Synthesis method of benzamide pesticide lufenuron

A synthesis method and technology of benzamide are applied in chemical instruments and methods, preparation of ethers by addition of unsaturated compounds, preparation of urea derivatives, etc., which can solve the problems of difficulty in solvent recovery, affecting the quality of finished products, and generation of by-products, etc. Conducive to environmental protection, good product quality and high yield

Active Publication Date: 2021-08-24
CHONGQING MEDICAL & PHARMA COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] In this patent, DMF is used as the solvent for the first addition and potassium hydroxide is used as the acid-binding agent. Due to the high boiling point of DMF, it is difficult to recover...

Method used

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  • Synthesis method of benzamide pesticide lufenuron
  • Synthesis method of benzamide pesticide lufenuron
  • Synthesis method of benzamide pesticide lufenuron

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of SMN-Z1

[0037] In the 500L reactor, add 37.6kg of 2,5-dichlorophenol, 250kg of acetonitrile, 37kg of phenol, and 190kg of saturated sodium carbonate aqueous solution in sequence, check the tightness of the reactor, stir for 30 minutes, vacuumize -0.08MPa, and control the temperature of the cooling water at 20-25°C, ventilate hexafluoropropylene, the venting time is about 4.5-5.5 hours, and the ventilating speed is as long as the temperature does not exceed 25°C; the reaction kettle does not display positive pressure. After the aeration is over, keep warm for 1-1.5 hours, and the sampling gas phase control is qualified, and the reaction is ended. Post-processing: separate layers, the water layer is used as alkaline water, the oil phase is first concentrated at normal pressure to recover acetonitrile to 80°C, then concentrated acetonitrile to 115°C under reduced pressure, and the vacuum degree -0.08MPa to complete the distillation and cool down to obtain t...

Embodiment 2

[0039] Preparation of SMN-Z1

[0040] In the 500L reactor, add 37.6kg of 2,5-dichlorophenol, 250kg of acetonitrile, 50kg of phenol, and 190kg of saturated sodium carbonate aqueous solution in sequence, check the tightness of the reactor, stir for 30 minutes, vacuumize -0.08MPa, and control the temperature of the cooling water at 20-25°C, ventilate hexafluoropropylene, the venting time is about 4.5-5.5 hours, and the ventilating speed is as long as the temperature does not exceed 25°C; the reaction kettle does not display positive pressure. After the aeration is over, keep warm for 1-1.5 hours, and the sampling gas phase control is qualified, and the reaction is ended. Post-processing: separate layers, the water layer is used as alkaline water, the oil phase is first concentrated at normal pressure to recover acetonitrile to 80°C, then concentrated acetonitrile to 115°C under reduced pressure, and the vacuum degree -0.08MPa to complete the distillation and cool down to obtain t...

Embodiment 3

[0042] Preparation of SMN-Z1

[0043] In the 500L reactor, add 37.6kg of 2,5-dichlorophenol, 250kg of acetonitrile, 35.7kg of phenol, and 190kg of saturated sodium carbonate aqueous solution in sequence, check the tightness of the reactor, stir for 30 minutes, vacuumize -0.08MPa, and control the temperature with cooling water Hexafluoropropylene is ventilated at 20-25°C for about 4.5-5.5 hours, and the ventilating speed is as long as the temperature does not exceed 25°C; the reaction kettle does not show positive pressure. After the aeration is over, keep warm for 1-1.5 hours, and the sampling gas phase control is qualified, and the reaction is ended. Post-processing: separate layers, the water layer is used as alkaline water, the oil phase is first concentrated at normal pressure to recover acetonitrile to 80°C, then concentrated acetonitrile to 115°C under reduced pressure, and the vacuum degree -0.08MPa to complete the distillation and cool down to obtain the finished produ...

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Abstract

The invention discloses a synthesis method of benzamide pesticide lufenuron, 2, 5-dichlorophenol is takend as a raw material, the lufenuron is obtained through the steps of addition with hexafluoropropylene, nitration, reduction and condensation in sequence, and the synthesis method is characterized in that the addition step of 2, 5-dichlorophenol and hexafluoropropylene comprises the following steps: adding 2, 5-dichlorophenol (SMN-SM-1), acetonitrile, phenol and a sodium carbonate aqueous solution into a reaction kettle, uniformly stirring and mixing, vacuumizing, controlling the temperature of cooling water to be 20-25 DEG C, introducing hexafluoropropylene, controlling the ventilation speed to ensure that the temperature in the reaction kettle is not higher than 25 DEG C and no positive pressure exists in the reaction kettle, and carrying out heat preservation reaction for 1-1.5 hours after ventilation is finished to obtain an intermediate SMN-Z1; the method is high in yield, good in product quality and easy to operate, solvents and catalysts used in the whole production process are all recycled and reused, the production cost is reduced, meanwhile, environmental protection is facilitated, and the method is more suitable for industrial production requirements.

Description

technical field [0001] The invention relates to a synthesis method of the benzamide pesticide lufenuron, which belongs to the field of organic synthesis. Background technique [0002] Lufenuron is the largest product among benzoylurea insecticides, and its structural formula is: [0003] [0004] In 1993, Syngenta first launched lufenuron in France, which was used for corn under the trade name Match. The main market for lufenuron is in the field of animal health. It is used to control fleas on cats and dogs. The trade name is Program. [0005] As the largest product among benzoylurea insecticides, lufenuron plays a pivotal role in the field of insecticide and acaricide. [0006] At present, there are two main synthetic routes of lufenuron, which are: [0007] route one [0008] [0009] In this route, N-(2,6-difluorophenyl)-N'-[2,5-dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl ] Urea is obtained by condensation of 2,6-difluorobenzoyl isocyanate with 2,5-dichlor...

Claims

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Application Information

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IPC IPC(8): C07C275/54C07C273/18C07C41/06C07C43/225C07C201/10C07C205/37C07C213/02C07C217/84C07C263/10C07C265/16
CPCC07C41/06C07C201/10C07C213/02C07C263/10C07C273/1827C07C43/225C07C205/37C07C217/84C07C265/16C07C275/54Y02A50/30
Inventor 刘殿卿邵倩何东贤侯媛芳谭文龙
Owner CHONGQING MEDICAL & PHARMA COLLEGE
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