Liquid purification or separation – Processes – Liquid/liquid solvent or colloidal extraction or diffusing...
Patent
1984-01-18
1986-08-05
Schofer, Joseph L.
Liquid purification or separation
Processes
Liquid/liquid solvent or colloidal extraction or diffusing...
210656, 252184, 521 38, B01D 1508
Patent
active
046042075
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a novel packing material for chromatographic use comprising an inorganic carrier having grafted thereon an optically active organosilane and a method for analysis of enantiomer mixtures of compounds containing an --NH-- group, a --CONH-- group, or an --OCO-- group bonded to an asymmetric carbon atom thereof which comprises separating the enantiomer mixtures using the packing material by means of liquid chromatography.
BACKGROUND TECHNOLOGY
As methods for directly separating and analyzing enantiomer mixtures of compounds containing an asymmetric carbon atom using optically active compound-grafted packing materials by means of liquid chromatography, there have hitherto been only a few of reports, for example, a ligand exchange-method by Davankov et al. in which optically active proline-grafted packing materials are used; a charge transfer complex-method by Gil-Av et al. in which .pi.-electron-lacking and optically active compound-grafted packing materials are used; a method involving separation of N-acylated amino acid esters or N-acylated dipeptide esters using optically active N-acylated amino acid-grafted packing materials by Hara et al.; a method involving separation of 3,5-dinitrobenzoylated amino acids, amines, hydroxy acids, sulfoxides, etc. using optically active 1-(9-anthryl)trifluoroethanol-grafted packing materials, or a method involving separation of aromatic alcohols using 3,5-dinitrobenzoylated and optically active phenylglycine-grafted packing materials by Pirkle et al.; and so on. In these methods, however, compounds useful for analysis are limited to a narrow range, a degree of separation is poor, or grafted packing materials are produced with difficulty so that packing materials have good reproducibility in the quality, etc. It cannot thus be said that these packing materials are practical.
DISCLOSURE OF THE INVENTION
As a result of extensive investigations with an attempt to develop grafted packing materials which are widely applicable to compounds to be analyzed, are relatively easily prepared, are chemically stable and are practical, the present inventors have found that packing materials for chromatographic use obtained by grafting .alpha.-arylalkylamine derivatives which are formed by bonding optically active .alpha.-arylalkylamines and aminoalkylsilanes through dibasic carboxylic acids, on inorganic carriers having hydroxyl groups at the surface thereof are extremely useful since they not only exhibit an excellent effect for separating enantiomer mixtures of compounds containing an --NH-- group, a --CONH-- group, or an --OCO-- group bonded to an asymmetric carbon atom thereof, but also can easily be prepared by ordinary chemical reactions and are chemically stable, and have reached the present invention.
Namely, the present invention is to provide a packing material for chromatographic use comprising an inorganic carrier having hydroxyl groups at the surface thereof having grafted thereon an .alpha.-arylalkylamine derivative which is formed by bonding an optically active .alpha.-arylalkylamine and an aminoalkylsilane through a dibasic carboxylic acid and a method for separating and analyzing an enantiomer mixture of a compound containing an --NH-- group, a --CONH-- group, or an --OCO-- group bonded to an asymmetric carbon atom thereof by using the above described packing material as a stationary phase for liquid chromatography.
In the present invention, the grafted .alpha.-arylalkylamine derivatives are organosilanes represented by general formula (I): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 each, which may be the same or different, is an alkyl group, an alkoxyl group, a hydroxyl group or a halogen atom, with proviso that at least one thereof is an alkoxyl group or a halogen atom; R.sub.4 is an alkyl group; Ar is a phenyl group or a naphthyl group, which may be substituted; X is --NHCO-- or --N.sup..sym. H.sub.3 O.sup..crclbar. CO; Y is a lower alkylene group or a phenylene group; n is an integer of from 2 to 4; and * indic
REFERENCES:
patent: 4322310 (1982-03-01), House
patent: 4324681 (1982-04-01), House
Haro et al-Journal of Chromat. 186, (1979), pp. 543-552.
S. Weinstein et al-Journal of Chromatography, 126 (1976), 97-111.
W. Pirple et al-Journal of Chromatography 123, (1976), 400-404.
Doi Tadashi
Nagase Masayuki
Oi Naobumi
Kulkosky Peter F.
Schofer Joseph L.
Sumitomo Chemical Co,. Ltd.
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