Skip to main content
SpringerLink
Log in

Chromatographic and chromatospectral characteristic of dicarboxylic acid monoesters

  • Articles
  • Published:
Journal of Analytical Chemistry Aims and scope Submit manuscript

Abstract

Monoalkyl esters of benzene-1,2-dicarboxylic (phthalic) acid have not been reliably characterized by analytical parameters for their chromatographic and chromatospectral identification. Mass spectra of a series of monoalkyl phthalates (R = C1–C8) are discussed; their gas chromatographic retention indices on the RTX-5 polydimethylsiloxane stationary phase (5% phenyl groups) are determined. A linear dependence of indices on the number of carbon atoms in n-alkyl fragments of molecules and a correlation between the indices of any monoalkyl phthalates and corresponding diesters were used for the control of the data obtained. Using the last correlation, we found that most part of index values of mono (2-ethylhexyl) phthalate given in literature is wrong and, therefore, the results of identification of this compound in various samples must be revised. It was found that simplest monoalkyl phthalates are unstable during gas chromatographic separation, which may result in distortions of their mass spectra. To compare with monoalkyl phthalates, a similar series of monoesters of (Z)-butenedioic (maleic) acid was characterized. Retention indices of monoalkyl phthalates in reversed phase HPLC were determined and discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. The NIST 14 Mass Spectral Library (NIST14/2014/ EPA/NIH). http://webbook.nist.gov. Cited April, 2016.

  2. Krylov, V.A., Volkova, V.V., and Zaitsev, S.D., Analitika Kontrol’, 2013, vol. 17, no. 3, p. 295.

    Google Scholar 

  3. Krylov, V.A. and Volkova, V.V., Vestn. Nizhegorod. Univ., 2014, nos. 1–2, p. 210.

    Google Scholar 

  4. Cao, X.-L., Compr. Rev. Food Sci. Food Saf., 2010, vol. 9, no. 1, p. 21.

    Article  CAS  Google Scholar 

  5. Khalil, M.M.H., Gomaa, A.M., Sebaei, A.S., and Moustapha, N.M., J. Essent. Oil-Bear. Plants, 2014, vol. 16, no. 6, p. 1343.

    Article  Google Scholar 

  6. Di Bella, G., Saitta, M., Pellegrino, M., Salvo, F., and Dugo, G., J. Agric. Food Chem., 1999, vol. 47, no. 3, p. 1009.

    Article  Google Scholar 

  7. Manayi, A., Kurepaz-Mahmoodabadi, M., Gohari, A.R., Ajani, Y., and Saeidnia, S., Daru, J. Pharm. Sci., 2014, vol. 28, p. 6.

    Google Scholar 

  8. Niino, T., Ishibashi, T., Itho, T., Sakai, S., Ishiwata, H., Yamada, T., and Onodera, S., J. Health Sci., 2001, vol. 47, no. 3, p. 318.

    Article  CAS  Google Scholar 

  9. Yoshikawa, K., Tanaka, A., Yamaha, T., and Kurata, H., Food Chem. Toxicol., 1983, vol. 21, no. 2, p. 221.

    Article  CAS  Google Scholar 

  10. Kluwe, W.M., Environ. Health Perspect., 1986, vol. 65, p. 271.

    CAS  Google Scholar 

  11. Hara, H., Stewart, G.R., and Mohn, W.W., Appl. Environ. Microbiol., 2010, vol. 76, no. 5, p. 1516.

    Article  CAS  Google Scholar 

  12. Metabolites of Phthalates and Phthalate Alternatives, Method no. 6306.04, Lab. Proc. Manual. Nat. Center for Environ. Health, 2013.

  13. Zenkevich, I.G. and Fakhretdinova, L.N., Analitika Kontrol’, 2015, vol. 19, no. 2, p. 175.

    Google Scholar 

  14. Zenkevich, I.G., Rotaru, K.I., Selivanov, S.I., and Kostikov, R.R., Vestn. S.-Peterb. Univ., Ser. 4: Fiz., Khim., 2015, vol. 2, no. 4, p. 386.

    Google Scholar 

  15. Sukhikh, A.S., Kuznetsov, P.V., and Teslov, L.S., Khim. Rastit. Syr’ya, 2014, no. 3, p. 159.

    Google Scholar 

  16. Bagavathi, P.E. and Ramasamy, N., Pharmacogn. Res., 2012, vol. 14, p. 11.

    Google Scholar 

  17. Syeda, F.A., Habib-ur-Rahman, Choudahry, M.I., and Atta-ur-Rahman, Int. J. Genetics Mol. Biol., 2011, vol. 3, p. 95.

    Google Scholar 

  18. Kawakami, T., Isama, K., and Matsuoka, A., J. Environ. Sci. Health, 2011, vol. 46, p. 855.

    Article  CAS  Google Scholar 

  19. Sadaskava, C.T., Sharanappa, P., Remashree, A.B., Raghu, A.V., Udayan, P.S., and Balachandran, I., Adv. Biol. Res., 2010, vol. 4, no. 6, p. 301.

