JP2000095752A - Molecular compound containing phenylsulfone derivative as component compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new compound having a structure cross-linked with a specific group and useful as the component compound of a molecular compound exhibiting excellent performances on the selective separation, chemical stabilization, non-volatization, sustained release, pulverization, etc., of useful substances. SOLUTION: A compound of the formula [Y is a 1-12C hydrocarbon group or the like; R1-R4 are each H, a halogen, a 1-8C alkyl or the like; R5, R6 are each a 1-8C alkyl or the like; (m) is 0-2, preferably 2; (n), (p), (q), (r) are each 0-4]. For example, 2,2'-bis[4-(4-isopropoxyphenylsulfonyl)phenyloxy]diethyl either. The compound of formula is obtained, for example, by reacting dihydroxydiphenylsulfone, etc., with an alkyl halide, etc., in the presence of a base in a proper solvent under a heated condition and subsequently reacting the obtained corresponding monoalkyloxy compound with an alkyl dihalide, etc., in the presence of a base in a proper solvent under a heated condition.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a novel molecular compound, and more particularly to a molecular compound comprising a phenylsulfone derivative having a specific structure as a component compound.

[0002]

2. Description of the Related Art A molecular compound is a compound in which two or more kinds of 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. In recent years, since it has the property of dissociating into each component compound, selective separation of useful substances,
Applications in technical fields such as chemical stabilization, non-volatilization, sustained release, and powdering are expected.

An example of a specific molecular compound is an inclusion compound. For example, JP-A-61-53201 discloses 1,1,6,6-tetraphenyl-2,4-hexadiyne-1, 6-diol or 1,1-di (2,4-
Dimethylphenyl) -2-propyn-1-ol, disclosed in JP-A-62-2701, is 1,1'-bis-2-yl.
Naphthol and 5-chloro-2-methyl-4-
Inclusion compounds with isothiazolin-3-one and the like are described. JP-A-6-166646 discloses clathrate compounds of tetrakisphenols with various organic compounds. However, in the prior art, selective separation,
No molecular compound having satisfactory performance in chemical stabilization, non-volatilization, sustained release, powdering, etc. has been found yet.

[0004]

An object of the present invention is to provide a phenylsulfone derivative which exhibits excellent performance in the technical fields such as selective separation of useful substances, chemical stabilization, non-volatization, sustained release, and powdering. It is to provide a novel molecular compound as a component compound.

[0005]

Means for Solving the Problems The inventors of the present invention have conducted intensive studies to achieve the above object, and as a result, a molecular compound containing a phenylsulfone derivative cross-linked with a specific group as a component compound has been obtained by selective separation of useful substances. The inventors have found that they exhibit excellent performance in technical fields such as chemical stabilization, non-volatization, sustained release, and powdering, and have completed the present invention.

That is, the present invention provides a compound represented by the general formula (I)

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In the formula, Y is a saturated or unsaturated hydrocarbon group having 1 to 12 carbon atoms, which may be linear or branched, or a 1 to 8 carbon atom having an ether bond or a thioether bond. Hydrocarbon groups,

[0008]

Embedded image (R represents a methylene group or an ethylene group), or

[0009]

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(T represents a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms), and R ¹ , R ² , R ³ and R ⁴ may be the same or different from each other and include a hydrogen atom, a halogen atom, C1 ~ C
8 represents an alkyl group and a C2-C8 alkenyl group;
⁵ and R ⁶ may be the same or different and may have a linear or branched C1-C8 alkyl group, a linear or branched C2-C8 alkenyl group,
C1-C4 alkyl group or C2-C4 alkenyl group or C1-C4 alkoxy group or hydroxyl group or cyclohexyl group optionally having a halogen atom, C1-C4 alkyl group or C2-C4 alkenyl group or C1-C4 C4 alkoxy group, hydroxyl group or cyclopentyl group optionally having a halogen atom, C1 to C4 alkyl group or C2 to C4 alkenyl group, or C1 to C4 alkoxy group or benzyl optionally having a hydroxyl group or halogen atom A C1-C4 alkyl group or a C2-C4 alkenyl group or a C1-C4 alkoxy group or a phenethyl group which may have a hydroxyl group or a halogen atom, a C1-C4 alkyl group or a C2-C4 alkenyl group or C1 4 may have an alkoxy group or a hydroxyl group or a halogen atom α- methylbenzyl group, or a C1~C4 alkyl or C2~ of
A C4 alkenyl group or a C1 to C4 alkoxy group, a hydroxyl group or a naphthylmethyl group which may have a halogen atom, m represents any of 0, 1, 2; n, p, q or r represents Represents 0 or an integer of 1 to 4, provided that when n, p, q or r is 2 or more, R ¹ , R ² , R ³ or R ⁴ may be the same or different, A phenylsulfone derivative represented by the general formula (I).

The present invention also provides a molecular compound containing the phenylsulfone derivative as a component compound, an antibacterial agent, an antifungal agent, an insecticide, which reacts the phenylsulfone derivative with the phenylsulfone derivative to form a molecular compound. Pest repellents, fragrances, deodorizing / deodorizing agents, antifouling agents, curing agents and curing accelerators for paints, resins, adhesives, natural essential oils, antioxidants, vulcanization accelerators or molecules containing organic solvents as component compounds The present invention relates to a compound and a molecular compound in which the molecular compound is an inclusion compound.

[0012]

BEST MODE FOR CARRYING OUT THE INVENTION The molecular compound in the present invention is
A compound in which two or more component compounds of a compound that can exist stably alone are bound by a relatively weak interaction other than a covalent bond represented by a hydrogen bond, van der Waals force, etc. Compounds, adducts,
Inclusion compounds and the like are included.

In the phenylsulfone derivative represented by the general formula (I) of the present invention, Y represents a saturated or unsaturated C 1 -C 1, which may be linear or branched.
12 hydrocarbon groups, a hydrocarbon group having 1 to 8 carbon atoms having an ether bond or a thioether bond,

[0014]

Embedded image (R represents a methylene group or an ethylene group), or

[0015]

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(T is a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms). Specific examples include methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, decamethylene, undecamethylene, and dodecamethylene. , Methylmethylene group, dimethylmethylene group, methylethylene group, methyleneethylene group, ethylethylene group, 1,2-dimethylethylene group, 1-methyltrimethylene group, 1-methyltetramethylene group, 1,3-dimethyltrimethylene Group, 1-ethyl-4-methyltetramethylene group, vinylene group, propenylene group, 2-butenylene group, ethynylene group, 2-butynylene group, 1-vinylethylene group, ethyleneoxyethylene group, tetramethyleneoxytetramethylene group, Ethyleneoxyethyleneoxyethylene Group, ethyleneoxymethyleneoxyethylene group, ethylenethioethylene group, tetramethylenethiotetramethylene group, ethylenethioethylenethioethylene group, ethylenethiomethylenethioethylene group, 1,3-dioxane-5,5-bismethylene group, p- A xylene-α, α′-diyl group, an m-xylene-α, α′-diyl group, an o-xylene-α, α′-diyl group, a 2-hydroxypropylene group, a 2-hydroxy-2-methylpropylene group, Examples thereof include a 2-hydroxy-2-ethylpropylene group, a 2-hydroxy-2-propylpropylene group, and a 2-hydroxy-2-butylpropylene group.

In the general formula (I), R ¹ , R ² , R ³ and R
⁴ may be the same or different from each other, and represent a hydrogen atom, a halogen atom, a C1 to C8 alkyl group, or a C2 to C8 alkenyl group, and specific examples include a methyl group,
Ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert
-Pentyl group, n-hexyl group, isohexyl group, 1-
Methylpentyl group, 2-methylpentyl group, vinyl group,
Allyl group, isopropenyl group, 1-propenyl group, 2-
Butenyl, 3-butenyl, 1,3-butanedienyl, 2-methyl-2-propenyl and the like.

