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Method for preparing L-ascorbic acid or D-erythorbic acid carboxylate by using acyl chloride

A technology of ascorbic acid carboxylate and erythorbic acid, which is applied in the field of preparing L-ascorbic acid carboxylate or D-erythorbic acid carboxylate, can solve the problems of many by-products, long cycle, and influence on reaction yield, and achieve The effect of mild reaction conditions, short reaction cycle and high reaction yield

Active Publication Date: 2015-04-08
江西省德兴市百勤异VC钠有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the process of not using dry HCl as a catalyst, the esterification reaction is generally carried out at a higher temperature (about 40 ° C), and the reaction time is shorter, but the -OH on the C-5 of L-ascorbic acid or D-isoascorbic acid is esterified. There are many products, which brings difficulties to separation and purification, and also affects the reaction yield; in the process of using dry HCl as a catalyst, the operation of feeding dry HCl is cumbersome, and the pollution to the environment is relatively large
[0003] In addition, according to the above method to prepare L-ascorbic acid carboxylate or D-isoascorbic acid carboxylate, there are still more complicated operations for the preparation of acid chlorides and separation and purification, and the reaction by-products of acid chloride preparation SO 2 and HCl have a greater impact on the environment, and the cycle from carboxylic acid to product (L-ascorbic acid carboxylate or D-isoascorbic acid carboxylate) is relatively long.

Method used

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  • Method for preparing L-ascorbic acid or D-erythorbic acid carboxylate by using acyl chloride
  • Method for preparing L-ascorbic acid or D-erythorbic acid carboxylate by using acyl chloride
  • Method for preparing L-ascorbic acid or D-erythorbic acid carboxylate by using acyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] L-Ascorbyl Palmitate preparation.

[0018] Add 2.564g (10mmol) palmitic acid and 15mL DMAc and 5mL CH to the reaction flask 2 Cl 2 , stirred and dissolved at room temperature, cooled to 0°C and added dropwise 1.368g (11mmol) SOCl 2 , 0°C, reacted for 2h under stirring, then added 2.818g (16mmol) L-ascorbic acid, raised the temperature and maintained at 25°C for 8h. After the reaction was completed, 50 mL of ethyl acetate and 100 mL of distilled water were added to the reaction mixture, and stirred at room temperature for 1 h. Transfer to a separatory funnel, extract the separated aqueous layer twice with 80 mL ethyl acetate, and combine the organic layers. The organic layer was washed with saturated NaCl aqueous solution, anhydrous NaCl 2 SO 4 After drying, filtering, rotary evaporation of ethyl acetate, and oil pump vacuum drying for 1 h, the crude product was obtained. The crude product was recrystallized from a mixed solvent of ethyl acetate-petroleum ether t...

Embodiment 2

[0021] L-Ascorbyl Benzoate preparation.

[0022] Add 1.221g (10mmol) benzoic acid and 10mL DMAc to the reaction flask, stir and dissolve at room temperature, and add 1.368g (11mmol) SOCl dropwise after cooling to 0°C 2 After reacting for 2 hours at 0°C under magnetic stirring, 2.818g (16mmol) of L-ascorbic acid was added, and the temperature was raised and maintained at 25°C for 10h. The separation and purification method of the product was the same as in Example 1, and 1.761 g of white powder was obtained, with a content of 98.9%, a melting point of 180.5-183.3° C., and a reaction yield based on benzoic acid of 62.8%.

[0023] NMP was used to replace the above DMAc, and other reaction conditions were the same as the separation and purification conditions, and the reaction yield based on benzoic acid was 63.5%.

Embodiment 3

[0025] D-Erythorbyl Cinnamate preparation.

[0026] Add 1.482g (10mmol) cinnamic acid and 20mL DMAc to the reaction flask, stir and dissolve at room temperature, and add 1.368g (11mmol) SOCl dropwise after cooling to 0°C 2 , 0°C, reacted for 2h under stirring, then added 5.284 (30mmol) L-ascorbic acid, raised the temperature and maintained at 25°C for 12h. The separation and purification method of the product was the same as in Example 1 to obtain 2.254 g of a pale yellow waxy solid with a melting point of 57.5-61.2° C. and a reaction yield based on cinnamic acid of 73.6%.

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Abstract

The invention relates to a method for preparing L-ascorbic acid or D-erythorbic acid carboxylate by using acyl chloride. According to the method, with DMAc (N,N-dimethylacetamide) or NMP (N-methyl pyrrolidone) as a solvent, a catalyst and an acid-binding agent in reaction of carboxylic acid and SOCl2, acryl chloride directly reacts with L-ascorbic acid or D-erythorbic acid without being separated to prepare L-ascorbic acid or D-erythorbic acid carboxylate. Compared with the existing acryl chloride method, the method disclosed by the invention has the characteristics of simple operation, little dosage of SOCl2, short reaction period, mild reaction conditions, high reaction yield, environmental friendliness and the like, and a used solvent does not need to be dried in advance.

Description

technical field [0001] The present invention relates to the fine chemical industry field, specifically, it is to provide a kind of using DMAc or NMP as carboxylic acid and SOCl 2 The reaction solvent, catalyst and acid-binding agent, the obtained acid chloride is directly reacted with L-ascorbic acid or D-isoascorbic acid to prepare L-ascorbic acid carboxylate or D-isoascorbic acid carboxylate without separation. Background technique [0002] The synthesis method of L-ascorbic acid or D-isoascorbic acid carboxylate is acid-catalyzed or enzyme-catalyzed direct esterification method, transesterification method, and acid chloride method. The acid chloride method is especially suitable for the ester-forming reaction of carboxylic acids with poor activity or large steric hindrance and L-ascorbic acid or D-isoascorbic acid. The preparation of L-ascorbic acid or D-isoascorbic acid carboxylate by the acid chloride method is usually to first combine the carboxylic acid with SOCl 2 ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/62
CPCC07D307/62
Inventor 郑大贵余泗莲祝显红周强余彬
Owner 江西省德兴市百勤异VC钠有限公司
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