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Imidazolyl ionic liquid, and synthesizing method and application thereof

A technology of ionic liquids and synthesis methods, applied in chemical instruments and methods, preparation of organic compounds, catalysts of organic compounds/hydrides/coordination complexes, etc., can solve the problems of poor recycling effects, catalyst poisoning, and high production costs of catalysts, etc. problems, to achieve the effect of wide range of applicable substrates, mild reaction conditions and excellent catalytic activity

Inactive Publication Date: 2013-07-17
NORTHWEST UNIV(CN)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The research of using ionic liquid to catalyze Knoevenagel reaction has been reported in many documents at home and abroad, but the common shortcomings are: 1. The universality of the catalyst. Many ionic liquid catalysts reported can only be used for aromatic aldehydes and highly active active methylene The base compound plays a good catalytic role, but it cannot efficiently catalyze or even catalyze the reaction of aliphatic aldehydes, ketones, heterocyclic aldehydes, ketones and active methylene compounds.
2. The mildness of the reaction conditions. Many of the reported reactions are carried out in toxic and harmful organic solvents, or require a large amount of ionic liquid as both a catalyst and a solvent, and some even require high temperature to promote the reaction.
3. The preparation and recycling of catalysts. The synthesis process of some ionic liquids is relatively complicated, and the production cost of catalysts is relatively high, which is not environmentally friendly and economical; the recycling effect of some catalysts is relatively poor, and it is easy to poison the catalyst during the reaction process. Inactive

Method used

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  • Imidazolyl ionic liquid, and synthesizing method and application thereof
  • Imidazolyl ionic liquid, and synthesizing method and application thereof
  • Imidazolyl ionic liquid, and synthesizing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1: the synthesis of ionic liquid A3

[0018] Add 0.01mol 2-(1'-methylene imidazolyl)benzimidazole into 25mL of 25% sodium hydroxide solution, stir and react at 80°C, after the benzimidazole is completely dissolved, slowly add 0.01 mol n-C 8 h 17 Br, continue to react for 6 hours. After the reaction is complete, use a separatory funnel to separate the oil phase in the reaction solution, add it to 20mL of toluene, and slowly add 0.01mol n-C 8 h 17 Br, continue to react for 12 hours. After the reaction, the toluene was evaporated to obtain an oily liquid, which was purified by column separation. The purified oily liquid was added to 20 mL of dichloromethane, 0.01 mol of potassium hydroxide was added thereto, and the reaction was stirred at room temperature for 8 hours. After the reaction was completed, the precipitate was filtered off, and dichloromethane was distilled off to obtain the crude ionic liquid A3. The crude product was washed three times with ...

Embodiment 2

[0019] Embodiment 2: the synthesis of ionic liquid B3

[0020] Add 0.01mol 2-(1'-methylene imidazolyl)benzimidazole into 25mL of 25% sodium hydroxide solution, stir and react at 80°C, after the benzimidazole is completely dissolved, slowly add 0.01 mol n-C 8 h 17 Br, continue to react for 6 hours. After the reaction is complete, use a separatory funnel to separate the oil phase in the reaction solution, add it to 20mL of toluene, and slowly add 0.01mol n-C 8 h 17 Br, continue to react for 12 hours. After the reaction, the toluene was evaporated to obtain an oily liquid, which was purified by column separation. The purified oily liquid was added to 50 mL of toluene:methanol (v / v)=2:3 solution, and 0.05 mol of methyl iodide was slowly added dropwise thereto under reflux, and the reaction was continued for 12 hours. After the reaction was completed, the solid generated by the reaction was filtered out with suction, and the obtained solid was recrystallized from ethanol. Th...

Embodiment 3

[0021] Embodiment 3: the synthesis of ionic liquid A6

[0022] Similar to Example 1, the difference is: the raw material n-C 8 h 17 Br to C 6 h 5 CH 2 Cl, 3.25 g of pure ionic liquid A6 was obtained, and the yield was 82%. Mass spectrum (m / z): 379.20. NMR: 1 H NMR (400 MHz, CH 3 OD) δ: 9.06 (s, 1H), 7.74 (d, J = 6.8 Hz, 1H), 7.58 (dd, J = 5.2, 2.8 Hz, 3H), 7.48 – 7.36 (m, 7H), 7.33 – 7.29 (m, 3H), 7.05 (dd, J = 6.3, 2.6 Hz, 2H), 5.82 (s, 2H), 5.68 (s, 2H), 5.34 (s, 2H); 13 C NMR (101 MHz, CH 3OD) δ: 147.21, 141.39, 136.90, 135.86, 135.74, 133.40, 129.07, 129.05, 128.77, 128.54, 127.83, 125.96, 124.02, 123.19, 123.02, 122.53, 118.93, 110.58, 52.90, 46.60, 45.19。 Infrared (KBr): ν / cm -1 : 3449.42, 3061.24, 2968.84, 1623.20, 1562.36, 1452.64, 1332.61, 1161.06, 870.50, 745.70, 706.31, 641.15.

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Abstract

The invention discloses imidazolyl ionic liquid as formula I and a synthesizing method thereof. When the imidazolyl ionic liquid is applicable to Knoevenagel reactions, the imidazolyl ionic liquid has the advantages that imidazolyl ionic liquid is wide in applicable substrate range, short in reaction time, mild in reaction actions, and reusable.

Description

technical field [0001] The invention relates to an imidazole-based ionic liquid, a synthesis method thereof and an application in catalytic Knoevenagel reaction, belonging to the field of organic synthesis chemistry. Background technique [0002] Ionic liquids refer to salts that are all composed of anions and cations and are liquid at room temperature or near room temperature. Sometimes they are also called low-temperature molten salts. They are generally composed of organic cations, organic anions, and inorganic anions. Compared with traditional electrolytes, catalysts and organic solvents, ionic liquids have a series of outstanding features: (1) a wide temperature range in liquid state, from below room temperature to close to 300 ° C; (2) through the design of anions and cations, its The acidity can be adjusted to super acidity, and its solubility to organic compounds, inorganic compounds, and polymers can also be adjusted; (3) non-explosive, non-flammable, non-volatile, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/06B01J31/02C07C253/30C07C255/34C07C255/41C07C255/36C07C255/37C07C255/57C07C255/35C07C255/40C07C255/31C07D213/57C07D307/54
Inventor 李剑利庞鹏万克柔张金
Owner NORTHWEST UNIV(CN)
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