In the general formula (I), R ⁵ and R ⁶ may be the same or different, and may have a linear or branched C1-C8 alkyl group, a linear or branched alkyl group. C2 to C8 alkenyl groups, C1 to C4 alkyl groups or C2 to C4 alkenyl groups or C1 to C4
4 alkoxy group, hydroxyl group, or cyclohexyl group which may have a halogen atom, C1-C4 alkyl group, C2-C4 alkenyl group, or C1-
A C4 alkoxy group, a hydroxyl group or a cyclopentyl group which may have a halogen atom, a C1 to C4 alkyl group, a C2 to C4 alkenyl group or C1.
To C4 alkoxy group, hydroxyl group or benzyl group optionally having a halogen atom, C1 to C4 alkyl group or C2 to C4 alkenyl group or C1 to C4
A phenethyl group which may have an alkoxy group, a hydroxyl group or a halogen atom, a C1 to C4 alkyl group, a C2 to C4 alkenyl group or a C1 to C4
Α-methylbenzyl group which may have an alkoxy group or a hydroxyl group or a halogen atom, or a C1 to C4 alkyl group or a C2 to C4 alkenyl group or a C1 to C4 alkoxy group or a hydroxyl group or a halogen atom. Represents a naphthylmethyl group.

Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl,
Isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, neopentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, n-
Heptyl group, isoheptyl group, sec-heptyl group, n
-Octyl group, isooctyl group, sec-octyl group,
Vinyl group, allyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1,3-butanedienyl group, 1-pentenyl group, 2
-Pentenyl group, 3-pentenyl group, 4-pentenyl group, hexynyl group, hexidinyl group, heptynyl group, heptidinyl group, octynyl group, octidinyl group, cyclopentyl group, methylcyclopentyl group, dimethylcyclopentyl group, cyclohexyl group, methylcyclohexyl group, Dimethylcyclohexyl, trimethylcyclohexyl, tetramethylcyclohexyl, pentamethylcyclohexyl, cycloheptyl, methylcycloheptyl, benzyl, o- or m- or p-tolylmethyl, 2,3- or 2,4- Or 2,5- or 2,6
-Or 3,4- or 3,5- or 4,5-xylylmethyl group, mesitylmethyl group, o- or m- or p-cumenylmethyl group, phenethyl group, α-methylbenzyl group, 1
-Naphthylmethyl group, 2-naphthylmethyl group and the like.

Among the compounds represented by the general formula (I), a phenylsulfone derivative represented by the general formula (II) is preferable.

[0021]

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Further, a compound represented by the general formula (III) is particularly preferred.

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Further, from the viewpoint of synthesis, the compound represented by the general formula (IV) is advantageous.

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The phenylsulfone derivative used in the present invention is not particularly limited as long as it is a compound represented by the general formula (I). Specific examples include bis [4- (4-isopropoxyphenylsulfonyl) phenyl Oxy] methane, 1,2-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxy] ethane, 1,3-bis [4
-(4-n-propoxyphenylsulfonyl) phenyloxy] propane, 1,4-bis [4- (4-n-butoxyphenylsulfonyl) phenyloxy] butane, 1,
5-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxy] pentane, 1,6-bis [4- (4
-Sec-butoxyphenylsulfonyl) phenyloxy] hexane, 1,7-bis [4- (4-sec-pentyloxyphenylsulfonyl) phenyloxy] heptane, 1,8-bis [4- (4-n-pentyloxy) Phenylsulfonyl) phenyloxy] octane, 1,9-
Bis [4- (4-p-tolylmethyloxyphenylsulfonyl) phenyloxy] nonane, 1,10-bis [4-
(4-α-methylbenzyloxyphenylsulfonyl)
Phenyloxy] decane, 1,11-bis [4- {4-
(1-naphthylmethyloxy) phenylsulfonyl {phenyloxy] undecane, 1,12-bis [4- {4-
(2-Naphthylmethyloxy) phenylsulfonyl {phenyloxy] dodecane can be mentioned.

Similarly, 1,1-bis [4- (4-n
-Hexyloxyphenylsulfonyl) phenyloxy] ethane, 2,2-bis [4- (4-cyclohexyloxyphenylsulfonyl) phenyloxy] propane,
1,2-bis [4- (4-isopropoxyphenylsulfonyl) phenyloxy] propane, 2,3-bis [4-
(4-benzyloxyphenylsulfonyl) phenyloxy] propene, 1,2-bis [4- (4-isohexyloxyphenylsulfonyl) phenyloxy] butane,
2,3-bis [4- (4-isobutoxyphenylsulfonyl) phenyloxy] butane, 1,3-bis [4- (4
-Isopentyloxyphenylsulfonyl) phenyloxy] butane, 1,4-bis [4- (4-vinyloxyphenylsulfonyl) phenyloxy] pentane, 2,4
-Bis [4- (4-allyloxyphenylsulfonyl)
Phenyloxy] pentane and 2,5-bis [4- (4-methoxyphenylsulfonyl) phenyloxy] heptane.

Similarly, 1,2-bis [4- (4-isopropoxyphenylsulfonyl) phenyloxy] ethylene, 1,3-bis [4- (4-ethoxyphenylsulfonyl) phenyloxy] propene, 4-bis [4
-(4-n-propoxyphenylsulfonyl) phenyloxy] -2-butene, 1,2-bis [4- (4-sec
-Butoxyphenylsulfonyl) phenyloxy] acetylene, 1,4-bis [4- (4-tert-butoxyphenylsulfonyl) phenyloxy] -2-butyne,
3,4-bis [4- (4-isopropenyloxyphenylsulfonyl) phenyloxy] -1-butene can be mentioned.

Similarly, 2,2'-bis [4- (4-
Isopropoxyphenylsulfonyl) phenyloxy]
Diethyl ether, 2,2'-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxy] diethyl ether, 2,2'-bis [4- (4-n-propoxyphenylsulfonyl) phenyloxy] diethyl ether, 2,2'-bis [4- (4-sec-butoxyphenylsulfonyl) phenyloxy] diethyl ether, 2,2'-bis [4- (4-sec-pentyloxyphenylsulfonyl) phenyloxy] diethyl ether, 2,2'-bis [4- (4-p-tolylmethyloxyphenylsulfonyl) phenyloxy] diethyl ether, 2,2'-bis [4- (4-α-methylbenzyloxyphenylsulfonyl) phenyloxy] diethyl ether , 2,2'-bis [4- {4- (1-naphthylmethyloxy) phenylsulfonyl} Eniruokishi] diethyl ether, 2- [4- (4-isopropoxyphenyl) phenyl oxy] -2' [4
-(4-benzyloxyphenylsulfonyl) phenyloxy] diethyl ether, 4,4'-bis [4- (4-
Isopropoxyphenylsulfonyl) phenyloxy]
Dibutyl ether can be mentioned.

Similarly, 1,2-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxyethyloxy] ethane, bis [4- (4-n-propoxyphenylsulfonyl) phenyloxyethyloxy] methane, 2,2'-bis [4- (4-sec-butoxyphenylsulfonyl) phenyloxy] diethylthioether, 4,4'-bis [4- (4-sec-pentyloxyphenylsulfonyl) phenyloxy] dibutylthioether, , 2-bis [4- (4-hydroxyphenylsulfonyl) phenyloxyethylthio] ethane, bis [4- (4-hydroxyphenylsulfonyl) phenyloxyethylthio] methane, 1,4-bis [4- (4-
Isopropoxyphenylsulfonyl) phenyloxymethyl] benzene, 1,3-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxymethyl] benzene, 1,2-bis [4- (4-α-methylbenzyloxyphenyl) Sulfonyl) phenyloxymethyl] benzene.

