While hydrocarbon solvents such as alkanes are ineffective
in extraction
of polar substances such as phenols from water, polymeric alkanes
such as poly(α-olefin)s (PAOs) when modified with phase-anchored
hydrogen bond-accepting polyisobutylene (PIB) additives can be designed
so that these hydrocarbon solvent systems efficiently extract many
phenols from water. Phenols such as bisphenol-A (BPA), 4-chlorophenol,
2,4-dichlorophenol, 2-naphthol, and alkyl- or aryl-substituted phenols
are sequestered from water with >95% efficiency. For example, using
a PIB oligomer with imidazole as a terminal group as an additive at
a concentration of 0.1 M in a PAO that is a hydrogenated trimer of
1-decene (PAO432), >99% of the BPA present in an aqueous
solution of deionized water containing 200 mg of BPA/L of water is
extracted into the PAO phase. With PIB-imidazole in PAO432 at 0.6 or 1.0 M, an array of other chlorinated, brominated, and
alkylated phenols, which were typically initially present between
200 and 500 mg/L water, were additionally extracted with >95% efficiency.
Using 0.3 M PIB-imidazole in PAO432, other bisphenols such
as phenolphthalein and fluorescein at concentrations of ca. 3 mg/L
in water could be reduced to concentrations of <20 or 2 μg/L,
respectively. While very polar phenols with methoxy, hydroxy, and
amino substituents are less efficiently extracted, most of these phenols
could ultimately be extracted and sequestered with >80% efficiency.
PAO432/PIB-imidazole phases that contain sequestered phenol
can be recycled by mixing the PAO phase with solid NaOH. This regenerates
the starting PAO432/PIB-imidazole mixture. Recycling of
these nonvolatile PAO solvent systems for at least five cycles is
described. Substituted imidazoles bound to PIB were also shown to
be similarly effective sequestering agents for phenols.