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Method for preparing canthaxanthin by beta-carotene

A technology of carotene and canthaxanthin, which is applied in the field of synthesis of canthaxanthin by one-step oxidation method, can solve hidden dangers and safety problems, and achieve the effects of low dosage, high reaction yield and safe process operation

Active Publication Date: 2019-02-22
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reaction yield of this method is up to 78%. The disadvantage is that hydrogen peroxide is an explosive chemical, and there are potential safety hazards when using it.

Method used

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  • Method for preparing canthaxanthin by beta-carotene

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Experimental program
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Effect test

Embodiment 1

[0038] In the autoclave of 1L, add 16.08g (0.03mol) β-carotene successively, 800g dichloroethane, 4mg (0.1%, mol ratio is relative to β-carotene) copper chloride, 2.2mg (0.1%, mol Relative to β-carotene) glycine, 68mg (0.2%, molar ratio relative to β-carotene) β-cyclodextrin, filled with air and pressurized to an absolute pressure of 2Mpa, heated to 60°C to react, reacted for 15h, and the reaction solution Take a small amount for high-performance liquid chromatography analysis, the reaction conversion rate is 95.6%, and the selectivity is 93.6%. Stop the reaction, filter the reaction solution to remove the catalyst, then heat the filtrate to reflux, add 800 g of ethanol to the system, cool to -10°C and filter with suction to obtain 13.2 g of canthaxanthin solids, with a yield of 82.1%.

Embodiment 2

[0040] Add 16.08g (0.03mol) beta-carotene successively in the autoclave of 1L, 640g dichloroethane, 0.05% (molar ratio is relative to beta-carotene) copper acetate, 0.2% (molar ratio is relative to beta-carotene) element) glycine, 0.2% (molar ratio relative to β-carotene) β-cyclodextrin is filled with air and pressurized to an absolute pressure of 2Mpa, heated to 50°C for reaction, and reacted for 15 hours. Take a small amount of the reaction solution for high-performance liquid chromatography analysis , the reaction conversion rate is 92.6%, and the selectivity is 96.6%. Stop the reaction, filter the reaction solution to remove the catalyst, then heat the filtrate to reflux, add 600 g of ethanol to the system, cool to -20°C and filter with suction, the yield of canthaxanthin is 81.6%.

Embodiment 3

[0042] In the autoclave of 1L, add 16.08g (0.03mol) β-carotene successively, 640g dichloroethane, 0.05% (molar ratio is relative to β-carotene) copper trifluoroacetate, 0.2% (molar ratio is relative to β-carotene) -carotene) serine, 0.2% (molar ratio relative to β-carotene) α-cyclodextrin is filled with air and pressurized to an absolute pressure of 1.5Mpa, heated to 70°C for reaction, and reacted for 12 hours. Take a small amount of the reaction solution for high-efficiency liquid According to phase chromatography analysis, the reaction conversion rate is 91.6%, and the selectivity is 95.6%. Stop the reaction, filter the reaction solution to remove the catalyst, then heat the filtrate to reflux, add 800 g of ethanol to the system, cool to 0° C. and suction filter, the yield of canthaxanthin is 79.2%.

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Abstract

The invention discloses a novel synthesis method for preparing canthaxanthin by beta-carotene one-step oxidization. According to the method, beta-carotene serves as an initial raw material, a cyclodextrin compound serves as a phase transfer catalyst, molecular oxygen serves as an oxidizing agent under catalysis of a copper compound and amino acid, and the canthaxanthin is prepared by one-step oxidization. The route is high in reaction selectivity and simple in process and facilitates industrial production.

Description

technical field [0001] The invention relates to a synthesis method for preparing canthaxanthin by a one-step oxidation method, in particular to a method for preparing canthaxanthin from β-carotene. Background technique [0002] Canthaxanthin is also known as canthaxanthin, canthaxanthin, β-carotene-4,4'-dione, and jialisu red. Its structure is similar to β-carotene, but the difference is the cyclohexene ring of canthaxanthin has a carbonyl group. Canthaxanthin was approved by FDA / WHO as a food additive in 1984. The activity of canthaxanthin to quench active oxygen and the ability to scavenge free radicals are twice that of β-carotene and fifty times that of vitamin E. It is widely used in aquaculture, feed additives, food colorants and pharmaceutical industries. [0003] In 1980, Joachim Paust (US4212827) and others reported a method for preparing canthaxanthin by oxidizing β-carotene. The method is to oxidize β-carotene with chlorate or bromate in the presence of a catal...

Claims

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Application Information

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IPC IPC(8): C07C403/24
CPCC07C403/24C07C2601/16
Inventor 刘英瑞宋明焱孙犀璨张涛吕英东郭劲资朱龙龙林龙李莉宋军伟黎源
Owner WANHUA CHEM GRP CO LTD
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