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Method for preparing cyclic carbonate by immobilizing CO2 under catalysis of organic boric acid

A technology of phenylboronic acid and carbon dioxide, applied in the direction of organic chemistry, etc., can solve the problems of low catalytic efficiency of non-metallic catalysts, metal residue hazards, restricted development and other problems, and achieve the effects of strong utilization value, simple operation and easy raw materials.

Inactive Publication Date: 2021-06-18
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] CO 2 As a recyclable C1 structural unit that exists in large quantities in nature, its effective utilization is of great significance. Currently, about CO 2 The most studied is to use the reaction of epoxy compounds to generate carbonates to achieve its fixation, but most of them use metal catalysts, which may cause human beings to face the hazards of metal residues, while some non-metallic Catalysts are also limited in their development due to their low catalytic efficiency.

Method used

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  • Method for preparing cyclic carbonate by immobilizing CO2 under catalysis of organic boric acid
  • Method for preparing cyclic carbonate by immobilizing CO2 under catalysis of organic boric acid
  • Method for preparing cyclic carbonate by immobilizing CO2 under catalysis of organic boric acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] The preparation of compound shown in embodiment 1, formula I-a

[0072]

[0073] according to figure 1 Shown synthetic route prepares the compound shown in formula I-a, concrete operation is as follows:

[0074] At room temperature, add phenylboronic acid (0.0024g, 0.02mmol), tetrabutylammonium bromide (0.0064g, 0.02mmol), formula IV-a propylene oxide (0.1162g, 2.0mmol) in the reaction tube, at room temperature Stir to make it dissolve, then move to a high-pressure reactor filled with carbon dioxide (10bar), stir at 80°C for 12 hours, concentrate by rotary evaporation, and purify by silica gel column chromatography, the yield is 73%.

[0075] The results of structural confirmation are as follows: 1 H NMR (300MHz, CDCl 3 ,ppm)δ4.93-4.78(m,1H),4.55(dd,J=8.4,7.5Hz,1H),4.02(dd,J=7.2,8.1Hz,1H),1.50(d,J=6.3Hz ,3H); 13 C NMR (100MHz, CDCl 3 , ppm) δ155.2, 73.7, 70.8, 19.5.

[0076] The compound synthesized through structural identification is indeed the target compou...

Embodiment 2

[0077] The preparation of compound shown in embodiment 2, formula I-b

[0078]

[0079] according to figure 2 The shown synthetic route prepares the compound shown in formula I-b, concrete operations are as follows:

[0080] At room temperature, add phenylboronic acid (0.0024g, 0.02mmol), tetrabutylammonium bromide (0.0064g, 0.02mmol), formula IV-b 1,2-epoxybutane (0.1442g, 2.0mmol) into the reaction tube ), stirred at room temperature to dissolve, then moved to an autoclave and filled with carbon dioxide (10bar), stirred at 80°C for 12 hours, concentrated by rotary evaporation, purified by silica gel column chromatography, and the yield was 81%.

[0081] The results of structural confirmation are as follows: 1 H NMR (500MHz, CDCl 3 ,ppm)δ4.73-4.65(m,1H),4.55(dd,J=8.0,8.5Hz,1H),4.10(dd,J=7.5,8.5Hz,1H),1.90-1.71(m,2H) ,1.03(t,J=7.5Hz,3H); 13 CNMR (125MHz, CDCl 3 , ppm) δ155.3, 78.2, 69.1, 26.9, 8.5.

[0082] The compound synthesized through structural identification ...

Embodiment 3

[0083] The preparation of the compound shown in embodiment 3, formula I-c

[0084]

[0085] according to image 3 The shown synthetic route prepares the compound shown in formula I-c, concrete operations are as follows:

[0086] At room temperature, add phenylboronic acid (0.0024g, 0.02mmol), tetrabutylammonium bromide (0.0064g, 0.02mmol), formula IV-c butyl oxirane (0.2003g, 2.0mmol) in the reaction tube, at room temperature Stir under low pressure to make it dissolve, then move to a high-pressure reactor and fill it with carbon dioxide (10bar), stir at 80°C for 12 hours, concentrate by rotary evaporation, and purify by silica gel column chromatography, the yield is 90%.

[0087] The results of structural confirmation are as follows: 1 H NMR (400MHz, CDCl 3 ,ppm)δ4.78-4.67(m,1H),4.54(dd,J=8.0,8.4Hz,1H),4.08(dd,J=7.6,8.0Hz,1H),1.87-1.75(m,1H) ,1.75-1.64(m,1H),1.52-1.31(m,4H),0.93(t,J=6.8Hz,3H); 13 C NMR (100MHz, CDCl 3 , ppm) δ155.3, 77.2, 69.5, 33.6, 26.5, 22.3, 13.9...

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Abstract

The invention discloses a synthesis method for synergistically catalyzing carbon dioxide immobilization through weak Lewis acid phenylboronic acid and tetrabutylammonium bromide. According to the method, CO2 is immobilized by epoxide, and a cyclic carbonate product is generated. The method comprises the following step: under the concerted catalysis of phenylboronic acid and tetrabutylammonium bromide, performing reaction on epoxide as shown in a formula IV, a formula V or a formula VI and carbon dioxide to respectively obtain a cyclic carbonate product as shown in a formula I, a formula II or a formula III. According to the method, raw materials are convenient and easy to obtain, reaction conditions are mild, operation is easy and convenient, and the yield can reach 97%.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to the reaction of organic boric acid on CO in a non-metallic catalytic system. 2 fixation and conversion to the cyclic carbonate product. Background technique [0002] CO 2 As a recyclable C1 structural unit that exists in large quantities in nature, its effective utilization is of great significance. Currently, about CO 2 The most studied is to use the reaction of epoxy compounds to generate carbonates to achieve its fixation, but most of them use metal catalysts, which may cause human beings to face the hazards of metal residues, while some non-metallic Catalysts are also limited by their low catalytic efficiency. [0003] Therefore, the development of a metal-free catalyst for efficient CO fixation 2 method has important practical significance. Contents of the invention [0004] The purpose of the present invention is to utilize simple and easy-to-ob...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/36C07D317/44C07D493/04
CPCC07D317/36C07D317/44C07D493/04
Inventor 杜海峰陈晶晶冯向青
Owner INST OF CHEM CHINESE ACAD OF SCI