Unlock instant, AI-driven research and patent intelligence for your innovation.

Method for preparing precursor 2-chloro-2-chloromethyl-4-cyano butyraldehyde of Paichonghding intermediate

An intermediate, chloromethyl technology, applied in the field of synthesis of organic compounds, can solve the problems of cumbersome steps and high cost of reactants, and achieve the effect of increasing reaction yield, reducing production cost and improving product quality

Inactive Publication Date: 2014-06-18
江苏克胜集团股份有限公司 +1
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This reaction route has the problems of high cost of reactants and cumbersome steps

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing precursor 2-chloro-2-chloromethyl-4-cyano butyraldehyde of Paichonghding intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] In a 250ml three-neck round bottom flask, dissolve 20g (0.357mol) of acrolein in 200g of chloroform, control the temperature at -5 to 0°C, and then feed 25g of chlorine gas (0.357mol) within 2 to 3 hours. , take a sample to measure the normalized content of acrolein ≤ 0.5%, and the chlorination reaction ends. The reaction formula is as formula (1). After the residual chlorine in the chloroform solution was removed under negative pressure at low temperature, the solvent was evaporated under negative pressure, and then 41 g of the product 2,3-dichloropropanal was further evaporated, with a content of 98% and a yield of 89%.

[0026] The spectroscopic analysis result of chlorination addition reaction product is: 1 H NMR (60MHz, CDCl 3 ): 3.95 (d, J=7.0Hz, 2H, CH 2 ), 4.35~4.65 (d, 1H, CHCl), 9.6 (d, J=2.0Hz, 1H, CHO); HR-MS (EI, 1.08e3): M + for C 3 h 4 OCl 2 , calculated value: 126.970, measured value: 126.976.

[0027] In a 250ml three-necked round-bottomed flask...

Embodiment 2

[0030] In a 250ml three-neck round bottom flask, dissolve 20g (0.357mol) of acrolein in 100g of dichloroethane, control the temperature at -1 to 0°C, and then feed 25g of chlorine gas (0.357mol) within 2 hours. ), sampling and measuring the normalized content of acrolein ≤ 0.5%, the chlorination reaction is finished. After the residual chlorine in the chloroform solution was removed under negative pressure at low temperature, the solvent was evaporated under negative pressure, and then 41 g of the product 2,3-dichloropropanal was further evaporated, with a content of 98% and a yield of 89%. The spectroscopic analysis of the chlorination addition reaction product is consistent with the chemical formula.

[0031] Dissolve 40g (0.309mol) of 2,3-dichloropropanal in 200ml of xylene in a 250ml three-neck round bottom flask, then add 0.5g of sodium hydroxide and 0.69g of anhydrous sodium tert-butoxide, and control the temperature at 25- 25 g of acrylonitrile was added dropwise at 30...

Embodiment 3

[0033] In a 500ml three-neck round bottom flask, dissolve 20g (0.357mol) of acrolein in 400g of dichloroethane, control the temperature at -5 to -4°C, and then feed 25g of chlorine gas (0.357mol) within 3 hours. mol), sampling and measuring the normalized content of acrolein ≤ 0.5%, the chlorination reaction is over. After the residual chlorine in the chloroform solution was removed under negative pressure at low temperature, the solvent was evaporated under negative pressure, and then 41 g of the product 2,3-dichloropropanal was further evaporated, with a content of 98% and a yield of 89%. The spectroscopic analysis of the chlorination addition reaction product is consistent with the chemical formula.

[0034] In a 250ml three-necked round-bottomed flask, 40g (0.309mol) 2,3-dichloropropanal was dissolved in 200ml xylene, then 0.8g triethylamine, 0.6 gram (6.2mmol) anhydrous tert-butyl alcohol were added to control Add 25 grams of acrylonitrile dropwise at a temperature of 25...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides a method for preparing a precursor 2-chloro-2-chloromethyl-4-cyano butyraldehyde of a Paichonghding intermediate. The method comprises the following steps: 1) a chlorination addition reaction: introducing chlorine into an acrolein solution for reaction to generate 2, 3-dichloropropylaldehyde; and 2) a Michael addition reaction: dissolving the product obtained from the step 1) in an organic solvent for a reaction with acrylonitrile, with catalysts comprising organic or inorganic base, and tertiary butanol or salt thereof, to generate the 2-chloro-2-chloromethyl-4-cyano butyraldehyde. According to the present invention, a route comprising the first chlorination addition reaction to generate 2, 3-dichloropropylaldehyde, and the Michael addition reaction of the 2, 3-dichloropropylaldehyde with acrylonitrile to generate the 2-chloro-2-chloromethyl-4-cyano butyraldehyde is designed to improve reaction yield and reduce production cost; and appropriate solvents and catalysts are chosen to shorten time of the addition reactions, effectively inhibit by-products, and realize yield higher than 70%.

Description

technical field [0001] The invention belongs to the field of synthesis of organic compounds, and specifically relates to a method for preparing the precursor 2-chloro-2-chloromethyl-4-cyanobutyraldehyde of the intermediate of piperidendril. Background technique [0002] 2-Chloro-2-chloromethyl-4-cyanobutanal is the precursor of "2-chloro-5-chloromethylpyridine", which is the pesticide imidacloprid, acetamiprid, nitenpyram, piperazine It is an important intermediate of various neonicotinoid pesticides such as pyridine and cyclopyrid. The traditional method of preparing 2-chloro-2-chloromethyl-4-cyanobutyraldehyde is: dicyclopentadiene is cracked into "cyclopentadiene" and added to acrolein, and then Michael addition is carried out with acrylonitrile. Then it is cracked into "2-methylene-4-cyano-butanal", and finally chlorinated into "2-chloro-2-chloromethyl-4-cyanobutyraldehyde". The process route of this preparation method is long and cumbersome, the yield is 50%, and the ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/17C07C253/30
CPCY02P20/52
Inventor 徐其文吴重言吴静熊燕玲安礼涛金爱平
Owner 江苏克胜集团股份有限公司
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com