SU487055A1 - Method for producing 1,3,6-trichloroadamantane - Google Patents

Description

The invention relates to a method for producing 1,3,6-trichloroadamantane used in the synthesis of heat-resistant polymers, lubricating oils and pharmaceuticals.

A known method for producing 1,3,6-trichloroadamantane by chlorination of adamantane with chlorosulfonic acid, taken in 6.5-7.5-fold weight excess, at 15-25 ° C for 150-200 hour, followed by extraction and chromatography. The yield of the target product is 70%.

The disadvantages of this method are the long duration of the process, the low conversion rate of the expensive chlorosulfonic acid, and the large amount of wastewater (6.7 parts by weight per 1 part by weight of the desired compound).

In order to intensify and simplify the process, it is proposed that adamantane be treated with a mixture of SOo and Clg gases at a temperature not higher than 30 ° C in an inert organic solvent medium followed by thermal decomposition of sulfonochlorination intermediate products at 110-180 ° C in an inert organic solvent and isolation of the target product by known methods .

Sulfonation takes place at room temperature for - 30-45 minutes in the absence of initiators with a 100% conversion of adamantane.

During the thermal decomposition of the obtained mixture of products for 3-6 hours, 1,3,6-trichlororadantane is formed with the release of

o vo.

The process is carried out in any inert organic solvent both at the sulfochlorination stage of adamantane and at the stage of thermal decomposition of intermediate products.

The process can be carried out in the medium of the same solvent, for example, toluene or lx-xylene, in the same reactor without isolation of the intermediate products of sulfochlorination.

With such a reaction, the time of the process is reduced by a factor of 30-50, the stage of separation of the target product is simplified, wastewater is eliminated, and available SO2 and Cb are used with almost quantitative transformation of the latter.

Example. A solution of 5 g of adamantane is charged into a reactor equipped with a thermometer, a reflux condenser, and a bubbler.

80 ml of carbon tetrachloride and pass the mixture of SO with stirring; and CU (0.5 and 0.3 g / min, respectively) for 30 minutes at 30 ° C. After removal of the solvent, 14.7 g of adamantane conversion products are obtained.

Found,%; S 15.0; C1 total 32.5; SM washed. 9.2.

In the same reactor load 75 ml of l-xylene (without sulfur compounds) and the resulting solution is heated for 6 hours at 142 ° C. After removing xylene in vacuo, 7.9 g of raw material are obtained, which is recrystallized from petroleum ether, and 6 g (68%) of 1,3,6-trichloroadamantane are isolated, m.p. 148-150 ° C (ethyl alcohol).

Found,%: C1 43.3; 44.6; S footprints.

CioHiaClsCalculated,%: C1 44.6.

However, the thermal decomposition of sulfochlorination products can be carried out without their isolation in the same reactor with the addition of xylene and simultaneous trapping of carbon tetrachloride or in a single solvent, for example toluene or xylene.

Claims (1)

Invention Formula The method of producing 1,3,6-trichlororadantane based on adamantane, characterized in that, in order to intensify and simplify the process, adamantane is treated with a mixture of gases SOg and CH at a temperature not exceeding 30 ° C in an inert organic solvent followed by thermal decomposition of intermediate products sulfonation at PO-180 ° C in an inert organic solvent and isolation of the target product by known methods.