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Ionic liquid loaded ruthenium catalyst containing pyridine ligand and producing method thereof

A technology of ionic liquid and ruthenium catalyst, applied in the field of catalyst and its preparation, can solve problems such as poor solubility, and achieve the effect of improving poor solubility and expanding the scope of application

Inactive Publication Date: 2008-03-12
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to overcome the disadvantages of poor solubility of existing ruthenium catalysts in polar solvents, improve their solubility in polar solvents such as ionic liquids, thereby realizing the polymerization reaction in a pure ionic liquid environment

Method used

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  • Ionic liquid loaded ruthenium catalyst containing pyridine ligand and producing method thereof
  • Ionic liquid loaded ruthenium catalyst containing pyridine ligand and producing method thereof
  • Ionic liquid loaded ruthenium catalyst containing pyridine ligand and producing method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Synthesis of 1,2-Dimethyl-3-hydroxyethylimidazolium Chloride Ionic Liquid (1)

[0038]

[0039] Add 1,2-dimethylimidazole (19.2g, 200mmol) and chloroethanol (16.1ml, 240mmol) into a 250ml reaction flask, dissolve in 20ml of toluene, react at 110°C for 8 hours, stop the reaction, let it stand, and pour off the upper layer toluene. Then wash three times with toluene (20ml×3). Add 20ml of acetone to the crude product, stir at reflux at 70°C for 30min, let stand, and pour off the upper solvent. Repeat washing with acetone twice, let it stand, and cool down, and a light yellow solid is precipitated in the lower layer. The light yellow crude product was recrystallized from acetonitrile to obtain white crystals, which were dried in vacuo to obtain compound 1 (27.5 g, yield 78%). 1 H-NMR (D 2 O, δ): 7.35(d, 2H, N-CH=HC-N), 4.22(t, 2H, N-CH 2 ), 3.87(t, 2H, CH2 -OH), 3.74(s, 3H, N-CH 3 ), 2.56(s, 3H, C-CH 3 ); 13 C-NMR (D 2 O, δ): 146.36 (N-C-N), 123.76, 122.39 (HC=C...

Embodiment 2

[0041] Synthesis of 1,2-Dimethyl-3-hydroxyethylhexafluorophosphate Ionic Liquid (2)

[0042]

[0043] Will KPF 6 (13.2g, 72mmol) was dissolved in 80ml of water, cooled with an ice-water bath, and then a 50ml aqueous solution of compound 1 (10.6g, 60mmol) was slowly dropped into it. After the dropwise addition, the reaction was gradually raised to room temperature for 12 hours, and the reaction was stopped. The solvent water was removed to obtain a light yellow viscous liquid (containing white solid). Dissolved with 50ml of acetone, filtered, and the filtrate was dried with anhydrous sodium sulfate, and the solvent was removed to obtain a colorless viscous liquid, which was dried in vacuo to obtain compound 2 (14.2g, yield 83%). 1 H-NMR (D 2 O, δ): 7.40 (d, 2H, HC=CH), 4.27 (t, 2H, N-CH 2 ), 3.94(t, 2H, CH 2 -OH), 3.80(s, 3H, N-CH 3 ), 2.62 (s, 3H, C-CH 3 ); 13 C-NMR (D 2 O, δ): 146.36 (N-C-N), 123.76, 122.39 (HC=CH), 61.31 (CH 2 -OH), 51.53 (N-CH 2 ), 36.12 (N-CH...

Embodiment 3

[0045] Synthesis of 1,2-dimethyl-3-ethyl p-toluenesulfonate imidazolium ionic liquid (3)

[0046]

[0047] Under nitrogen protection, 2 (5.72g, 20mmol) was added to a 250ml Schlenk reaction flask, dissolved in 35ml of acetonitrile, then triethylamine (3.4ml, 24mmol) was added, cooled in an ice-water bath. p-Toluenesulfonyl chloride (4.58g, 24mmol) was dissolved in 25mL of acetonitrile and added dropwise under ice-bath conditions. After the dropwise addition, the reaction was maintained at 0-5°C for 1 hour, then raised to room temperature for 10 hours, and the reaction was stopped. Filter, remove solvent, obtain solid and dark viscous liquid, use 100ml CH 2 Cl 2 dissolved and washed several times with water, the organic phase was washed with anhydrous Na 2 SO 4 dry. Remove CH 2 Cl 2 A brown-yellow solid was obtained, which was recrystallized from acetone:ether=2:1 to obtain a light-yellow solid, which was dried in vacuo to obtain 4.84 g of the product, with a yield of...

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Abstract

The present invention relates to a ruthenium catalyst and a preparation method of the catalyst, in particular relates to a pyridine ligand compring and ion liquid supported ruthenium catalyst and a preparation method of the catalyst, and belongs to the catalyst and catalyst preparation technical field. The imidazole ion liquid reacts with 4-hydroxypyridine to get the pyridine group comprising imidazole ion liquid, and the pyridine group comprising imidazole ion liquid coordinates with ruthenium to make the catalyst. As the ruthenium catalyst made comprises the ion liquid section, the catalyst can be well dissolved in a polar solvent, in particular an ion liquid, so as to realize the ring opening metathesis polymerization (ROMP) reaction in the pure ion liquid. The ruthenium eliminates the shortcoming that the prior ruthenium catalyst is provided with the bad solubility in the polar solvent. The catalyst can be dissolved in the polar solvent, like the alcohol, acetone and ion liquid, and further realizes the ring opening metathesis polymerization (ROMP) reaction in the pure ion liquid. Thus, the application scope of the ruthenium is expanded.

Description

technical field [0001] The invention relates to a ruthenium catalyst and a preparation method thereof, in particular to a ruthenium catalyst supported by an ionic liquid containing a pyridine ligand and a preparation method thereof, belonging to the technical field of catalyst and preparation thereof. Background technique [0002] Ruthenium catalyst is an important factor affecting monomer polymerization in ring-opening metathesis polymerization. The existing Grubbs first-generation and second-generation catalysts have become widely used catalysts due to their good stability and functional group tolerance, which can carry out living polymerization and obtain products with well-defined structures. But the Grubbs catalyst only has good solubility in nonpolar solvents such as methylene chloride, benzene, toluene, and has poor solubility in polar solvents such as alcohols, water and ionic liquids, and limits its use in polar solvents. in the ring-opening metathesis polymerizati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22B01J31/28C08F4/80
Inventor 谢美然马卓孔毅韩会景王伟珍史佳鑫李金欣
Owner EAST CHINA NORMAL UNIV
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