Similarly, 1,3-bis [4- (4-isopropoxyphenylsulfonyl) phenyloxy]-
2-hydroxypropane, 1,3-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxy]-
2-hydroxypropane, 1,3-bis [4- (4-n
-Propoxyphenylsulfonyl) phenyloxy]-
2-hydroxypropane, 1,3-bis [4- (4-s
ec-butoxyphenylsulfonyl) phenyloxy]
-2-hydroxypropane, 1,3-bis [4- (4-
sec-pentyloxyphenylsulfonyl) phenyloxy] -2-hydroxypropane, 1,3-bis [4-
(4-p-toluyloxyphenylsulfonyl) phenyloxy] -2-hydroxypropane, 1,3-bis [4
-(4-α-methylbenzyloxyphenylsulfonyl) phenyloxy] -2-hydroxypropane, 1,
3-bis [4- (4-2-naphthylmethyloxyphenylsulfonyl) phenyloxy] -2-hydroxypropane, 1- [4- (4-isopropoxyphenylsulfonyl) phenyloxy] -3- [4- (4 -Benzyloxyphenylsulfonyl) phenyloxy] -2-hydroxypropane, 1,3-bis [4- (4-isopropoxyphenylsulfonyl) phenyloxy] -2-methyl-2-hydroxypropane, 1,3-bis [ 4- (4-
Benzyloxyphenylsulfonyl) phenyloxy]
-2-ethyl-2-hydroxypropane, 1,3-bis
[4- (4-n-propoxyphenylsulfonyl) phenyloxy] -2-propyl-2-hydroxypropane, 1,3-bis [4- (4-sec-butoxyphenylsulfonyl) phenyloxy] -2-butyl- 2-hydroxypropane can be mentioned.

Similarly, bis [4- (2-sec-pentyloxyphenylsulfonyl) phenyloxy] methane, 1,2-bis [4- (2-isopropoxyphenylsulfonyl) phenyloxy] ethane, 1,3 -Screw
[4- (2-benzyloxyphenylsulfonyl) phenyloxy] propane, 1,4-bis [4- (2-p-toluyloxyphenylsulfonyl) phenyloxy] butane, 1,5-bis [4- (2- α-methylbenzyloxyphenylsulfonyl) phenyloxy] pentane,
1,6-bis [4- (2-neopentyloxyphenylsulfonyl) phenyloxy] hexane, 1,3-bis
[4- (2-2-naphthylmethyloxyphenylsulfonyl) phenyloxy] butane, 1,4-bis [4- (2
-Isohexyloxyphenylsulfonyl) phenyloxy] -2-butene and 3,4-bis [4- (2-hydroxyphenylsulfonyl) phenyloxy] -1-butene.

Similarly, 2,2'-bis [4- (2-
Hydroxyphenylsulfonyl) phenyloxy] diethyl ether, 2,2'-bis [4- (2-isopropoxyphenylsulfonyl) phenyloxy] diethylthioether, 1,4-bis [4- (2-benzyloxyphenylsulfonyl) phenyl Oxymethyl] benzene, 1,3-bis [4- (2-n-propoxyphenylsulfonyl) phenyloxymethyl] benzene, 1,2
-Bis [4- (2-sec-pentyloxyphenylsulfonyl) phenyloxymethyl] benzene, 1,3-
Bis [4- (2-isopropoxyphenylsulfonyl)
Phenyloxy] -2-hydroxypropane, 1,3-
Bis [4- (2-benzyloxyphenylsulfonyl)
[Phenyloxy] -2-methyl-2-hydroxypropane.

Similarly, bis [2- (4-sec-butoxyphenylsulfonyl) phenyloxy] methane,
1,2-bis [2- (4-p-toluyloxyphenylsulfonyl) phenyloxy] ethane, 1,3-bis [2
-(4-α-methylbenzyloxyphenylsulfonyl) phenyloxy] propane, 1,4-bis [2- {4
-(2-naphthylmethyloxy) phenylsulfonyl}
Phenyloxy] butane, 1,5-bis [2- {4- (2
-Butenyloxy) phenylsulfonyl {phenyloxy] pentane, 1,6-bis [2- (4-isopropoxyphenylsulfonyl) phenyloxy] hexane,
3-bis [2- (4-benzyloxyphenylsulfonyl) phenyloxy] butane, 1,4-bis [2- (4-
n-propoxyphenylsulfonyl) phenyloxy]
-2-butene, 3,4-bis [2- (4-sec-pentyloxyphenylsulfonyl) phenyloxy] -1
-Butene.

Similarly, 2,2'-bis [2- {4-
(1-naphthylmethyloxy) phenylsulfonyl {phenyloxy] diethyl ether, 2,2'-bis [2-
{4- (3-pentenyloxy) phenylsulfonyl}
Phenyloxy] diethylthioether, 1,4-bis
[2- (4-o-toluylmethyloxyphenylsulfonyl) phenyloxymethyl] benzene, 1,3-bis
[2- (4-m-toluylmethyloxyphenylsulfonyl) phenyloxymethyl] benzene, 1,2-bis
[2- (4-α-methylbenzyloxyphenylsulfonyl) phenyloxymethyl] benzene, 1,3-bis
[2- (4-p-cumenylmethyloxyphenylsulfonyl) phenyloxy] -2-hydroxypropane,
1,3-bis [2- (4-isopropoxyphenylsulfonyl) phenyloxy] -2-methyl-2-hydroxypropane can be mentioned.

Similarly, 2- (4-benzyloxyphenylsulfonyl) phenyloxy-4- (2-sec
-Butoxyphenylsulfonylphenyloxy) methane, 1- [2- (4-sec-pentyloxyphenylsulfonyl) phenyloxy] -2- [4- (2-p-toluyloxyphenylsulfonyl) phenyloxy] ethane, 1- [2- (4-benzyloxyphenylsulfonyl) phenyloxy] -3- [4- {2- (2-naphthylmethyloxy) phenylsulfonyl} phenyloxy] propane, 1- [2- (4-iso-propenyloxy) Phenylsulfonyl) phenyloxy] -4- [4-
(2-hydroxyphenylsulfonyl) phenyloxy] butane, 1- [2- (4-isopropoxyphenylsulfonyl) phenyloxy] -5- [4- (2-isopropoxyphenylsulfonyl) phenyloxy] pentane, 1- [ 2- (4-benzyloxyphenylsulfonyl) phenyloxy] -6- [4- (2-isopropoxyphenylsulfonyl) phenyloxy] hexane, 1-
[2- (4-benzyloxyphenylsulfonyl) phenyloxy] -3- [4- (2-n-propoxyphenylsulfonyl) phenyloxy] butane, 1- [2- (4-
sec-butoxyphenylsulfonyl) phenyloxy] -4- [4- (2-sec-pentyloxyphenylsulfonyl) phenyloxy] -2-butene, 3- [2-
(4-p-toluyloxyphenylsulfonyl) phenyloxy] -4- [4- (2-α-methylbenzyloxyphenylsulfonyl) phenyloxy] -1-butene.

Similarly, 2- [2- {4- (1-naphthylmethyloxy) phenylsulfonyl} phenyloxy] -2 '-[4- {2- (2-naphthylmethyloxy)
Phenylsulfonyl @ phenyloxy] diethyl ether, 2- [2- (4-hydroxyphenylsulfonyl)
Phenyloxy] -2 '-[4- (2-hydroxyphenylsulfonyl) phenyloxy] diethylthioether, 1- [2- (4-hydroxyphenylsulfonyl)
Phenyloxymethyl] -4- [4- (2-isopropoxyphenylsulfonyl) phenyloxy] benzene, 1
-[2- (4-benzyloxyphenylsulfonyl) phenyloxymethyl] -3- [4- (2-n-propoxyphenylsulfonyl) phenyloxy] benzene, 1-
[2- (4-sec-butoxyphenylsulfonyl) phenyloxymethyl] -2- [4- (2-hydroxyphenylsulfonyl) phenyloxy] benzene, 1- [2-
(4-cyclohexyloxyphenylsulfonyl) phenyloxy] -3- [4- (2-cyclopentyloxyphenylsulfonyl) phenyloxy] -2-hydroxypropane, 1- [2- {4- (2,5-xylylmethyl) Oxy) phenylsulfonyl {phenyloxy] -3-
[4- (2-iso-butoxyphenylsulfonyl) phenyloxy] -2-methyl-2-hydroxypropane.

