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Gas Chromatography–Mass Spectrometric Characterization of Monoalkyl Alkanedioates

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Abstract

Using three different synthetic methods, 48 monoalkyl esters of 6 aliphatic dicarboxylic acids and 8 aliphatic alcohols were synthesized. Despite the method of synthesis, monoalkyl alkanedioates occurred in reaction mixtures along with corresponding dialkyl esters. This was caused both by a reaction mechanism and by possible secondary bimolecular disproportionation in solutions. However, for example, unlike monoalkyl phthalates, monoalkyl esters of aliphatic dicarboxylic acids appeared to be stable during their gas chromatographic separation. In no cases, characteristic chromatographic profiles indicating the decomposition of analytes in the chromatographic column were observed. The simultaneous presence of mono- and dialkyl esters in the samples allowed us to use the correlation of retention indices of mono- and dialkyl esters for their identification because the latter were characterized in more detail, namely, with RI(monoester) = aRI(diester) + b and some similar relations. The chromatographic peaks of monoalkyl alkanedioates (like for all carboxylic acids) on columns with nonpolar stationary phases were highly asymmetric. Their electron ionization mass spectra naturally indicated the presence of no signals of molecular ions. Mass spectra of monomethyl and monoethyl esters differed markedly from those of corresponding dialkyl esters, but they were similar for alcohols with R ≥ C3H7.

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ACKNOWLEDGMENTS

The equipment of the Resource Center “Methods of Analysis of the Composition of Matter” of the Science Park of St. Petersburg State University was used in this work. The authors are grateful to the staff of the center for their assistance.

Funding

This work was supported by ongoing institutional funding. No additional grants to carry out or direct this particular research were obtained.

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Authors and Affiliations

  1. St. Petersburg State University, Institute for Chemistry, 198504, St. Petersburg, Russia

    E. V. Eliseenkov & I. G. Zenkevich

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  1. E. V. Eliseenkov
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  2. I. G. Zenkevich
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Correspondence to I. G. Zenkevich.

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Translated by V. Makhlyarchuk

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Eliseenkov, E.V., Zenkevich, I.G. Gas Chromatography–Mass Spectrometric Characterization of Monoalkyl Alkanedioates. J Anal Chem 78, 1811–1828 (2023). https://doi.org/10.1134/S1061934823130051

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  • DOI: https://doi.org/10.1134/S1061934823130051

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