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Preparation method of retinyl acetate

A technology of acetate and vitamin, applied in the field of preparation of vitamin A acetate, can solve the problems of long reaction steps, difficult handling, safety problems in the production of double Grignard reagents, etc., and achieves the effects of mild reaction conditions and avoiding three wastes

Active Publication Date: 2019-08-20
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] 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 a series reaction, which is not easy to control production. In addition, there are still safety problems in the production of double Grignard reagents.
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

Method used

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  • Preparation method of retinyl acetate
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  • Preparation method of retinyl acetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] In a 2L three-necked flask, 200g (1.0mol) of β-ionone and 150g (1.2mol) of methyl 2-chloropropionate were mixed, cooled to -40°C, and 280ml of 30%wt sodium methoxide methanol solution was added dropwise ( 1.4mol), the temperature should not exceed -35°C. After the dropwise addition, react at -40°C to -35°C for 4 hours. The cooling bath was removed, and the temperature in the system was naturally raised to 10°C. Add 500g of water and hydrolyze at 40-45°C for 30 minutes. After standing still, the oil layer was separated; the water layer was extracted with petroleum ether 300mL×3. The extract was combined with the oil layer and washed with 1% aqueous acetic acid until the pH reached 7. After recovering petroleum ether, distill under reduced pressure, collect 110 ℃ ~ 130 ℃ (absolute pressure 100Pa) fraction, which is intermediate I197g (0.85mol), its content is 95% according to gas chromatography, it is a yellow oil, and the yield is 85% . Intermediate I is qualitative...

Embodiment 2

[0055] In a 3L three-necked flask, 200g (1.0mol) of β-ionone and 209g (1.5mol) of ethyl 2-chloropropionate were mixed, cooled to -25°C, and 650ml of 18%wt sodium ethylate ethanol solution was added dropwise ( 1.5mol), the temperature should not exceed -20°C. After the dropwise addition, react at -25°C to -20°C for 3 hours. The cooling bath was removed, and the temperature in the system was naturally raised to 10°C. Add 800g of water and hydrolyze at 40-45°C for 30 minutes. After standing, the oil layer was separated; the water layer was extracted with petroleum ether 400mL×3. The extract was combined with the oil layer and washed with 1% aqueous acetic acid until the pH reached 7. After recovering petroleum ether, distill under reduced pressure, collect 110 ℃ ~ 130 ℃ (absolute pressure 100Pa) fraction, which is intermediate I194g (0.84mol), its content is 95% according to gas chromatography, it is a yellow oil, and the yield is 84% .

[0056] Add 600g of methylene chlorid...

Embodiment 3

[0059] In a 3L three-necked flask, mix 200g (1.0mol) of β-ionone and 277g (1.8mol) of isopropyl 2-chloropropionate, cool to 0°C, and add dropwise 1000ml of 2mol / L potassium tert-butoxide solution (2.0mol), the temperature is controlled not to exceed 5°C. After the dropwise addition, react at 0°C to 5°C for 2 hours. The cooling bath was removed, and the temperature in the system was naturally raised to 10°C. Add 800g of water and hydrolyze at 40-45°C for 30 minutes. After standing, the oil layer was separated; the water layer was extracted with petroleum ether 400mL×3. The extract was combined with the oil layer and washed with 1% aqueous acetic acid until the pH reached 7. After recovering petroleum ether, distill under reduced pressure, collect 110°C-130°C (absolute pressure 100Pa) fraction, which is intermediate I206g (0.89mol), its content is 95% by gas chromatography, it is a yellow oil, and the yield is 89% .

[0060] Add 600g of isopropanol, 154g of five-carbon alde...

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Abstract

The invention provides a preparation method of retinyl acetate. The method comprises the following steps: performing a condensation reaction on beta-ionone and 2-chloropropionate under the action of astrong alkali, and performing hydrolysis decarboxylation to form an intermediate I; performing a condensation reaction on the intermediate I and pentaaldehyde to produce an intermediate II; and performing a hydrogenation reaction on the intermediate II under the action of a catalyst, and performing a dehydration reaction to obtain the retinyl acetate. The method provided by the invention avoids the disadvantages of a current process and has an economical and effective process route.

Description

technical field [0001] The invention belongs to the field of fine chemical synthesis, and in particular relates to a preparation method of vitamin A acetate. 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. At the same time, vitamin A acetate is also an important feed additive, which has various physiological functions such as promoting the synthesis of animal immunoglobulins, promoting growth and reproduction. [0003] At present, there are mainly two technical routes for the synthesis of vitamin A acetate in industry. One is the C14+C6 route: [0004] [0005] The other is the C15+C5 route: [0006] [0007] 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 a series reaction, which is not eas...

Claims

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Application Information

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IPC IPC(8): C07C67/297C07C69/145
CPCC07C45/68C07C67/293C07C67/297C07C2601/16C07C49/21C07C69/145
Inventor 吕英东张昊张涛黎源
Owner WANHUA CHEM GRP CO LTD
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