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A kind of method of vitamin A isomerization

A vitamin and isomerization technology, applied in the field of isomerization, can solve the problems of conversion, increased content of 9-cis vitamin A, inability to isomerize vitamin A, etc.

Active Publication Date: 2022-08-05
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Photoisomerization usually requires the addition of a photosensitizer to achieve a good isomerization effect, but photosensitizers are generally highly toxic and even carcinogenic, which affects the quality of the final product. At the same time, due to the particularity of the photoisomerization reaction device, industrialization is not conducive to the realization of
[0004] Chemical isomerization is a common way of isomerization of vitamin A. It is reported in the patent US5908957A that NO or NO, N 2 The mixture is used as a catalyst to isomerize vitamin A. This method is mainly suitable for isomerizing 11-cis vitamin A to all-trans vitamin A, but it is known in the field that the isomerization of 9-cis vitamin A is difficult, so it is implemented As can be seen from the example data, all examples cannot contain 9-cis vitamin A isomerization
[0005] It is reported in the patent US4051174A that 9-cis vitamin A can be converted to all-trans vitamin A by using a palladium-containing compound as a catalyst, but the conversion rate of 9-cis vitamin A is low, and this conversion process can only be carried out in raw materials containing only In the case of 9-cis vitamin A and all-trans vitamin A, when the raw material contains other cis isomers (such as 11-cis vitamin A), 9-cis vitamin A cannot contribute to the all-trans vitamin A conversion, and the conversion of other cis isomers will lead to an increase in the content of 9-cis vitamin A

Method used

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  • A kind of method of vitamin A isomerization
  • A kind of method of vitamin A isomerization

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] The isomerization reaction is carried out according to the following steps:

[0057] The dimer content in the VA crude oil A was adjusted to be 0.0011%; 100 g of the adjusted VA crude oil was weighed, and 1900 g of dichloromethane was added to prepare a mixed solution. Then, 0.0010 g of ruthenium trichloride was added, and the reaction system was replaced with nitrogen for 10 minutes, and the reaction was stirred at 20° C. for 10 hours. After the reaction, the composition of the reaction solution was analyzed by high performance liquid chromatography, and the isomerization reaction results were listed in Table 1.

Embodiment 2

[0059] The isomerization reaction is carried out according to the following steps:

[0060] The dimer content in the VA crude oil B was adjusted to be 0.0015%; 110 g of the adjusted VA crude oil was weighed, and 165 g of n-hexane was added to prepare a mixed solution. Then 0.0043g of rhodium acetate was added, the reaction system was replaced by nitrogen for 10 minutes, and the reaction was stirred at 40 ° C for 4 hours. After the reaction, the composition of the reaction solution was analyzed by high performance liquid chromatography. The results of the isomerization reaction are listed in Table 1.

Embodiment 3

[0062] The isomerization reaction is carried out according to the following steps:

[0063] The dimer content in the VA crude oil C was adjusted to be 0.0112%; 90 g of the adjusted VA crude oil was weighed, and 210 g of acetonitrile was added to prepare a mixed solution; 0.4099 g of potassium tetrachloropalladate was added, and the reaction system was replaced by nitrogen for 10 min , the reaction was stirred at 50° C. for 3 hours. After the reaction, the composition of the reaction solution was analyzed by high performance liquid chromatography. The results of the isomerization reaction are listed in Table 1.

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Abstract

The invention discloses a method for isomerization of vitamin A, which comprises the following steps: 1) controlling the content of vitamin dimer in VA crude oil containing 11-cis vitamin A and 9-cis vitamin A to be 0.001-0.02 %; 2) The VA crude oil obtained in step 1) undergoes isomerization reaction under the action of a homogeneous metal catalyst to generate all-trans vitamin A. The invention can simultaneously and efficiently isomerize 11-cis vitamin A and 9-cis vitamin A in the VA crude oil into all-trans vitamin A, and the conversion rate of total cis vitamin A is high.

Description

technical field [0001] The present invention relates to a kind of isomerization method, in particular to a kind of vitamin A isomerization method. Background technique [0002] Vitamin A has different synthetic routes, the most representative of which are the C6+C14 route of Roche and the C5+C15 route of BASF. The composition of vitamin A isomers synthesized by different routes is quite different. The main geometric configurations of vitamin A synthesized by BASF route are all-trans vitamin A, 11-cis vitamin A and 9-cis vitamin A. Among them, all-trans vitamin A has the highest biological activity. The isomerization of 11-cis vitamin A and 9-cis vitamin A into all-trans vitamin A can greatly improve the yield of all-trans vitamin A and reduce production costs. , is of great significance to industrial production. [0003] Conventional isomerization methods mainly include thermal isomerization, photoisomerization and chemical isomerization. Thermal isomerization generally n...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C403/08
CPCC07C403/08C07C2601/16C07B2200/09
Inventor 张旭翟文超张涛
Owner WANHUA CHEM GRP CO LTD
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