Igor G. Zenkevich, Lilia N. Fakhretdinova


The literature data indicates that the results of gas chromatographic analysis of such low-volatile polar compounds as aliphatic dicarboxylic acids are characteri­zed by high irreproducibility. Most of the previously published GC retention indices seem to be very spread out and appear to be erroneous. Similar irreproducibility is typical for some other physicochemical properties of these acids, namely melting temperatures, water solubility, etc. The experimental testing of the possibilities of gas chromatographic and/or GC-MS analysis of simplest dicarboxylic acids using standard non-polar polydimethylsiloxane stationary phases (BPX-1, RTX-5) has been fulfilled.  It indicates that some com­po­unds of this series (e.g., glutaric acid) are determined without decomposition, for others the interaction with solvent is typical (oxalic acid), and in some cases the single compounds observed are the products of thermal destruc­tion (citric acid). Namely, the analysis of the solution of oxalic acid in isopropyl alcohol permits us to detect two esters – monoisopropyl and diisopropyl oxalates.

Keywords: Aliphatic dicarboxylic acids, gas chromatographic analysis, irreproducibility, thermal decomposition.


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Svoistva organicheskikh soedinenii. Spravochnik Properties of organic compounds. Reference book A.A. Potekhin (Ed.) Leningrad, Khimiia, 1984, 519 p. (in Russian).

http://www.chemicalland21.com/industrialchem/organic/*%20ACID.htm (accessed 15 December 2014) .

Zenkevich I.G. Derivatization of Analytes in Chromatography: General Aspects. Encyclopedia of Chromatography. 3rd Edn., New York, Taylor & Francis, 2010, 2850 p., V. 1, pp. 562-566.

Zenkevich I.G. General relations holding in variations of physical properties of organic compounds within homologous series. Zhurnal organicheskoi khimii Rus. J. Org. Chem., 2006, vol. 42, no. 1, pp. 9-20. doi: 10.1134/S1070428006010015.

Zenkevich I.G. Application of recurrent relations in chemistry. J. Chemo¬metr., 2010, vol. 24, pp. 158-167. doi: 10.1002/cem.1297.

Zenkevich I.G. Prevention of a dangerous tendency in the presentation of the results of GC-MS identi¬fication. Anal. Bioanal. Chem., 2013, vol. 405, pp. 3075-3083. doi: 10.1007/s00216-013-6751-2.

Setkova L., Risticevic S., Pawliszyn J. Rapid headspace solid-phase micro¬extraction – gas chromatographic – time-of-flight mass spectrometric method for qualitative profiling of ice wine volatile fraction II: Classifica¬ti¬on of Canadian and Czech ice wine using statistical evaluation of the data. J. Chromatogr. A., 2007, vol. 1147, pp. 224-240. doi: 10.1016/j.chroma.2007.02.052.

The NIST 11 Mass Spectral Library (NIST11/2011/EPA/NIH). Software/Data Version (NIST08); NIST Standard Reference Database, Number 69, August 2011. National Institute of Standards and Techno¬logy, Gaithersburg, MD 20899. http://webbook.nist.gov (accessed 15 December 2014).

Ardrey R.E., Moffat A.C. Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase. J. Chromatogr., 1981, vol. 220, no. 3, pp. 195-252.

Bajpai V.K., Al-Reza S.M., Choi U.L., Lee J.H., Kang S.C. Chemical composition, antibacterial and antioxidant activities of leaf essential oil and extracts of Metasequioa glyptostroboides Miki ex Hu. Food Chem. Toxicol., 2009, vol. 47, no. 8, pp. 1876-1883. doi: 10.1016/j.fct.2009.04.043.

Ganjali A., Harati M.P. Antimicrobial effect of essential oil of Artemisia kermanensis on water by HPC method. Abstr. Int. Conf. on Agriculture, Chemical and Environmental Sci. (ICACES 2012), Dubai, 2012, pp. 66-68.

Escalona-Arranz J.C., Perez-Roses R., Jimenez I.L., Rodriguez-Amado J., Argota-Coello H., Canizares-Lay J., Morris-Quevedo H.J., Sierra-Gonzales G. Chemical constituents of Tamarindus indica L. leaves. Rev. Cubana Chem., 2010, vol. 22, no. 3, pp. 65-71.

