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Adsorption of Dimethylanilines on Montmorillonite in High-Pressure Liquid Chromatography

Published online by Cambridge University Press:  02 April 2024

U. Mingelgrin  and
F. Tsvetkov
U. Mingelgrin
Affiliation:
Institute of Soils and Water, Agricultural Research Organization, The Volcani Center, Bet Dagan 50-250, Israel1
F. Tsvetkov
Affiliation:
Institute of Soils and Water, Agricultural Research Organization, The Volcani Center, Bet Dagan 50-250, Israel1
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Abstract

High-pressure liquid chromatography columns were packed with quasi-spherical particles of bentonite (SP-bentonite) which were prepared from a predominantly Na-bentonite powder by spray drying. The strength of adsorption of ring-substituted dimethylanilines on bentonite was directly related to their basicity (pKa). The adsorption of the amino-substituted N, N-dimethylaniline was commonly much weaker than that predicted from its pKa, suggesting that the amino group was the dominant site of interaction between the substituted anilines and the clay.

A better separation between the dimethylaniline isomers was obtained on SP-bentonite than on a neutral silica under the same chromatographic conditions. A selectivity factor of 25 was achieved between the most strongly and the least strongly adsorbed ring substituted isomers (3, 5- and 2,6-dimethylaniline, respectively) on the SP-bentonite. The selectivity factor was 3.4 on the silica. This efficiency of separation demonstrated the potential advantage of the readily available bentonite in high-pressure liquid chromatography. The higher resolution achieved in column runs than in batch experiments may be utilized for the elucidation of mechanisms of interaction of organic molecules at clay surfaces by comparing the interaction of a number of closely related adsorbates.

Keywords

AdsorptionBentoniteDimethylanilineLiquid chromatographySilica
Type
Research Article
Information
Clays and Clay Minerals , Volume 33 , Issue 4 , August 1985 , pp. 285 - 294
Copyright
Copyright © 1985, The Clay Minerals Society

