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Manufacture of C13 higher fatty acids from their esters by carbonylation of dodecene-1 in ionic liquid medium

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Abstract

The effect of catalyst nature, temperature, acidity, promoters, and feedstock composition on dodecene-1 carbonylation in the presence of Pd compounds in an ionic liquid medium yielding higher fatty acid and their esters was studied. Palladium salts without phosphine ligands show high activity in tetrabutylammonium bromide. In systems of this kind, the catalyst is suspended in the reaction mass in the form of Pd particles with a size of 4–10 nm. It was shown that the catalytic system can be repeatedly used without loss of activity. It is acceptable to use synthesis gas instead of bare carbon monoxide with the selectivity for tride-canoic acid increasing.

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References

  1. S. V. Adel’son, T. P. Vishnyakova, and Ya. M. Paushkin, Petrochemical Synthesis Technology (Khimiya, Moscow, 1985) [in Russian].

    Google Scholar 

  2. P. Hofmann and W. Muller, Hydrocarbon Process. 60, 151 (1981).

    CAS  Google Scholar 

  3. P. Hofmann, K. Kosswig, and W. Schaefer, Ind. Eng. Chem. Res. 19, 330 (1980).

    Article  CAS  Google Scholar 

  4. C. D. Frohning and C. W. Kohlpaintner, in Applied Homogeneous Catalysis with Organometallic Compounds (VCH, New York), Vol. 1, p. 29.

  5. J. March, Advanced Organic Chemistry, 4th Ed (Wiley, New York, 1992).

    Google Scholar 

  6. R. A. Sheldon, Chemicals from Synthesis Gas (D.Reidel, Dordrecht, 1983; Khimiya, Moscow, 1987).

    Google Scholar 

  7. G. Kiss, Chem. Rev. 101, 3435 (2001).

    Article  CAS  Google Scholar 

  8. B. M. Trost, Angew. Chem., Int. Ed. Engl. 34, 259 (1997).

    Article  Google Scholar 

  9. A. L. Lapidus, O. L. Eliseev, N. N. Stepin, and T. N. Bondarenko, Izv. Akad. Nauk, Ser. Khim., No. 11, 2458 (2004).

  10. O. L. Eliseev, N. N. Stepin, T. N. Bondarenko, and A. L. Lapidus, Dokl. Akad. Nauk 401, 486 (2005).

    Google Scholar 

  11. A. Lapidus, O. Eliseev, T. Bondarenko, and N. Stepin, J. Mol. Catal. A: Chem. 252, 245 (2006).

    Article  CAS  Google Scholar 

  12. A. O. King and E. Negishi, J. Org. Chem. 43, 358 (1978).

    Article  CAS  Google Scholar 

  13. L. Malatesta and M. Angoletta, J. Chem. Soc., 186 (1957).

  14. D. R. Coulson, Inorg. Synth. 13, 121 (1972).

    Article  Google Scholar 

  15. M. S. Kharasch, R. C. Seyler, and F. R. Mayo, J. Am. Chem. Soc. 60, 882 (1938).

    Article  CAS  Google Scholar 

  16. D. M. Fenton, J. Org. Chem. 38, 3192 (1973).

    Article  CAS  Google Scholar 

  17. T. E. Kron, Yu. G. Noskov, M. I. Terekhova, and E. S. Petrov, Russ. J. Phys. Chem 70, 76 (1996).

    Google Scholar 

  18. A. D. Karpyuk, N. D. Kolosova, M. I. Terekhova, et al., Izv. Akad. Nauk SSSR, Ser. Khim., 2291 (1984).

  19. A. D. Karpyuk, M. I. Terekhova, N. D. Kolosova, et al., Izv. Akad. Nauk SSSR, Ser. Khim., 639 (1985).

  20. J. F. Knifton, J. Org. Chem. 41, 2885 (1976).

    Article  CAS  Google Scholar 

  21. M. T. Reetz and J. G. de Vries, Chem. Commun., 559 (2004).

Download references

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Authors and Affiliations

  1. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia

    A. L. Lapidus, O. L. Eliseev & T. N. Bondarenko

  2. Gubkin State University of Oil and Gas, Moscow, Russia

    N. H. Chau

Authors
  1. A. L. Lapidus
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  2. O. L. Eliseev
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  3. T. N. Bondarenko
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  4. N. H. Chau
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Correspondence to A. L. Lapidus.

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Original Russian Text © A.L. Lapidus, O.L. Eliseev, T.N. Bondarenko, N.H. Chau, 2010, published in Neftekhimiya, 2010, Vol. 50, No. 6, pp. 452–458.

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Lapidus, A.L., Eliseev, O.L., Bondarenko, T.N. et al. Manufacture of C13 higher fatty acids from their esters by carbonylation of dodecene-1 in ionic liquid medium. Pet. Chem. 50, 442–449 (2010). https://doi.org/10.1134/S096554411006006X

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  • DOI: https://doi.org/10.1134/S096554411006006X

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