Method for synthesizing imidacloprid intermediate morpholinyl propylene by micro-channel reactor

A micro-channel reactor, morpholine propylene technology, applied in the direction of organic chemistry, can solve the problems of low production cost, poor heat transfer effect, high energy consumption, etc., to eliminate back mixing, improve reaction selectivity, and accurate temperature control. Effect

Active Publication Date: 2020-07-10
JIANGSU YANGNONG CHEM GROUP +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] In order to solve the problems of high energy consumption, poor heat transfer effect and low yield in the existing synthesis enamine process, the present invention provides a continuous flow method in microchannel The method for preparing enamine by using morpholine and n-propionaldehyde as raw materials in a reactor, compared with the existing technology, has mild reaction temperature, continuous production, and completes the reaction in a very short time, and has the advantages of low production cost and low raw material The advantages of high utilization rate and high product selectivity

Method used

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  • Method for synthesizing imidacloprid intermediate morpholinyl propylene by micro-channel reactor
  • Method for synthesizing imidacloprid intermediate morpholinyl propylene by micro-channel reactor

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Effect test

Embodiment 1

[0027] Pump morpholine and n-propionaldehyde into the microchannel reactor according to the molar ratio of 10.0:1, and react at a reaction temperature of 20°C and a reaction pressure of 0.2MPa. By adjusting the flow rate of the feed pump, the residence time of the reaction material is controlled to 200s. The flow rate of the mixed solution is 0.12ml / s. The product was incubated at 20°C for 1.5hr, and after the incubation was completed, it was dehydrated under negative pressure at a vacuum degree of 3kPa, and the final liquid temperature was 80°C. The dehydrated product was subjected to negative pressure rectification at a vacuum degree of 2.5kPa, and the liquid temperature at the end point was 130°C to obtain the enamine product for the next reaction. The finished product of enamine was analyzed, and the enamine yield was 89.3% based on n-propionaldehyde.

Embodiment 2

[0029] Pump morpholine and n-propionaldehyde into the microchannel reactor at a molar ratio of 4.0:1, and react at a reaction temperature of 40°C and a reaction pressure of 2.0 MPa. The residence time of the reaction materials is controlled to be 10s by adjusting the flow rate of the feed pump. The flow rate of the mixed solution is 2.4ml / s. The product was incubated at 40°C for 3 hours, and after the incubation was completed, it was dehydrated under negative pressure at a vacuum degree of 0.1kPa, and the liquid temperature at the end point was 40°C. After further dehydration, the product was subjected to negative pressure rectification under a vacuum degree of 2.1kPa, and the liquid temperature at the end point was 120°C to obtain the finished enamine for the next reaction. The finished product of enamine was analyzed, and the enamine yield was 97.6% based on n-propionaldehyde.

Embodiment 3

[0031] Pump morpholine and n-propionaldehyde into the microchannel reactor according to the molar ratio of 2.4:1, and react at a reaction temperature of 50°C and a reaction pressure of 0.8MPa. By adjusting the flow rate of the feed pump, the residence time of the reaction materials is controlled to be 15s. The flow rate of the mixed solution is 1.5ml / s. The product was incubated at 50°C for 2 hours, and after the incubation was completed, it was dehydrated under negative pressure at a vacuum degree of 0.3kPa, and the final liquid temperature was 45°C. The dehydrated product was subjected to negative pressure rectification under a vacuum degree of 1.3kPa, and the liquid temperature at the end point was 105°C to obtain the finished enamine for the next reaction. The enamine finished product was analyzed, and the enamine yield was 99.3% based on n-propionaldehyde.

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Abstract

The invention discloses a method for synthesizing enamine by adopting a micro-channel reactor. The method comprises the following steps: simultaneously pumping morpholine and n-propionaldehyde into the micro-channel reactor according to a molar ratio of (2.0-10.0): 1, and reacting at a certain reaction temperature under a certain reaction pressure for a certain reaction time; and then carrying outheat preservation, negative-pressure dehydration and negative-pressure rectification to obtain an enamine finished product. The invention also provides a production method of imidacloprid. The production method comprises the following steps: cyclizing enamine to prepare a cyclobutyl compound, and carrying out ammonolysis on the cyclobutyl compound to prepare pyridone; carrying out chlorine addition and phosgene chlorination on pyridone to prepare 2-chloro-5-methylpyridine; carrying out chlorination on the 2-chloro-5-methylpyridine by using chlorine gas to synthesize 2-chloro-5-chloromethylpyridine; and synthesizing imidacloprid from a 1, 2-chloro-5-chloromethylpyridine/N, N-dimethylformamide solution and imidazolidine.

Description

technical field [0001] The invention belongs to the technical field of organic chemical industry, and relates to a method for synthesizing imidacloprid intermediate morpholinopropene through a microchannel reactor. Background technique [0002] Imidacloprid (chemical name: 1-(6-chloropyridin-3-pyridylmethyl)-N-nitroimidazolidin-2-ylamine) is the world’s largest neonicotinoid insecticide with excellent Insecticidal activity, low mammalian toxicity, and rapid development due to its high efficiency, broad spectrum, and good environmental compatibility, it can be used in rice, wheat, corn, fruit trees and other crops. At present, the main production processes of domestic imidacloprid include benzylamine-n-propionaldehyde method, cyclopentadiene-acrolein method and morpholine-n-propionaldehyde method. [0003] Benzylamine-n-propionaldehyde method: use benzylamine as raw material to synthesize N-benzyl-N-propenylacetamide with n-propionaldehyde and acetic anhydride respectively, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/023C07D295/03
CPCC07D295/023C07D295/03
Inventor 丁克鸿徐林王怡明王根林史雪芳聂庆超
Owner JIANGSU YANGNONG CHEM GROUP
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