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References

Banin, A. and Lahav, N., 1968 Particle size and optical properties of montmorillonite in suspension IsraelJ. Chem. 6 235–250.CrossRefGoogle Scholar
Berezkin, V. G. and Gavrichev, V. S., 1976 Retention of hydrocarbons on gas chromatographic sorbente containing an organo-clay J. Chromatogr. 116 9–16.CrossRefGoogle Scholar
Bickov, V. T., Gerasimov, V. G., Kridganska, G. A. and Shevtsov, V. P., 1976 The chromatographic study of adsorption of some polar and nonpolar compounds in ka-olinite and montmorillonite Kolloidn. Zh. 38 542–543 (in Russian).Google Scholar
Borchardt, G. A., Dixon, J. B. and Weed, S. B., 1977 Montmorillonite and other smectite minerals Minerals in Soil Environments Madison, Wisconsin Soil Science Society of America 293–330.Google Scholar
Cowan, C. T. and Hartwell, J. M., 1961 An organoclay complex for the separation of isomeric dichlorobenzenes using gas chromatography Nature 190 712.CrossRefGoogle Scholar
Dimant, E., Sanadi, D. R. and Huennekens, F. M., 1952 The isolation of flavin nucleotides J. Amer. Chem. Soc. 74 5440–5444.CrossRefGoogle Scholar
Engelhardt, H. and Muller, H., 1981 Chromatographic characterization of silica surfaces J. Chromatogr. 218 395–407.CrossRefGoogle Scholar
Georges, L. W., Bower, R. S. and Wolfram, M. L., 1946 Chromatography of sugars and their derivatives J. Amer. Chem. Soc. 68 2169–2171.CrossRefGoogle ScholarPubMed
Grant, D. W., Meiris, R. B. and Hollis, M. G., 1974 The use of Bentone-34-coated supports in column chromatography and their potential application in the field of organic pollution analysis J. Chromatogr. 99 721–729.CrossRefGoogle ScholarPubMed
Heller, L., Yariv, S. and Heller, L., 1969 Sorption of some anilines by Mn-, Co-, Ni-, Cu-, Zn- and Cd-montmorillonite Proc. Int. Clay Conf., Tokyo, 1969 Jerusalem Israel Universities Press 741–755.Google Scholar
Jewett, D. and Lawless, J. G., 1980 A simple apparatus for the upward slurry packing of HPLC columns J. High Resolution Chromatog. Chromatogr. Comm. 3 647–648.CrossRefGoogle Scholar
Kiselev, A. V., Lebedeva, N. P., Frolov, I. I. and Jashin, J. I., 1972 Liquid-solid chromatography on Bentone-34 Chromatographia 5 341–345.CrossRefGoogle Scholar
Lafosse, M., Keravis, G., Coic, J. P. and Saint-Ruf, G., 1978 High performance liquid and gas-liquid chromatography of isomeric phenoxanthiins. Use of organo-clay to increase selectivity Chromatographia 11 141–144.CrossRefGoogle Scholar
Larsen, P. and Schou, O., 1981 Simple apparatus for size fractionation of particles by hydrodynamic elutriation J. High Resolution Chromatog. Chromatogr. Comm. 4 244–245.CrossRefGoogle Scholar
Lew, B. W., Wolfrom, M. L., Goepp, R. M. Jr., 1946 Chromatography of sugars and related polyhydroxy compounds J. Amer. Chem. Soc. 68 1449–1453.CrossRefGoogle ScholarPubMed
McAtee, J. L. Jr. and Robbins, R. C., 1980 Gas chromatographic separation of cresols by various quaternary ammonium substituted montmorillonites Clays & Clay Minerals 28 61–64.CrossRefGoogle Scholar
Mingelgrin, U. and Saltzman, S., 1979 Surface reactions of parathion clays Clays & Clay Minerals 27 72–78.CrossRefGoogle Scholar
Mortland, M. M., 1970 Clay-organic complexes and interactions Adv. Agron. 22 75–117.CrossRefGoogle Scholar
Ratner-Zohar, Y., Banin, A. and Chen, Y., 1983 Oven-drying as a pretreatment for surface-area determinations of soils and clays Soil Sci. Soc. Amer. J. 47 1056–1058.CrossRefGoogle Scholar
Richards, L. A., ed. (1954) Diagnosis and improvement of saline and alkaline soils: in Handbook of the U.S. Department of Agriculture, 60, 19–20.Google Scholar
Schmeltz, J., Dyer, C. T., Ratchik, E. and Matasker, J., 1982 Separation and determination of xylidine isomers: comparison of gas and liquid chromatographic methods J. Chromatogr. 245 309–320.CrossRefGoogle Scholar
Schram, S.B., 1980 The LDC Basic Book on Liquid Chromatography Florida Milton Roy Co., St. Petersburg 21–25.Google Scholar
Shirobokov, V. P., Zaikjova, J. P. and Zagoruiko, E. E., 1975 Chromatographic separation of ribonucleic acid and bacterial and animal cells on MAB (methylated albinum adsorbed on bentonite) columns Biokhimiya 40 531–537.Google Scholar
Shomer, I. and Mingelgrin, U., 1978 A direct procedure for determining the number of plates in tactoids of smectites: the Na/Ca-montmorillonite case Clays & Clay Minerals 26 135–138.CrossRefGoogle Scholar
Smith, J. W. and Patai, S., 1968 Basicity and complex formation The Chemistry of the Amino Group London Interscience Publ. 161–204.Google Scholar
Taramasso, M., 1971 Adsorbents for gas-solid chromatography prepared by epitaxial modification of clay minerals with quaternary ammonium ions J. Chromatogr. 58 31–38.CrossRefGoogle Scholar
Thelmann, V. J., McAtee, J. L. Jr., 1975 Gas chromatographic behavior of metal-tris(ethylenedianiline) complex cation-exchanged montmorillonites J. Chromatogr. 105 115–123.CrossRefGoogle Scholar
Thelmann, V. J., McAtee, J. L. Jr., 1978 Comparison of gas chromatographic properties of tris(ethylene-diamine)chromium cation exchanged on montmorillo-nite, hectorite and attapulgite J. Chromatogr. 147 408–411.CrossRefGoogle Scholar
Theng, B. K. C., 1974 The Chemistry of Clay-Organic Reactions London Adam Hilger 102.Google Scholar
Unger, K. K., 1979 Porous Silica Amsterdam-Oxford-New York Elsevier Scientific Publ. 133.Google Scholar
van Olphen, H., 1977 Clay Colloid Chemistry New York Wiley-Interscience Publ. 72.Google Scholar
White, D., 1957 Use of organic-montmorillonite compounds in gas chromatography Nature 179 1075–1076.CrossRefGoogle Scholar
Yamagishi, A., 1982 Clay column chromatography: partial resolution of metal(III) tris(acetylaceotonato) on a Δ-nickel(II)tris(l,10-phenanthroline) montmorillonite column Inorg. Chem. 21 3393–3396.CrossRefGoogle Scholar
Yamagishi, A. and Ohnishi, R., 1982 Clay column chromatography for optical resolution: partial resolution of tris(acetylacetonato) metal(III) on a Δ-tris(l,10-phenan-throline)ruthenium(II) montmorillonite column J. Chromatogr. 245 213–218.CrossRefGoogle Scholar
Yamagishi, A. and Ohnishi, R., 1983 Chromatographic resolution of cyclic organic compounds on a Δ-tris(l,10-phenanthroline)ruthenium(II) montmorillonite column Angew. Chem. Int. Ed. Eng. 22 162–163.CrossRefGoogle Scholar
Yamagishi, A., Ohnishi, R. and Soma, M., 1982 Chromatographic resolution of tris(acetylacetonato) cobalt(III) on a Δ-tris( 1,10-phenanthroline) nickel(II) montmorillonite column Chem. Lett. 85–88.CrossRefGoogle Scholar
Yamagishi, A. and Soma, M., 1981 Optical resolution of metal chelates by use of adsorption on a colloidal clay J. Amer. Chem. Soc. 103 4640–4642.CrossRefGoogle Scholar
Yariv, S., Heller, L. and Kaufherr, N., 1969 Effect of acidity in montmorillonite interlayers on the sorption of aniline derivatives Clays & Clay Minerals 17 301–306.CrossRefGoogle Scholar