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Green synthesis method of vitamin C higher fatty acid ester

A technology for higher fatty acids and fatty acid esters, applied in the directions of organic chemistry, chemical recycling, etc., can solve the fundamental problems of inability to solve a large amount of waste acid water, unfavorable to large-scale production, and high production costs, achieving low cost, saving production costs, The effect of less impurities

Active Publication Date: 2021-03-12
SHANGYU NHU BIOCHEM IND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Looking at the problems existing in the current existing technologies, the sulfuric acid method, the acid chloride method, and the enzymatic method all have bottlenecks such as being unfriendly to the environment, low molar yields, and high production costs, which are very unfavorable for large-scale production
Although the sulfuric acid method patent CN105315244A innovatively adds palmitic anhydride at the later stage of the reaction to increase the overall molar yield, it still cannot solve the fundamental problem of a large amount of waste acid water

Method used

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  • Green synthesis method of vitamin C higher fatty acid ester
  • Green synthesis method of vitamin C higher fatty acid ester
  • Green synthesis method of vitamin C higher fatty acid ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] The preparation of embodiment 1 vitamin C palmitate

[0050] Put palmitic anhydride (50g, 0.101mol), vitamin C (17.61g, 0.100mol) and DMAP (0.02g) into a 250mL four-neck flask with a reflux and heating device, slowly raise the temperature to 70°C, react for 8 hours, and take a sample After HPLC detection, vitamin C residue ≤ 0.5% is qualified, stop heating, add n-hexane (200g) dropwise, drop it in 0.5 hour, cool down to 5-10°C, stir for 1 hour, filter, and cool and normalize with 0-5°C. The filter cake was washed 3 times with hexane and dried to obtain the product vitamin C palmitate (41.12 g, 0.0992 mol), which was white crystals in appearance, HPLC purity: 99.30%, and molar yield: 98.50%. H NMR spectrum see figure 2 , which is consistent with the standard product; in addition, the national standard GB1886.230-2016 of vitamin C palmitate is used for the HPLC detection method, the peak time is consistent, and the product structure can be confirmed.

Embodiment 2

[0051] The preparation of embodiment 2 vitamin C palmitate (different reaction temperature)

[0052] Put palmitic anhydride (50g, 0.101mol), vitamin C (17.61g, 0.100mol) and DMAP (0.02g) into a 250mL four-neck flask with a reflux and heating device, slowly raise the temperature to 85°C, react for 8 hours, and take a sample After HPLC detection, vitamin C residue ≤ 0.5% is qualified, stop heating, add n-hexane (200g) dropwise, drop it in 0.5 hour, cool down to 5-10°C, stir for 1 hour, filter, and cool and normalize with 0-5°C. The filter cake was washed 3 times with hexane and dried to obtain the product vitamin C palmitate (41.16 g, 0.0993 mol), which was white crystals in appearance, HPLC purity: 99.24%, and molar yield: 98.54%.

Embodiment 3

[0053] The preparation of embodiment 3 vitamin C palmitic acid esters (raw materials in different ratios)

[0054] Put palmitic anhydride (55g, 0.111mol), vitamin C (17.61g, 0.100mol) and DMAP (0.02g) into a 250mL four-neck flask with a reflux and heating device, slowly raise the temperature to 70°C, react for 8 hours, and take a sample After HPLC detection, vitamin C residue ≤ 0.5% is qualified, stop heating, add n-hexane (200g) dropwise, drop it in 0.5 hour, cool down to 5-10°C, stir for 1 hour, filter, and cool and normalize with 0-5°C. The filter cake was washed 3 times with hexane and dried to obtain the product vitamin C palmitate (41.31 g, 0.0993 mol), which was white crystals in appearance, HPLC purity: 99.67%, and molar yield: 99.33%.

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Abstract

The invention discloses a green synthesis method of vitamin C higher fatty acid ester, and the method comprises the following steps: under the catalysis of an acylation reaction catalyst, carrying outesterification reaction on vitamin C and higher fatty acid anhydride under a solvent-free condition, and carrying out after-treatment to obtain the vitamin C higher fatty acid ester. The synthesis method is environmentally friendly, low in reaction temperature, low in energy consumption, low in cost, high in molecular utilization rate of raw materials and auxiliary materials and high in yield.

Description

technical field [0001] The invention belongs to the field of vitamin synthesis, and in particular relates to a green synthesis method of vitamin C higher fatty acid esters. Background technique [0002] Water-soluble vitamin C, also known as L-ascorbic acid, is a polyhydroxy compound, which is acidic and highly reducing, and is easily oxidized into dehydrovitamin C. Vitamin C is a high-efficiency antioxidant, and many important biosynthetic processes in the human body require the participation of vitamin C. At present, vitamin C is also widely used in animal feed and food additives. In the process of application, because vitamin C has strong activity and is not easy to preserve, people often esterify vitamin C to protect the most active hydroxyl group, so as to delay the effect of vitamin C and increase the fat solubility of vitamin C. The most common vitamin C ester is vitamin C palmitate, which is a high-level fatty acid ester, and other vitamin C high-level fatty acid e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/62
CPCC07D307/62Y02P20/584
Inventor 陈晓庆王拥军刘祥洪李伟明芮书静杨鲁腾陈召峰
Owner SHANGYU NHU BIOCHEM IND
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