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Synthesizing technique for beta-carotene

A carotene and synthesis process technology, applied in the direction of organic chemistry, etc., can solve the problems of easy oxidative damage to beta-carotene, difficult to control the feeding ratio, large production fluctuation, etc., to reduce the probability of oxidative damage, and easy to feed the ratio Control, the effect of small production fluctuations

Active Publication Date: 2007-12-05
浙江可明生物医药有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This reaction has the following disadvantages: the used hydrogen peroxide (or other oxidizing agent) during the coupling reaction has strong oxidizing properties, and the product β-carotene that is easily oxidized and destroyed is generated. If alcohols and other solvent systems that are easily miscible with water are used, Then the product is more likely to be oxidized, which will cause problems such as low product yield, large production fluctuations, and difficult control of the feeding ratio.

Method used

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  • Synthesizing technique for beta-carotene
  • Synthesizing technique for beta-carotene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1: Preparation of vitamin A triphenylphosphine salt

[0021] Put 50 grams of vitamin A (VA, light yellow crystals, 2.8 million IU, 0.147 moles), 39 grams of triphenylphosphine (0.149 moles) and 500 milliliters of methanol in a 1000 milliliter three-necked bottle, cool to 10 ° C in an ice-water bath under stirring, and maintain for 15 Below ℃, 15 grams of concentrated sulfuric acid was slowly added dropwise, and the addition was completed in about 1 hour, and then continued to keep warm and stirred for 12 hours, and the reaction solution turned into an orange transparent solution. Add 80 grams of deionized water, extract twice with 100 milliliters of n-hexane each time, the lower layer is the methanol-water solution of VA triphenylphosphine salt, and recover the solvent methanol under reduced pressure below 30 ° C until solids are precipitated (at this time, the mixed system Weighing 130 grams), then 600 grams of water was added to dissolve the solid into a cl...

Embodiment 2

[0022] Embodiment 2: Coupling reaction prepares β-carotene

[0023] Put the aqueous solution of VA triphenylphosphine salt obtained in Example 1 in a 2000 ml four-necked bottle, add 600 ml of chloroform, cool to 0°C in an ice-salt bath, and add dropwise sodium hypochlorite containing 10% available chlorine under 5°C 150 grams of aqueous solution, while also adding saturated aqueous sodium carbonate dropwise to ensure that the pH value is between 8-10 after the reaction is completed, the addition is completed in about 1 hour, and the insulation is continued to stir for 1 hour.

[0024] Separate the layers to obtain a red organic layer, wash it with 200 ml of water, recover the solvent below 55°C, and obtain a red fine powder, add 200 ml of methanol, reflux for 10 minutes, filter to obtain 68 g of crude product β-carotene, and weigh it after vacuum drying. 61.2 grams, the content detection is 68%. The crude product was refluxed in n-heptane for 12 hours under the protection of ...

Embodiment 3

[0025] Embodiment 3: prepare β-carotene with VA crystallization mother liquor

[0026] Be the VA crystallization mother liquor of 1.3 million IU with 110 gram content (liquid chromatography analysis: all-trans VA acetate 42%; 13-cis VA acetate 40%, trans VA alcohol 13%) replace embodiment 1 VA crystal in the same other conditions, the aqueous solution of VA triphenylphosphine salt was obtained.

[0027] Put the aqueous solution of VA triphenylphosphine salt in a 2000 ml four-necked bottle, add 600 ml of chloroform, cool in an ice-salt bath to 0°C, keep it below 5°C, add 30 grams of 30% hydrogen peroxide, and then keep it below 10°C Add saturated sodium carbonate aqueous solution dropwise until the pH value of the system is greater than 9, the addition is completed in about 1 hour, and the temperature is kept and the stirring is continued for 1 hour.

[0028] Separate the layers to obtain a red organic layer, wash it with 200 ml of water, recover the solvent below 55 ° C, and ...

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Abstract

The present invention discloses new coupling reaction process for preparing beta-carotene. Organic phosphine salt is first prepared through reacting vitamin A derivative and triphenyl phosphine, and then made to produce coupling reaction in the presence of oxidant to obtain beta-carotene. The present invention features that the coupling reaction is completed in a two phase system of water phase and water insoluble organic solvent phase, so that the produced beta-carotene is extracted constantly by the organic solvent phase, decreasing the possibility of oxidizing produced beta-carotene and raising beta-carotene yield.

Description

technical field [0001] The invention relates to the preparation of vitamins, in particular to a method for obtaining beta-carotene by coupling reaction. Background technique [0002] β-carotene is an important drug in the vitamin A class, and its market prospect is very good. The organic phosphonium salt obtained by the reaction of vitamin A alcohol or its derivatives with triphenylphosphine is an important intermediate for the preparation of β-carotene, which can be further prepared by Wittig condensation reaction with vitamin A aldehyde to prepare β-carotene (Joachim Buddrus , et al., USP.3,634,518, Process for Preparing Alkylidene Phosphoranes, [P] 1972; Badische Anlin & Soda-Fabrik Aktiengesellschaft, DE 974,890, Production of Compounds of the Axerophthylidene Series, [P] 1964). It is also possible to carry out the condensation reaction between two molecules of organic phosphonium salts to prepare β-carotene (Bernhard Schulz, et al., USP.4,105,855, Manufacture of Symmet...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C403/24
Inventor 胡四平马文鑫梁智平陈春峰
Owner 浙江可明生物医药有限公司
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