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Method for preparing sucralose-6-acetate by tandem reaction

A technology of sucralose and series reaction, which is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problems of high reaction temperature requirements, increased difficulty in operation, long reaction time, etc., and reach the reaction temperature Low requirements, short reaction time, and less waste

Active Publication Date: 2015-04-08
ZHEJIANG HAISEN PHARMACY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The difficulty of this process lies in the second step of chlorination reaction. Most domestic processes use DMF as solvent, and chlorinated reagents are used for chlorination. The reaction temperature is high and the reaction time is long. Due to the generation of hydrogen chloride and sulfur dioxide gas during the reaction, if it cannot be timely and effective Excluding it will lead to carbonization of the product, and the operation will increase

Method used

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  • Method for preparing sucralose-6-acetate by tandem reaction

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] In a 250 ml three-necked flask, add 34.2 g (0.1 mol) of sucrose, 16.8 g (0.14 mol) of trimethyl orthoacetate and 6.8 g of p-toluenesulfonic acid, stir and react at 40°C for 5 hours, then add appropriate amount of deionized water 4 ml , stirred at room temperature for 2 hours, then added 92.5 grams (0.5 moles) of tri-tert-butylamine, and after stirring at room temperature for 5 hours, added 63.3 grams (0.5 moles) of benzyl chloride, reacted at 100 ° C for 10 hours, and used ethyl acetate 100 × 3 ml Extraction, concentration, and recrystallization yielded 19 grams of sucralose-6-acetate product, with a yield of 48%. Melting point: 75~77℃; the purity of the product is over 98.0% by HPLC.

Embodiment 2

[0031] In a 250 ml three-necked flask, add 34.2 g (0.1 mol) of sucrose, 16.8 g (0.14 mol) of trimethyl orthoacetate and 5.1 g of p-toluenesulfonic acid, stir and react at 40°C for 5 hours, then add an appropriate amount of deionized water 5 ml , stirred at room temperature for 2 hours, then added 55.5 g (0.3 mol) of tri-tert-butylamine, after stirring at room temperature for 5 hours, added 38 g (0.3 mol) of benzyl chloride, reacted at 110 ° C for 6 hours, and added 100 × 3 ml of ethyl acetate Extraction, concentration, and recrystallization yielded 19 grams of sucralose-6-acetate product, with a yield of 48%. Melting point: 75~77℃; the purity of the product is over 98.0% by HPLC.

Embodiment 3

[0033] In a 250 ml three-necked flask, add 34.2 g (0.1 mol) of sucrose, 16.8 g (0.14 mol) of trimethyl orthoacetate and 0.5 g of p-toluenesulfonic acid, stir and react at 40°C for 5 hours, then add an appropriate amount of deionized water 3 ml , stirred at room temperature for 2 hours, then added 55.5 grams (0.3 moles) of tri-tert-butylamine, after stirring at room temperature for 5 hours, added 38 grams (0.3 moles) of benzyl chloride, reacted at 90 ° C for 10 hours, and used ethyl acetate 100 × 3 ml Extraction, concentration, and recrystallization yielded 19 grams of sucralose-6-acetate product, with a yield of 48%. Melting point: 75~77℃; the purity of the product is over 98.0% by HPLC.

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Abstract

The invention aims at providing a method for preparing sucralose-6-acetate by tandem reaction of quaternary ammonium salt chlorination. The tandem reaction is adopted to finish three steps of a production process, a first-step reaction is esterification of sucrose C-6 hydroxy, the second-step reaction is chlorination of sucrose C-6 acetic acid ester, and the third-step reaction is separation purification of sucralose-6-acetate. The method for preparing the sucralose-6-acetate by the tandem reaction has the advantages that the method is low in requirements on reaction temperature, short in reaction time, good in technical performance, free of hydrogen chloride and sulfur dioxide, few in three wastes (waste water, waste gas and waste residues), convenient for post-treatment and reusable in reaction system and is an economical and practical environment-friendly technology.

Description

technical field [0001] The invention relates to a method for preparing sucralose-6-acetate by series reaction technology, in particular to a method for chlorinating sucrose-6-acetate by using a quaternary ammonium salt in the series reaction. Background technique [0002] Sucralose is a white powder product, very soluble in water, the solubility in water at 20°C is [0003] 28.2g / dL, high chemical stability in acidic solution, and long-term rigorous pharmacological, toxicological, physiological, physical and chemical tests have proved that sucralose is safe for humans. Because of its pure sweetness, it is very similar to the natural product sucrose, which is 600 times sweeter than sucrose, and has no unpleasant aftertaste brought by other sweeteners; it is not absorbed by the human body, does not produce heat, and does not interact with insulin when metabolized. It can be eaten by diabetics, obese patients and the elderly; it will not cause caries and is helpful for dental ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H13/06C07H1/00
Inventor 王式跃
Owner ZHEJIANG HAISEN PHARMACY CO LTD
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