JPH06154591A - Optical isomer resolving agent and manufacture of the same - Google Patents

Abstract

PURPOSE:To provide an optical isomer resolving agent having good resolving power for a mixture of various kinds of optical isomers and a method for making the agent. CONSTITUTION:An optical isomer resolving agent is composed of an inorganic laminar compound (A) selected from sodium hectolite, gamma-zirconium phosphate, and hydrotalcite and an optically active organic compounds (B) having an asymmetric carbon atom linked to a cationic or anionic group selected from (R)-1- phenylethylamine hydrochloride and sodium (S)-1-phenylpropionate. The optical isomer resolving agent characterized by containing the organic compound (B) and the optically active organic compound (B) having the asymmetric carbon atom linked to a cationic or anionic group are intercalated between the layers of the inorganic laminar compound (A).

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to an optical isomer resolving agent and a method for producing the same, and more specifically, to an optical isomer resolving agent having a good optical isomer resolving ability for various optical isomer mixtures. The manufacturing method is related.

[0002]

2. Description of the Related Art In recent years, optical resolution of a mixture of optical isomers has been
It has become a very important technology in the fields of pharmaceuticals, agricultural chemicals, food additives, etc. Examples of the method for optically resolving an optical isomer mixture include (1) mechanical separation method: a method in which an optical isomer mixture is spontaneously crystallized and the obtained crystal is mechanically selected and optically resolved; ) Preferential crystallization method: A method in which crystals of either one of the optical isomers are inoculated as seeds, and only the enantiomer of the inoculated one is preferentially crystallized for optical resolution; (3)
Diastereomeric method: A method of reacting an optical isomer mixture with an optical resolving agent, and performing optical resolution by utilizing the difference in the physical properties of the diastereomers produced;
A method of optically resolving by utilizing the digestive function of a microorganism or an asymmetric hydrolysis action of an enzyme; (5) A method of optically resolving by an optical isomer resolving agent having an asymmetric structure.

However, the above-mentioned (1) mechanical separation method, (2) preferential crystallization method and (3) diastereomer method are complicated in operation,
There is a problem that it takes time to determine the conditions for optical resolution, and it can be applied only to the optical resolution of a specific optical isomer mixture. Further, the above-mentioned (4) fermentation method and enzyme method have problems that it is difficult to control microorganisms and enzymes and that they can be applied only to optical resolution of specific optical isomers.

On the other hand, the method (5) for optical resolution with an optical isomer resolving agent having an asymmetric structure has the advantages that the operation is simple and the optical isomer mixture can be easily optically resolved. is there. Specific examples of the optical isomer resolving agent used for this purpose include an optical isomer resolving agent obtained by chemically bonding an optically active organic group to the surface of a silica carrier. As an optical isomer resolving agent composed of a carrier other than silica, Yamagishi's intercalation of an optically active metal complex compound with a layered clay compound.
n: an optical isomer resolving agent formed by inserting molecules, atoms or ions between layers of a substance having a layered structure [Inorganic Chemistry
mistry), 25, 55, 1986].

However, the optical isomer resolving agent comprising a silica carrier has a problem that its production is difficult and the kind or structure of the optical isomer mixture to be optically resolved is limited. On the other hand, the optical isomer resolving agent reported by Yamagishi has a problem that its use is limited to optical resolution of a metal complex. Further, in the method for producing this optical isomer resolving agent, the kind of compound introduced between the layers of the layered clay compound is limited to an optically active metal complex, and it is very difficult to synthesize and purify this optically active metal complex. There is a problem that it is difficult and requires high technology for its preparation.

[0006]

DISCLOSURE OF INVENTION Problems to be Solved by the Invention The inventors of the present invention have conducted extensive studies on an optical isomer resolving agent capable of optically resolving a mixture of various optical isomers, and as a result, as a result, a cationic cation between the layers of the inorganic layered compound It was found that an inorganic layered compound containing an optically active organic compound having an asymmetric atom bonded to a group or an anionic group has good optical isomer resolution for various optical isomer mixtures. ,
The present invention has been reached.

That is, an object of the present invention is to provide an optical isomer separating agent having a good optical isomer resolving ability for various optical isomer mixtures and a method for producing the same.

