JPH08259485A - New bisphenol compound and its production - Google Patents

Abstract

PURPOSE: To obtain a new compound suitable as a raw material for an epoxy resin useful as a sealing material for an integrated circuit having excellent water resistance, insulating properties, low dielectric properties, etc., a laminating material, etc., a developer useful for heat-sensitive recording and a fading inhibitor, having excellent solubility in various organic solvents. CONSTITUTION: This compound is shown by formula I [a (substituted) phenylmethylene is bonded to a phenol nucleus at the p- or o-position based on the phenolic, OH; R1 and R2 are each a 1-4C alkyl; R is R1 or a 1-4C alkoxy; n is 0-2] such as 4,4'-(phenylmethylene)bis(2,3,6-trimethylphenyl). The compound of formula I is obtained by reacting a compound of formula II with a compound of formula III in the presence of an acid catalyst such as hydrochloric acid or p-toluenesulfonic acid in an alcoholic solvent such as methanol.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a novel bisphenol compound and a method for producing a high-purity product thereof.
The present invention relates to a trisphenylmethane-type bisphenol compound, in which each phenol nucleus has three lipophilic alkyl groups as substituents, and a novel bisphenol compound and a method for producing a highly pure product thereof.

[0002]

2. Description of the Related Art Bisphenol compounds have hitherto been used as raw materials for thermoplastic engineering plastics such as polycarbonate and polyarylate, epoxy resins,
It is widely used as a raw material for thermosetting resins such as polyimide resins. In recent years, especially with the miniaturization and high performance of devices in the electric and electronic fields, not only the mechanical properties and thermal properties of organic materials used for them have been improved, but also moisture resistance, electrical insulation, low There has been a strong demand for further improvement in dielectric properties.

Further, the bisphenol compound is not only used as a raw material for the above-mentioned plastics, but also as a curing agent for epoxy resin, a developer for heat-sensitive recording, an anti-fading agent, a storage stabilizer, an antioxidant, a germicide, It is also effectively used as various additives such as antibacterial and antifungal agents, and its importance is increasing more and more. Bisphenol compounds are, for example, Eu
edited by gen Mueller, METHODEN DER ORGANI-SCHEN CHEMIE
(HOUBEN-WEYL), Band VI / 1c, "Phenol", Teil 2, pp. 1
Many are described in 021-1061, Georg Thieme Verlag Stuttgart (1976) .After that, many new bisphenol compounds were added to meet the demand for higher performance and higher functionality of resins as described above. ,Proposed.

Among such bisphenol compounds, a trisphenylmethane type bisphenol compound can be obtained by condensing a relatively inexpensive benzaldehyde with a phenol compound. Therefore, various phenols have been conventionally used in this method. Various bisphenol compounds used in this class have been proposed. Of these, the bisphenol compounds having an alkyl group as a substituent in the phenol nucleus have an alkyl group that is lipophilic,
Since it is easily dissolved in various organic solvents, it can be applied not only to applications using various solvents, but by using this as a raw material, it has low water absorption, low moisture absorption, etc. It is expected to provide a resin having excellent electrical characteristics such as electrical conductivity and low dielectric property.

Conventionally, a bisphenol compound having an alkyl group as a substituent in the phenol nucleus and having a relatively large number of substituted alkyl groups is disclosed in Japanese Patent Laid-Open No. Sho 63-63.
-215651 gazette and F. Yamada et al., Bull. Chem. So
c. Japan, 62 (11), 3603 (1989), 4,4'- (phenylmethylene) bis (2,5-dimethylphenol) RS
Bhute, Man-Made Text. India, 30 (8), 398 (1987) and
F. Yamada et al., Bull. Chem. Soc. Japan, 62 (11), 360.
3 (1989), 4,4 '-(phenylmethylene) bis (2,6-dimethylphenol), and JP-A-63-21565.
Bulletin 1 and F. Yamada et al., Bull. Chem. Soc. Japan, 62.
(11), 3603 (1989) disclose 4,4 ′-(phenylmethylene) bis (2-t-butyl-5-methylphenol), respectively.

However, for a single phenol nucleus, 3
No bisphenol compound having a trisphenylmethane structure in which one or more alkyl groups are substituted has heretofore been known. Such an alkyl polysubstituted bisphenol compound has excellent solubility in the organic solvent as described above and can be applied to a wide range of applications. In addition, by using this as a raw material, various properties such as water resistance and electrical characteristics can be obtained. It can be expected to give a resin with further improved performance, especially when relatively small bulky alkyl groups are present as a large number of substituents, the free volume around the phenol nucleus becomes small,
In particular, it can be expected that the water resistance, and hence the long-term retention of electrical characteristics and the like, will be improved.

