Method for preparing isosteviol through catalytic hydrolysis of stevioside by chlorinated aromatic sulfonic resin

A technology of chloroarylsulfonic acid and steveside, which is applied in the preparation of carboxylates, organic compounds, organic chemistry, etc., can solve the problems of polluting the environment, corroding equipment, high requirements for enzyme selection, and high cost. achieve the effect of speeding up the reaction

Active Publication Date: 2015-08-12
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Enzyme-catalyzed hydrolysis has high requirements for the selection of enzymes, and the cost is relatively high; the products of inorganic acid-catalyzed hydrolysis are generally a mixture of steviol and isosteviol[1], and are likely to cause environmental pollution and corrosion of equipment

Method used

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  • Method for preparing isosteviol through catalytic hydrolysis of stevioside by chlorinated aromatic sulfonic resin
  • Method for preparing isosteviol through catalytic hydrolysis of stevioside by chlorinated aromatic sulfonic resin
  • Method for preparing isosteviol through catalytic hydrolysis of stevioside by chlorinated aromatic sulfonic resin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] With 540mL concentration of 100g / L of stevioside solution (the purity of stevioside is 95%, containing RA4.0%, RC0.2%, others are all compounds with steviol glycoside characteristic ultraviolet absorption, solvent is 5% DMF aqueous solution) was preheated at 90°C for 0.5 hour; then the preheated solution was passed through a packed column equipped with a chloroarenesulfonic acid type ion-exchange macroporous resin catalyst at a flow rate of 5mL / h, and the volume of the packed column was 50mL , the resin exchange capacity is 4.7mmol / g, and the jacket of the packed column is heated with external circulating water so as to control the reaction temperature at 90°C. The effluent then enters a storage tank with a temperature of 5° C., and 5 mL of 5% DMF aqueous solution is placed in the storage tank. The product isosteviol is precipitated in a low-temperature storage tank. The effluent is preheated at 90° C. The flow rate of h is circulated into the catalyst column, and after...

Embodiment 2

[0040] 500mL of steviol glycoside solution with a concentration of 150g / L (the purity of stevioside is 80%, containing 15% of RA, 2% of RC, and the others are all compounds with steviol glycoside characteristic ultraviolet absorption, and the solvent is water) at 80°C Preheating for 0.5 hour; then this preheating solution is passed through a packed column equipped with a chlorinated arylsulfonic acid type ion exchange macroporous resin catalyst at a flow rate of 2mL / h, the volume of the packed column is 50mL, and the resin exchange capacity is 4.96mmol / g, the packed column jacket is heated with external circulating water so that its reaction temperature is controlled at 80°C; the effluent then enters a storage tank with a temperature of 25°C, and 5mL of water is placed in the storage tank, and the product isosteviol is stored in a low-temperature storage tank Precipitated, the effluent was preheated at 80°C for 0.5 hours and then circulated into the catalyst column. After 10 h...

Embodiment 3

[0042] 700mL concentration of 50g / L of stevioside solution (the purity of stevioside is 98%, containing 1.5% of RA, and others are all compounds with steviol glycoside characteristic ultraviolet absorption, and the solvent is 10% DMF aqueous solution) in Preheat at 95°C for 0.5 hour; then pass this preheated solution through a packed column equipped with a chloroarenesulfonic acid type ion-exchange macroporous resin catalyst at a flow rate of 2mL / h, the volume of the packed column is 50mL, and the resin exchange capacity is 4.96 mmol / g, the packed column jacket is heated with external circulating water so that its reaction temperature is controlled at 95°C; the effluent enters a storage tank with a temperature of 0°C, and 5mL of 10% DMF aqueous solution is placed in the storage tank, and the product isosteviol Precipitated in a low-temperature storage tank, the effluent was preheated at 95°C for 0.5 hours and then circulated into the catalyst column. After 6 hours of reaction, ...

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Abstract

The invention provides a method for preparing isosteviol through catalytic hydrolysis of stevioside by chlorinated aromatic sulfonic resin, which belongs to the technical field of organic synthesis of organic compounds. According to the invention, a chlorinated aromatic sulfonic ion exchange macroporous resin packed bed is used for continuous catalytic hydrolysis of stevioside so as to prepare isosteviol, and a step-by-step cooling and circulation manner is adopted to remove products in time and to accelerate reaction. The method provided by the invention has the advantages of high yield, simple operation, environment friendliness, good stability performance of the catalyst, etc. The strong chlorinated aromatic sulfonic ion exchange macroporous resin can maintain 97% of catalytic activity after repeatedly used 10 times. Yield of isosteviol can reach more than 95%, and purity of isosteviol is more than 98% after simple recrystallization.

Description

【Technical field】 [0001] The invention belongs to the technical field of chemical synthesis of organic compounds. More specifically, the invention relates to the continuous catalytic hydrolysis of steveside with a packed bed of chlorinated arylsulfonic acid type resin, and adopts a step-by-step cooling cycle to remove products in time to speed up the reaction To prepare the method of isosteviol. 【Background technique】 [0002] Steviaside (St) is derived from stevia extract, and high-purity steviaside is a by-product of rebaudioside A (RA) refined from stevia extract. Stevia rebaudiana extract not only contains a large amount of stevia glycosides (40%-80%, the products of each company are different), but also contains rebaudioside A (RA) and rebaudioside C (RC). Isosteviol has anti-hypertensive, hypoglycemic, and tumor-inhibiting activities, as well as anti-inflammation, myocardial protection, and insulin-sensitizing effects. The preparation of isosteviol mainly has two way...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C62/24C07C51/373
Inventor 夏咏梅刘广智张宗英方圆孙志东
Owner JIANGNAN UNIV
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