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Method for preparing natural alpha-tocofecol succinic acid monoesters

A technology of succinic acid monoester and tocopherol, which is applied in the field of preparation of natural α-tocopherol succinic acid monoester, and achieves the effects of low production cost, high yield and simple process flow

Inactive Publication Date: 2009-11-18
ZHEJIANG UNIV
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

None of the above patents mentioned triethanolamine as a catalyst

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 36g of natural α-tocopherol with a content of 86.5%, 9.9g of succinic anhydride, 1.8ml of triethanolamine and 75ml of n-hexane were used as starting materials for the reaction. The volume of the reaction kettle was 500ml, the temperature was controlled at 90°C, and the reaction was carried out for 3 hours. After filtering, the filtrate was evaporated to remove the solvent to obtain the natural α-tocopheryl succinic acid monoester product. The purity of the obtained product detected by HPLC is 81.32%, the yield of natural α-tocopherol succinate monoester is 92.12%, and the conversion rate of natural α-tocopherol is 95.28%.

Embodiment 2

[0022] 40 g of natural α-tocopherol with a content of 78.6%, 10.3 g of succinic anhydride, 7.9 ml of triethanolamine and 50 ml of petroleum ether (60-90° C.) were used as starting materials for the reaction. The volume of the reaction kettle was 500ml, the temperature was controlled at 90°C, and the reaction was carried out for 3 hours. After filtering, the filtrate was evaporated to remove the solvent to obtain the natural α-tocopheryl succinic acid monoester product. The purity of the obtained product detected by HPLC is 77.8%, the yield of natural α-tocopheryl succinate monoester is 90.60%, and the conversion rate of natural α-tocopherol is 91.21%.

Embodiment 3

[0024] 40 g of natural α-tocopherol with a content of 98.3%, 20.5 g of succinic anhydride, 2.8 ml of triethanolamine and 80 ml of n-heptane were used as starting materials for the reaction. The volume of the reaction kettle is 500ml, the temperature is controlled at 125°C, and the reaction is carried out for 2 hours. After filtering, the filtrate was evaporated to remove the solvent to obtain the natural α-tocopheryl succinic acid monoester product. The purity of the obtained product detected by HPLC is 96.68%, the yield of natural α-tocopheryl succinate monoester is 92.32%, and the conversion rate of natural α-tocopherol is 95.10%.

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Abstract

The invention discloses a preparation method of natural α-tocopheryl succinic acid monoester. The steps of the method are as follows: taking natural α-tocopherol and succinic anhydride as raw materials, using triethanolamine as a catalyst, placing them in a reaction kettle in turn, adding a solvent; passing nitrogen to replace the air in the autoclave; heating and reacting; filtering, The filtrate is vacuum evaporated to remove the solvent to obtain the natural α-tocopheryl succinic acid monoester product. The preparation method of the natural α-tocopherol succinic acid monoester of the present invention is to synthesize from natural α-tocopherol and succinic anhydride through esterification. The method has the advantages of simple technological process, high yield, low production cost and easy industrialization. The total yield of the whole process reaches over 90%, which is suitable for industrialized production.

Description

technical field [0001] The invention relates to an esterification reaction process, in particular to a preparation method of natural α-tocopheryl succinic acid monoester. Background technique [0002] Natural α-tocopherol (RRR-α-tocopherol) is light yellow viscous transparent liquid, odorless and tasteless. The melting point of (RRR)-α-tocopherol is 2.5-3.5°C. α-tocopherol is soluble in oil, ethanol, chloroform, acetone, but insoluble in water. Tocopherols are strong antioxidants and are themselves easily oxidized. The physiological activity of natural tocopherol is much higher than that of synthetic tocopherol, and the price is also higher, so the use of natural tocopherol is mainly in medicine, food, cosmetics and other aspects related to the human body. (RRR)-α-tocopherol is an intracellular antioxidant that can inhibit the generation of toxic lipid peroxides, stabilize unsaturated acids, and improve the immune response to stimulating coenzyme Q. It has a regulatory e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/72
Inventor 杨亦文苏宝根吴彩娟苏云任其龙
Owner ZHEJIANG UNIV
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