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Method for synthesizing cyclic carbonate and derivatives thereof

A technology of cyclic carbonates and synthesis methods, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc., can solve the problems of high metal residues and raw material costs, and limited metal catalysts Application, narrow applicability of catalysts, etc., to achieve good catalytic effect, low cost of raw materials, and convenient purification

Active Publication Date: 2021-02-26
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The catalysts currently reported in the literature are mainly divided into organic catalysts and metal catalysts. Metal catalysts are often highly active, but their metal residues and raw material costs are high, and they are not recyclable, which greatly limits the application of metal catalysts.
Although organic catalysts include quaternary ammonium salts, quaternary phosphonium salts, and some imidazolium salts, etc., most of these catalysts have narrow applicability, and most of them require harsh reaction conditions (such as high temperature and pressure, anhydrous and oxygen-free), which are fundamentally Added additional CO 2 emission

Method used

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  • Method for synthesizing cyclic carbonate and derivatives thereof
  • Method for synthesizing cyclic carbonate and derivatives thereof
  • Method for synthesizing cyclic carbonate and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Weigh 0.244g (2mmol) of nicotinamide, add it into a 25mL pincer bottle, measure 10mL of methanol into it, shake and shake well. Then absorb 0.187mL (3mmol) of iodomethane, add it into the reaction bottle and mix well, and stir the reaction at room temperature for 2h. After the reaction was complete, a yellow solid was obtained by filtration under reduced pressure, and the obtained solid was recrystallized with 2 mL of methanol to obtain 0.32 g of a yellow crystal. That 1 HNMR spectrum such as figure 1 shown. The deuterium reagent used is DMSO-d 6 , the chemical shift is 2.5, the ratio of peak area is 1:1:1:1:2:3, which is in line with the expectation, and there is no obvious miscellaneous peak. 1 HNMR analysis can confirm that the structure of the catalyst (1) is correct.

Embodiment 2

[0056] Weigh 0.488g (4mmol) of nicotinamide, add it into a 50mL pincer bottle, measure 20mL of methanol into it, shake and shake well. Then absorb 1.07 mL (6 mmol) of iodo-n-octane, add it into the reaction bottle and mix evenly, and stir the reaction at 60° C. for 12 h. After the reaction is complete, low-pressure rotary steaming to obtain a yellow oily liquid, the resulting liquid is removed by column chromatography (ethyl acetate EA as the mobile phase) to remove unreacted nicotinamide, then rinsed directly with methanol, low-pressure rotary steaming, and oven-dried at 60 ° C Overnight, 0.94 g of a white solid was obtained. That 1 HNMR spectrum such as figure 2 shown. The deuterated reagent used is CDCl 3 , the chemical shift is 7.26, the ratio of peak area is 1:1:1:1:1:1:2:2:10:3, which is in line with the expectation, and there is no obvious miscellaneous peak. 1 HNMR analysis can confirm that the structure of the catalyst (2) is correct.

Embodiment 3

[0058] React with nicotinamide (488.4 mg, 4.0 mmol), 1-iodooctane (1.07 mL, 6.0 mmol), benzoic acid (73.2 mg, 0.6 mmol) and p-xylene (5 mL). The reaction mixture was stirred at 130°C for 8 hours. After cooling to room temperature, the resulting solution mixture was diluted with ethyl acetate (10 mL). The reaction mixture was purified by silica gel column chromatography to obtain the desired product (894.8 mg, 89%). The resulting product (502.7 mg, 2 mmol) was reacted with iodomethane (249 μL, 4.0 mmol). The reaction mixture was purified by column chromatography on silica gel to give the product as a colorless solid (322.5 mg, 41%). That 1 HNMR spectrum such as image 3 shown. The deuterated reagent used is CDCl 3 , its chemical shift is 7.26, and the ratio of peak area is 1:1:1:1:1:3:2:2:10:3, which is in line with the expectation, and there is no obvious miscellaneous peak. 1 HNMR analysis can confirm that the structure of the catalyst (3) is correct.

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Abstract

The invention belongs to the field of organic synthesis, and particularly relates to a method for synthesizing cyclic carbonate and derivatives thereof, which comprises the following step of: reactingan epoxy compound shown in a formula I with carbon dioxide under the catalysis of a catalyst shown in a formula II to obtain a target product. The product prepared by the method has the advantages ofhigh yield, high purity, low catalyst cost and mild synthesis conditions, and the obtained product has no metal residue.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing cyclic carbonates and derivatives thereof. Background technique [0002] In recent years, carbon dioxide (CO 2 ) is causing many worldwide problems such as global warming, and the conventional carbon cycle in nature is far from being able to bear the high concentration of CO in the atmosphere. 2 (≥400ppm), so the use of chemical methods to fix CO 2 The synthesis of high value-added chemicals has attracted more and more attention. However, CO 2 The chemical properties are extremely stable (Δ f H°=-394kJ / mol), so it is necessary to find a raw material with more active chemical properties to activate CO 2 . In addition, the source of this raw material should be abundant and the price should be low, and the resulting product should have certain industrial value. Epoxides almost completely meet the above characteristics, and the specific reaction formu...

Claims

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Application Information

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IPC IPC(8): C07D317/36B01J31/02
CPCC07D317/36B01J31/0284
Inventor 郭凯高罗玉李振江周怡颜蕊陈恺童昊颖李勇强
Owner NANJING UNIV OF TECH
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