[0008]

Means for Solving the Problem and Its Action The present invention provides an optical isomer comprising (A) an inorganic layered compound and (B) an optically active organic compound having an asymmetric atom bonded to a cationic group or an anionic group. A body resolving agent, an optical isomer resolving agent characterized by containing the (B) organic compound between the layers of the (A) inorganic layered compound, and (A) an inorganic layered compound (B) cation The present invention relates to a method for producing an optical isomer resolving agent, which comprises intercalating an optically active organic compound having an asymmetric atom bonded to an acidic group or an anionic group.

First, the optical isomer resolving agent of the present invention will be described in detail.

The optical isomer resolving agent of the present invention comprises an inorganic layered compound of component (A) and an optically active organic compound having an asymmetric atom bonded to a cationic group or anionic group of component (B), It is characterized by containing the component (B) between the layers of the component (A). The inorganic layered compound as the component (A) is a base material of the optical isomer resolving agent of the present invention, and the kind thereof is not particularly limited, and may be a compound generally classified as an inorganic layered compound. Specific examples of the inorganic layered compound as the component (A) include clay minerals such as montmorillonite, vermiculite, kaolinite, halloysite, and hectorite, transition metals such as graphite, zirconium phosphate, molybdenum sulfide, and tantalum sulfide, and metal phosphorus. Examples include chalcogen compounds, transition metal oxychlorides such as iron hypochlorite and vanadium hypochlorite; cation-exchangeable inorganic layered compounds such as layered silicates, and anion-exchangeable inorganics such as hydrotalcite. A layered compound is exemplified.

The property of the component (A) is not particularly limited, and its form may be powdery, granular or plate-like, and is easy to handle and versatile such as a chromatography packing material. It is preferably a granulate having a particle size of 10 to 1000 mesh. Also, (A)
The component can easily intercalate the organic compound of the component (B) between the layers, and therefore has an ion-exchange capacity of 0.1 milliequivalent (meq) / g or more. It is preferable.

The organic compound as the component (B) is a component for imparting good optical isomer resolution to the obtained inorganic layered compound by being contained between the layers of the component (A). (B)
The optically active organic compound having an asymmetric atom bonded to the cationic group or anionic group of the component is not particularly limited in its optical purity as long as it has optical activity. Since the optical isomer resolution of the isomer resolving agent is high, the optical purity is more preferably 90%.
ee (enantiomer exess: e
e) or more. The type of component (B) is not particularly limited. The optical isomer resolving agent of the present invention is capable of selectively optically resolving optical isomers having the same optical activity as the optical activity of the component (B) contained between the layers of the inorganic layered compound of the component (A). Therefore, the component (B) having the same optical characteristics as the optical isomer to be optically resolved can be selected.

When the component (A) is a cation-exchangeable inorganic layered compound, the organic compound of the component (B) contained between the layers is an optically active organic compound having an asymmetric atom bonded to a cationic group. Is preferred and preferred
Specifically as the organic compound of the component (B), (R) -1-
Phenylethylammonium or (S) -1-phenylethylammonium, (R) -1-tolylethylammonium or (S) -1-tolylethylammonium, (R) -1-naphthylethylammonium or (S) -1- Naphthylethylammonium, (R)-
Organic ammonium such as 2,2′-diammonium-1,1′-binaphthyl or (S) -2,2′-diammonium-1,1′-binaphthyl; D-phenylglycine methyl ester cation, L-phenylalanine ethyl Examples thereof include amino acid ester cations such as ester cation, L-tryptophan methyl ester cation, L-leucine ethyl ester cation, and L-tyrosine ethyl ester cation; sugar derivative cations such as L-glucamine cation and D-glucosamine cation.

When the component (A) is an anion-exchangeable inorganic layered compound, the organic compound of the component (B) is
It is preferable to use an optically active organic compound having an asymmetric atom bonded to an anionic group, and this preferable (B)
Specific examples of the organic compound as the component include (R) -1-phenylethylcarboxylic acid anion or (S) -1-phenylethylcarboxylic acid anion, (R) -1-tolylethylcarboxylic acid anion or (S)- Examples thereof include 1-tolylethylcarboxylic acid anion, (R) -1-naphthylethylcarboxylic acid anion, and (S) -1-naphthylethylcarboxylic acid anion.

Next, the method for producing the optical isomer resolving agent of the present invention will be described in detail.

The production method of the present invention is characterized in that (A) an inorganic layered compound is intercalated with (B) an optically active organic compound having an asymmetric atom bonded to a cationic group or an anionic group. .

