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Method for preparing vitamin A acetate through one-pot method

A technology of acetate and vitamin, which is applied in the field of preparing vitamin A acetate in one pot, can solve the problems of excessive waste water and waste, unfavorable industrial production, complicated reaction steps, etc., and achieve the goal of improving industrial production level and reducing solvents Use and separation, low cost effect

Active Publication Date: 2013-04-17
XINFA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The above methods carry out two-step Wittig reaction respectively, the reaction steps are complicated, the reaction cycle is long, and there are many waste water and waste, the actual yield of the two steps is only about 60%.
And the C15 phosphonate must be thoroughly dried or treated before it can be used in the second step of the Wittig reaction. The existence of a small amount of water will lead to a series of side reactions such as the self-condensation of the C5 aldehyde, which will reduce the yield and complicate the post-treatment.
And it will cause production accidents such as fire, which is not conducive to industrial production

Method used

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  • Method for preparing vitamin A acetate through one-pot method
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  • Method for preparing vitamin A acetate through one-pot method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Under the protection of nitrogen, add 200 grams of N,N-dimethylformamide and 20.4 grams (0.3 moles) of solid sodium ethylate to a dry 1000 ml glass flask in sequence, cool and keep the temperature between -5 °C and 5 °C. Add dropwise a mixed solution prepared by 20.6 g (0.1 mole) of C14 aldehyde, 34.6 g (0.12 mole) of tetraethyl methylene diphosphonate and 100 g of N,N-dimethylformamide for about 2 hours Finished adding. Thereafter, the reaction was carried out at -5°C~5°C for 2.5 hours, and the conversion rate of C14 aldehyde was 99.9% by gas phase detection. The resulting intermediate C15 phosphonate was confirmed by GC-MS analysis, see figure 1 and figure 2 .

[0064] After the conversion of C14 aldehyde is completed, the reaction product intermediate does not need to be separated, and the reaction solution is cooled to -20°C, and then 17.0 grams (0.12 moles) of C5 aldehyde and 50 grams of N, N-dimethyl For the mixed solution of formamide, the dropwise addition ...

Embodiment 2

[0066] Under the protection of nitrogen, add 300 grams of N,N-dimethylformamide and 33.6 grams (0.3 moles) of potassium tert-butoxide solid to a dry 1000 ml glass flask in sequence, cool and keep the temperature between -5°C and 5°C , add dropwise a mixed solution prepared by 20.6 g (0.1 mole) of C14 aldehyde, 34.6 g (0.12 mole) of tetraethyl methylene diphosphonate and 100 g of N,N-dimethylformamide for about 2 hours The dropwise addition is completed; the insulation reaction takes 2 to 3 hours. After gas-phase detection of C14 aldehyde conversion is complete, the reaction solution is continued to cool down to -20°C, and then a mixed solution of 17.0 grams (0.12 moles) of C5 aldehyde and 50 grams of N,N-dimethylformamide is added dropwise, and the dropping temperature is controlled at -10°C~-15°C, the dropwise addition is completed in about 1 hour. After the dropwise addition, it is kept at -5°C for 2 to 3 hours. ℃), recover the solvent until no material evaporates, cool to ...

Embodiment 3

[0068] Under the protection of nitrogen, add 200 grams of N,N-dimethylformamide and 21.6 grams (0.4 moles) of sodium methoxide solid to a dry 1000 ml glass flask successively, cool, keep the temperature between -5°C and 5°C, drop Add a mixed solution prepared by 20.6 g (0.1 mole) of C14 aldehyde, 34.6 g (0.12 mole) of tetraethyl methylene diphosphonate and 100 g of N, N-dimethylformamide, dropwise for about 2 hours complete. Thereafter, the reaction was incubated for 2 to 3 hours. After gas-phase detection of C14 aldehyde conversion is complete, the reaction solution is continued to cool down to -20°C, and then a mixed solution of 17.0 grams (0.12 moles) of C5 aldehyde and 50 grams of N,N-dimethylformamide is added dropwise, and the dropping temperature is controlled at -10°C~-15°C, the dropwise addition is completed in about 1 hour. After the dropwise addition, it is kept at -5°C for 2 to 3 hours. ℃) Recover the solvent until no material evaporates, cool to room temperature...

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Abstract

The invention relates to a method for preparing vitamin A acetate through a one-pot method, which comprises the following steps: reacting C14 aldehyde and an intermediate compound C1 (tetraethyl methylenediphosphonate or tetramethyl methylenediphosphonate) under alkaline conditions to generate C15 phosphonate; and under the condition of not separating the C15 phosphonate, directly reacting the C15 phosphonate and C5 aldehyde through a one-pot method, thus preparing the vitamin A acetate. According to the method, two Wittig reaction steps are combined and performed in one pot, the technical operation is simple, the use and separation of solvent are reduced, the drying of the C15 phosphonate is avoided, the technical process is short, and the reaction is performed at a preselected temperature, thereby improving the reaction selectivity, avoiding the cryogenic operation environment and lowering the energy consumption; and meanwhile, the waste water discharge is reduced, and the method is economical and environment-friendly. The obtained vitamin A acetate has high product purity, high yield and low cost, and is beneficial to industrial production.

Description

technical field [0001] The invention relates to a method for preparing vitamin A acetate in one pot, and belongs to the technical field of production of vitamin A and its derivatives. Background technique [0002] Vitamin A and its derivatives are an important class of pharmaceuticals and feed additives, and the most commonly used vitamin A derivative is vitamin A acetate. Vitamin A acetate, also known as vitamin A acetate, retinyl acetate, vitamin A acetate, CAS number 127-47-9, is a light yellow solid powder with good fluidity. The structural formula of vitamin A acetate is as follows: [0003] [0004] Vitamin A acetate has a variety of important physiological functions, and is an essential nutrient for vision system, growth, epithelial tissue and bone development, sperm production and fetal growth and development. Vitamin A acetate plays an important role in many life processes, such as vision generation, growth, development, differentiation, metabolism, and morphog...

Claims

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Application Information

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IPC IPC(8): C07C403/12
Inventor 戚聿新陈军宋春鹏周立山李新发
Owner XINFA PHARMA
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