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A kind of preparation method of β-carotene

A carotene and vitamin technology, applied in the field of vitamin preparation, can solve problems such as low yield, easily oxidized products, and reduced yield

Active Publication Date: 2021-07-23
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Chinese patents CN101081829A and CN101041631A use hypochlorite to couple to β-carotene under alkaline conditions, but the first two patents are easy to oxidize the product β-carotene due to the strong oxidation of hypochlorite under alkaline conditions. The yield is low; the coupling reaction of the latter patent is a two-phase reaction, the vitamin A triphenylphosphine salt is dissolved in the organic phase, the oxidizing agent and alkali are in the water phase, and the reaction intermediate vitamin A triphenylphosphine ylide Can not be converted into product β-carotene in time, resulting in low yield
This patent can effectively control the solubility of alkali in the organic phase of the reaction, and avoid side reactions such as the self-condensation of VA aldehyde caused by too high alkali concentration and the destruction of the conjugated double bond of the product molecule. Moreover, the post-processing process of this patent is cumbersome, and it takes a long time for isomerization to obtain β-carotene with high purity
[0010] Chinese patent CN108047112A adopts acidic medium oxidant as nitrate, persulfate, peracetic acid, urea peroxide or alkyl hydrogen peroxide to carry out coupling reaction to obtain β-carotene. Has a degradation effect, greatly reducing the yield of the reaction

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Embodiment 1: Preparation of vitamin A triphenylphosphine salt

[0061] Add 49g of vitamin A acetate (2,800,000 IU, 0.147mol) with a purity of 98% to a 1L three-necked flask, 40.5g of triphenylphosphine (0.154mol) and 300g of methanol, and cool to 0°C in an ice-water bath under stirring, and maintain Below 5°C, 15.8g of concentrated sulfuric acid (0.16mol) was slowly added dropwise for about 0.5h, and then continued to keep stirring for 10h, and the reaction solution turned into an orange transparent liquid. Add 150g of deionized water, extract with n-hexane (100g*3 times), the lower layer is the reaction liquid containing vitamin A triphenylphosphine salt (methanol-water solution of VA triphenylphosphine salt), its mass percentage composition 15.8% of vitamin A triphenylphosphine salt, 54.0% of methanol, 27.0% of water, 3.2% of unidentified impurities; the conversion rate of raw material vitamin A acetate is over 99%.

Embodiment 2

[0062] Embodiment 2: Preparation of vitamin A triphenylphosphine salt

[0063] Add 49g of vitamin A acetate (2,800,000 IU, 0.147mol) with a purity of 98% in a 1L three-necked flask, 53.9g of triphenylphosphine (0.20mol) and 400g of ethanol, cool to 0°C in an ice-water bath under stirring, and maintain Below 5°C, 23.0 g of concentrated sulfuric acid (0.23 mol) was slowly added dropwise for about 0.5 h, and then continued to keep stirring for 10 h, and the reaction solution turned into an orange transparent liquid. Add 400g of deionized water, extract with n-hexane (100g*3 times), the lower layer is the reaction liquid containing vitamin A triphenylphosphine salt (ethanol-water solution of VA triphenylphosphine salt), its mass percentage composition 12.2% of vitamin A triphenylphosphine salt, 55.1% of ethanol, 27.6% of water, 5.1% of unidentified impurities; the conversion rate of vitamin A acetate is over 99%.

Embodiment 3

[0064] Embodiment 3: Preparation of vitamin A triphenylphosphine salt

[0065] 110g VA crystallization mother liquor (wherein all-trans VA acetate 42% (0.147mol); 13-cis VA acetate 38%, trans VA alcohol 14%) in 1L there-necked bottle, 46.2g triphenylphosphine (0.17mol) and 400g methanol, cooled to 0°C in an ice-water bath under stirring, and slowly added 21.6g concentrated sulfuric acid (0.22mol) dropwise at a temperature below 5°C for about 0.5h. Orange transparent liquid. Add 250g of deionized water, extract with n-hexane (100g*3 times), the lower layer is the reaction solution containing vitamin A triphenylphosphine salt (methanol-water solution of VA triphenylphosphine salt), its mass percentage composition 10.6% of vitamin A triphenylphosphine salt, 48.4% of methanol, 30.2% of water, and 10.8% of impurities; the conversion rate of all-trans VA acetate in the mother liquor of vitamin A crystallization is above 99%.

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Abstract

The invention provides a preparation method of β-carotene. In the method, an organic phosphine salt obtained by reacting vitamin A derivatives with triphenylphosphine, using cyclodextrin compounds as phase transfer catalysts, and using molecular oxygen as an oxidant in the presence of palladium compound catalysts and weak base compounds, is carried out. After the coupling reaction, β-carotene is obtained. The reaction adopts a series method to prepare β-carotene, the reaction selectivity and yield are high, the process is simple, and the industrial production is convenient.

Description

technical field [0001] The invention belongs to the technical field of vitamin preparation, and relates to a method for preparing beta-carotene, in particular to a method for preparing beta-carotene by coupling reaction. Background technique [0002] β-carotene is a source of vitamin A, which can be used in medicine, food, cosmetics, feed additives, and dyes, and has a good market prospect. [0003] There are many synthesis methods of β-carotene disclosed at present. The techniques for synthesizing β-carotene with vitamin A and its derivatives as starting materials include: [0004] 1. An organic phosphine salt obtained by reacting vitamin A alcohol or its derivatives with a triarylphosphine, and further condensing the organic phosphine salt with vitamin A aldehyde through a Wittig reaction to obtain β-carotene. French patent Er1383944, German patent Gerl148542 and "Pharmaceutical Industry" Volume 16, Volume 2 reported that the yields were 19.11%, 21.36%, and 26.07%, respe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C403/24C07F9/54
CPCC07C403/24C07F9/5442C07C2601/16
Inventor 李莉潘亚男张明峰张涛吕英东刘英瑞程晓波宋军伟
Owner WANHUA CHEM GRP CO LTD