SU386918A1 - METHOD OF OBTAINING COMPLEX PENYLATING ETHERS OF PHYNYLOBOBENZOIC ACIDS - Google Patents

Description

one

The invention relates to the field of producing peroxide compounds containing an azo group, in particular, to a method for producing phenyl azobenzoic acid peroxide esters, which can be used to obtain colored polymers, for example polystyrenes, used in many industries.

A known method of producing peroxides, with a support of their azo group, by reacting p-fellilobenzoic acid chloride with peroxide atri in an acetone medium and isolating the symmetrical by-3- (3-phenylazobenzoyl) peroxide by known methods. This method allows to obtain a limited number of only high molecular weight symmetrical chromophore-containing peroxides, which are poorly soluble in monomers and have a high decomposition temperature.

The proposed method, using the well-known reaction, allows to obtain asymmetric chromophore-containing, not lower molecular weight peroxides, having a high solubility in monomers and a low decomposition temperature.

The proposed method for the preparation of new peroxides containing azo-group of peroxide esters of phenylazobenzoic acids is carried out by the interaction of phenyl azobenzoic acid chloride with hydroperoxide in a solvent at a temperature not exceeding 25 ° C in the presence of a hydrogen halide acceptor. Example 1. Synthesis of methyl perphenplasobenzoate.

In the reactor, equipped with a mechanical baffle, thermometer and addition funnel, put 1 g of methyl hydroperoxide in 40 ml of chloroform. Then, with vigorous stirring at a temperature of -10 ° C, 0.86 g of NaOH (40% solution) and 5 g of phenylazobe hydrochloride | Nzoic acid are simultaneously added. The reaction mixture is kept for 18 hours at room temperature. The precipitate is filtered off. The chloroform solution is washed with water until neutral, dried over sodium sulfate. The chloroform is removed in vacuo. The product is isolated. Yield 52%. The compound to be synthesized is red-orange powder, m.p. 108-109 ° C.

Calculated,%: C 65.62; H 5.86; N 10.52.

CuHl2N2O3

Found,%: C 65.40; H 5.90; N 10.12. Mol weight 240; a pier vespapd 256.

Example 2. Synthesis of treg-bugilperphenylazobenzo.

It is prepared as in Example 1 from 2 g of hydroperoxide g / 7 (g-butyl and 5 g of phenylazobenzoic acid chloral hydride in tetrachloride 3 carbon. Yield 58.3%. The substance is a red-orange powder, mp. Calculated,%: C 68.50; H 6.05; N 9.39. CnHisNaOs Found,%; C 68.79; H 6.65; N 9.19. 298; molar springy 280. Example 3. Synthesis of cumyl perphenylazo benzoate Obtained as in Example 1 from 2 g of cumene hydroperoxide and phenyl azobenzoic acid chloride in petroleum ether. Yield 41.4%. The product is a yellow powder, m.p. .70-72 ° C. 4 Calculations e, but,%: 73.30; H, 5.55; N, 7.78. C22H2iN2O3 Found,%: C, 72.85; H, 5.20; N, 7.60. Subject of isoretration. The method of obtaining the esters of hydrazyl benzoic acids, characterized in that chlorine. phenylazobenzoic acid anhydride is reacted with hydroperoxide in a solvent at a temperature not higher than 25 ° C in the presence of a hydrogen halide acceptor followed by release of the target product by known methods.