Alkyl-substituted ethyl acetate-based guanidine ionic liquid as well as preparation and application thereof

The technology of ethyl acetate-based guanidine and ethyl acetate-based tetramethyl guanidine is applied to liquid catalysts and application fields, and can solve the problems of complicated ionic liquid synthesis process, environmental pollution and high preparation cost, and achieves simple post-processing and avoidance of The effect of organic solvent, simple steps

Active Publication Date: 2020-07-10
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The synthesis process of ionic liquids in the prior art is complicated, the raw materials are expensive, the preparation cost is high, the environment is polluted or the preservation is difficult, etc., and it is difficult to be widely used. Therefore, an ionic liquid with simple preparation, good stability and good catalytic performance is developed research matters

Method used

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  • Alkyl-substituted ethyl acetate-based guanidine ionic liquid as well as preparation and application thereof
  • Alkyl-substituted ethyl acetate-based guanidine ionic liquid as well as preparation and application thereof
  • Alkyl-substituted ethyl acetate-based guanidine ionic liquid as well as preparation and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] At a temperature of 60°C, dissolve 2.53g (22mmol) of tetramethylguanidine in 15mL of acetonitrile and mix it to form A solution, dissolve 3.34g (20mmol) of ethyl bromoacetate in acetonitrile to prepare B solution, and then dissolve B solution with 1 drop Slowly add it dropwise at a speed of 1 second, stir and mix in the A solution, stir the reaction system at a temperature of 60°C for 24 hours to carry out the ionization reaction of the following reaction structure formula:

[0020]

[0021] After the reaction finishes, acetonitrile is spin-dried on a rotary evaporator, then washed three times with ethyl acetate 25mL / time, and vacuum-dried at room temperature to obtain a light yellow product that is bromo-ethyl acetate-based tetramethylguanidine ionic liquid, and its yield is 86%.

Embodiment 2

[0023] At a temperature of 60°C, dissolve 2.53g (22mmol) of tetramethylguanidine in 15mL of acetonitrile and mix to form solution A, dissolve 3.62g (20mmol) of ethyl 2-bromopropionate in acetonitrile to form solution C, and then dissolve solution C Slowly add it dropwise at a rate of 1 drop / second, stir and mix in the A solution, and stir the reaction system at 60°C for 24 hours to carry out the ionization reaction of the following reaction structure formula:

[0024]

[0025] After the reaction was finished, the acetonitrile was spin-dried on a rotary evaporator, washed three times with ethyl acetate 25mL / time, and vacuum-dried at room temperature to obtain a light yellow product that was bromo-methylacetate-based tetramethylguanidine ionic liquid, which produced The rate is 84%.

Embodiment 3

[0027] At a temperature of 60°C, 2.53g (22mmol) of tetramethylguanidine was dissolved in 15mL of acetonitrile and mixed to form A solution, 5.02g (20mmol) of ethyl 2-bromooctanoate was dissolved in acetonitrile to prepare D solution, and then D solution was prepared with Slowly add dropwise at a rate of 1 drop / second, stir and mix in solution A, and stir the reaction system at 60°C for 24 hours to carry out the ionization reaction of the following reaction structure formula:

[0028]

[0029] After the reaction was finished, the acetonitrile was spin-dried on a rotary evaporator, washed three times with 25 mL / time of ethyl acetate, and vacuum-dried at room temperature to obtain a light yellow product that was bromo-n-hexyl ethyl acetate tetramethylguanidine ionic liquid, which produced The rate is 83%.

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Abstract

The invention discloses alkyl-substituted ethyl acetate-based guanidine ionic liquid as well as preparation and application thereof, which are characterized in that tetramethylguanidine and 2-bromo ester are ionized to obtain alkyl-substituted ethyl acetate-based guanidine ionic liquid, and the alkyl-substituted ethyl acetate-based guanidine ionic liquid is applied as a catalyst to formylation and methylation reactions of carbon dioxide, N-methylaniline and derivatives of the N-methylaniline to selectively generate N-methylformylaniline or N, N-dimethylaniline and derivatives thereof. Compared with the prior art, the alkyl-substituted ethyl acetate-based guanidine ionic liquid has the advantages of good catalytic performance, mild reaction conditions, simple post-treatment, simple synthesis, low cost, greenness and high efficiency, avoids the use of a large amount of organic solvents when being used as a solvent and a catalyst at the same time, and has important meanings in the research of medicinal chemistry and medical intermediate compounds.

Description

technical field [0001] The invention relates to the technical field of liquid catalyst and its application, in particular to an alkyl-substituted ethyl acetate-based guanidine ionic liquid, its preparation and its application in carbon dioxide reaction. Background technique [0002] As a non-toxic, harmless, abundant, cheap and easy-to-obtain carbon-one resource, it has become the goal pursued by industry and academia to convert carbon dioxide into high value-added products by chemical methods. In recent years, the reaction of carbon dioxide and N-methylaniline under the condition of organic base can selectively generate N-methylformanilide and N,N-dimethylaniline, which are important pharmaceutical intermediates, have been developed, causing Scientists are widely concerned, and finding a catalytic system that can efficiently catalyze this reaction under milder conditions has always been the direction of everyone's efforts. [0003] Ionic liquids have extremely low vapor pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C279/14C07C277/08B01J31/02B01J35/12C07C231/10C07C233/03C07C233/15C07C233/25C07C209/02C07C211/48C07C211/52C07C213/00C07C217/84
CPCC07C279/14C07C277/08B01J31/0279B01J35/12C07C231/10C07C209/02C07C213/00C07C233/03C07C233/15C07C233/25C07C211/48C07C211/52C07C217/84Y02P20/54
Inventor 吴海虹曹昊天薛腾
Owner EAST CHINA NORMAL UNIV
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