INNOVATIVE APPLICATIONS OF IONIC LIQUIDS AS “GREEN” ENGINEERING LIQUIDS

Over the past decade, ionic liquids (ILs) have become one of the fastest growing “green” media for chemists and engineers due to their superb physicochemical properties. The applications of these remarkable salts in reactions and extraction processes have been extensively investigated and reviewed. This review, however, highlights recent advances of ILs as versatile “green” engineering liquids in a variety of industrial applications including heat transfer fluids, azeotrope-breaking liquids, lubricants, electrolytes, liquid crystals, supported IL membranes, plasticizers, and more. This review is not intended to be comprehensive, but rather to discuss the potentials of ILs for diverse industrial applications.

[1]  K. Holmberg,et al.  Surfactants and Polymers in Aqueous Solution, 2nd ed. , 2003 .

[2]  J. Pernak,et al.  Synthesis and properties of chiral ammonium-based ionic liquids. , 2005, Chemistry.

[3]  大野 弘幸,et al.  Electrochemical aspects of ionic liquids , 2005 .

[4]  Makoto Ue,et al.  Application of Low-Viscosity Ionic Liquid to the Electrolyte of Double-Layer Capacitors , 2003 .

[5]  D. Armstrong,et al.  Ionic liquids as stationary phase solvents for methylated cyclodextrins in gas chromatography , 2001 .

[6]  G. Blomgren,et al.  Ionic Liquids for Lithium Ion and Related Batteries , 2002 .

[7]  J. Holbrey,et al.  Designing Ionic Liquids: Imidazolium Melts with Inert Carborane Anions , 2000 .

[8]  A. Abbott,et al.  Electropolishing of stainless steel in an ionic liquid , 2005 .

[9]  H. Ohno,et al.  Layered Ionic Liquids: Anisotropic Ion Conduction in New Self‐Organized Liquid‐Crystalline Materials , 2002 .

[10]  John W. Goodby,et al.  Handbook of liquid crystals , 1998 .

[11]  Feng Zhou,et al.  Functional Room-temperature Ionic Liquids as Lubricants for an Aluminum-on-Steel System , 2004 .

[12]  R. Sheldon,et al.  Biocatalytic transformations in ionic liquids. , 2003, Trends in biotechnology.

[13]  Jairton Dupont,et al.  Room temperature dialkylimidazolium ionic liquid-based fuel cells , 2003 .

[14]  A. Daugulis,et al.  Phosphonium ionic liquids for degradation of phenol in a two-phase partitioning bioreactor , 2005, Applied Microbiology and Biotechnology.

[15]  Yasuhiko Ito,et al.  Non-conventional electrolytes for electrochemical applications , 2000 .

[16]  Xingguo Chen,et al.  Rapid and sensitive determination of anthraquinones in Chinese herb using 1-butyl-3-methylimidazolium-based ionic liquid with beta-cyclodextrin as modifier in capillary zone electrophoresis. , 2004, Journal of chromatography. A.

[17]  Richard G Compton,et al.  Use of room temperature ionic liquids in gas sensor design. , 2004, Analytical chemistry.

[18]  Zhaojie Cui,et al.  Friction and wear behaviors of ionic liquid of alkylimidazolium hexafluorophosphates as lubricants for steel/steel contact , 2004 .

[19]  M. Heitz,et al.  Surfactants in Green Solvent Systems—Current and Future Research Directions , 2003 .

[20]  G. Habermehl,et al.  ReviewPure appl. Chem: Rinehart, K. L., et al. Marine natural products as sources of antiviral, antimicrobial, and antineoplastic Agents. 53, 795 (1981). (K. L. Rinehart, University of Illinois, Urbana, IL 61801, U.S.A.) , 1983 .

[21]  Hiroyuki Ohno,et al.  Electrochemical Aspects of Ionic Liquids: Ohno/Electrochemical Aspects of Ionic Liquids , 2005 .