[0007]

In view of the above-mentioned circumstances of the bisphenol compound, the present invention has excellent solubility in various organic solvents and can be applied to various applications. By using, low water absorption,
A novel bisphenol compound expected to give a resin having excellent water resistance such as low hygroscopicity and electrical characteristics such as insulation and low dielectricity, especially 3 or more for a single phenol nucleus It is an object of the present invention to provide a bisphenol compound having a trisphenylmethane structure in which the alkyl group is substituted, and a method for producing such a bisphenol compound.

[0008]

The novel bisphenol compounds according to the present invention have the general formula (I)

[0009]

Embedded image

(In the formula, the substituted or unsubstituted phenylmethylene group is bonded to the phenol nucleus at the para or ortho position with respect to the phenolic hydroxyl group, and R ¹ and R
² independently represents an alkyl group having 1 to 4 carbon atoms, and R is an alkyl group having 1 to 4 carbon atoms or 1 to 4 carbon atoms.
And an n is 0, 1 or 2. ) Is represented.

Specific preferred examples of such a bisphenol compound according to the present invention include, for example, 2,2 '-(phenylmethylene) bis [3,5,6-trimethylphenol] and 4,4'-(phenylmethylene). ) Bis [2,3,6-trimethylphenol], 2,2 '-[(4-methylphenyl)
Methylene] bis [3,5,6-trimethylphenol], 4,
4 '-[(4-methylphenyl) methylene] bis [2,3,6
-Trimethylphenol], 2,2 '-[(4-isopropylphenyl) methylene] bis [3,5,6-trimethylphenol], 4,4'-[(4-isopropylphenyl) methylene] bis [2,3 , 6-Trimethylphenol], 2,2'-
[(2-Methoxyphenyl) methylene] bis [3,5,6-
Trimethylphenol], 4,4 '-[(2-methoxyphenyl) methylene] bis [2,3,6-trimethylphenol], 2,2'-[(4-methoxyphenyl) methylene] bis [3,5, 6-trimethylphenol], 4,4 '-[(4-
Methoxyphenyl) methylene] bis [2,3,6-trimethylphenol], 2,2 ′-[(2-ethoxyphenyl) methylene] bis [3,5,6-trimethylphenol], 4,4 ′
-[(2-Ethoxyphenyl) methylene] bis [2,3,6
-Trimethylphenol], 2,2 '-[(4-ethoxyphenyl) methylene] bis [3,5,6-trimethylphenol], 4,4'-[(4-ethoxyphenyl) methylene] bis [2,3 , 6-Trimethylphenol], 2,2 '-[(4-
Butoxyphenyl) methylene] bis [3,5,6-trimethylphenol], 4,4 ′-[(4-butoxyphenyl) methylene] bis [2,3,6-trimethylphenol] and the like can be mentioned. However, it is not limited to these.

Among these, bisphenol compounds obtained by using hensaldehyde, which is industrially available at low cost, ie, 2,2 '-(phenylmethylene)
Preferred specific examples include bis [3,5,6-trimethylphenol] and 4,4 ′-(phenylmethylene) bis [2,3,6-trimethylphenol].

The novel bisphenol compound according to the present invention has the general formula (II) in the presence of an acid catalyst in an alcohol solvent.

[0014]

[Chemical 6]

(In the formula, R ¹ and R ² each independently represent an alkyl group having 1 to 4 carbon atoms), and a general formula (III)

[0016]

[Chemical 7]

(In the formula, R represents an alkyl group having 1 to 4 carbon atoms or an alkoxyl group having 1 to 4 carbon atoms, n is 0,
Indicates 1 or 2. ) It can be obtained by reacting with an aromatic aldehyde represented by.

In the trialkylphenol compound represented by the general formula (II), R ¹ and R ² each independently represent an alkyl group having 1 to 4 carbon atoms, and specifically, for example, a methyl group or an ethyl group. Is a linear or branched propyl group or a butyl group, and in the aromatic aldehyde represented by the general formula (III), R is a carbon number of 1 to 1.
4 represents an alkyl group having 4 or an alkoxyl group having 1 to 4 carbon atoms, n represents 0, 1 or 2, and examples of the alkyl group include a methyl group, an ethyl group, a linear or branched propyl group. Or a butyl group, and examples of the alkoxyl group include a methoxy group, an ethoxy group, a linear or branched propoxy group or a butoxy group.

