The method of obtaining dichloro-di-p-xylylene

IPC classes for russian patent The method of obtaining dichloro-di-p-xylylene (RU 2101272):

C07C25/18 - Polycyclic aromatic halogenated hydrocarbons

C07C17 - Compounds containing carbon and halogens with or without hydrogen

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(57) Abstract:

The invention relates to organic chemistry, in particular the production of intermediate for the synthesis of poly-n-xylylene used for surface treatment of metal parts in electronics. The method includes photochemical chlorination of 2-chloro-n-xylene at 160-170^oC, interaction of 2-chloro-n-xilinhaote with trimethylamine at 0-5^oC, thermal decomposition of 2-chloro-n-methylbenzenesulfonamide in a concentrated solution of alkali at 110-120^oC. the New method provides an increase in the yield of dichloro-di-n-xylylene while reducing the complexity of the process.

The invention relates to a method for producing dichloro-di-n-xylylene, which is an intermediate in the synthesis of poly-n-xylylene used for surface treatment of metal parts in electronics.

A method of obtaining chlorine - and bromine-di-n-xylylene gorodilova cyclic di-n-xylylene at 0-80^oC in the presence of a number of metals (Fe, B, Al, Zn, and others ) or their halides in an inert solvent (U.S. Pat. USA N 3221068, CL 260-649, publ. 1965). The process differs relatively low output, low selectivity, resulting in the generated target PR is whether the cleavage reaction according to Hoffman n-methylenedioxymethylamphetamine (or hydroxide) (Kardash I. E. and other Chemistry and application of poly-n-xylylene. In Proc. of the Results of science and technology, I. 19, M, 1984, S. 84). The reaction is carried out at 60-100^oC, the yield of the target product is 10% photolysis 2,11-dithio[3,3]-n-cyclophane leads to cyclo-di-n-xylylene with the release of 60% (ibid.). A similar result can also be achieved by photolysis of complex cyclic ethers. The lack of the latter methods is the unavailability of raw materials.

Closest to the proposed method is a method of obtaining dichloro-di-n-xylylene from 2-chloro-n-xylene (ed. St. Czechoslovakia 247592, class C 07 C 15/08, publ. 1998), carried out in several stages.

Photochemical chlorination of 2-chloro-n-xylene, with approximately 80^oC get 2-chloro-n-killgore (yield 45%), which then interacts with trimethylamine and 65% forms a Quaternary ammonium salt of (2-chloro-n-methylbenzeneethanamine). Passing through the ion-exchange resin Sol was transferred to ammonium base is allocated in the form of an aqueous solution (yield 85%). Hydroxide 2-chloro-n-methylbenzeneethanamine are subjected to thermal decomposition at approximately 8 o'clock Crystal dichloro-di-n-xylylene partially emit extraction with an organic solvent (toloo is the process of evaporation of the filtrate. The output of dichloro-di-n-xylylene at the stage of thermal splitting is 37% believing taken on ammonium base, the overall yield of the final product dichloro-di-n-xylylene, counting on the original 2-chloro-n-xylene, in this way amounted to 9.2%
The disadvantages of this method is the small output stage photochemical chlorination of 2-chloro-n-xylene (45%) and the interaction of 2-chloro-n-xilinhaote with trimethylamine (65%), as well as the duration and intensity stage of transformation of ammonium salt in dichloro-di-n-xylylene, including additional activation and regeneration of the resin and the allocation of the intermediate ammonium base.

Object of the invention is to increase the overall yield of the target product and reducing the complexity of the process.

The technology of the proposed method is as follows.

2-Chloro-n-xylene, obtained according to the method of n-xylene, is subjected to photochemical chlorination at 160-170^oC.

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You get 2-chloro-n-killgore allocated from the reaction mixture by distillation. The output is 78-84% of 2-Chloro-n-killgore in acetone interacts with trimethylamine at 0-5^oC, forming 2-chloro-n-methylbenzylamine is at 110-120^oC in concentrated alkali solution. Reaction time is 3-3,5 hours the Resulting precipitate of poly-n-xylylene is filtered off, washed with water, dried and from it is extracted with an organic solvent (toluene, alkylhalogenide) dichloro-di-n-xylylene. After removal of the solvent is crystallized finished product with mass fractions of the basic substance of 98.5-99.2% of the Output of dichloro-di-n-xylylene is 10-12% counting by 2-chloro-n-xylene.

Distinctive features of the proposed method are the following:
temperature photochemical chlorination of 2-chloro-n-xylene,
the temperature of the interaction of 2-chloro-n-xilinhaote with trimethylamine,
thermal decomposition of 2-chloro-n-methylbenzenesulfonamide in a concentrated solution of alkali at 110-120^oC.

Distinctive features are new and do not follow from the prior art.

The essential features of the invention enables the achievement of a new technical result: increased product yield by reducing the complexity of the process.

Example 1. 2-Chloro-n-xylene is produced by chlorination in the core by a known method.

