Synthesis of Rigid Cyclodextrin-Containing Polymeric Resins for Adsorption

Abstract

Cyclodextrins (CDs) are a family of cyclic-oligosaccharides with usually 6-8 glucopyranose units. Because of their unique donut-shaped steric structure they are able to form inclusion complexes selectively with some guest molecules. CDs are in starch-like powder form and are soluble in water to certain extents. It is desirable to produce insoluble CD-containing particles for adsorption, liquid chromatography and other applications. This work presents a novel method of synthesizing CD-containing resins. Resins synthesized with this method possess high contents of CDs and some favorable physical properties. Adsorption isotherms for three small aromatic compounds, namely phenylalanine, tryptophan and aspartame, were obtained experimentally.

Characterization, molecular dynamics, and encapsulation ability of β-cyclodextrin polymers crosslinked by polyethylene glycol

“…Several properties of CD, including its stability to pH and heat, shear forces, and its solubility, can be modified depending on the type of crosslinking agent used during its polymerization (Crini, 2005;Crini et al, 1998;Crini & Morcellet, 2002). For example, waterinsoluble CD polymers (CDPs), which have gained much attention as encapsulating materials for removing organic pollutants from solvents (Cadars, Foray, Gadelle, Gerbaud, & Bardet, 2005;Gerbaud, Hediger, Gadelle, & Bardet, 2008;Gu, Tsai, & Tsao, 2006;Harada, Furue, & Nozakura, 1981;Kitaoka & Hayashi, 2002;Sreenivasan, 1996;Werner, Iannacone, & Amoo, 1996), are generally obtained by using bifunctional crosslinking agents. Epichlorohydrin has been the most extensively utilized bifunctional crosslinking agent in CDP production; it reacts with the hydroxyl groups of CD to form inter-and intramolecular mono-and diethers (Cadars, et al, 2005;Gerbaud, et al, 2008;Gu, et al, 2006;Harada, et al, 1981;Kitaoka & Hayashi, 2002;Sreenivasan, 1996;Werner, Iannacone, & Amoo, 1996).…”

“…For example, waterinsoluble CD polymers (CDPs), which have gained much attention as encapsulating materials for removing organic pollutants from solvents (Cadars, Foray, Gadelle, Gerbaud, & Bardet, 2005;Gerbaud, Hediger, Gadelle, & Bardet, 2008;Gu, Tsai, & Tsao, 2006;Harada, Furue, & Nozakura, 1981;Kitaoka & Hayashi, 2002;Sreenivasan, 1996;Werner, Iannacone, & Amoo, 1996), are generally obtained by using bifunctional crosslinking agents. Epichlorohydrin has been the most extensively utilized bifunctional crosslinking agent in CDP production; it reacts with the hydroxyl groups of CD to form inter-and intramolecular mono-and diethers (Cadars, et al, 2005;Gerbaud, et al, 2008;Gu, et al, 2006;Harada, et al, 1981;Kitaoka & Hayashi, 2002;Sreenivasan, 1996;Werner, Iannacone, & Amoo, 1996). However, a major drawback to its use is that epichlorohydrin produces poisonous and carcinogenic byproducts under the alkaline conditions required to polymerize CD (Wester, van der Heijden, Bisschop, & van Esch, 1985).…”

Synthesis of Reusable Cyclodextrin Polymers for Removal of Naphthol and Naphthylamine from Water

“…Using small polyfunctional molecule as the crosslinking agent, such as epichlorohydrin, would result in a weak mechanical strength of the polymer with a gel-like appearance. To synthesize CD polymers with permanent microporosity and high CD content, a multifunctional crosslinking agent with small molecular size and strong structure is needed (Alsbaiee et al 2016;Gu et al 2006;Mhlanga et al 2007). As a new cross-linking agent, rigid tetra uoroterephthalonitrile is proposed by Alsbaiee et al (Alsbaiee et al 2016) and Ling et al (Ling et al 2017).…”

A novel β-cyclodextrin polymer modified by sulfonate groups

“…As has been reported, b-CD polymers can effectively adsorb organic molecules and heavy metals in water [8][9][10][11][12][13][14][15][16][17][18][19][20]. b-CD polymers modified by carboxyl/carboxylate groups (-COOH/-COO -) have been found to be more efficient in adsorption toward some heavy metals, basic dyes and aromatic amines [21][22][23][24][25][26][27][28][29][30].…”