Hostname: page-component-cd9895bd7-lnqnp Total loading time: 0 Render date: 2024-12-28T16:49:58.253Z Has data issue: false hasContentIssue false
  • English
  • Français

Cross-Linked Hydroxy-Al-Montmorillonite as a Stationary Phase in Liquid Chromatography

Published online by Cambridge University Press:  02 April 2024

Faina Tsvetkov ,
U. Mingelgrin  and
N. Lahav
Faina Tsvetkov
Affiliation:
Institute of Soils and Water, Agricultural Research Organization, The Volcani Center, P.O. Box 6, Bet Dagan 50-250, Israel
U. Mingelgrin
Affiliation:
Institute of Soils and Water, Agricultural Research Organization, The Volcani Center, P.O. Box 6, Bet Dagan 50-250, Israel
N. Lahav
Affiliation:
The Seagram Center for Soil and Water Sciences, The Faculty of Agriculture, The Hebrew University of Jerusalem, P.O. Box 12, Rehovot 76-100, Israel
Rights & Permissions [Opens in a new window]

Abstract

Core share and HTML view are not available for this content. However, as you have access to this content, a full PDF is available via the ‘Save PDF’ action button.

Quasi-spherical particles (7-µm mean diameter) were prepared from cross-linked hydroxy-Al-montmorillonite (basal spacing =15.3 and 18.6 Å) by spray-drying. These particles (SP-CLM) were used as a packing material for columns in high-pressure liquid chromatography (HPLC). Aromatic phosphate esters, chlorosubstituted phenyl-ureas, monosubstituted benzenes, and the o-, m-, and p-isomers of disubstituted benzenes were separated on the columns, using isopropanol and hexane. Alkyl and alkoxy groups in the solute molecules sterically hindered the interaction of these molecules with the solid phase. The retention of the isomers of disubstituted benzenes that possess one electronegative (or dipolar) and one nonpolar substituent increased in the order: o- < m- < p-. In contrast, for all investigated disubstituted benzenes containing two electronegative (or dipolar) substituents, the o-isomer was retained on the 18.6-Å SP-CLM more strongly than the m- and p-isomers. The chromatographic data suggest that the strength of the interaction of phenolic groups with the solid phase increased with the acidity of these groups. The o-isomers of phenols that contained an additional electronegative (or dipolar) substituent displayed an exceptionally strong adsorption. The capacity of the o-isomers of disubstituted benzenes containing two electronegative (or dipolar) substituents to form chelates with Al probably was responsible for the strong retention of such o-isomers compared with the retention of the corresponding m- and p-isomers.

Cross-linked hydroxy-Al-montmorillonite acted as a strong and selective adsorbent for many families of organic compounds. It was used successfully as the solid phase in HPLC separations with eluents ranging from nonpolar (e.g., hexane) to highly polar (e.g., water).

Keywords

AdsorptionChelationCross-linked smectiteDisubstituted benzeneHigh-pressure liquid chromatographyHydroxy-AlMonosubstituted benzenePhenyl-ureaPhosphate esters
Type
Research Article
Information
Clays and Clay Minerals , Volume 38 , Issue 4 , August 1990 , pp. 380 - 390
Copyright
Copyright © 1990, The Clay Minerals Society

