Effects of multiple weak interactions on the binding of phenolic compounds by polymeric adsorbents

Abstract

To investigate the effects of multiple weak interactions on the binding of phenolic compounds by polymeric adsorbents, macroporous polystyrene (PS) resin and PS-based adsorbents with different hydrogen-bond acceptor atoms (PSÀ ÀCH 2 (À ÀOCH 2 CH 2 ) n À ÀOCH 3 , n ¼ 0, 1, 2, and 3, denoted as PS-EG 0 , PS-EG 1 , PS-EG 2 , and PS-EG 3 ) were prepared. The phenol adsorption strength order on these adsorbents was PS/PS-EG 0 < PS-EG 1 < PS-EG 2 < PS-EG 3 , indicating that the adsorption on PS and PS-EG 0 was driven by hydrophobic and p-p interactions, and the adsorption on PS-EG 1 , PS-EG 2 , and PS-EG 3 was driven by a hydrogen bond in addition to hydrophobic and p-p interactions. PS-EG 2 may adsorb a second phenol molecule on each binding site and PS-EG 3 may adsorb second and third ones. The adsorption strength of resorcinol increased in the order of PS, PS-EG 1 , and PS-EG 2 , indicating that the adsorption was driven by 0, 1, and 2 hydrogen bonds in addition to hydrophobic and p-p interactions. Similarly, the adsorption of phloroglucinol on PS, PS-EG 1 , PS-EG 2 , and PS-EG 3 was driven by 0, 1, 2, and 3 hydrogen bonds in addition to hydrophobic and p-p interactions because the adsorption strength increased in this order.

Preparation and characterization of polar polymeric adsorbents with high surface area for the removal of phenol from water

“…It is commonly known that adsorption capacity of adsorbent from aqueous solution is dominated by many factors and the adsorbate-adsorbent interaction will play an important role. The [12,13,48]. The adsorbing capacity of phenol for post-crosslinking derivatives is larger than precursors.…”

Enrichment and fractionation of major apple flavonoids, phenolic acids and dihydrochalcones using anion exchange resins

“…Furthermore, polyphenol binding may also be due to ionic interaction between the ion exchanger and the deprotonated phenolic compounds and attraction forces between the phenolic compounds. The latter may be attributed to pep and van der Waals interactions as well as dipoleedipole forces and hydrogen bridges amongst solute molecules and polyphenols bound onto the resin surface by interaction with the functional groups or the polymeric matrix, which contribute to the total binding of adsorbent and ion exchange resins (Cheng, Tang, & Yan, 2006) (Table 2). In addition, solvent molecules may form solvent clusters around solute molecules or functional groups of the exchanger resin.…”

“…Furthermore, intermolecular interactions among the phenolic compounds, i.e. pep interactions, van der Waals forces, dipoleedipole interactions and the formation of hydrogen bridges between solute molecules and compound molecules bound onto the resin surface (Table 2), a phenomenon commonly referred to as coadsorption (Cheng et al, 2006) are to be considered. At pH 7 ionic bonding of the deprotonated phenolics, especially of the hydroxycinnamic acids, with the quaternary ammonium functions of the ion exchanger are expected to play a predominant role in addition to van der Waals interactions with the polyacrylamide backbone.…”

Recovery, concentration and purification of phenolic compounds by adsorption: A review

“…Adsorption is also influenced by the adsorbate characteristics (Dargaville et al, 1996;Brune et al, 1999;Pan et al, 2005;Cheng et al, 2006;Navarro et al, 2008a;Geng et al, 2009). Adsorption from a multicomponent solution is a complex problem Kammerer et al, 2010a;Kammerer et al, 2010b;Silva et al, 2007).…”