In particular, according to the present invention, in such a method, after the reaction, the acid catalyst in the reaction solution containing the above-mentioned bisphenol compound is neutralized, and then the aromatic hydrocarbon and the fat are added to the reaction solution. A high-purity product can be easily obtained by adding a mixed solvent of a group ketone to dissolve the bisphenol compound and then cooling the reaction solution to crystallize the bisphenol.

Specific examples of the trialkylphenol compound represented by the above general formula (II) used in the production of the bisphenol compound according to the present invention include:
2,3,5-trimethylphenol, 2,3,6-trimethylphenol, 2,5-diethyl-3-methylphenol, 2,
6-dimethyl-3-methylphenol, 2,5-diisopropyl-3-methylphenol, 2,6-diisopropyl-3-methylphenol, 2,5-di-t-butyl-3-
Methylphenol, 2,6-di-t-butyl-3-methylphenol and the like can be mentioned. Among these, 2,3,5-trimethylphenol and 2,3,6-trimethylphenol, which are industrially easily available, are particularly preferably used.

As described above, in the case of producing the bisphenol compound according to the present invention, when 2,3,6-trimethylphenol is used as the trialkylphenol compound, the reaction product is substantially 4,4 '. −
It consists of [(substituted phenyl) methylene] bis [2,3,6-trimethylphenol]. However, when 2,3,5-trimethylphenol is used as the trialkylphenol compound, 2,2 '-[(substituted phenyl) methylene] bis [3,5,6-trimethylphenol] is produced as a main product. In addition, 4,4 '-[(substituted phenyl) methylene] bis [2,3,5-trimethylphenol] and 2,4'-
A small amount of [(substituted phenyl) methylene] [2,3,5-trimethylphenol] [3,5,6-trimethylphenol] is by-produced.

However, after reacting 2,3,5-trimethylphenol with an aromatic aldehyde, as described below,
Neutralize the acid catalyst in the reaction solution containing the precipitated mixture of bisphenol compounds, and then add a mixed solvent of an aromatic hydrocarbon and an aliphatic ketone to the reaction solution to dissolve the mixture of bisphenol compounds, Cool the reaction,
By crystallizing, 2,2'- which is the main product
[(Substituted phenyl) methylene] bis [3,5,6-trimethylphenol] can be isolated as a purified product.

Specific examples of the aromatic benzaldehyde represented by the general formula (III) used in the production of the bisphenol compound include benzaldehyde, 2-methylbenzaldehyde (o-tolualdehyde) and 3-methylbenzaldehyde. (M-tolualdehyde), 4-methylbenzaldehyde (p-tolualdehyde), 4-ethylbenzaldehyde, 4-isopropylbenzaldehyde (cuminaldehyde), 4-t-butylbenzaldehyde, 2,4-dimethylbenzaldehyde, 2,5- Dimethylbenzaldehyde, 3,4-dimethylbenzaldehyde, 3,5-dimethylbenzaldehyde,
2-methyl-4-isopropylbenzaldehyde, 2-
Methoxybenzaldehyde (o-anisaldehyde),
3-methoxybenzaldehyde (m-anisaldehyde), 4-methoxybenzaldehyde (p-anisaldehyde), 2-ethoxyberbenzaldehyde), 4-
Examples thereof include ethoxybenzaldehyde, 4-n-butoxybenzaldehyde, 3,4-dimethoxybenzaldehyde and the like. These aromatic aldehydes are
Alternatively, they are used as a mixture of two or more kinds.

Among these, benzaldehyde is industrially available at the lowest cost and is preferably used. Further, 4-methylbenzaldehyde, 4-isopropylbenzaldehyde, 2-methoxybenzaldehyde, 4-methoxybenzaldehyde, 2-ethoxybenzaldehyde, 4-ethoxybenzaldehyde, 4-butoxybenzaldehyde and the like, which are relatively inexpensive to obtain, are also preferably used. To be

The above-mentioned trialkylphenol compound is usually used in an amount of at least 2 times the molar amount of these aromatic aldehydes.
It is used in the range of 2 to 10 times by mole, preferably 3
It is used in the range of up to 5 times the molar amount.

