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Preparation method for phenylboronic group modified macroporous resin and application of phenylboronic group modified macroporous resin in separation of rebaudiodside A and stervioside

A technology of macroporous resin and phenylboronic acid, applied in chemical instruments and methods, ion exchange, and other chemical processes, can solve the problems of complex process, difficult single component separation, time-consuming, etc., and achieve simple process and good reproducibility Effect

Active Publication Date: 2014-10-15
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the poor adsorption selectivity of macroporous resins, and the similar structure and physical and chemical properties of various steviol glycosides, the macroporous resins have insufficient discrimination for various steviol glycosides, and it is difficult to achieve the separation of a single component
Among the various steviol glycosides, rebaudioside A has the highest sweetness and the taste is closest to sucrose. Other steviol glycosides, especially stevioside, have obvious after-bitterness. If they are not separated and purified, the quality of the product will be affected.
Recrystallization is currently a widely used method for the purification of rebaudioside A, but this method has the disadvantages of time-consuming, complicated process, and residual organic solvents.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The methacrylic acid-divinylbenzene macroporous copolymer with a carboxylic acid group content of 4.7mmol / g is used as the raw material resin, and the resin is filtered out after standing and swelling in methanol for 24h at 25°C; the 1-(3 -Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and N-hydroxysuccinimide are formulated into 50mmol / L activated Reagent solution. Mix the activation reagent solution with the raw resin at a ratio of 20mL / g, react at 40°C for 2h, filter out the resin, and set aside; mix 20mmol / L 3-aminophenylboronic acid solution with the activated resin at a ratio of 20mL / g , reacted at 60° C. for 24 hours; after the reaction, filtered and washed with acetone and deionized water successively to obtain a phenylboronic acid group-modified macroporous resin. The content of phenylboronic acid groups in the macroporous resin modified by phenylboronic acid groups is about 310 μmol / g.

Embodiment 2

[0029] Acrylic acid-divinylbenzene macroporous copolymer with a carboxylic acid group content of 9.5mmol / g is used as the raw material resin, and the resin is filtered out after standing and swelling in ethanol for 24 hours at 25°C; Methylaminopropyl)-3-ethylcarbodiimide hydrochloride and N-hydroxysuccinimide are formulated into 100mmol / L activation reagent solution according to the ratio of the amount of substances of 1:2, with ethanol as solvent . Mix the activation reagent solution with the raw resin at a ratio of 10mL / g, react at 40°C for 2h, filter out the resin, and set aside; mix 40mmol / L 3-aminophenylboronic acid solution with the activated resin at a ratio of 5mL / g , reacted at 50° C. for 24 hours; after the reaction, filtered and washed with acetone and deionized water successively to obtain a phenylboronic acid group-modified macroporous resin. The content of phenylboronic acid group in the macroporous resin modified by phenylboronic acid group is about 140 μmol / g....

Embodiment 3

[0033] Acrylic acid-divinylbenzene macroporous copolymer with a carboxylic acid group content of 12mmol / g is used as the raw material resin, and the resin is filtered out after standing and swelling in methanol for 24h at 25°C; the 1-(3-dimethyl Aminopropyl)-3-ethylcarbodiimide hydrochloride and N-hydroxysuccinimide were formulated into an activating reagent solution of 80 mmol / L with methanol as a solvent in a substance ratio of 1:2. Mix the activation reagent solution with the raw resin at a ratio of 15mL / g, react at 30°C for 2h, filter out the resin, and set aside; mix 100mmol / L 3-aminophenylboronic acid solution with the activated resin at a ratio of 3mL / g , and react at 60° C. for 12 hours; after the reaction, filter and wash with acetone and deionized water in turn to obtain a phenylboronic acid group-modified macroporous resin. The content of phenylboronic acid groups in the macroporous resin modified by phenylboronic acid groups is about 230 μmol / g.

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Abstract

The invention discloses a preparation method for a phenylboronic group modified macroporous resin applicable to separation of rebaudiodside A and stervioside. The method comprises the following main steps: (1) pretreatment of a resin: a step of putting a carboxyl resin in an organic solvent for standing and swelling; (2) activation of the resin: a step of adding activation reagents consisting of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and N-hydroxylsuccimide and carrying out activation; (3) ligand coupling: a step of adding a 3-aminophenylboric acid solution and carrying out a reaction at a constant temperature for 6 to 24 h; and (4) post-treatment of the modified resin: a step of carrying out filtering after completion of the reaction and successively carrying out washing with acetone and deionized water so as to obtain the phenylboronic group modified macroporous resin. The invention has the following beneficial effects: a chromatographic column is filled with the prepared phenylboronic group modified macroporous resin; and the purity of separated rebaudiodside A is more than 90%, and the recovery rate of rebaudiodside A is more than 70%.

Description

technical field [0001] The invention relates to a preparation method and application of a macroporous resin, in particular to a preparation method of a phenylboronic acid group-modified macroporous resin and its application in the separation of rebaudioside A and stevioside. Background technique [0002] Macroporous resin is a kind of adsorption and separation material of polymer substrate, which is prepared by polymerizing monomer, crosslinking agent, initiator, porogen and other auxiliary agents through polymerization reaction. Macroporous resin has the characteristics of stable physical and chemical properties, high mechanical strength, strong anti-pollution ability, easy regeneration, mild desorption conditions, etc. It can be used in aqueous solution and non-aqueous solution, and has a long service life. It is suitable for forming a closed circuit and saving costs. In recent years, macroporous resins have been widely used in the extraction, separation, purification and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F220/06C08F212/36C08F8/42C08F8/32C08F8/30B01J20/26B01D15/08
Inventor 杨瑞金叶发银华霄赵伟张文斌唐乐乐
Owner JIANGNAN UNIV
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