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Synthesis method of ascorbyl tetraisopalmitate

A technology of ascorbic acid and palmitate, which is applied in the direction of organic chemistry, can solve the problems of miscibility of solvents and viscous mixtures, increase the difficulty of post-processing, and reduce product yields, and achieve full reaction, easy industrial implementation, and simple equipment Effect

Inactive Publication Date: 2018-05-25
SPEC CHEM IND INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is more complicated, and repeated operations will reduce the product yield. A large amount of diethyl ketone is used, and the production cost is high. Diethyl ketone and water are very miscible. Simply using this solvent for extraction will easily lead to solvent and viscous mixture. Miscible, not easy to separate, resulting in a decrease in yield
In addition, acid is artificially added during the isomerization process, which increases the difficulty of post-processing
The target product and palmitic acid are easily soluble in diethyl ketone and difficult to separate

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A kind of synthetic method of ascorbyl tetraisopalmitate comprises the steps:

[0026] (1) Preparation of 2-hexyldecanoyl chloride

[0027] 153.8g (600.0mmol) of 2-hexyldecanoic acid was added to a 2.0L four-neck flask, then 1.0L of dichloromethane was added, and 107.1g (900.0mmol) of thionyl chloride was added dropwise. After adding, it was heated to reflux temperature and stirred for 1h. The reaction solution was concentrated to obtain crude 2-hexyldecanoyl chloride, which was purified by distillation to obtain 152.0 g of a colorless transparent liquid with a yield of 92.1%.

[0028] (2) Preparation of Ascorbyl Tetraisopalmitate

[0029] Add 21.1g (119.8mmol) of L-ascorbic acid to a 1.0L four-necked flask, add 300ml of N-methylpyrrolidone and 56.9g (718.8mmol) of pyridine under nitrogen protection, and start to add 148.2g (539.1mmol) of 2-hexyl Decanoyl chloride, stirred at 0-5°C for 3 hours, added methyl tert-butyl ether and 5% hydrochloric acid to the reaction li...

Embodiment 2

[0031] A kind of synthetic method of ascorbyl tetraisopalmitate comprises the steps:

[0032] (1) Preparation of 2-hexyldecanoyl chloride

[0033] Add 230.8g (900.0mmol) 2-hexyldecanoic acid to a 3.0L four-neck flask, then add 1.5L dichloromethane, then add 98.9g (720.0mmol) phosphorus trichloride, heat to reflux temperature after addition, and stir for 2h . The reaction solution was concentrated to obtain crude 2-hexyldecanoyl chloride, which was purified by distillation to obtain 222.8 g of a colorless transparent liquid with a yield of 90.1%.

[0034] (2) Preparation of Ascorbyl Tetraisopalmitate

[0035] Add 30.6g (173.7mmol) of L-ascorbic acid to a 1.0L four-neck flask, add 400ml of N-methylpyrrolidone and 105.5g (1042.2mmol) of triethylamine under nitrogen protection, and start to add 214.9g (781.7mmol) of triethylamine dropwise under ice bath 2-Hexyldecanoyl chloride, stirred at 10-15°C for 1 h, added methyl tert-butyl ether and 5% hydrochloric acid to the reaction l...

Embodiment 3

[0037] A kind of synthetic method of ascorbyl tetraisopalmitate comprises the steps:

[0038] (1) Preparation of 2-hexyldecanoyl chloride

[0039]Add 184.6g (720mmol) of 2-hexyldecanoic acid to a 3.0L four-neck flask, then add 1.2L of dichloromethane, and then add 128.5g (1080.0mmol) of thionyl chloride. After adding, it was heated to reflux temperature and stirred for 4h. The reaction solution was concentrated to obtain crude 2-hexyldecanoyl chloride, which was purified by distillation to obtain 182.0 g of a colorless transparent liquid with a yield of 91.9%.

[0040] (2) Preparation of Ascorbyl Tetraisopalmitate

[0041] Add 26.5 (150.5 mmol) g L-ascorbic acid to a 1.0 L four-neck flask, add 400 ml N, N-dimethylformamide and 71.4 g (903.0 mmol) pyridine under nitrogen protection, and start to add 186.1 g (677.2 mmol) dropwise under ice bath 2-Hexyldecanoyl chloride, stirred at 5-10°C for 2 hours, added methyl tert-butyl ether and 5% hydrochloric acid to the reaction solut...

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PUM

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Abstract

The invention discloses a synthesis method of ascorbyl tetraisopalmitate. The method comprises the following steps of reacting to generate 2-hexyldecanoyl chloride by utilizing 2-hexyldecanoic acid and a chlorinating reagent; enabling the 2-hexyldecanoyl chloride to react with L-ascorbic acid to generate the ascorbyl tetraisopalmitate; preparing the ascorbyl tetraisopalmitate through post treatment of extraction, water scrubbing, drying, concentration, purification and the like. The method is stable in yield, lower in cost, simple in equipment and less in investment and is easy to industriallyimplementation.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a method for synthesizing ascorbyl tetraisopalmitate. Background technique [0002] Ascorbyl tetraisopalmitate, as an important ascorbic acid derivative, is a fat-soluble antioxidant. It not only retains the anti-oxidation of ascorbic acid, namely vitamin C, and the pharmacological effects of preventing vascular sclerosis and treating sepsis, but also has fat solubility. It is a highly efficient and multi-functional additive that extends the scope of application of the product. In medicine, it is used as an antioxidant, stabilizer, and synergist in medicine; in health food, it is mainly used as an antioxidant and nutritional enhancer for human body; in the field of cosmetics, it is mainly used as an additive for cosmetics. [0003] Ascorbyl tetraisopalmitate is stable at high temperature, has good solubility in oil, and has excellent transdermal absorption ability, and can be d...

Claims

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Application Information

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IPC IPC(8): C07D307/62
CPCC07D307/62
Inventor 查建生徐金荣
Owner SPEC CHEM IND INC
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