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Method for synthesizing acetylenic acid by using terminal alkyne and carbon dioxide

A technology of carbon dioxide and alkynoic acid, which is applied in the direction of organic chemical methods, chemical instruments and methods, and the preparation of organic compounds, can solve the problems of complex catalyst synthesis, harsh reaction conditions, and high catalytic costs, and achieve industrial production application prospects and good, The effect of mild reaction conditions and high yield

Pending Publication Date: 2021-07-23
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In summary, although many methods have been reported for the synthesis of alkynoic acids from carbon dioxide, their practical application is still difficult due to harsh reaction conditions, complex catalyst synthesis, high catalytic cost, etc.

Method used

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  • Method for synthesizing acetylenic acid by using terminal alkyne and carbon dioxide
  • Method for synthesizing acetylenic acid by using terminal alkyne and carbon dioxide
  • Method for synthesizing acetylenic acid by using terminal alkyne and carbon dioxide

Examples

Experimental program
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Effect test

Embodiment 1

[0053] A kind of method utilizing terminal alkyne and carbon dioxide to synthesize alkynoic acid, comprises the steps:

[0054] Add 4 ml of dimethyl sulfoxide, 1 mmol of phenylacetylene, and 2 mmol of cesium carbonate into the reaction tube, pump and ventilate the reaction tube 3 times, and fill with CO 2 , filled with the CO 2 The gas pressure of the rear reaction tube is 1 atmosphere, and the reaction is stirred and reacted for 24 hours under the condition of carbon dioxide atmosphere and 60 ° C, the stirring rate is 800 rpm, the stirring is stopped, cooled to room temperature, and 5 ml of sodium hydroxide of 2 moles per liter is added to the reaction solution solution, add 5 ml of water, extract 4 times with ethyl acetate, separate the layers, take the water layer, acidify the water layer with 2 moles per liter of hydrochloric acid to pH = 1, then extract with ethyl acetate, take the organic layer, the organic layer Wash with saturated brine and dry over magnesium sulfate,...

Embodiment 2

[0056] A kind of method utilizing terminal alkyne and carbon dioxide to synthesize alkynoic acid, comprises the steps:

[0057] Add 4 ml of dimethyl sulfoxide, 1 mmol of phenylacetylene, and 1.5 mmol of cesium carbonate into the reaction tube, pump and ventilate the reaction tube 3 times, and fill with CO 2 , filled with the CO 2 The gas pressure of the rear reaction tube is 1 atmosphere, and the reaction is stirred and reacted for 24 hours under the condition of carbon dioxide atmosphere and 60 ° C, the stirring rate is 800 rpm, the stirring is stopped, cooled to room temperature, and 5 ml of sodium hydroxide of 2 moles per liter is added to the reaction solution solution, add 5 ml of water, extract 4 times with ethyl acetate, separate the layers, take the water layer, acidify the water layer with 2 moles per liter of hydrochloric acid to pH = 1, then extract with ethyl acetate, separate the layers, and take the organic layer , the organic layer was washed with saturated bri...

Embodiment 3

[0059] A kind of method utilizing terminal alkyne and carbon dioxide to synthesize alkynoic acid, comprises the steps:

[0060] Add 4 ml of dimethyl sulfoxide, 1 mmol of phenylacetylene, and 2.5 mmol of cesium carbonate into the reaction tube, pump and ventilate the reaction tube 3 times, and fill with CO 2 , filled with the CO 2 The gas pressure of the rear reaction tube was 1 atmosphere, and the reaction was stirred and reacted for 24 hours under the conditions of carbon dioxide atmosphere and 60° C., the stirring rate was 800 rpm, the stirring was stopped, cooled to room temperature, the reaction liquid was added with water, extracted 4 times with ethyl acetate, and divided solution, take the water layer, and acidify the water layer to pH = 1 with 2 moles per liter of hydrochloric acid, then extract with ethyl acetate, take the organic layer, wash the organic layer with saturated brine and dry on magnesium sulfate, filter the filtrate, and reduce pressure Concentration gav...

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Abstract

The invention belongs to the field of organic synthesis, and particularly relates to a method for synthesizing acetylenic acid by using terminal alkyne and carbon dioxide. The method comprises the experimental steps that alkyne, alkali and a solvent are added into a reaction tube, the alkyne serves as a raw material, the alkali and the solvent provide a strong alkaline environment, CO2 is introduced into a reaction container to form a carbon dioxide atmosphere, heating and stirring reaction are carried out, after the reaction is finished, cooling is carried out to the room temperature, extraction and liquid separation are carried out, a water layer is acidified, then separation and purification are further carried out, and the acetylenic acid compound is obtained. The method is carried out under the conditions of low temperature and normal pressure, does not need to add a metal catalyst, is single in product and convenient to separate, good in substrate applicability and safe and simple to operate, and has potential industrial application prospects and good economic benefits.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for directly carboxylating alkyne and carbon dioxide to synthesize alkynoic acid under mild conditions. Background technique [0002] With the continuous use of fossil fuels, CO 2 The gradual increase of the content has caused the global greenhouse effect and triggered a series of climate, environmental and ecological problems (M.Ding, R.W.Flaig, H.L.Jiang, O.M.Yaghi, Chem.Soc.Rev.2019, 48, 2783-2828; T.W.A.J. Xiaoxia Chang, Energ. Environ. Sci. 2016, 9, 2177-2196; Sneddon, G.; G. Sneddon, A. Greenaway, H.H.P. Yiu, Adv. Energy Mater. 2014, 4, 1301873). At the same time, CO 2 Not only the main component of greenhouse gases, but as a kind of C with large reserves, non-toxic, cheap and easy to obtain, renewable 1 resources, it is of great significance to effectively utilize and convert them into fine chemicals with high added value (J.Artz, T.E.Müller, K.Then...

Claims

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Application Information

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IPC IPC(8): C07C51/15C07C253/30C07D333/24C07C57/42C07C57/60C07C59/64C07C59/68C07C255/57C07B41/08
CPCC07C51/15C07C253/30C07D333/24C07B41/08
Inventor 胡建强向鸽戚朝荣
Owner SOUTH CHINA UNIV OF TECH
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