Method for preparing β-(4-hydroxy-3.5-di-tertiary-butylphenyl)-propionic acid esters

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to a method for preparing β-(4-hydroxy-3,5-di-tert.-butylphenyl)-propionic acid esters that are used in industry of polymers as stabilizing agents. Method involves carrying out the process of the ester interchange reaction of β-(4-hydroxy-3,5-di-tert.-butylphenyl)-propionic acid methyl ester with polyhydric alcohols in inert gas flow at enhanced temperatures (130-190°C in the presence of the following components, wt.-%: 2,6-di-tert.-butylphenolate sodium, 1.5-3.6; 4-(β-methylcaboxyethyl)-2,6-di-tert.-butylphenolate sodium, 4.0-8.6; sodium acrylate, 2.1-6.4; 2,6-di-tert.-butylphenol, the balance. Indicated compounds of alkaline metal are used in the amount 0.4-5.1 wt.-% of the amount of β-(4-hydroxy-3,5-di-tert.-butylphenyl)-propionic acid methyl ester as measure for the sum of 4-(β-methylcarboxyethyl)-2,6-di-tert.-butylphenolate sodium, alkaline metal 2,6-di-tert.-butylphenolate and sodium acrylate. Invention provides increasing yield of the end product and its enhanced quality.

EFFECT: improved preparing method.

2 cl, 1 tbl, 10 ex

 

The invention relates to organic chemistry, specifically to the production of esters β-(4-hydroxy-3,5-di-tert-butylphenyl)propionic acid, which are used in the polymer industry as stabilizers.

A method of obtaining esters β-(4-hydroxy-3,5-di-tert-butylphenyl)propionic acid by transesterification of methyl ester β-(4-hydroxy-3,5-di-tert-butylphenyl)propionic acid (metiloksi) polynuclear alcohols at a temperature of 130-190°C for 6-12 hours in the presence of a catalyst of dibutyltindilaurate and oxide dibutyrate [U.S. Patent No. 4618700 from 21.10.86,].

The disadvantages of this method are the high cost and high toxicity of the used catalyst.

A method of obtaining esters β-(4-hydroxy-3,5-di-tert-butylphenyl)propionic acid using as a catalyst lithium amide and lithium hydride [U.S. Patent No. 4618700 from 21.10.86,].

The disadvantage of this method is the use of scarce and explosion-fire catalyst.

A method of obtaining pentaerythrol-tetrakis-[3-(4-hydroxy-3,5-di-tert-butylphenyl)propionate], consisting in the interesterification of metiloksi pentaerythritol in the presence of the solvent of dimethylformamide or dimethyl sulfoxide and the catalyst is zinc acetate [Application No. 2002132169/04 to the patent of the Russian Federation dated 28.12.2002].

The disadvantage of this method is its high cost due to the use of significant quantities of solvent and the instability of the catalyst which decomposes at elevated temperatures.

A method of obtaining methyl ester β-(4-hydroxy-3,5-di-tert-butylphenyl)propionic acid by alkylation of 2,6-ditertbutyl methyl acrylate at an elevated temperature using a catalytic complex of the following composition, % wt.: 2,6-di-tert-butylphenol sodium 1,4-11,0; β-(4-hydroxy-3,5-di-tert-butylphenyl)propionate sodium 0,4-3,0; 2,6-di-tert-butylphenol else [RF Patent №2178408, IPC C 07 C 69/732 issued 20.12.2002].

The disadvantages of the above method include the formation of by-product -β-(4-hydroxy-3,5-di-tert-butylphenyl)propionic acid as a result of using the catalyst composition β-(4-hydroxy-3,5-di-tert-butylphenyl)propionate sodium, which gives a yellow-cream color of the target product.

The closest technical solution (prototype) is a method of obtaining esters β-(4-hydroxy-3,5-di-tert-butylphenyl)propionic acid in the process of interesterification methyl ester β-(4-hydroxy-3,5-di-tert-butylphenyl)propionic acid polynuclear alcohols at 135-180°With the current of inert gas in the presence of a catalyst of the following composition, % by weight: 4-(β -methylcarbamate)-2,6-di-tert-butylphenol sodium 22,8-12, 0mm; 2,6-di-tert-butylphenol potassium of 5.1-1,8; 2,6-di-tert-butylphenol else [A.S. No. 1685920, IPC C 07 C 69/732, 67/02].

These compounds of alkali metals are used in quantities of 1.5 to 10.0 mol.% from methyl ester β-(4-hydroxy-3,5-di-tert-butylphenyl)propionic acid.

The disadvantage of this method is the relatively low yield of the target product, which does not exceed 94%.

