SU327177A1 - METHOD FOR PRODUCING DIVINYL ETHER BIS - Google Patents

Description

The invention relates to a process for the preparation of new DIVINYL esters of bis (4-hydroxy-5-aminophenyl) alkanes, which can be used in the synthesis of polymers.

A known method for the preparation of vinyl esters of aminophenols by vinylating aminophenols with acetylene under pressure in the presence of an alkaline catalyst.

Using direct vinylation of bisorthoaminophenols with acetylene, divinyl esters of bis (4-hydroxy-5-aminophenyl) alkanes with two amino groups in the molecule are obtained, which possess more valuable properties than the known vinyl esters of aminophenols. So the copolymers and polymers based on the compounds obtained have enhanced adhesion properties and increased heat resistance.

The proposed method is that bisortoaminophenols of the general formula

NH2

NH2 Гх-СНг-, С (СЫЬЬ

Vinyl is acetylene at a pressure of 18-20 atm at a temperature not higher than in an aqueous-dioxane medium in the presence of an alkaline catalyst used in an amount of 2 mol per 1 mol of bisorthophenol.

Water in an amount of 50-100% by weight of bisorthoaminophenol is introduced into the reaction mixture, due to which the resinification of the reaction products is reduced and the yield of divinyl esters is increased.

The resulting esters are thick, ointment-like transparent yellow-brown substances.

Example 1. 16.3 g (0.05 mol) of bis- (3-methyl-4-hydroxy-5-aminophenyl) -cyclohexane-1, 5.6 g (0.1 mol) of KOH, 250 ml of dioxane, 8 A ml of water (50% by weight of bisorthoaminophenol) is loaded into a rotating autoclave. Reactionary

the mixture is saturated with acetylene to 18-20 atm. The reaction temperature is 160 ° C, time 1 hour. After cooling, the reaction mixture is discharged with caustic alkali. Dioxane is distilled off in vacuum at a pressure of 10-20 mm Hg. Art.

Divinyl ether was isolated by vacuum fractional distillation from a Favorsky flask. The yield of bis (3-methyl-4-hydroxy-5-aminophenyl) -cy divinyl ester, clohexane-1 4 g (21.1% of the theoretical), t. Bales. 185-190С (I mm

Example 2. 35 g (0.13 mol) of bis- (4-hydroxy-aminophenyl) propane-2,2, 14.5 g (0.26 mol) KOH, 400 ml of dioxane, 35 ml of water (100% of weight of bisorthoaminophenol) is loaded into a rotating autoclave and saturated with acetylene to 18-20 atm. The reaction temperature is 170 ° C, the time is 3 hours. After cooling, the reaction mixture is discharged, dried with caustic alkali. Diokean is distilled off in vacuum at a residual pressure of 10-20 mm Hg. Art. Divinyl ether was isolated by vacuum fractional distillation from a Favorsky flask.

The yield of bis (4-hydroxy-5-aminophenyl) propane-2,2-divinyl ester is 2.2 10.2 g (24.3% of the theoretical), b.p. 210-212 ° C (0.5 mm

OL

Hg), at 1.5878.

Subject invention

Claims (2)

1. A process for the preparation of bis (4-hydroxy-5-aminophenyl) -alkanes divinyl esters, characterized in that a bisortoaminophenol of the formula where RH, CH3-, CrH sn: , Sbnu-cyclo c, n, treated with acetylene at a temperature not higher than 180 ° C, pressure of 15-20 atm in a water-dioxane medium in the presence of an alkaline catalyst with the release of the target product by known techniques. 2. The method according to claim 1, wherein the process is conducted in a water-dioxane medium with a water content of at least 50% of the starting bisorthoamino-phenol.