[22]  Randall J. Bernot,et al.  Acute and chronic toxicity of imidazolium‐based ionic liquids on Daphnia magna , 2005, Environmental toxicology and chemistry.

[23]  J. Pernak,et al.  Ionic Liquids and Paper , 2005 .

[24]  Randall J. Bernot,et al.  Effects of ionic liquids on the survival, movement, and feeding behavior of the freshwater snail, Physa acuta , 2005, Environmental toxicology and chemistry.

[25]  S. Hayase,et al.  Quasi-solid dye sensitised solar cells filled with ionic liquid--increase in efficiencies by specific interaction between conductive polymers and gelators. , 2003, Chemical communications.

[26]  D. Armstrong,et al.  Ionic liquids in analytical chemistry. , 2006, Analytical chemistry.

[27]  P. Kubisa.  Application of ionic liquids as solvents for polymerization processes , 2004 .

[28]  B. Jönsson.  Surfactants and Polymers in Aqueous Solution , 1998 .

[29]  R. Barhdadi,et al.  Room-temperature ionic liquids as new solvents for organic electrosynthesis. The first examples of direct or nickel-catalysed electroreductive coupling involving organic halides. , 2003, Chemical communications.

[30]  Charles F. Kulpa,et al.  Toxicity and antimicrobial activity of imidazolium and pyridinium ionic liquids , 2005 .

[31]  G. Voth,et al.  IONIC LIQUIDS , 2004 .

[32]  G. Pez,et al.  Molten salt facilitated transport membranes. Part 1. Separation of oxygen from air at high temperatures , 1992 .

[33]  G. Wallace,et al.  Use of Ionic Liquids as Electrolytes in Electromechanical Actuator Systems Based on Inherently Conducting Polymers , 2003 .

[34]  A. Doherty,et al.  Electrosynthesis in room-temperature ionic liquids: benzaldehyde reduction , 2004 .

[35]  M. Watanabe,et al.  A novel Brønsted acid-base system as anhydrous proton conductors for fuel cell electrolytes , 2003 .

[36]  J. Crespo,et al.  Highly selective transport of organic compounds by using supported liquid membranes based on ionic liquids. , 2002, Angewandte Chemie.

[37]  K. R. Seddon.  Ionic Liquids for Clean Technology , 1997 .

[38]  Sam F. Y. Li,et al.  1,3-dialkylimidazolium-based room-temperature ionic liquids as background electrolyte and coating material in aqueous capillary electrophoresis. , 2003, Journal of chromatography. A.

[39]  Jing-fu Liu,et al.  Application of ionic liquids in analytical chemistry , 2005 .

[40]  V. Jouikov,et al.  Superoxide-stable ionic liquids: new and efficient media for electrosynthesis of functional siloxanes. , 2004, Chemical communications.

[41]  S. Volkov,et al.  Ionic Liquid Crystals as Universal Matrices (Solvents) , 2003 .

[42]  Peng Wang,et al.  High efficiency dye-sensitized nanocrystalline solar cells based on ionic liquid polymer gel electrolyte. , 2002, Chemical communications.

[43]  C. Plesse,et al.  Long-life air working conducting semi-IPN/ionic liquid based actuator , 2004 .

[44]  A. Robertson,et al.  Industrial preparation of phosphonium ionic liquids , 2003 .

[45]  Robin D. Rogers,et al.  Green industrial applications of ionic liquids , 2002 .

[46]  Lijun He,et al.  Effect of Ionic Liquids as Mobile Phase Additives on Retention of Catecholamines in Reversed-Phase High-Performance Liquid Chromatography , 2003 .

[47]  T. Welton,et al.  Chiral ionic liquids as stationary phases in gas chromatography. , 2004, Analytical chemistry.

[48]  G. Wallace,et al.  Electrochemical synthesis of polypyrrole in ionic liquids , 2004 .

[49]  Alan R. Kennedy,et al.  Ionic liquid crystals: hexafluorophosphate salts , 1998 .

