Generation of superoxide ion in pyridinium, morpholinium, ammonium, and sulfonium-based ionic liquids and the application in the destruction of toxic chlorinated phenols

Maan Hayyan, Farouq S. Mjalli, Mohd Ali Hashim, Inas M. Alnashef

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21 Citations (Scopus)

Abstract

Generation of superoxide ion (O 2 ̇-) was carried out in four ionic liquids (ILs) having the same anion, bis(trifluoromethylsulfonyl)imide [N(Tf) 2] -, and different cations, N-hexylpyridinium [HPy] +, N-methoxyethyl-N- methylmorpholinium [MO1,1O2] +, N-ethyl-N,N-dimethyl-2- methoxyethylammonium [N112,1O2] +, and triethylsulfonium [S222] +. Cyclic voltammetry (CV) and chronoamperometry (CA) electrochemical techniques were used in this investigation. It was found that O 2 ̇- is not stable in the [HPy] +-based IL. On the other hand, CV showed that the electrochemically generated O 2 ̇- is stable in [MO1,1O2] +-, [N112,1O2] +-, and [S222] +-based ILs for the time duration of the experiment. The long-term stability of the generated O 2 ̇- was then investigated by dissolving potassium superoxide (KO 2) in dimethyl sulfoxide (DMSO) in the presence of the corresponding IL. It was found that ILs containing [MO1,1O2] + and [N112,1O2] + offer a promising long-term stability of O 2 ̇- for various reactions to be used for several applications. However, it was found that after 2 h, about 92.5% of the generated O 2 ̇- in [S222] + based IL was consumed. The diffusion coefficient and solubility of O 2 in the studied ILs were then determined using CV and CA techniques simultaneously. It was found that diffusion coefficients and CA steady-state currents increase with temperature increases, while the solubility of O 2 decreased. To our best knowledge, this is the first time that morpholinium and sulfoniumbased ILs were utilized as media for chemical and electrochemical generation of O 2 ̇-. Additionally, the chemically generated O 2 ̇-, by dissolving KO 2, was then used for the destruction of 2,4-dichlorophenol (DCP) in [MO1,1O2][N(Tf) 2] under ambient conditions. The destruction percentage was higher than 98%. This work represents a novel application of the chemically generated O 2 ̇- for the destruction of toxic chlorinated phenols in ILs media.

Original languageEnglish
Pages (from-to)10546-10556
Number of pages11
JournalIndustrial and Engineering Chemistry Research
Volume51
Issue number32
DOIs
Publication statusPublished - Aug 15 2012

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Ionic Liquids
Poisons
Phenols
Ammonium Compounds
Ionic liquids
Superoxides
Ions
Chronoamperometry
Cyclic voltammetry
Solubility
Imides
Dimethyl sulfoxide
Dimethyl Sulfoxide
Anions
Potassium
Cations
Negative ions
Positive ions

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Chemistry(all)
  • Industrial and Manufacturing Engineering

Cite this

@article{2cbc54639c964210908a945d82cbd1b4,
title = "Generation of superoxide ion in pyridinium, morpholinium, ammonium, and sulfonium-based ionic liquids and the application in the destruction of toxic chlorinated phenols",
abstract = "Generation of superoxide ion (O 2 ̇-) was carried out in four ionic liquids (ILs) having the same anion, bis(trifluoromethylsulfonyl)imide [N(Tf) 2] -, and different cations, N-hexylpyridinium [HPy] +, N-methoxyethyl-N- methylmorpholinium [MO1,1O2] +, N-ethyl-N,N-dimethyl-2- methoxyethylammonium [N112,1O2] +, and triethylsulfonium [S222] +. Cyclic voltammetry (CV) and chronoamperometry (CA) electrochemical techniques were used in this investigation. It was found that O 2 ̇- is not stable in the [HPy] +-based IL. On the other hand, CV showed that the electrochemically generated O 2 ̇- is stable in [MO1,1O2] +-, [N112,1O2] +-, and [S222] +-based ILs for the time duration of the experiment. The long-term stability of the generated O 2 ̇- was then investigated by dissolving potassium superoxide (KO 2) in dimethyl sulfoxide (DMSO) in the presence of the corresponding IL. It was found that ILs containing [MO1,1O2] + and [N112,1O2] + offer a promising long-term stability of O 2 ̇- for various reactions to be used for several applications. However, it was found that after 2 h, about 92.5{\%} of the generated O 2 ̇- in [S222] + based IL was consumed. The diffusion coefficient and solubility of O 2 in the studied ILs were then determined using CV and CA techniques simultaneously. It was found that diffusion coefficients and CA steady-state currents increase with temperature increases, while the solubility of O 2 decreased. To our best knowledge, this is the first time that morpholinium and sulfoniumbased ILs were utilized as media for chemical and electrochemical generation of O 2 ̇-. Additionally, the chemically generated O 2 ̇-, by dissolving KO 2, was then used for the destruction of 2,4-dichlorophenol (DCP) in [MO1,1O2][N(Tf) 2] under ambient conditions. The destruction percentage was higher than 98{\%}. This work represents a novel application of the chemically generated O 2 ̇- for the destruction of toxic chlorinated phenols in ILs media.",
author = "Maan Hayyan and Mjalli, {Farouq S.} and Hashim, {Mohd Ali} and Alnashef, {Inas M.}",
year = "2012",
month = "8",
day = "15",
doi = "10.1021/ie3006879",
language = "English",
volume = "51",
pages = "10546--10556",
journal = "Industrial & Engineering Chemistry Product Research and Development",
issn = "0888-5885",
publisher = "American Chemical Society",
number = "32",