Among the compounds represented by formula (I), selective separation of useful substances, chemical stabilization, non-volatization, sustained release,
From the viewpoint of performance such as powdering, particularly, 2,2'-bis [4-
(4-isopropoxyphenylsulfonyl) phenyloxy] diethyl ether, 2,2'-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxy] diethyl ether, 2,2'-bis [4- (4-sec −
Butoxyphenylsulfonyl) phenyloxy] diethyl ether, 2,2'-bis [4- (4-sec-pentyloxyphenylsulfonyl) phenyloxy] diethyl ether, 2,2'-bis [4- (4-p-toluyl) Oxyphenylsulfonyl) phenyloxy] diethyl ether, 2,2′-bis [4- (4-α-methylbenzyloxyphenylsulfonyl) phenyloxy] diethyl ether, 2,2′-bis [4- {4- (1 -Naphthylmethyloxy) phenylsulfonyl {phenyloxy] diethyl ether, 2- [4- (4-isopropoxyphenylsulfonyl) phenyloxy] -2'-
[4- (4-benzyloxyphenylsulfonyl) phenyloxy] diethyl ether, 1,3-bis [4- (4
-Iso-propoxyphenylsulfonyl) phenyloxy] -2-hydroxypropane, 1,3-bis [4-
(4-benzyloxyphenylsulfonyl) phenyloxy] -2-hydroxypropane, 3-bis [4- (4-
sec-butoxyphenylsulfonyl) phenyloxy] -2-hydroxypropane, 1,3-bis [4- (4
-Sec-pentyloxyphenylsulfonyl) phenyloxy] -2-hydroxypropane, 1,3-bis [4
-(4-p-toluyloxyphenylsulfonyl) phenyloxy] -2-hydroxypropane, 1,3-bis
[4- (4-α-methylbenzyloxyphenylsulfonyl) phenyloxy] -2-hydroxypropane,
1,3-bis [4- {4- (2-naphthylmethyloxy) phenylsulfonyl} phenyloxy] -2-hydroxypropane, 1- [4- (4-isopropoxyphenylsulfonyl) phenyloxy] -3- [ 4- (4-benzyloxyphenylsulfonyl) phenyloxy]-
2-hydroxypropane is preferred.

The method for producing the phenylsulfone derivative represented by the general formula (I) is not particularly limited. However, dihydroxydiphenylsulfone or a derivative thereof, dihydroxydiphenylsulfoxide or a derivative thereof, dihydroxydiphenylthioether or a derivative thereof are used as starting materials. Can be easily manufactured by any one of the methods described above.

For example, in the presence of an inorganic base such as sodium hydroxide, potassium hydroxide, calcium hydroxide, calcium carbonate, potassium carbonate, sodium hydride, or an organic base such as triethylamine or pyridine, a non-aqueous solution such as toluene. Organic solvents, water-soluble organic solvents such as dimethylformamide and methanol, a mixed solvent of water and a water-insoluble organic solvent, a mixed solvent of water and a water-soluble organic solvent, or in an aqueous solvent, such as dihydroxydiphenyl sulfone or a derivative thereof. , Dihydroxydiphenylsulfoxide or a derivative thereof, dihydroxydiphenylthioether or a derivative thereof are reacted with an alkyl halide, an alkenyl halide, an aralkyl halide or the like under heating conditions to obtain a corresponding monoalkyloxy, monoalkenyloxy, or monoaralkyl. Producing carboxymethyl derivatives. Then, in the presence of an inorganic base such as sodium hydroxide, potassium hydroxide, calcium hydroxide, calcium carbonate, potassium carbonate, sodium hydride, or an organic base such as triethylamine or pyridine, a non-aqueous solution such as toluene. Water-soluble organic solvents such as dimethylformamide and methanol, mixed solvents of water and water-insoluble organic solvents, mixed solvents of water and water-soluble organic solvents, or monoalkyls previously prepared in aqueous solvents Examples of oxy, monoalkenyloxy or monoaralkyloxy derivatives include alkyl dihalide, alkenyl dihalide, alkyl dihalide, alkyl thioether dihalide, and hydroxy- (2,3-epoxypropan-1-yloxy) diphenyl sulfone derivative. Reaction under heating condition More can be prepared phenyl sulfone derivative of interest.

In addition, for example, in the presence of an inorganic base such as sodium hydroxide, potassium hydroxide, calcium hydroxide, calcium carbonate, potassium carbonate, sodium hydride, or an organic base such as triethylamine or pyridine, toluene or the like is used. Water-insoluble organic solvents, water-soluble organic solvents such as dimethylformamide and methanol, a mixed solvent of water and a water-insoluble organic solvent, a mixed solvent of water and a water-soluble organic solvent, or in an aqueous solvent, such as dihydroxydiphenyl sulfoxide or The derivative, dihydroxydiphenylthioether or a derivative thereof is reacted with an alkyl dihalide, an alkenyl dihalide, a dihalogenated ether, a dihalogenated thioether or the like under heating conditions to obtain a corresponding bis (hydroxyphenylsulfonylphenyloxy) alkyl derivative, Producing (hydroxyphenyl aminosulfonylphenyl oxy) alkenyl derivative, bis (hydroxyphenyl aminosulfonylphenyl oxy) alkyl ether derivative, a bis (hydroxyphenyl aminosulfonylphenyl oxy) alkyl thioether derivatives. Then, in the presence of an inorganic base such as sodium hydroxide, potassium hydroxide, calcium hydroxide, calcium carbonate, potassium carbonate, sodium hydride, or an organic base such as triethylamine or pyridine, a non-aqueous solution such as toluene. Water-soluble organic solvent such as dimethylformamide or methanol, a mixed solvent of water and a water-insoluble organic solvent, a mixed solvent of water and a water-soluble organic solvent, or a bis ( Hydroxyphenylsulfonylphenyloxy) alkyl derivatives, bis (hydroxyphenylsulfonylphenyloxy) alkenyl derivatives,
Bis (hydroxyphenylsulfonylphenyloxy)
By reacting an alkyl ether derivative, a bis (hydroxyphenylsulfonylphenyloxy) alkylthioether derivative, or the like with an alkyl halide, an alkenyl halide, an aralkyl halide, or the like under heating conditions, a desired phenyl sulfone derivative can be produced.

To give a specific example of the production of 2,2'-bis [4- (4-isopropoxyphenylsulfonyl) phenyloxy] diethyl ether, first, sodium hydroxide, potassium hydroxide, hydroxide In the presence of alkali such as calcium, calcium carbonate, potassium carbonate,
In an organic solvent such as toluene, in a water-toluene mixed solvent, or in an aqueous solvent, 4,4'-dihydroxydiphenyl sulfone is added with 2-chloropropane, 2-bromopropane, 2-iodopropane, etc. under heating conditions. To produce 4-isopropoxy-4'-hydroxydiphenylsulfone. Next, for example, sodium hydroxide,
Potassium hydroxide, calcium hydroxide, calcium carbonate,
In the presence of an alkali such as potassium carbonate, in an organic solvent such as toluene, in a water-toluene mixed solvent, or the like, 4-isopropoxy-4'-hydroxydiphenylsulfone was added to 2,2'-dichlorodiethyl ether,
The desired 2,2'-bis [4- (4-isopropoxyphenylsulfonyl) phenyl is reacted by reacting 2,2'-dibromodiethylether, 2,2'-diiododiethylether and the like under heating conditions. [Oxy] diethyl ether can be produced.

