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A kind of protonated pyrazole ionic liquid and the method of using it to catalyze the synthesis of cyclic carbonate

A technology of cyclic carbonates and ionic liquids, applied in chemical instruments and methods, physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, etc., can solve complex synthesis process, harsh reaction conditions, catalyst Expensive and other issues, to achieve the effect of simple synthesis process, high reactivity, and good industrial application prospects

Active Publication Date: 2019-11-05
HENAN UNIVERSITY
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Problems solved by technology

[0004] The purpose of the present invention is to solve technical problems such as the use of toxic organic solvents, expensive catalysts, complex synthesis processes, and harsh reaction conditions in the existing methods for synthesizing cyclic carbonates, and to provide a catalytic synthesis of protonated pyrazole-based ionic liquids Cyclic carbonate method

Method used

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  • A kind of protonated pyrazole ionic liquid and the method of using it to catalyze the synthesis of cyclic carbonate
  • A kind of protonated pyrazole ionic liquid and the method of using it to catalyze the synthesis of cyclic carbonate
  • A kind of protonated pyrazole ionic liquid and the method of using it to catalyze the synthesis of cyclic carbonate

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Experimental program
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Embodiment 1-1

[0016] Example 1-1: The protonated pyrazole ionic liquid is 1-methylpyrazole hydrobromide.

[0017] The preparation method of 1-methylpyrazole hydrobromide in the present embodiment is as follows:

[0018] Add 1.23g (15mmol) of 1-methylpyrazole and 3.102g (18mmol) of hydrobromic acid into a 100mL three-necked flask respectively, and stir for 15-30h; Yellow solid 1-methylpyrazole hydrobromide ionic liquid, yield 93%.

[0019] 1 H NMR (400MHz, DMSO-d 6 )δ: 7.78(d, J=2.2Hz, 1H), 7.55(d, J=2.0Hz, 1H), 6.29(t, J=2.2Hz, 1H), 5.30(s, 8H), 3.86(s, 3H).

[0020] 13 C NMR (101MHz, D 2 O)δ:136.16,134.44,107.76,37.72.MS(ESI):m / z:83[M-Br] + .

Embodiment 1-2

[0021] Example 1-2: The protonated pyrazole ionic liquid is 1,3-dimethylpyrazole hydrobromide.

[0022] In the present embodiment, the preparation method of 1,3-dimethylpyrazole hydrobromide is as follows:

[0023] Add 1.442g (15mmol) of 1,3-dimethylpyrazole and 3.102g (18mmol) of hydrobromic acid into a 100mL three-neck flask respectively, and stir for 15-30h; after the reaction, remove water, and wash the product with ethyl acetate. Drying gave white solid 1,3-dimethylpyrazole hydrobromide ionic liquid with a yield of 83%.

[0024] 1 H NMR (400MHz, DMSO-d 6 )δ: 7.83(d, 1H), 6.22(d, J=2.6Hz, 1H), 3.85(s, J=2.0Hz, 3H), 2.23(s, 3H).

[0025] 13 C NMR (101MHz, D 2 O)δ: 146.04, 136.48, 107.18, 37.31, 10.26. MS (ESI): m / z: 97 [M-Br] + .

Embodiment 1-3

[0026] Example 1-3: The protonated pyrazole ionic liquid is 1,5-dimethylpyrazole hydrobromide.

[0027] In the present embodiment, the preparation method of 1,5-dimethylpyrazole hydrobromide is as follows:

[0028] Add 1.442g (15mmol) of 1,5-dimethylpyrazole and 3.102g (18mmol) of hydrobromic acid into a 100mL three-neck flask respectively, and stir for 15-30h; after the reaction, remove water, and wash the product with ethyl acetate. Drying gave white solid 1,5-dimethylpyrazole hydrobromide ionic liquid with a yield of 70%.

[0029] 1 H NMR (400MHz, DMSO-d 6 )δ: 7.47(d,1H),6.14(d,J=1.9Hz,1H),3.75(d,J=2.1Hz,3H),2.27(d,J=2.6Hz,3H).

[0030] 13 C NMR (101MHz, D 2 O)δ: 146.08, 132.88, 107.70, 34.86, 10.19. MS (ESI): m / z: 97 [M-Br] + .

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Abstract

The invention provides a protonated pyrazole ionic liquid, and a method used for catalytic synthesis of cyclic carbonate with the protonated pyrazole ionic liquid. The structure formula of the protonated pyrazole ionic liquid is disclosed in the invention. According to the method, the protonated pyrazole ionic liquid and an epoxy compound are introduced into a high temperature reaction kettle at a molar ratio of 1:10-300, CO2 is introduced into the high temperature reaction kettle until the pressure in the high temperature reaction kettle is increased to 1 to 4MPa, constant temperature constant pressure reaction is carried out for 1 to 4h at 100 to 150 DEG C, and cyclic carbonate is obtained via post-treatment. Compared with the prior art, the method possesses following advantages: reaction conditions are mild, catalyst activity is high, no organic solvent is used in the process, and the catalysis reaction process is friendly to the environment.

Description

technical field [0001] The invention belongs to the technical field of green chemical synthesis, and in particular relates to a protonated pyrazole ionic liquid and a method for catalyzing and synthesizing cyclic carbonate using it. Background technique [0002] With the development of social economy, CO 2 The production of the earth has had a huge impact on the earth's environment, and the resulting greenhouse effect has attracted widespread attention from all countries. Therefore, the control of atmospheric CO 2 Alleviating its impact on the greenhouse effect has become one of the major problems to be solved in the new century. Therefore, in this situation, the effective capture and utilization of CO 2 Become a current CO 2 Research hotspot of chemical fixation. [0003] CO 2 As a cheap and abundant renewable resource, the synthesis of cyclic carbonates via cycloaddition reaction and conversion of epoxides is one of the most promising approaches. The synthesized cyc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/12B01J31/02C07D317/36C07D317/38
CPCB01J31/0284C07D231/12C07D317/36C07D317/38
Inventor 张敬来王腾飞任铁钢王丽黎桂辉马源
Owner HENAN UNIVERSITY
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