Preparation method of vitamin A acetate

A technology of acetate and vitamins, which is applied in the field of preparation of vitamin A acetate, can solve the problems of unfavorable environmental protection, harsh temperature requirements, and lower than -40°C, and achieve the effects of low cost, mild reaction conditions, and reduced output

Active Publication Date: 2016-09-21
肇庆巨元生化有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In the above-mentioned method for preparing pentadecyl phosphate by C14 aldehyde, strong alkali needs to be used, and a large amount of waste water is produced in the aftertreatment, which is unfavorable for environmental protection; in addition, by 1,3-two double bond pentadecyl phosphate and C5 In the method for preparing vitamin A acetate from aldehyde ester, the reaction temperature needs to be lower than -40°C, the temperature requirement is relatively strict, and the dangerous strong base DMSO sodium salt is used

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  • Preparation method of vitamin A acetate

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Effect test

Embodiment 1

[0032] A preparation method of vitamin A acetate, comprising the following steps:

[0033] Step 1) Preparation of C6 phosphate (5-(diethyl phosphate)-3-methyl-2,4-hexadiene-1-acetate):

[0034] Under nitrogen protection, add 0.15mol sodium tert-butoxide and 50mL diethyl ether into a 500mL reaction flask, stir mechanically, cool down to about 0 °C, slowly add 0.10mol methylene diphosphate tetraethyl ester dropwise, control the internal The temperature does not exceed 0 °C, and the dropwise addition is completed in about 30 minutes. After the dropwise addition, the temperature is raised to 25-30 °C and the reaction is continued for 1.0 h. After completion of the reaction, 0.10mol of C5 aldehyde ester (3-methyl-4-oxo-2-butene-1-yl acetate) dissolved in 15mL ether solution was then added dropwise, and the internal temperature was controlled not to exceed 35 ℃, about 30 minutes, the dropwise addition was completed, and the reaction was continued at 20 ℃ for 2.0 h after the dropwis...

Embodiment 2

[0040] A preparation method of vitamin A acetate, comprising the following steps:

[0041] Step 1) Preparation of C6 Phosphate:

[0042] Under nitrogen protection, add 0.143mol butyllithium and 50mL dimethylformamide into a 500mL reaction flask, cool down to about 10°C with mechanical stirring, and slowly add 0.11mol tetraethyl methylene diphosphate dropwise. The internal temperature was controlled not to exceed 10°C, the dropwise addition was completed in about 30 minutes, and the temperature was raised to 25-30°C after the dropwise addition, and the reaction was continued for 1.0 h. The reaction was completed, then 0.1mol of C5 aldehyde ester dissolved in 10ml of dimethylformamide solution was added dropwise, the internal temperature was controlled not to exceed 5°C during the dropwise addition, the dropwise addition was completed in about 30 minutes, and the temperature was continued at 0°C after the dropwise addition. The next reaction was 2.0h.

[0043]After the reactio...

Embodiment 3

[0048] A preparation method of vitamin A acetate, comprising the following steps:

[0049] Step 1) Preparation of C6 Phosphate:

[0050] Under nitrogen protection, add 0.198mol sodium hydride and 75mL ethylene glycol dimethyl ether to a 500mL reaction flask, cool down to about 30°C with mechanical stirring, and slowly add 0.18mol tetraethyl methylene diphosphate dropwise. The inner temperature was controlled not to exceed 30°C, the dropwise addition was completed in about 30 minutes, and the temperature was raised to 25-30°C after the dropwise addition, and the reaction was continued for 1.0 h. After the reaction was completed, 0.15mol of C5 aldehyde ester dissolved in 15 mL of toluene solution was added dropwise. During the dropwise addition, the internal temperature was controlled not to exceed 35°C. The dropwise addition was completed in about 30 minutes. After the dropwise addition, the reaction was continued at 35°C for 2.0 hours.

[0051] After the reaction was complete...

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Abstract

The invention provides a preparation method of vitamin A acetate. The preparation method comprises the following steps: (1) under an alkaline condition, enabling 3-methyl-4-oxo-2-buten-1-base acetate (short for C5 aldehydo-ester) and tetraethyl methylenediphosphonate to produce a condensation reaction to obtain an intermediate, namely C6 phosphate (be chemically described as 5-(phosphoric acid diethyl ester base)-3-methyl-2,4-hexadiene-1-acetate); (2) carrying out transposition on the C6 phosphate under the alkaline condition, adding C14 aldehyde (be chemically described as 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-butene-1-aldehyde) to produce a Wittig-Horner condensation reaction to generate the vitamin A acetate. The preparation method is easy in raw material obtaining, short in the synthetic route, safe in operation and suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of vitamin A acetate. Background technique [0002] Vitamin A and its derivatives are an important class of medicines for the treatment of night blindness, xerophthalmia, keratomalacia and dry skin; it can promote the growth and development of the human body, and can enhance the resistance to diseases; It is also an important feed additive. In 1947, O.Isler et al. of Roche Company developed a synthetic route of C14+C6, which was composed of C14 aldehyde (2-methyl-4-(2,6,6-trimethyl-1-cyclohexene-1- Starting from 1-yl)-3-butene-1-aldehyde), vitamin A acetate is prepared through Grignard reaction, hydrogenation, acetylation, hydroxybromination and other operations. In this synthetic route, the synthetic route is long, and the operation steps are many and cumbersome. [0003] C14 aldehydes are mentioned in other patents for the preparation of penta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C403/12
CPCC07C403/12C07F9/4078
Inventor 方泽华廖艳金刘庆辉
Owner 肇庆巨元生化有限公司
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