The inorganic layered compound of the component (A) used in the production method of the present invention is not particularly limited as long as it is a compound generally classified as an inorganic layered compound. Specific examples of the inorganic layered compound include clay minerals such as montmorillonite, vermiculite, kaolinite, halloysite, and hectorite; transition metal dichalcogen compounds such as graphite, zirconium phosphate, molybdenum sulfide, and tantalum sulfide; metal phosphorus chalcogen compounds; Examples include transition metal oxychlorides such as iron chlorate and vanadium hypochlorite; cation-exchangeable inorganic layered compounds such as layered silicic acid, and anion-exchangeable inorganic layered compounds such as hydrotalcite. .

Also used in the manufacturing method of the present invention,
The organic compound of the component (B) is not particularly limited as long as it is an optically active organic compound having an asymmetric atom bonded to a cationic group or an anionic group, and specific examples of the organic compound of the component (B) are as follows. Includes (R) -1-phenylethylamine hydrochloride or (S) -1-phenylethylamine hydrochloride, (R) -1-tolylethylamine bromate or (S) -1-tolylethylamine bromate, ( R) -1
-Naphthylethylamine hydrochloride or (S) -1-naphthylethylamine hydrochloride, (R) -2,2'-diamino-1,1'-binaphthyl hydrochloride or (S) -2,2 '
-Organoammonium salts such as diamino-1,1'-binaphthyl hydrochloride, D-phenylglycine methyl ester hydrochloride, L-phenylalanine ethyl ester hydrochloride, L-
Examples thereof include amino acid ester hydrochlorides such as tryptophan methyl ester hydrochloride, L-leucine ethyl ester hydrochloride and L-tyrosine ethyl ester hydrochloride; sugar derivatives such as L-glucamine hydrochloride and D-glucosamine hydrochloride.

In the production method of the present invention, the component (A) and the component (B)
The charged amount with the component is not particularly limited, and the charged amount of the component (B) is preferably an amount equal to or more than the ion exchange amount of the component (A). Further, in the production method of the present invention, the particle size of the component (A) is a granular material having a particle size of 10 to 1000 mesh (mesh) because it is easy to handle and versatility such as a chromatography filler is excellent. Preferably there is.
Moreover, since the component (B) can be easily intercalated between the layers of the component (A), the ion-exchange capacity of the component (A) is 0.1 meq.
It is preferably (meq) / g or more.

In the production method of the present invention, the component (A) is (B)
As a method of intercalating the components, for example, the inorganic layered compound of the component (A) is dispersed in a polar solvent,
Next, a method of adding the component (B) to this and reacting it, and a method of reacting the inorganic layered compound of the component (A) and the organic compound of the component (B) in the absence of a solvent are mentioned. In the production method of the present invention, the type of polar solvent that can be used is not particularly limited, and specific examples of such a polar solvent include water; methanol,
Examples thereof include alcohol solvents such as ethanol, i-propyl alcohol, n-propyl alcohol, t-butyl alcohol, n-butyl alcohol, diethylene glycol and glycerin; acetonitrile, dimethylformamide and dimethyl sulfoxide.

In the production method of the present invention, the reaction time is not particularly limited, and it is preferable that the organic compound of the component (B) reacts between the layers of the inorganic layered compound of the component (A) until it becomes saturated. In the production method of the present invention, the progress of the reaction can be confirmed by measuring the concentration of the unreacted component (B) or in the optical isomer resolving agent of the present invention, by measuring the bottom distance between the layers. it can. Further, the reaction temperature is not particularly limited, preferably in the range of room temperature to 150 ° C., in order to promote the reaction of intercalating the organic compound of the component (B) with the inorganic layered compound of the component (A), a mechanical It is possible to irradiate the reaction system with ultrasonic waves or microwaves as well as to perform the agitation. Further, in the production method of the present invention, between the layers of the inorganic layered compound of the component (A)
By intercalating an organic compound other than the component (B),
Then, the organic compound of the component (B) can be intercalated into this.

The optical isomer resolving agent of the present invention is characterized by containing an optically active organic compound of the component (B) between the layers of the component (A), and therefore it exists naturally as the component (B). An optically active organic compound or an organic compound that is easily asymmetrically synthesized can be used. Further, the thus obtained optical isomer resolving agent of the present invention can efficiently perform optical resolution of various optical isomer mixtures. The optical isomer optically resolved by the optical isomer resolving agent of the present invention is not particularly limited, and such an optical isomer is 1
Amines such as -phenylethylamine and 1-amino-3-methylhexane; 1-phenylethyl alcohol,
Examples include alcohols such as 3,7-dimethyloctane-1-ol and 3-methylcyclohexanol; other diols, ketones, amino acids, monosaccharides and the like.

