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Method for synthesizing tocopherol succinate

A technology of tocopherol succinate and tocopherol, applied in organic chemistry and other directions, can solve problems such as low solubility, difficult application, solvent toxicity, etc., and achieve the effects of mild reaction conditions, high conversion rate, and less enzyme inactivation

Inactive Publication Date: 2015-05-06
ZHEJIANG NHU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The natural vitamin E succinate used as a raw material for medicines and health care products must meet 96-102% of the national regulations, so the application range of the product is correspondingly narrow
[0010] 2. The yield of the product is not high
The yield of natural vitamin E succinate is only between 60-80% based on the molecular weight of raw material natural vitamin E (d-a-tocopherol), the consumption of raw and auxiliary materials is high, and the manufacturing cost of the product is correspondingly increased, so it is not suitable for industrial production technology
[0011] 3. The process conditions of some technical requirements are too harsh, and the reaction time is too long, so it is difficult to apply in industrial production
[0012] 4. Since the purity of the product after esterification is not high, it needs to be further purified by solvent recrystallization method, the process is long and the consumption is high
Due to the relatively low solubility of the raw material polyethylene glycol and the reaction product TPGS in organic solvents, which affects the mass transfer and reaction rate, the subsequent separation process is also relatively complicated, and the solvent has certain toxicity. When TPGS is used as a food and drug additive, it may affect the adverse effect on its safety

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Measure 300 grams of natural vitamin E with a content of 96.4% and 95 grams of succinic anhydride, dissolve it in 1.2 liters of isopropyl ether and 60 ml of ethanol, add 10 grams of lipase, stir and react at 50°C for 5.5 hours, use one side to react , while using the azeotropic method to remove the water generated by the reaction system, react for 24-48 hours, cool to room temperature, after the reaction, wash with dilute hydrochloric acid and pure water to neutrality; let the layers stand, and directly pour out the upper organic layer , remove the lower water phase, lipase can be directly applied to the next batch of reactions, remove the solvent under vacuum, add n-hexane to crystallize, dry and pulverize to obtain 343.8 grams of high-purity natural vitamin E succinic acid monoester with a content of 98.7 Natural vitamin E succinic acid monoester, the yield is 95.2%.

Embodiment 2

[0023] Measure 400 grams of 97% natural vitamin E and 130 grams of succinic anhydride, dissolve in 1.2 liters of isopropyl ether and 60 ml of isopropanol, add 15 grams of lipase, stir and react at 60 ° C for 6.5 hours, use While reacting, use the azeotropic method to remove the water generated in the reaction system, react for 24-48 hours, cool to room temperature, after the reaction is completed, wash with dilute hydrochloric acid and pure water until neutral; let the layers stand, and pour out the upper layer directly The organic layer is separated from the lower water phase, and the lipase can be directly applied to the next batch of reactions. The solvent is removed under vacuum, and n-hexane is added to crystallize, dried and crushed to obtain 423.8 grams of high-purity natural vitamin E succinic acid monoester. 98.7% natural vitamin E monosuccinate, yield 96.2%. Please refer to the solvent handbook for specific azeotropic water data.

Embodiment 3

[0025] Measure 400 grams of natural vitamin E and 120 grams of succinic anhydride with a content of 94.5%, dissolve them in 1.2 liters of n-hexane and 60mlDMSO, and in isopropanol, add 6 grams of dimethylaminopyridine, 10 grams of zinc powder, Stir and react at ℃ for 6.5 hours, use the method of removing the water generated in the reaction system by azeotropic method while reacting, react for 24-48 hours, cool to room temperature, after the reaction is completed, wash with dilute hydrochloric acid and pure water until neutral; Stratify, pour out the upper organic layer directly, and separate the lower aqueous phase. The lipase can be directly applied to the next batch of reactions. The solvent is removed in a vacuum state, and n-hexane is added to crystallize, dried and crushed to obtain high-purity natural vitamin E. 443.5 grams of natural vitamin E succinic acid monoester with a content of 98.7 grams, yield 95.2%, please refer to the solvent manual for specific azeotropic wat...

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Abstract

The invention discloses a method for synthesizing tocopherol succinate. The method comprises the following steps: by taking tocopherol and succinic acid as raw materials and taking lipase as a catalyst, adding the tocopherol and succinic acid in a mole ratio of (1: 1) to (1: 5) into a double-solvent reaction mixed solvent which is prepared by mixing a halohydrocarbon or alkane solvent and DMSO; reacting at 20-60 DEG C for 24-48h by using a method of generating water through an azeotropic removal reaction system while reacting; cooling to room temperature; washing to be neutral by diluted hydrochloric acid and pure water after the reaction is finished; standing for layering to separate out the lower water phase; removing the solvent of the oil phase under vacuum state; adding normal hexane to crystallize; and drying and grinding to obtain high-purity natural vitamin E monoester succinate.

Description

technical field [0001] The invention relates to a method for synthesizing tocopherol succinate. Background technique [0002] Vitamin E has significant functions of anti-aging, anti-tumor, preventing cardiovascular and cerebrovascular diseases, and improving immunity of the body. It is an indispensable vitamin in human life activities. Vitamin E contains phenolic hydroxyl groups in its structure, so it is easily oxidized. At the same time, because it is a fat-soluble vitamin, it has brought certain restrictions on the application in some occasions. [0003] Existing related patents also use enzyme-catalyzed esterification reaction, using tocopherol and succinic acid as raw materials. Other literatures on the synthesis of tocopherol succinate include the use of tocopherol and acid anhydride as raw materials, which require neutralization and washing, resulting in a large amount of waste water and environmental problems. [0004] In recent years, researchers from all over the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/72
CPCC07D311/72
Inventor 曾庆宇吕国锋黄国东张剑平谭立明陈蕴刘祥洪
Owner ZHEJIANG NHU PHARMA
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