The way to obtain 1,1-dichloro-2,2-bis-(4-chlorophenyl)ethylene

 

(57) Abstract:

The invention relates to the field of chemistry of aromatic organochlorine compounds, and in particular to a method for producing 1,1-dichloro-2,2-(4-chlorophenyl)ethylene. Essence: 1,1,1-trichloro-2,2-bis-(4-chlorophenyl)ethane helps eliminate hydrogen chloride crystalline alkali at a molar ratio of 1,1,1-trichloro-2,2-bis-(4-chlorophenyl)ethane : alkali as 1 : (1,5 - 1,75) and the process is conducted in the presence of the catalyst benzyltriethylammonium chloride.

The invention relates to the field of chemistry organochlorine compounds, and in particular to a method for producing 1,1-dichloro-2,2-bis- (4-chlorophenyl)ethylene

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which can be used as an additive to polyester resins to improve the fire resistance.

A method of obtaining 1,1-dichloro-2,2-bis-(4-chlorophenyl)ethylene removal of hydrogen chloride alcohol alkali solution of 1,1,1-trichloro-2,2-bis-(4-chlorophenyl)ethane [1,2] . The reaction is carried out with 3-fold excess of alkali boiling for 10 hours Using a diluted solution of alcohol alkali (~2%). The yield is 81%.

Also known is a method of obtaining 1,1-dichloro-2,2-bis-(4-chlorophenyl)ethylene of 1,1,1-trichloro-2,2-bis-(4-chlorophenyl)ethane as acceptor chloric organic solvents, preferably the reaction in ethyl cellosolve.

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The closest is the way to obtain 1,1-dichloro-2,2-bis-(4-chlorophenyl)ethylene of 1,1,1-trichloro-2,2-bis-(4-chlorophenyl)ethane using an alcoholic solution of alkali [1] . The process is carried out at the boiling temperature of the alcohol. For elimination of use threefold excess of alkali. The reaction mass consisting of 1,1,1-trichloro-2,2-bis-(4-chloro-phenyl)ethane, 3-fold excess of alkali and alcohol is boiled for 10 hours. Then spend the isolation and purification of the obtained 1,1-dichloro-2,2-bis-(4 - chlorophenyl)ethylene. To highlight a product of the pre-reaction mass is distilled alcohol.

The disadvantage of this method is that elimination using a large excess of alkali (up to three times). The elimination process is within 10 h at the boiling temperature of the alcohol. Technology explosive, because it is used legkonastraivaemy solvent is ethyl or propyl alcohol.

The invention is aimed at simplifying the technology for 1,1-dichloro-2,2-bis(4-chlorophenyl)ethylene.

This is achieved by elimination of hydrogen chloride from 1,1,1-trichloro-2,2-bis-(4-chlorophenyl)ethane exercise crystalline seatstay catalyst benzyltriethylammonium.

For implementing the method uses the following materials: 1,1,1-trichloro-2,2-bis-(4-chlorophenyl)ethane - so pl. to 108.5-109oC, NaOH - GOST 4328-77; benzyltriethylammonium chloride - TU 6-09-05-542-76.

The method is as follows.

To 0.5 mol of 1,1,1-trichloro-2,2-bis-(4-chlorophenyl)ethane was added to 0.75 mol of alkali and 0.0005 mol of benzyltriethylammonium chloride. The mixture is heated at 90-100oC for 40-60 minutes the resulting mass is neutralized with an aqueous solution of hydrochloric acid. The precipitate is filtered off and dried. Output 93-97%, so pl. 88-89oC. Lit.[1] T. pl. 88-89oC.

The distinction of the proposed solutions from known is used as the eliminating agent of the crystalline alkali and catalyst. This avoids the use of organic solvents, a large excess of alkali (2 times), to reduce the reaction time (10 times), as well as to forgive the selection of the final product.

The optimum amount of alkali is 1,5-1,75 mol per 1 mol of 1,1,1-trichloro-2,2-bis-(4-chlorophenyl)ethane. Decreasing this number, the yield of the desired product decreases. To increase this number has no meaning, because the output is not increasing, not decreasing the duration of the reaction.

Example 1. The mixture is and is heated under stirring for 40-60 min and a temperature of 90-100oC. Then the reaction mixture was neutralized with an aqueous solution of hydrochloric acid. The precipitate is filtered off and dried. The output 154 g (97%), so pl. 88-89oC. Lit.[1] T. pl. 88-89oC.

Example 2. Analogously to example 1. From a mixture containing 0.5 mol of 1,1,1-trichloro-2,2-bis-(4-chlorophenyl)ethane, 1 mol of NaOH, of 0.0005 mol benzyltriethylammonium chloride, receive 1,1-dichloro-2,2-bis-(4-chlorophenyl)ethylene with 96% yield. So pl. 88-89oC. Lit.[1] T. pl. 88-89oC.

Example 3. Analogously to example 1. From a mixture containing 0.5 mol to 1.1.1-trichloro-2,2-bis-(4-chlorophenyl)ethane, 0.5 mol of NaOH, of 0.0005 mole benzyldimethyl-ammonium chloride, receive 1,1-dichloro-2,2-bis-(4-chlorophenyl)ethylene with 59% yield. So pl. 88-89oC. Lit. [1] T. pl. 88-89oC.

The way to obtain 1,1-dichloro-2,2-bis-(4-chlorophenyl)ethylene by treatment with 1,1,1-trichloro-2,2-bis-(4-chlorophenyl)ethane alkali at elevated temperature, characterized in that the alkali used crystalline alkali and the process is conducted at a molar ratio of 1,1,1-trichloro-2,2-bis - (4-chlorophenyl)ethane : lye, which is 1 : 1.5 to about 1.75, in the presence of a catalyst of benzyltriethylammonium chloride.

 

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