As the alcohol solvent, methanol, ethanol, isopropyl alcohol, n-propyl alcohol, t-butyl is used in consideration of the reaction raw materials used, the solubility of the obtained product, the reaction conditions, the economic efficiency of the reaction, and the like. Lower aliphatic alcohols such as alcohol, isobutyl alcohol, n-butyl alcohol and the like are preferably used. In particular, methanol is preferably used.

In the present invention, the alcohol solvent is usually 10 to 1000 parts by weight, preferably 200 to 50 parts by weight, based on 100 parts by weight of the aromatic aldehyde used.
It is used in the range of 0 parts by weight, but is not limited thereto.

In the present invention, the acid catalyst is preferably an acid soluble in an alcohol solvent which is a reaction solvent, and therefore, for example, hydrochloric acid, sulfuric acid, sulfuric anhydride, p-toluenesulfonic acid, methanesulfonic acid, trifluoride. Preferable specific examples include methanesulfonic acid, oxalic acid, formic acid, phosphoric acid, trichloroacetic acid, trifluoroacetic acid and the like. Such an acid catalyst is, for example, 35%
In the case of hydrochloric acid, it is used in an amount of 0.01 to 1 part by weight, preferably 0.05 to 0.5 part by weight, based on 100 parts by weight of the aromatic aldehyde.

The reaction is usually carried out at room temperature to 80 ° C., preferably at 40 to 65 ° C. under a nitrogen stream while stirring.
It may be carried out for about 24 hours, usually about 5-10 hours. In the present invention, normally, the bisphenol compound produced by the reaction is difficult to dissolve in the reaction solvent, and therefore, is precipitated in the reaction solution under the above reaction temperature conditions. Therefore, according to the present invention, after completion of the reaction, an alkali such as aqueous ammonia is added to the obtained reaction solution to neutralize it to pH 5 to 7 to neutralize the acid catalyst. A mixed solvent consisting of a hydrocarbon and an aliphatic ketone is added, the bisphenol compound is dissolved and then cooled to crystallize the target bisphenol compound, thus,
A high-purity product can be obtained.

In the present invention, the mixed solvent comprising an aromatic hydrocarbon and an aliphatic ketone used as the crystallization solvent is
Considering crystallization conditions, purification effect, economic efficiency, etc., examples of aromatic hydrocarbons include toluene, xylene, cumene, etc., and examples of ketones include isopropyl ketone, methyl ethyl ketone, methyl isobutyl. Examples thereof include ketone and diisopropyl ketone.

Therefore, specific examples of the preferable mixed solvent which can be used in the present invention include, for example, toluene-methyl ethyl ketone, toluene-diisopropyl ketone, toluene-methyl isobutyl ketone, xylene-methyl ethyl ketone, xylene-diisopropyl ketone,
Xylene-methyl isobutyl ketone, cumene-methyl ethyl ketone, cumene-diisopropyl ketone, cumene-
Methyl isobutyl ketone etc. can be mentioned. According to the present invention, such a mixed solvent comprising an aromatic hydrocarbon and a ketone has an aromatic hydrocarbon / ketone ratio of usually 1/5 to 20/1, preferably 1/20.
It is in the range of 1 to 10/1.

Such a crystallization solvent is usually used in the reaction solution 10
The target bisphenol compound can be crystallized with high purity from the reaction solution by adding it in an amount of 100 to 1000 parts by weight, preferably 200 to 500 parts by weight, relative to 0 parts by weight. In particular, in the present invention, by using toluene-methylisobutylketone as a crystallization solvent, it is possible to obtain highly pure bisphenol compound crystals, usually granular white crystals having a purity of 99.9% or more. When only hydrocarbon is used as the crystallization solvent, only pale yellow powdery crystals containing a large amount of impurities are obtained.

On the other hand, as described above, for example, 2,3,5-
When trimethylphenol is reacted with an aromatic aldehyde, a mixture in which 2,3,5-trimethylphenol is bonded to a substituted phenylmethylene group at various positions is formed, and therefore, as described above, crystallization leads to the purpose of Do
2,2 '-[(substituted phenyl) methylene] bis [3,5,6-trimethylphenol] can be separated and purified,
However, as a matter of course, the mixture may be used as it is for an appropriate use, if necessary.