The technical problem whose solution is proposed in the present invention is to develop a method of producing esters β-(4-hydroxy-3,5-di-tert-butylphenyl)propionic acid, characterized by low quantity of generated by-products and increase the yield of the target product.

This task is solved in that in the production method of esters β-(4-hydroxy-3,5-di-tert-butylphenyl)propionic acid by transesterification of the methyl ester β-(4-hydroxy-3,5-di-tert-butylphenyl)propionic acid polynuclear alcohols in a current of inert gas and at an elevated temperature in the presence of 2,6-di-tert-butylphenol alkali metal, 4-(β-methylcarbamate)-2,6-di-tert-butylphenol sodium and 2,4-di-tert-butylphenol as a catalyst, according to the invention using the catalyst additionally containing sodium acrylate when the next CEO is wearing components, % mass: 2,6-di-tert-butylphenol sodium 1,5-3,6; 4-(β-methylcarbamate)-2,6-di-tert-butylphenol sodium 4,0-8,6; sodium acrylate 2,1-6,4; 2,6-di-tert-butylphenol else.

These compounds of an alkali metal is used in an amount of 0.4 to 5.1 mol.% from methyl ester β-(4-hydroxy-3,5-di-tert-butylphenyl)propionic acid, calculated on the amount of 4-(β-methylcarbamate)-2,6-di-tert-butylphenol sodium 2,6-di-tert-butylphenol alkaline sodium metal and sodium acrylate, at the same time as 2,6-di-tert-butylphenol alkali metal use of 2,6-di-tert-butylphenol sodium, and the process of interesterification is carried out at a temperature of 130-190°.

The method is as follows.

Esters β-(4-hydroxy-3,5-di-tert-butylphenyl)propionic acid is separated from salts β-(4-hydroxy-3,5-di-tert-butylphenyl)propionic acid and purified by crystallization.

The catalyst is prepared either by mixing the individual components or by heating the sodium hydroxide with 2,6-di-tert-butylphenol in the environment of methanol in a stream of nitrogen at a temperature of 80-100°for 0.2-0.5 hours followed by distillation of methanol and water. Then the mixture was added the estimated number of methyl acrylate, necessary for the formation of methyl ester β-(4-hydroxy-3,5-di-tert-butylphenyl)propionic acid, and incubated for 40-60minutes. This results in the catalytic complex of the following composition: 2,6-di-tert-butylphenol sodium 4-(β-methylcarbamate)-2,6-di-tert-butylphenol sodium, sodium acrylate, 2,6-di-tert-butylphenol.

An unexpected effect of the proposed method was the fact that in the initial moment of time NaOH interacts with 2,6-di-tert-butylphenol with the formation of 2,6-di-tert-butylphenol sodium. 20-30 minutes at a temperature of 70-90°enters the reaction is not more than 60% NaOH. Further education 2,6-di-tert-butylphenol sodium does not affect the reaction rate, but worsens the chromaticity of the target product. With the introduction of the methyl acrylate is education β-(4-hydroxy-3,5-di-tert-butylphenyl)of sodium propionate and sodium acrylate as a result of interaction NaOH residues with methyl acrylate. The formation of sodium acrylate is due to a stronger acid properties of methyl acrylate, compared with 2,6-di-tert-butylphenol, which allows to constrain further the education of 2,6-di-tert-butylphenol sodium and activate the catalytic complex.

Source reagents must meet the following requirements:

- NaOH - GOST 4328-77;

- 2,6-di-tert-butylphenol - TU 38.103375-80;

- methanol - GOST 2222-78;

- MMA - GOST 2971-86;

- pentaerythritol - GOST 2168-82.

To the obtained catalyst type layer is hydrated ether β -(4-hydroxy-3,5-di-tert-butylphenyl)propionic acid, the mixture is kept for 30-40 minutes and then add polynuclear alcohol, in a stream of inert gas, the mixture is heated for 3.5-5 hours at a temperature of 130-190°With reflux condenser, are dougong under vacuum. The reaction mass is gradually cooled to 100°dissolve in hydrocarbon solution and cooled to 10-15°C. After the deposition of crystals is filtered.

Example 1.

