The way to obtain 3,5-di-tert-butyl-4-oxybenzaldehyde


C07C47/56 - containing hydroxy groups

 

(57) Abstract:

The invention relates to petrochemistry, in particular, to a method for producing 3,5-decret-butyl-4-oxybenzaldehyde (DBA) used as an intermediate product to obtain pesticides, stabilizers for polymeric materials and petroleum products. The purpose of the invention is to increase the output of DBA, the simplification of the process. The objective is achieved by conducting the condensation of 2,6-decret-butylphenol with urotropine in a molar ratio of 1 : 0.8 to 1.5 in an environment of 90 % acetic acid with a mass ratio of acetic acid : : 2,6-decret-butylphenol 1 : 2,5 to 3,2. The yield of TBA increases to 95 %. Reuse of acetic acid does not reduce the yield of the target product. table 1.

The invention relates to petrochemistry, in particular, to a method for producing 3,5-decret-butyl-4-oxybenzaldehyde (DBA) used as an intermediate product to obtain pesticides, stabilizers for polymeric materials and products.

A method of obtaining formirovanie 2,6-decret-butylphenol ( 2,6-DTBP) urotropine in triperoxonane acid. The yield of the desired product 60 wt.

The disadvantages of this method are the low yield of the target packaging 2,6-ditertbutyl with hexamethylenetetramine in the presence of boric acid [2] Synthesis of lead in the environment of ethylene glycol at a temperature of 150oWith subsequent dosage 30 sulfuric acid. The output 94

The disadvantage of this method is the use of high temperatures, aqueous acid solution, the need for wastewater.

The closest in technical essence to the proposed method is the method of obtaining TBA formirovanie 2,6-decret-butylphenol with urotropine, when the molar ratio 1 2.0 to 3.0, respectively, in the environment 75-80 acetic acid [3]

The process is executed first when the 38oAnd after adding water the temperature was raised to 93oC. the Reaction mixture is boiled for 1 h and then evaporated and cooled. The target product was filtered and dried on the vacuum filter. The output DBA 90 melting point 187-189oC.

The main disadvantage of the prototype relatively low output TBA, large amounts of sewage.

The aim of the invention is to increase the output of DBA, the simplification of the process, reducing the amount of wastewater.

This goal is achieved by bringing the condensation of 2,6-decret-butylphenol with urotropine in a molar ratio of 1 0,8-1,5 environment 90 acetic acid, with a mass ratio of acetic acid 2,6-decret-butylphenol, equal to 1 to 2.5 to 3.2. The yield of TBA tx2">

The process is as follows. In a round bottom flask, equipped with reflux condenser, thermometer, load 1 mol 2,6-decret-butylphenol, of 0.8 to 1.5 mole of hexamine and 2.5 -3,2 from 2,6-DTBP acetic acid. The reaction mixture is boiled until precipitation of white crystals. Next is cooled, the precipitated crystals filtered off, washed with acetic acid and dried on vakuumfiltre. The yield of the target product is 94-95 wt. Source reagents must meet the following requirements:

1) hexamethylenetetramine THE 6-09-09-353-74;

2) 2,6-decret-butylphenol receive A. S. N 632681;

3) acetic acid GOST 61-75.

Example 1. In a round bottom flask, equipped with reflux condenser, thermometer, load of 5.2 g (0.025 m) of 2,6-decret-butylphenol, 2,62 g (0.02 m) urotropine, 13 90 ml of acetic acid. The reaction mixture is boiled until precipitation of white crystals. Cool, the precipitated crystals filtered off, washed with acetic acid and dried on the vacuum filter. Get 5,61 g (95%) of 3,5-decret-butyl-4-hydroxy-benzaldehyde with a melting point 189oWith [U.S. Pat. USA N 3833660, Tmelt. 187-189°C] the infrared spectrum, cm-1; 3433 (0-H), 1665 (C=0).

Example 2. In a round bottom flask, equipped with reflux condenser, thermometer, seleccionou the mixture boil until a drop of white crystals, cool, the crystals are filtered, washed with acetic acid and dried. Get of 5.55 g (94,1) 3,5-decret-butyl-4-hydroxy-benzaldehyde, melting point 188-189oC.

Example 3. 3,5-Decret-butyl-4-hydroxy-benzaldehyde was prepared as in example 1. Using 13 ml of acetic acid from the filtrate of example 2. Gain of 5.4 g (91,5 ) 3,5-decret-butyl-4-hydroxy-benzaldehyde, melting point 185-187oC.

Example 4. 3,5-Decret-butyl-4-hydroxy-benzaldehyde was prepared as in example 1. Using 13 ml of acetic acid from the filtrate of example 3. Get 5,2 g (88,1 ), 3,5-decret-butyl-4-hydroxy-benzaldehyde, melting point 183-185oC.

Examples 5-13. Vary the molar mass ratio of ingredients. The obtained yields of the target product are indicated in the table properties of the obtained product are fully consistent with the compound obtained according to example 1).

As can be seen from the table, modifying the proposed conditions leads to a decrease of the yield of the target product.

Thus, the inventive method compared to the prototype is characterized by a higher yield of the target product and the simplicity of the process design.

The way to obtain 3,5-decret-butyl-4-oxybenzaldehyde condensational aqueous solution of acetic acid 90% concentration and condensation is carried out at a mass ratio of 2,6-decret-butylphenol acetic acid 1:2.5 to 3.2 and a molar ratio of 2,6-decret-butylphenol methenamine 1:0,8-1,5.

 

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