Preparation method for (R)-3-chloro-1,2-propanediol

A technology of propylene glycol and propylene oxide, applied in the preparation of organic compounds, hydrolysis preparation, chemical instruments and methods, etc., can solve the problems of less than 90%, multiple impurity peaks, affecting product economic benefits and market competition, etc. Achieve low moisture content, excellent yield, excellent overall purity

Inactive Publication Date: 2015-08-19
WUHU FOMAN BIOPHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, during the production of epichlorohydrin method, due to the influence of catalyst selection, use, feeding sequence, gradient temperature rise and other technical aspects, especially the influence of factors such as equipment selection and process conditions in the final distillation process, the purity of the obtained product is general. It is lower than 90%, especially the highest chiral purity can only reach 95%, and there are also problems such as improving the purity that will lead to a decline in yield (the current yield is between 65.2%-75%), which directly affects the economic benefits and benefits of the product. market competition
Although the vacuum scraper thin film evaporation method has been used in the separation of chloroglycerin, the problems of high purity and high impurity peaks after the main peak of chromatographic analysis and high impurity content have not been solved.

Method used

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  • Preparation method for (R)-3-chloro-1,2-propanediol
  • Preparation method for (R)-3-chloro-1,2-propanediol

Examples

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preparation example Construction

[0016] The present invention provides a preparation method of (R)-3-chloro-1,2-propanediol, the preparation method comprising:

[0017] 1) In the presence of an acid catalyst, (S)-3-chloro-1,2-propylene oxide and water are subjected to a ring-opening reaction to obtain a ring-opening mixture;

[0018] 2) Neutralizing the lye and the ring-opening mixture to obtain a neutralized mixture;

[0019] 3) Remove the water in the neutralized mixture, and then filter to obtain the filtrate;

[0020] 4) Fractional distillation of the filtrate at 30-35 Pa and 125-128°C to prepare (R)-3-chloro-1,2-propanediol.

[0021] In the present invention, the acidic catalyst can be any conventional acidic catalyst in the art, and the specific type can be selected in a wide range, but in order to make the prepared (R)-3-chloro-1,2-propanediol more Excellent overall purity (especially chiral purity), yield and low water content. Preferably, in step 1), the acidic catalyst is selected from one or more of sulfuri...

Embodiment 1

[0030] 1) At 108°C, 100 g of (S)-3-chloro-1,2-propylene oxide, 60 g of water and 1.5 g of sulfuric acid are subjected to a ring-opening reaction for 6 hours to obtain a ring-opening mixture;

[0031] 2) At 25° C., 15 g of sodium hydroxide aqueous solution (the mass fraction of sodium hydroxide is 5%) and 100 g of the ring-opening mixture are neutralized for 15 minutes to obtain a neutralized mixture (pH 7.0);

[0032] 3) Remove water from the neutralized mixture by distillation under reduced pressure (the water content of the mixture after water removal is 0.3%), and then filter to obtain a filtrate;

[0033] 4) Fractional distillation of the filtrate at 33 Pa and 126°C to prepare (R)-3-chloro-1,2-propanediol.

[0034] The hydrogen nuclear magnetic spectrum of (R)-3-chloro-1,2-propanediol see figure 1 , See figure 2 .

[0035] See Table 1 for the yield, total purity, chiral purity and water content parameters of (R)-3-chloro-1,2-propanediol in this example.

Embodiment 2

[0037] (R)-3-chloro-1,2-propanediol was prepared according to the method of Example 1, except that in step 3), the water content of the mixture after water removal was 0.1%.

[0038] The data of the hydrogen nuclear magnetic spectrum and the carbon nuclear magnetic spectrum of the (R)-3-chloro-1,2-propanediol are consistent with the characterization map in Example 1.

[0039] See Table 1 for the yield, total purity, chiral purity and water content parameters of (R)-3-chloro-1,2-propanediol in this example.

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Abstract

The invention discloses a preparation method for (R)-3-chloro-1,2-propanediol. The preparation method comprises the following steps: 1) subjecting (S)-3-chloro-1,2-epoxypropane and water to a ring-opening reaction in the presence of an acidic catalyst so as to obtain a ring-opening mixture; 2) subjecting alkali lye and the ring-opening mixture to a neutralization reaction so as to obtain a neutralization mixture; 3) removing water in the neutralization mixture and carrying out filtering so as to obtain a filtrate; and 4) fractionating the filtrate at a pressure of 30 to 35 pa and a temperature of 125 to 128 DEG C so as to prepare (R)-3-chloro-1,2-propanediol. The preparation method has excellent yield; and prepared (R)-3-chloro-1,2-propanediol has excellent total purity and low water content, and in particular, chiral purity of (R)-3-chloro-1,2-propanediol is as high as 99.5%.

Description

Technical field [0001] The invention relates to a method for preparing (R)-3-chloro-1,2-propanediol. Background technique [0002] (R)-3-chloro-1,2-propanediol is an important chlorinated substance of glycerol. It has a wide range of uses: it can be used as an intermediate in organic synthesis to synthesize pesticides, dyes, medicines, coatings, veterinary drugs, plasticizers, and surfactants. And printing and dyeing auxiliaries, etc.; can be used as solvents for the production of cellulose acetate, etc.; can also be used as important medical research reagents for the research of reproductive medicine; in the past ten years, it has been used in aerospace materials, non-ionic contrast agents, Electronic chemicals, catalyst synthesis and phase transfer catalyst applications are becoming more widely used, and the requirements for the purity and impurity content of chloroglycerol have also been greatly improved. Therefore, the industrial production of chloroglycerol has been more adv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C31/42C07C29/10C07C29/74C07C29/80
CPCC07C29/106C07C29/74C07C29/80C07C31/42
Inventor 苏福男
Owner WUHU FOMAN BIOPHARMA CO LTD
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