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Hydroxyl-containing bivalent imidazole type ionic liquid, preparation method thereof, and application thereof

A hydroxyl-containing divalent imidazole-type and hydroxyl-divalent imidazole-type technology is applied in the field of hydroxyl-containing divalent imidazole-type ionic liquids and their preparations, which can solve the problems of ionic liquid loss of cellulose, thermal and chemical instability, etc., and achieve electrical High chemical stability, good solubility, and good product quality

Inactive Publication Date: 2012-09-19
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the introduction of double bonds, polymerization will be initiated to generate new polyelectrolytes, so the ionic liquids containing unsaturated double bonds have the disadvantages of thermal and chemical instability, and it is easy to cause the loss of ionic liquids when dissolving cellulose and cellulose degradation
[0005] Current studies have shown that ionic liquids, as green solvents, have shown a good development trend in the dissolution of derivatized cellulose, but there are still many shortcomings, and most of the ionic liquids currently selected are conventional imidazole-based ionic liquids. Hydroxyl divalent imidazole type ionic liquid and its preparation method and the research on dissolving cellulose have not been reported yet

Method used

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  • Hydroxyl-containing bivalent imidazole type ionic liquid, preparation method thereof, and application thereof
  • Hydroxyl-containing bivalent imidazole type ionic liquid, preparation method thereof, and application thereof
  • Hydroxyl-containing bivalent imidazole type ionic liquid, preparation method thereof, and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 : Preparation of 1,3-bis-(1-alkylimidazolyl)-2-propanol hydrochloride ionic liquid

[0027] Dissolve 40mL of 1-methylimidazole (20.6g, 0.50mol) in 80mL of ethanol, and add 21mL of concentrated hydrochloric acid (0.25mol) in batches under stirring at room temperature. -Chloro-propylene oxide (23.12g, 0.25mol) was added dropwise to the reaction solution. After the drying tube was equipped, the reaction bottle was placed in the water bath of the experimental ultrasonic cleaner, and the reaction was performed under ultrasonic radiation (power 300W, frequency 40KHz) at 30°C for 2.5h. The solvent was removed by rotary evaporation at 60°C under reduced pressure, and a colorless liquid (59.33 g, 83%) was obtained after vacuum drying. 1 H-NMR (500MHz, D 2 O): δ8.47(s, 1H), 8.39(s, 1H), 7.30(m, 4H), 4.22(dd, J=2.10, 13.20Hz, 1H), 4.20(m, 2H), 3.66(s , 3H), 3.70(s, 3H), 3.45(m, 2H). 13 C-NMR (500MHz, D 2 O): δ136.34(CH), 134.82(CH), 123.44(CH), 122.78(CH), 122.69(C...

Embodiment 2

[0028] Example 2 : Preparation of 1,3-bis-(1-alkylimidazolyl)-2-propanol hydrochloride tetrafluoroborate ionic liquid

[0029] Dissolve 40mL of 1-methylimidazole (20.6g, 0.50mol) in 90mL of ethanol, add 33mL of tetrafluoroboric acid (0.25mol) in batches under stirring at room temperature, after the addition, the reaction solution is naturally cooled to room temperature, and 19.6mL of 3-Chloro-propylene oxide (23.12 g, 0.25 mol) was added dropwise to the reaction solution. After the drying tube was equipped, the reaction bottle was placed in the water bath of the ultrasonic cleaner used in the experiment, and was subjected to ultrasonic radiation (power 300W, frequency 40KHz) at 40°C for 1.5h. The solvent was removed by rotary evaporation at 60°C under reduced pressure, and a light yellow liquid (71.48 g, 83%) was obtained after vacuum drying. 1 H-NMR (500MHz, D 2 O): δ8.58(s, 1H), 8.43(s, 1H), 7.30(m, 4H), 4.29(dd, J=2.25, 13.25Hz, 1H), 4.127(m, 2H), 3.74(s , 3H), 3.73(s,...

Embodiment 3

[0030] Example 3 : Preparation of 1,3-bis-(1-alkylimidazolyl)-2-propanol hydrochloride acetate ionic liquid

[0031] Dissolve 40mL of 1-methylimidazole (20.6g, 0.50mol) in 90mL of ethanol, and add 14mL of acetic acid (0.25mol) in batches under stirring at room temperature. - Propylene oxide (23.12 g, 0.25 mol) was added dropwise to the reaction solution. After the drying tube was equipped, the reaction bottle was placed in the water bath of the ultrasonic cleaner used in the experiment, and reacted under ultrasonic radiation (power 300W, frequency 40KHz) at 25°C for 3.5h. The solvent was removed by rotary evaporation at 60°C under reduced pressure, and a colorless liquid (68.11 g, 86%) was obtained after vacuum drying. 1 H-NMR (500MHz, D 2 O): δ8.62(s, 1H), 8.48(s, 1H), 7.36(m, 4H), 4.34(dd, J=2.36, 13.40Hz, 1H), 4.22(m, 2H), 3.84(s , 3H), 3.76(s, 3H), 3.60(m, 2H), 2.22(s, 3H). 13 C-NMR (500MHz, D 2 O): δ188.14(C=O), 138.88(CH), 136.24(CH), 125.44(CH), 124.48(CH), 123.8...

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Abstract

The invention discloses a hydroxyl-containing bivalent imidazole type ionic liquid, having the following structural formula, wherein R1, R2 and X are defined as the claims and the specification. A preparation method of the hydroxyl-containing bivalent imidazole type ionic liquid comprises the following steps of: dissolving a certain amount of 1-alkyl imidazole into absolute ethyl alcohol, adding acid HX in batches in case of stirring under room temperature, naturally cooling to the room temperature after adding, and dropwise adding 3-chlorine epoxypropane into reaction solution in case of stirring; and putting a reaction bottle into an ultrasonic cleaner for a laboratory, in case of ultrasound irradiation, reacting for a while under a certain temperature, carrying out reduced pressure distillation, and carrying out vacuum drying to obtain the ionic liquid. The invention further relates to the application of the hydroxyl-containing bivalent imidazole type ionic liquid which is independently taken as solvent in the aspect of cellulose dissolving.

Description

Technical field: [0001] The invention belongs to the technical field of chemical material preparation, and relates to a hydroxyl-containing divalent imidazole-type ionic liquid and a preparation method and application thereof. Background technique: [0002] Due to almost no vapor pressure, high chemical and thermal stability, wide electrochemical window, ionic liquids have good solubility for inorganic substances, organic substances, catalysts and polymers, and can be adjusted by designing the cationic part of the ionic liquid Its performance has become the widespread concern of scholars at home and abroad. At present, the research interest in ionic liquids is showing an unprecedented surge trend, and a large number of articles and patents related to the application of ionic liquids in organic synthesis and catalytic chemistry, biotechnology, electrochemistry and materials chemistry have been published (Deetlefs M, Kenneth R, Seddon .Improved preparations of ionic liquids u...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/61D01F2/02D01D5/06
Inventor 詹天荣侯万国
Owner QINGDAO UNIV OF SCI & TECH
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