JPH11255689A - Sulfoxide group-containing molecular crystal and its production - Google Patents

Abstract

PROBLEM TO BE SOLVED: To produce the subject new stable and readily handleable molecular crystal by complexing an industrially useful sulfoxide group-containing compound using specific tetrakisphenols. SOLUTION: This molecular crystal comprises tetrakisphenols represented by the formula X is (CH2 )n [(n) is 0, 1, 2 or 3] or phenyl; R<1> and R<2> are each H, a lower alkyl, phenyl which may be substituted, a halogen or a lower alkoxy} and a sulfoxide group-containing compound. The molecular crystal is obtained by reacting the tetrakisphenols represented by the formula [e.g. 1,1,2,2-tetrakis(4-hydroxyphenyl)ethane] with the sulfoxide group-containing compound (e.g. dimethyl sulfoxide) in the presence of a reactional solvent (e.g. ethyl acetate). The resultant molecular crystal can be utilized and expected for the application to selective separation, chemical stabilization, etc., of the sulfoxide group-containing compound.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel molecular crystal comprising a tetrakisphenol and a sulfoxide group-containing compound and a method for producing the same, and more particularly, to a method for donating a proton to a sulfoxide group-containing compound which is a component compound of the molecular crystal. The present invention relates to a method for selectively producing a molecular crystal having a target specific sulfoxide group-containing compound as a component compound from a mixture of different types of sulfoxide group-containing compounds by selectively using various reaction solvents having different properties.

[0002]

2. Description of the Related Art A molecular crystal is a polymolecular crystal in which two or more compounds are bonded by a relatively weak interaction other than a covalent bond represented by a hydrogen bond, van der Waals force, or the like. Since it has the property of dissociating into the original component compounds, it is expected in recent years to be applied to technical fields such as selective separation of useful substances, chemical stabilization, non-volatization, sustained release, and powdering. An example of a specific molecular crystal is an inclusion crystal.
JP-53201 discloses 1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol or 1,1-di (2,4-dimethylphenyl) -2-propyne-1. And Japanese Patent Application Laid-Open No. 62-22701 discloses 1,1'-bis-2-naphthol and 5-
Inclusion crystals with chloro-2-methyl-4-isothiazolin-3-one and the like are described. Also, Japanese Patent Application Laid-Open No. 6-16 / 1994
No. 6646 discloses inclusion crystals of tetrakisphenols with various organic compounds.

The functions of molecular crystals including these inclusion crystals are as follows:
Since it depends on how the individual component compounds assemble, control of the assembling form is extremely important in producing molecular crystals. Tetrakisphenols, which lead to a variety of aggregate forms, are particularly useful as a central component in the formation of molecular crystals, but molecular crystals with a sulfoxide group-containing compound are not yet known.

Most of the sulfoxide group-containing compounds, such as dimethyl sulfoxide, are known as industrially important special solvents. On the other hand, the sulfoxide group-containing compound has a highly reactive, semipolar, polarized sulfoxide group. Therefore, it is regarded as important as a synthetic substrate. However, many of these sulfoxide group-containing compounds are chemically unstable,
It has many problems in storage and handling, such as strong skin irritation. Some molecular crystals using a sulfoxide group-containing compound as a component compound are already known (Japanese Patent Application Laid-Open No. 61-53201). However, in the prior art, a molecular crystal having a desired composition can be selected stably. However, it was not satisfactory in terms of manufacturing.

[0005]

An object of the present invention is to be expected to be applied in technical fields such as selective separation of industrially useful sulfoxide group-containing compounds, chemical stabilization, non-volatization, sustained release, and powdering. And a method for stably producing the molecular crystal with an intended composition.

[0006]

Means for Solving the Problems The present inventors have made intensive studies to solve the above-mentioned problems, and as a result, have found that certain tetrakisphenols easily form stable molecular crystals with a wide range of sulfoxide group-containing compounds. A tetrakisphenol and a sulfoxide group-containing compound are reacted with a sulfoxide group-containing compound in various reaction solvents having different proton donating properties, that is, a reaction solvent acting as a proton donor with respect to the sulfoxide group-containing compound, or a reaction solvent not acting as a proton donor It has been found that a molecular crystal having an intended composition can be produced extremely stably by properly using, and the present invention has been completed.