[0034]

The bisphenol compound according to the present invention is
Since it has a trisphenylmethane type skeleton and each alkyl group has three alkyl groups as substituents and has excellent solubility in various organic solvents, it can be advantageously used in a wide range of applications. . Further, the bisphenol compound according to the present invention, when used as a raw material, gives a resin having excellent electrical properties such as water resistance such as low water absorption and low hygroscopicity, insulation properties and low dielectric properties.

[0035]

The present invention will be described below with reference to examples.
The present invention is not limited to these examples.

Example 1 (Production of 4,4 '(phenylmethylene) bis (2,3,6-trimethylphenol)) 2,3 in four 1000 ml capacity flasks equipped with a thermometer, a condenser and a stirrer. , 6-Trimethylphenol 136.0 g, benzaldehyde 42.4
g, 204 g of methanol and 20.4 g of 35% hydrochloric acid were charged, and the mixture was reacted at 40 ° C. for 24 hours. After the reaction was completed, the reaction solution containing the precipitated bisphenol compound was neutralized with an aqueous sodium hydroxide solution and then filtered. The obtained crude crystals were recrystallized with a mixed solvent of toluene and methyl isobutyl ketone to obtain 103.9 g of the title compound as a pale yellow crystal (purity 99.9%, yield 72%).

Melting point: 183.3 ° C. Infrared absorption spectrum (KBr, cm ⁻¹ ): 3320, 2940,
2920, 1595, 1580 Proton nuclear magnetic resonance spectrum (CDCl ₃ / (CD ₃ ) ₂ SO,
δ): 2.02 (s, 12H), 2.13 (s, 6H), 5,67 (s, 1H),
6.29 (s, 2H), 6.80-7.40 (m, 5H), 7.80 (s, 2H) GC-MS: 209, 345, 360 (M ⁺ ), 223, 283

Example 2 (4,4 '-[(4-methylphenyl) methylene] bis (2,4
Manufacture of 3,6-trimethylphenol) 2 in four 300 ml capacity flasks equipped with thermometer, condenser and stirrer
3,6-Trimethylphenol 17.0 g, p-tolualdehyde 5.0 g, methanol 25 g and 35% hydrochloric acid 1.7 g were charged and reacted at 40 ° C. for 24 hours. After the reaction was completed, the reaction solution containing the precipitated bisphenol compound was neutralized with an aqueous sodium hydroxide solution and then filtered. The crude crystals obtained were mixed with a mixed solvent of toluene and methyl isobutyl ketone to obtain 2
The crystals were recrystallized twice to give 10.1 g of the title compound as white crystals.
(Purity 99.7%, yield 65%) was obtained.

Melting point: 196.6 ° C. Infrared absorption spectrum (KBr, cm ⁻¹ ): 3570, 3450,
2990, 2970, 2920, 2850, 1575, 1505 Proton nuclear magnetic resonance spectrum (CDCl ₃ / (CD ₃ ) ₂ SO,
δ): 1.98 (s, 6H), 2.03 (s, 6H), 2.11 (s, 6H), 2.
30 (s, 3H), 5,60 (s, 1H), 6.30 (s, 2H), 6.91 (d, J =
8.0Hz, 2H), 7.15 (d, J = 8.0Hz, 2H), 7.76 (s, 2H) GC-MS: 223, 359, 374 (M ⁺ ), 224, 239

Example 3 (Production of 4,4 '-[(4-isopropylphenyl) methylene] bis (production of 2,3,6-trimethylphenol) Four 300 ml volumes equipped with a thermometer, a condenser and a stirrer. In a flask, 2,3,6-trimethylphenol 13.8 g, cumin aldehyde 5.0 g, methanol 45 g and 35% hydrochloric acid 1.4
g was charged and reacted at 40 ° C. for 24 hours. After the reaction was completed, the reaction solution containing the precipitated bisphenol compound was neutralized with an aqueous sodium hydroxide solution and then filtered. The obtained crude crystals were recrystallized twice with a mixed solvent of toluene and methyl isobutyl ketone to give the title compound 5.5 as white crystals.
g (purity 99.7%, yield 41%) was obtained.