The phenylsulfone derivative of the present invention is usually a crystalline solid, but may be amorphous or oily. In some cases, the phenol derivative represented by the general formula (I) belongs to the present invention irrespective of the form, although the polymorph may take a crystalline polymorph.

In the present invention, the substance forming a molecular compound with the phenylsulfone derivative represented by the general formula (I) is not particularly limited as long as it can form a molecular compound with such a derivative. Specific examples include water, methanol, ethanol, isopropanol, n-butanol, n-octanol, 2-ethylhexanol, allyl alcohol, propargyl alcohol, 1,2-butanediol, 1,3-butanediol, 4-butanediol, cyclohexanediol, 2-bromo-2
-Nitropropane-1,3-diol, 2,2-dibromo-2-nitroethanol, 4-chlorophenyl-3-
Alcohols such as iodopropargyl formal and aldehydes such as formaldehyde, acetaldehyde, n-butyraldehyde, propionaldehyde, benzaldehyde, phthalaldehyde, α-bromocinnamaldehyde, phenylacetaldehyde and the like can be mentioned.

Similarly, acetone, methyl ethyl ketone, diethyl ketone, dibutyl ketone, methyl isobutyl ketone, cyclohexanone, acetylacetone, 2-
Ketones such as bromo-4'-hydroxyacetophenone, acetonitrile, acrylonitrile, n-butyronitrile, malononitrile, phenylacetonitrile, benzonitrile, cyanopyridine, 2,2-dibromomethylglutarnitrile, 2,3,5,6-tetrachloro Isophthalonitrile, 5-chloro-2,4,6-trifluoroisophthalonitrile, 1,2-dibromo-2,4-
Nitriles such as dicyanobutane, diethyl ether, dibutyl ether, tetrahydrofuran, dioxane, tetrahydropyran, dioxolan, ethers such as trioxane, methyl acetate, ethyl acetate, butyl acetate, n-
Esters such as heptyl acetate and bis-1,4-bromoacetoxy-2-butene can be exemplified.

Similarly, sulfonamides such as benzenesulfonamide, N-methylformamide, N, N-
Amides such as dimethylformamide, dicyandiamide, dibromonitrilepropionamide, 2,2-dibromo-3-nitrilopropionamide, N, N-diethyl-m-toluamide, halogenated hydrocarbons such as dichloromethane, chloroform, dichloroethylene and tetrachloroethylene Lactams such as ε-caprolactam, lactones such as ε-caprolactone, oxiranes such as arylglycidyl ether, morpholines, phenols such as phenol, cresol, resorcinol, p-chloro-m-cresol, formic acid, acetic acid, Carboxylic acids such as propionic acid, oxalic acid, citric acid, adipic acid, tartaric acid, benzoic acid, phthalic acid, salicylic acid and thiocarboxylic acids, sulfamic acids, thiocarbamic acids, thiosemicarbazides, urea , Phenylurea, diphenylurea,
Thiourea, phenylthiourea, diphenylthiourea,
Urea such as N, N-dimethyldichlorophenylurea and thioureas, isothioureas, sulfonylureas, thiophenol, allyl mercaptan, thiols such as n-butyl mercaptan, benzyl mercaptan, and sulfides such as benzyl sulfide and butyl methyl sulfide Kind,
Disulfides such as dibutyl disulfide, dibenzyl disulfide and tetramethylthiuram disulfide; sulfoxides such as dimethyl sulfoxide, dibutyl sulfoxide and dibenzyl sulfoxide; dimethyl sulfone, phenyl sulfone and phenyl- (2-cyano-2-
Examples thereof include sulfones such as (chlorovinyl) sulfone, hexabromodimethyl sulfone, and diiodomethyl paratolyl sulfone.

Similarly, thiocyanic acids and isothiocyanic acids such as thiocyanic acid methyl ester and isothiocyanic acid methyl ester, amino acids such as glycine, alanine, leucine, lysine, methionine and glutamine, amide and urethane compounds, and acid anhydrides Aromatic hydrocarbons such as benzene, toluene, xylene, alkanes, alkenes, alkynes, isocyanates such as butyl isocyanate, cyclohexyl isocyanate, and phenyl isocyanate; thiocyanates such as methylenebisthiocyanate and methylenebisisothiocyanate; Thiocyanates, nitro compounds such as tris (hydroxymethyl) nitromethane, ammonia, methylamine, ethylamine, propylamine, butylamine, pentylamino , Hexylamine, allylamine, hydroxylamine, ethanolamine, benzylamine, ethylenediamine, 1,2-propanediamine, 1,3-propanediamine, 1,4-butanediamine, 1,5-pentanediamine, 1,6-hexane Diamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, dipropylenediamine, N, N-dimethylethylenediamine, N, N'-dimethylethylenediamine, N, N-dimethyl-1,3-
Propanediamine, N-ethyl-1,3-propanediamine, trimethylhexamethylenediamine, alkyl-
Examples thereof include acyclic aliphatic amines such as t-monoamine, menthanediamine, isophoronediamine, guanidine, N- (2-hydroxypropyl) aminomethanol, cyclohexylamine, and cyclohexanediamine.

Similarly, bis (4-aminocyclohexyl) methane, pyrrolidines, azetidines, piperidines, piperazine, N-aminoethylpiperazine, N,
Piperazines such as N'-dimethylpiperazine, cycloaliphatic amines such as pyrrolines, aniline, N-methylaniline, N, N-dimethylaniline, o-phenylenediamine, m-phenylenediamine, p-phenylenediamine; Aromatic amines such as diaminodiphenylmethane, diaminodiphenylsulfone, m-chelenediamine, epoxy compound-added polyamine, Michael-added polyamine,
Mannich-added polyamine, thiourea-added polyamine,
Modified polyamines such as ketone-blocked polyamines, imidazole, 2-methylimidazole, 2-ethylimidazole, 2-isopropylimidazole, 2-n-propylimidazole, 2-ethyl-4-methylimidazole,
1-benzyl-2-methylimidazole, 2-undecyl-1H-imidazole, 2-heptadecyl-1H-imidazole, 2-phenyl-1H-imidazole, 4-
Imidazoles such as methyl-2-phenyl-1H-imidazole and 1-benzyl-2-methylimidazole, pyrrole, pyridine, picoline, pyrazine, pyridazine;
Pyrimidine, pyrazole, triazole, benzotriazole, triazine, tetrazole, purine, indole, quinoline, isoquinoline, carbazole, imidazoline, pyrroline, oxazole, piperine, pyrimidine, pyridazine, benzimidazole, indazole,
Quinazoline, quinoxaline, phthalimide, adenine,
Cytosine, guanine, uracil, 2-methoxycarbonylbenzimidazole, 2,3,5,6-tetrachloro-4-methanesulfonylpyridine, 2,2-dithio-bis- (pyridine-1-oxide), N-methylpyrrolidone Methyl 2-benzimidazolecarbamate, 2
-Pyridinethiol-1-oxide sodium, hexahydro-1,3,5-tris (2-hydroxyethyl)
-S-triazine, hexahydro-1,3,5-triethyl-s-triazine, 2-methylthio-4-t-butylamino-6-cyclopropylamino-s-triazine, N- (fluorodichloromethylthio) phthalimide, 1 -Bromo-3-chloro-5,5-dimethylhydantoin, 2-methoxycarbonylbenzimidazole,
Examples include nitrogen-containing heterocyclic compounds such as 2,4,6-trichlorophenylmaleimide.

Similarly, furan, furfuryl alcohol, tetrahydrofurfuryl alcohol, furfurylamine, pyran, coumarin, benzofuran, xanthene,
Oxygen-containing heterocyclic compounds such as benzodioxane, oxazole, isoxazole, benzoxazole, benzisoxazole, 5-methyloxazolidine, 4- (2-
Nitrobutyl) morpholine, 4,4 '-(2-ethyl-
Nitrogen- and oxygen-containing heterocyclic compounds such as 2-nitrotrimethylene) dimorpholine, thiophene, 3,3,4,4-tetrahydrothiophene-1,1-dioxide, 4,5-
Dichloro-1,2-dithiolan-3-one, 5-chloro-4-phenyl-1,2-dithiolan-3-one, 3,
3,4,4-tetrachlorotetrahydrothiophene-
Examples thereof include sulfur-containing heterocyclic compounds such as 1,1-dioxide.