That is, the present invention relates to a molecular crystal comprising a tetrakisphenol represented by the general formula [1] and a compound containing at least one sulfoxide group in the molecule.

Embedded image (Wherein X represents (CH ₂ ) _n or a phenyl group;
Is 0, 1, 2, or 3, and R ¹ and R ² each represent a hydrogen atom, a lower alkyl group, an optionally substituted phenyl group, a halogen atom, or a lower alkoxy group. )

Further, the present invention is represented by the general formula [1], wherein the tetrakisphenol represented by the general formula [1] is reacted with a sulfoxide group-containing compound in the presence of a reaction solvent. The present invention relates to a method for producing a molecular crystal comprising a tetrakisphenol and a sulfoxide group-containing compound.

Further, the present invention provides a method for producing molecular crystals by reacting a tetrakisphenol represented by the above general formula [1] with two or more kinds of compounds having a sulfoxide group in the presence of a reaction solvent. By selectively using reaction solvents having different proton-donating properties for the group-containing compound, a molecular crystal having a specific sulfoxide group-containing compound as a component compound is selectively generated among two or more sulfoxide group-containing compounds. The present invention relates to a method for producing a molecular crystal comprising a tetrakisphenol represented by the general formula [1] and a compound having a sulfoxide group.

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION The tetrakisphenol used in the present invention is not particularly limited as long as it can be represented by the above general formula [1] and can form a molecular crystal with a sulfoxide group-containing compound. May be used alone or in combination of two or more.

