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Abstract <p>The possibilities of GC–MS identification of the products of free-radical chlorination of cyclic ethers, namely, tetrahydrofuran, 2<i>H</i>-tetrahydropyran, and 1,4-dioxane directly in reaction mixtures (without isolation) are considered. The number of chlorine atoms in these products can be determined unambiguously using electron ionization mass spectra. The complexity of this problem is explained by the large number of possible congeners and isomers (e.g., in the case of 2<i>H</i>-tetrahydropyran, their number is 234), as well as insignificant informational maintenance. The absence of gas chromatographic retention indices (RIs) on standard nonpolar polydimethylsiloxane stationary phases even for simplest chloro derivatives of mentioned cyclic ethers makes impossible the calculation of increments, which allow interpretation of data for more chlorinated products. As a result, the data for compounds of other series (including alicyclic ones, having different conformations) should be used as a rough approximation. Nevertheless, by this way, some simplest products of tetrahydrofuran and 1,4-dioxane chlorination were identified. Besides that, the joint interpretation of mass spectrometric and gas chromatographic data allowed us to identify three from four isomeric hexachloro-1,4-dioxanes.</p>

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Possibilities and Limitations of Gas Chromatography–Mass Spectrometric Identification of Products of Free Radical Chlorination of Cyclic Ethers at the Lack of Reference Information

  • 期刊论文

  • 发表日期：

    2025年12月22日

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  • I. G. Zenkevich,
  • E. V. Eliseenkov,
  • A. I. Ukolov

摘要

Abstract

The possibilities of GC–MS identification of the products of free-radical chlorination of cyclic ethers, namely, tetrahydrofuran, 2H-tetrahydropyran, and 1,4-dioxane directly in reaction mixtures (without isolation) are considered. The number of chlorine atoms in these products can be determined unambiguously using electron ionization mass spectra. The complexity of this problem is explained by the large number of possible congeners and isomers (e.g., in the case of 2H-tetrahydropyran, their number is 234), as well as insignificant informational maintenance. The absence of gas chromatographic retention indices (RIs) on standard nonpolar polydimethylsiloxane stationary phases even for simplest chloro derivatives of mentioned cyclic ethers makes impossible the calculation of increments, which allow interpretation of data for more chlorinated products. As a result, the data for compounds of other series (including alicyclic ones, having different conformations) should be used as a rough approximation. Nevertheless, by this way, some simplest products of tetrahydrofuran and 1,4-dioxane chlorination were identified. Besides that, the joint interpretation of mass spectrometric and gas chromatographic data allowed us to identify three from four isomeric hexachloro-1,4-dioxanes.