Similarly, thiazole, benzothiazole, 5-chloro-2-methyl-4-isothiazoline-3
-One, 2-methyl-4-isothiazolin-3-one,
4,5-dichloro-3-n-octylisothiazoline-
3-one, 2-octyl-4-isothiazolin-3-one, 1,2-benzisothiazolin-3-one, 2-thiocyanomethylbenzothiazole, 2- (4-thiazolyl) benzimidazole, 2-thiocyanomethyl Nitrogen-containing and sulfur heterocyclic compounds such as benzothiazole, steroids such as cholesterol, brucine, quinine, alkaloids such as theophylline, cineole, hinokitiol, menthol, terpineol, borneol, nopol, citral, citronellol, citronellal,
Geraniol, menthone, eugenol, linalool,
Natural essential oils such as dimethyloctanol,
Synthetic flavors such as jasmine and lemon, ascorbic acid,
Vitamins such as nicotinic acid and nicotinamide and related compounds can be mentioned.

The molecular compound of the present invention is obtained by directly mixing the phenylsulfone derivative represented by the general formula (I) with the above-mentioned substance forming a molecular compound with the derivative, or by mixing in a solvent. Can be obtained. In the case of a substance having a low boiling point or a substance having a high vapor pressure, the target molecular compound can be obtained by allowing the vapor of these substances to act on the phenylsulfone derivative of the present invention. Further, first, a molecular compound of the phenylsulfone derivative of the present invention and a substance is generated, and the molecular compound is reacted with another substance by the above-described method to obtain a target molecular compound.

The fact that the substances obtained by these methods are indeed molecular compounds can be confirmed by thermal analysis (TG and DTA),
It can be confirmed by infrared absorption spectrum (IR), X-ray diffraction pattern, solid-state NMR spectrum, and the like. The composition of the molecular compound can be confirmed by thermal analysis, ¹ H NMR spectrum, high performance liquid chromatography (HPLC), elemental analysis, and the like.

The ratio of each component compound constituting the molecular compound of the present invention may be changed depending on the production conditions. In addition, by reacting two or more substances with the phenylsulfone derivative of the present invention, a molecular compound composed of three or more components can be obtained.

The molecular compound of the present invention is used for the purpose of selective separation of useful substances, chemical stabilization, non-volatilization, pulverization, and the like, and for the purpose of stably producing a molecular compound having a constant composition. It is preferably crystalline, and more preferably a crystalline inclusion compound. At this time, even the same molecular compound may take a polymorph. Crystallinity can be confirmed mainly by examining the X-ray diffraction pattern. The presence of polymorphs was determined by thermal analysis, X-ray diffraction pattern,
It can be confirmed by solid-state NMR and the like. Here, an clathrate is a compound in which a three-dimensional structure formed by bonding atoms or molecules has pores of an appropriate size, in which other atoms or molecules have non-covalent interactions. Indicates a substance that has entered at a constant composition ratio.

The mode of use of the molecular compound of the present invention is not particularly limited, and for example, two or more kinds of molecular compounds each composed of different component compounds can be used in combination. The molecular compound of the present invention can be used in combination with other substances as long as the intended function is not impaired.
An excipient or the like may be added to the molecular compound of the present invention to form granules or tablets for use. Further, they can be used by adding them to resins, paints, and their raw materials and raw material compositions. The molecular compound of the present invention can be used as it is as a raw material for organic synthesis, or the molecular compound can be used as a specific reaction field.

For example, in the present invention, the above general formula (I)
A phenol derivative represented by
Chloro-2-methyl-4-isothiazolin-3-one,
Isothiazolone fungicides such as 2-methyl-4-isothiazolin-3-one, antibacterial and insecticide insect repellents such as hinokitiol and 1,8-cineole, fragrances such as rosemary, antifouling agents such as isothiazolone compounds, and anhydrous. Catalysts such as curing agents for epoxy resins such as phthalic acid, tetrahydrophthalic anhydride and 2-ethyl-4-methylimidazole and curing accelerators for epoxy resins such as 1,8-diazabicyclo (4,5,0) undecene-7 Or an inclusion compound in which an organic solvent such as toluene, xylene, or pyridine is used as a guest, in addition to the action inherent to the guest compound, sustained release, reduction of skin irritation, chemical stabilization, non-volatization, powderization, Fungicides, antibacterial agents, insecticides / insect repellents, fragrances, antifouling agents, curing agents for epoxy resins, etc. that have new functions such as selective separation of useful substances The catalyst is extremely useful as an organic solvent.

[0055]

Next, the present invention will be described in more detail by way of examples, which should not be construed as limiting the present invention.

Example 1 A solution of 23.39 g (0.08 mol) of 4-isopropoxy-4'-hydroxydiphenylsulfone in 200 ml of dimethylformamide (DMF) was added with 60
After adding 3.52 g (0.088 mol) of sodium hydride at room temperature, 5.72 g (0.04 mol) of 2,2'-dichlorodiethyl ether was added at room temperature. After heating the reaction solution at 100-105 ° C for 4 hours,
MIBK (Methyl Isobutyl Ketone) 200m
and 200 ml of water were added, and the mixture was stirred at 70 to 75 ° C. for 30 minutes. After separating the organic layer at 70 to 75 ° C, the organic layer was cooled to room temperature, and the precipitated crystals were filtered to obtain crude crystals. The crude crystals were stirred at 80 ° C. for 30 minutes in a mixed solvent of 100 ml of MIBK and 100 ml of water, and then the solution temperature was lowered to room temperature. The precipitated crystals are filtered, and the desired product H
2,2'-bis [4- having a PLC purity of 88.55%
Colorless crystals of (4-isopropoxyphenylsulfonyl) phenyloxy] diethyl ether (melting point 120 ° C.) 2
0.03 g was obtained. Melting point was 197-205 ° C.

Example 2 27.24 g (0.08 mol) of 4-benzyloxy-4'-hydroxydiphenylsulfone was added to 200 m of DMF.
3.5% 60% sodium hydride in a solution of
After adding 2 g (0.088 mol) at room temperature, 2,
5.72 g of 2'-dichlorodiethyl ether (0.04
mol) was added at room temperature. 100 to 10
After heating at 5 ° C. for 4 hours, 200 ml of MIBK (methyl isobutyl ketone) and 200 ml of water were added thereto.
The mixture was stirred at 70 to 75 ° C for 0 minutes. After separating the organic layer at 70 to 75 ° C, the organic layer was cooled to room temperature, and the precipitated crystals were filtered to obtain crude crystals. The crude crystal was prepared using MIBK1
After stirring at 80 ° C. for 30 minutes in a mixed solvent of 00 ml and 100 ml of water, the solution temperature was lowered to room temperature. The precipitated crystals were filtered to obtain 23.71 g of colorless crystals of 2,2'-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxy] diethyl ether having a HPLC purity of 81.46%. . Melting point was 197-205 ° C.

Example 3 0.1 mol of 4-isopropoxy-4 '-(2,3-epoxypropan-1-yloxy) diphenylsulfone
0.1 mol of 4-isopropoxy-4'-hydroxydiphenylsulfone and 5 g of triethylamine in 100 m
Refluxed in 1 DMF solvent for 4 hours. After the reaction solution was cooled to room temperature, it was added to 520 ml of an aqueous solution containing 4 g of sodium hydroxide, whereby crystals precipitated. The crude crystals obtained by filtration were recrystallized from toluene to obtain 21 g of colorless crystals of 1,3-bis [4- (4-isopropoxyphenylsulfonyl) phenyloxy] -2-hydroxypropane as a target substance. Melting point: 164.5 ° C-170.
It was 0 ° C.

