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    • 2. 发明申请
    • ONE-STEP PROCESS FOR THE PREPARATION OF HALIDE-FREE HYDROPHOBIC SALTS
    • WO2002094883A3
    • 2002-11-28
    • PCT/US2002/001766
    • 2002-01-22
    • COVALENT ASSOCIATES, INC.REN, Rex, XiaofengKOCH, Victor, R.
    • REN, Rex, XiaofengKOCH, Victor, R.
    • C07D233/56C07D233/58
    • 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 R 1 and R 3 represent the either the same or different alkyl groups, and R 2 , R 4 , and R 5 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.
    • 3. 发明申请
    • ONE-STEP PROCESS FOR THE PREPARATION OF HALIDE-FREE HYDROPHOBIC SALTS
    • 制备无卤素疏水盐的一步法
    • WO2002094883A2
    • 2002-11-28
    • PCT/US2002/001766
    • 2002-01-22
    • COVALENT ASSOCIATES, INC.REN, Rex, XiaofengKOCH, Victor, R.
    • REN, Rex, XiaofengKOCH, Victor, R.
    • C08F
    • C07D231/12C07D233/56C07D249/08C07F9/28
    • 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 R 1 and R 3 represent the either the same or different alkyl groups, and R 2 , R 4 , and R 5 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.
    • 本发明描述了根据以下结构制备包含多烷基化咪唑鎓阳离子和各种阴离子的不含卤化物的疏水盐的一锅一步法,其中R 1和R 3表示相同或 不同的烷基,R 2,R 4和R 5表示氢原子或相同或不同的烷基取代基; X表示作为酸的共轭碱的多原子阴离子。 通过简单地将含水甲醛与烷基胺如甲胺,乙胺,正丙基或异丙​​胺或正丁基,异丁基或叔丁胺混合,或通过混合甲醛水溶液与两种烷基胺(优选一种 甲胺,乙胺,正丙基或异丙​​胺或正丁基 - ,异丁基或叔丁胺),另一种是正丙基或异丙​​胺或正丁基 - 异丁基 ,或叔丁胺),酸(例如六氟磷酸,三氟乙酸,五氟丙酸,七氟丁酸或作为阴离子源的双(全氟烷基磺酰基)酰亚胺或三(全氟烷基磺酰基)甲基化物的游离酸)和乙二醛水溶液 溶液,由此形成的疏水性离子盐或其混合物可以方便地从水性副产物层直接分离。 像单一的阳离子疏水盐一样,这些混合的疏水性离子液体是不易燃的,并且在大于300℃的分解温度下不显示可检测的蒸气压。我们还发现令人惊讶的是,二烷基化离子液体的三元混合物表现出更高的 离子电导率比单独的混合物的单一离子液体。 这种性能有利于电化学电源应用,如电池和电容器。 此外,我们已经发现,二烷基化离子液体的三元混合物比单独的混合物的单一离子液体更有效地吸收微波辐射。 这种性质有利于微波诱导的合成反应。 这种物理和化学性质使得可以以有利的方式使用廉价的多烷基化咪唑鎓阳离子混合物作为热传递流体,高温润滑剂和增塑剂,以及在电化学,合成化学,催化和分离化学领域中的溶剂。