Melting point: 187.0 ° C. Infrared absorption spectrum (KBr, cm ^-1 ): 3570, 2960,
2920, 2870, 1575, 1510 Proton nuclear magnetic resonance spectrum (CDCl ₃ / (CD ₃ ) ₂ SO,
δ): 1.22 (d, J = 6.4Hz, 6H), 2.88 (q, J = 6.4Hz, 1
H), 2.02 (s, 6H), 2.03 (s, 6H), 2.13 (s, 6H), 5,62
(s, 1H), 6.32 (s, 2H), 6.97 (d, J = 8.0Hz, 2H), 7.22
(d, J = 8.0Hz, 2H), 7.78 (s, 2H) GC-MS: 223, 387, 402 (M ⁺ ), 267, 388

Example 4 (4,4 '-[(4-methoxyphenyl) methylene] bis (production of 2,3,6-trimethylphenol) Four 300 ml volumes equipped with thermometer, condenser and stirrer In a flask, 2,3,6-trimethylphenol 15.0 g, p-anisaldehyde 5.0 g, methanol 65 g and 35% hydrochloric acid 1.
2 g was charged and reacted at 40 ° C. for 24 hours. After the reaction was completed, the reaction solution containing the precipitated bisphenol compound was neutralized with an aqueous sodium hydroxide solution and then filtered. The obtained crude crystals were recrystallized twice with a mixed solvent of toluene and methyl isobutyl ketone to give the title compound 10.
4 g (purity 99.6%, yield 73%) was obtained.

Melting point: 187.4 ° C. Infrared absorption spectrum (KBr, cm ⁻¹ ): 3580, 3500,
2920, 1605, 1580, 1505 Proton nuclear magnetic resonance spectrum (CDCl ₃ / (CD ₃ ) ₂ SO,
δ): 1.98 (s, 6H), 2.01 (s, 6H), 2.11 (s, 6H), 3.
77 (s, 3H), 5.56 (s, 1H), 6.28 (s, 2H), 6.90 (s, 4
H), 7.76 (s, 2H) GC-MS: 375, 390 (M ⁺ ), 223, 239, 255

Example 5 (2,2 '-[(4-methylphenyl) methylene] bis (3,
Production of 5,6-trimethylphenol) 2 in four 300 ml capacity flasks equipped with thermometer, condenser and stirrer.
3,5-Trimethylphenol 17.0 g, p-tolualdehyde 5.0 g, methanol 25 g and 35% hydrochloric acid 1.7 g were charged and reacted at 40 ° C. for 24 hours. After the reaction was completed, the reaction solution containing the precipitated bisphenol compound was neutralized with an aqueous sodium hydroxide solution and then filtered. The crude crystals obtained were mixed with a mixed solvent of toluene and methyl isobutyl ketone to obtain 2
The crystals were recrystallized twice to give 1.3 g of the title compound as white crystals (purity: 98.6%, yield: 8%).

Melting point: 170.2 ° C. Infrared absorption spectrum (KBr, cm ⁻¹ ): 3470, 2970,
2940, 2920, 2860, 1610, 1560, 1505 Proton nuclear magnetic resonance spectrum (CDCl ₃ / (CD ₃ ) ₂ SO,
δ): 2.02 (s, 6H), 2.17 (s, 12H), 2.99 (s, 3H),
5.76 (s, 1H), 6.65 (s, 2H), 6.91 (d, J = 7.2Hz, 2H),
7.10 (d, J = 7.2Hz, 2H), 8.31 (s, 2H) GC-MS: 223, 239, 237, 224, 374 (M ⁺ )

Example 6 (2,2 '-[(2-methoxyphenyl) methylene] bis (production of 3,5,6-trimethylphenol) Four 300 ml volumes equipped with thermometer, condenser and stirrer In a flask, 2,3,5-trimethylphenol 15.0 g, o-anisaldehyde 5.0 g, methanol 15 g and 35% hydrochloric acid 1.
5 g was charged and reacted at 40 ° C. for 24 hours. After the reaction was completed, the reaction solution containing the precipitated bisphenol compound was neutralized with an aqueous sodium hydroxide solution and then filtered. The obtained crude crystals were recrystallized twice with a mixed solvent of toluene and methyl isobutyl ketone to give the title compound 4.0 as white crystals.
g (purity 97.7%, yield 28%) was obtained.