Example 4 0.1 mol of 4-benzyloxy-4 '-(2,3-epoxypropan-1-yloxy) diphenylsulfone
0.1 mol of 4-benzyloxy-4'-hydroxydiphenylsulfone and 5 g of triethylamine in 250 m
Reflux in DMF solvent for 1 h. After the reaction solution was cooled to room temperature, it was added to 520 ml of an aqueous solution containing 4 g of sodium hydroxide, whereby crystals precipitated. The crude crystals obtained by filtration are washed with methanol and toluene,
39 g of colorless crystals of 1,3-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxy] -2-hydroxypropane, which was the target substance, were obtained. Melting point is 198 ° C ~
204 ° C.

Example 5 2,2'-bis [4- (4-isopropoxyphenylsulfonyl) phenyloxy] diethyl ether (melting point: 1
(20 ° C.) 2 g was dissolved by heating in 10 ml of toluene, and then left at room temperature for 24 hours. After the solvent in the solution was distilled off by a rotary evaporator, the solution was further dried under reduced pressure at room temperature using a rotary vacuum pump for 5 hours, and 2,2'-bis [4
-(4-Isopropoxyphenylsulfonyl) phenyloxy] diethyl ether and toluene in a composition ratio of 1:
A molecular compound consisting of 1.5 (molar ratio) was obtained.

Next, benzene was used in place of toluene, and the same operation was performed to obtain a composition ratio of 2,2'-bis [4- (4-isopropoxyphenylsulfonyl) phenyloxy] diethyl ether and benzene of 1: A molecular compound consisting of 1.5 (molar ratio) was obtained. Next, o-xylene was used in place of benzene, and the same operation was performed to obtain 2,
A molecular compound having a composition ratio of 2'-bis [4- (4-isopropoxyphenylsulfonyl) phenyloxy] diethyl ether and o-xylene of 1: 2 (molar ratio) was obtained. Further, p-xylene was used in place of o-xylene, and the same operation was performed to obtain a composition ratio of 2,2'-bis [4- (4-isopropoxyphenylsulfonyl) phenyloxy] diethyl ether and p-xylene. A molecular compound consisting of 1: 1 (molar ratio) was obtained. The fact that each is a molecular compound having the above composition is determined by thermal analysis (TG / DTA), ¹ H
Confirmed by NMR and X-ray diffraction patterns. The X-ray diffraction pattern confirmed that each molecular compound was clearly crystalline. Each molecular compound has a range of about 54 ° C to 83 ° C for toluene and about 59 ° C for benzene.
O-xylene in the range of 125 ° C,
In the range of ° C, p-xylene was released in the range of approximately 65 ° C to 93 ° C. Thus, the molecular compound of the present invention powdered toluene, o-xylene and m-xylene which are liquid at room temperature, and enabled control of volatilization.

Example 6 2,2'-bis [4- (4-isopropoxyphenylsulfonyl) phenyloxy] diethyl ether (melting point: 1
20 ° C.) 2 g of o-xylene and m-xylene 1: 1
After heating and dissolving in 10 ml of a mixed solvent (volume ratio), the mixture was allowed to stand at room temperature for 24 hours. After the solvent in the solution was distilled off by a rotary evaporator, the solution was further dried under reduced pressure at room temperature using a rotary vacuum pump for 5 hours, and 2,2'-bis [4
A molecular compound having a composition ratio of (-(4-isopropoxyphenylsulfonyl) phenyloxy] diethyl ether, o-xylene and m-xylene of 1: 1.7: 0.3 (molar ratio) was obtained. It was confirmed by thermal analysis (TG / DTA), ¹ HNMR and X-ray diffraction pattern that this was a molecular compound having the above composition. The X-ray diffraction pattern confirmed that the molecular compound was clearly crystalline. This molecular compound released o-xylene and p-xylene in the range of about 65 ° C to 120 ° C. Thus, the molecular compound of the present invention more selectively included o-xylene from a mixed solution of structural isomers of o-xylene and m-xylene.

Example 7 2,2'-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxy] diethyl ether (melting point: 1
(97-205 ° C.) 2 g was dissolved in 10 ml of toluene by heating, and then left at room temperature for 24 hours. After distilling off the solvent in the solution with a rotary evaporator, the solution was further dried under reduced pressure at room temperature using a rotary vacuum pump for 5 hours, and 2,2'-
Bis [4- (4-benzyloxyphenylsulfonyl)
A molecular compound having a composition ratio of phenyloxy] diethyl ether and toluene of 1: 0.25 (molar ratio) was obtained. Next, benzene was used in place of toluene, and the same operation was performed to obtain a composition ratio of 1: 0 of 2,2'-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxy] diethyl ether and o-xylene. .5 (molar ratio)
Was obtained.

Next, o-xylene was used in place of benzene, and the same operation was carried out to give 2,2'-bis [4- (4-
Benzyloxyphenylsulfonyl) phenyloxy]
The composition ratio of diethyl ether and o-xylene is 1: 0.
A molecular compound consisting of 5 (molar ratio) was obtained. Further, p-xylene was used in place of o-xylene, and the same operation was performed to obtain 2,2'-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxy] diethyl ether and p-xylene.
-A molecular compound having a composition ratio with xylene of 1: 0.2 (molar ratio) was obtained. Further, m-xylene was used in place of p-xylene, and the same operation was carried out to obtain 2,2'-bis
A molecular compound having a composition ratio of [4- (4-benzyloxyphenylsulfonyl) phenyloxy] diethyl ether and m-xylene of 1: 0.2 (molar ratio) was obtained.
The fact that each is a molecular compound of the above composition is determined by thermal analysis (T
G / DTA), ¹ HNMR and X-ray diffraction pattern. The X-ray diffraction pattern confirmed that each molecular compound was clearly crystalline. Each molecular compound has toluene in the range of about 68 ° C to 92 ° C, benzene in the range of about 70 ° C to 101 ° C, o-xylene in the range of about 90 ° C to 114 ° C, and p-xylene in the range of about 2 ° C.
At around 05 ° C, m-xylene was released in the range of approximately 78 ° C to 102 ° C. Thus, the molecular compound of the present invention powdered toluene, o-xylene and p-xylene which are liquid at room temperature, and enabled control of volatilization.

Example 8 2,2'-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxy] diethyl ether (melting point: 1
(97-205 ° C.) 2 g was dissolved by heating in 10 ml of a 1: 1 (volume ratio) mixed solvent of o-xylene and m-xylene, and then left at room temperature for 24 hours. After the solvent in the solution was distilled off with a rotary evaporator, the residue was further dried under reduced pressure at room temperature using a rotary vacuum pump for 5 hours, and 2,2'-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxy] diethyl ether was used. Thus, a molecular compound having a composition ratio of 1: 0.5 (molar ratio) of o-xylene was obtained. It was confirmed by thermal analysis (TG / DTA), ¹ HNMR and X-ray diffraction pattern that this was a molecular compound having the above composition. The X-ray diffraction pattern confirmed that the molecular compound was clearly crystalline. This molecular compound released o-xylene in the range of approximately 82 ° C to 106 ° C. Thus, the molecular compound of the present invention can be obtained from a mixed solution of structural isomers o-xylene and m-xylene by
-Xylene was selectively included.

