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Improved process method for preparing 5-chloroindanone

A chlorindanone and process improvement technology, applied in the field of organic synthesis, can solve the problems such as no public refining method, and achieve the effects of shortening production hours, avoiding losses, and reducing consumption

Active Publication Date: 2021-06-11
上海鼎素精细化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] The patent does not disclose the refining method. The applicant tried to dissolve, separate the tar and decolorize the activated carbon, and the obtained product is still yellow or light yellow powder. After dissolving the product, there is still a small amount of black tar substance

Method used

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  • Improved process method for preparing 5-chloroindanone
  • Improved process method for preparing 5-chloroindanone
  • Improved process method for preparing 5-chloroindanone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1 (traditional process)

[0037]

[0038] Put 225g (2.0mol, 1eq) of chlorobenzene into the reaction bottle, cool down to 25-30°C, add 333g (2.5mol, 1.25eq) of aluminum trichloride under stirring, and slowly add dropwise at the temperature of 25-30°C 254g (2.0mol, 1eq) of 3-chloropropionyl chloride, after the dropwise addition, keep warm for 3 hours. Add 466.7g (3.5mol, 1.75eq) of aluminum trichloride, 163g of sodium chloride and 23.3g of potassium chloride in molten state, and heat to 135°C for 4h. Sampling HPLC detects that there is no intermediate residue, the reaction solution is added to 3700g of ice water for hydrolysis, filtered, and dried to obtain 330g of black solid, which is dissolved in 1000mL of methanol and refluxed, filtered hot, and the filtrate is reheated to reflux, 30g of activated carbon is added, filtered hot, and the filtrate The temperature was lowered and crystallized to obtain 242.9 g of a yellow solid with a yield of 72.9% and HPL...

Embodiment 2

[0039] Embodiment 2 (traditional process)

[0040]

[0041] Put 227.4g (2.02mol, 1.01eq) of chlorobenzene into the reaction bottle, cool down to 25-30°C, add 314.7g (2.36mol, 1.18eq) of aluminum trichloride under stirring, and after stirring for 10 minutes, control the dropwise temperature Slowly add 254g (2.0mol, 1eq) of 3-chloropropionyl chloride dropwise at 25-45°C, and heat to 70-80°C for 2 hours after the addition is complete. Sampling GC detects that 0.5% of the raw material 3-chloropropionyl chloride remains. Add 514.7g (3.86mol, 1.93eq) of aluminum trichloride and 57.3g (0.98mol, 0.49eq) of sodium chloride in molten state, and heat to 150-165°C for 3h. Sampling was performed by HPLC to detect that no intermediate remained. After the heat preservation was completed, the temperature was lowered to 105-110°C. The reaction solution was added to 3700g of ice water for hydrolysis, filtered, and dried to obtain 330g of a black solid. The crude product 330g was divided into ...

Embodiment 3

[0043]

[0044] Put 227.4g (2.02mol, 1.01eq) of chlorobenzene into the reaction bottle, cool down to 25-30°C, add 314.7g (2.36mol, 1.18eq) of aluminum trichloride under stirring, and after stirring for 10 minutes, control the dropwise temperature Slowly add 254g (2.0mol, 1eq) of 3-chloropropionyl chloride dropwise at 25-45°C, and heat to 70-80°C for 2 hours after the addition is complete. Sampling GC detects that 0.5% of the raw material 3-chloropropionyl chloride remains. Add 514.7g (3.86mol, 1.93eq) of aluminum trichloride and 57.3g (0.98mol, 0.49eq) of sodium chloride in molten state, and heat to 150-165°C for 3h. Sampling was performed by HPLC to detect that there was no residual intermediate, and after the heat preservation was completed, the temperature was lowered to 105-110° C., and 2000 g of 4% hydrochloric acid prepared in advance was added dropwise. Control the dropping temperature at 90-95°C, stir for 10 minutes, let stand for 30 minutes, and separate the lower...

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Abstract

The invention discloses an improved process method for preparing 5-chloroindanone, and belongs to the technical field of organic synthesis. The method comprises the following steps: mixing chlorobenzene with anhydrous aluminum trichloride, adding 3-chloropropionyl chloride, and carrying out Friedel-Crafts acylation reaction to obtain 3,4'-dichloropropiophenone; then carrying out catalytic cyclization under the condition of anhydrous aluminum trichloride / sodium chloride or tri(pentafluorophenyl)borane; and after the reaction is finished, washing the product with water and directly rectifying the product to obtain the 5-chloroindanone. According to the process disclosed by the invention, the direct distillation is performed after water washing, so that no subsequent operation is performed, the operation steps are reduced, the production time is shortened, the production cost is saved, the extraction effect of the product is greatly improved, the yield of the product is improved by 15% or above, low-boiling-point substances and high-boiling-point substances can be effectively removed through direct distillation, and the content of the product is improved to 99.5% or above; meanwhile, cyclization is carried out under catalysis of tri(pentafluorophenyl)borane, so that the total dosage of aluminum trichloride can be reduced, the cyclization reaction temperature is reduced, the generation of tar is reduced, and the yield of the product is improved.

Description

technical field [0001] The invention relates to an improved process for preparing 5-chloroindanone, which belongs to the technical field of organic synthesis. Background technique [0002] 5-Chloroindanone, CAS: 42348-86-7, English name: 5-Chloro-1-indanone. 5-Chlorindanone is an important biomedical intermediate, pesticide intermediate and an important intermediate for the preparation of metallocene complexes. Among them, 5-chloroindanone as the mother nucleus is an important heavy intermediate of indoxacarb. [0003] Indoxacarb is a carbamate insecticide developed by DuPont in 1992 and registered in 2001. Its common name is Indoxacarb and its trade name is Vatar. Its chemical structural formula is as follows: [0004] [0005] Different from traditional carbamate insecticides, indoxacarb is a sodium ion channel inhibitor, which mainly blocks the sodium ion channel in the nerve cells of pests, causing the nerve cells to lose their function, resulting in paralysis and ...

Claims

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Application Information

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IPC IPC(8): C07C45/61C07C49/697C07C45/46C07C49/80
CPCC07C45/61C07C45/46C07C2602/08C07C49/697C07C49/80Y02P20/584
Inventor 李军
Owner 上海鼎素精细化工有限公司
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