Melting point: 257.0 ° C. (decomposition) Infrared absorption spectrum (KBr, cm ^-1 ): 3470, 2970,
2930, 2920, 2860, 2830, 1610, 1590, 1575, 1560 Proton nuclear magnetic resonance spectrum (CDCl ₃ / (CD ₃ ) ₂ SO,
δ): 2.02 (s, 6H), 2.09 (s, 6H), 2.17 (s, 6H), 3.
60 (s, 3H), 5.92 (s, 1H), 6.61 (s, 2H), 6.82-7.46
(m, 4H), 8.17 (s, 2H) GC-MS: 223, 255, 149, 224, 390 (M ⁺ )

Example 7 (2,2 '-[(4-methoxyphenyl) methylene] bis (production of 3,5,6-trimethylphenol) Four 300 ml volumes equipped with thermometer, condenser and stirrer In a flask, 2,3,5-trimethylphenol 15.0 g, p-anisaldehyde 5.0 g, methanol 15 g and 35% hydrochloric acid 1.
5 g was charged and reacted at 40 ° C. for 24 hours. After the reaction was completed, the reaction solution containing the precipitated bisphenol compound was neutralized with an aqueous sodium hydroxide solution and then filtered. The obtained crude crystals were recrystallized twice with a mixed solvent of toluene and methyl isobutyl ketone to give the title compound 4.0 as white crystals.
g (purity 98.2%, yield 28%) was obtained.

Melting point: 140.0 ° C. Infrared absorption spectrum (KBr, cm ⁻¹ ): 3440, 3290,
2940, 2920, 2870, 2830, 1610, 1580, 1560, 1505 Proton nuclear magnetic resonance spectrum (CDCl ₃ / (CD ₃ ) ₂ SO,
δ): 2.03 (s, 6H), 2.17 (s, 12H), 3.76 (s, 3H),
5.72 (s, 1H), 6.65 (s, 2H), 6.87 (s, 4H), 8.27 (s,
2H) GC-MS: 223, 253, 254, 255, 390 (M ⁺ )

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Claims (10)

[Claims] 1. A compound represented by the general formula (I): (In the formula, the substituted or unsubstituted phenylmethylene group is bonded to the phenol nucleus at the para position or the ortho position with respect to the phenolic hydroxyl group, and R ¹ and R ² each independently have 1 to 1 carbon atoms. 4 is an alkyl group, and R is 1 carbon atom
-4 is an alkyl group or an alkoxyl group having 1 to 4 carbon atoms, and n is 0, 1 or 2. ) A bisphenol compound represented by. 2. A 4,4 '(phenylmethylene) bis (2,3,6-
Trimethylphenol). 3. 4,4 '-[(4-Methylphenyl) methylene] bis (2,3,6-trimethylphenol). 4. 4,4 '-[(4-Isopropylphenyl) methylene] bis (2,3,6-trimethylphenol). 5. A 4,4 '-[(4-methoxyphenyl) methylene] bis (2,3,6-trimethylphenol). 6. A 2,2 '-[(4-methylphenyl) methylene] bis (3,5,6-trimethylphenol). 7. A 2,2 '-[(2-methoxyphenyl) methylene] bis (3,5,6-trimethylphenol). 8. A 2,2 '-[(4-methoxyphenyl) methylene] bis (3,5,6-trimethylphenol). 9. In an alcohol solvent in the presence of an acid catalyst,
General formula (II) (In the formula, R ¹ and R ² each independently have 1 to 4 carbon atoms.
Is an alkyl group. ) And a general formula (III): (In the formula, R represents an alkyl group having 1 to 4 carbon atoms or 1 carbon atom.
To 4 are shown, and n is 0, 1 or 2. ) Is reacted with an aromatic aldehyde represented by
General formula (I): (In the formula, the substituted or unsubstituted phenylmethylene group is bonded to the phenol nucleus at the para position or the ortho position with respect to the phenolic hydroxyl group, and R ¹ and R ² each independently have 1 to 1 carbon atoms. 4 is an alkyl group, and R is 1 carbon atom
-4 is an alkyl group or an alkoxyl group having 1 to 4 carbon atoms, and n is 0, 1 or 2. In the method for producing a bisphenol compound represented by the formula (4), after the reaction is completed, the acid catalyst in the reaction solution containing the precipitated bisphenol compound is neutralized, and then the reaction solution is mixed with an aromatic hydrocarbon and an aliphatic ketone. A method for producing a high-purity bisphenol compound, which comprises adding a solvent to dissolve the bisphenol compound, and then cooling the reaction solution to crystallize the bisphenol compound. 10. The method for producing a highly pure bisphenol compound according to claim 9, wherein the mixed solvent is a mixed solvent of toluene and methyl isobutyl ketone.