Specific examples of the tetrakisphenols used in the present invention include 1,1,2,2-tetrakis (4-hydroxyphenyl) ethane, 1,1,1
2,2-tetrakis (3-methyl-4-hydroxyphenyl) ethane, 1,1,2,2-tetrakis (3,5-
Dimethyl-4-hydroxyphenyl) ethane, 1,1,
2,2-tetrakis (3-chloro-4-hydroxyphenyl) ethane, 1,1,2,2-tetrakis (3,5-
Dichloro-4-hydroxyphenyl) ethane, 1,1,
2,2-tetrakis (3-bromo-4-hydroxyphenyl) ethane, 1,1,2,2-tetrakis (3,5-
Dibromo-4-hydroxyphenyl) ethane, 1,1,
2,2-tetrakis (3-t-butyl-4-hydroxyphenyl) ethane, 1,1,2,2-tetrakis (3
5-di-t-butyl-4-hydroxyphenyl) ethane, 1,1,2,2-tetrakis (3-fluoro-4-
(Hydroxyphenyl) ethane, 1,1,2,2-tetrakis (3,5-difluoro-4-hydroxyphenyl)
Ethane, 1,1,2,2-tetrakis (3-methoxy-
4-hydroxyphenyl) ethane, 1,1,2,2-tetrakis (3,5-dimethoxy-4-hydroxyphenyl) ethane, 1,1,2,2-tetrakis (3-chloro-5-methyl-4-) Hydroxyphenyl) ethane, 1,
1,2,2-tetrakis (3-bromo-5-methyl-4
-Hydroxyphenyl) ethane, 1,1,2,2-tetrakis (3-methoxy-5-methyl-4-hydroxyphenyl) ethane, 1,1,2,2-tetrakis (3-t
-Butyl-5-methyl-4-hydroxyphenyl) ethane, 1,1,2,2-tetrakis (3-chloro-5-bromo-4-hydroxyphenyl) ethane, 1,1,2,2
2-tetrakis (3-chloro-5-phenyl-4-hydroxyphenyl) ethane, 1,1,2,2-tetrakis [(4-hydroxy-3-phenyl) phenyl] ethane, 1,1,3,3- Tetrakis (4-hydroxyphenyl) propane, 1,1,3,3-tetrakis (3-methyl-4-hydroxyphenyl) propane, 1,1,
3,3-tetrakis (3,5-dimethyl-4-hydroxyphenyl) propane, 1,1,3,3-tetrakis (3-chloro-4-hydroxyphenyl) propane,
1,1,3,3-tetrakis (3,5-dichloro-4-
Hydroxyphenyl) propane, 1,1,3,3-tetrakis (3-bromo-4-hydroxyphenyl) propane, 1,1,3,3-tetrakis (3,5-dibromo-
4-hydroxyphenyl) propane, 1,1,3,3-
Tetrakis (3-phenyl-4-hydroxyphenyl)
Propane, 1,1,3,3-tetrakis (3,5-diphenyl-4-hydroxyphenyl) propane, 1,1,
3,3-tetrakis (3-methoxy-4-hydroxyphenyl) propane, 1,1,3,3-tetrakis (3
5-dimethoxy-4-hydroxyphenyl) propane,
1,1,3,3-tetrakis (3-t-butyl-4-hydroxyphenyl) propane, 1,1,3,3-tetrakis (3,5-di-t-butyl-4-hydroxyphenyl) propane, 1,1,4,4-tetrakis (4-hydroxyphenyl) butane, 1,1,4,4-tetrakis (3-methyl-4-hydroxyphenyl) butane, 1,
1,4,4-tetrakis (3,5-dimethyl-4-hydroxyphenyl) butane, 1,1,4,4-tetrakis (3-chloro-4-hydroxyphenyl) butane,
1,4,4-tetrakis (3,5-dichloro-4-hydroxyphenyl) butane, 1,1,4,4-tetrakis (3-methoxy-4-hydroxyphenyl) butane,
1,1,4,4-tetrakis (3,5-dimethoxy-4
-Hydroxyphenyl) butane, 1,1,4,4-tetrakis (3-bromo-4-hydroxyphenyl) butane, 1,1,4,4-tetrakis (3,5-dibromo-
4-hydroxyphenyl) butane, 1,1,4,4-tetrakis (3-t-butyl-4-hydroxyphenyl)
Butane, 1,1,4,4-tetrakis (3,5-di-t
-Butyl-4-hydroxyphenyl) butane, α, α,
α ', α'-tetrakis (4-hydroxyphenyl)-
p-xylene, α, α, α ′, α′-tetrakis (3-
Methyl-4-hydroxyphenyl) -p-xylene,
α, α, α ', α'-tetrakis (3,5-dimethyl-
4-hydroxyphenyl) -p-ethane, α, α,
α ′, α′-Tetrakis (3-chloro-4-hydroxyphenyl) -p-xylene, α, α, α ′, α′-tetrakis (3,5-dichloro-4-hydroxyphenyl)
-P-xylene, α, α, α ′, α′-tetrakis (3
-Bromo-4-hydroxyphenyl) -p-xylene,
α, α, α ′, α′-tetrakis (3,5-dibromo-
4-hydroxyphenyl) -p-xylene, α, α,
α ', α'-tetrakis (3-t-butyl-4-hydroxyphenyl) -p-xylene, α, α, α', α '
(3,5-di-t-butyl-4-hydroxyphenyl)
-P-xylene, α, α, α ′, α′-tetrakis (3
-Fluoro-4-hydroxyphenyl) -p-xylene, α, α, α ′, α′-tetrakis (3,5-difluoro-4-hydroxyphenyl) -p-xylene, α,
α, α ′, α′-tetrakis (3-methoxy-4-hydroxyphenyl) -p-xylene, α, α, α ′, α ′
-Tetrakis (3,5-dimethoxy-4-hydroxyphenyl) -p-xylene, α, α, α ′, α′-tetrakis (3-chloro-5-methyl-4-hydroxyphenyl) -p-xylene, α , Α, α ', α'-tetrakis (3-bromo-5-methyl-4-hydroxyphenyl)
-P-xylene, α, α, α ′, α′-tetrakis (3
-Methoxy-5-methyl-4-hydroxyphenyl)-
p-xylene, α, α, α ′, α′-tetrakis (3-
t-butyl-5-methyl-4-hydroxyphenyl)-
p-xylene, α, α, α ′, α′-tetrakis (3-
Chloro-5-bromo-4-hydroxyphenyl) -p-
Xylene, α, α, α ′, α′-tetrakis (3-chloro-5-phenyl-4-hydroxyphenyl) -p-xylene, α, α, α ′, α′-tetrakis [(4-hydroxy-3 -Phenyl) phenyl] -p-xylene and the like.

