Abstract
The chromatographic analysis of food products for trans isomers of monounsaturated fatty acids, which are harmful components, in the presence of an excess of useful cis isomers is considered as a complex problem of considerable current interest. The separation of substances by gas–liquid chromatography occurs in accordance with two mechanisms with different selectivity for geometric isomers based on adsorption on a flat surface, which gives an energy advantage to trans isomers, and distribution in the bulk phase, which leads to the stronger retention of cis isomers. The theoretical model proposed previously to explain the distribution of an adsorbate as its “absorption” by a stationary-phase macromolecule due to a conformational rearrangement in the course of nonspecific interaction was supplemented by polar interactions and hydrogen bonds. The factors influencing the selectivity of a phase for geometric isomers were considered. A theoretical analysis of the experimental data was carried out and the parameters of stationary phases required for increasing the separation selectivity of the trans and cis isomers of fatty acid esters were determined.
Similar content being viewed by others
REFERENCES
Libby, P., Ridker, P.M., and Hansson, G.K., Nature, 2011, vol. 473, p. 317.
Liu, A.G., Ford, N.A., Hu, F.B., Zelman, K.M., Mozaffarian, D., and Kris-Etherton, P.M., Nutr. J., 2017, vol. 16, p. 53.
Méndez-Cid, F.J., Centeno, J.A., Martínez, S., and Carballo, J., J. Food Compost. Anal., 2017, vol. 63, p. 121.
Rudakov, O.B. and Rudakova, L.V., Pererab. Moloka, 2019, no. 3, p. 37.
Song, J., Park, J., Jung, J., Lee, C., Gim, S.Y., Ka, H., and Lee, J., Toxicol. Res., 2015, vol. 31, no. 3, p. 307.
David, F., Sandra, P., and Vickers Allen, K., Column Selection for the Analysis of FAME: Application, Agilent Technologies, 2005, p. 12. www.agilent.com/cs/library/applications/5989-3760EN.pdf.
Delmonte, P., Kia, A.-R.F., Hu, Q., and Rader, J.I., J. AOAC Int., 2009, vol. 92, no. 5, p. 1310.
Rousova, J., Konschnik, J., Adams, S., Sellers, K., de Zeeuw, J., and English, C., Poster at the AOAC’s Annual Meeting, Toronto, 2018. www.restek.com/pdfs/aoac2018_jrfames_poster.pdf. Accessed May 20, 2020.
Kiran, C., Ravi Reshma, M.V., and Sundaresan, A., Grasas Aceites (Sevilla, Spain), 2013, vol. 64, p. 95.
Shantha, N.C., J. Chromatogr. A, 1992, vol. 624, p. 37.
Mjøs, S.A. and Pettersen, J., Improved Methods for Analysis of Fatty Acid Isomers, Fyllingsdalen, Norway: SSF, 2001.
Precht, D. and Molkentin, J., Nahrung, 1999, vol. 43, no. 4, p. 233.
Ecker, J., Scherer, M., Schmitz, G., and Liebisch, G., J. Chromatogr. B: Anal. Technol. Biomed. Life Sci., 2012, vol. 897, p. 98.
Dubois, N., Barnathan, G., Gouygoul, J.-P., and Berge, J.-P., Eur. J. Lipid Sci. Technol., 2009, vol. 111, p. 688.
Avgul’, N.N., Kiselev, A.V., and Poshkus, D.P., Adsorbtsiya gazov i parov na odnorodnykh poverkhnostyakh (Adsorption of Gases and Vapors on Homogeneous Surfaces), Moscow: Khimiya, 1975.
Simkin, B.Ya. and Sheikhet, I.I., Kvantovokhimicheskaya i statisticheskaya teoriya rastvorov. Vychislitel’nye metody i ikh primenenie (Quantum-Chemical and Statistical Theory of Solutions: Computational Methods and Their Application), Moscow: Khimiya, 1989.
Dolgonosov, A.M. and Prudkovskii, A.G., Sorbtsionnye Khromatogr. Protsessy, 2010, vol. 10, no. 6, p. 887.
Dolgonosov, A.M. and Prudkovskii, A.G., Sorbtsionnye Khromatogr. Protsessy, 2011, vol. 11, no. 1, p. 23.
Grosberg, A.Yu. and Khokhlov, A.R., Statisticheskaya fizika makromolekul (Statistical Physics of Macromolecules), Moscow: Nauka, 1989.
Dolgonosov, A.M., J. Phys. Chem. B, 1998, vol. 102, no. 24, p. 4715.
Dolgonosov, A.M., Model’ elektronnogo gaza i teoriya obobshchennykh zaryadov dlya opisaniya mezhatomnykh sil i adsorbtsii (Electron Gas Model and Generalized Charge Theory for Describing Interatomic Forces and Adsorption), Moscow: Knizhnyi Dom LIBROKOM, 2009.
Dolgonosov, A.M., J. Struct. Chem., 2019, vol. 60, no. 11, p. 693. https://doi.org/10.1134/S0022476619110015
Dolgonosov, A.M., Russ. J. Inorg. Chem., 2017, vol. 62, no. 3, p. 344. https://doi.org/10.1134/S0036023617030068
Dolgonosov, A.M., Russ. Chem. Bull., 2016, vol. 65, no. 4, p. 952.
Dolgonosov, A.M. and Zaitceva, E.A., J. Struct. Chem., 2020, vol. 61, no. 8, p. 1233. https://doi.org/10.1134/S0022476620080089
Heckers, H., Dittmar, K., Melcher, F.W., and Kalinowski, H.O., J. Chromarogr. A, 1977, vol. 13, no. 5, p. 93.
Matei, V., Comănescu, I., and Borcea, A.-F., Stationary phases. https://srigc.com/cn/downloads/169/InTech-Stationary_phases.pdf. Accessed May 10, 2020.
Application Specific GC Columns: Select FAME Columns. www.agilent.com/en/product/gc-columns/application-specific-gc-columns/select-fame-columns. Accessed May 10, 2020.
Gas Chromatography: Supelco. www.supelco. com.tw/A-1%20%20%20207-235%20New.pdf. Accessed May 10, 2020.
Funding
This work was supported by the Russian Foundation for Basic Research (grant no. 18-03-00382a).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated by V. Makhlyarchuk
Rights and permissions
About this article
Cite this article
Dolgonosov, A.M., Zaitceva, E.A. Factors Determining the Selectivity of Stationary Phases for Geometric Isomers of Fatty Acids in Gas–Liquid Chromatographic Analysis. J Anal Chem 75, 1599–1607 (2020). https://doi.org/10.1134/S1061934820120072
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1061934820120072