The use of β-cyclodextrins to enhance the aqueous solubility of trichloroethylene and perchloroethylene and their removal from soil organic matter: Effect of substituents

Abstract

This paper describes a systematic study for the evaluation of different substituted β-cyclodextrins (β-CDs), as agents for the enhancement of the aqueous solubility of two major organic pollutants, trichloroethylene (TCE) and perchloroethylene (PCE). The aqueous solubility enhancement occurs through the formation of host–guest inclusion complexes between the CD molecule (host) and the polychloroethylene (guest) and is driven primarily by hydrophobic forces. The CDs evaluated are: methyl-β-CD (Mβ-CD), hydroxypropyl-β-CD (HPβ-CD), carboxymethyl-β-CD (CMβ-CD1, CMβ-CD2), and sulfated-β-CD (Sβ-CD1, Sβ-CD2); the degree of substitution was also varied. Using a 5% (w/v) aqueous CD solution, solubility enhancement factors (St/So) up to 5.5 and 14 were determined for TCE and PCE, respectively. Binding constants (K11) for TCE with the substituted CDs were evaluated using an 1H NMR technique; these were found to range from 3 to 120 M–1. It was shown that solubility enhancement, as well as the binding constant, is dependent on the type and degree of substitution of the β-CD molecule; the determining factors are discussed. The CDs are also capable of effective removal of PCE and TCE retained by soil organic matter. Thus, a suitably substituted β-CD may be a valuable additive in pump-and-treat protocols for site remediation of polychlorinated organics. Key words: Cyclodextrin, trichloroethylene, perchloroethylene, solubility enhancement, binding constant, soil and water remediation.