Method of separating polycyclic aromatic hydrocarbons by...

Chemistry of hydrocarbon compounds – Purification – separation – or recovery – By contact with solid sorbent

Reexamination Certificate

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C585S830000, C585S831000

Reexamination Certificate

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06696615

ABSTRACT:

The invention relates to a method of separating polycyclic aromatic hydrocarbons by means of chromatographic methods.
Since some of the polycyclic aromatic hydrocarbons are carcinogenic and thus count as environmental poisons, they have to be analyzed in soil and water.
Previous methods determine the polycyclic aromatic hydrocarbons with the aid of nonpolar chromatography phases, for example RP-C18 phases. Standard methods are known for this purpose, as are prescribed, for example, in the drinking water regulations of the Federal Republic of Germany or in the analytical method EPA 610 of the Environmental Protection Agency of the United States of America.
Furthermore, Shaowen, Z et al.: Gas chromatography of calix[4]arene derivatives; published in: Fenxi Kexue Xuebao (1998), 14 (1), pp. 14-18, studied gas chromatographic phases comprising two different calix[4]arenes and their interaction with the polycyclic aromatic hydrocarbons and similar systems. The authors assume that the latter form host-guest compounds with the calix[4]arenes.
According to Sun, S., Gutsche, D. et al.: Capillary electrokinetic chromatography employing p-(Carboxyethyl)calix[n]arenes as running buffer additives; published in: Anal. Chem. (1997), 69 (3), pp. 344-348 and Kalchenko, O. I. et al.: Effect of Octakis(diethoxyphosphoryloxy)-tert-butylcalix[8]arene in mobile phase on the reversed-phase retention behavior of aromatic compounds: host-guest complex formation and stability constants determination; published in: Journal of Chromatographic Science, Vol. 36, May 1998, similar host-guest compounds are described when using calixarenes in capillary electrophoresis (CE) and in high performance liquid chromatography (HPLC) with, according to the method, the calixarenes being used as an Additive to the eluant.
The object of the invention is an effective separation of polycyclic aromatic hydrocarbons by means of chromatographic methods.
According to the invention, this object is achieved by using the calixarene-modified stationary separation phase for separating the polycyclic aromatic hydrocarbons by means of chromatography. For this purpose, the polycyclic aromatic hydrocarbons are dissolved in a suitable solvent, or solutions of polycyclic aromatic hydrocarbons in a liquid medium can be used.
The samples of the dissolved polycyclic aromatic hydrocarbons are passed with the aid of a suitable eluant in the form of a solvent and/or solvent mixture over the calixarene-modified stationary separation phase, with the polycyclic aromatic hydrocarbons being spatially separated from one another. The separated substances are then detected.


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Brindle, Roland et al., Journal ofChromatography A, 731 (1996) pp. 41-46 Siclica-bonded calixarenes in chromatography I. Synthesis and characterization by solid-state NMR spectroscopy.
Xu, W. et al.,Chromatographia, vol. 48, No. 3/4 (Aug. 1998) pp. 245-250 “Preparation and Characterization of p-tert-Butyl-Calix[6]arene-Bonded Silica Gel Stationary Phase for High Performance Liquid Chromatography”.
Chemical Abstracts, vol. 128, No. 16, Apr. 20, 1998, S. Zhang et al., “Gas chromatography of calix[4]arene derivatives”.
Chemical Abstracts, vol. 129, No. 23, Dec. 7, 1998, Z. Zheng et al., “Two kinds of calix [4] arene derivatives as capillary gas chromatography stationary phases”.
Sun, S. et al.,Anal. Chem., 69 (3) (1997) pp. 344-348 “Capillary electrokinetic chromatography employing p-(Carboxyethyl) calix[n] arenes as runnning buffer additives”.
Kalcheneko, O.I. et al,Journal of Chromatographic Science, vol. 36 (May 1998) “Effect of Octakis (diethoxyphosphoryloxy) -tert-butyl-calix[8] arene in mobile phase on the reversed-phase retention behavior of aromatic compounds: Host-guest complex formation and Stability Constants Determination”.

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