Synthetic method for beta-carotene

A technology of carotene and synthesis method, applied in the field of synthesis of beta-carotene, can solve problems such as slow reaction rate and low product yield, and achieve the effects of easy handling, simple operation and improved catalytic oxidation effect

Active Publication Date: 2018-11-16
XIAMEN KINGDOMWAY GROUP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Oxygen is a recognized green oxidant, and the reaction product is water, which has the advantages of being economical, practical and environmentally friendly. The prior art has reported the application of oxygen in the oxidative coupling reaction of

Method used

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  • Synthetic method for beta-carotene
  • Synthetic method for beta-carotene
  • Synthetic method for beta-carotene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1: Coupling reaction prepares β-carotene

[0038] Take 90g of vitamin A acetate oil (2.213 million IU / g, 0.208mol) and 48.4g of aniline (0.52mol) and dissolve it in 1100ml of ethanol to prepare a vitamin A acetate-ethanol solution. Add 218.2g triphenylphosphine (0.832mol) and 2300ml ethanol respectively in the three-necked flask, cool down to below 10°C, slowly drop 31.0g concentrated sulfuric acid (0.316mol) into the dropping funnel, and control the dropping temperature below 10°C, After the dropwise addition, stirring was continued for 2h. Add vitamin A acetate-ethanol solution and react at 25°C for 24 hours to obtain vitamin A triphenylphosphine chloride solution. Then concentrate under reduced pressure, then add 200ml of acetone to dissolve, put it in the refrigerator for 24h to crystallize, filter, wash and dry the crystals to obtain vitamin A triphenylphosphine sulfate (the same below).

[0039] Vitamin A triphenylphosphine sulfate (1.0mmol), VO(acac)...

Embodiment 2

[0041] Take 90g of vitamin A acetate oil (2.213 million IU / g, 0.208mol) and 48.4g of aniline (0.52mol) and dissolve it in 1100ml of ethanol to form a vitamin A acetate-ethanol solution. Add 218.2g triphenylphosphine (0.832mol) and 2300ml ethanol respectively in the three-necked flask, cool down to 10°C, slowly add 51.5ml concentrated hydrochloric acid (mass concentration 37.5%, 0.624mol) dropwise through the dropping funnel, and control the dropping temperature to 10°C, after the dropwise addition, continue to stir for 2h. Add vitamin A acetate-ethanol solution and react at 25°C for 24 hours to obtain vitamin A triphenylphosphine chloride solution. Then concentrate under reduced pressure, then add 200ml of acetone to dissolve, put it in the refrigerator for 24h to crystallize, filter the crystals, wash, and dry to obtain vitamin A triphenylphosphine hydrobromide (the same below).

[0042] Vitamin A triphenylphosphine hydrochloride (1.0mmol), VO(OAc) 2 (0.1mmol), 4A molecular...

Embodiment 3

[0044] Take 90.96g vitamin A alcohol (2.9497 million IU / g, 0.281mol) and 15.4ml pyridine (0.191mol) and dissolve it in 500ml methanol to make vitamin A alcohol-methanol solution. Add 77.4g (0.295mol) of triphenylphosphine and 1000ml methanol respectively in the three-necked flask, cool down to 0°C, slowly add 45.4ml HBr (mass concentration is 47%, 0.393mol) dropwise through the dropping funnel, and control the dropping temperature to 0°C, continue to stir for 2h after the dropwise addition, add vitamin A alcohol-methanol solution, and react at 10°C for 24h. Then concentrate under reduced pressure, then add 200ml of acetone to dissolve, put it in the refrigerator for 24h to crystallize, filter the crystals, wash, and dry to obtain vitamin A triphenylphosphine hydrobromide (the same below).

[0045] Vitamin A triphenylphosphine hydrobromide (1.0mmol), NH 4 VO 3 (0.1mmol), 4A molecular sieve (0.3g), 12-crown-4 (2.0mmol) and KOH (2.0mmol) were added in tetrahydrofuran (20ml), an...

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Abstract

The invention provides a synthetic method for beta-carotene. The synthetic method comprises the following steps: preparing an organic phosphine salt from retinol or a derivative thereof; and subjecting the organic phosphine salt to an intermolecular oxidative coupling reaction in an oxygen atmosphere in the presence of a vanadium compound catalyst and a molecular sieve so as to obtain beta-carotene. According to the invention, clean, environment-friendly, economic, easily-available, convenient, safe and oxygen-containing gas is used as an oxidizing agent, so no harm is posed to environment, cost is low, and industrial production is facilitated; a vanadium compound is used as a catalyst, so time for the coupling reaction is greatly reduced; the molecular sieve is used as a cocatalyst, so the usage amount of the catalyst is lowered, catalytic oxidation effect is improved, and discharge of waste water containing metal ions is reduced; the addition of a polyether phase-transfer catalyst can initiate a reaction of substrates in a heterogeneous-phase reaction system; and a solid alkaline compound forms a complex with the polyether phase-transfer catalyst, and is thus dissolved in an organic phase and participates in the reaction, so the solubility of alkali in the organic phase is effectively controlled, the reaction is promoted, production of by-products is inhibited at the same time, the yield of the target product is increased, and thus, the purpose of improving yield is achieved.

Description

technical field [0001] The present invention relates to beta-carotene, in particular to a synthesis method of beta-carotene. 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 domestic research reports on the synthesis of β-carotene. According to different reaction routes, the synthesis routes of β-carotene can be divided into C19+C2+C19, C15+C10+C15 and C20+C20 condensation reactions. Among them, the organic phosphonium salt obtained by the reaction of vitamin A alcohol or its derivatives with triphenylphosphine is an important intermediate of β-carotene, which can further undergo C20+C20Wittig condensation reaction to prepare β-carotene, and can also be used in the presence of oxidants In the presence of self-intermolecular oxidative coupling reaction to prepare β-carotene; [0004] Wittig condensation reaction route: the organ...

Claims

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Application Information

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IPC IPC(8): C07C403/24
CPCC07C403/24C07C2601/16C07F9/5442
Inventor 许素霞刘华英陈芳芳
Owner XIAMEN KINGDOMWAY GROUP
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