Skip to main content
SpringerLink
Log in

Interpretation of interactions of halogenated hydrocarbons with modified silica adsorbent coated with 3-benzylketoimine group silane

  • Original Paper
  • Published:
Chemical Papers Aims and scope Submit manuscript

Abstract

The paper reports a new group of adsorbents obtained by modification of silica surface with silane containing 3-benzylketoimine groups with bonded Cu(II) and Ni(II) chlorides. The adsorbents obtained were subjected to a chromatographic study to establish the type of adsorbate-adsorbent interactions for aliphatic and aromatic halogenated hydrocarbons used as adsorbates. The following retention parameters were determined: retention factor (k), Kovats retention index (I), specific retention volume (V g), and molecular retention index (ΔM e). Values of the molecular retention index were subjected to complex statistical analysis providing qualitative relations between the adsorbates’ properties and spatial structure and their retention. It was observed that bonding of chlorides of Cu(II) and Ni(II) with the ketoimine groups resulted in an increase of the retention index and the molecular retention index indicating an increase of the adsorbate-adsorbent interaction in comparison with the reference column coated with silane including a 3-benzylketoimine group without transition metal chlorides. Along with the observed increase of the adsorbate-adsorbent interaction, larger difference between the retention indices was observed for both halogenated compounds. This indicates a positive influence of the introduced transition metals on the selectivity of the adsorbate-adsorbent interactions of the examined columns.

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

  • Andersson, P., Haglund, P., Rappe, C., & Tysklind, M. (1996). Ultraviolet absorption characteristics and calculated semi-empirical parameters as chemical descriptors in multivariate modelling of polychlorinated biphenyls. Journal of Chemometrics, 10, 171–185. DOI: 10.1002/(SICI)1099-128X(199603)10:2<171::AID-CEM416>3.0.CO;2-U.

    Article  CAS  Google Scholar 

  • Bielecki, P., & Wasiak, W. (2011). Predicting retention indices of aliphatic hydrocarbons on stationary phases modified with metallocyclams using quantitative structure-retention relationships. Chemical Papers, 65, 104–112. DOI: 10.2478/s11696-010-0085-8.

    Article  CAS  Google Scholar 

  • Deng, H., Huang, P., Hu, Y., Ye, N., & Li, Z. (2005). A novel molecular distance edge vector as applied to chemical modeling of quantitative structure-retention relationships: Various gas chromatographic retention behaviors of polychlorinated dibenzofurans on different polarity-varying stationary phases. Chinese Science Bulletin, 50, 1683–1687. DOI: 10.1360/982004-252.

    Article  CAS  Google Scholar 

  • Evans, M. B. (1978). Gas chromatography in qualitative analysis. Part 14. Molecular retention index as an alternative system for the characterization of gas chromatographic stationary phases. Chromatographia, 11, 183–187. DOI: 10.1007/BF02302389.

    Article  CAS  Google Scholar 

  • Harju, M., Andersson, P. L., Haglund, P., & Tysklind, M. (2002). Multivariate physicochemical characterization and quantitative structure-property relationship modeling of polybrominated diphenyl ethers. Chemosphere, 47, 375–384. DOI: 10.1016/S0045-6535(01)00339-3.

    Article  CAS  Google Scholar 

  • Ivanciuc, T., & Ivanciuc, O. (2002). Quantitative structure-retention relationship study of gas chromatographic retention indices for halogenated compounds. Internet Electronic Journal of Molecular Design, 1, 94–107.

    CAS  Google Scholar 

  • Jalali-Heravi, M., Noroozian, E., & Mousavi, M. (2004). Prediction of relative response factors of electron-capture detection for some polychlorinated biphenyls using chemometrics. Journal of Chromatography A, 1023, 247–254. DOI: 10.1016/j.chroma.2003.10.012.

    Article  CAS  Google Scholar 

  • Jönsson, J. A. (1987). Chromatographic theory and basic principles. New York, NY, USA: Marcel Dekker.

    Google Scholar 

  • Kaliszan, R. (1987). Quantitative structure-chromatographic retention relationship. New York, NY, USA: Wiley.

    Google Scholar 

  • Kato, H., Ueda, Y., & Nakata, M. (2000). Calibration method for the gas-chromatographic retention time of polychlorinated biphenyl congeners. Analytical Sciences, 16, 693–699. DOI: 10.2116/analsci.16.693.

    Article  CAS  Google Scholar 

  • Korytár, P., Covaci, A., de Boer, J., Gelbin, A., & Brinkman, U. A. Th. (2005). Retention-time database of 126 poly-brominated diphenyl ether congeners and two Bromkal technical mixtures on seven capillary gas chromatographic columns. Journal of Chromatography A, 1065, 239–249. DOI: 10.1016/j.chroma.2004.12.059.

    Article  Google Scholar 

  • Krawczuk, A., Voelkel, A., Lulek, J., Urbaniak, R., & Szyrwińska, K. (2003). Use of topological indices of polychlorinated biphenyls in structure-retention relationships. Journal of Chromatography A, 1018, 63–71. DOI: 10.1016/j.chroma.2003.08.037.

    Article  CAS  Google Scholar 

  • Liang, X., Wang, W., Schramm, K.-W., Zhang, Q., Oxynos, K., Henkelmann, B., & Kettrup, A. (2000). A new method of predicting of gas chromatographic retention indices for polychlorinated dibenzofurans (PCDFs). Chemosphere, 41, 1889–1895. DOI: 10.1016/S0045-6535(00)00052-7.

    Article  Google Scholar 

  • Liu, S. S., Yin, C. S., & Wang, L. S. (2002). MEDV-13 for QSRR of 62 polychlorinated naphthalenes. Chinese Chemical Letters, 13, 791–794.

