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Preparing method of beta,beta'-dithiobis(dihydrocinnamicacid)

A technology of dihydrocinnamic acid and disulfide, which is applied in the field of preparation of high-purity β,β'-disulfide, can solve the problems of complicated operation and difficult to guarantee yield, and achieves the effect of simple operation and reduction of side reactions.

Active Publication Date: 2016-06-15
SHANGHAI BETTERSYN BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the synthesis methods of β,β'-dithiobis(dihydrocinnamic acid) are rarely reported, and the synthesis of similar compounds often uses special catalysts, the operation is complicated, and the yield is difficult to guarantee

Method used

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  • Preparing method of beta,beta'-dithiobis(dihydrocinnamicacid)
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  • Preparing method of beta,beta'-dithiobis(dihydrocinnamicacid)

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Add 36.4g of 3-mercapto-3-phenylpropionic acid (200mmol), 72mL of 2.8mol / L sodium hydroxide solution (NaOH200mmol), 0.1g of iodine, and 128g of water into a three-necked flask equipped with a stirrer thermometer. The temperature was lowered to 5° C., and 22.7 g of 30% hydrogen peroxide was added dropwise. Incubate for 1 h to complete the reaction. After the reaction, add 0.5 g of sodium bisulfite to quench, and add hydrochloric acid to adjust the pH to 3-5. After filtering and drying, 34 g of β, β'-dithiobis(dihydrocinnamic acid) was obtained, and the yield reached 94%. The obtained β, β'-dithiobis(dihydrocinnamic acid) is analyzed, and its liquid chromatography content is 99.88% (HPLC, in220nm), and the specific results are as follows figure 2 Shown, LCMS: 361[M-H] - ; H-NMR results such as figure 1 as shown, 1 HNMR (CDCl 3 ,400Hz)7.30-7.39(m,10H),4.39-4.45(dd,2H,J=8Hz),3.42-3.48(dd,1H,J=8Hz),3.25-3.32(dd,1H,J=8Hz) ,2.95-3.00(m,2H).

Embodiment 2

[0033] Add 36.4g of 3-mercapto-3-phenylpropionic acid (200mmol), 0.364g of barium oxide, and 200g of water into a three-necked flask equipped with a stirrer thermometer, and gradually add potassium carbonate to adjust the pH of the reaction solution to 8. The temperature was lowered to 10° C., and 172 g of a 13% sodium hypochlorite solution (300 mmol of sodium hypochlorite) was added dropwise. Incubate for 1 h to complete the reaction. After the reaction, add 0.5 g of sodium bisulfite to quench, and add hydrochloric acid to adjust the pH to 3-5. After filtering and drying, β,β'-dithiobis(dihydrocinnamic acid) was obtained, and the yield and identification results were similar to those of Example 1.

Embodiment 3

[0035] Add 36.4g of 3-mercapto-3-phenylpropionic acid (200mmol), 0.364g of iron oxide, and 75g of water into a three-necked flask equipped with a stirrer thermometer, and gradually add potassium hydroxide to adjust the pH of the reaction solution to 9. The temperature was lowered to 0° C., and 250 mmol of nitric acid (10% aqueous nitric acid solution was used) was added dropwise. Incubate for 1 h to complete the reaction. After the reaction, add 0.5 g of sodium bisulfite to quench, and add hydrochloric acid to adjust the pH to 3-5. After filtering and drying, β,β'-dithiobis(dihydrocinnamic acid) was obtained, and the yield and identification results were similar to those of Example 1.

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Abstract

The invention relates to the field of organic synthesis, in particular to a preparing method of high-purity beta,beta'-dithiobis(dihydrocinnamicacid). The invention provides a preparing method of the beta,beta'-dithiobis(dihydrocinnamicacid), which comprises the following steps: taking 3-sulfydryl-3 phenylpropionic acid as a raw material, reacting in the presence of an oxidant and a catalyst in an environment of pH being 6-12 to generate the beta,beta'-dithiobis(dihydrocinnamicacid), wherein the reaction is performed in the presence of a reaction solvent being water. When the preparing method is used for synthesizing the beta,beta'-dithiobis(dihydrocinnamicacid), the water is used as the solvent, generation of side reactions in the reaction is reduced, waste liquid has no poison and harm, and operation is simple. The product is separated by adjusting to acidity with acids after the reaction, and the beta,beta'-dithiobis(dihydrocinnamicacid) with the purity up to 99.88% can be obtained by filtering.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of high-purity β,β'-dithiobis(dihydrocinnamic acid). Background technique [0002] β,β'-dithiobis(dihydrocinnamic acid) (compound of formula I, CASNo.63684-32-2) is an important chemical product, which can be used as a photosensitive agent in photosensitive materials, and this product can also be used as The key intermediate for the synthesis of sulfur-containing metal chelating agents. [0003] At present, the synthesis methods of β, β'-dithiobis(dihydrocinnamic acid) are rarely reported, and the synthesis of similar compounds often uses special catalysts, the operation is complicated, and the yield is difficult to guarantee. [0004] Contents of the invention [0005] In view of the shortcomings of the prior art described above, the purpose of the present invention is to provide a method for preparing high-purity β,β'-dithiobis(dihydrocinnamic acid), ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/56C07C319/24
CPCC07C319/24C07C323/56
Inventor 刘伟马钰李文龙彭少平何其中
Owner SHANGHAI BETTERSYN BIOTECH
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