Vitamin A isomerization method

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

Active Publication Date: 2021-09-24
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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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Follow the steps below to carry out the isomerization reaction:

[0057] The dimer content in the VA crude oil A was adjusted to 0.0011%; 100 g of the adjusted VA crude oil was weighed, and 1900 g of dichloromethane was added to prepare a mixed solution. Add 0.0010 g of ruthenium trichloride, and replace the reaction system with nitrogen for 10 min, then stir and react at 20° C. for 10 h. After the reaction, the composition of the reaction solution was analyzed by high performance liquid chromatography, and the results of the isomerization reaction are listed in Table 1.

Embodiment 2

[0059] Follow the steps below to carry out the isomerization reaction:

[0060] The dimer content in VA crude oil B was adjusted to 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. Add 0.0043g of rhodium acetate, replace the reaction system with nitrogen for 10 minutes, and then stir and react at 40°C for 4 hours. After the reaction, analyze the composition of the reaction solution by high performance liquid chromatography.

Embodiment 3

[0062] Follow the steps below to carry out the isomerization reaction:

[0063] Adjust the dimer content in VA crude oil C to 0.0112%; weigh 90g of the adjusted VA crude oil, add 210g of acetonitrile to prepare a mixed solution; then add 0.4099g of potassium tetrachloropalladate, and replace the reaction system with nitrogen for 10 minutes , stirred and reacted at 50° C. for 3 h. 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 vitamin A isomerization method. The method comprises the steps of (1) controlling the content of vitamin dimers in VA crude oil containing 11-cis-vitamin A and 9-cis-vitamin A to be 0.001-0.02%; and 2) carrying out an isomerization reaction on the VA crude oil obtained in the step 1) under the action of a homogeneous metal catalyst to generate the all-trans vitamin A. According to the method, 11-cis-vitamin A and 9-cis-vitamin A in the VA crude oil can be isomerized into all-trans vitamin A efficiently at the same time, and the conversion rate of the total cis-vitamin A is high.

Description

technical field [0001] The invention relates to an isomerization method, in particular to a vitamin A isomerization method. Background technique [0002] Vitamin A has different synthesis 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, isomerizing 11-cis vitamin A and 9-cis vitamin A into all-trans vitamin A can greatly increase the yield of all-trans vitamin A and reduce production costs , which is of great significance to industrial production. [0003] Conventional isomerization methods mainly include thermal isomerization, photoisomerization and chemical isomerization. Thermal isomerization generally needs to be achieved at a h...

Claims

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Application Information

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Patent Type & Authority Applications(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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