Evaluating Ionic Liquids as Hypergolic Fuels: Exploring Reactivity from Molecular Structure

A total of 38 ionic liquids (19 of which are new) comprised of 13 cations, 1-propargyl-3-methyl-imidazolium, 1-allyl-3-methyl-imidazolium, 1,3-dimethyl-imidazolium, 1-ethyl-3-methyl-imidazolium, 1-butyl-3-methyl-imidazolium, 1-meth-oxyethyl-3-methyl-imidazolium, 1-methyl-4-butyl-1,2,4-triazolium, 1-methyl-4-allyl-1,2,4-triazolium, 1-methyl-4-amino-1,2,4-tri-azolium, N-butyl-N-methyl-pyrrolidinium, N-allyl-N-methyl-pyrrolidinium, N-allyl-pyridinium, and N-butyl-3-methyl-pyridinium, paired with three anions, dicyanamide, azide, and nitrocyanamide, have been prepared, characterized, and evaluated as potential hypergolic fuels by determining key physical, thermal, and ignition properties. The reactivity of these ionic liquids (32 liquids and 6 solids which melt below 100 °C) was strongly correlated to increased electron density in the cation, while small changes in physical properties had little effect beyond a certain threshold, suggesting that subtle changes in chemical reactivity can greatly influence the ...

[1]  Zhaofu Fei,et al.  Sulfonium-based Ionic Liquids Incorporating the Allyl Functionality , 2007, International Journal of Molecular Sciences.

[2]  R. M. Frazier,et al.  Graphene and graphene oxide can "lubricate" ionic liquids based on specific surface interactions leading to improved low-temperature hypergolic performance. , 2012, Angewandte Chemie.

[3]  Maria Forsyth,et al.  Low viscosity ionic liquids based on organic salts of the dicyanamide anion , 2001 .

[4]  A. Vij,et al.  Liquid azide salts. , 2008, Inorganic chemistry.

[5]  R. Scopelliti,et al.  Nitrile-functionalized pyridinium ionic liquids: synthesis, characterization, and their application in carbon-carbon coupling reactions. , 2004, Journal of the American Chemical Society.

[6]  Stefan Schneider,et al.  Liquid azide salts and their reactions with common oxidizers IRFNA and N2O4. , 2008, Inorganic chemistry.

[7]  Peng Wang,et al.  N-Methyl-N-Allylpyrrolidinium Based Ionic Liquids for Solvent-Free Dye-Sensitized Solar Cells , 2009 .

[8]  C. Macrae,et al.  Mercury CSD 2.0 – new features for the visualization and investigation of crystal structures , 2008 .

[9]  R. D. Verma,et al.  Energetic nitrogen-rich salts and ionic liquids. , 2006, Angewandte Chemie.

[10]  T. Welton,et al.  Evidence for hydrogen bonding in solutions of 1-ethyl-3-methylimidazolium halides, and its implications for room-temperature halogenoaluminate(III) ionic liquids , 1994 .

[11]  G. Nauer,et al.  Syntheses, crystal structures, and polymorphism of quaternary pyrrolidinium chlorides , 2008 .

[12]  G. Saito,et al.  Ionic liquids based on dicyanamide anion: influence of structural variations in cationic structures on ionic conductivity. , 2007, The journal of physical chemistry. B.

[13]  M. Grätzel,et al.  Hydrophobic, Highly Conductive Ambient-Temperature Molten Salts. , 1996, Inorganic chemistry.

[14]  Yanqiang Zhang,et al.  Boronium-cation-based ionic liquids as hypergolic fluids. , 2012, Chemistry.

[15]  Yanqiang Zhang,et al.  Inorganic or organic azide-containing hypergolic ionic liquids. , 2010, Inorganic chemistry.

[16]  Yanqiang Zhang,et al.  Ionic liquids as hypergolic fuels. , 2011, Angewandte Chemie.

[17]  R. Scopelliti,et al.  Synthesis and characterization of ionic liquids incorporating the nitrile functionality. , 2004, Inorganic chemistry.

[18]  Ghanshyam L. Vaghjiani,et al.  Ionic Liquids as Hypergolic Fuels , 2008 .

[19]  Ling He,et al.  Nitrocyanamide-based ionic liquids and their potential applications as hypergolic fuels. , 2010, Chemistry.

