Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1993-03-12
1994-08-02
Lone, Werren B.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568715, 568811, 568812, C07C 3328, C07C 3348
Patent
active
053347765
DESCRIPTION:
BRIEF SUMMARY
FIELD OF INDUSTRIAL APPLICATION
The present invention relates to a novel compound having a diethynylbenzene skeleton. The compound can be used for the separation of various mixtures which are otherwise difficult to separate and therefore can be utilized in the field of fine chemicals.
PRIOR ART
There have been known several substances (hereinafter called "host compounds" which have a property of combining with a separable compound (hereinafter called "a guest compound" contained in a mixture at a stoichiometric ratio to form a crystal (clathrate compound) and, therefore, have a capacity of separating the guest compound only from the mixture. Examples of such host compounds include compounds represented by the following formula (II): ##STR2## (wherein Ar and Ar' are each an aromatic group). Particularly when these host compounds are optically active substances, they are effective in the separation of optical isomers, which are generally thought to be extremely difficult to separate. However, the kinds of compounds which can be separated by these host compounds were limited.
DISCLOSURE OF INVENTION
An object of the present invention is to develop a novel host compound for the purpose of increasing the kinds of compounds which can be separated.
The present inventors have extensively studied to attain the above object. As the result, they have succeeded in developing a novel host compound which is different from those of the prior art with respect to the kinds of guest compounds, i.e., objects of separation, by modifying the diacetylene moiety of the host compound represented by the above formula (II) to thereby change the distance between the diarylhydroxymethyl groups present at both ends. The present invention has been accomplished on the basis of this success.
Thus, the present invention relates to a compound represented by the general formula (I) and a separating agent comprising the same: ##STR3##
(wherein Ar and Ar' are each an aromatic group; the positional relationship of the two substituents on the central benzene ring may be any of ortho, meta and para).
In the general formula (I), aromatic groups represented by Ar and Ar' may be the same or different from each other and each aromatic group preferably has at most 10 carbon atoms. Examples of such an aromatic group include a phenyl group and .alpha.- and .beta.-naphthyl groups and groups derived therefrom by substitution (such as an o-chlorophenyl group). The groups derived therefrom may be substituted by any substituents at any position, so far as the ability of the resulting compound as a host compound is not impaired. The structures and stereochemical characteristics of the diarylhydroxymethyl groups present at both ends have a great influence on the separating power of the host compound. When the compound represented by the general formula (I) is used for separation of chemically different substances, for example, that of a mixture of substances having boiling points close to each other or that of a mixture of diastereomers, the absolute configurations of both terminal groups in the case wherein Ar and Ar' are different from each other are not particularly limited, so that the compound may be a so-called mesoisomer wherein one of the terminal groups has R-configuration and the other has S-configuration, or may be a substance wherein both terminal groups have R-configuration, one wherein both terminal groups have S-configuration, an equivalent mixture of both substances, i.e., a so-called racemic modification, or a substance wherein Ar and Ar' may be the same. On tile other hand, when the compound is used for the separation of optical isomers, which is a more sophisticated separation, tile compound must be one wherein Ar and Ar' are different from each other and both terminal groups have either of R- and S-configurations, i.e., the compound must be optically active.
The compound represented by the above general formula (I) can be most easily prepared by conducting a double coupling reaction, as represented by the following reaction formula,
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Daicel Chemical Industries Ltd.
Lone Werren B.
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