In a three-neck reaction flask equipped with stirrer and input for inert gas load 30,95 grams (0.15% wt.) 2,6-di-tert-butylphenol, 0.5 g (0,014% wt.) of sodium hydroxide, in a stream of nitrogen (argon) and heated to 95°and withstand 50-60 minutes with distillation of the water-methanol mixture. Then the flask makes fun 1,72 g (0,02% wt.) of methyl acrylate at a temperature of 110°C for 30-40 minutes. The result is 33,15 g catalytic complex whose composition and the content of alkali components is confirmed by potentiometric titration and liquid chromatography. Next, to the obtained catalyst was added dropwise 11,18 g of methyl acrylate, stand 30 minutes and then added to 5.1 g of pentaerythritol. In a stream of inert gas, the mixture is heated for 3.5 hours at 150°With a reflux condenser, catching during the reaction of methyl alcohol in the condenser, and 20-30 minutes are dougong under vacuum. The reaction m is cel gradually cooled to 100° C, dissolved in a hydrocarbon solvent (or spirit-hydrocarbon) and cooled to 10°C. After precipitation of the crystals filtered off. Output pentaerythrol-tetrakis-β-(4-hydroxy-3,5-di-tert-butylphenyl)propionate of 47.8 g (98,95%), melting point 116-117°C.

The results of the syntheses with other alcohols and compounds catalytic complex are shown in table 1, the syntheses carried out analogously to example 1.

The table shows that the proposed method will allow you to reach exit esters β-(4-hydroxy-3,5-di-tert-butylphenyl)propionic acid of 99.5% compared to the prototype, where the output reaches 94%, which make wide use as stabilizers in the polymer industry.

and 88.8
Table 1.
ExampleThe catalyst composition, wt.%The amount of catalyst to the amount of compounds of alkali metals, mol. %Time, hPolynuclear alcoholOutput %Get the connectionMelting point, °
ArONasodium acrylatePhONaPhOH
2of 5.4a 3.91,5 89,24,705,0pentaerythrit98,6pentaerythrol-tetrakis[β-(4-hydroxy-3,5-di-tert-butylphenyl)propionate]116-117
36,13,32,388,34,554,5diethylene glycolof 99.1diethylene glycol-bis[β-(4-hydroxy-3,5-di-tert-butylphenyl)propionate]92-93
47,94,61,785,84,105,0thiodiethanol99,0thiodiethanol-bis[β-(4-hydroxy-3,5-di-tert-butylphenyl)propionate]71
58,24,02,885,03,604,2triethylene glycol99,2ethyl-1,1,1-Tris[methylene-β-(4-hydroxy-3,5-di-tert-butylphenyl)propionate]107-108
68,43,13,684,92,905,1the pentaerythritol98,5pentaerythrol-tetrakis[β-(4-hydroxy-3,5-di-tert-butylphenyl)propionate]116-117
7a 4.93,23,10,456,0diethylene glycol98,4diethylenglycol[β-(4-hydroxy-3,5-di-tert-butylphenyl)propionate]92-93
87,14,83,484,75,104,8triethylene glycol99,5ethyl-1,1,1-Tris[methylene-β-(4-hydroxy-3,5-di-tert-butylphenyl)propionate]107-108
96,82,33,087,94,65,3thiodiethanolof 99.1thiodiethanol-bis[β-(4-hydroxy-3,5-di-tert-butylphenyl)propionate]71
106,55,32,885,4a 3.95,1diethylene glycol99,0diethylene glycol-bis[β-(4-hydroxy-3,5-di-tert-butylphenyl)propionate]92-93
Note: ArONa - 4-(β-methylcarbamate)-2,6-di-tert-butylphenol sodium;

PhOH - 2,6-di-tert-butylphenol; PhONa - 2,6-di-tert-butylphenol sodium.

1. The method of obtaining esters β-(4-hydroxy-3,5-di-tert-butylphenyl)propionic acid by transesterification of the methyl ester β-(4-g is droxi-3,5-di-tert-butylphenyl)propionic acid polynuclear alcohols in a current of inert gas and at an elevated temperature in the presence of 2,6-di-tert-butylphenol alkali metal, 4-(β-methylcarbamate)-2,6-di-tert-butylphenol sodium and 2,6-di-tert-butylphenol as a catalyst, characterized in that the used catalyst, optionally containing sodium acrylate in the following ratio, wt.%:

2,6-di-tert-Butylphenol alkali metal 1,5-3,6

4-(β-Methylcarbamate)-2,6-di-tert-butylphenol sodium 4,0-8,6

Sodium acrylate 2,1-6,4

2,6-di-tert-butylphenol Else

the compounds of the alkaline metal is used in an amount of 0.4 to 5.1 wt.% from methyl ester β-(4-hydroxy-3,5-di-tert-butylphenyl)propionic acid, calculated on the amount of 4-(β-methylcarbamate)-2,6-di-tert-butylphenol sodium 2,6-di-tert-butylphenol alkali metal and sodium acrylate.

2. The method according to claim 1, characterized in that as 2,6-di-tert-butylphenol alkali metal use of 2,6-di-tert-butylphenol sodium, and the process of interesterification is carried out at a temperature of 130-190°C.



 

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