SU1754706A1 - 2-(n,n-dimethylamino)-heptachloronaphthalene as an initial substance for synthesis of perfluoro-2-(n,n-dimethylamino)-decalin, and a method of its synthesis - Google Patents

Abstract

The invention relates to automatic amines, in particular to 2- {M, M-dimethylamino) heptachloronaphthalene (I) as an intermediate for the synthesis of perfluoro-2- (M, M-dimethylamino) decalin dielectric, as well as to compounds I. The invention can be used & chemical industry. The goal is to search for new, more affordable and cheaper intermediates for synthesis, as well as to develop a method for producing compounds I. Synthesis is carried out by heating octachloronaphthalene in NN-dimethylformamide in the presence of copper oxide at a molar ratio of reagents 5: (80 ± 15) :( 1 ± 0, 2) at 70-100 ° C. These conditions allow to obtain the target product with the release of 73-E CgNbO; m.p. 223-225 ° C. “Yo

Description

The invention relates to polychloromatic compounds and relates to a new chemical compound, 2- (M, M-dimethylamino) heptachloronaphthalene, which can be used to synthesize perfluoro-2- {M, M-dimethylamino) decalin.

The purpose of the invention is to obtain a new compound in a series of polychloroaromatic compounds as a starting material for obtaining perfluoro-2- (M, L-dimethylamino) decalin, which allows for an increase in the yield of the latter, and a new method for its preparation.

The goal is achieved as follows. A solution of octachloronaphthalene in NN-dimethylformamide is heated to 70-100 ° C in the presence of copper (I) oxide, usually for 8-20 hours at a molar ratio of octachloronaphthalene M.M-dimethylformamide: copper oxide (I) 5: (80 ± 15): (1 ± 0.2) s

the subsequent isolation of the target product, for example, by precipitation from a water-alkaline solution.

The use of copper (I) oxide in this process makes it possible to obtain pure 2- (M, M-dimethylamino) heptachloronaphthalene in 88% yield, at a sufficiently high reaction rate, under relatively mild conditions, and with an insignificant formation of by-products. The conditions of the known methods do not permit the isolation of a pure product with a high yield.

PRI me R 1 Implementation of the synthesis of the target product.

A solution of 2 g (0.005 mol) of octachloronaphthalene in 25 ml (0.40 mol) of M, M-dimethylformamide is stirred at 90 ° C in the presence of 0.15 g of SodO for 10 hours. After cooling to room temperature, pe5

B

eight

CX

the stock mixture is filtered from an inorganic precipitate. The filtrate is mixed with 100 ml of a 2% NaOH solution, the precipitated precipitate is filtered, washed with water, dried in air, recrystallized from benzene and 1.79 g (0.004 mol) of 2- {M, M-dimethylamino) heptachlor-naphthalene is obtained. which is a yellow crystalline substance, m.p. 223-225 ° C. Yield 88%.

Physico-chemical data analysis.

UV-spectrum, A max (Ige), nm: 288 (4.62), 313 (4.10), 370 (3.68), 404 (3.58); in ethanol.

- IR spectrum, 795 sl, 865 sl, 960 sr, 1170 sr, 1245 s. 1290sl, 1405sr, 1530sr, 2800sr, 2925sr; in the tablet KBG.

Spectrum PMR, im.d .: 3,05s from TMS, N (CH3) 2; in the SS.

Found,%: C 34.96; H 0.14; CI 60.28; N 3 35.

Calculated,%: C 34.91; H 0.16; C, 60.24; N 3.39,

Mol mass 412.5 (mass spectrometrically), which corresponds to the gross formula of the compound CiaHeClvN and the structural formula

C C1 C1YSVN (CHb

ci Tsrct

C1 C1

20 ° C. The consumption of the substrate in the electrochemical fluorination is replenished by feeding its concentrated solution from the mixer, where it is preliminarily prepared.

Received 350 g of raw material, the composition of which according to GLC,%: perfluorodecalin 30.0; perfluoro-2- (M, M-di-methy l amino) dekaline 25.0; the remaining 45% is unidentified compounds (17 substances), the content of which varies in the range of 0.5-15%. After carrying out the rectification of the raw material at 187-188 ° C, perfluoro-2- (M.M-dimethylamino) decalin was isolated to yield

14%,

The advantage of the synthesis method using 2- (M, M-dimethylamino) heptahlornaphthalene is compared with that known to simplify the process, the availability of the starting octachloronaphthalene, its cheapness (5-7 rubles / kg) relative to

octafluorotnaftalene (500-1000 rubles / kg), not produced by domestic industry.

Claims (2)

Invention Formula 1. 2- {M, M-dimethylamino) -heptachloronaphthalene of formula C1 C1 С1УТЧЖСНз | 2 с1-ЦАуАс1 ci ct PRI mme R 2. Use of the desired product for the synthesis of perfluoro-2- (M, M-dimethylamino) decalin. A weighed 413 g (1 mol) of 2- (M, M-dimethylamino) heptachloronaphthalene and 1652 g (82.6 mol) of liquid hydrogen fluoride are loaded into a steel electrolyzer with nickel anodes and steel cathodes. Current load 10 A at a current density of 0.012 A / cm. The voltage at the electrodes, at the beginning of the process, is 5.5 and 6.3 V - at the end. The temperature of the electrolyte is within 16 as the starting material for the synthesis of perfluoro-2- (M, M-dimethylamino) decalin. 2. A method for the preparation of 2- (M, M-dimethylamino) -heptachloronaphthalene, excellently, so that the process is carried out by heating octachloronaphthalene in M, N-dimethylformamide in the presence of copper (I) oxide at molar ratio of 5; (80 ± 15) :( 1 ± 0.2), respectively, at 70-100 ° C.