Cyclic α-methylstyrene dimmer production process

FIELD: industrial organic synthesis.

SUBSTANCE: invention relates to production of cyclic α-methylstyrene dimmer, in particular 1,1,3-trimethyl-3-phenylindane, which is used as base for lubricating materials, propellants, and heat carriers. Process is accomplished via dimmerization of α-methylstyrene using, as catalyst, complex AlCl4*CCl3 formed in situ during interaction of activated powdered metallic Al with CCl3 at 50°C and atmospheric pressure, Al/CCl3/α-methylstyrene molar ratio being 10:25:3.9. Reaction time is 2 min. Selectivity of formation of desired product is 94% and α-methylstyrene conversion is 100%.

EFFECT: increased yield of desired product.

 

The invention relates to the field of production of cyclic dimer α-methylstyrene.

Cyclic dimer α-methylstyrene 1,1,3-trimethyl-3-phenylindane used as the basis for lubricants, jet fuels with high calorific value, heat transfer fluids.

A known method of producing dimers α-methylstyrene (2,4-diphenyl-4-methylpentene-1; 2,4-diphenylmethylene-2 and cyclic dimer-1,1,3-trimethyl-3-phenylindane) catalytic dimerization α-methylstyrene in the presence of a catalyst - triperoxonane acid at between 15 and 72°s, when the ratio of acid monomer is from 1:1 to 10:1 and the reaction time from 0.5 to 24 h, followed by separation triperoxonane acid by vacuum distillation at cooling collector a mixture of dry ice with acetone. [U.S. patent No. 3385905, CL 260-668, 1956.]

The disadvantages of this method is the need to use significant amounts of expensive and inaccessible catalyst-triperoxonane acid. The maximum yield of dimers by this method is 74%. Along with the dimers obtained more than 16% of higher oligomers. In addition, the use triperoxonane acid also requires complex technological design, special materials, as it, being a strong acid, destroys metal, cork, rubber, bakelite, polyethylene.

Known to the persons receiving dimers α -methylstyrene (2,4-diphenyl-4-methylpentene-1; 2,4-diphenylmethylene-2 and cyclic dimer-1,1,3-trimethyl-3-phenylindane) by dimerization α-methylstyrene when heated to 103-140°during 2-17 h using as catalyst for formic acid in the amount of 0.5-30 wt.%. [A.S. USSR №670555, CL SS 3/10, SS 15/12, 1979, B. I. No. 24.]

The output of dimers reaches 99 wt.%. The maximum yield of the cyclic dimer and 67.8%, with conversion the original α-methylstyrene - 39,5%.

The most significant drawback of this method is the formation of hardly separated mixture of linear dimers and cyclic dimer. When the output of the cyclic dimer 67,8% linear dimer is 20,8%and trimers of 11.4%.

The present invention is the development of a preparative method for the synthesis of cyclic dimer 1,1,3-trimethyl-3-phenylindane from α-methylstyrene (AMS).

The task is achieved by the described method of obtaining the cyclic dimer α-methylstyrene by dimerization α-methylstyrene in the presence of complex AlCl4-*CCl3+formed in situ by the interaction of activated metal Al powder with CCl4. [R.A. Sadykov, Megamachine, PN. Petrov, E. Paramonov, sea level Dzhemilev. The conversion of cyclohexane under the action of aluminum halides generated IN SITU, the ur. Applied Chemistry, 2004, t, vyp.] The process of dimerization is carried out at a temperature of 50°C, atmospheric pressure and a molar ratio Al:CCl4:AMC 10:25:3,9. The selectivity of the formation of cyclic dimer 1,1,3-trimethyl-3-phenylindane 94% conversion of the original α-methylstyrene - 100%. The reaction time is 2 minutes

The proposed method is illustrated by the following example.

In a glass reactor with a volume of 100 ml was placed 0.5 g (10 g-at) metal powder of aluminum, activate the crystal iodine to its full sublimation by heating (1-2 min). A reactor equipped with reflux condenser and thermometer, is placed on the magnetic stirrer, and then add 2.5 ml (25 mmol) CCl4, heated to 50°and add 0.5 ml (3.9 mmol) α-methylstyrene. After 2 min, the reaction mixture is cooled to 20°and hydrolyzing water. Separate the organic layer. The sample was analyzed by GLC on a chromatograph Color 500 M Conditions analysis: steel column with 0.125-0.16 mm*20 m with a stationary liquid phase SE-30 linear programming temperature from 50 to 270°With speed 8°C/min, carrier Gas - helium, the speed of carrier gas 30 ml/min Detector flame ionization (PID). The detector temperature -270°C, the temperature of the evaporator -295°C. the Selectivity of the formation of cyclic dimer 1,1,3-trimethyl-3-phenyl who ndana 94% conversion of the original α -methylstyrene - 100%, the proportion of linear dimer (2,4-diphenylmethylene-2) - 1.4%, trimer - 4,6%.

A method of obtaining a cyclic dimer α-methylstyrene by catalytic dimerization α-methylstyrene, characterized in that the catalyst used is a complex of AlCl4-*CCl3+formed in situ by the interaction of activated metal Al powder with CCl4in a molar ratio Al:CCl4:AMC 10:25:3,9, at a temperature of 50°C.



 

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