JPH09110764A - Method for producing bisalkylphenol compound - Google Patents

Abstract

(57) Abstract: A highly pure binuclear body (I) is produced in good yield by a simple method using 2,5-xylenol or 2,3,5-trimethylphenol as a raw material. In the formula, R represents hydrogen or methyl. SOLUTION: 2,5-xylenol or 2,3,5
-Trimethylphenol and formaldehyde 1: 1
The molar ratio of 0.1 to 0.5 is 0.1 to 0.4 with respect to 2,5-xylenol or 2,3,5-trimethylphenol.
Molar base catalyst and 5 to 20 relative to the base catalyst
The compound (I) is obtained by reacting at a temperature of 55 to 80 ° C. in the presence of a weight of water.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a bisalkylphenol compound useful as a raw material for a condensation reaction with a methylol compound, especially 2,5-xylenol or 2,3,3.
The present invention relates to a method for easily producing a binuclear body of 5-trimethylphenol with high purity.

[0002]

2. Description of the Related Art Methylol compounds are generally used as starting materials for dehydration condensation reaction because of their excellent reactivity. Various attempts have been made to synthesize a binuclear compound of a phenolic compound used for condensation with these methylol compounds. However, these 2
When producing the nucleolus, since the methylol body is also by-produced,
It was difficult to synthesize the binuclear body with high purity and high yield.

[0003]

DISCLOSURE OF THE INVENTION As a result of intensive studies, the present inventors have found that 2,5-xylenol or 2,3,5
With regard to trimethylphenol, it was found that binucleates can be obtained with high purity and high yield by selecting the reaction conditions, and the present invention has been completed. Therefore, the object of the present invention is 2,5-xylenol or 2,3,5-
It is to produce a high-purity bisalkylphenol compound with a high yield by a simple method using trimethylphenol as a raw material.

[0004]

Means for Solving the Problems That is, the present invention is
5-xylenol or 2,3,5-trimethylphenol and formaldehyde in a molar ratio of 1: 0.1 to 0.5 with respect to 2,5-xylenol or 2,3,5-trimethylphenol is 0.1. By reacting at a temperature of 55 to 80 ° C. in the presence of ˜0.4 mol times of the base catalyst and 5 to 20 times by weight of water of the base catalyst.

[0005]

The present invention provides a method for producing a bisalkylphenol compound represented by the formula (wherein R represents hydrogen or methyl).

[0007]

DETAILED DESCRIPTION OF THE INVENTION The reaction of 2,5-xylenol or 2,3,5-trimethylphenol with formaldehyde according to the present invention is carried out using 2,5-xylenol or 2,5-xylenol.
The molar ratio of 3,5-trimethylphenol to formaldehyde is in the range of 0.1-0.5, and is 0.1 with respect to 2,5-xylenol or 2,3,5-trimethylphenol.
To 0.4 to 40 moles of base catalyst and 5 to 20 weight of water relative to the base catalyst.
It is performed at a temperature in the range of ° C. The molar ratio of 2,5-xylenol or 2,3,5-trimethylphenol to formaldehyde is 1: 0.2 to 0.4, and further 1: 0.3 to.
A range of 0.4 is more preferred.

The base catalyst is preferably an alkali metal hydroxide, such as sodium hydroxide or potassium hydroxide. Among them, sodium hydroxide is preferably used. The base catalyst is 0.1-based on 2,5-xylenol or 2,3,5-trimethylphenol.
It is used in a range of 0.4 mol times, preferably 0.2 to
It is used in an amount of 0.3 mol times, and more preferably 0.25 to 0.3 mol times.

This reaction is carried out using water as a solvent, and water is
It is used in the range of 5 to 20 times the weight of the base catalyst.
This reaction is based on 2,5-xylenol or 2,3,5-
It is preferable to proceed while adding formaldehyde to a system in which trimethylphenol, a base catalyst and water are present. In this case, formaldehyde is usually used in the form of an aqueous solution, although not particularly limited thereto. Therefore, the amount of water needs to be achieved at least in the initial stage of the reaction, but it is preferable that the amount of water is within the above range even in the final stage of the reaction. Water is preferably present in an amount of 5 to 19 times by weight, particularly 7 to 12 times by weight, relative to the base catalyst, at least in the initial stage of the reaction. This reaction is 55-8
0 ° C., preferably 60 to 80 ° C., more preferably 70
It is carried out at a temperature of ~ 75 ° C.