}

TY - JOUR

T1 - Generation of superoxide ion in pyridinium, morpholinium, ammonium, and sulfonium-based ionic liquids and the application in the destruction of toxic chlorinated phenols

AU - Hayyan, Maan

AU - Mjalli, Farouq S.

AU - Hashim, Mohd Ali

AU - Alnashef, Inas M.

PY - 2012/8/15

Y1 - 2012/8/15

N2 - Generation of superoxide ion (O 2 ̇-) was carried out in four ionic liquids (ILs) having the same anion, bis(trifluoromethylsulfonyl)imide [N(Tf) 2] -, and different cations, N-hexylpyridinium [HPy] +, N-methoxyethyl-N- methylmorpholinium [MO1,1O2] +, N-ethyl-N,N-dimethyl-2- methoxyethylammonium [N112,1O2] +, and triethylsulfonium [S222] +. Cyclic voltammetry (CV) and chronoamperometry (CA) electrochemical techniques were used in this investigation. It was found that O 2 ̇- is not stable in the [HPy] +-based IL. On the other hand, CV showed that the electrochemically generated O 2 ̇- is stable in [MO1,1O2] +-, [N112,1O2] +-, and [S222] +-based ILs for the time duration of the experiment. The long-term stability of the generated O 2 ̇- was then investigated by dissolving potassium superoxide (KO 2) in dimethyl sulfoxide (DMSO) in the presence of the corresponding IL. It was found that ILs containing [MO1,1O2] + and [N112,1O2] + offer a promising long-term stability of O 2 ̇- for various reactions to be used for several applications. However, it was found that after 2 h, about 92.5% of the generated O 2 ̇- in [S222] + based IL was consumed. The diffusion coefficient and solubility of O 2 in the studied ILs were then determined using CV and CA techniques simultaneously. It was found that diffusion coefficients and CA steady-state currents increase with temperature increases, while the solubility of O 2 decreased. To our best knowledge, this is the first time that morpholinium and sulfoniumbased ILs were utilized as media for chemical and electrochemical generation of O 2 ̇-. Additionally, the chemically generated O 2 ̇-, by dissolving KO 2, was then used for the destruction of 2,4-dichlorophenol (DCP) in [MO1,1O2][N(Tf) 2] under ambient conditions. The destruction percentage was higher than 98%. This work represents a novel application of the chemically generated O 2 ̇- for the destruction of toxic chlorinated phenols in ILs media.

AB - Generation of superoxide ion (O 2 ̇-) was carried out in four ionic liquids (ILs) having the same anion, bis(trifluoromethylsulfonyl)imide [N(Tf) 2] -, and different cations, N-hexylpyridinium [HPy] +, N-methoxyethyl-N- methylmorpholinium [MO1,1O2] +, N-ethyl-N,N-dimethyl-2- methoxyethylammonium [N112,1O2] +, and triethylsulfonium [S222] +. Cyclic voltammetry (CV) and chronoamperometry (CA) electrochemical techniques were used in this investigation. It was found that O 2 ̇- is not stable in the [HPy] +-based IL. On the other hand, CV showed that the electrochemically generated O 2 ̇- is stable in [MO1,1O2] +-, [N112,1O2] +-, and [S222] +-based ILs for the time duration of the experiment. The long-term stability of the generated O 2 ̇- was then investigated by dissolving potassium superoxide (KO 2) in dimethyl sulfoxide (DMSO) in the presence of the corresponding IL. It was found that ILs containing [MO1,1O2] + and [N112,1O2] + offer a promising long-term stability of O 2 ̇- for various reactions to be used for several applications. However, it was found that after 2 h, about 92.5% of the generated O 2 ̇- in [S222] + based IL was consumed. The diffusion coefficient and solubility of O 2 in the studied ILs were then determined using CV and CA techniques simultaneously. It was found that diffusion coefficients and CA steady-state currents increase with temperature increases, while the solubility of O 2 decreased. To our best knowledge, this is the first time that morpholinium and sulfoniumbased ILs were utilized as media for chemical and electrochemical generation of O 2 ̇-. Additionally, the chemically generated O 2 ̇-, by dissolving KO 2, was then used for the destruction of 2,4-dichlorophenol (DCP) in [MO1,1O2][N(Tf) 2] under ambient conditions. The destruction percentage was higher than 98%. This work represents a novel application of the chemically generated O 2 ̇- for the destruction of toxic chlorinated phenols in ILs media.

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