Improved synthesizing technique for beta-carotene

A carotene and synthesis process technology, applied in the direction of organic chemistry and the like, can solve the problems of reducing the purity of beta-carotene, unsafe industrial production, expensive hydrogen peroxide, etc., and achieves improved reaction safety, simplified post-processing process, and production cost. low effect

Active Publication Date: 2007-09-26
ZHEJIANG MEDICINE CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are following disadvantages in this reaction: the hydrogen peroxide price is more expensive, and the production cost is high; the concentration of hydrogen peroxide is 30%, and it is easy to decompose during the reaction to cause dangerous consequences such as explosion, and industrial production is very unsafe; organic solvent), in the post-reaction treatment process, triphenoxyphosphine is precipitated together with the crude product of β-carotene during filtration, and needs to be recrystallized or rinsed to remove triphenoxyphosphine in the crude product of β-carotene, which will reduce the β-carotene - the purity of carotene

Method used

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  • Improved synthesizing technique for beta-carotene

Examples

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Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: Preparation of vitamin A triphenylphosphine salt

[0019] Put 50 grams of vitamin A acetate (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 keep Below 15°C, 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 liquid turned into an orange transparent liquid. Add 80 g of deionized water, extract twice with 100 ml of n-hexane each time, and the lower layer is methanol-water solution of VA triphenylphosphine salt.

Embodiment 2

[0020] Embodiment 2: Coupling reaction prepares β-carotene

[0021] Put the methanol-water solution of the VA triphenylphosphine salt obtained in Example 1 in a 1000 ml four-neck bottle, cool it to 0° C. in an ice-salt bath, and add dropwise 150 grams of sodium hypochlorite aqueous solution containing 10% available chlorine under 5° C. At the same time, saturated aqueous sodium carbonate solution was added dropwise to ensure that the pH value was between 8-10 after the reaction was completed, and the addition was completed in about 1 hour, and the insulation continued to stir for 1 hour.

[0022] After filtration, 58 grams of red fine powdery crude product β-carotene was obtained, which weighed 50.2 grams after vacuum drying, and the content was detected as 65% by ultraviolet-visible spectrophotometer. The crude product was refluxed in n-heptane for 12 hours under the protection of nitrogen, then cooled, filtered, and dried to obtain 30 g of dark red crystals with a content of...

Embodiment 3

[0023] Embodiment 3: prepare β-carotene with VA crystallization mother liquor

[0024] 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 The vitamin A acetate in, other conditions are the same, the methanol-water solution of VA triphenylphosphine salt is obtained. The coupling reaction was carried out according to the conditions in Example 2 to obtain 28.9 grams of β-carotene fine product with a content of 96.7%, and the total yield was 36.7%.

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Abstract

The invention discloses a making method of beta-carotene through coupling reaction, which is characterized by the following: adopting 30% hydrogen dioxide solution to couple two molecular organic phosphors; saving cost effectively; reacting vitamin A derivant and triphenylphosphine to produce organic phosphine salt; coupling under hypochlorite to obtain the product with water and water dissolution as organic solvent; avoiding explosive accident; improving reacting safety effectively.

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....

Claims

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Application Information

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IPC IPC(8): C07C403/24
Inventor 马文鑫沈润溥徐国兴沈华良胡四平
Owner ZHEJIANG MEDICINE CO LTD
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