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Technique for synthesizing vitamin A aldehyde

A synthesis process and vitamin technology, applied in the field of vitamin A aldehyde synthesis process, can solve the problems of catalyst deactivation or decomposition and damage, affecting the effect of the catalytic system, etc., and achieve the effects of fast reaction speed, stable catalyst and high catalytic activity.

Inactive Publication Date: 2008-04-30
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Among the above-mentioned catalysts of A, B, and C, the catalytic performance of C is better, but because its 4-position hydroxyl group is easily oxidized and destroyed in the oxidation reaction system, the catalyst is deactivated or decomposed, which affects the catalytic system. Effect

Method used

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  • Technique for synthesizing vitamin A aldehyde
  • Technique for synthesizing vitamin A aldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] First prepare 4-methoxy-1-oxo-2,2,6,6-tetramethylpiperidine, in 1000ml there is a three-necked flask with stirring, dropping funnel and condenser, add 87g (0.5mol) 4-hydroxyl-1-oxo-2,2,6,6-tetramethylpiperidine, add 600ml THF, add 20g of NaH (60% content, 0.5mol) while stirring under the protection of nitrogen, there is a large amount of After stirring for 1h, add 38mL (0.6mol) of MeI dissolved in 100mL THF dropwise at 0°C. After 1h, the solution is orange-red and solids are formed. The mixture is reacted at room temperature for 5h , after removal, add 1500ml of ether, wash with ×100ml of water, separate the ether, and use anhydrous MgSO 4 After drying, diethyl ether was distilled off under normal pressure to obtain a viscous red liquid, which was added to 200 mL of n-hexane and stored at -20°C. 136 g (yield: 72.5%) of needle-like crimson crystals crystallized out, melting point: 42-43°C.

[0021] Then synthesize vitamin A aldehyde, first put 100 grams of vitamin A alc...

Embodiment 2

[0023] First prepare 4-ethoxy-1-oxo-2,2,6,6-tetramethylpiperidine, in a 250ml there-necked flask with stirring, dropping funnel and condenser, add 17.4g (0.1mol ) of 4-hydroxy-1-oxo-2,2,6,6-tetramethylpiperidine, add 100ml THF, add 4.0g (0.1mol) of NaH while stirring under the protection of nitrogen, there are a lot of bubbles After stirring for 1 h, C dissolved in 30 mL THF was added dropwise 2 h 5 I 9.2mL (0.13mol), drop by drop at 0°C, drop after 1h, the solution is orange red, and a solid is formed, the mixture is reacted at room temperature for 5h, add 400ml of ether, wash with 2×50ml of water, separate Ether layer, with anhydrous MgSO 4 After drying, diethyl ether was distilled off under normal pressure to obtain a viscous red liquid, which was added to 40 mL of n-hexane and stored at -20°C, and 25 g of needle-like crimson crystals crystallized out, melting point: 35-36°C.

[0024] Then synthesize vitamin A aldehyde, first put 100 grams of vitamin A alcohol (yellow cr...

Embodiment 3

[0026] First prepare 4-methoxy-1-oxo-2,2,6,6-tetramethylpiperidine, in 1000ml there is a three-necked flask with stirring, dropping funnel and condenser, add 87g (0.5mol) 4-hydroxyl-1-oxo-2,2,6,6-tetramethylpiperidine, add 600ml THF, add 20g of NaH (60% content, 0.5mol) while stirring under the protection of nitrogen, there is a large amount of After stirring for 1 h, 38 mL of MeI (0.6 mol) dissolved in 100 mL of THF was added dropwise at 0°C. After 1 h, the solution was orange-red and a solid was formed. The mixture was reacted at room temperature for 5 h. After removal, add 1500ml of ether, wash with ×100ml of water, separate the ether, and wash with anhydrous MgSO 4 After drying, diethyl ether was distilled off under normal pressure to obtain a viscous red liquid, which was added to 200 mL of n-hexane and stored at -20°C. 136 g (yield: 72.5%) of needle-like crimson crystals crystallized out, melting point: 42-43°C.

[0027] Then synthesize vitamin A aldehyde, first put 100...

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Abstract

The invention discloses a vitamin A aldehyde synthesis process. The invention has the process steps that vitamin A alcohol is taken as the raw material, which is performed with oxidation reaction under a certain reaction temperature and a certain reaction time, and under the existence of catalytic agent and organic solvent, so as to prepare vitamin A aldehyde, the catalytic agent is formed by a catalyzing system composed of main catalytic agent and auxiliary catalytic agent, and the main catalytic agent adopts one of 4-methoxy-1-oxo-2, 2, 6, 6-tetramethyl-piperidine, and 4-ethoxy-1-oxo-2, 2, 6, 6-tetramethyl-piperidine. The invention has the advantages that the stability of the catalytic agent is high, the catalytic activity is high, the utilization quantity is small, the reaction speed is quick, and the yield rate is high.

Description

technical field [0001] The invention relates to a synthesis process of vitamin A aldehyde. Background technique [0002] Vitamin A aldehyde is an important drug in the vitamin A class, and its market prospect is very good. At present, vitamin A alcohol is oxidized to produce vitamin A aldehyde, the chemical equation is as follows: [0003] [0004] Due to the existence of a large number of conjugated double bonds, the method is less suitable for the catalytic system of the reaction. The commonly used chemical oxidants in the past have manganese dioxide, nickel oxide, chromium oxide, etc., and the method of these chemical oxidants will consume at least more than equimolar Oxidants produce a large amount of pollutants, and the oxidation effect is difficult to guarantee, so it is difficult to apply to industrial production. In terms of catalyst selection, the following are generally used: one is to use aluminum isopropoxide to catalyze oxidation, which consumes a large amo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C403/14
Inventor 刘伟李新荣何华锋刘澎锋李靖张符沈润溥
Owner SHAOXING UNIVERSITY
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