The sulfoxide group-containing compound used in the present invention is not particularly limited as long as it has at least one sulfoxide group in the molecule and can form a molecular crystal with the above-mentioned tetrakisphenols. Alternatively, two or more kinds can be selected and used.

Specific examples of the sulfoxide group-containing compound used in the present invention include dimethyl sulfoxide, diethyl sulfoxide, di-n-propyl sulfoxide, di-iso-propyl sulfoxide, methyl ethyl sulfoxide, n-propyl methyl sulfoxide, i
alkyl sulfoxides such as so-propylmethylsulfoxide, n-propylethylsulfoxide, iso-propylethylsulfoxide, diphenylsulfoxide, methylphenylsulfoxide, ethylphenylsulfoxide, n-propylphenylsulfoxide, iso
-Propylphenylsulfoxide, arylsulfoxides such as p-tolylmethylsulfoxide, allylsulfoxides such as dipropenylsulfoxide, diarylalkylsulfoxides such as dibenzylsulfoxide,
Ethylene episulfoxide, thiolan-S-oxide,
Cyclic sulfoxides such as dithiane sulfoxide and thiophene-S-oxide; sulfinates such as methylmethane sulfinate, diphenyl sulfinate, di-p-tolylsulfinate and dibenzyl sulfinate;
Thiol sulfinates such as methyl methane thiol sulfinate, diphenyl thiol sulfinate, di-p-tolyl thiol sulfinate, dibenzyl thiol sulfinate, methyl pyridyl sulfoxide, ethyl pyridyl sulfoxide, phenyl pyridyl sulfoxide, benzyl Pyridylsulfoxides such as pyridylsulfoxide, thienylsulfoxides such as methylthienylsulfoxide, ethylthienylsulfoxide, phenylthienylsulfoxide and benzylthienylsulfoxide, methylfurylsulfoxide, ethylfurylsulfoxide, and furyls such as phenylfurylsulfoxide and benzylfurylsulfoxide; Sulfites such as trimethylene sulfite, amide sulfites, amide thiosulfate Aito acids, sulfinic amides,
Polysulfide oxides such as alkylthiosulfoxides, arylthiosulfoxides, arylalkylthiosulfoxides, alkylthioalkylsulfoxides, arylthioalkylsulfoxides, arylalkylthioalkylsulfoxides, benzopentathiepine monoxide and benzotrithiol monoxide; Can be mentioned.

As the reaction solvent used in the present invention, one or more selected from those commonly used as reaction solvents can be used. Among the reaction solvents, those which are liquid in a temperature range of 0 ° C. or more and 100 ° C. or less are preferably used, and particularly, 20 ° C. or more and 50 ° C.
Those which are liquid in the following temperature range are preferred.

Specific examples of the reaction solvent used in the present invention include water, methanol, ethanol, isopropanol, n-butanol, n-octanol, 2-
Alcohols such as ethylhexanol, allyl alcohol, propargyl alcohol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, cyclohexanediol, formaldehyde, acetaldehyde, n-butyraldehyde, propionaldehyde, benzaldehyde Aldehydes, such as acetone, methyl ethyl ketone, diethyl ketone, dibutyl ketone,
Ketones such as methyl isobutyl ketone, cyclohexanone and acetylacetone, nitriles such as acetonitrile, acrylonitrile, n-butyronitrile, ethers such as diethyl ether, dibutyl ether, tetrahydrofuran, dioxane, tetrahydropyran, methyl acetate, ethyl acetate, butyl acetate and the like Amides such as esters, sulfonamides, N-methylformamide, N, N-dimethylformamide, halogenated hydrocarbons such as dichloromethane, chloroform, tetrachloromethane, dichloroethylene and tetrachloroethylene, and fats such as n-hexane and cyclohexane Group hydrocarbons, phenols,
Phenols such as cresol and resorcinol, formic acid,
Acetic acid, carboxylic acids such as propionic acid and thiocarboxylic acids, sulfamic acids, thiocarbamic acids, thiosemicarbazides, urea and thioureas, isothioureas, sulfonylureas, thiophenols, thiols such as allyl mercaptan and n-butyl mercaptan , Sulfides, disulfides, sulfoxides such as dimethyl sulfoxide, sulfinates, sulfinamides, sulfites, sulfones, thiocyanic acid methyl ester, isothiocyanic acid methyl ester, etc., thiocyanic acids and isothiocyanic acids, amino acids, amides And urethane compounds, acid anhydrides, aromatic hydrocarbons such as benzene, toluene and xylene, alkenes, alkynes, isocyanates such as butyl isocyanate and cyclohexyl isocyanate. Sulphonates, methylene bis thiocyanate, thiocyanates such as methylene bis-isothiocyanate and isothiocyanates, nitro compounds,
Ammonia, methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, allylamine, hydroxylamine, ethanolamine, benzylamine, ethylenediamine, 1,2-propanediamine, 1,3-propanediamine, 1,4-
Butanediamine, 1,5-pentanediamine, 1,6-
Hexanediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, dipropylenediamine, N, N-dimethylethylenediamine, N,
Acyclic aliphatic amines such as N'-dimethylethylenediamine, cyclohexylamine, pyrrolidines, azetidines, piperidines, piperazines, cyclic aliphatic amines such as pyrrolines, aniline, N-methylaniline,
Aromatic amines such as N, N-dimethylaniline, polyamines, imidazole, pyrrole, pyridine, picoline, furan, furfuryl alcohol, tetrahydrofurfuryl alcohol, furfurylamine, pyran, coumarin, benzofuran, xanthene, benzodioxane, oxazole , Isoxazole, benzoxazole,
Benzoisoxazole, 5-methyloxazolidine, 4
-(2-nitrobutyl) morpholine, 4,4 '-(2-
Ethyl-2-nitrotrimethylene) heterocyclic compounds such as dimorpholine, thiophene, and thiazole.

