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Method for preparing cyclic carbonate by taking NHC/ZnBr2 system as catalyst

A cyclic carbonate, catalytic preparation technology, applied in the direction of chemical instruments and methods, physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, etc., can solve the problem of production scale, single method, insufficient solution issues such as the greenhouse effect

Inactive Publication Date: 2012-10-03
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the chemical conversion method of carbon dioxide has been applied in industrial production, it is not enough to solve the greenhouse effect caused by the increasingly serious excessive emission of carbon dioxide due to the limitation of production scale and single method.

Method used

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  • Method for preparing cyclic carbonate by taking NHC/ZnBr2 system as catalyst
  • Method for preparing cyclic carbonate by taking NHC/ZnBr2 system as catalyst
  • Method for preparing cyclic carbonate by taking NHC/ZnBr2 system as catalyst

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The structure of the nitrogen heterocyclic carbene (NHC) ligand involved in the present invention is as follows:

[0028]

[0029] The preparation method is as follows:

[0030]

[0031] Synthesis of N,N'-(2,6-diisopropylphenyl)-ethylenediimine 1:

[0032] In a 100mL round bottom flask, add 2,6-diisopropylaniline (8.86g, 50mmol), 40% glyoxal (3.63g, 25mmol) and 40mL absolute ethanol, and react for 10min at room temperature, It was found that a large amount of solids were precipitated. After the reaction was continued to stir for 12 hours, it was directly suction filtered and dried under vacuum to obtain 9.32 g of the target product as a yellow solid, with a yield of 99%.

[0033] refer to figure 1 , is the hydrogen spectrum of compound 1, 1 H NMR (400MHz, CDCl 3 ): δ8.11 (s, 2H), 7.21-7.18 (m, 6H), 2.98-2.92 (m, 4H), 1.22 (d, J=6.8Hz, 24H).

[0034] Synthesis of N,N'-(2,6-diisopropylphenyl)-ethylenediamine 2:

[0035] In a 250mL round bottom flask, add Compo...

Embodiment 2

[0041] NHC / ZnBr 2 The system catalyzes the cycloaddition reaction of carbon dioxide and epoxide (1,2-epoxy-butane) to prepare the corresponding cyclic carbonate. The chemical reaction formula is:

[0042]

[0043] experiment procedure

[0044] In the glove box, weigh 2mol% (the equivalent ratio of NHC to epoxide is 0.02:1) of NHC ligand (0.15g, 0.35mmol), K 2 CO 3 (0.048g, 0.35mmol), ZnBr 2 (0.079g, 0.35mmol) in a dry 50mL flask, add a stirring bar, plug a rubber stopper to seal, then place the flask on a vacuum line to evacuate, and then insert a balloon filled with high-purity carbon dioxide on the rubber stopper , Inject 10ml of anhydrous and oxygen-free DMSO into the flask with a syringe, control the pressure at 1atm, and then inject 1,2-epoxybutane (1.5mL, 17.5mmol) into the flask, and react in an oil bath at 80°C for 24h to stop the reaction. Cool to room temperature, add 200mL of deionized water, extract with dichloromethane (3 × 20mL), dry over anhydrous magnesi...

Embodiment 3

[0048] NHC / ZnBr 2 The system catalyzes the cycloaddition reaction of carbon dioxide and epoxide (1,2-epoxy n-hexane) to prepare the corresponding cyclic carbonate, the chemical reaction formula

[0049]

[0050] experiment procedure

[0051] Weigh 2mol% NHC ligand (0.15g, 0.35mmol) in the glove box, K 2 CO 3 (0.048g, 0.35mmol), ZnBr 2 (0.079g, 0.35mmol) in a dry 50mL flask, add a stirring bar, plug a rubber stopper to seal, then place the flask on a vacuum line to evacuate, and then insert a balloon filled with high-purity carbon dioxide on the rubber stopper , Inject 10ml of anhydrous and oxygen-free DMSO into the flask with a syringe, and then inject 1,2-epoxy-n-hexane (2.1mL, 17.5mmol) into the flask, react in an oil bath at 80°C for 24h to stop the reaction. Cool to room temperature, add 200mL of deionized water, extract with dichloromethane (3 × 20mL), dry over anhydrous magnesium sulfate, then obtain the crude product by rotary evaporation of the filtrate obtained...

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Abstract

The invention discloses a method for preparing a cyclic carbonate by taking a NHC / ZnBr2 system as a catalyst, which comprises the step of catalyzing epoxide and carbon dioxide to synthesize the corresponding cyclic carbonate by cycloaddition by taking the NHC / ZnBr2 system consisting of N, N'-(2,6-diisopropylphenyl)-imidazoline hydrochloride, potassium carbonate and zinc bromide as the catalyst, wherein the reaction pressure is 0.1 MPa, the reaction temperature is 80 DEG C, the reaction time is 24 h and the reaction solvent is DMSO. The synthesis method has the characteristics of mild reaction condition, high catalytic activity, single product, simplicity in purification operation and the like.

Description

technical field [0001] The present invention relates to a method for the preparation of carbonates by cycloaddition of epoxides and carbon dioxide, especially NHC / ZnBr 2 System catalyzed method for preparing cyclic carbonate. Background technique [0002] carbon dioxide (CO 2 ) is one of the most widely distributed, abundant, and cheapest carbon resources on the earth. It is estimated that CO 2 and carbon reserves in the form of carbonates are about 10 16 Ton. In addition, CO 2 It also has many advantages such as stable properties, non-toxic, non-corrosive, flame retardant, and easy to handle. Using the limited and non-renewable petrochemical resources as a substitute for Cl synthesis to obtain useful compounds through chemical transformation has always been one of the green chemistry topics that has attracted much attention, and has important application value and theoretical research significance. [0003] Currently, CO 2 The chemical utilization of CO2 has begun to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/36B01J31/26
Inventor 曹昌盛史延慧刘祥
Owner XUZHOU NORMAL UNIVERSITY
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