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Method for preparing canthaxanthin by oxidizing beta-carotene

A carotene and canthaxanthin technology is applied in the field of canthaxanthin oxidation by β-carotene, which can solve the problems of inconvenient operation, unfriendly environment, and large discharge of three wastes.

Active Publication Date: 2020-10-27
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Although the above method can prepare canthaxanthin with a medium yield, it needs to use iodine, iodine halide and other iodine-containing compounds with special toxicity and volatility. Harmful, the operating environment must take special protective measures, increasing the investment in equipment and facilities and potential health hazards to employees; at the same time, a large amount of salty wastewater will be generated during the reaction process, the discharge of three wastes is large, and the environment is not friendly; in the industry Special protection measures are required for the operator and the operating environment during production, which is very inconvenient to operate

Method used

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  • Method for preparing canthaxanthin by oxidizing beta-carotene
  • Method for preparing canthaxanthin by oxidizing beta-carotene

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Embodiment 1

[0027] Put 5.36g (10mmol) of β-carotene in a 500ml three-necked flask, add 100ml of acetonitrile, stir at room temperature, add 0.22g (2.0mmol) of catalyst calcium chloride, and then add 70% of oxidant tert-butanol peroxide. Aqueous solution 5.29g (50mmol), heat up to 70 ° C, reflux reaction, reaction pressure normal pressure, reaction time is 6h, after the reaction is completed, add sodium thiosulfate aqueous solution to quench the reaction, wash with water 3 times, separate the organic phase, and spin dry , and then recrystallized with acetone to obtain 4.55 g of purple canthaxanthin with a yield of 81%.

[0028] 1H NMRδ: 6.65(dt, J=20.4Hz, 7.6Hz, 4H), 6.32(ddd, J=36.4Hz, 27.1Hz, 15.8Hz, 10H), 2.47-2.54(m, 4H), 1.96-2.05(m ,12H), 1.81-1.89(m,10H), 1.19(s,12H).

Embodiment 2

[0030] Put 5.36g (10mmol) of β-carotene into a 500ml three-necked flask, add 100ml of acetonitrile, stir at room temperature, add 0.22g (2.0mmol) of catalyst calcium chloride, and then add 5.67g of 30% aqueous solution of oxidant hydrogen peroxide (50mmol), the temperature was raised to 60°C, the reaction pressure was normal pressure, and the reaction time was 6h. After the reaction was completed, an aqueous solution of sodium thiosulfate was added to quench the reaction, washed with water for 3 times, the organic phase was separated, spin-dried, and then recrystallized with acetone , to obtain purple canthaxanthin 4.06g, yield 72%.

Embodiment 3

[0032] Put 5.36g (10mmol) of β-carotene into a 500ml three-necked flask, add 100ml of acetonitrile, stir at room temperature, add 0.40g (2.0mmol) of catalyst calcium bromide, and then add 70% aqueous solution of oxidant tert-butanol peroxide 5.29g (50mmol), heat up to 90°C, reflux reaction, reaction pressure normal pressure, reaction time is 6h, after the reaction is finished, add sodium thiosulfate aqueous solution to quench the reaction, wash with water 3 times, separate the organic phase, spin dry, Then recrystallized with ethanol to obtain 4.23 g of purple canthaxanthin with a yield of 75%.

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Abstract

The invention provides a method for preparing canthaxanthin by oxidizing beta-carotene. The method comprises the following steps of: dissolving beta-carotene in a solvent, and carrying out oxidation reaction in the presence of a catalyst and an oxidant to prepare canthaxanthin; wherein the catalyst is a metal calcium salt compound. The cheap metal calcium salt compound is used as the catalyst, anda peroxide is used as the oxidant to catalyze the oxidation reaction, so that the method has the advantages of mild process route conditions, environment friendliness, simple and convenient operationand easy industrial production.

Description

technical field [0001] The invention relates to a method, in particular to a method for preparing canthaxanthin by oxidation of β-carotene. Background technique [0002] Canthaxanthin is a kind of carotenoid, and natural canthaxanthin exists in crustaceans, fish, algae, eggs, blood, and liver. In 1950, Roche first synthesized canthaxanthin and added canthaxanthin to chicken feed, and found that the presence of canthaxanthin in egg yolk can make the egg yolk produce an orange color that consumers like. In 1984, FDA (US Food and Drug Administration) and WHO (World Health Organization) approved canthaxanthin as a food additive and formulated quality standards. According to pharmacological studies in recent years, it has been found that canthaxanthin has pharmacological effects such as anti-oxidation and improving blood lipid changes. [0003] At present, there are three main methods for preparing canthaxanthin: natural product extraction, microbial fermentation, and chemical ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C403/24
CPCC07C403/24C07C2601/16Y02P20/584
Inventor 沈宏强张涛刘英瑞朱龙龙李莉潘亚男
Owner WANHUA CHEM GRP CO LTD
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