Phenyl boronic acid-based polymer carrier and applications in selective adsorption of saccharide-based substances

A phenylboronic acid-based, polymer technology, applied in the direction of solid adsorbent liquid separation, application, sugar production, etc., can solve the problems of potential safety hazards, low recovery rate, large consumption, etc., and achieve selective adsorption and rapid adsorption Effect

Active Publication Date: 2019-08-30
苏州福赛思生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Aiming at problems such as low recovery rate, high consumption of organic reagents, high cost, long time and potential safety hazards in the existing high-purity lactulose separation and purification process, the present invention utilizes saccharides containing ortho-cis-hydroxyl structures (fructose, Lactulose, etc.) and boric acid groups can undergo complexation under specific circumstances (pH>pKa), and the strength and priority of complexation forces between different sugars and boric acid groups are different. First, benzene Boronic acid-based functional monomers are used as raw materials to prepare phenylboronic acid-based polymer carriers through molecular self-assembly, intermolecular and / intramolecular copolymerization reactions, etc., and then use the unique properties of the phenylboronic acid groups loaded on the carrier to achieve lactulose, Selective adsorption and reversible cyclic adsorption of fructose and other sugars containing ortho-cis-hydroxyl structures to prepare high-purity target substances and realize the recycling of carriers at the same time

Method used

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  • Phenyl boronic acid-based polymer carrier and applications in selective adsorption of saccharide-based substances
  • Phenyl boronic acid-based polymer carrier and applications in selective adsorption of saccharide-based substances
  • Phenyl boronic acid-based polymer carrier and applications in selective adsorption of saccharide-based substances

Examples

Experimental program
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Effect test

Embodiment 1

[0060] Embodiment 1: Preparation of phenylboronic acid-based polymer carrier

[0061] Dissolve 1 mol of phenylboronic acid-based monomer AAPBA and 10 mol of cross-linking agent EGDMA into 1000 mL of DMSO, shake and mix evenly, and after standing in the dark for 1 hour, add 5 g of initiator azobisisobutyronitrile previously dissolved in 10 mL of DMSO, After oscillating evenly, ultrasonic degassing was performed for 30 minutes, and then nitrogen gas was continuously introduced for 30 minutes. After vacuum sealing, it was placed in a water bath at 60°C for 12 hours.

[0062] The block polymer obtained is ground, pulverized, sieved to obtain 120 mesh and 100 mesh size particles, the above particles are wrapped with filter paper, placed in a Soxhlet extractor, add 20% acetic acid: 80% methanol (v / v) extracting solution at 80°C for 24h to remove the porogen and solvent, then use 100% methanol to continue the extraction for 2h, and dry the obtained polymer particles at 60°C for 24h ...

Embodiment 2

[0064] Embodiment 2: Preparation of phenylboronic acid-based polymer carrier

[0065] Shake and mix 1mol of AAPBA with 2000mL of DMSO evenly, and shake in the dark for 12 hours to make the AAPBA evenly dispersed, then add 5mol of EGDMA, shake evenly and keep it in the dark for 2 hours, then add the initiator azodiisocyanate dissolved in 20mL of DMSO in advance Butyronitrile 10g, after shaking evenly, ultrasonic degassing for 10min, then continuously blowing in nitrogen for 15min, after vacuum sealing, place in 70°C water bath for 8h.

[0066] The block polymer obtained is ground, pulverized, sieved to obtain 120 mesh and 100 mesh size particles, the above particles are wrapped with filter paper, placed in a Soxhlet extractor, add 20% acetic acid: 80% methanol (v / v) of the extract was extracted at 90°C for 48h, the porogen DMSO was removed, and then 100% methanol was used to continue the extraction for 10h, and then the obtained polymer particles were dried under reduced press...

Embodiment 3

[0068] Embodiment 3: Batch type separation and purification of lactulose

[0069] Formulate a 5:25 mg / mL solution of lactulose and lactose at a ratio of 1:5, and then add 25 g of the 100-mesh phenylboronic acid-based polymer carrier prepared in Example 1 to the above 1L lactulose-lactose solution , at pH 7.0, oscillating and adsorbing at 25°C for 30min, and filtering and separating to obtain the adsorbed phenylboronic acid-based polymer carrier, and then adding the adsorbed carrier to 100mL deionized deionized water (pH ~ 5.8), at 25°C, Desorb for 15 minutes under the condition of 150r / min, and take samples to measure the adsorption capacity and the purity of the desorbed solution. The final detection of the phenylboronic acid-based polymer carrier adsorbed lactulose load is 79mg / g dry basis carrier, while the adsorption capacity of lactose is only 1.5mg / g dry basis carrier, the desorption rate is 90%, and the HPLC collection of desorption liquid is as follows: image 3 As sh...

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Abstract

The invention discloses synthesis of a phenyl boronic acid-based polymer carrier, and a method for selectively adsorbing and separating a saccharide-based substance having an ortho-cis hydroxy structure. According to the present invention, a strong surface hydrophobicity polymer carrier with a phenyl boronic acid group as the only functional group is prepared, the target saccharide-based substancehaving an ortho-cis hydroxy structure is efficiently and selectively adsorbed and separated from a saccharide-based mixing solution by using the carrier as an adsorbent, and through adsorption-desorption, lactulose with a purity of 10% can be purified to more than 95%, the purity of lactulose in the final eluent can reach more than 99% when the initial purity of lactulose reaches 25%, and the recovery rate is nearly 100%; and the phenyl boronic acid-based polymer carrier has stable structure, can achieve long-time continuous recycling or multi-batch batchwise separation and purification, meets resource-saving and environment-friendly production requirements, and easily promotes the clean, efficient and environmentally friendly industrial production of high-purity lactulose and related saccharides.

Description

technical field [0001] The invention relates to the synthesis of a phenylboronic acid-based polymer carrier and a method for selectively adsorbing and separating sugar substances containing an ortho-cis hydroxyl structure, belonging to the technical field of carbohydrate separation and purification. In particular, it relates to the preparation of a phenylboronic acid-based polymer carrier capable of efficiently and selectively adsorbing and separating sugar substances containing an ortho-cis-hydroxyl structure. Background technique [0002] Lactulose (C 12 h 22 o 11 , 4- O -β- D -Galactopyranosyl- D -Fructose) is a class of disaccharides containing an ortho-cis hydroxyl structure (fructofuranosyl), which has the advantages of low calorie, high safety, good stability, and wide application. As a functional prebiotic with multiple functional properties, lactulose is in line with the new concept of healthy consumption of consumers. The preparation of lactulose in the indu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F222/14C08F220/58C08J9/28B01J20/26B01J20/28B01J20/30B01D15/02B01D15/34C13K13/00
CPCC08F222/1006C08J9/28B01J20/261B01J20/28083B01D15/02B01D15/34C13K13/005C13K13/007C08J2335/02C08F222/102C08F220/585
Inventor 杨瑞金汪明明
Owner 苏州福赛思生物科技有限公司
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