peucedanin as an example. It wasoxidized to yield unstable epoxide, which transforms into ketol hydroxyoreozelon underreaction conditions.The process of oxidation of natural terpenoids (such as betulin isolated from birch bark)results in the formation of a number of products, including epoxide, the yield of which is nothigher than 30 %. By contrast, the oxidation of betulin diacetate provides 90% selectivity withrespect to epoxide.Since the above betulin derivatives exhibit antiphlogistic, antiviral and antineoplasticactivity, they are of profound interest for medicinal chemistry [3].The work was supported by Russian Found of Fundamental Investigations, Grant No 04-03-32425, RAS Integration Project No 5.6.3.369