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Method for producing 3-mercaptopropionic acid, and carbonic acid ester composition having mercapto group using same, and method for producing thiourethane-based optical materials

A technology of mercaptopropionic acid and its manufacturing method, which is applied in optics, organic chemistry, optical components, etc., can solve problems such as complex manufacturing process, difficult manufacturing, complex reaction steps, etc., and achieve simple manufacturing process, excellent yield, and excellent hue Effect

Inactive Publication Date: 2014-09-17
KOC SOLUTION
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still disadvantages of complex manufacturing process
[0006] Chinese patent CN101125827A discloses a method for converting thiodipropionic acid (dimer) into 3-mercaptopropionic acid (multimer), which utilizes iron and strong acid to Acidic treatment requires relatively severe reaction conditions, and there are problems with the composition ratio of the product and by-products.
However, the method provided by this patent uses acrylonitrile and sodium hydrogen sulfide to form thiodimercaptopropionitrile (dimer), to which sodium hydrogen sulfide and caustic soda are added again to obtain 2-cyanogen Sodium thiolate (2-cyanoethanethiolate natrium) (Monomer), the sodium 2-cyanoethanethiolate is refluxed in strong acid (hydrochloric acid), and the nitrile needs to be converted into a carboxylic acid group The steps are not only complicated in its reaction steps and difficult to manufacture, but also under the condition of refluxed hydrochloric acid to convert nitrile into carboxylic acid groups without separating 3-mercaptopropionitrile, resulting in low yield of product and occurrence of The problem of a lot of 3-mercaptopropionitrile remaining due to unreacted

Method used

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  • Method for producing 3-mercaptopropionic acid, and carbonic acid ester composition having mercapto group using same, and method for producing thiourethane-based optical materials
  • Method for producing 3-mercaptopropionic acid, and carbonic acid ester composition having mercapto group using same, and method for producing thiourethane-based optical materials
  • Method for producing 3-mercaptopropionic acid, and carbonic acid ester composition having mercapto group using same, and method for producing thiourethane-based optical materials

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0070] 3-Mercaptopropionic acid (MPA-1)

[0071] After installing a stirrer, a thermometer, and a condenser in a 1-liter 4-zone flask, put NaSH.xH 2 O (70%, 162.00g, 2.00 moles), add 160g of water, and stir for 30 minutes at 30°C to dissolve completely. Next, maintaining a temperature of 35° C., acrylonitrile (106.12 g, 2.00 mol) was slowly added dropwise. After heating and starting the reaction, all the acrylonitrile was charged, and then left at 60°C for 8 hours to obtain sodium 2-cyanoethanethiolate. The product was confirmed by GC analysis. The starting substance completely disappeared, and the product sodium 2-cyanoethanethiolate was neutralized to obtain 3-mercaptopropionitrile, which was confirmed by GC analysis. After the reaction was completed, the temperature was lowered to 10° C., and concentrated hydrochloric acid was slowly added dropwise while stirring for neutralization. After the dropwise addition, the stirring was stopped, the nitriles in the upper layer ...

Synthetic example 2

[0073] 3-Mercaptopropionic acid (MPA-2)

[0074] After installing a stirrer, a thermometer, and a condenser in a 1-liter 4-zone flask, put NaSH.xH 2 O (70%, 177.79g, 2.22 moles), add 160g of water, and stir for 30 minutes at 40°C to dissolve completely. Next, maintaining a temperature of 35° C., acrylonitrile (106.12 g, 2.00 mol) was slowly added dropwise. Heat up and start to react. After all the acrylonitrile is put in, place it at 50°C for 10 hours, stir at this temperature to obtain sodium 2-cyanoethanethiolate, and neutralize it to obtain 3-mercaptopropionitrile. 3-Mercaptopropionitrile was confirmed by GC analysis. When the reaction is finished, the temperature is lowered to 10°C, and neutralized by concentrated hydrochloric acid, and the generated 3-mercaptopropionitrile exists in the upper layer—the organic layer. The lower layer—the aqueous layer was removed, and concentrated hydrochloric acid was added to the upper layer 3-mercaptopropionitrile. React at 60°C f...

Synthetic example 3

[0081] Trimethylolpropane Tris(3-Mercaptopropionate) (TMPMP-2)

[0082]Install a stirrer, a thermometer and a Dean-stark device (Dean-stark) on a 1-liter 4-zone flask, add 1 mole (67.08 g) of trimethylol propane, and put the 3-mercaptopropionic acid (MPA) obtained in Synthesis Example 1 -1) 3 moles (318.42 g), 100 g of toluene was added as a solvent, and it was placed in an oil heating pot and heated. The oil temperature was 150°C. When the internal temperature was around 120°C, water began to be generated, and the reaction continued for 24 hours. After that, the occurrence of water was hardly observed, and the excess 3-mercaptopropionic acid was distilled under reduced pressure in the solvent and recovered. As a result of LC analysis, unreacted trimethylpropane did not appear, the purity of the product was 88%, and 195.28 g of the product was obtained. The resulting product has a refractive index (nE) of 1.518 and a hue of APHA14, and can be directly used as a polymeric ...

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Abstract

The present invention relates to a method for producing 3-mercaptopropionic acid and carbonic acid ester composition having mercapto group using same, and a method for producing thiourethane-based optical materials. The method for producing 3-mercaptopropionic acid according to the present invention does not include a post-processing treatment, which is necessitated by generation of a dimer such as thiodipropionitrile, thereby the process is simple and economical, and exhibits superior yield rate. Additionally, the carbonic acid ester composition produced with 3-mercaptopropionic acid produced using the method exhibit superior purity and coloring, and allows production at a low cost, and thus has the benefit of being usable as an inexpensive resin composition for urethane-based optical materials, and ptical materials thus produced exhibit excellent coloring. Thiourethane-based optical lenses having good coloring, obtained by means of the present invention, can replace existing lenses and be widely used in diverse fields.

Description

technical field [0001] The present invention relates to the production method of 3-mercapto propionic acid (3-mercapto propionic acid) and the production method of the carboxylic ester (carboxylic ester) with mercapto group and thiourethane system optical material using it, especially a kind of mercapto propionic acid A method for producing mercaptopropionic acid that can be produced at low cost because of its excellent yield and simple process. Background technique [0002] Mercapto carboxylic acid (mercaptopropionic acid) is suitable for cross linking agent of acrylic ester polymer and hardener of epoxy resin, used in synthetic resins such as optical lenses. In particular, it is possible to synthesize carboxylate compounds having various mercapto groups by performing esterification reaction with alcohols. [0003] U.S. Patent No. 5,008,432 discloses related technologies about adding hydrogen sulfide to unsaturated compounds such as acrylic acid to manufacture 3-mercaptopr...

Claims

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Application Information

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IPC IPC(8): C07C319/04C07C323/03C08L81/00
CPCC08L81/00C07C319/12C07C319/04C08G18/3206C08G18/4854C08G18/6511C08G18/6705C07C323/60C07C323/52C07C319/26C07C321/14G02B1/04
Inventor 张东奎卢守均金钟孝
Owner KOC SOLUTION
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