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A kind of synthetic method of pesticide intermediate (s)-(-)-2-chloropropionic acid

A synthetic method and an intermediate technology, which are applied in the field of synthesis of the pesticide intermediate - 2-chloropropionic acid, can solve the problems of unfavorable industrial production, cumbersome steps, cumbersome post-treatment, etc., and achieve the improvement of chiral induction ability and inhibition of The formation of enantiomers and the effect of inhibiting the formation of racemates

Active Publication Date: 2021-02-19
江苏丰山生化科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In the synthetic route with (R)-methyl lactate as the starting material, although the optical purity of the obtained product is higher, the starting materials used are relatively expensive, which is not conducive to industrial production, and the synthesis process needs to go through Several steps of chlorination, alkali hydrolysis and acidification, the route is long and the post-treatment is cumbersome
In the existing synthetic route with (S)-2-alanine as the starting raw material, although the raw material is easy to get and the technological process is short, its yield is low, and the optical purity of the product is only about e.e. 95%
[0011] Chinese invention patent CN102344355A discloses a method for resolving racemic 2-chloropropionic acid by a chiral resolving agent to obtain a chiral compound (S)-2-chloropropionic acid. The chiral purity of the obtained product is relatively high. High, but the chiral resolving agent is expensive, the resolution cost is high, and the steps are cumbersome, it is difficult to promote in industrial production

Method used

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  • A kind of synthetic method of pesticide intermediate (s)-(-)-2-chloropropionic acid
  • A kind of synthetic method of pesticide intermediate (s)-(-)-2-chloropropionic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Add 365.0g (3.00mol) of hydrochloric acid, 0.87g (0.007mol) of cobalt chloride, and 10.11g (0.067mol) of tartaric acid into a 1000ml four-neck flask. After feeding, add 60.0g of (S)-2-alanine (0.667mol), then stirred for 1 hour, cooled to 0°C; 414.0g (1.200mol) of sodium nitrite aqueous solution was added dropwise at a concentration of 20%, added dropwise for 10 hours, and after the addition was completed, it was incubated at 0°C for 1 hour. The reaction is over.

[0035] The (S)-(-)-2-chloropropionic acid generated by the reaction was extracted with 200ml×3 dichloromethane solvent. After the extraction was completed, the organic phases were combined and the solvent was distilled to obtain the product (S)-(-)-2-chloropropane Acid 62.1g, content 99.4%, e.e 99.3%, yield 85.2%.

Embodiment 2

[0037] Add 365.0g (3.00mol) of hydrochloric acid into a 1000ml four-necked flask, then add 8.54g (0.067mol) of ferrous chloride and 1.01g (0.007mol) of tartaric acid, and then add (S)-2-propylamine Acid 60.0g (0.667mol), then stirred for 1 hour, cooled to 0°C, added dropwise 242.0g (1.334mol) of 38% sodium nitrite aqueous solution, added dropwise for 3 hours, and kept at 0°C after the dropwise addition After 1 hour, the reaction was complete.

[0038] The (S)-(-)-2-chloropropionic acid generated by the reaction was extracted with 60ml×2 methyl isobutyl ketone solvent. After the extraction was completed, the organic phases were combined and the solvent was distilled to obtain the product (S)-(-)-2 - chloropropionic acid 62.4g, content 99.1%, e.e 99.1%, yield 85.4%.

Embodiment 3

[0040] Add 365.0g (3.00mol) of hydrochloric acid to a 1000ml four-necked flask, then add 4.36g (0.033mol) of nickel chloride and 7.82g (0.033mol) of camphorsulfonic acid, and then add (S)-2-propane Amino acid 60.0g (0.667mol), then stirred for 1 hour, cooled to 0°C, added dropwise 307.0g (2.000mol) of 45% sodium nitrite aqueous solution, added dropwise for 5 hours, and kept warm at 0°C after the addition After 1 hour, the reaction was complete.

[0041] Use 250ml×3 toluene solvent to extract the (S)-(-)-2-chloropropionic acid generated by the reaction. After the extraction is complete, combine the organic phases and distill the solvent to obtain the product (S)-(-)-2-chloropropionic acid 62.2g, content 99.3%, e.e 99.2%, yield 85.2%.

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Abstract

The invention relates to a synthesis method of pesticide intermediate (S)-(-)-2-chloropropionic acid. The method comprises the step of enabling (S)-2-chloropropionic acid, used as a starting raw material, and sodium nitrite to be subjected to a diazo-reaction in presence of a catalyst and lewis acid so as to obtain the (S)-(-)-2-chloropropionic acid product. The synthesis method improves the yield, content and optical purity of the product, reduces the production cost, and improves the product quality; the optical purity of the obtained (S)-(-)-2-chloropropionic acid is e.e. 99% or above, andthe reaction yield is 85% or above; the synthesis method is short in reaction route and simple in aftertreatment, and has a great guiding significance for process amplification and production.

Description

technical field [0001] The invention belongs to the field of pesticide intermediate production, in particular to a method for synthesizing the pesticide intermediate (S)-(-)-2-chloropropionic acid. Background technique [0002] With the development of stereochemistry and the introduction of the concept of atom economy, the research of pesticide science has paid enough attention to the stereoisomerism of molecules, and the development of racemic pesticides to monochiral forms has become the trend of pesticide creation. [0003] Observing the structural components of living organisms from the molecular level, most of them have chiral characteristics, and enzymes that catalyze biochemical processes in organisms are all stereospecific, so optically active pesticides often have high activity. [0004] Aryloxypropionic acid herbicides are a new class of optically active herbicides developed after the 1970s. They have high efficiency, low toxicity, wide herbicidal spectrum, high se...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/363C07C51/48C07C53/19C07C245/20
CPCC07B2200/07C07C51/363C07C51/48C07C245/20C07C53/19
Inventor 罗世英王晋阳叶茂王瑞彪刘盼豆飞扬姚金莉彭慧珍李俊卿王波单永祥殷平殷凤山
Owner 江苏丰山生化科技有限公司