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A kind of synthetic method of sucrose-6-acetate

A synthetic method and acetate technology, applied in chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve the problems of toxic pollution, high reaction temperature, and large amount of expensive raw materials, and achieve low cost and high yield rate effect

Inactive Publication Date: 2016-04-20
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Sucrose-6-acetate is an important intermediate for the synthesis of sucralose, but there are many problems in the current process, such as the large amount of expensive raw materials used, and the large amount of toxic reagents used in some traditional processes. Toxic raw materials such as butyl tin oxide, the reaction process will cause a large number of toxic pollutants, the reaction temperature is usually required to be high, and the product yield is not high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 20ml of deionized water, 60ml of DMF, 3.62ml of pyridine (0.045mol), and 5.13g of sucrose (0.015mol) into a 250ml round bottom flask, stir mechanically, cool down to 0-5°C in a cold well; keep for 1 hour, the temperature is stable Finally, 2.84ml of acetic anhydride (0.03mol) was mixed in 15ml of DMF solvent and added dropwise through a constant pressure dropping funnel. The dropping time continued for 40 minutes. During the reaction, the stirring was at 400 rpm, and the temperature continued to be maintained at 0-5 ℃, the reaction is completed after 4 hours of reaction, then most of the water and DMF solvent in the reaction solution are evaporated to dryness, and a mixture of acetone and methanol is added at low temperature (the volume ratio of acetone and methanol is 2:1) -5 ~ 0 ℃ Recrystallized, washed with acetone after filtration, and finally dried in a vacuum drying oven to obtain white crystals, which were found to be target molecular weight 429.13 by mass spe...

Embodiment 2

[0025] Add 18ml of deionized water, 72ml of DMF, 3.0ml (0.037mol) of pyridine (0.037mol), and 4.5g (0.013mol) of sucrose into a 250ml round bottom flask, mechanically stir and cool to 0-5°C in a cold well; keep for 0.5 hours , after the temperature stabilized, 2.36ml (0.025mol) of acetic anhydride was mixed in 20ml of DMF solvent and added dropwise through a constant pressure dropping funnel. The dropping time continued for 30 minutes, and the reaction was stirred at 500 rpm, and the temperature continued to be maintained at 0~5℃, the reaction is finished after 5 hours of reaction, then most of the water and DMF solvent in the reaction solution are evaporated to dryness, and acetone methanol solution (2:1) is added at low temperature for recrystallization at -5~0℃, after filtration Wash with acetone, and finally dry in a vacuum oven to obtain white crystals, which are proved to be target molecular weight 429.13 by mass spectrometry, and can be determined to be sucrose-6-acetate...

Embodiment 3

[0027] Add 30ml of deionized water, 70ml of DMF, 5.8ml (0.041mol) of triethylamine, and 6g (0.0175mol) of sucrose into a 250ml round bottom flask, stir mechanically, cool to 0-5°C in a cold well; keep for 1 hour, the temperature After stabilization, mix 3.21ml (0.034mol) of acetic anhydride in 20ml of DMF solvent and drop it through a constant pressure dropping funnel. The dropping time lasts for 60 minutes. During the reaction, stir at 600 rpm and keep the temperature at 0~ 5°C, reacted for 6 hours, then evaporated most of the water and DMF solvent in the reaction solution to dryness, added acetone methanol (2:1) at low temperature for recrystallization at -5~0°C, washed with acetone after filtration, and finally Dry in a vacuum oven. It is proved by mass spectrometry that the target molecular weight is 429.13, which can be determined to be sucrose-6-acetate, and the yield is 5.23g. The conversion rate was 77.8%.

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PUM

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Abstract

The invention discloses a synthesis method of sugar cane-6-acetic acid ester. The synthesis method of the sugar cane-6-acetic acid ester comprises the following steps: in a mixed solvent of water and dimethyl formamide, mixing and dissolving sugar cane and an acid-binding agent at the temperature of 0-5 DEG C; dropwise adding a dimethyl formamide solution of acetic anhydride at 0-5 DEG C under a stirring condition, and reacting for 4-6 hours; after the reaction is finished, carrying out reduced pressure distillation for removing the water and dimethyl formamide solvents, adding a mixed solvent of acetone and methyl alcohol, recrystallizing, filtering, washing and drying, thus obtaining the sugar cane-6-acetic acid ester product. The synthesis method of the sugar cane-6-acetic acid ester has the advantages that acetic anhydride is used for doing sugar cane-6 hydroxyl in a new reaction system, so that an expensive and toxic reagent is not used, cost is low, and environmental friendliness is realized; reaction is carried out at a low temperature, so that product quality and yield can be improved, and the yield can be 72-85%.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a preparation method of sucrose-6-acetate. Background technique [0002] Sucralose, also known as sucralose, is a new type of non-nutritional high-power sweetener artificially synthesized from sucrose. In 1976, the research team of British Professor Leslie Hough and TateLyle Company discovered and synthesized sucralose, which entered the market in 1988. After more than ten years of pharmacological experiments, it has been proved that it is absolutely harmless to humans. Sucralose can be eaten by patients with obesity, cardiovascular disease and diabetes. It is a new type of functional high-power sweetener. There are more than 10 sucralose manufacturers in my country now, and only two or three have formed a certain scale, and the production capacity can reach about 5,000 tons. Although the previous situation of only relying on imports has been broken, the p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H13/06C07H1/00
Inventor 郭成叶飞唐拾贵郭凯韦萍
Owner NANJING TECH UNIV