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Process for preparing high-optical-purity R-(+)-2-chloropropionic acid through ester exchange method

A technology of chloropropionic acid and transesterification, which can be applied in the preparation of carboxylate, carboxylate/lactone, and oxygen-containing compounds, etc., can solve the problems of high production cost, many chiral impurities, hindering the progress of the reaction, and the like, To achieve the effect of short production cycle, good catalytic effect and reduction of tailings

Active Publication Date: 2015-02-25
HUBEI BIOCHEM PHARMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] CN103435469A provides a kind of preparation method of preparing high optical purity R-(+)-2-chloropropionic acid, utilizes 10% sulfuric acid to hydrolyze 2-chloropropionic acid methyl ester, and its yield is 86%, has not been reported in the patent Its optical purity; but it is hydrolyzed with sulfuric acid, the oxidizing property is too strong, the corrosiveness is too strong, it is easy to oxidize carbon-containing compounds when the temperature rises, and the raw materials are lost, the reaction liquid becomes viscous, the yield is reduced, and isomerism occurs body, affecting its optical purity; and the carbon compounds produced hinder the reaction, and are difficult to handle, polluting the environment, and there are a large number of by-product tails that need post-processing
However, using sodium hydroxide to hydrolyze under alkaline conditions produces more chiral impurities, and the total yield is only 61.93%. The yield is too low and the cost of industrial production is high.
There is also a chromatographic resolution method, which mainly adopts the separation of 2-chloropropionic acid optical isomers on the chirality of cyclodextrin or cyclodextrin derivatives. This type of method is mainly used for analysis and detection, and is not suitable for industrial use. Production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] ⑴ Add 600g of ethyl chloropropionate into the reactor equipped with stirring, thermometer, spherical condenser, electric heating mantle, and tail gas absorption device, turn on the stirrer, and add 1200g with a mass fraction of 94% under stirring conditions. 180g of formic acid and 732 resin treated with acid and alkali, slowly increase the temperature to 54°C, and collect the ethyl formate fraction; when the mass of the collected ethyl formate fraction is about 300g, continue to increase the temperature and collect the 85°C~108°C fraction. The distillate is mainly formic acid; after the reaction, the material and the resin are filtered and separated, and the resin is returned to the system for the next hydrolysis separation process, which is recycled and reused.

[0018] ⑵Connect the reactor to a vacuum pump, evacuate and reduce pressure to -0.095MPa~-0.01MPa, start to heat up, and collect the fraction below 108°C. This fraction is divided into unreacted ethyl chloropropio...

Embodiment 2

[0020] ⑴Add 700g of ethyl chloropropionate into the reactor equipped with stirring, thermometer, spherical condenser, electric heating mantle, and exhaust gas absorption device, turn on the stirrer, add 1050g respectively, with a mass fraction of 94% under stirring 210g of formic acid and D001 strongly acidic cationic resin treated with acid and alkali, slowly increase the temperature to 54℃, and collect the ethyl formate fraction; when the mass of the collected ethyl formate fraction is about 350g, continue to increase the temperature and collect 85℃~108℃ Fraction, this fraction is mainly formic acid; after the reaction, the material and the resin are filtered and separated, and the resin is returned to the system for the next hydrolysis and separation process, which is recycled and reused.

[0021] (2) Connect the reactor to a vacuum pump, evacuate and reduce pressure to -0.095MPa~-0.01MPa, start to heat up, collect fractions below 108°C, this fraction is divided into unreacted ...

Embodiment 3

[0023] ⑴Add 400g of ethyl chloropropionate into the reactor equipped with stirring, thermometer, spherical condenser, electric heating mantle and tail gas absorption device, turn on the stirrer, and add 1600g of 94% mass fraction under stirring conditions. 240g of formic acid and 734 strongly acidic cationic resin treated with acid and alkali, slowly increase the temperature to 54°C, and collect ethyl formate fraction; when the collected ethyl formate fraction is about 200g, continue to increase the temperature and collect the 85°C~108°C fraction , This fraction is mainly formic acid; after the reaction, the material and the resin are filtered and separated, and the resin is returned to the system for the next hydrolysis and separation process, which is recycled and reused.

[0024] ⑵Connect the reactor to a vacuum pump, evacuate and reduce pressure to -0.095MPa~-0.01MPa, start to heat up, and collect the fraction below 108°C. This fraction is divided into unreacted ethyl chloropr...

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Abstract

The invention discloses a process for preparing high-optical-purity R-(+)-2-chloropropionic acid through an ester exchange method. The process comprises the following steps: placing ethyl chloropropionate in a reactor, sequentially adding formic acid with the mass fraction of 94% and strong-acid cation exchange resin under stirring, slowly heating to 54DEG C, extracting ethyl formate, continuously heating, and recovering formic acid; and forming a negative pressure after the recovery of formic acid, and extracting R-(+)-2-chloropropionic acid. The process has the advantages of simple technology, no strong acidic tails, environmental protection and short production period, and the optical purity and the yield of the prepared R-(+)-2-chloropropionic acid are not smaller than 99% and not smaller than 90% respectively.

Description

Technical field [0001] The invention relates to a preparation method of intermediates such as pesticides, dyes, medicines, nutritional supplements, etc., in particular to a preparation method of high optical purity R-(+)-2-chloropropionic acid prepared by a transesterification method. Background technique [0002] R-(+)-2-Chloropropionic acid is one of the important intermediates for the synthesis of pesticides, dyes, medicines, nutritional supplements, etc. Its application involves many areas of the national economy and people’s daily life, and is an important product . Since optical enantiomers are different in biological activity, toxicity, pharmacology, etc., the preparation of a single enantiomer is extremely important. In recent years, the chiral medicine market has developed rapidly, and the research and application of single enantiomer medicines are also More and more important, so the preparation of high optical purity R-(+)-2-chloropropionic acid is of great significa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C27/00C07C51/09C07C53/19C07C67/10C07C69/06
CPCC07C27/00C07C51/09C07C67/10C07C53/19C07C69/06
Inventor 张闻艺胡凯黄宏平
Owner HUBEI BIOCHEM PHARMA TECH
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