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Method for continuously preparing 3,4'-dichlorodiphenyl ether

A technology of dichlorodiphenyl ether and m-dichlorobenzene, applied in the direction of ester reaction to prepare ether, ether preparation, organic chemistry, etc., can solve the problems of low reaction selectivity, low efficiency, non-environmental friendliness, etc., and shorten the reaction time , Shorten the production cycle, improve the reaction yield and selectivity

Active Publication Date: 2018-05-25
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reaction selectivity is low, the highest yield is about 80%, and about 20% of solid waste is produced at the same time, which is a low-efficiency and non-environmentally friendly process technology

Method used

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  • Method for continuously preparing 3,4'-dichlorodiphenyl ether
  • Method for continuously preparing 3,4'-dichlorodiphenyl ether
  • Method for continuously preparing 3,4'-dichlorodiphenyl ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 50g (0.39mol) p-chlorophenol, 16.3g NaOH (0.41mol), 572g (3.9mol) m-dichlorobenzene, 15.5g (0.2mol) DMSO into a 500ml round bottom flask, react at 90°C for 1 hour, then add 1g of CuCl catalyst , React at a temperature of 175°C for 2h. The reaction situation of the reaction solution was detected by high performance liquid chromatography, and the remaining sodium p-chlorophenolate was within 1%. After the reaction solution was filtered, m-dichlorobenzene and DMSO were recovered by distillation, and the remaining fraction was distilled under reduced pressure to obtain 74.4 g of the product with a content of 98.9% and a yield of 80%.

Embodiment 2

[0025] Add 50g (0.39mol) p-chlorophenol, 15.5g NaOH (0.39mol), 572g (3.9mol) m-dichlorobenzene into a 500ml round bottom flask, react at 90°C for 1 hour, and remove water under reduced pressure. 30.3 g (0.39 mol) of DMSO, 0.2 g of polyvinylpyrrolidone, and 1 g of CuCl catalyst were added. Tubular reactor through N 2 After three replacements, set the pressure at 0.3MPa. The mixed system was pumped into the tubular reactor through a high-pressure liquid phase pump, the flow rate was 1.2ml / min, the residence time was 40min, and the reaction temperature was 175°C. The reaction situation of the reaction solution in the collector is detected by high performance liquid chromatography, and the remaining sodium p-chlorophenolate is within 1%. After the reaction solution was filtered, m-dichlorobenzene and DMSO were recovered by distillation, and the remaining fraction was distilled under reduced pressure to obtain 76.2 g of the product with a content of 99.3% and a yield of 85%.

Embodiment 3

[0027] Add 50g (0.39mol) p-chlorophenol, 15.5g NaOH (0.39mol), 572g (3.9mol) m-dichlorobenzene into a 500ml round bottom flask, react at 90°C for 1 hour, and remove water under reduced pressure. Add 30.3g (0.39mol) of DMSO, 0.2g of polyvinylpyrrolidone, and 1g of nanoscale iron powder catalyst. Tubular reactor through N 2 After three replacements, set the pressure at 0.3MPa. The mixed system was pumped into the tubular reactor through a high-pressure liquid phase pump, the flow rate was 1.2ml / min, the residence time was 40min, and the reaction temperature was 175°C. The reaction of the reaction solution in the collector was detected by high performance liquid chromatography. After the reaction solution was filtered, m-dichlorobenzene and DMSO were recovered by distillation, and the remaining fraction was distilled under reduced pressure to obtain 35.3 g of the product with a content of 98.6% and a yield of 38%.

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Abstract

The invention discloses a novel method for continuously preparing 3,4'-dichlorodiphenyl ether. The novel method comprises the following steps: (1) preparing parachlorophenol into sodium phenolate salt, adding a solvent, an emulsifying agent, copper-series, zinc-series or iron-series catalysts after being dehydrated to prepare a mixed system; (2) pumping the mixed system into a tubular reactor through a liquid-phase pump, wherein a reaction temperature is 140-200 DEG C, standing time is 20-50 minutes, and distillation purification is performed to obtain a product after reaction is ended. Compared with conventional kettle type reaction, the novel method greatly increases reaction speed and shortens reaction time. Reaction selectivity is improved to 90% from 85% and the reaction yield is increased to 85% from 80%; the reaction yield and the reaction selectivity are improved, so that production efficiency and safety are improved, emission of waste is reduced, and reaction equipment investment is greatly reduced. The method is a novel method which is safe, is high in efficiency and is environmentally friendly.

Description

technical field [0001] The present invention is a new method and process for high-selectivity catalysis and continuous preparation of 3,4' dichlorodiphenyl ether. 3,4' dichlorodiphenyl ether is a kind of important pesticide intermediate. The catalyst used All are copper, iron and zinc catalysts, and the technical field of the invention belongs to the field of catalytic chemistry and fine chemical industry. Background technique [0002] Diaryl ether compounds are important pharmaceutical and pesticide intermediates, among which 3,4' dichlorodiphenyl ether is an important intermediate of the pesticide difenoconazole. Difenoconazole, also known as difenoconazole, trade name "Shigao", is a triazole fungicide and a sterol demethylation inhibitor. It has the characteristics of high efficiency, broad spectrum, low toxicity and low dosage. An excellent variety of triazole fungicides, with strong systemic property. By inhibiting the biosynthesis of ergosterol in pathogen cells, ther...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/16C07C43/29
CPCC07C41/16C07C43/29
Inventor 孙亮郑卓徐雪峰薛兴亚梁鑫淼
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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