3-necked flask, equipped with reflux condenser, thermometer and the PRS drained conc. H₂SO₄with a speed of 28 g/h of the Released gaseous HCl absorb 15% NaOH solution. After absorbing 63 g of chlorine, the mixture is cooled to room temperature and rinsed with nitrogen. The rectification allot of 120.5 g of 2-chloro-n-xilinhaote with so Kip. 120-125^oC/2,4-2,7 kPa. Yield 78% In the mixture of 120.5 g of 2-chloro-n-xilinhaote in 350 ml of acetone at 2-5^oC enter within 3 h of gaseous trimethylamine, obtained by the action of a 50% aqueous NaOH solution of 66 g of hydrochloric acid trimethylamine at 40^oC. the Crystalline precipitate the Quaternary ammonium salt is filtered off and dried, obtaining 153 g of salt (yield 95%).

The 4-necked flask equipped with stirrer, dropping funnel, thermometer and a refrigerator, the mixture was charged 600 g of a 50% aqueous solution of NaOH and 85 ml of n-xylene.

The mixture is heated to 110-120^oC with vigorous stirring was added dropwise a solution of 153 g of 2-chloro-n-methylbenzenesulfonamide in 110 ml of water for 60 minutes, a precipitate of yellow.

After the addition of the salt solution, the reaction mixture was stirred for 1.5 h at the same temperature. Eye-catching trimethylamine absorb conc. HCl. After cooling the reaction mass of the polymer precipitate is filtered off, the PoWPA is REGO sediment for 10 h in a Soxhlet extraction apparatus. The extract combined with the organic layer from the synthesis, the solvent is distilled off and get to 14.3 g of dichloro-di-n-xylylene with a basic substance content of 98.5% melting point dichloro-di-n-xylylene 185^oC. Yield in terms of 2-chloro-n-xylene 11,7%
Example 2. In the 87.3 g of 2-chloro-n-xylene at 160-165^oC and irradiation lamp of 500 W is passed a current of chlorine, drained conc. H₂SO₄with a speed of 15 g/h After absorption of 45 g of chlorine, the mixture is cooled, rinsed with nitrogen and rectification, allocate 90,2 g of 2-chloro-n-xilinhaote (yield 83% so Kip. 112-114^oC/1.07 kPa). The mixture is 90.2 g of 2-chloro-n-xilinhaote in 300 ml of acetone, cooled to 1-3^oC enter for 2.5 h of gaseous trimethylamine. The latter is obtained by the action of a 50% aqueous NaOH solution of 51 g of hydrochloric acid trimethylamine at 40-50^oC. the Precipitated crystals of 2-chloro-n-methylbenzeneethanamine chloride is filtered off, washed with chilled acetone and dried. Get 118,2 g of salt (yield 98%).

The solution 118,2 g of salt in 125 ml of water was added dropwise over 50 min to a mixture of 700 g of 50% NaOH and 80 ml of n-xylene, heated to 115-118^oC, under vigorous stirring. Upon completion of the addition the mixture is stirred for 1.5 h at the same temperature. The polymer precipitate is filtered off, the distillation of the solvent from the extract to produce 9.3 g of crystalline dichloro-di-n-xylylene. So pl. 195^oC, the content of the basic substance to 99.2% Yield 2-n-chloro-n-xylene 10,8%
Example 3. In to 112.2 g of 2-chloro-n-xylene at 160-164^oC and irradiation lamp 500 W miss chlorine speeds of 15-18 g/h After absorption of 57 g of chlorine, the reaction mass is then cooled, rinsed with nitrogen and divided into a distillation column. Get 117,4 g of 2-chloro-n-xilinhaote with a boiling point 104-110^oC/1,02 was 1.06 kPa. The output 84%
The mixture 117,4 g of 2-chloro-n-xilinhaote in 350 ml of acetone, cooled to 0-5^oC, passed in for about 2.5 h of gaseous trimethylamine, obtained by neutralization of 64 g of hydrochloric acid trimethylamine concentrated NaOH solution at 50-60^oC. the Separated salt is filtered off and dried. The output shall be 152.3 g (97%).

The solution shall be 152.3 g of 2-chloro-n-methylbenzenesulfonamide in 125 ml of water was added dropwise over 60 min in a mixture of 800 g of 50% NaOH solution and 100 ml of n-xylene, heated to 110^oC, intensive mixing. The reaction mass incubated 1.5 h at the same temperature and stirring. The polymer precipitate is filtered off, washed with water and dried. Extraction of sediment CCl₄in to conventional Soxhlet extractions for 8.5 h emit dichloro-di-n-xylylene. The solvent is distilled off, dichloro-di-n-xylylene planted b receive dichloro-di-p-xylylene, including photochemical chlorination of 2-chloro-p-xylene, the interaction of the resulting 2-chloro-p-xilinhaote with trimethylamine with the formation of 2-chloro-p-methylbenzhydrylamine, thermal decomposition, separation of the target product extraction, characterized in that the photochemical chlorination is carried out at 160 170^oC, interaction of 2-chloro-p-xilinhaote with trimethylamine is carried out at 0 to 5^oC and thermal decomposition is subjected directly to 2-chloro-p-methylbenzhydrylamine at 110 120^oin concentrated alkali solution.