Retention behaviour of o-, m- and p-isomers of benzene derivatives on a silica gel hydroxylated surface in liquid chromatography

Киселев, А. В.; Aratskova, A. A.; Gvozdovitch, T.N.; Yashin, Ya. I.

doi:10.1016/s0021-9673(00)96811-0

Cited by 31 publications

(17 citation statements)

References 7 publications

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“…Kiselev et al (1980) reported that o-bromonitrobenzene adsorbed on the hydroxylated silica gel from nonpolar solvents more strongly than the p-isomer. On the other hand, the order of retention on the hydroxylated silica gel of the isomers of phenols which were classified in the present study as belonging to group II was in all cases: o-< m-< p-.…”

Section: Retention Of Disubstituted Benzenesmentioning

confidence: 99%

“…This bidentate interaction may explain the above mentioned observation that the o-isomer of bromonitrobenzene adsorbed on the hydroxylated silica gel more strongly than the p-isomer. Kiselev et aL (1980) suggested, however, that an intramolecular H-bond probably exists between the phenolic hydroxyl and the second substituent in the orthoisomers of the group-II phenols. This bond had to be broken to enable the simultaneous interaction between both substituents and a surface proton.…”

Section: Retention Of Disubstituted Benzenesmentioning

confidence: 99%

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

Tsvetkov

1990

Clays and clay miner.

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Abstract--Quasi-spherical particles (7-tzm mean diameter) were prepared from cross-linked hydroxy-A1-montmorillonite (basal spacing = 15.3 and 18.6 A) 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-A 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 A1 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).

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Section: Retention Of Disubstituted Benzenesmentioning

confidence: 99%

Section: Retention Of Disubstituted Benzenesmentioning

confidence: 99%

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

Tsvetkov

1990

Clays and clay miner.

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“…2 Kiselev et aL (1980) and Weast (1973). 3 AI-CLM: cross-linked hydroxy-Al-montmorillonite, basal spacing 18.6 Zk (Tsvetkov et al, 1990).…”

Section: Solvent Effectmentioning

confidence: 99%

“…Steric hindrance will decrease with increased swelling, i.e., with increased polarity of the eluent. The presence of an intramolecular H-bond between the phenolic H and an electronegative NO2 group in the o-position (Kiselev et aL, 1980) also hinders bidentate interaction. The higher the valence of the countercation and the more polar the eluent, the greater the probability of breakage of that H-bond as well as of the dissociation of the phenolic hydroxyl.…”

Section: Retention Of O- M- and P-isomers Of Disubstituted Benzenesmentioning

confidence: 99%

Potassium Halide-Treated Montmorillonite (KTM) as a Solid Phase in Liquid Chromatography

Tsvetkov

Heller-Kallai

Mingelgrin

1993

Clays and clay miner.

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Abstract--Columns for high pressure liquid chromatography were prepared from spray dried samples of montmorillonite that were heated with potassium halides (KTM) to increase both the cation density on the clay surfaces and the expandability of the interlayers. Some of the clay samples were exchanged with Cu before and/or after the potassium halide treatment.Retention of nitrobenzene and its chloro and methyl derivatives, of methyl substituted phenols and of nitrophenols on these columns was studied, using eluents ranging in polarity from hexane to isopropanol. The retention of the aromatic molecules depends on their specific interaction with active sites on the clay surfaces and on steric effects which limit access to the clay interlayers. Both penetrability and surface interaction are controlled by the composition and method of preparation of the solid phase and by the polarity of the mobile phase. Very strong adsorption of some eluates and efficient chromatographic separations between related substituted benzenes were achieved. Mixtures of the three isomers of cresol, chloronitrobenzene, nitrotoluene or nitrophenol were completely resolved by a judicious combination of solid phase and eluent.

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“…The latest method has been most used as alternatives in industrial process for the separation [4]. Adsorptive separations have been investigated in using various adsorbents such as with zeolites [5], silica gel [6] and carbon materials such as activated charcoal [7].…”

Section: Introductionmentioning

confidence: 99%

Removal of O,m,p-Xylene From Air Samples on Oxidized Carbon Nanotubes Cartridges

Anh¹

2018

JST

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Carbon nanotubes (CNTs) have been considered as an excellent adsorbent in environmental engineering, especially for treatment of volatile organic compounds (VOCs). The paper presents a new approach for the selective adsorption of Xylene isomers from air samples using nanomaterial based on oxidized multiwalled carbon nanotubes. In the first study, the functionalization of two oxidized MWCNTs was achieved with hydrogen peroxide and sodium hypochlorite. The characterization of functionalized CNTs (CNT-NaOCl, CNT-H2O2) was performed by Fourier transform infrared spectroscopy (FT-IR) and X-Ray diffractometer (XRD). Afterthat, the applications of pristine CNTs and oxidized CNTs for removal of three Xylene isomers from air samples were discussed. The results demonstrate that the correlation of CNTs and three isomers was significantly different with an affinity order o-Xylene > m-Xylene > p-Xylene. The oxidized CNTs with carbonyl groups increased significantly its adsorption capacity for these isomers. A comparison in term of adsorption performance shows that the framework distinguishes among these adsorbents due to the dispersive properties and the electrostatic interaction between the Xylene isomers and oxidized CNTs surface.

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Retention behaviour of o-, m- and p-isomers of benzene derivatives on a silica gel hydroxylated surface in liquid chromatography

Cited by 31 publications

References 7 publications

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

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

Potassium Halide-Treated Montmorillonite (KTM) as a Solid Phase in Liquid Chromatography

Removal of O,m,p-Xylene From Air Samples on Oxidized Carbon Nanotubes Cartridges

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