Solvent extraction and extraction–voltammetric determination of phenols using room temperature ionic liquid

The phenolic compounds phenol, 4-nitrophenol, 2,4-dinitrophenol, 2,6-dinitrophenol, 1-naphthol, 2-naphthol, and 4-chlorophenol are extracted nearly quantitatively from aqueous solution into the room temperature ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate (BMImPF6) in molecular form at pH<pKa. Picric acid is extracted efficiently in anionic form. Recovery of pyrocatechol and resorcinol is much lower. The effect of pH, phenol concentration, and volume ratio of aqueous and organic phases were studied. Ionic liquid BMImPF6 is shown to be suitable for extraction–voltammetric determination of phenols without back-extraction or addition of support electrolyte. The electrochemical window of BMImPF6 at various electrodes was determined, and voltammetric oxidation of phenols and reduction of nitrophenols in BMImPF6 was studied.

[1]  I. Pletnev,et al.  Solvent extraction of amino acids into a room temperature ionic liquid with dicyclohexano-18-crown-6 , 2004, Analytical and bioanalytical chemistry.

[2]  K. R. Seddon Room‐Temperature Ionic Liquids: Neoteric Solvents for Clean Catalysis , 1997 .

[3]  Po-Yu Chen,et al.  Electrochemistry of Cd(II) in the basic 1-ethyl-3-methylimidazolium chloride/tetrafluoroborate room temperature molten salt , 2000 .

[4]  H. Olivier-Bourbigou,et al.  Ionic liquids: perspectives for organic and catalytic reactions , 2002 .

[5]  I. Pearl,et al.  Anodic reactions of simple phenolic compounds. , 1964 .

[6]  K. Furton,et al.  Organic salts, liquid at room temperature, as mobile phases in liquid chromatography , 1986 .

[7]  Richard G. Compton,et al.  Laser activated voltammetry: application to the determination of phenol in aqueous solution at a glassy carbon electrode , 2000 .

[8]  C. Mello,et al.  Simultaneous determination of phenol isomers in binary mixtures by differential pulse voltammetry using carbon fibre electrode and neural network with pruning as a multivariate calibration tool , 2000 .

[9]  J. Fuller,et al.  Structure of 1-ethyl-3-methylimidazolium hexafluorophosphate : model for room temperature molten salts , 1994 .

[10]  C. Barnes,et al.  Solvent extraction of strontium nitrate by a crown ether using room-temperature ionic liquids† , 1999 .

[11]  E. Emerson THE CONDENSATION OF AMINOANTIPYRINE. II. A NEW COLOR TEST FOR PHENOLIC COMPOUNDS , 1943 .

[12]  D. Armstrong,et al.  Examination of ionic liquids and their interaction with molecules, when used as stationary phases in gas chromatography. , 1999, Analytical chemistry.

[13]  J. A. Laszlo,et al.  Direct electrochemical reduction of hemin in imidazolium-based ionic liquids , 2002 .

[14]  O. Shpigun,et al.  Determination of gallic acid with 4-nitrobenzenediazonium tetrafluoroborate by diffuse reflectance spectrometry on polyurethane foam , 2002 .

[15]  W. Maccrehan,et al.  Determination of phenols in petroleum crude oils using liquid chromatography with electrochemical detection , 1987 .

[16]  Po-Yu Chen,et al.  Electrochemical study of copper in a basic 1-ethyl-3-methylimidazolium tetrafluoroborate room temperature molten salt , 1999 .

[17]  B. Dempsey,et al.  Ionisation constants of organic acids in aqueous solution , 1979 .

[18]  Tom Welton,et al.  Diels-Alder reactions in room-temperature ionic liquids , 1999 .

[19]  M. Roberts,et al.  High-performance liquid chromatographic determination of phenol, 4-nitrophenol, beta-naphthol and a number of their glucuronide and sulphate conjugates in organ perfusate. , 1996, Journal of chromatography. B, Biomedical applications.

[20]  D. Armstrong,et al.  Ionic liquids as matrixes for matrix-assisted laser desorption/ionization mass spectrometry. , 2001, Analytical chemistry.

[21]  Sandra Einloft,et al.  Enlarged electrochemical window in dialkyl-imidazolium cation based room-temperature air and water-stable molten salts , 1997 .

[22]  D. Armstrong,et al.  Solvent properties of the 1-butyl-3-methylimidazolium hexafluorophosphate ionic liquid , 2003, Analytical and bioanalytical chemistry.

[23]  Robin D. Rogers,et al.  Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation , 2001 .

[24]  Contribution of Substituent Groups to the Extractability of Phenols and Benzoic Acids , 1991 .

[25]  G. E. Penketh The oxidation potentials of phenolic and amino antioxidants , 2007 .

[26]  Petr Zuman,et al.  Polarography in organic chemistry , 1968 .

[27]  K. R. Seddon,et al.  The phase behaviour of 1-alkyl-3-methylimidazolium tetrafluoroborates; ionic liquids and ionic liquid crystals , 1999 .

[28]  Robin D. Rogers,et al.  Room temperature ionic liquids as novel media for ‘clean’ liquid–liquid extraction , 1998 .

[29]  Jing-Fang Huang,et al.  NMR evidence of hydrogen bonding in 1-ethyl-3-methylimidazolium-tetrafluoroborate room temperature ionic liquid , 2001 .

[30]  E. Mohler,et al.  Determination of Phenolic-Type Compounds in Water and Industrial Waste Waters Comparison of Analytical Methods , 1957 .

[31]  D. Cui,et al.  Voltammetric determination of 4-nitrophenol at a sodium montmorillonite-anthraquinone chemically modified glassy carbon electrode. , 2001, Talanta.

[32]  M. Ondrechen,et al.  The Intrinsic Anodic Stability of Several Anions Comprising Solvent‐Free Ionic Liquids , 1996 .

[33]  M. Dietz,et al.  Ion-exchange as a mode of cation transfer into room-temperature ionic liquids containing crown ethers: implications for the 'greenness' of ionic liquids as diluents in liquid-liquid extraction. , 2001, Chemical communications.

[34]  F. Endres,et al.  Electrodeposition of stable and narrowly dispersed germanium nanoclusters from an ionic liquid. , 2002, Chemical communications.