The molecular crystal of the present invention is obtained by reacting the above-mentioned tetrakisphenols and the above-mentioned sulfoxide group-containing compound with stirring in the presence of a reaction solvent at room temperature to 100 ° C. for several minutes to tens of hours. By selecting a reaction solvent, molecular crystals can be produced in higher yield. When the sulfoxide group-containing compound is a liquid, it can be used as a reaction solvent to generate molecular crystals.

In the method for producing a molecular crystal according to the present invention,
The above-mentioned method of reacting tetrakisphenols with one type of sulfoxide group-containing compound, and the selective production method of reacting tetrakisphenols with two or more types of sulfoxide-group-containing compounds. In the latter method for selectively producing molecular crystals, tetrakisphenols and two or more sulfoxide group-containing compounds are selectively used in reaction solvents having different proton-donating properties with respect to the sulfoxide group-containing compounds, whereby two or more sulfoxide group-containing compounds are used. It is possible to selectively generate a molecular crystal having a target specific sulfoxide group-containing compound among the compounds as a component compound. That is, by selecting the reaction solvent, it becomes possible to control the aggregation form of the molecular crystal constituents, and to obtain a molecular crystal having a specific sulfoxide group-containing compound of interest as a component compound with high selectivity and high yield. Can be generated.

Here, the reaction solvents having different proton donating properties refer to reaction solvents having different degrees of action as proton donors, and include those which do not act as proton donors.

In the method for selectively producing a molecular crystal of the present invention,
Which sulfoxide group-containing compound can be a component compound constituting a molecular crystal is governed by the intermolecular interaction between each component compound and the reaction solvent. The molecular crystal of the present invention is a polymolecular crystal in which a tetrakisphenol and a sulfoxide group-containing compound are bonded by a relatively weak interaction other than a covalent bond represented by a hydrogen bond, van der Waals force, or the like. By using different reaction solvents with different proton donating properties for the containing compound,
Interactions between these molecules can be controlled, thereby expressing the selectivity of the molecular crystal composition.

For example, in a combination of a reaction solvent acting as a proton donor with respect to a sulfoxide group-containing compound and a sulfoxide group-containing compound having stronger proton acceptability, the sulfoxide group-containing compound is strongly solvated by the reaction solvent. When a sulfoxide group-containing compound having low proton acceptability and being less likely to be solvated coexists in the same system, a molecular crystal having the sulfoxide group-containing compound as a component compound is selectively formed. On the other hand, by using a reaction solvent that does not act as a proton donor for the sulfoxide group-containing compound, the sulfoxide group-containing compound having higher proton acceptability is selectively incorporated into the molecular crystal by strong interaction with tetrakisphenols. It is.

