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Sequestration of Phenols from Water into Poly(α-olefins) Facilitated by Hydrogen Bonding Polyisobutylene Additives
https://orcid.org/0000-0002-9609-806X
https://orcid.org/0000-0002-1657-0003
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.
Removal of phenolic compounds from water by liquid−liquid extraction using poly(α-olefin)-based solvent systems with polyisobutylene-derived additives is discussed.
Sequestration of Phenols from Water into Poly(α-olefins) Facilitated by Hydrogen Bonding Polyisobutylene Additives
https://orcid.org/0000-0002-9609-806X
https://orcid.org/0000-0002-1657-0003
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.
Removal of phenolic compounds from water by liquid−liquid extraction using poly(α-olefin)-based solvent systems with polyisobutylene-derived additives is discussed.
Sequestration of Phenols from Water into Poly(α-olefins) Facilitated by Hydrogen Bonding Polyisobutylene Additives
https://orcid.org/0000-0002-9609-806X
https://orcid.org/0000-0002-1657-0003
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.
Removal of phenolic compounds from water by liquid−liquid extraction using poly(α-olefin)-based solvent systems with polyisobutylene-derived additives is discussed.
Sequestration of Phenols from Water into Poly(α-olefins) Facilitated by Hydrogen Bonding Polyisobutylene Additives
Rosenfeld, Neil (author) / Quinn, Ethan (author) / Malinski, Thomas J. (author) / Bergbreiter, David E. (author)
ACS ES&T Water ; 2 ; 1391-1401
2022-08-12
Article (Journal)
Electronic Resource
English
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