    Google Scholar 

  20. Chen, H., Yang, Y., Xue, J., Wei, J., Zhang, Z., and Chen, H., Molecules, 2011, vol. 16, p. 4884.

    Article  CAS  Google Scholar 

  21. Bai, X., Chen, Y., Chen, W., Lei, H., and Shi, G., Mar. Drugs, 2011, vol. 9, p. 863.

    Article  CAS  Google Scholar 

  22. Adebayo, M.A., Lawal, O.A., Sikiru, A.A., Ogunwande, I.A., and Avoseh, O.N., Am. J. Plant Sci., 2014, vol. 5, p. 2448.

    Article  Google Scholar 

  23. Zhang, Z., Han, X.-M., Wei, J.-H., Xue, J., Yang, Y., Liang, L., Li, X.-J., Guo, Q.-M., Xu, Y.-H., and Gao, Z.-H., J. Braz. Chem. Soc., 2014, vol. 25, no. 1, p. 20.

    Google Scholar 

  24. Nadaf, M., Halimi, M., and Morfazavi, M., Middle East J. Sci. Res., 2012, vol. 11, no. 2, p. 221.

    CAS  Google Scholar 

  25. Kim, N.S. and Lee, D.-S., Anal. Sci., 2001, vol. 17, p. a383.

    CAS  Google Scholar 

  26. Joshi, S., Mishra, D., Bisht, G., and Khetwalk, S., EXCLI J., 2011, vol. 10, p. 274.

    Google Scholar 

  27. Zenkevich, I.G., Anal. Bioanal. Chem., 2013, vol. 405, p. 3075.

    Article  CAS  Google Scholar 

  28. Zenkevich, I.G. and Fakhretdinova, L.N., Analitika Kontrol’, 2015, vol. 19, no. 1, p. 52.

    Google Scholar 

  29. Zenkevich, I.G. and Fakhretdinova, L.N., J. Anal. Chem., 2016, vol. 71, no. 4, p. 402.

    Article  CAS  Google Scholar 

  30. Zenkevich, I.G., J. Anal. Chem., 2010, vol. 65, no. 3, p. 267.

    Article  CAS  Google Scholar 

  31. Heberger, K. and Zenkevich, I.G., J. Chromatogr. A, 2010, vol. 1217, p. 2895.

    Article  CAS  Google Scholar 

  32. Lebedev, A.T., Mass-spektrometriya v organicheskoi khimii (Mass Spectrometry in Organic Chemistry), Moscow: Tekhnosfera, 2015, 2nd ed.

    Google Scholar 

  33. Practical Gas Chromatography: A Comprehensive Reference, Dettmer-Wilde, K. and Engewald, W., Eds., Heidelberg: Springer, 2014.

  34. Kornilova, T.A., Ukolov, A.I., Kostikov, R.R., and Zenkevich, I.G., Russ. J. Gen. Chem., 2012, vol. 82, no. 10, p. 1675.

    Article  CAS  Google Scholar 

  35. Kornilova, T.A., Ukolov, A.I., Kostikov, R.R., and Zenkevich, I.G., Rapid Commun. Mass Spectrom., 2013, vol. 27, p. 461.

    Article  CAS  Google Scholar 

  36. Ritchie, P.D., J. Chem. Soc., 1935, p. 1054.

    Google Scholar 

  37. Leo, A., J. Chem. Soc., Perkin Trans. 2, 1983, p. 825.

    Google Scholar 

  38. Lu, P.-Y. and Metcalf, R., Environ. Health Perspect., 1975, vol. 10, p. 269.

    Article  CAS  Google Scholar 

  39. Zenkevich, I.G., Zh. Prikl. Khim., 1995, vol. 68, no. 8, p. 1321.

    CAS  Google Scholar 

  40. Zenkevich, I.G. and Guschina, S.V., Russ. J. Phys. Chem. A, 2011, vol. 85, no. 9, p. 1641.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, St. Petersburg State University, St.-Petersburg, 198504, Russia

    I. G. Zenkevich & L. N. Fakhretdinova

Authors
  1. I. G. Zenkevich
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. N. Fakhretdinova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. G. Zenkevich.

Additional information

Original Russian Text © I.G. Zenkevich, L.N. Fakhretdinova, 2016, published in Zhurnal Analiticheskoi Khimii, 2016, Vol. 71, No. 12, pp. 1296–1307.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zenkevich, I.G., Fakhretdinova, L.N. Chromatographic and chromatospectral characteristic of dicarboxylic acid monoesters. J Anal Chem 71, 1204–1214 (2016). https://doi.org/10.1134/S106193481612011X

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S106193481612011X

Keywords

Search

Navigation