[50]  Conventional Aspects of Unconventional Solvents: Room Temperature Ionic Liquids as Ion-Exchangers and Ionic Surfactants , 2003 .

[51]  R. G. Evans,et al.  Non-haloaluminate room-temperature ionic liquids in electrochemistry--a review. , 2004, Chemphyschem : a European journal of chemical physics and physical chemistry.

[52]  A. Stalcup,et al.  Ionic Liquids in Chromatography and Capillary Electrophoresis , 2004 .

[53]  M. Goto,et al.  Enzyme-facilitated enantioselective transport of (S)-ibuprofen through a supported liquid membrane based on ionic liquids. , 2003, Chemical communications.

[54]  U. Kragl,et al.  Enzyme catalysis in ionic liquids. , 2002, Current opinion in biotechnology.

[55]  K. Takagi,et al.  Electrochemical properties of novel ionic liquids for electric double layer capacitor applications , 2004 .

[56]  Maria Forsyth,et al.  Polymer-in-ionic-liquid electrolytes , 2002 .

[57]  Wolfgang Arlt,et al.  Separation of Azeotropic Mixtures Using Hyperbranched Polymers or Ionic Liquids , 2004 .

[58]  T. Jiang,et al.  Dynamically coating the capillary with 1-alkyl-3-methylimidazolium-based ionic liquids for separation of basic proteins by capillary electrophoresis , 2003 .

[59]  R. Kazlauskas,et al.  Biocatalysis in ionic liquids - advantages beyond green technology. , 2003, Current opinion in biotechnology.

[60]  Peng Wang,et al.  A New Ionic Liquid Electrolyte Enhances the Conversion Efficiency of Dye-Sensitized Solar Cells , 2003 .

[61]  B. Ondruschka,et al.  Biological effects of imidazolium ionic liquids with varying chain lengths in acute Vibrio fischeri and WST-1 cell viability assays. , 2004, Ecotoxicology and environmental safety.

[62]  Liu Xia,et al.  Ionic liquids as additives in high performance liquid chromatography: Analysis of amines and the interaction mechanism of ionic liquids , 2004 .

[63]  Robin D. Rogers,et al.  Ionic liquids are not always green: hydrolysis of 1-butyl-3-methylimidazolium hexafluorophosphate , 2003 .

[64]  M. Matsumoto,et al.  Selective separation of aromatic hydrocarbons through supported liquid membranes based on ionic liquids , 2005 .

[65]  J. Pernak,et al.  Ionic liquids in embalming and tissue preservation. Can traditional formalin-fixation be replaced safely? , 2003, Acta histochemica.

[66]  T. Landry,et al.  Acute Toxicity Profile of 1-Butyl-3-Methylimidazolium Chloride , 2005, Bulletin of environmental contamination and toxicology.

[67]  Ramana G. Reddy,et al.  Corrosion of steel in ionic liquids , 2003 .

[68]  Sam F. Y. Li,et al.  Electrophoresis of DNA in ionic liquid coated capillary. , 2003, The Analyst.

[69]  Nicholas Gathergood,et al.  Biodegradable ionic liquids: Part I. Concept, preliminary targets and evaluation , 2004 .

[70]  G. Wallace,et al.  Solid state actuators based on polypyrrole and polymer-in-ionic liquid electrolytes , 2003 .

[71]  Robin D. Rogers,et al.  Ionic liquids : industrial applications for green chemistry , 2002 .

[72]  Qunji Xue,et al.  Room temperature ionic liquid 1-ethyl-3-hexylimidazolium-bis(trifluoromethylsulfonyl)-imide as lubricant for steel–steel contact , 2004 .

[73]  B. Weyershausen,et al.  Industrial application of ionic liquids as performance additives , 2005 .

[74]  T. Nishida,et al.  Physical and electrochemical properties of 1-alkyl-3-methylimidazolium tetrafluoroborate for electrolyte , 2003 .