Example 9 2 g of 1,3-bis [4- (4-isopropoxyphenylsulfonyl) phenyloxy] -2-hydroxypropane (melting point: 164.5 ° C. to 170.0 ° C.) was heated to 10 ml of o-xylene. After dissolution, it was left at room temperature for 24 hours. After the solvent in the solution was distilled off using a rotary evaporator, the solution was further dried under reduced pressure at room temperature using a rotary vacuum pump for 5 hours to give 1,3-bis [4- (4-isopropoxyphenylsulfonyl) phenyloxy] -2-oxy. A molecular compound having a composition ratio of hydroxypropane to o-xylene of 1: 2 (molar ratio) was obtained. Next, chloroform was used in place of o-xylene, and the same operation was performed to obtain 1,
A molecular compound having a composition ratio of 3-bis [4- (4-isopropoxyphenylsulfonyl) phenyloxy] -2-hydroxypropane and chloroform of 1: 0.25 (molar ratio) was obtained. Further, acetone was used in place of chloroform, and the same operation was performed to obtain 1,3-bis [4-
A molecular compound having a composition ratio of (4-isopropoxyphenylsulfonyl) phenyloxy] -2-hydroxypropane and acetone of 1: 0.2 (molar ratio) was obtained.

It was confirmed by thermal analysis (TG / DTA), ¹ HNMR, and X-ray diffraction pattern that each was a molecular compound having the above composition. The X-ray diffraction pattern confirmed that each molecular compound was clearly crystalline.
Each molecular compound converts o-xylene to approximately 63 ° C to 80 ° C.
C., chloroform was released in the range of about 95-140.degree. C., and acetone was released in the range of about 110-150.degree. Thus, the molecular compound of the present invention powdered o-xylene, chloroform and acetone which are liquid at room temperature, and enabled control of volatilization.

Example 10 After heating and dissolving 2 g of 1,3-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxy] -2-hydroxypropane (melting point: 198 ° C. to 204 ° C.) in 10 ml of tetrahydrofuran, at room temperature It was left for 24 hours.
After the solvent in the solution was distilled off using a rotary evaporator, the solution was further dried under reduced pressure at room temperature using a rotary vacuum pump for 5 hours, and 1,3-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxy] -2- 1: 1 composition ratio of hydroxypropane and tetrahydrofuran
(Molar ratio) was obtained. Next, 1,4-dioxane was used in place of tetrahydrofuran, and the same operation was carried out to give 1,3-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxy] -2-hydroxypropane and 1,4-dioxane. Composition ratio with dioxane 1:
A molecular compound consisting of 1.5 (molar ratio) was obtained.

Further, dimethylformamide was used in place of 1,4-dioxane, and the same operation was carried out to give 1,3-dioxane.
Bis [4- (4-benzyloxyphenylsulfonyl)
A molecular compound having a composition ratio of phenyloxy] -2-hydroxypropane and dimethylformamide of 1: 0.2 (molar ratio) was obtained. Further, dimethylformsulfoxide was used in place of dimethylformamide, and the same operation was performed to obtain a composition ratio of 1,3-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxy] -2-hydroxypropane and dimethylsulfoxide. A molecular compound consisting of 1: 1 (molar ratio) was obtained. Further, pyridine was used in place of dimethyl sulfoxide, and the same operation was performed to obtain a composition ratio of 1,3-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxy] -2-hydroxypropane to pyridine of 1: 2. (Molar ratio) was obtained. Furthermore, chloroform was used in place of pyridine, and the same operation was performed to obtain 1,3-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxy]-.
A molecular compound having a composition ratio of 2-hydroxypropane and chloroform of 1: 1.5 (molar ratio) was obtained.

It was confirmed by thermal analysis (TG / DTA), ¹ HNMR and X-ray diffraction pattern that each was a molecular compound having the above-mentioned composition. The X-ray diffraction pattern confirmed that each molecular compound was clearly crystalline.
Each molecular compound is tetrahydrofuran at about 65 ° C
~ 82 ° C, 1,4-dioxane at about 78 ° C ~
Dimethyl sulfoxide in the range of 89 ° C, approximately 100 ° C
Emitted in the range of ~ 127 ° C, pyridine in the range of approximately 72 ° C to 86 ° C, and chloroform in the range of approximately 65 ° C to 85 ° C. Thus, the molecular compound of the present invention powdered tetrahydrofuran, 1,4-dioxane, dimethylformamide, dimethylsulfoxide, pyridine, and chloroform which are liquids at room temperature, and enabled control of volatilization.

Comparative Example 1 In Examples 1 to 6, 2,2'-bis [4-
(4-isopropoxyphenylsulfonyl) phenyloxy] diethyl ether, 2,2'-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxy] diethyl ether, 1,3-bis [4- (4-isopropoxy) Instead of phenylsulfonyl) phenyloxy] -2-hydroxypropane, 1,3-bis [4- (4-benzyloxyphenylsulfonyl) phenyloxy] -2-hydroxypropane, 4,4'-dihydroxydiphenylsulfone and The same experiments as in Examples 1 to 6 were performed, except that 2,4'-dihydroxydiphenyl sulfone was used. However, 4,4'-dihydroxydiphenylsulfone and 2,4'-dihydroxydiphenylsulfone did not form a molecular compound with any of the compounds.

[0072]

Industrial Applicability The novel molecular compound of the present invention can be prepared by a simple operation and can impart functions such as chemical stabilization, non-volatilization, sustained release, and powdering of various substances. In addition, selective separation and recovery of specific substances can be performed. Further, the molecular compound of the present invention can be used in combination with various substances, and can also be used in various forms. Therefore, the present invention can be used in a very wide range of fields, and has great industrial significance.

Claims (6)

[Claims] 1. A compound of the general formula (I) [Wherein, Y may have a straight-chain or a branch,
Saturated or unsaturated hydrocarbon group having 1 to 12 carbon atoms, 1 carbon atom having an ether bond or a thioether bond
To 8 hydrocarbon groups, (R represents a methylene group or an ethylene group), or (T represents a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms), and R ¹ , R ² , R ³ and R ⁴ may be the same or different from each other, and represent a hydrogen atom, a halogen atom, a C ¹ to C ⁸ It represents an alkyl group, an alkenyl group of C2-C8, R ⁵ and R
⁶ may be the same or different and may have a linear or branched C1 to C8 alkyl group, a linear or branched C2 to C8 alkenyl group,
A C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkoxy group, a hydroxyl group or a cyclohexyl group optionally having a halogen atom, C1
-C4 alkyl group, C2-C4 alkenyl group, C1-C4 alkoxy group, hydroxyl group or cyclopentyl group optionally having a halogen atom, C
A C1-C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkoxy group, a hydroxyl group or a benzyl group which may have a halogen atom,
A C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkoxy group, a hydroxyl group or a phenethyl group which may have a halogen atom;
Α-methylbenzyl group optionally having 4 alkyl groups or C2 to C4 alkenyl groups or C1 to C4 alkoxy groups or hydroxyl groups or halogen atoms, or C1 to C4 alkyl groups or C2 to C4 alkenyl groups or Represents a C1 to C4 alkoxy group or a hydroxyl group or a naphthylmethyl group which may have a halogen atom, m represents any one of 0, 1, and 2, n, p,
q or r represents 0 or an integer of 1 to 4,
However, when n, p, q or r is 2 or more,
R ¹ , R ² , R ³ or R ⁴ represent the same or different groups, respectively]]. 2. A compound of the general formula (II) wherein m in the general formula (I) is 2. The phenylsulfone derivative according to claim 1, which is represented by the formula: 3. A molecular compound comprising a phenylsulfone derivative represented by the general formula (I) as a component compound. 4. A phenylsulfone derivative represented by the general formula (I) and an antibacterial agent, an antifungal agent, an insecticide, a pest repellent, a fragrance, a deodorant which reacts with the phenylsulfone derivative to form a molecular compound. 4. The molecular compound according to claim 3, wherein a deodorant, an antifouling agent, a curing agent and a curing accelerator for paints, resins and adhesives, a natural essential oil, an antioxidant, a vulcanization accelerator or an organic solvent are used as component compounds. 5. The molecular compound according to claim 3, wherein the molecular compound is an inclusion compound. 6. A phenylsulfone derivative represented by the general formula (I)
The molecular compound according to any one of claims 3 to 5, which is a phenylsulfone derivative represented by I).