The optical isomer resolving agent of the present invention is, for example, an optical resolution of an optical isomer mixture by a batch method: the optical isomer resolving agent of the present invention and an organic solution of the optical isomer mixture are mixed and stirred to obtain an optical isomer. Method for filtering isomer resolving agent; Optical resolution of optical isomer resolving agent by chromatographic method: A column is uniformly packed with the optical isomer resolving agent of the present invention, and then this is applied to a gas chromatography or liquid chromatography apparatus. It can be applied to a method of connecting and optically resolving an optical isomer mixture. In this way
With the optical isomer resolving agent of the present invention, one of the optical isomers can be selectively incorporated into the layered compound to improve the optical purity of the other optical isomer.

The optical isomer resolving agent of the present invention will be described in detail with reference to Examples.

[0025]

Example 1 In a 200 ml triangular flask, the particle size was about 1
5.0 g of sodium hectorite having a mesh size of 00 mesh or less and a cation exchange amount of about 0.88 meq / g is added, about 100 ml of ion-exchanged water is added, and the mixture is stirred at room temperature for about 12 hours. did. It was confirmed that this dispersion was uniform, and then (R) having an optical purity of 99% ee.
-1-phenylethylamine hydrochloride 0.63 g of 5 ml
The aqueous solution was added and well stirred for about 3 hours. Then, the reaction solution is suction-filtered using a filter paper to remove unreacted (R) -1-phenylethylamine hydrochloride and (R) -1-phenylethylamine hydrochloride physically adsorbed on the hectorite surface. Each was washed with 100 to 200 ml of ion-exchanged water and ethanol. Then, the treated hectorite was placed in a desiccator containing silica gel and dried under reduced pressure at room temperature overnight to prepare an optical isomer resolving agent of the present invention.

The elemental analysis values of this optical isomer resolving agent were carbon 4.29% and nitrogen 0.51%. The bottom spacing was 1.48 as determined by X-ray diffraction of this optical isomer resolving agent.
nm, which is larger than the bottom spacing of 1.23 nm of the raw material sodium hectorite, and it was confirmed by cation exchange that (R) -1-phenylethylammonium was contained between the layers of hectorite.

Next, the optical isomer resolving ability of this optical isomer resolving agent was evaluated by the batch method. The evaluation method is as follows. 1.15 g of this optical isomer resolving agent was put into a sample bottle of about 15 ml, and the enantiomer excess (enantiomer exess; ee) was 1.9% as S form.
6.00 g of a cyclohexane solution having a concentration of 2.75 × 10 ⁻² mol / liter of an optical isomer mixture of (R, S) -1-phenylethylamine, which is ee, was added, and the mixture was stirred and mixed at room temperature for 5 minutes. When the enantiomeric excess of the filtrate was measured by removing the optical isomer resolving agent by filtration, the optical purity of the R isomer was 56.3% ee. Enantiomeric excess is measured by gas chromatography (column; Chromp
ack CP-Cyclodex β 236M, 50m × 0.25mm).

[0028]

Example 2 In a 200 ml triangular flask, the particle size was about 1
5.0 g of sodium hectorite having a mesh size of 00 mesh or less and a cation exchange amount of about 0.88 meq / g is added, about 100 ml of ion-exchanged water is added, and the mixture is stirred at room temperature for about 12 hours. did. It was confirmed that this dispersion was uniform, and then a 5 ml aqueous solution of 0.83 g of (S) -1-naphthylethylamine hydrochloride having an optical purity of 99% ee was added and stirred for about 3 hours. Then, the reaction solution is suction-filtered using a filter paper to obtain unreacted (S) -1-
In order to remove naphthylethylamine hydrochloride and (S) -1-naphthylethylamine hydrochloride physically adsorbed on the surface of hectorite, they were washed with 100 to 200 ml of ion-exchanged water and ethanol, respectively. Then, the treated hectorite was placed in a desiccator containing silica gel and dried under reduced pressure at room temperature overnight to prepare an optical isomer resolving agent of the present invention.

The elemental analysis values of this optical isomer resolving agent were carbon 6.40% and nitrogen 0.64%. In addition, the bottom distance between the optical isomer resolving agents was 1.
It was 62 nm, which was larger than the bottom spacing of 1.23 nm of sodium hectorite as a raw material, and it was confirmed by cation exchange that (S) -1-naphthylethylammonium was contained between the layers of hectorite.

