JPS5813528A - Novel phenolic compound and its preparation - Google Patents

Abstract

NEW MATERIAL:The phenolic compound of formulaI(R1 and R2 are H or CH3. EXAMPLE:1,3-Di(2-p-hydroxyphenyl-2-propyl)benzene. USERaw material of high-performance thermoplastic polymer (e.g. polycarbonate, polyester, etc.) and a surface active agent, or a stabilizer having durable effectiveness at high temperature. PROCESS:The compound of formulaIis prepared by reacting phenol with a compound selected from the compounds of formula II, formula III and formula IV in the presence of an acidic condensation agent (e.g. sulfuric acid, hydrochloric acid, etc.) at -20-+100 deg.C.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel phenolic compound useful as a variety of high-performance thermoplastic polymers, surfactants, raw materials for production, and stabilizers or as raw materials thereof, and a method for producing the same. be.

It is generally well known that biphenols are important starting materials for various high-performance thermoplastic polymers, such as polycarbonate, polyester, and epoxy resins. Furthermore, further improvements in heat resistance and adhesive performance are desired.

In addition, 2.6-di-t-butyl-p-cresol, which has shown excellent performance as a stabilizer in a variety of uses, has a low molecular weight and evaporates when exposed to high temperatures, resulting in its effectiveness lasting. Otherwise, there will be nine problems, and a stabilizer with a larger molecular weight is required.

In view of the current situation, the inventors of the present invention have discovered a new phenolic compound while conducting intensive studies on phenolic compounds. (wherein, R1 and Rfi represent H and CH31 groups), especially a novel phenolic compound represented by the formula /, 3-di(co-p-hydroxyph, nil-11-probyl) Regarding benzene, phenol and a compound selected from the group consisting of general formula (2) and formula (2) (wherein "II Rz is H, G (three groups are shown)) as an acidic condensing agent. In the presence of −1θ℃
The reaction was carried out at a temperature of ~/θθ℃, and the general formula (
4) A novel phenolic compound 0 production method for recovering the phenolic metal compound represented by )-isopropenylbenzene and a compound selected from the group consisting of 7,3-di(cohydropropylene)benzene represented by the formula The present invention relates to a method for producing the above-mentioned /,3-di(,2-p-hyFOXIF-winged nyl-[lambda]-propyl)benzene, which comprises recovering the benzene.

The chemical compound selected from the group consisting of general formulas 〇), (C5, and (b)) is not particularly limited in its manufacturing process, but can be manufactured using industrially common manufacturing methods such as - (in the formula, Rle
R2 represents H, G11t, or a group. ) or general formula (B) and/or formula (B) obtained by air oxidation (where R1 and R2 are H , G11J group), or the '41 compound represented by the general formula (b), obtained by the reduction treatment of sodium sulfite and hydrogen fat of the hydroperoxide represented by Compounds of general 2) and (b) obtained by dehydration in the presence of an acid catalyst,
It can be manufactured as

These compounds can be used alone or as a mixture of one or more to react.

In the practice of this invention, phenol typically has the general formula ω)(
C') 1 mol a% of the compound represented by (b) D, 2. θ
It is used in excess of ~/θ times the molar amount, preferably 20N6 times the molar amount, which is the stoichiometric amount or more.

Du ordinary sulfuric acid, hydrochloric acid, hydrogen chloride gas, as acidic condensing agent
Boron trifluoride, hydrogen fluoride, trifluoroacetic acid, acid clay, acidic ion exchange resin, etc. can be used.

If hydrogen sulfide, mercaptans, and thiophenol compounds are used in combination to aid this condensation reaction, the reaction can be carried out more efficiently.

In order to carry out the reaction smoothly, it is also possible to use an appropriate organic solvent, such as benzene, toluene, or chlorobenzene, as a solvent. The reaction temperature is usually -10"0.
The temperature is 700°C.

The reaction pressure can usually be carried out under atmospheric pressure, but when the acidic condensing agent is a gas, it is carried out under increased pressure.

In addition, when water is produced in the reaction, the acidic condensing agent is diluted with water, so in order to maintain its effectiveness, the produced water can be removed from the reaction system, so it can also be carried out under pressure. The compound represented by the general formula precipitates out as a solid from the reaction mixture, or if an organic solvent is used, the organic layer is cooled. It precipitates as a solid and can be recovered as a crude product. After removing unreacted phenol from this crude product using a conventional method such as hot water washing or steam distillation, water, alcohol, acetic acid, Chloroform, benzene,
It can be recovered as a highly pure solid by recrystallization from a solvent such as toluene or a mixture thereof.

The present invention will be explained in more detail with reference to Examples below.
The scope of the present invention is not limited by these Examples: Phenol 417 in a 300"d glass 3-trough flask
9 (0,!; mol), /, 3-di (λ- and roxycobrovir) benzene/ri, 4tp (0,1 mol), benzene/θθd%, hydrochloric acid/θθd were charged, and while stirring. The reaction was carried out at j'C for /S hours. After the reaction is complete, the ocher oil layer is separated and neutralized with a hot aqueous solution of sodium citrate.After neutralization, unreacted phenol contained in the oil layer is removed by hot water washing, and the oil layer is placed in an ice water bath. It was cooled down. A pale yellow solid was precipitated by cooling, and a pale yellow powder was obtained by filtration.

Benzene recrystallization gave a white powder with a melting point of /3~/44/''C in a yield of about 75''.

The infrared absorption spectrum, pigeon spectrum, and yiAEs spectrum of this production method and product show that it is /, J-di(λ-p-hyP-oxyphenyl-probyl)benzene with a molecular weight of 34I6 expressed as an element. Confirmed Example: Phenol 4t7 was placed in a 3θθ− glass 3 flask.
P (0.5 mol), benzene/θθ-% Minato salt yasow
*Preparation and stirring 1. Two p4tθ'Ctc #hold 0
7.3-diisopropenylbenzene and 3-(1-
Mixture I#IJ16P (0.1 mole total) of hydroxy-propylene-isopropenylbenzene was slowly added. After 1 hour of reaction, a clay-colored oil layer was obtained. This oil layer was separated and the same operation as in Example 1 was carried out. As a result, the melting point isy, s~, /4t/TC? A white powder was obtained in a yield of 7p#e, 2s. This powder has a molecular weight of 3.

The drug was confirmed to be xyphenyl-coprovir) benzene. “ Patent applicant Sumitomo Chemical Co., Ltd.

Claims (1)

[Claims] (1) A novel phenolic metal compound represented by (1) (in the formula, 1.- represents a H9α3 group). /, 3-di (
, 2-p-hydroxyphenyl-probyl)benzene〇 (support) phenol and general formula 俤) 俤) (b) and formula (2) (In each formula, R1, - represents a He-CH3 group ) in the presence of an acidic condensing agent at −1θ℃.
A method for producing a novel phenolic metal compound, which involves recovering a phenolic compound represented by the general formula () from a reaction mixture by reacting at a temperature of ~/θθ°C. 1,3-diisopropenylbenzene represented by the formula and 3-(-monohydro◆c-probyl)-
Isopropenylbenzene and the formula ← fathom −φ
/, J-di(-1roxy111probyl)benzene □ react with a compound selected from the group, and extract 7. from the reaction mixture.
/, J-di(
Method for producing co-p-hydroxyphenyl-propylene)benzene.