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Enzyme-catalyzed method for preparing vitamin A palmitate

A technology for the preparation of palmitate and catalysis, applied in the direction of fermentation, etc., can solve the problems of lower alcohol residue, high cost, cumbersome steps, etc., and achieves the effects of mild reaction conditions, good product quality, and high reaction yield.

Active Publication Date: 2019-10-18
XIAMEN KINGDOMWAY VI TAMIN INC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] 1. Vitamin A acetate uses immobilized enzymes to catalyze the synthesis of vitamin A palmitate in two steps, and it is filtered many times, and the steps are cumbersome;
[0008] 2. Vitamin A acetate reacts with lower alcohols, and the immobilized esterase is filtered out. The filtrate needs to be decompressed to evaporate excess lower alcohols to obtain vitamin A alcohol. Because vitamin A alcohol is unstable, vitamin A alcohol is easy to deteriorate when heated during the process, thus affecting Product quality and appearance;
[0009] 3. Vitamin A acetate reacts with lower alcohols, and the immobilized esterase is filtered out. The excess lower alcohols are evaporated from the filtrate under reduced pressure to obtain vitamin A alcohols. The concentration of lower alcohols is difficult to control, so that the lower alcohols in vitamin A alcohols remain. Subsequent reaction with palmitic acid produces by-products, which affect the quality of vitamin A palmitate
[0011] 1. The use of high-grade fatty acid anhydrides has a high cost;
[0012] 2. The use of vitamin A alcohol has poor stability, and vitamin A alcohol is easy to deteriorate, thereby affecting product quality and appearance, and increasing post-processing costs

Method used

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  • Enzyme-catalyzed method for preparing vitamin A palmitate
  • Enzyme-catalyzed method for preparing vitamin A palmitate
  • Enzyme-catalyzed method for preparing vitamin A palmitate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Vitamin A acetate (10g, purity 95.35%, 29.03mmol) and methyl palmitate (8.23g, 30.48mmol) were added in cyclohexane (50ml), stirred for 30min, after fully dissolving, lipase Novozyme 435 was added ( 50 g), stirred, vacuumized, and the temperature of the enzyme-catalyzed transesterification reaction was controlled by adjusting the vacuum to be 25 ° C. At the same time, the reaction product methyl paraacetate and a small amount of cyclohexane were separated through the rectification column. After reacting for 10 hours, the feed liquid was filtered. Filter out lipase, add alumina (15g) to the filtrate, stir for 30min, filter to remove alumina. The filtrate was evaporated under reduced pressure to recover n-hexane to obtain 15.19 g of light yellow oil, which was analyzed according to the method of USP28. The results showed that the purity of vitamin A palmitate was 1.7566 million IU / g, equivalent to a content of 96.62%. The pure yield is 96.34%.

Embodiment 2

[0036] Add vitamin A acetate (10g, purity 96.28%, 29.31mmol) and ethyl palmitate (9.17g, 32.24mmol) in n-heptane (100ml), stir for 30min, after fully dissolving, add lipase Novozyme 435 ( 90g), stirred, vacuumized, and the temperature of the enzyme-catalyzed transesterification reaction was controlled by adjusting the vacuum to be 30°C. At the same time, the reaction by-product ethyl acetate and a small amount of n-heptane were separated through the rectification column. After reacting for 8 hours, the feed liquid was filtered. Filter out lipase, add diatomaceous earth (30g) to the filtrate, stir for 30min, filter to remove diatomite. The filtrate was evaporated under reduced pressure to recover n-heptane to obtain 15.34 g of light yellow oil, which was analyzed according to the method of USP28. The results showed that the purity of vitamin A palmitate was 1.7622 million IU / g, equivalent to a content of 96.93%. The pure yield is 96.65%.

Embodiment 3

[0038] Add vitamin A acetate (10g, purity 95.68%, 29.13mmol) and isopropyl palmitate (10g, 33.50mmol) in n-octane (150ml), stir for 30min, after fully dissolving, add lipase Novozyme 435 ( 120g), stirred, vacuumized, and the temperature of the enzyme-catalyzed transesterification reaction was controlled to be 40°C by adjusting the vacuum, and the reaction by-product isopropyl acetate and a small amount of n-octane were separated through the rectification column. After reacting for 6 hours, the feed liquid was filtered. Filter out the lipase, add aluminum oxide (30 g) to the filtrate, stir for 30 min, and filter to remove the aluminum oxide. The filtrate was evaporated under reduced pressure to recover n-octane to obtain 15.21 g of light yellow oil, which was analyzed according to the method of USP28. The results showed that the purity of vitamin A palmitate was 1.7587 million IU / g, equivalent to a content of 96.73%. The pure yield is 96.22%.

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Abstract

The invention provides a method for preparing vitamin A palmitate by enzyme catalysis, and relates to a synthesis method of vitamin A palmitate. The method comprises the following steps of (1) dissolving the vitamin A palmitate and low-grade fatty alcohol palmitate into an organic solvent, and adding lipase; (2) performing vacuum pumping from a condenser, performing enzyme catalysis ester exchange reaction, and separating out a reaction byproduct of low-grade fatty alcohol acetate and an organic solvent through a rectifying column; (3) removing lipase from reaction material liquid, adding an adsorbent for adsorbing remained low-grade fatty alcohol palmitate, and filtering out the vitamin A palmitate solution; and (4) performing organic solvent reduced pressure evaporation to obtain the vitamin A palmitate. The oxidation cannot easily occur; meanwhile, the enzyme catalysis ester exchange is used during the reaction; the reaction conditions are mild; the side reactions can be effectively inhibited; the operation is simple; the reaction yield is high; and the product quality is high.

Description

technical field [0001] The invention relates to a synthesis method of vitamin A palmitate, in particular to an enzyme-catalyzed method for preparing vitamin A palmitate. Background technique [0002] Vitamin A palmitate is a known compound whose structural formula is as follows: [0003] [0004] Vitamin A palmitate has been widely used as medicine, food additive and feed additive etc. Various synthetic methods have been reported. [0005] The applicant disclosed a synthesis method of vitamin A palmitate in Chinese patent CN102363606B, using vitamin A alcohol and halogenated amide dissolved in an organic solvent, then adding a phosphorus compound for halogen replacement reaction, and filtering to remove by-products generated during the reaction process , the filtrate is cooled to crystallization to obtain a vitamin A halogenated product; the vitamin A halogenated product and palmitate are dissolved in an organic solvent, and after adding an organic base to react, severa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P23/00
Inventor 潘必文何剑洋陈师伟严春荣朱俊岩
Owner XIAMEN KINGDOMWAY VI TAMIN INC
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