Next, the optical resolution of this optical isomer resolving agent was evaluated by the batch method. The evaluation method is as follows. 1.15 g of this optical isomer resolving agent was placed in a 15 ml sample bottle, and the enantiomeric excess (enan
tio-mer exess; ee) is 1.9% ee as S isomer, and a mixture of optical isomers of (R, S) -1-phenylethylamine 2.75 × 10 ⁻² mol / l cyclohexane solution 6. 00 g was added, and the mixture was stirred and mixed at room temperature for 5 minutes. The optical isomer resolving agent was removed by filtration, and the enantiomer excess of the filtrate was measured.
It was 4.0% ee. Enantiomeric excess is measured by gas chromatography (column; Chrompack CP-Cycl
The measurement was carried out with odex β 236M, 50 m × 0.25 mm).

[0031]

Example 3 In a 200 ml triangular flask, the particle size was about 8
5.0 g of γ-zirconium phosphate having a mesh size of 0 mesh or less and a cation exchange amount of about 6.27 meq / g is added, and about 100 ml of ion-exchanged water is added to the mixture at room temperature for about 12 Stir for hours. It was confirmed that this dispersion was uniform, and then (R) having an optical purity of 99% ee.
50 g of -1-phenylethylamine hydrochloride was added and reacted for 3 hours under ultrasonic irradiation. Then, the reaction solution is suction-filtered using a filter paper to remove unreacted (R) -1-phenylethylamine hydrochloride and (R) -1-phenylethylamine hydrochloride physically adsorbed on the hectorite surface. 100-200 ml of deionized water,
It was washed with ethanol. Then, the treated γ-zirconium phosphate was placed in a desiccator containing silica gel and dried under reduced pressure at room temperature overnight to prepare an optical isomer resolving agent of the present invention.

The elemental analysis values of this optical isomer resolving agent were as follows: carbon 9.20% and nitrogen 1.09%. In addition, the bottom distance between the optical isomer resolving agents was 1.
It is 83 nm, which is larger than the bottom distance of 1.17 nm of γ-zirconium phosphate as a raw material, and (R)-between the layers of γ-zirconium phosphate due to cation exchange.
It was confirmed that 1-phenylethylammonium was contained.

Next, by liquid chromatography,
The optical isomer resolution of this optical isomer resolving agent was evaluated.
The evaluation method is as follows. Inner diameter 4.0 mm, length 15
A cm column made of stainless steel was packed with this optical isomer resolving agent, a UV absorption spectrophotometer was used as a detector, and a 5% isopropanol-hexane solution was used as a developing solvent (R,
S) -1-Phenylethyl alcohol (R form 0.6% e
optical resolution of the optical isomer mixture consisting of e),
Separation was possible with a separation factor of 1.03. The solution after the division operation was S-isomer 48.3% ee.

[0034]

Example 4 In a 200 ml triangular flask, the particle size was about 1
5.0 g of hydrotalcite having a mesh size of 0 mesh or less and an anion exchange amount of about 1.60 meq / g was added, and about 100 ml of ion-exchanged water was added,
Stir at room temperature for about 12 hours. It was confirmed that this dispersion was uniform, and then 5 g of (R) -1-phenylpropionate sodium having an optical purity of 99% ee or higher was added, and the reaction was carried out at a temperature of 80 ° C. for 3 hours. Then, the reaction solution is suction-filtered using a filter paper to obtain unreacted (R) -1-
In order to remove sodium phenylpropionate and sodium (R) -1-phenylpropionate physically adsorbed on the surface of hydrotalcite, 100 to 20 each is removed.
It was washed with 0 ml of deionized water and ethanol. Then, the treated hydrotalcite was placed in a desiccator containing silica gel and dried under reduced pressure at room temperature overnight to prepare the optical isomer resolving agent of the present invention.

The elemental analysis values of this optical isomer resolving agent were as follows: carbon 18.31% and nitrogen 2.13%. Also this
According to X-ray diffraction of the optical isomer resolving agent, the bottom spacing is 1.42 nm, which is larger than the bottom spacing of the raw material hydrotalcite of 0.80 nm. R) -1-
It was confirmed that the phenylpropionate anion was contained.

