Daicel Chemical Industries, Ltd.

Kurita Water Industries Ltd.

Ube Industries, Inc.

Sumitomo Chemical Company, Limited

Mitsubishi Gas Chemical Company, Inc.

Otsuka Kagaku Kabushiki Kaisha

Mitsubishi Corporation

Osaka Soda Co., Ltd.

Fumio Toda

Koichi Tanaka

Masayoshi Minai

Kikuo Ataka

Kenji Tahara

Ayako Sekikawa

Hideo Sugi

Michio Sasaoka

Masatoshi Taniguchi

Minoru Yagi

Tetsuya Nakata

Fujiaki Mochizuki

Masaru Okamoto

Kouichi Tanaka

Yorihiko Inoue

A compound represented by the general formula (I) and a separating agent comprising the same: ##STR1## wherein Ar and Ar' are each an aromatic group; and the positional relationship of the two substituents on the central benzene ring may be any of ortho, meta and para. The above compound is effective in the separation and purification of many compounds to and enables the provision of various compounds (such as intermediates of drugs) which are useful in the field of fine chemicals, particularly optically active substances, at high purities and in large amounts.

Compound and separating agent

A process for producing optically active 4-hydroxy-2-cyclopentenone [1] which comprises reacting 4-hydroxy-2-cyclopentenone represented by the formula: ##STR1## with an optically active propargyl alcohol derivative represented by the general formula: ##STR2## wherein R and R.sup.1 each independently represent a halogenated phenyl group, an alkylphenyl group, or an alkyl group which may be substituted with one or more halogen atom(s), and * indicates an asymmetric carbon atom, to form an optically active complex [3] consisting essentially of optically active 4-hydroxy-2-cyclopentenone represented by the formula [1] ##STR3## wherein * indicates an asymmetric carbon atom, and the optically active propargyl alcohol derivative [2], and then decomposing the optically active complex [3].

Process for producing optical active 4-hydroxy-2-cyclopentenone

A d- or l-tartaric acid amide derivative serving as a host compound and a method of producing the amide derivative which combines with a guest compound to form a clathrate compound and which is expressed by the following Formula (A) or (B): ##STR1##

Tartaric acid amide derivative and method of producing the same

A biphenyl compound having the formula (I) is newly separated into its optical active compound, and useful as an optically separating agent: ##STR1## wherein W, X and Y are each an atom or atomic group selected from among H, F, Cl, Br, I, CH.sub.3, CF.sub.3, OH, OCH.sub.3, NH.sub.2 and N(CH.sub.3).sub.2 and Z is an atom or atomic group selected from among Cl, Br, I, CH.sub.3 and OCH.sub.3, R is an atomic group having 1 to 20 carbon atoms and containing a polar functional group selected from among ##STR2##

Optically active biphenyl derivative and process for optical resolution

A biphenyl compound having the formula (I) is newly separated into its optical active compound and useful as an optically separating agent: ##STR1## wherein W, X and Y are each an atom or atomic group selected from among H, F, Cl, Br, I, CH.sub.3, CF.sub.3, OH, OCH.sub.3, NH.sub.2 and N(CH.sub.3).sub.2 and Z is an atom or atomic group selected from among Cl, Br, I, CH.sub.3 and OCH.sub.3, R is an atomic group having 1 to 20 carbon atoms and containing a polar functional group selected from among ##STR2##

2,2'-Bis(.alpha.-hydroxydiphenylemthyl)biphenyl of formula: ##STR1## Clathrate compound is composed of the above compound as the host compound and a microbicide, 5-chloro-2-methyl-4-isothiazolin-3-one as the guest compound. The compound is formed such that, where diphenic acid is reacted with an alcohol for diesterification and then reacted with a Grignard reagent comprising a phenylmagnesium halide.

Clathrate compound

A process of separation and purification of a propargyl alcohol which comprises treating a propargyl alcohol represented by Formula (I): ##STR1## wherein each of R.sub.1 and R.sub.2 represents a substituent which is different from each other, and is selected from the group consisting of a C.sub.1 -C.sub.8 alkyl group, a phenyl group; a halophenyl group, a phenyl group having at least one methyl substituent, an aralkyl group and a cycloalkyl group, which is chemically or optically impure, with a tertiary diamine represented by Formula (II): ##STR2## wherein each of R.sub.3, R.sub.4, R.sub.5 and R.sub.6 may be the same or different and represents an aralkyl group or an alkyl group having 1 to 6 carbon atoms; and R.sub.3, R.sub.4, R.sub.5 and R.sub.6 may be bonded to each other, to form a crystalline complex compound of the propargyl alcohol represented by Formula (I) and the tertiary diamine represented by Formula (II), separating and purifying the resulting compound, and treating the resultant compound with an acid to isolate the propargyl alcohol represented by Formula (I).

