Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1992-10-27
1994-10-11
Brown, Johnnie R.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 53, 536 553, 536124, 536 20, 536 56, 536112, C08B 3700, C07H 100
Patent
active
053548523
DESCRIPTION:
BRIEF SUMMARY
FIELD OF INDUSTRIAL APPLICATION
The present invention relates to a polysaccharide derivative, a process for producing the same, and a separating agent.
PRIOR ART
It is known that a packing material for liquid chromatography wherein use is made of a stationary phase comprising a silica gel and, supported thereon, an ester of a polysaccharide and a carbamate has an excellent capability of optical resolution (see Japanese Patent Publication-A No. 289601/1990 ). The silica gel used as a support, however, is very expensive. A process for producing a particulate cellulose ester of an aromatic or araliphatic carboxylic acid is well known in the art (see Japanese Patent Publication-A No. 152101/1989). However, a particulate aromatic or araliphatic carbamate of a polysaccharide has not been produced because the production thereof was difficult due to the limitation of the solubility and the solvent therefor.
DISCLOSURE OF THE INVENTION
The present inventors have made extensive studies with a view to solving the above-described problems and, as a result, have found that a particulate aromatic or araliphatic carbamate of a polysaccharide can be easily prepared, has an excellent capability of resolution because it is in the particulate form, particularly has a separation factor larger than that of the carbamate carried on a support, and is suitable for use in preparative liquid chromatography, thus accomplishing the present invention.
Accordingly, the present invention provides a polysaccharide derivative comprising a particulate aromatic or arallphatic carbamate of a polysaccharide having a mean particle diameter of 1 to 200 .mu.m and a specific surface area of 0.5 to 300 m.sup.2 /g, a process for producing the same, and a separating agent comprising said polysaccharide derivative for use in the separation of racemic compounds and structural isomer mixtures, particularly a separating agent for use as a stationary phase in chromatography.
In the present invention, the mean particle diameter of the polysaccharide derivative is 1 to 200 .mu.m, although it depends upon the application, preferably 3 to 20 .mu.m for analytic applications and 10 to 200 .mu.m for preparative applications. It is possible to attain a very narrow mean particle diameter range by fractionation through the use of a conventional method, for example, sedimentation, sifting or centrifugation by means of a cyclone.
The specific surface area of the polysaccharide derivative according to the present invention is 0.5 to 300 m.sup.2 /g, preferably 1 to 80 m.sup.2 /g. The particle is spherical or crushed in its shape, preferably spherical. The surface of the particle may be porous or non-porous, preferably porous for the purpose of increasing the absorption area and improving the performance of separation. The particle diameter distribution is preferably narrow when the particle is used as a separating agent for chromatography.
The aromatic or arallphatic carbamate of a polysaccharide of the present invention is derived from an lsocyanate represented by the following formulas (1) or (2): have a heteroatom and may be unsubstltuted or substituted with at least one member selected from the group consisting of a hydrocarbon group having 1 to 12 carbon atoms and optionally a heteroatom, a cyano group, a halogen atom, a hydroxy group, a nitro group, an amino group and a di(C.sub.1 to C.sub.8 alkyl) amino group; and
X stands for a divalent hydrocarbon group which has 1 to 4 carbon atoms and which may have a double bond or a triple bond).
Examples of the monovalent aromatic hydrocarbon group represented by the R include groups such as phenyl, naphthyl, phenanthryl, anthracyl, indenyl, indanyl, furyl, thionyl, pyrryl, benzofuryl, benzthionyl, indyl, pyridyl, pyrimidyl, quinolinyl and isoquinolinyl.
Examples of the substituents of the monovalent aromatic hydrocarbon group represented by the R include an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms, a cyano group, a halogen
REFERENCES:
patent: 4861872 (1989-08-01), Okamoto et al.
patent: 4912205 (1990-03-01), Okamoto et al.
patent: 5026841 (1991-06-01), Francotte et al.
patent: 5202433 (1993-04-01), Okamoto et al.
Database WPI, Week 8817, Derwent Publications Ltd.
Brown Johnnie R.
Daicel Chemical Industries Ltd.
White Everett
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