Specifically, a mixture of two sulfoxide group-containing compounds having different proton-accepting properties, such as dimethyl sulfoxide and diphenyl sulfoxide, and 1,1,2,2-tetrakis (4-tetrakisphenol) In a reaction system comprising (hydroxyphenyl) ethane, a reaction solvent which acts as a proton donor for a sulfoxide group-containing compound such as methanol is used, so that a molecule comprising diphenyl sulfoxide and tetrakisphenols having lower proton acceptability is used. Crystals can be selectively obtained. On the other hand, by using a reaction solvent that does not act as a proton donor for a sulfoxide group-containing compound such as ethyl acetate, a molecular crystal composed of dimethyl sulfoxide and tetrakisphenols having higher proton acceptability can be selectively obtained. . As described above, when the selective production method of the molecular crystal of the present invention is used, it is possible to selectively separate a specific sulfoxide group-containing compound, which has conventionally been difficult to select, by selecting a reaction solvent.

The fact that the substance obtained by the production method of the present invention is indeed a molecular crystal can be confirmed by thermal analysis (TG-DTA),
Infrared absorption spectrum (IR), X-ray diffraction pattern, ¹³ C
-It can be confirmed by a solid NMR spectrum or the like. The composition of the molecular crystal can be confirmed by thermal analysis, ¹ H-NMR spectrum, high performance liquid chromatography (HPLC), elemental analysis and the like. The molecular crystal of the present invention exists stably alone, and easily dissociates into each component compound when heated under normal pressure or reduced pressure.

Now, the present invention will be described in further detail with reference to Examples. However, the present invention is not limited at all by these examples. Examples (Production of Molecular Crystals) As tetrakisphenols, 1,1,2,2-tetrakis (4-hydroxyphenyl) ethane (hereinafter referred to as “TE
P "), and reacted with a sulfoxide group-containing compound shown in Table 1 in the presence of a reaction solvent also shown in Table 1, to produce a molecular crystal as follows. One or two or more sulfoxide group-containing compounds are dissolved or suspended in the reaction solvent, and TEP is added thereto in an amount of 0.1 to equimolar to the sulfoxide group-containing compound.
The mixture was stirred or left at 0 ° C. for 1 to 24 hours to precipitate crystals. After these precipitates were separated by filtration, they were vacuum-dried at room temperature to 80 ° C. to obtain molecular crystals. Table 1 shows the results.

As can be seen from Samples 12 to 19 in Table 1, by selectively using a reaction solvent having a different proton-donating property for tetrakisphenols, it is possible to select a sulfoxide group-containing compound as a component compound of a molecular crystal. I was assured. The sample 1 obtained in the example was used.
-19 all had their composition determined by < ¹ > H-NMR spectrum. Samples 1 to 11 were analyzed by thermal analysis (TG-
DTA), infrared absorption spectrum (IR), and ¹³ C-solid NMR spectrum, Samples ^{12 to 19} were confirmed to be molecular crystals by infrared absorption spectrum (IR) and ¹³ C-solid NMR spectrum. Infrared absorption spectra (IR) of Samples 1 to 19 are shown in FIGS.

The meanings of the abbreviations in Table 1 are as follows. (Tetrakisphenols) TEP: 1,1,2,2-tetrakis (4-hydroxyphenyl) ethane (sulfoxide group-containing compound) DMSO: dimethylsulfoxide DESO: diethylsulfoxide DNPSO: di-n-propylsulfoxide DIPSO: di-iso -Propyl sulfoxide DPSO: diphenyl sulfoxide MESO: methyl ethyl sulfoxide MPSO: methyl phenyl sulfoxide EPSO: ethyl phenyl sulfoxide NPPSO: n-propyl phenyl sulfoxide IPPSO: iso-propyl phenyl sulfoxide FAMSO: methyl (methylthio) methyl sulfoxide

[0026]

[Table 1]

[0027]

According to the present invention, by using tetrakisphenols, it is possible to provide an easy-to-handle novel molecular crystal which is complexed with an industrially useful sulfoxide group-containing compound. The novel molecular crystal and its manufacturing method have the following features, and therefore have a very significant industrial significance. 1) By using tetrakisphenols, various sulfoxide group-containing compounds that are industrially useful can be obtained as stable molecular crystals. 2) The molecular crystal constituents and the aggregation form thereof are controlled by the difference in the reaction solvent characteristics, so that the molecular crystal, which has conventionally been difficult to produce, can be produced stably with the intended composition. 3) The generated molecular crystal can be easily separated into each component compound when heated under normal pressure or reduced pressure. 4) Since the generated molecular crystals are solids at room temperature, powders,
Suspensions, granules, tablets and the like can be formulated, and handling is extremely easy.

