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Preparation method of racemic tocopherol

A technology of tocopherol and trimethylhydroquinone, which is applied in the field of d, can solve the problems of expensive Lewis acid, deterioration, and increased procedures, and achieve the effect of easy-to-obtain raw materials, simple operation, and inhibition of oxidation

Inactive Publication Date: 2011-06-22
YAOPHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Throughout these studies, it is basically possible to obtain tocopherol products with a high yield, but each method still has some unsatisfactory places
For example, the Lewis acid used in the catalytic system used in some methods is relatively expensive, or some special treatments such as loading and inclusion are required for the catalyst, which increases the process; and the characteristics of tocopherol determine that it is very easy to be oxidized and deteriorated. Therefore, how to ensure that the tocopherol is not oxidized in the reaction is also a subject worth studying in the synthesis process.

Method used

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  • Preparation method of racemic tocopherol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1 Preparation of racemic tocopherol

[0021] Add 500 mL of ethyl acetate into a stirring 2L three-necked flask equipped with a condenser, start stirring, add 136 grams (1.0 mol) of zinc chloride, and after stirring evenly, add 152 grams of 2,3,5-trimethylhydroquinone (1.0mol), then slowly add 15mL of concentrated hydrochloric acid dropwise, after the raw material is dissolved, start to drop 300mL (1.1mol) of isophytic alcohol, control the temperature at 40°C, react for 5 hours, add 6.5g (0.1mol) of zinc powder , slowly warming up to 60°C for 2.5 hours. After the reaction, ethyl acetate was recovered under reduced pressure, the concentrate was dissolved in 500 mL of petroleum ether, 500 mL of distilled water was added to stand for liquid separation, and the solvent was recovered after drying to obtain 411 g of crude racemic tocopherol, with a yield of 110%.

Embodiment 2

[0022] Example 2 Preparation of racemic tocopherol

[0023] Add 500 mL of ethyl acetate into a stirring 2L three-necked flask equipped with a condenser, start stirring, add 88 grams (0.67 mol) of aluminum chloride, and add 152 grams of 2,3,5-trimethylhydroquinone after stirring evenly (1.0mol), then slowly add 15mL of concentrated hydrochloric acid dropwise, after the raw materials are dissolved, start to drop 270mL (1.0mol) of isophytic alcohol, control the temperature at 40°C, react for 6 hours, add 5.4g (0.2mol) of aluminum chips , slowly warming up to 60°C for 3 hours. After the reaction, ethyl acetate was recovered under reduced pressure, the concentrate was dissolved in 500 mL of petroleum ether, 500 mL of distilled water was added to stand for liquid separation, and the solvent was recovered after drying to obtain 430 g of crude racemic tocopherol, with a yield of 115%.

Embodiment 3

[0024] Example 3 Preparation of racemic tocopherol

[0025] Add 500 mL of ethyl acetate into a stirring 2L three-necked flask equipped with a condenser, start stirring, add 283 grams (1.5 mol) of tin chloride, and after stirring evenly, add 152 grams of 2,3,5-trimethylhydroquinone (1.0mol), then slowly add 15mL of concentrated hydrochloric acid dropwise, after the raw material is dissolved, start to add 400mL (1.5mol) of isophytol dropwise, control the temperature at 40°C, react for 6 hours, add 6g (0.05mol) of tin powder , slowly warming up to 60°C for 3.5 hours. After the reaction, ethyl acetate was recovered under reduced pressure, the concentrate was dissolved in 500 mL of petroleum ether, 500 mL of distilled water was added to stand for liquid separation, and the solvent was recovered after drying to obtain 400 g of crude racemic tocopherol with a yield of 107%.

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Abstract

The invention discloses a preparation method of racemic tocopherol. In the method, a mixed system consisting of metal hydrochloride MCln and a metal simple substance M serves as a catalytic system for condensation of isophytol and trimethylhydroquinone, wherein M is selected from one of zinc, copper, aluminum, magnesium, tin and titanium atoms; and n represents the quantivalency of a metal atom M, and is an integer selected from 1-4. The method has the advantages of readily available raw materials, easiness in operating, good suppression of oxidation of tocopherol, good application prospect and suitability for industrial production.

Description

technical field [0001] The invention relates to a preparation method of d,l-alpha-tocopherol (racemic tocopherol). Particularly relates to a kind of adopting metal hydrochloride MCl n The mixed system of metal element M is used as the catalytic system for the condensation of isophytol and trimethylhydroquinone, and the method for preparing racemic tocopherol. Background technique [0002] As a very good antioxidant, tocopherol is widely used in medicine, food, cosmetics and other industries. However, natural tocopherol alone is far from being able to meet this huge market demand. Over the past few decades, chemists have made great efforts on how to efficiently prepare racemic tocopherol. Usually, it is prepared by condensation of isophytol and trimethylhydroquinone, the reaction formula is as follows: [0003] [0004] Most of the catalytic systems are selected from Bronsted acid or Lewis acid. For example, CN1108254 discloses that in the presence of scandium trifluo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/72
Inventor 裴东周浩然
Owner YAOPHARMA CO LTD
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