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Synthesis method of (3,4-dimethoxyphenyl)(4-p henyl fluoride) ketone

A technology of dimethoxyphenyl and fluorophenyl, applied in the direction of condensation preparation of carbonyl compounds, organic chemistry, etc., can solve the problems of large amount of catalyst usage, discharge of waste water and waste residue, non-recyclability, etc., and achieve less energy consumption, lower The effect of reducing the discharge of waste water and the amount of catalyst

Inactive Publication Date: 2017-05-24
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Although anhydrous aluminum chloride can make the reaction obtain ideal yields and is cheap, the disadvantage of this type of catalyst is that the lone pair of electrons in the aromatic ketone product formed by the reaction will complex with the halide catalyst, so it is necessary to add an excessive amount of The ratio of halide catalysts often requires more than 2 mol of Lewis acid catalysts to produce 1 mol of aromatic ketone products, which leads to serious waste of resources in practical applications
At the same time, the complexes generated need to be neutralized by strong acid and strong base, so a large amount of waste liquid is produced, which also leads to environmental unfriendly problems such as equipment damage
In addition to the huge amount of catalyst used, the excessive use of phthalate leads to the discharge of a large amount of waste water and waste residue, and cannot be recycled, resulting in high production costs and high pressure on environmental protection.

Method used

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  • Synthesis method of (3,4-dimethoxyphenyl)(4-p henyl fluoride) ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] According to the molar ratio of p-fluorobenzoyl chloride, phthaloyl ether, solvent and catalyst of 1:1:10:0.5, weigh 5 g of p-fluorobenzoyl chloride (chemically pure) and phthalene (chemically pure) respectively. 4.09g, solvent (chemically pure) 40g, ionic liquid catalyst [Bmim]Cl-AlCl 3 8.7g was added into a 100ml three-necked flask, and the solvent was chloroform, the same as in the following examples. The three ports of the flask are respectively equipped with a nitrogen feeding device, a mechanical stirring device, and a condenser. Then, put the flask into an oil bath, turn on the stirring and heating, keep the temperature at 60°C, and the reaction time is 4 hours. After the reaction, wait for it to cool to room temperature, pour the obtained solution into a separatory funnel, add water to the separatory funnel, the amount of water added is twice the volume of the obtained solution, fully hydrolyze the obtained solution, wash, extract, and statically After separati...

Embodiment 2

[0035] According to the molar ratio of p-fluorobenzoyl chloride, phthaloyl ether, solvent and catalyst as 1:1.5:10:0.3, weigh 5 g of p-fluorobenzoyl chloride (chemically pure) and phthalyl ether (chemically pure) 6.13g, solvent (chemically pure) 60g, ionic liquid catalyst [Bmim]Br-ZnCl 2Add 5.22g into a 100ml three-necked flask, install a nitrogen device, a mechanical stirring device, and a condenser at the three ports of the flask, and then put the flask into an oil bath, turn on the stirring and heating, keep the temperature at 60°C, and the reaction time is 4 Hour. After the reaction, wait for it to cool to room temperature, pour the obtained solution into a separatory funnel, add water to the separatory funnel, the amount of water added is 1 times the volume of the obtained solution, fully hydrolyze the obtained solution, wash, extract, and statically After separating the liquid, add water and wash once; the obtained organic phase is subjected to vacuum rotary evaporation...

Embodiment 3

[0037] According to the molar ratio of p-fluorobenzoyl chloride, phthaloyl ether, solvent and catalyst as 1:2:10:0.4, weigh 5 g of p-fluorobenzoyl chloride (chemically pure) and phthalyl ether (chemically pure) 8.17g, solvent (chemically pure) 40g, ionic liquid catalyst [Bmim]Br-CuCl 2 Add 6.96g into a 100ml three-necked flask, install a nitrogen device, a mechanical stirring device, and a condenser at the three ports of the flask, and then put the flask into an oil bath, turn on the stirring and heating, keep the temperature at 60°C, and the reaction time is 4 Hour. After the reaction, wait for it to cool to room temperature, pour the obtained solution into the separatory funnel, add water to the separatory funnel, the amount of water added is 1.5 times the volume of the obtained solution, fully hydrolyze the obtained solution, wash, extract, statically After separating the liquid, add water and wash once; the obtained organic phase is subjected to vacuum rotary evaporation ...

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Abstract

The invention relates to a synthesis method of (3,4-dimethoxyphenyl)(4-p henyl fluoride) ketone, and solves the problem that in the prior art, the synthesis method brings large amout of pollution and the cost is high. According to the method, acidic ionic liquid is applied as the catalyst which is polymerized by an ionic liquid precursor containing positive electricity and metal halides with negative electricity, wherein, the ionic liquid precursor is [Bmim] C1 or [Bmim] Br, the metal halide is AlCl3, FeC13, ZnCl2 or CuCl2. The synthesis method of (3,4-dimethoxyphenyl)(4-p henyl fluoride) ketone has the advantages of largely reducing the use amout of catalysts, lowering the emission of the waste water, saving the neutralization process of sulfuric acid, eliminating the waste water generated in the step, avoiding the corrosion caused by strong acid. Compared with the original reaction, the emission of slag is omitted. The reaction product is easy to be separated. The post-treatment is simpler. The reaction temperature is low. The energy cost is low. The product yield rate can reach as high as 97% or higher.

Description

technical field [0001] The invention is a new method for synthesizing (3,4-dimethoxyphenyl)(4'-fluorophenyl)methanone with an acidic ionic liquid catalyst. Background technique [0002] (3,4-dimethoxyphenyl)(4'-fluorophenyl)methanone, molecular formula C 15 h 13 FO 3 , molecular weight 260, white or off-white powder. [0003] (3,4-dimethoxyphenyl)(4′-fluorophenyl)methanone can be dissolved in organic solvents and monomers such as ethanol, ether, chloroform, etc., but insoluble in water. It is an important chemical intermediate . It can be used as an ultraviolet absorber, initiator, anhydrous indicator, etc., and is currently mainly used in the preparation of the insecticide flumorph. [0004] Flumorph (common name: Flumorph, trade name: Meike) is a fluorine-containing diphenylacryloylmorpholine fungicide created and developed by Shenyang Research Institute of Chemical Industry. It is the first one with independent intellectual property rights in my country. Agricultural...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/46C07C49/84
CPCC07C45/46C07C49/84
Inventor 黄崇品王琨张佳瑾陈标华李英霞
Owner BEIJING UNIV OF CHEM TECH
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