    CAS  Google Scholar 

  • Moustafa, N. E. (2009). Gas chromatographic retention times prediction for components of petroleum condensate fraction. Chemical Papers, 63, 608–612. DOI: 10.2478/s11696-009-0045-3.

    Article  CAS  Google Scholar 

  • Olivero, J., & Kannan, K. (1999). Quantitative structure-retention relationships of polychlorinated naphthalenes in gas chromatography. Journal of Chromatography A, 849, 621–627. DOI: 10.1016/S0021-9673(99)00402-1.

    Article  CAS  Google Scholar 

  • Rybolt, T. R., Logan, D. L., Milbrun, M. W., Thomas, H. E., & Waters, A. B. (1999). Correlations of Henry’s law gas-solid virial coefficients and chromatographic retention times for hydrocarbons and halocarbons adsorbed on carbopack C carbon. Journal of Colloid and Interface Science, 220, 148–156. DOI: 10.1006/jcis.1999.6522.

    Article  CAS  Google Scholar 

  • Santiuste, J. M., Harangi, J., & Takács, J. M. (2003). Mosaic increments for predicting the gas chromatographic retention data of the chlorobenzenes. Journal of Chromatography A, 1002, 155–168. DOI: 10.1016/S0021-9673(03)00736-2.

    Article  CAS  Google Scholar 

  • Santiuste, J. M., & Takács, J. M. (2003). Relationships between retention data of benzene and chlorobenzenes with their physico-chemical properties and topological indices. Chromatographia, 58, 87–96. DOI: 10.1365/s10337-003-0013-y.

    CAS  Google Scholar 

  • Sielex, K., & Andersson, J. T. (2000). Prediction of gas chromatographic retention indices of polychlorinated dibenzothiophenes on non-polar columns. Journal of Chromatography A, 866, 105–120. DOI: 10.1016/S0021-9673(99)01079-1.

    Article  CAS  Google Scholar 

  • van Deemter, J. J., Zuiderweg, F. J., & Klinkenberg, A. (1956). Longitudinal diffusion and resistance to mass transfer as causes of non ideality in chromatography. Chemi cal Engineering Science, 5, 271–289. DOI: 10.1016/0009-2509(56)80003-1.

    Google Scholar 

  • Wang, D., Xu, X., Chu, S., & Zhang, D. (2003). Analysis and structure prediction of chlorinated polycyclic aromatic hydrocarbons released from combustion of polyvinylchloride. Chemosphere, 53, 495–503. DOI: 10.1016/S0045-6535(03) 00507-1.

    Article  CAS  Google Scholar 

  • Wang, H., Wang, X., Zhao, J., Sun, C., & Wang, L. (2005). Holographic QSRR of polychlorinated dibenzofurans. Chinese Science Bulletin, 50, 961–964. DOI: 10.1360/04wb0094.

    Article  CAS  Google Scholar 

  • Wang, Y., Li, A., Liu, H., Zhang, Q., Ma, W., Song, W., & Jiang, G. (2006). Development of quantitative structure gas chromatographic relative retention time models on seven stationary phases for 209 polybrominated diphenyl ether congeners. Journal of Chromatography A, 1103, 314–328. DOI: 10.1016/j.chroma.2005.11.034.

    Article  CAS  Google Scholar 

  • Wawrzyniak, R. (2009). Quantitative relationship and application of 3-benzylketoimine metal dichlorides in the analysis of volatile hydrocarbons. Journal of Separation Science, 32, 1415–1424. DOI: 10.1002/jssc.200800616.

    Article  CAS  Google Scholar 

  • Wawrzyniak, R., & Wasiak, W. (2005). Ketoimine modified silica as an adsorbent for gas chromatographic analysis of olefins. Journal of Separation Science, 28, 2454–2462. DOI: 10.1002/jssc.200400035.

    Article  CAS  Google Scholar 

  • Wawrzyniak, R., & Wasiak, W. (2004). Silica modified with ketoimine group-containing silane as an adsorbent in capillary columns. Chromatographia, 59, 205–211. DOI: 10.1365/s10337-003-157-9.

    CAS  Google Scholar 

  • Wawrzyniak, R., & Wasiak, W. (2003). New method for bonding an adsorbent film to the walls of capillary columns. Journal of Separation Science, 26, 1219–1224. DOI: 10.1002/jssc.200301430.

    Article  CAS  Google Scholar 

  • Zenkevich, I. G. (2001). Interpretation of retention indices in gas chromatography for establishing structures of isomeric products of alkylarenes radical chlorination. Russian Journal of Organic Chemistry, 37, 270–280. DOI: 10.1023/A:1012343416008.

    Article  CAS  Google Scholar 

  • Zhai, Z.-C., Wang, Z.-Y., & Chen, S.-D. (2006). Quantitative structure-retention relationship for gas chromatography of polychlorinated naphthalenes by ab initio quantummechanical calculations and a Cl substitution position method. QSAR & Combinatorial Science, 25, 7–14. DOI: 10.1002/qsar.200530111.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780, Poznań, Poland

    Rafał Wawrzyniak & Wiesław Wasiak

Authors
  1. Rafał Wawrzyniak
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Wiesław Wasiak
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Rafał Wawrzyniak.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wawrzyniak, R., Wasiak, W. Interpretation of interactions of halogenated hydrocarbons with modified silica adsorbent coated with 3-benzylketoimine group silane. Chem. Pap. 65, 626–635 (2011). https://doi.org/10.2478/s11696-011-0060-z

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.2478/s11696-011-0060-z

Keywords

Search

Navigation