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Preparation method of vitamin A acetate

A technology of acetate and vitamin, which is applied in the field of preparation of vitamin A acetate, can solve problems such as difficult to handle, high price of triphenylphosphine, difficult production control, etc., and achieve an effect that is beneficial to industrial production

Active Publication Date: 2021-03-09
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The two routes have their own defects. The C14+C6 route requires more than 50 kinds of raw materials, the reaction steps are long, the fixed investment is large, and it is an intermittent series reaction, which is not easy to control production. In addition, there are safety problems in the production of double Grignard reagents. Large security risks when industrialization scales up
The raw material triphenylphosphine used in the C15+C5 route is expensive, and a large amount of triphenylphosphine oxide solid waste is produced by the reaction, which is difficult to handle; in addition, the VA produced by this route contains a large amount of cis-isomers, which reduces the value of use
[0009] Patent CN110143874A reports the use of a strong base to catalyze the reaction of β-ionone and 2-chloropropionate, followed by selective hydrogenation to prepare VA, which avoids triphenylphosphine oxide very well, but uses a strong base in the reaction process , there is a side reaction of condensation of the raw material itself, the reaction selectivity is poor, and the cost is high

Method used

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  • Preparation method of vitamin A acetate
  • Preparation method of vitamin A acetate
  • Preparation method of vitamin A acetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Add 1249g (10mol) of bromoethanol and 290g (5mol) of acetone to a 3L three-necked flask, heat up to 40°C, add 1g (0.01mol) of concentrated sulfuric acid, keep the temperature for 6 hours, and the single-pass conversion rate of acetone is 26%. Separation by distillation, the temperature was 80°C, the pressure was 10KPaA, the number of plates = 50, and the reflux ratio was 10:1, to obtain 316.5g (1.1mol) of ketal compound with a GC purity of 99.8%. The ketal compound was qualitatively analyzed by NMR, 1H NMR (300MHz, CDCl3): δ=3.96(t, JH-H=6.3Hz, 4H), 3.69(t, JH-H=6.3Hz, 4H), 1.25(s, 6H).

[0063] Add 298.2g (2.1mol) of pentacarbonaldehyde, 500g of tetrahydrofuran, 49.9g (2.08mol) of magnesium powder into a 3L three-necked flask, raise the temperature to 60°C, and slowly drop the mixture of 289.9g (1mol) of ketal compound and 300g of tetrahydrofuran Add it to the three-necked flask, the dropping time is 4 hours, the reaction temperature during the dropping process does n...

Embodiment 2

[0067] Add 2498g (20mol) of bromoethanol and 290g (5mol) of acetone to a 3L three-necked flask, heat up to 50°C, add 0.86g (0.005mol) of p-toluenesulfonic acid, keep the temperature for 4 hours, and the single-pass conversion rate of acetone is 36%. The liquid was subjected to rectification and separation at a temperature of 120°C, a pressure of 15KPaA, the number of plates=50, and a reflux ratio of 10:1 to obtain 434.8g (1.5mol) of ketal compound 1 with a GC purity of 99.8%.

[0068] Add 269.8g (1.9mol) of pentacarbonaldehyde, 500g of tetrahydrofuran, 45.5g (1.9mol) of magnesium chips into a 3L three-necked flask, raise the temperature to 50°C, and slowly drop the mixture of 289.9g (1mol) of ketal compound and 300g of tetrahydrofuran Add it into the three-necked flask, the dropping time is 5h, the reaction temperature during the dropping process does not exceed 65°C, continue to react at 60°C for 2h after the dropping is completed, and slowly add the reaction solution into the...

Embodiment 3

[0072] Add 6245g (50mol) of bromoethanol and 290g (5mol) of acetone to a 3L three-necked flask, heat up to 50°C, add 1.72g (0.01mol) of p-toluenesulfonic acid, keep the temperature for 4 hours, and the single-pass conversion rate of acetone is 38%. The liquid was subjected to rectification and separation at a temperature of 50°C, a pressure of 2KPaA, the number of plates = 50, and a reflux ratio of 10:1 to obtain 463.8g (1.6mol) of ketal compound with a GC purity of 99.7%.

[0073] Add 255.6g (1.8mol) pentacarbonaldehyde, 1000g tetrahydrofuran, 43.2g (1.8mol) magnesium chips to a 3L three-necked flask, raise the temperature to 40°C, and slowly drop the mixture of 289.9g (1mol) ketal compound and 300g tetrahydrofuran Add it into the three-necked flask, the dropping time is 2h, the reaction temperature during the dropping process does not exceed 65°C, continue the reaction at 50°C for 5h after the dropping is completed, and slowly add the reaction solution into a 5L three-necked ...

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Abstract

The invention provides a preparation method of vitamin A acetate, which comprises the following steps: reacting bromoethanol with acetone to obtain a ketal compound, preparing a Grignard reagent fromthe ketal compound, reacting the Grignard reagent with C5 aldehyde to obtain heptanol, reacting the heptanol with triphenylphosphine to prepare heptacarbon phosphine salt, and further reacting the heptacarbon phosphine salt with ionone to obtain the vitamin A acetate. According to the present invention, a C13 + C7 vitamin A acetate synthesis route is provided, such that the yield of the vitamin Aacetate is improved, the process cost is reduced, and the industrial production is easily achieved.

Description

technical field [0001] The invention relates to a method for preparing vitamin A acetate, in particular to a method for preparing vitamin A acetate by Wittig reaction. Background technique [0002] Vitamin A acetate is an important class of nutritional chemicals, which can promote the growth and development of the human body, and can enhance the resistance to diseases. [0003] Vitamin A acetate is used for vitamin A deficiency. This vitamin is fat-soluble and is an essential factor for regulating the growth and health of epithelial tissue cells. It makes the surface of rough and aging skin thinner, promotes the normalization of cell metabolism, and has an obvious wrinkle-removing effect. At present, vitamin A acetate has been widely used in industries such as medicine, food additives, feed additives and cosmetics, and its preparation and synthesis have always attracted much attention. [0004] At present, there are mainly two technical routes for the synthesis of vitamin A...

Claims

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Application Information

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IPC IPC(8): C07C403/12
CPCC07C403/12C07F9/5442C07C67/293C07C41/56C07C2601/16C07C69/145C07C43/303
Inventor 刘英瑞孔令晓李莉高洪坤郭劲资张涛吕英东
Owner WANHUA CHEM GRP CO LTD