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Anionic N-substituted aniline ionic liquid and preparation method thereof
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A kind of aniline ion, anion type technology, applied in the direction of sulfonate preparation, cyanide reaction preparation, chemical instruments and methods, etc.
Active Publication Date: 2019-08-27
BEIJING NORMAL UNIVERSITY
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[0003] But, so far, there is no any report about the ionic liquid containing N-substituted aniline structure
Method used
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[0033] According to a preferred embodiment of the present invention, the cation (A) in the ionic liquid + ) is an organic cation, such as one selected from formula (I-1) to formula (I-14):
[0034]
[0035] Among them, in formula (I-1) to formula (I-14), R 1 , R 2 , R 3 and R 4 each independently selected from C 1-16 Alkyl, C 1-16 Alkenyl, C 7-22 Aralkyl or C 7-22 The aralkenyl group, preferably selected from C 1-12 Alkyl or C 1-12 The alkenyl group, more preferably selected from C 4-12 Alkyl or C 4-12 the alkenyl.
[0036] In a further preferred embodiment, the cation (A + ) is selected from one of formula (I-1) to formula (I-6).
[0037] In a further preferred embodiment, the cation (A) in the ionic liquid + ) is selected from formula (I-1), such as 1-butyl-3-methylimidazolium cation, 1-dodecyl-3-methylimidazolium cation, 1-vinyl-3-butylimidazolium cation.
[0038] According to a preferred embodiment of the present invention, in formula (I), R is selected f...
Embodiment 1
[0099] Example 1 1-Butyl-3-methylimidazole 2-anilinoacetate ([BMIM][2-AnAc])
[0100] Wash 50g of Amberlite-IRA410 type anion resin with deionized water until it is colorless, then stir it with 5vol% HCl for 7h, wash it with deionized water until it is neutral, and pack it into a column; then rinse with 2mol / L NaOH until there is no Cl - (with AgNO 3 test); wash with distilled water until neutral.
[0101] Dissolve 10.0068g (0.043mmol) of [BMIM]Br in 20mL of deionized water, and slowly pass through two resin columns to obtain [BMIM]OH solution.
[0103] Water was removed by rotary evaporation to obtain a brownish-yellow viscous liquid, which was vacuum-dried at 60°C for 24 hours, with a yield of 76.5%.
[0104] The NMR spectrum of the product is as figure 1 shown.
Embodiment 2
[0105] Example 2 1-butyl-3-methylimidazolium 3-anilinopropionate ([BMIM][3-AnPr])
[0106] The process of Example 1 was repeated, with the difference that 2-anilinoacetic acid was replaced with 3-anilinopropionic acid.
[0107] A brown-yellow viscous liquid was obtained with a yield of 68.2%. The NMR spectrum of the product is as figure 2 shown.
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Abstract
The invention discloses an anionic N-substituted anilineionic liquid. The anion of the ionic liquid contains an N-substituted aniline structure, and preferably the structure of the anionic N-substituted anilineionic liquid is shown in the formula (I). The anionic N-substituted aniline ionic liquid is obtained by making an aqueous solution of a cationic halide salt (AX) pass through anion exchange resin and then carrying out neutralization reaction, or directly carrying out ion exchange. The anionic N-substituted aniline ionic liquid not only has the properties and application of general ionic liquids such as serving as a reaction medium, an additive for polymer materials and the like, but also can act as a corrosion inhibitor to slow the corrosion of metals by acidic media, and even canbe used as a reaction monomer for preparing a polyionic liquid type polyaniline derivative through auto-oxidation polymerization or oxidative copolymerization with aniline, or for preparing a crosslinked polyionic liquid type polyaniline derivative further through other polymerization means such as radical polymerization and the like.
Description
technical field [0001] The invention relates to the field of ionic liquids, in particular to an N-substituted aniline ionic liquid, in particular to an anionic N-substituted aniline ionic liquid and a preparation method thereof. Background technique [0002] Ionic liquids are composed of cations and anions, and are generally liquid below 100 °C. Room temperature ionic liquids have many special properties, such as: designable structure, non-volatile, non-flammable and explosive, good chemical and thermal stability, wide electrochemical window, and can be used as reaction catalysts and solvents. Among the ionic liquids synthesized and studied more at present, the cations are mainly 1,3-dialkylimidazolium cations, alkylpyridinium cations, quaternaryammonium salt cations, quaternaryphosphonium salts, etc., and the anions are mostly BF 4 - 、PF 6 - 、Tf 2 N - 、CF 3 COO - Wait. [0003] However, so far, there has not been any report on ionic liquids containing N-substitut...
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