Next, the optical resolution of this optical isomer resolving agent was evaluated by the batch method. The evaluation method is as follows. 1.15 g of this optical isomer resolving agent was placed in a 15 ml sample bottle, and the enantiomeric excess (enan
6.00 g of a cyclohexane solution having a concentration of 2.75 × 10 ^-2 mol / liter, which is an optical isomer mixture of (R, S) -1-phenylethyl alcohol, in which tiomer exess; ee) is 0.6% ee as R form. Was added and mixed with stirring at room temperature for 5 minutes. When the enantiomeric excess of the filtrate was measured by removing the optical isomer resolving agent by filtration, the optical purity of the R isomer was 78.3% ee. Enantiomeric excess was measured by gas chromatography (column; Chrompack C
The measurement was carried out with P-Cyclodex β 236M, 50m × 0.25mm).

[0037]

[Comparative Example 1] The particle size is about 1 in a 200 ml triangular flask.
5.0 g of sodium hectorite having a mesh size of 00 mesh or less and a cation exchange amount of about 0.88 meq / g is added, about 100 ml of ion-exchanged water is added, and the mixture is stirred at room temperature for about 12 hours. did. It was confirmed that this dispersion was uniform, and then 1.00 g of 2-phenylethylamine hydrochloride having an optical purity of 99% ee was added, and the temperature was adjusted to 8
The reaction was carried out at 0 ° C for 3 hours. Then, the reaction solution is suction-filtered using a filter paper, and is physically adsorbed on unreacted 2-phenylethylamine hydrochloride and the hectorite surface.
10 for each to remove phenylethylamine hydrochloride
It was washed with 0 to 200 ml of deionized water and ethanol. Then, the treated hectorite was placed in a desiccator containing silica gel and dried under reduced pressure at room temperature overnight to prepare a treated hectorite.

The elemental analysis values of this treated hectorite were carbon 4.33% and nitrogen 0.56%. In addition, the X-ray diffraction of this treated hectorite revealed that the bottom spacing was 1.5
It was 3 nm, which was larger than the bottom spacing 1.23 nm of sodium hectorite as a raw material, and it was confirmed by cation exchange that 2-phenylethylamine hydrochloride was contained between the layers of hectorite.

Next, the ability to resolve optical isomers of this treated hectorite was evaluated by the batch method. The evaluation method is as follows. 1.15 g of this treated hectorite was placed in a 15 ml sample bottle, and the enantiomer excess (ee) was 1.9% e as S form.
Then, 6.00 g of a cyclohexane solution having a concentration of 2.75 × 10 ^-2 mol / liter of the optical isomer mixture of (R, S) -1-phenylethylamine, which is e, was added, and the mixture was stirred and mixed at room temperature for 5 minutes. When the treated hectorite was removed by filtration and the enantiomeric excess of the filtrate was measured, it was confirmed that the optical purity of the S-form was 1.9% ee, and that this treated hectorite had no optical resolution. Enantiomeric excess is measured by gas chromatography (column; Chrompac
k CP-Cyclodex β 236M, 50 m × 0.25 mm).

[0040]

The optical isomer resolving agent of the present invention contains the organic compound of the component (B) between the layers of the inorganic layered compound of the component (A), and therefore, for various optical isomer mixtures, Having a good optical isomer resolution, and the production method of the present invention,
Such a novel optical isomer resolving agent of the present invention can be produced.

[Brief description of drawings]

FIG. 1 was used to evaluate the optical isomer resolving agent of the present invention,
3 is a gas chromatograph chart of (R, S) -1-phenylethylamine.

FIG. 2 is a gas chromatograph chart of the filtrate obtained by optical resolution using the optical isomer resolving agent prepared in Example 1.

FIG. 3 is a gas chart graph chart of the filtrate obtained by optical resolution using the optical isomer resolution agent prepared in Example 2.

[Explanation of symbols]

 (R): peak of (R) -1-phenylethylamine (S): peak of (S) -1-phenylethylamine

Claims (3)

[Claims] 1. An optical isomer resolving agent comprising (A) an inorganic layered compound and (B) an optically active organic compound having an asymmetric atom bonded to a cationic group or an anionic group, which comprises:
An optical isomer resolving agent comprising the organic compound (B) between the layers of the inorganic layered compound (A). 2. An optical isomer resolving agent characterized by intercalating (A) an inorganic layered compound with (B) an optically active organic compound having an asymmetric atom bonded to a cationic group or an anionic group. Manufacturing method. 3. The method for producing an optical isomer resolving agent according to claim 2, wherein the ion exchange capacity of the component (A) is 0.1 meq / g or more.