In this reaction, by using 2,5-xylenol, a compound in which R in the formula (I) is hydrogen, that is, 4,4'-methylenebis (2,5-dimethylphenol) is produced. . Further, by using 2,3,5-trimethylphenol, a compound in which R in the formula (I) is methyl, that is, 4,4′-methylenebis (2,3,5-trimethylphenol) is produced. .

After the completion of the reaction, the desired bisalkylphenol compound can be taken out by performing an arbitrary operation. For example, the target bisalkylphenol compound can be deposited by acid precipitation from the reaction mass. In addition, after that, it is extracted with a good solvent such as methyl isobutyl ketone, the extract is concentrated if necessary, and then a poor solvent such as toluene is added and stirred to precipitate the target bisalkylphenol compound. Can be made.

The bisalkylphenol compound of formula (I) thus obtained can be advantageously used in the condensation reaction with a methylol compound.

[0013]

EXAMPLES Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples. The percentages given in the examples are by weight unless otherwise stated.

Example 1 735.2 g of 2,5-xylenol, 6 of sodium hydroxide
0 g and 540 g of water were charged into a 2-liter four-necked flask, and 37% formalin 16 was added while stirring at 60 ° C.
2.2 g was added dropwise over 2 hours and 30 minutes, and the reaction was continued at the same temperature for 4 hours. After completion of the reaction, 172 g of 36% hydrochloric acid was charged and subjected to acid precipitation, then extracted with methyl isobutyl ketone, washed with water and concentrated. To this, 500 g of toluene was added, and the mixture was stirred at room temperature for 2 hours and then filtered. The obtained solid content was purified with a toluene / ethyl acetate solvent system to obtain 253.5 g of 4,4'-methylenebis (2,5-dimethylphenol) (purity of 96% by liquid chromatography). Formaldehyde-based yield 47.5
%.

Mass spectrometry: FD-MS 256 ¹ H-NMR (acetone) δ (ppm): 2.08 (s, 6H);
2.12 (s, 6H); 3.67 (s, 2H); 6.59 (s, 2H); 6.66 (s,
2H); 7.80 (s, 2H).

Example 2 Instead of 2,5-xylenol in Example 1, 2,
The same operation as in Example 1 was carried out except that 817.3 g of 3,5-trimethylphenol was used, and 273.5 g of 4,4′-methylenebis (2,3,5-trimethylphenol).
(Purity of 95% by liquid chromatography) was obtained.
Yield 45.7% based on formaldehyde.

[0017] Mass ^{spectrometry: FD-MS 284 1 H-} NMR ( acetone) δ (ppm): 2.08 ( s, 6H);
2.12 (s, 6H); 2.21 (s, 6H); 3.96 (s, 2H); 6.51 (s,
2H); 7.55 (s, 2H).

[0018]

EFFECTS OF THE INVENTION According to the present invention, 2,5
It is possible to produce a binuclear compound of -xylenol or 2,3,5-trimethylphenol with a high purity, for example, a purity of 95% or more, and a high yield. The binuclear compound thus obtained is useful as a starting material for a condensation reaction.

Claims (3)

[Claims] 1. 2,5-xylenol or 2,3,5-
Trimethylphenol and formaldehyde 1: 0.1
2,5-xylenol or 2, at a molar ratio of ~ 0.5.
The reaction is carried out at a temperature of 55 to 80 ° C. in the presence of 0.1 to 0.4 mol of a base catalyst to 3,5-trimethylphenol and 5 to 20 weight of water of the base catalyst. Formula (I), characterized in that (In the formula, R represents hydrogen or methyl) A method for producing a bisalkylphenol compound. 2. Using 2,5-xylenol, 4,4'-
The method of claim 1, wherein methylenebis (2,5-dimethylphenol) is produced. 3. The method according to claim 1, wherein 4,4'-methylenebis (2,3,5-trimethylphenol) is produced using 2,3,5-trimethylphenol.