References

Boit, H. G., 1964 Beilstein Handbuch der Organischen Chemie: Vol. 5, Supplement 3, Part 2 619 705 – 708.Google Scholar
Bottero, J. Y., Cases, J. M., Fiessinger, F. and Poirier, H., 1980 Studies of hydrolyzed aluminum chloride solutions. 1. Nature of aluminum species and composition of aqueous solutions J. Phys. Chem. 84 2933 – 2939.CrossRefGoogle Scholar
Bowman, B. T. and Sans, W. W., 1977 Adsorption of parathion, fenitrothion, methyl parathion, amino-parathion and paraoxon on Na+, Ca2+, and Fe3+ montmorillonite suspensions Soil Sci. Soc. Amer. J. 41 514 – 519.CrossRefGoogle Scholar
Cotton, F. A. and Wilkinson, G. W., 1966 Advanced Inorganic Chemistry 2nd ed. New York Interscience.Google Scholar
Hirschfelder, J. O., Curtis, C. F. and Bird, R. B., 1954 Molecular Theory of Gases and Liquids New York Wiley 941 – 950.Google Scholar
Ketelaar, J. A. A. Gersmann, H. R. and Hartog, F., 1958 Chemical studies of insecticides. VII. Dipole moments of some esters of phosphoric and phosphorothionic acid Recueil des Travaux Chimiques des Pays-Bas 77 982 – 989.CrossRefGoogle Scholar
Kiselev, A. V., Aratskova, A. A., Gvozdovitch, T. N. and Yashin, Ya I, 1980 Retention behavior of o-, m- and p-isomers of benzene derivatives on a silica gel hydrox-ylated surface in liquid chromatography J. Chromatogr. 195 205 – 210.CrossRefGoogle Scholar
Lahav, N. and Shani, U., 1978 Cross-linked smectites. II. Flocculation and microfabric characteristics of hydroxy-aluminum-montmorillonite Clays & Clay Minerals 26 116 – 124.CrossRefGoogle Scholar
Lahav, N., Shani, U. and Shabtai, J., 1978 Cross-linked smectites. I. Synthesis and properties of hydroxyaluminum-montmorillonite Clays & Clay Minerals 26 107 – 115.CrossRefGoogle Scholar
Mingelgrin, U. and Saltzman, S., 1979 Surface reactions of parathion on clays Clays & Clay Minerals 27 72 – 78.CrossRefGoogle Scholar
Mingelgrin, U. and Tsvetkov, F., 1985 Adsorption of dimethylanilines on montmorillonite in high-pressure liquid chromatography Clays & Clay Minerals 33 285 – 294.CrossRefGoogle Scholar
Mortland, M. M., 1970 Clay-organic complexes and interactions Adv. Agron. 22 75 – 117.CrossRefGoogle Scholar
Pinnavaia, T. J., 1983 Intercalated clay catalysts Science 220 365 – 371.CrossRefGoogle ScholarPubMed
Richter, F., 1943 Beilstein Handbuch der Organischen Chemie: Vol. 5, Supplement 2 4th ed. Berlin Springer-Verlag.Google Scholar
Rochester, C. H. and Patai, S., 1971 Acidity and inter- and intra-molecular H-bonds The Chemistry of Hydroxyl Groups London Interscience 327 – 392.CrossRefGoogle Scholar
Sahay, B. K. and Low, M. J. D., 1974 Interactions between surface hydroxyl groups and adsorbed molecules V. Fluorobenzene on germania J. Coll. Interface Sci. 48 20 – 31.CrossRefGoogle Scholar
Shabtai, J., Rosell, M. and Tokarz, M., 1984 Cross-linked smectites. III. Synthesis and properties of hydroxy-aluminum hectorites and fluor hectorites Clay & Clay Minerals 32 99 – 107.CrossRefGoogle Scholar
Theng, B. K. G., 1974 The Chemistry of Clay-Organic Reactions London Adam Hilger.Google Scholar
Tsvetkov, F., 1985 Surface interactions of small organic molecules with clays involving exchangeable cations Jerusalem, Israel Hebrew University of Jerusalem.Google Scholar
Tsvetkov, F. and Mingelgrin, U., 1987 Optically selective adsorption of α-amino acids on montmorillonite-Cu-1-lysine complexes in high pressure liquid chromatography Clays & Clay Minerals 35 391 – 399.CrossRefGoogle Scholar
Unger, K. K., 1979 Porous Silica Amsterdam Elsevier 133.Google Scholar
Van Bladel, R. and Moreale, A., 1974 Adsorption of fenuron and monuron by two montmorillonite clays Soil Sci. Soc. Amer. Proc. 38 244 – 249.CrossRefGoogle Scholar
Weast, R. C., 1973 Handbook of Chemistry and Physics 54th ed. Boca Raton, Florida CRC Press E – 64.Google Scholar
Worthing, C. R., 1983 The Pesticide Manual 7th ed. Croydon, United Kingdom British Crop Protection Council.Google Scholar