[75]  Takuzo Aida,et al.  Molecular Ordering of Organic Molten Salts Triggered by Single-Walled Carbon Nanotubes , 2003, Science.

[76]  Robin D. Rogers,et al.  Ionic Liquids IIIB: Fundamentals, Progress, Challenges, and Opportunities: Transformations and Processes , 2005 .

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

[78]  J. Fuller,et al.  Ionic liquid–polymer gel catalytic membrane , 1997 .

[79]  A. Lewandowski.  Electrochemical capacitors with polymer electrolytes based on ionic liquids , 2003 .

[80]  Peng Wang,et al.  Tribological Performance of Room-Temperature Ionic Liquids as Lubricant , 2002 .

[81]  J. Crespo,et al.  Studies on the selective transport of organic compounds by using ionic liquids as novel supported liquid membranes. , 2002, Chemistry.

[82]  Hiroshi Matsui,et al.  High performance dye-sensitized solar cells using ionic liquids as their electrolytes , 2004 .

[83]  Kikuko Hayamizu,et al.  Physicochemical Properties and Structures of Room Temperature Ionic Liquids. 1. Variation of Anionic Species , 2004 .

[84]  D. Rooney,et al.  An investigation of the radiochemical stability of ionic liquids , 2002 .

[85]  Peter Wasserscheid,et al.  Ionic Liquids in Synthesis , 2002 .

[86]  M. Goto,et al.  Use of ionic liquids in a lipase-facilitated supported liquid membrane , 2003, Biotechnology Letters.

[87]  Elias Stathatos,et al.  A Quasi-Solid-State Dye-Sensitized Solar Cell Based on a Sol−Gel Nanocomposite Electrolyte Containing Ionic Liquid , 2003 .

[88]  M. Matsumoto,et al.  Extraction of organic acids using imidazolium-based ionic liquids and their toxicity to Lactobacillus rhamnosus , 2004 .

[89]  C. Liang,et al.  Ionic liquids: a new class of sensing materials for detection of organic vapors based on the use of a quartz crystal microbalance. , 2002, Analytical chemistry.

[90]  R. P. Swatloski,et al.  Using Caenorhabditis elegans to probe toxicity of 1-alkyl-3-methylimidazolium chloride based ionic liquids. , 2004, Chemical communications.

[91]  Liang Zhao,et al.  Effect of 1-alkyl-3-methylimidazolium-based ionic liquids as the eluent on the separation of ephedrines by liquid chromatography. , 2003, Journal of chromatography. A.

[92]  James H. Davis,et al.  From curiosities to commodities: ionic liquids begin the transition. , 2003, Chemical communications.

[93]  R. C. Weast.  CRC Handbook of Chemistry and Physics , 1973 .

[94]  C. Gordon.  New developments in catalysis using ionic liquids , 2001 .

[95]  J. Brennecke,et al.  Ionic liquids: Innovative fluids for chemical processing , 2001 .

[96]  C. Hardacre,et al.  Small-Angle X-ray Scattering Studies of Liquid Crystalline 1-Alkyl-3-methylimidazolium Salts , 2002 .

[97]  Hoon Sik Kim,et al.  Ionic Liquids as Electrolytes for Li Ion Batteries , 2004 .

[98]  Y. Chauvin,et al.  Catalytic dimerization of alkenes by nickel complexes in organochloroaluminate molten salts , 1990 .

[99]  V. Luzzati,et al.  La structure des colloïdes d'association. III. Description des phases mésomorphes des savons de sodium purs, rencontrées au‐dessus de 100°C , 1961 .

[100]  J. Pernak,et al.  Anti-microbial activities of ionic liquids , 2003 .

[101]  Wolfgang Arlt,et al.  Influence of Ionic Liquids on the Phase Behavior of Aqueous Azeotropic Systems , 2004 .

[102]  J. Wilkes.  The Past, Present and Future of Ionic Liquids as Battery Electrolytes , 2003 .

