A kind of synthetic method of vitamin c ethyl ether

A synthetic method and technology of vitamins, applied in chemical instruments and methods, bulk chemical production, organic compound/hydride/coordination complex catalysts, etc., can solve low yield, high production cost and limited vitamin Problems such as the popularization and application of C ethyl ether have achieved the effects of high product yield, green production process and improved reaction rate.

Active Publication Date: 2022-02-25
SHANGHAI JAKA BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The process for producing vitamin C ethyl ether disclosed in the prior art either has a low yield or requires a large amount of resin in the production process, resulting in high production costs (the current price is about 800,000 yuan / ton), Limit the popularization and application of vitamin C ethyl ether

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] A method for synthesizing vitamin C ethyl ether, comprising the steps:

[0023] 1) Weigh 176g (1mol) L-ascorbic acid, 1056g ethyl acetate and mix with 105.6g acetone acetal, add 1.06g stannous chloride and 1.41g tetrabutylammonium bromide, heat to 40°C, stir the reaction until the solution is clear to obtain vitamin C protector;

[0024] 2) The reaction solution obtained in step 1) is distilled to remove solvent ethyl acetate and incompletely reacted acetone dimethyl acetal, then add 1.2 mol of triethylamine and 1.1 mol of diethyl carbonate, and then add 1100 g of Water ethanol, stirred and reacted at 45 ° C for 5 hours to obtain vitamin C protected etherate

[0025] 3) adding a 10% hydrochloric acid aqueous solution (the mass ratio of HCl and water is 1:9) to the reaction solution in step 2), adjusting the pH to 2.0, heating to 55°C, and stirring for 3 to 4 hours, remove the protecting group;

[0026] 4) The pH of the reaction mixture in step 3) was adjusted to 5.8,...

Embodiment 2

[0028] A method for synthesizing vitamin C ethyl ether, comprising the steps:

[0029] 1) Weigh 176g (1mol) L-ascorbic acid, 1056g ethyl acetate and mix with 105.6g acetone acetal, add 0.7g stannous chloride and 0.7g tetrabutylammonium bromide, heat to 45°C, stir the reaction until the solution is clear to obtain vitamin C protector;

[0030] 2) The reaction solution obtained in step 1) was distilled to remove the solvent ethyl acetate and the unreacted acetone acetal, then add 1.5 mol of triethylamine and 1.3 mol of diethyl carbonate, and then add 1050 g of water and ethanol, stirring and reacting at 45 ° C for 4 hours to obtain the etherate of vitamin C protection body

[0031] 3) adding a mass fraction of 10% hydrochloric acid aqueous solution to the reaction solution in step 2), adjusting the pH to 3.0, heating to 55° C., stirring and reacting for 3 to 4 hours, and removing the protective group;

[0032] 4) The pH of the reaction mixture in step 3) was adjusted to 5.8, a...

Embodiment 3

[0034] A method for synthesizing vitamin C ethyl ether, comprising the steps:

[0035] 1) Mix by weighing 176g (1mol) L-ascorbic acid, 1056g ethyl acetate and 105.6g acetone acetal, add 1.76g stannous chloride and 1.76g tetrabutylammonium bromide, heat to 43°C, and stir to react to The solution is clarified to obtain vitamin C protector;

[0036] 2) The reaction solution obtained in step 1) is distilled to remove solvent ethyl acetate and incompletely reacted acetone acetal, then add 1.5 mol of triethylamine and 1.3 mol of diethyl carbonate, and then add 1000 g of water and ethanol, and the reaction was stirred at 43 ° C for 5.5 hours to obtain the etherate of vitamin C protective body.

[0037] 3) adding a mass fraction of 10% hydrochloric acid aqueous solution to the reaction solution in step 2), adjusting the pH to 2.8, heating to 60° C., stirring and reacting for 3 to 4 hours, and removing the protective group;

[0038] 4) The pH of the reaction mixture in step 3) was ad...

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PUM

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Abstract

The invention discloses a method for synthesizing vitamin C ethyl ether with reasonable process design, mild reaction conditions, high product yield, no need to use a resin catalyst, and an environmentally friendly production process. The method comprises the following steps: 1) using stannous chloride and tetrabutylammonium bromide as catalysts to synthesize vitamin C protected body; 2) synthesizing vitamin C protected body etherate; 3) using hydrochloric acid solution to adjust pH to remove protecting group; 4) The product was purified by recrystallization from a weakly polar solvent. In the invention, through the synergistic effect between the stannous chloride and the phase transfer catalyst tetrabutylammonium bromide, the contact between the reactants is more sufficient and the reaction speed is increased.

Description

technical field [0001] The invention belongs to the technical field of cosmetic chemistry, and specifically relates to a method for synthesizing vitamin C ethyl ether. Background technique [0002] Vitamin C ethyl ether (Chinese name: 3-O-ethyl ascorbic acid, English name: 3-O-Ethyl AscorbylEther), also known as Ethyl ascorbic acid, CAS No: 86404-04-8. Vitamin C ethyl ether replaces the 3-position hydroxyl of vitamin C with ethyl, which can protect vitamin C from being oxidized and destroy its activity, and has both hydrophilic and lipophilic properties. Among various vitamin C derivatives, vitamin C ethyl ether has the highest vitamin C content and the smallest molecular weight, which is more conducive to entering the skin and being easily absorbed by the human body. Often used as an anti-aging and whitening agent in high-end cosmetics. [0003] The patent application with the patent number of CN200710130927.7 discloses a separation and purification method for preparing 3...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/62B01J31/26B01J31/02
CPCC07D307/62B01J31/26B01J31/0239Y02P20/55
Inventor 田军刘青高雅卢伊娜
Owner SHANGHAI JAKA BIOTECH CO LTD
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