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Preparation method of acetylated sodium hyaluronate

A technology of sodium hyaluronate and hyaluronate, which is applied in the field of organic chemical synthesis, can solve problems such as peroxide decolorization safety hazards, excessive iron and chromium content in products, and reduced degree of acetyl substitution, etc., to achieve mild reaction and state Good, the effect of reducing consumption

Active Publication Date: 2021-07-16
SHANDONG FOCUSFREDA BIOTECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This process does not require corrosive or pyridine catalysts that are difficult to purify such as concentrated sulfuric acid. However, there are still the following problems: acetyl chloride is highly corrosive, and it is easy to lose equipment during process production, and cause the iron and chromium content of the product to exceed the standard. ; It is necessary to adjust the pH to 12 during post-processing, and the ester group is easily hydrolyzed in an alkaline environment, resulting in a decrease in the degree of acetyl substitution, and the removal of color by peroxide will also bring great safety hazards

Method used

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  • Preparation method of acetylated sodium hyaluronate

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Embodiment 1

[0023] The preparation method of acetylated sodium hyaluronate in this embodiment comprises the following steps:

[0024] (1) Under the protection of nitrogen, weigh 50.00g of HA with a molecular weight of 10KDa in a 1000mL reaction bottle, add anhydrous solvent 250mL toluene, heat up to 60°C and stir until it is completely dissolved and becomes a homogeneous phase, then add molecular sieves to absorb water in the reaction ; After that, cool down the reaction system to -5°C, add 50mL of acetic anhydride dropwise to the reaction solution, then dissolve 0.25g DMAP with 4mL of toluene solution and add dropwise to the reaction solution, react at room temperature for 1 hour, then heat to 40°C for reaction 4h obtained light yellow turbid solution;

[0025] (2) adding an equal volume of water to quench the remaining acetic anhydride, and filtering the reaction solution to remove molecular sieves;

[0026] (3) The reaction solution was purified by membrane filtration, and a small amo...

Embodiment 2

[0033] The preparation method of acetylated sodium hyaluronate in this embodiment comprises the following steps:

[0034] (1) Under nitrogen protection, weigh 30.00g of HA with a molecular weight of 1000KDa in a 1000mL reaction bottle, add anhydrous solvent 300mL toluene and heat up to 70°C and stir (the temperature rise is to dissolve sodium hyaluronate, the larger the molecular weight, the more insoluble ), until the complete solution becomes homogeneous, adding molecular sieves to absorb water in the reaction; then cooling the reaction system to 0°C, adding 90mL acetic anhydride dropwise to the reaction solution, and then dissolving 0.2g DMAP with 4mL toluene and adding dropwise to In the reaction solution, react at room temperature for 1 hour, then heat at 50°C for 12 hours to obtain a light yellow turbid solution;

[0035] (2) adding an equal volume of water to quench the remaining acetic anhydride, and filtering the reaction solution to remove molecular sieves;

[0036]...

Embodiment 3

[0041] The preparation method of acetylated sodium hyaluronate in this embodiment comprises the following steps:

[0042] (1) Under the protection of nitrogen, weigh 20.00g of HA with a molecular weight of 200KDa in a 1000mL reaction bottle, add anhydrous solvent 400mL toluene, heat up to 70°C and stir until it is completely dissolved and becomes a homogeneous phase, then add molecular sieves to absorb water in the reaction ; Afterwards, the temperature of the reaction system was lowered to -5°C, 100mL of acetic anhydride was added dropwise to the reaction solution, and then 0.24g DMAP was dissolved in 4mL of toluene and added dropwise to the reaction solution, reacted at room temperature for 1h, and then heated at 70°C for 48h to obtain Pale yellow turbid solution;

[0043] (2) adding an equal volume of water to quench the remaining acetic anhydride, and filtering the reaction solution to remove molecular sieves;

[0044] (3) The reaction solution was purified by membrane fi...

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Abstract

The invention relates to a preparation method of acetylated sodium hyaluronate, which belongs to the field of organic chemical synthesis, and is characterized by comprising the following steps of: under the protection of inert gas, adding a catalyst into hyaluronate and acetic anhydride in an organic solvent to catalyze a reaction, adding a water absorbent in the reaction process, and carrying out post-treatment, separation, purification and drying on the reaction liquid to obtain the product. According to the method, the condition that the substitution degree is too high or too low can be effectively avoided, so that a product with the acetyl substitution degree of 2.7-3.2 is obtained, reaction raw materials and conditions are mild, and separation and purification steps are simple.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a preparation method of acetylated sodium hyaluronate. Background technique [0002] Acetylated sodium hyaluronate is a moisturizing raw material obtained after sodium hyaluronate undergoes an acetylation reaction. The hydrogen on the hydroxyl group of sodium hyaluronate is replaced by an acetyl group; while maintaining hydrophilicity, its lipophilicity is improved, which helps to improve the affinity and adsorption performance with the skin. With a fresh and non-sticky feel, Sodium Acetylated Hyaluronate provides excellent hydration, repairs the skin barrier, improves skin elasticity and keeps the skin smooth. From the structure of AcHA, four hydroxyl hydrogens on each disaccharide unit can be replaced by acetyl groups, so the degree of substitution ranges from 0 to 4 for a disaccharide structure, and the degree of substitution will affect the hydrophilicity ...

Claims

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Application Information

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IPC IPC(8): C08B37/08
CPCC08B37/0072C08L5/08
Inventor 李庆攀康传利刘磊孙晶晶杜帅汤丽伟张美霞刘蔷廉少杰李取泉李庆
Owner SHANDONG FOCUSFREDA BIOTECH CO LTD
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