[20]  D. Macfarlane,et al.  Thermal degradation of cyano containing ionic liquids , 2006 .

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

[22]  G. Wytze Meindersma,et al.  Density, viscosity, and surface tension of synthesis grade imidazolium,pyridinium, and pyrrolidinium based room temperature ionic liquids , 2009 .

[23]  Dennis W. Smith,et al.  ALKENE- AND ALKYNE-SUBSTITUTED METHYLIMIDAZOLIUM BROMIDES: STRUCTURAL EFFECTS AND PHYSICAL PROPERTIES , 2007 .

[24]  G. Sheldrick.  A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[25]  Young Gyu Kim,et al.  Synthesis and Properties of Pyrrolidinium and Piperidinium Bis(trifluoromethanesulfonyl)imide Ionic Liquids with Allyl Substituents , 2007 .

[26]  A. Ragauskas,et al.  Perdeuterated pyridinium molten salt (ionic liquid) for direct dissolution and NMR analysis of plant cell walls , 2009 .

[27]  Michiel Janssen,et al.  Room-temperature ionic liquids that dissolve carbohydrates in high concentrations , 2005 .

[28]  John D. Clark.  Ignition! An Informal History of Liquid Rocket Propellants , 1972 .

[29]  Craig Clauss,et al.  Distribution A - Approved for Public Release, Distribution Unlimited Development and On-Orbit Performance of a Pressure Regulation Control System for Upper Stage , 2010 .

[30]  Florian Herbst,et al.  Hierarchically Nanostructured Polyisobutylene-Based Ionic Liquids , 2012 .

[31]  S. Son,et al.  Hypergolic ionic liquids to mill, suspend, and ignite boron nanoparticles. , 2012, Chemical communications.

[32]  Michael Grätzel,et al.  A supercooled imidazolium iodide ionic liquid as a low-viscosity electrolyte for dye-sensitized solar cells. , 2006, Inorganic chemistry.

[33]  T. Hawkins,et al.  Green bipropellants: hydrogen-rich ionic liquids that are hypergolic with hydrogen peroxide. , 2011, Angewandte Chemie.

[34]  R. Rinaldi,et al.  Thermal stability of ionic liquids assessed by potentiometric titration , 2010 .

[35]  Robin Taylor,et al.  Mercury: visualization and analysis of crystal structures , 2006 .

[36]  D. Macfarlane,et al.  Ionic liquids based on imidazolium, ammonium and pyrrolidinium salts of the dicyanamide anion , 2002 .

[37]  R. Torresi,et al.  Ether-bond-containing ionic liquids and the relevance of the ether bond position to transport properties. , 2010, The journal of physical chemistry. B.

[38]  Ghanshyam L. Vaghjiani,et al.  Generation of melamine polymer condensates upon hypergolic ignition of dicyanamide ionic liquids. , 2011, Angewandte Chemie.

[39]  Ghanshyam L. Vaghjiani,et al.  Chemical kinetics interpretation of hypergolicity of dicyanamide ionic liquid-based systems , 2011 .

[40]  Yanqiang Zhang,et al.  Dicyanoborate-based ionic liquids as hypergolic fluids. , 2011, Angewandte Chemie.

[41]  Marcin Smiglak,et al.  The second evolution of ionic liquids: from solvents and separations to advanced materials--energetic examples from the ionic liquid cookbook. , 2007, Accounts of chemical research.

[42]  H. Ngo,et al.  Thermal properties of imidazolium ionic liquids , 2000 .

[43]  Ghanshyam L. Vaghjiani,et al.  Soft ionization of thermally evaporated hypergolic ionic liquid aerosols. , 2011, The journal of physical chemistry. A.

[44]  G. Baker,et al.  Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications. , 2012, Chemical Society reviews.

[45]  S. Iyer,et al.  Hypergolic Reaction of Dicyanamide-Based Fuels with Nitric Acid , 2011 .

[46]  Ghanshyam L. Vaghjiani,et al.  Fourier transform infrared studies in hypergolic ignition of ionic liquids. , 2008, The journal of physical chemistry. A.

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

[48]  R. Singh,et al.  Low melting inorganic salts of alkyl-, fluoroalkyl-, alkyl ether-, and fluoroalkyl ether-substituted oxazolidine and morpholine. , 2004, Inorganic chemistry.