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New technology of synthesizing fenoxycarb

A technology of fenoxycarb and a new process, which is applied in the new process field of synthesizing fenoxycarb, can solve the problems of decreased catalytic activity and selectivity, restrictions on the popularization and use of fenoxycarb, and high reaction temperature, and can overcome the long reaction time and the high reaction temperature. The effect of shortening the time and high product purity

Inactive Publication Date: 2006-06-14
PILARQUIM SHANGHAI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, the catalysts used in the production process of fenoxycarb mainly include active copper powder, Cu 2 O, CuCl, CuBr, etc., the active copper powder is easily oxidized, when the catalyst and the reaction mixture are exposed to the air (especially at high temperature), its catalytic activity and selectivity will drop rapidly, and the copper salt will not dissolve in the reaction system. What happens is a liquid-solid complex phase catalytic reaction, the reaction time is long, the reaction temperature is high, and the yield is low
Therefore, the high production cost limits the popularization and use of fenoxycarb

Method used

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  • New technology of synthesizing fenoxycarb
  • New technology of synthesizing fenoxycarb
  • New technology of synthesizing fenoxycarb

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] In a four-neck flask equipped with stirring, a thermometer and a water separator, add 700 g of phenol, 84.0 g of potassium hydroxide, and 400 ml of toluene, heat and stir, and perform azeotropic dehydration. Add 6.0 g of the pre-prepared composite catalyst (weigh 4.0 g of 1,10-phenanthroline and dissolve in methanol, add 2.0 g of CuCl and stir for 1 hour until uniform, then evaporate the methanol). Heat up to 170°C and add 129 g of p-chlorophenol (1.0 mol) dropwise. After the addition is complete, react at 180°C for 3 hours. Cool to room temperature, adjust to pH = 2 with 10% HCl, separate the oil layer, wash with water until neutral, dry and distill under reduced pressure, first recover the solvent and phenol, collect the fraction at 145-148°C / 800Pa as the product 4-phenoxy Base phenol, a total of 131.0g, a purity of 94.5%, a yield of 70.4% (based on 1 mole of p-chlorophenol).

[0025] Use 4-phenoxyphenol to react with ethyl 2-chloroethyl carbamate to obtain fenoxyca...

Embodiment 2

[0027] Add 470g of phenol, 84.0g of potassium hydroxide, and 400ml of toluene to a four-necked flask equipped with stirring, a thermometer and a water separator, heat and stir for azeotropic dehydration. Add 4.0 g of the pre-prepared composite catalyst (weigh 2.5 g of 1,10-phenanthroline and dissolve it in methanol, add 1.5 g of CuCl and stir for 1 hour until uniform, then evaporate the methanol). Heat up to 170°C, add 129g of p-chlorophenol (1.0mol) dropwise, and continue reaction at 170°C for 4 hours after addition. The remaining operations were the same as in Example 1 to obtain 121.6 g of the product 4-phenoxyphenol with a purity of 95.5% and a yield of 65.4%.

[0028] Fenoxycarb is obtained by reacting 4-phenoxyphenol with ethyl 2-chloroethyl carbamate, the purity is ≥98%, and the yield is 95%.

Embodiment 3

[0030] Add 470g of phenol, 84.0g of potassium hydroxide, and 400ml of toluene into a four-neck flask equipped with stirring, a thermometer and a water separator, heat and stir, and perform azeotropic dehydration. Add the pre-prepared composite catalyst (weigh 4.5g 1,10-phenanthroline and 1.5g 2,2'-biquinoline and dissolve in methanol, add 3.5g CuBr and stir for 1 hour until uniform, distill off methanol). Heat up to 170°C, add 129g of p-chlorophenol (1.0mol) dropwise, and react at 180°C for 3 hours. The remaining operations were the same as in Example 1 to obtain 125.2 g of the product 4-phenoxyphenol with a purity of 95.7% and a yield of 67.5%.

[0031] Fenoxycarb is obtained by reacting 4-phenoxyphenol with ethyl 2-chloroethyl carbamate, the purity is ≥98%, and the yield is 95%.

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Abstract

The invention discloses a new process for synthesizing fenoxycarb, specifically disclosing a new process for synthesizing fenoxycarb with a composite catalyst. The new process includes using phenol and p-chloro The reaction of phenol produces 4-phenoxyphenol, and then the reaction of 4-phenoxyphenol and 2-chloroethyl ethyl formate produces fenoxycarb. The composite catalyst consists of a main catalyst monovalent Cu(I) compound such as Cu 2 O, CuCl, CuBr and cocatalysts are composed of nitrogen-containing heterocyclic compounds containing functional groups such as 1,10-phenanthroline, 2,2'-bipyridine, and 2,2'-biquinoline. The new process has the characteristics of fast reaction speed, mild reaction conditions and high product yield.

Description

technical field [0001] The invention relates to a new process for synthesizing fenoxycarb, in particular to a new process for synthesizing fenoxycarb with a composite catalyst. Background technique [0002] Fenoxycarb, also known as fenoxycarb and fenoxycarb, has a chemical name of 2-(p-phenoxyphenoxy)ethyl carbamate, which was developed by Ciba-Geigy in Switzerland in 1982. It is the only juvenile hormone pesticide with broad-spectrum insecticidal effect successfully developed so far. The pesticide has the advantages of low toxicity, high efficiency, broad spectrum, not easy to produce resistance, and does not pollute the environment. Especially it has special effects on pests that have developed resistance to conventional pesticides such as pyrethroids and organophosphorus, such as diamondback moth, beet armyworm, cabbage caterpillar, cabbage aphid, apple yellow aphid, etc. It is an ideal medicine for pollution agricultural production. [0003] Fenoxycarb is an insect g...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C271/16C07C269/00B01J23/72B01J31/02
Inventor 陆庆宁叶锡纯周祖新周长结
Owner PILARQUIM SHANGHAI
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