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Catalytic oxidation of fatty acids. II. Epoxidation and oxidative cleavage of unsaturated fatty acid esters containing additional functional groups

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Abstract

Methyl esters of monounsaturated fatty acids were oxidized with aqueous hydrogen peroxide in biphasic organic-aqueous systems in the presence of catalyst [Me(n-C8H17)3N]3{PO4[WO(O2)2]4}. Epoxidation and oxidative cleavage of the C=C bond were found to proceed with high conversion and selectivity in the absence of organic solvents and under rather mild conditions (T < 100 °C, 1 atm).

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References

  1. Maerker G, Haeberer ET, Herb SF (1966) J Am Oil Chem Soc 43:505

    Article  CAS  Google Scholar 

  2. Ferrari M, Ghisalberti EL, Pagnoni UM, Pelizzoni F (1968) J Am Oil Chem Soc 45:649

    Article  CAS  Google Scholar 

  3. Ucciani E, Debal A, Rafaralahitsimba G (1993) Fat Sci Technol 95:236

    Google Scholar 

  4. Oakley MA, Woodward S, Coupland K, Parker D, Temple-Heald C (1999) J Mol Catal A 150:105

    Article  CAS  Google Scholar 

  5. Tolstikov GA (1976) Hydroperoxide oxidation reactions. Nauka, Moscow, 200 pp

  6. Venturello C, D’Aloisio R, Bart JCJ, Ricci M (1985) J Mol Catal 32:107

    Article  CAS  Google Scholar 

  7. Ishii Y, Yamawaki K, Ura T, Yamada H, Yoshida T, Ogawa M (1988) J Org Chem 53:3587

    Article  CAS  Google Scholar 

  8. Kozhevnikov IV, Mulder GP, Steveuink-de-Zoete VC, Oostwal MG (1998) Mol Catal A 134:223

    Article  CAS  Google Scholar 

  9. Turnwald SE, Lorier MA, Wright LJ, Mucalo MR (1998) J Mater Sci Lett 17:1305

    Article  CAS  Google Scholar 

  10. Sapegina YV, Selivanova NV, Khlebnikova TB, Pai ZP, Tolstikov AG (2004) Proceedings of the 2nd International Conference on natural products and physiologically active substances (ICNPAS-2004), Novosibirsk, p 107

  11. Sapegina YV, Selivanova NV, Khlebnikova TB, Pai ZP, Tolstikov AG (2005) Proceedings on Russian VIII school conference on organic chemistry, Kazan, p 362

  12. Pai ZP, Tolstikov AG, Berdnikova PV, Kustova GN, Khlebnikova TB, Selivanova NV, Shangina AB, Kostrovskii VG (2005) Russ Chem Bull 54:1847

    Article  CAS  Google Scholar 

  13. Kabanov VA (ed.) (1974) Entziklopediya Polimerov, vol 2. Sovetskaya Entziklopediya, Moscow, p 620

  14. Pai ZP, Khlebnikova TB, Mattsat YV, Parmon VN (2009) React Kinet Catal Lett. doi:10.1007/s11144-009-0069-2

  15. Blau K, Halket JM (1993) Handbook of derivatives for chromatography. Wiley, New York

    Google Scholar 

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Acknowledgements

The work was financially supported by the RAS Program of Basic Research (Project No. 5.7.3, 2009). The authors are grateful to the Russian Foundation for Basic Research for access to the STN International databases via the STN Center at the Institute of Organic Chemistry, Russian Academy of Sciences, Novosibirsk, Russia.

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Correspondence to Tatiana B. Khlebnikova.

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Khlebnikova, T.B., Pai, Z.P., Fedoseeva, L.A. et al. Catalytic oxidation of fatty acids. II. Epoxidation and oxidative cleavage of unsaturated fatty acid esters containing additional functional groups. React Kinet Catal Lett 98, 9–17 (2009). https://doi.org/10.1007/s11144-009-0054-9

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  • DOI: https://doi.org/10.1007/s11144-009-0054-9

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