SU373272A1 - Method of producing cyclic aliphatic diepoxides - Google Patents

Description

one

The invention relates to a process for preparing cycloaliphatic diapoxides, which are widely used for the production of electrical insulating materials and bonding for glass-reinforced plastics.

A known method for the preparation of cycloaliphatic diionic oxides by the oxidation with anhydrous peracetic acid of the product of the interaction of cyclopentadiene with acrolein. The epoxidation process is long - 18-20 hours; the output of the diepoxide is low-54.4% (for the aldehyde introduced into the reaction); raw materials difficult to access.

In order to completely eliminate these drawbacks, it is proposed to epoxidize, for example, 30-60% aqueous solution of peracetic acid, complex compounds of unsaturated cyclic aldehydes with aluminum isopropylate. The epoxidation duration is 4-5 hours, the yield of the target product is 69%.

The proposed method allows to obtain the desired products from available raw materials, in high yield with a short epoxidation time. In addition, the use of aqueous solutions (30-60%) by nadusspoy acid simplifies the isolation of diepoxides and ensures the safe conduct of the process.

Example 1- Preparation of 3,4-enoxycyclohexylmethyl-3, 4-epoxycyclohexanecarboxylate.

To 220 g of tetrahydrobenzaldehyde in 100 ml of benzene is added with stirring

at a temperature of 40-45 ° C for 0.5-1.0 hours a solution of 12.2 g of aluminum isopropylate in 50 ml of benzene. After adding the total amount of benzene solution of aluminum isopropylate, the reaction mass is maintained at the same temperature for another hour. Then, 23 g of anhydrous sodium acetate is added to the reaction mass, cooled to 30 ° C, and with a strong displacement and cooling with running water, add

for 0.5-1 hours at 30-35 ° C, 460 g of 40% aqueous peracetic acid. After adding the entire amount of the peracid, the reaction mass is maintained at a temperature of 30-35 ° C for 3 more

hour. It is then cooled to room temperature, the lower aqueous layer is separated, and the benzene solution is washed with a 10% sodium carbonate solution and water. Benzene and other volatile products are distilled off at a temperature of 100-150 ° C and a residual pressure of 50-20 mm Hg. Art., gradually increasing towards the end of the distillation the degree of heating and the depth of the rarefaction. Receive 206.6 g (82% of theoretical)

colorless mobile liquid with t.

205--207 ° (10 mm Hg. Art.); 1.4940; d 1.16; viscosity at 320 spz.

Found: epoxy number 33.40; iodine number is 8.45.

Ci4H9o04.

Calculated: enoxide number 33.60; iodine number is missing.

Example 2. Preparation of 3,4-enoxy-6-methylcyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylate.

Under the conditions of irimer 1, a complex compound is obtained from 115.5 g (0.93 mol) of 6-methyltetrahydrobenzaldehyde in 50 liters of benzene and 5.5 g of aluminum isolate in 20 ml of benzene, which is epoxidized with 215 g of 40% oacetic acid in the presence of 10.4 g of anhydrous sodium acetate. Processing is similar to the previous example. This gives 116.4 g (81.5% of the theoretical) of a colorless transparent viscous liquid with a boiling point of 215-220 ° (5 mmHg); “L25 1.4960; 1.12; viscosity at 25 ° С 1780 spz.

Found: epoxy number 30,00; iodine number is 8.05.

CicHssO.

Calculated: epoxy number of 30.7; iodine number is missing.

Example 3. Preparation of 3,4-epoxy endomethylenocyclohexylmethyl-3, 4-epoxy-epoxy with ilencyclohexanecarboxylate.

Under the conditions of Example 1, a complex compound is obtained from 122 g (1 mol) of endomethylene tetrahydrobenzaldehyde in 50 ml of benzene and

6 g of aluminum isopropoxide in 20 ml of benzene, which is epoxidized with 186 g of 45% peracetic acid in the presence of 9.3 g of anhydrous sodium acetate - Treatment is similar to the previous example. Obtain 93 g (69%

from theoretical), after recrystallization from benzene and hexane, a white product, so pl. 141.5 ° C (according to literary data, mp. 143 ° C).

subject matter

Claims (1)

1. A method of producing cycloaliphatic diepoxides using peracetic acid as the oxidizing agent followed by isolating the target product with known techniques, characterized in that in order to increase the yield of the target product and simplify the technology, the complex connection of unsaturated cyclic aldehydes with aluminum alcohols is epoxidized, for example aluminum isopropylate. 2- The method of claim 1, wherein an aqueous solution of peracetic acid of 30-60% concentration is used.