Phenylboronic Acid Functionalized Adsorbents for Selective and Reversible Adsorption of Lactulose from Syrup Mixtures

J Agric Food Chem. 2018 Sep 5;66(35):9269-9281. doi: 10.1021/acs.jafc.8b02152. Epub 2018 Aug 27.

Abstract

Boronate affinity materials have been widely used for enrichment of cis-diol molecules. In this work, phenylboronic acid functionalized adsorbents were prepared via a simple and efficient procedure grafting phenylboronic acid groups onto amino macroporous resins. Elemental analysis has confirmed the successful functionalization of AR-1M and AR-2M with approximately 2.17% and 0.73% weight percentage of boron. Comparatively, AR-1M possessed higher lactulose adsorption capacity ( qe-Lu, 84.78 ± 0.95 mg/g dry resin) under neutral conditions (pH = 7), while the introduced glutaraldehyde spacer arms on AR-2M resulted in excellent adsorption selectivity (α ≈ 23), high adsorption efficiency (π ≈ 22%), and fast adsorption/desorption rate. The purity of lactulose (PuDLu) through pH-driven adsorption (pH 7-8) and desorption (pH 1.5) can be effectively improved depending on the ratio of lactulose to lactose. When lactulose/lactose ≥ 1:1, PuDLu ≈ 95% was achieved. No significant drop in qe-Lu (>90%) was observed after ten-consecutive repeats. Results demonstrated that the newly developed method may achieve satisfactory performance in lactulose purification.

Keywords: Lactulose; adsorption selectivity; pH-responsive; phenylboronic acid functionalized adsorbent; recyclability.

MeSH terms

  • Adsorption
  • Boronic Acids / chemistry*
  • Hydrogen-Ion Concentration
  • Kinetics
  • Lactose / chemistry
  • Lactulose / chemistry*

Substances

  • Boronic Acids
  • Lactulose
  • Lactose
  • benzeneboronic acid