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Preparation method of trifluoromethyl ketone

A technology of trifluoromethyl ketone and sodium trifluoroacetate, applied in the field of preparation of trifluoromethyl ketone, can solve the problems of difficult control of the reaction process, high requirements on process equipment, many by-products, etc. The effect of cheap and easily available raw materials and mild process conditions

Inactive Publication Date: 2013-07-31
JUHUA GROUP TECH CENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Trifluoromethyl ketones are currently mainly prepared by fluorinating trichloromethyl ketone or tribromomethyl ketone with hydrogen fluoride. This method has high requirements for process equipment, many by-products, and is difficult to separate from the product.
The disadvantage is that the produced ethanol by-product is difficult to separate from the solvent or the product, which is not conducive to the recovery and application of the solvent, and it is difficult to purify the product
However, the preparation cost of lithium trifluoroacetate is high, and the reaction process is violent and difficult to control, and it is not easy to industrialize

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 1 mol of sodium trifluoroacetate, 1.05 mol of magnesium chips, and 1.2 mol of tetrahydrofuran as a solvent into a 1L stainless steel reaction kettle. After nitrogen replacement three times, heat the temperature inside the kettle to 50°C, and intermittently feed 1.1mol of methyl chloride gas to make the kettle The pressure is maintained at 0.1-0.3MPa, and the reaction temperature is controlled at 60°C for the reaction. At the same time, 2.4mol (200ml) of solvent tetrahydrofuran is added to the reaction kettle at a speed of 3.3ml / min with a high-pressure constant-flow pump, and the temperature is raised to 65 °C, the reaction was stopped after stirring for 2 h. After the reaction solution was cooled to room temperature, it was acidified with 500 ml of 2 mol / L sulfuric acid solution, the organic layer was collected, and purified by rectification to obtain 1,1,1-trifluoroacetone. Yield 59%, purity 99%.

Embodiment 2

[0027] Add 1 mol of sodium trifluoroacetate, 1.1 mol of magnesium chips, and 1 mol of solvent 2-methyl-tetrahydrofuran into a four-neck flask, heat to 40°C and stop heating, and add bromoethane 1.19 mol dropwise into the bottle at a rate of 5ml / min. mol (90ml) and 6mol (610ml) of 2-methyl-tetrahydrofuran, the reaction temperature was controlled at 40°C. After the dropwise addition was completed, the temperature was raised to 50°C to continue the reaction for 2 hours and then stop the reaction. After cooling the reaction liquid to room temperature, it was acidified with 500 ml of 3.5 mol / L hydrochloric acid solution, and the organic layer was collected and purified by rectification to obtain 1,1,1-trifluoro-2-butanone. Yield 67%, purity 99%.

Embodiment 3

[0029] Add 1.45mol of magnesium chips and 100ml of diethyl ether into a four-necked flask, first drop a mixture of 1.50mol (150ml) of benzyl bromide (150ml) and 0.96mol of diethyl ether (100ml) into the flask at a speed of 4.5ml / min, and then dropwise add three A mixture of 1 mol of sodium fluoroacetate and 2.86 mol of diethyl ether (total 300 ml), the temperature of the whole dropping process was controlled at 30°C, after the dropwise addition was completed, the temperature was raised to 35°C to continue the reaction for 1 hour and then stop the reaction. After the reaction solution was cooled to room temperature, it was acidified with 500 ml of 2.5 mol / L sulfuric acid solution, the organic layer was collected, and purified by rectification to obtain trifluoromethyl benzyl ketone. Yield 58%, purity 99%.

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Abstract

The invention provides a preparation method of trifluoromethyl ketone. The preparation method of the trifluoromethyl ketone comprises the following steps: (1) after being mixed, magnesium metal, solvent, halide and sodium trifluoroacetate are reacted for 0.5-2.5 hours at the temperature of 30-65 DEG C, and then are reacted for 1-3 hours at the rising temperature of 30-70 DEG C, the molar ratio of the halide and the magnesium metal is 1-1.2:1, the molar ratio of the solvent and the magnesium metal is 2-8:1, the molar ratio of the magnesium metal and the sodium trifluoroacetate is 1-1.5:1, and after the reaction finishes, obtained reaction liquid is cooled; (2) the reaction liquid is added to 2-4 mol / L of mineral acid and is acidized, an organic layer is collected, the organic layer is rectified and purified, and then the trifluoromethyl ketone is obtained. The trifluoromethyl ketone has the advantages of being low in raw material cost, low in production cost, easily purified and low in production equipment requirements, wherein the raw materials of the trifluoromethyl ketone are easy to get.

Description

technical field [0001] The invention relates to a preparation method of ketone compounds, in particular to a preparation method of trifluoromethyl ketone. Background technique [0002] Trifluoromethyl ketone compounds are an important class of organic intermediates of fluorine-containing liquid crystal materials and fluorine-containing drugs, and have also been applied in the preparation of nonlinear optical materials and the manufacture of water vapor sensors. Trifluoromethyl ketone compound preparation method is as follows: [0003] Trifluoromethyl ketones are currently mainly prepared by fluorinating trichloromethyl ketone or tribromomethyl ketone with hydrogen fluoride. This method has high requirements for process equipment, many by-products, and is difficult to separate from the product. [0004] JP2011190216A discloses a method for preparing a trifluoromethyl ketone compound. In this method, a Grignard reagent is reacted with ethyl trifluoroacetate to prepare a trifl...

Claims

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Application Information

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IPC IPC(8): C07C49/167C07C49/233C07C49/80C07C45/68
Inventor 胡正周强耿为利兰喜平
Owner JUHUA GROUP TECH CENT
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