[103]  R. Weiss,et al.  Phase Characterization and Properties of Completely Saturated Quaternary Phosphonium Salts. Ordered, Room-Temperature Ionic Liquids , 2002 .

[104]  K. Seddon,et al.  Influence of chloride, water, and organic solvents on the physical properties of ionic liquids , 2000 .

[105]  Sushma Chauhan,et al.  Chemical and biochemical transformations in ionic liquids , 2005 .

[106]  M. Watanabe,et al.  Brønsted acid-base ionic liquids and their use as new materials for anhydrous proton conductors. , 2003, Chemical communications.

[107]  G. G. Stokes.  "J." , 1890, The New Yale Book of Quotations.

[108]  M. Vaher,et al.  Application of 1-alkyl-3-methylimidazolium-based ionic liquids in non-aqueous capillary electrophoresis. , 2002, Journal of chromatography. A.

[109]  P. Scammells,et al.  Biodegradable ionic liquids Part II. Effect of the anion and toxicology , 2005 .

[110]  Paul Scovazzo,et al.  Gas separations using non-hexafluorophosphate [PF6]− anion supported ionic liquid membranes , 2004 .

[111]  Joan F. Brennecke,et al.  Thermophysical Properties of Imidazolium-Based Ionic Liquids , 2004 .

[112]  C. Jørgensen,et al.  Enzyme Catalysed Synthesis in Ambient Temperature Ionic Liquids , 2001 .

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

[114]  D. Armstrong,et al.  High-stability ionic liquids. A new class of stationary phases for gas chromatography. , 2003, Analytical chemistry.

[115]  Yuzhong Zhang,et al.  Poly(isonicotinic acid) modified glassy carbon electrode for electrochemical detection of norepinephrine , 2002 .

[116]  O. Francescangeli,et al.  A2[MX4] Copper(II) Pyridinium Salts. From Ionic Liquids to Layered Solids to Liquid Crystals , 2001 .

[117]  S. N. Baker,et al.  A new class of cationic surfactants inspired by N-alkyl-N-methyl pyrrolidinium ionic liquids. , 2004, The Analyst.

[118]  B. Ondruschka,et al.  Ionic liquids and their heating behaviour during microwave irradiation – a state of the art report and challenge to assessment , 2003 .

[119]  Yong‐Sheng Hu,et al.  An alternative ionic liquid based electrolyte for dye-sensitized solar cells , 2004, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[120]  Mustafizur Rahman,et al.  Application of ionic liquids as low-volatility plasticizers for PMMA , 2003 .

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

[122]  J. Pernak,et al.  Anti-microbial activities of protic ionic liquids with lactate anion , 2004 .

[123]  Christoph Werner,et al.  Corrosion behaviour of ionic liquids , 2005 .

[124]  Mary Jane Hale,et al.  Advanced Thermal Storage Fluids for Solar Parabolic Trough Systems , 2002 .

[125]  H. Ohno,et al.  Effect of Methyl Groups onto Imidazolium Cation Ring on Liquid Crystallinity and Ionic Conductivity of Amphiphilic Ionic Liquids , 2004 .

[126]  Robin D. Rogers,et al.  Ionic liquids as green solvents : progress and prospects , 2003 .

[127]  R. Singer,et al.  Ionic Liquids: The Neglected Issues , 2005 .

[128]  D. Bélanger,et al.  Electrochemical Polymerization and Characterization of Poly(3-(4-fluorophenyl)thiophene) in Pure Ionic Liquids , 2002 .

[129]  J. Zabinski,et al.  Ionic Liquid Lubrication Effects on Ceramics in a Water Environment , 2004 .

[130]  R. Poźniak,et al.  New Ionic Liquids and Their Antielectrostatic Properties , 2001 .

[131]  J. Mays,et al.  Application of ionic liquids as plasticizers for poly(methyl methacrylate). , 2002, Chemical communications.

[132]  M. Ingram,et al.  Application of Complementary Experimental Techniques to Characterization of the Phase Behavior of [C16mim][PF6] and [C14mim][PF6] , 2003 .

