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Method for preparing chlorinated diphenyl ether

A technology of chlorinated diphenyl ether and diphenyl ether, which is applied in the field of preparation of chlorinated or polychlorinated diphenyl ethers, can solve the problems of many by-products and high reaction temperature, and achieves the advantages of accelerated reaction speed and high product yield. Effect

Inactive Publication Date: 2009-05-06
ANHUI LIXING CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, the reaction product chlorinated diphenyl ether will also react with phenate to produce by-products such as trimer or tetra-polyether. If the reaction temperature is high, there will be more by-products.

Method used

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  • Method for preparing chlorinated diphenyl ether
  • Method for preparing chlorinated diphenyl ether
  • Method for preparing chlorinated diphenyl ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Preparation of 4-chloro-diphenyl ether

[0047] Add 94g of phenol, 650g of p-dichlorobenzene, 1g of cuprous chloride with an average particle size of 600nm, 0.5g of potassium iodide, 150g of dimethylacetamide and 50mL of xylene into a four-necked flask, and add 40g of sodium hydroxide to it while stirring , and then gradually increase the temperature until the inner temperature reaches 120°C and starts to azeotrope, and the dehydration is completed when the inner temperature reaches 160°C, then continue to stir and react at 160-165°C for 12 hours, stop heating, let stand to cool, and filter. The filtrate was distilled under reduced pressure, and the fraction at 135-138° C. / 6 mmHg was collected to obtain 164.8 g of a colorless transparent liquid. The yield of 4-chloro-diphenyl ether (calculated as phenol) is 80.6%, and the content is 99.3% through gas chromatography analysis.

Embodiment 2

[0049] Preparation of 3-chlorodiphenyl ether

[0050] Add 94g of phenol, 650g of m-dichlorobenzene, 2.5g of cuprous chloride with an average particle size of 600nm, potassium carbonate, 150g of dimethylacetamide and 50mL of xylene into a four-necked bottle, and gradually heat up to an internal temperature of 140°C. Azeotrope, then slowly raise the temperature to 160-165°C and continue stirring for 12 hours, stop heating, let stand to cool, and filter. The filtrate was distilled under reduced pressure, and the fraction at 128-132°C / 5mmHg was collected to obtain 175.3 g of a colorless transparent liquid. The yield of 3-chloro-diphenyl ether (calculated as phenol) is 85.7%, and the content is 99.5% through gas chromatography analysis.

Embodiment 3

[0052] Preparation of 3,4'-dichlorodiphenyl ether

[0053] Add 130g of p-chlorophenol, 600g of m-dichlorobenzene and 100mL of toluene into a four-neck flask, add 41g of sodium hydroxide to it, and perform azeotropic dehydration at 120-140°C. During the dehydration process, most of 65mL of toluene will be co-distilled, and then add 1.5g of cuprous chloride with an average particle size of 600nm and 60g of diethylene glycol diethyl ether were heated up to 170°C, and the reaction was continued with stirring at 170°C for 20h. Cool to room temperature after the reaction, filter and distill the filtrate under reduced pressure, collect the fraction at 146°C / 5mmHg to obtain 219g of a colorless transparent liquid. The yield of 3,4'-dichlorodiphenyl ether (in terms of p-chlorophenol) is 90.6%, and through gas chromatography analysis, the content is 99.2%.

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Abstract

The invention discloses a method for preparing chloro-substituted diphenyl ether or polychloro-substituted diphenyl ether. A target compound is generated by dichlorobenzene and phenol or fortified phenol which are added or not added with an organic solvent in the presence of a chlorine hydride absorbent for an Ullmann reaction under the catalysis of a catalyst; the chlorine hydride absorbent is one or more of sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate; the solvent is a polar or non-polar organic solvent, and the using amount of the solvent accounts for 0 to 50 percent of total reaction materials; and the catalyst is iodide or a copper compound or a mixture of the iodide and the copper compound. The method has the advantages that the method adopts the optimized mixture ratio of raw materials, a mixed solvent system and a copper catalyst with a nano-grain diameter, and ensures that the reaction rate is accelerated and a product has high yield.

Description

technical field [0001] The invention relates to a preparation method of diphenyl ether. More specifically, it relates to a preparation method of chlorinated or polychlorinated diphenyl ethers. Background technique [0002] Diaryl ether compounds are important pesticides and pharmaceutical intermediates, wherein chlorinated diphenyl ether is a special diphenyl ether, and chlorine is a reactive group that can be converted into amine groups, etc. (Synthetic Chemistry, 2003, 11 , 37), can be used as intermediates to prepare medicines and pesticides (EP 0051235, 0065485, 126430), wherein the difenoconazole (DE 3140277) compound is a pesticide with large dosage and good bactericidal effect; and, It can also be used in the manufacture of plant growth regulators (USP4124370) or hydraulic oil (USP3472782); or instead of polychlorinated biphenyls to manufacture capacitors; while polychlorinated diphenyl ethers and their downstream products polyaminodiphenyl ethers can also be used as...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/01C07C43/29C07C43/275
Inventor 汪德林黄绪民程宏田
Owner ANHUI LIXING CHEM
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