Process of separation and purification of a propargyl alcohols

A method for producing an optically active 2-cyclopenten-4-one-1-ol ester useful as an intermediate for medicines, agricultural chemicals and represented by the general formula (I), ##STR1## wherein R represents a saturated or unsaturated aliphatic hydrocarbon residue which may or may not be substituted with a halogen atom, and a mark * represents an asymmetric carbon, which comprises bringing a 2-cyclopenten-4-one-1-ol ester represented by the general formula ##STR2## wherein R represents a saturated or unsaturated aliphatic hydrocarbon residue which may or may not be substituted with a halogen atom, into contact with an optically active 1,6-diphenyl-2,4-hexadiyne-1,6-diol derivative represented by the general formula (II), ##STR3## wherein R' represents a halogenated phenyl, lower alkylphenyl, naphthyl or tertiary lower alkyl group, and a mark * represents an asymmetric carbon, in an organic solvent to obtain an optically active cyclopentenone ester complex which is a bound product of the optically active 2-cyclopenten-4-one-1-ol ester represented by the foregoing general formula (I) with the optically active 1,6-diphenyl-2,4-hexadiyne-1,6-diol derivative represented by the foregoing general formula (II), and then decomposing the resulting optically active cyclopentenone ester complex.

Method for producing optically active 2-cyclopenten-4-one-1-ol esters,

An optically active substance having an optical purity of at least 50% e.e. is obtained by an asymmetric photochemical reaction by converting a starting, achiral material in a chiral crystalline form and irradiating light to the chiral crystalline form to effect the photocyclization of the starting material.

Asymmetric photochemical reaction process

Disclosed are a crystalline complex compound of a propargyl alcohol represented by Formula (I): ##STR1## wherein each of R.sub.1 and R.sub.2 represents a substituent which is different from each other and a tertiary diamine represented by Formula (II): ##STR2## wherein A represents a group having two carbon atoms as a chain member which may be branched; each of R.sub.3, R.sub.4, R.sub.5 and R.sub.6 may be the same or different and represents an aralkyl group or an alkyl group having 1 to 6 carbon atoms; and A, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 may be bonded to each other, and a process of separation and purification of the propargyl alcohol using the crystalline complex compound described above.

Crystalline complex compounds of propargyl alcohols and tertiary

Disclosed is a method of producing an optically active .beta.-lactam derivative of the formula ##STR1## comprising irradiating with light, in solid phase, an inclusion complex of a compound of the formula ##STR2## with an optically active host compound.

Method of producing optically active .beta.-lactam derivatives

A method of optically resolving a racemate, or a diastereomeric mixture, of a substituted or unsubstituted glycidyl ester or ether compound having at least one glycidylic structure represented by the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3, independently from each other, represent H or CH.sub.3, and 1 to 3 asymmetric carbon atoms in the molecule, or a racemate of a beta-dihalohydrin ester compound, which comprises contacting said racemate or diastereomeric mixture with an optically active form of a compound having the following formula (I) ##STR2## wherein X represents a halogen atom, to form an inclusion complex compound having the optically active compound of formula (I) as a host, and separating the resulting complex compound.

Method of optically resolving a racemate or a diastereomeric mixture of

Diphenic acid bis(dicyclohexylamide) represented by the following formula: ##STR1## A process for producing diphenic acid bis(dicyclohexylamide) represented by the above formula, which comprises dimerizing a diazonium salt of o-aminobenzoic acid in the presence of a reducing agent, followed by acidification to give 2,6'-dicarboxylbiphenyl; converting this dicarboxylic acid to 2,6'-dichloroformylbiphenyl by chlorination; and reacting this acid chloride with dicyclohexylamine. Sustained release antimicrobial compositions comprising a clathrate compound consisting of a microbial agent and diphenic acid bis(dicyclohexylamide) represented by the above formula.

Diphenic acid bis(dicyclohexylamide) for clothrate compound, process for

This invention provides novel N-cyclohexyl-polycarboxamide compounds having inclusion power for a variety of compounds, the N-cyclohexyl-polycarboxamide compound being of the general formula ##STR1## where R is a benzene ring, an ethylidene group, a benzylidene group, a 1,2-cyclohexylene group, a 1,2-cyclohexenylene-4 group, or a 2,3-, 2,5- or 2,6-pyridinediyl group, and n is equal to 2, 3 or 4 when R is a benzene ring, and equal to 2 when R is one of the aforesaid groups excluding a benzene ring. These compounds exhibit the host function of taking up a variety of compounds as guest compounds to form inclusion complexes, and can be utilized for the separation and purification thereof.

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Ehime, Japan

Fumio Toda