Title:
ONE-STEP PROCESS FOR THE PREPARATION OF HALIDE-FREE HYDROPHOBIC SALTS
Document Type and Number:
WIPO Patent Application WO/2002/094883
Kind Code:
A3
Abstract:
This invention describes a one pot, single-step process for the preparation of halide-free hydrophobic salts comprising polyalkylated imidazolium cations and various anions in accordance with the following structure, where R1 and R3 represent the either the same or different alkyl groups, and R2, R4, and R5 represent either hydrogen atoms, or the same or different alkyl group substituents; X represents a polyatomic anion that is the conjugate base of an acid. By simply mixing aqueous formaldehyde with an alkyl amine such as methylamine, ethylamine, n-propyl or iso-propylamine, or n-butyl-, iso-butyl, or t-butylamine, or by mixing aqueous formaldehyde with two alkyl amines (preferably one being methylamine, ethylamine, n-propyl- or iso-propylamine, or n-butyl-, iso-butyl, or t-butylamine) and another being n-propyl- or iso-propylamine, or n-butyl-, iso-butyl, or t-butylamine), an acid (such as hexafluorophosphoric acid, trifluoroacetic acid, pentafluoropropionic, heptafluorobutyric acid, or the free acid of a bis(perfluoroalkylsulfony)imide or tris(perfluoroalkylsulfonyl)methide as the source of the anion) and aqueous glyoxal solution, the hydrophobic ionic salts or mixtures thereof thus formed may be conveniently separated directly from the aqueous byproduct layer. Like the single cation hydrophobic salts, these mixed hydrophobic ionic liquids are non-flammable and manifest no detectable vapor pressure up to their decomposition tempperature of greater than 300° C. We have also discovered that, surprisingly, ternary mixtures of dialkylated ionic liquids manifest higher ionic conductivities than a single ionic liquid of the mixture alone. This property benefits electrochemical power source applications such as batteries and capacitors. Furthermore, we have discovered that ternary mixtures of dialkylated ionic liquids absorb microwave radiation more efficiently than a single ionic liquid of the mixture alone. This property benefits microwave-induced synthetic reactions. Such physical and chemical properties make it possible to employ inexpensive mixtures of polyalkylated imidazolium cations in an advantageous manner as thermal transfer fluids, high temperature lubricants, and plasticizers, and as solvents in the areas of electrochemistry, synthetic chemistry, catalysis, and separations chemistry.
Inventors:
REN REX XIAOFENG (US)
KOCH VICTOR R (US)
KOCH VICTOR R (US)
Application Number:
PCT/US2002/001766
Publication Date:
October 24, 2013
Filing Date:
January 22, 2002
Export Citation:
Assignee:
COVALENT ASSOCIATES INC (US)
REN REX XIAOFENG (US)
KOCH VICTOR R (US)
REN REX XIAOFENG (US)
KOCH VICTOR R (US)
International Classes:
C07D233/56; C07D233/54; C07D233/58; C07D521/00; C07F9/28
Foreign References:
| US5182405A | 1993-01-26 |
Attorney, Agent or Firm:
HEINE, Holliday, C. et al. (Schurgin Gagnebin & Lebovici LLP,Ten Post Office Squar, Boston MA, US)
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