[133]  Ray H. Baughman,et al.  Investigation of ionic liquids as electrolytes for carbon nanotube electrodes , 2004 .

[134]  R. Kaliszan,et al.  Suppression of deleterious effects of free silanols in liquid chromatography by imidazolium tetrafluoroborate ionic liquids. , 2004, Journal of chromatography. A.

[135]  J. Clyburne,et al.  Phosphonium ionic liquids as reaction media for strong bases. , 2005, Chemical communications.

[136]  B. Ondruschka,et al.  Effects of ionic liquids on the acetylcholinesterase – a structure–activity relationship consideration , 2004 .

[137]  Wang,et al.  Tribological performance of an ionic liquid as a lubricant for steel/aluminium contacts , 2003 .

[138]  A. Lewandowski,et al.  Polymer Electrolyte Based on Ionic Liquid (EMIm)3PO4 as an Electrolyte for Electrochemical Capacitors , 2004 .

[139]  P. Stepnowski,et al.  Evaluating the cytotoxicity of ionic liquids using human cell line HeLa , 2004, Human & experimental toxicology.

[140]  A. Latała,et al.  Marine toxicity assessment of imidazolium ionic liquids: acute effects on the Baltic algae Oocystis submarina and Cyclotella meneghiniana. , 2005, Aquatic toxicology.

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

[142]  J. Shreeve,et al.  Phosphazene-based ionic liquids: synthesis, temperature-dependent viscosity, and effect as additives in water lubrication of silicon nitride ceramics. , 2004, Inorganic chemistry.

[143]  V. Busico,et al.  Polymorphism in anhydrous amphiphilic systems. Long-chain primary n-alkylammonium chlorides , 1983 .

[144]  K. R. Seddon,et al.  LIQUID-CRYSTALLINE IONIC LIQUIDS , 1996 .

[145]  Hua Zhao.  Review: Current studies on some physical properties of ionic liquids , 2003 .

[146]  T. Okajima,et al.  Bioelectrochemistry of molecular oxygen and reactive oxygen species 122. O2 gas sensor using supported hydrophobic room-temperature ionic liquid membrane-coated electrode , 2004 .

[147]  B. Scrosati,et al.  Advances in lithium-ion batteries , 2002 .

[148]  W. Arlt,et al.  Tailor-made ionic liquids , 2005 .

[149]  M. Andre,et al.  Ionic liquids as advantageous solvents for headspace gas chromatography of compounds with low vapor pressure. , 2005, Analytical chemistry.

[150]  Merike Vaher,et al.  Ionic liquids as electrolytes for nonaqueous capillary electrophoresis , 2002, Electrophoresis.

[151]  C. Bazuin,et al.  The thermotropic mesophase structure of two long-chain alkyl pyridinium halides , 1986 .

[152]  Ying Liu,et al.  Electrochemical and bioelectrochemistry properties of room-temperature ionic liquids and carbon composite materials. , 2004, Analytical chemistry.

[153]  G. Powell,et al.  Phosphonium Ionic Liquids as Solvents for Nitration Reactions of Arenes , 2005 .

[154]  Hua Zhao,et al.  Use of ionic liquids as ‘green’ solvents for extractions , 2005 .

[155]  Peng Wang,et al.  Gelation of ionic liquid-based electrolytes with silica nanoparticles for quasi-solid-state dye-sensitized solar cells. , 2003, Journal of the American Chemical Society.

[156]  Roger A. Sheldon,et al.  Biocatalysis in ionic liquids. , 2002, Chemical reviews.

[157]  B. H. Kim,et al.  Electrochemical Polymerization of Polypyrrole Nanotubes and Nanowires in Ionic Liquid , 2004 .

[158]  John S. Wilkes,et al.  Thermochemistry of ionic liquid heat-transfer fluids , 2005 .

[159]  Laigui Yu,et al.  Room-temperature ionic liquids: a novel versatile lubricant. , 2001, Chemical communications.