Pedersen D.U., Durant J.L., Taghizadeh K., Hemond H.F., Lafleur A.L., Cass G.R. Human cell mutagenes in respirable airborne particles from the Northeastern United States. 2. Quantification of mutagenes and other organic compounds. Environ. Sci. Technol., 2005, vol. 39, no. 24, pp. 9547-9560. doi: 10.1021/es050886c.

Kotowska U., Zalikowski M., Isidorov V.A. HS-SPME/GC-MS analysis of volatile and semi-volatile organic compounds emitted from municipal sewage sludge. Environ. Monit. Asses., 2012, vol. 184, no. 5, pp. 2893-2907. doi: 10.1007/s10661-011-2158-8.

Uysal S., Ceylan R., Zengin G., Aktumsek A., Zengin N., Guler G.O., Yidiztugay E., Karatas S. Phytochemical characterization of an endemic plant foodstuff in Turkey: Centaurea urvillei subsp. stepposa and its antioxidant properties. Int. Res. J. Pharmacy, 2014, vol. 5, no 8, pp. 646-652. doi: 10.7897/2230-8407.0508132.

Berninger H., Moller M.R. Retentionsindices zur gaschromatographischen identifizierung von Arzneimitteln. Arch. Toxicol., 1977, vol. 37, pp. 295-305.

Perrigo B.J., Peel H.W. The use of retention indices and temperature-programmed gas chromatography in analytical toxicology. J. Chromatogr. Sci., 1981, vol. 19, pp. 219-226.

Japp M., Gill R., Osselton M.D. Comparison of drug retention indices determined on packed, wide bore capillary and narrow bore capillary columns. J. Forensic Sci., 1987, vol. 32, no. 6, pp. 1574-1586.

Sharp M.E. A rapid screening procedure for acidic and neutral drugs in blood by high resolution gas chromatography. J. Anal. Toxicol., 1987, vol. 11, pp. 8-11.

Peng C.T., Ding S.F., Hua R.L., Yang Z.C. Prediction of retention indices. I. Structure-retention index relationship on apolar columns. J. Chromatogr. A, 1986, vol. 436, pp. 137-172.

Shakirov L.G., Tsypysheva L.G., Suleimanova R.A., Najmushin A.I., Tsypyshev O.Yu. Gas chromatographic determination of the products of the synthesis of chlorosubstituted salicylic acids. Zhurnal Analiticheskoi Khimii Rus. J. Anal. Chem., 1988, vol. 43, no. 1, pp. 143-146 (in Russian).

Sa M.B., Rakph M.T., Nascimento D.C.O., Ramos C.S., Barbosa I.M.S., Sa F.B., Lina-Filho J.V. Phytochemistry and preliminary assessment of the anti¬bacterial activity of chloroform extract of Amburana cearensis (Allemao) A.C. Sm. against Klebsiela pneumoniae Carbapenemase-producing strains. Evidence-based Complimentary and Alternative Medicine, vol. 2014, Article ID 786586, 7 p. doi: 10.1155/2014/786586.

Barry E.F., Grob R.L. Columns for Gas Chromatography: Performance and Selection, Hoboken, NJ, John Wiley & Sons Inc., 2007, 298 p.

Kourkoutas Y., Kandylis P., Panas P., Dooley J.S.G., Nigam P., Koutinas A.A. Evaluation of freeze-dried kefir coculture as starter in feta-type cheese production. Appl. Environ. Microbiol., 2006. vol. 72, no. 9, pp. 6124-6135. doi: 10.1128/AEM.03078-05.

Freidlin G.N. Aliphaticheskie dikarbonovye kisloty Aliphatic dicarboxylic acids. Moscow, 1978, 263 p. (in Russian).

Barbooti M.M., Al-Sammerrai D.A. Thermal decomposition of citric acid. Thermochimica Acta, 1986, vol. 98, pp. 119-126.

Harrison B.M., Priest F.G. Composition of peats used in the preparation of malt for Scotch whisky production – influence of geographical source and extraction depth. J. Agric. Food Chem., 2009, vol. 57, no. 6, pp. 2385-2391. doi: 10.1021/jf803556c.

Brandi F., Bar E., Mourgues F., Horvath G., Turcsi E., Giuliano G., Liverani A., Tartarini S., Lewinsohn E., Rosati C. Study of Redhaven peach and its white-fleshed mutant suggests a key role of CCD4 carotenoid dioxygenase in carotenoid and norisoprenoid volatile metabolism. BMC Plant Biol., 2011, vol. 11, no. 24, pp. 1-14. doi: 10.1186/1471-2229-11-24.


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