[Brief description of the drawings]

FIG. 1 is a diagram showing an infrared absorption spectrum (KBr method) of a molecular crystal of Sample 1 in Table 1.

FIG. 2 is a diagram showing an infrared absorption spectrum (KBr method) of a molecular crystal of Sample 2 in Table 1.

FIG. 3 is a view showing an infrared absorption spectrum (KBr method) of a molecular crystal of Sample 3 in Table 1.

FIG. 4 is a view showing an infrared absorption spectrum (KBr method) of a molecular crystal of Sample 4 in Table 1.

5 is a diagram showing an infrared absorption spectrum (KBr method) of a molecular crystal of Sample 5 in Table 1. FIG.

6 is a diagram showing an infrared absorption spectrum (KBr method) of a molecular crystal of Sample 6 in Table 1. FIG.

FIG. 7 is a diagram showing an infrared absorption spectrum (KBr method) of a molecular crystal of Sample 7 in Table 1.

8 is a view showing an infrared absorption spectrum (KBr method) of a molecular crystal of Sample 8 in Table 1. FIG.

9 is a diagram showing an infrared absorption spectrum (KBr method) of a molecular crystal of Sample 9 in Table 1. FIG.

10 is a diagram showing an infrared absorption spectrum (KBr method) of a molecular crystal of Sample 10 in Table 1. FIG.

11 is a diagram showing an infrared absorption spectrum (KBr method) of a molecular crystal of Sample 11 in Table 1. FIG.

12 is a diagram showing an infrared absorption spectrum (KBr method) of a molecular crystal of Sample 12 in Table 1. FIG.

13 is a diagram showing an infrared absorption spectrum (KBr method) of a molecular crystal of Sample 13 in Table 1. FIG.

14 is a diagram showing an infrared absorption spectrum (KBr method) of a molecular crystal of Sample 14 in Table 1. FIG.

15 shows an infrared absorption spectrum (KBr method) of a molecular crystal of Sample 15 in Table 1. FIG.

16 is a diagram showing an infrared absorption spectrum (KBr method) of a molecular crystal of Sample 16 in Table 1. FIG.

17 shows an infrared absorption spectrum (KBr method) of a molecular crystal of Sample 17 in Table 1. FIG.

18 is a diagram showing an infrared absorption spectrum (KBr method) of a molecular crystal of Sample 18 in Table 1. FIG.

19 is a diagram showing an infrared absorption spectrum (KBr method) of a molecular crystal of Sample 19 in Table 1. FIG.

Claims (3)

[Claims] 1. A molecular crystal comprising a tetrakisphenol represented by the general formula [1] and a sulfoxide group-containing compound. Embedded image (Wherein X represents (CH ₂ ) _n or a phenyl group;
Is 0, 1, 2, or 3, and R ¹ and R ² each represent a hydrogen atom, a lower alkyl group, an optionally substituted phenyl group, a halogen atom, or a lower alkoxy group. ) 2. A tetrakisphenol represented by the general formula [1] characterized by reacting a tetrakisphenol represented by the general formula [1] with a sulfoxide group-containing compound in the presence of a reaction solvent. A method for producing a molecular crystal comprising: and a sulfoxide group-containing compound. 3. A method for producing a molecular crystal by reacting a tetrakisphenol represented by the general formula [1] with two or more kinds of sulfoxide group-containing compounds in the presence of a reaction solvent. By using different reaction solvents having different proton donating properties, 2
A tetrakisphenol represented by the general formula [1] and a sulfoxide group-containing compound represented by the general formula [1], wherein a molecular crystal having a specific sulfoxide group-containing compound as a component compound among the at least one sulfoxide group-containing compound is selectively formed. A method for producing a molecular crystal comprising a compound.