A kind of preparation method of cyclic carbonate

A technology of cyclic carbonate and cyclization reaction, which is applied in the direction of chemical instruments and methods, organic compound/hydride/coordination complex catalyst, catalytic reaction, etc., can solve the problem of no cyclic carbonate, etc., to prevent poisonous The metal content exceeds the standard, which is conducive to the effect of popularization and application

Active Publication Date: 2017-03-29
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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However, there are no reports and patents on the preparation of cyclic carbonates

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  • A kind of preparation method of cyclic carbonate
  • A kind of preparation method of cyclic carbonate
  • A kind of preparation method of cyclic carbonate

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[0029] The invention provides a kind of preparation method of cyclic carbonate, comprises the following steps:

[0030] Under the action of the main catalyst and the co-catalyst, the carbon dioxide and the epoxide are subjected to a cyclization reaction to obtain a cyclic carbonate;

[0031] The main catalyst is a metal porphyrin complex, and the metal porphyrin complex has a structure shown in formula I:

[0032]

[0033] In formula I, the R 1 , R 2 and R 3 independently selected from hydrogen, halogen, aliphatic, substituted aliphatic, substituted heteroaliphatic, aryl, substituted aryl, or substituted heteroaryl;

[0034] The M is a metal element;

[0035] n=0 or 1;

[0036] The Y is a halogen group, -NO 3 、CH 3 COO-, CCl 3 COO-, CF 3 COO-, ClO 4 -, BF 4 -, BPh 4 -, -CN, -N 3 , p-toluate, p-toluenesulfonate, o-nitrophenol oxyanion, p-nitrophenol oxyanion, m-nitrophenol oxyanion, 2,4-dinitrophenol oxyanion, 3,5 -Dinitrophenol oxyanion, 2,4,6-trinitrophenol o...

Embodiment 1

[0111] at 25°C, N 2 Under protection, add 800mL dry dichloromethane, 2.8g 4-chlorobenzaldehyde (20mmol), 1.4mL pyrrole (20mmol) into a 1000mL round-bottomed three-neck flask, stir until the solid is completely dissolved, then add 3.7mL trifluoroacetic acid (50mmol, 2.5eq) and stirred for 1h, then added 9.08g DDQ (2.3-dichloro-5,6-dicyano-1,4-benzoquinone) and stirred for 1h, filtered the above liquid under reduced pressure, and distilled off the solvent under reduced pressure , the resulting crude product is separated by chromatographic column [stationary phase: Al2O3; mobile phase: methylene chloride / petroleum ether (volume ratio)=2:1], to obtain four (4-chlorophenyl) porphyrin, product conversion Rate 20.8%; The present invention carries out proton nuclear magnetic resonance spectrum test to the tetrakis (4-chlorophenyl) porphyrin that obtains, and analysis result is: 1 H NMR (300MHz, CDCl 3 ), δ: 8.83(s, 8H), 8.12(d, J=9.0Hz, 8H), 7.78(d, J=9.0Hz, 8H), -2.87(s, 2H); (4-c...

Embodiment 2

[0117] at 25°C, N 2 Under protection, add 800mL of dry dichloromethane, 3.7g of 4-bromobenzaldehyde (20mmol), and 1.4mL of pyrrole (20mmol) into a 1000mL round-bottomed three-neck flask, stir until the solid is completely dissolved, then add 3.7mL of trifluoroacetic acid ( 50mmol, 2.5eq) and stirred for 1h, then added 9.08g DDQ (2.3-dichloro-5,6-dicyano-1,4-benzoquinone) and stirred for 1h. The above liquid was filtered under reduced pressure, the solvent was distilled off under reduced pressure, and the obtained crude product was separated by chromatographic column [stationary phase: aluminum oxide; mobile phase: dichloromethane / petroleum ether (volume ratio)=2:1] to obtain four (4-Bromophenyl) porphyrin, the product conversion rate is 19.5%. 1 HNMR (300MHz, CDCl 3 ), δ: 8.84(s, 8H), 8.06(d, J=9.0Hz, 8H), 7.91(d, J=9.0Hz, 8H), -2.86(s, 2H); (4-bromophenyl) porphyrin has structure shown in formula XIV:

[0118]

[0119] at 25°C, N 2 Add 20mL of dry dichloromethane and ...

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Abstract

The invention provides a preparation method of a cyclic carbonate, comprising the following steps: under the action of a main catalyst and a cocatalyst, carbon dioxide and an epoxide are subjected to a cyclization reaction to obtain a cyclic carbonate; The main catalyst is a metal porphyrin complex, and the metal porphyrin complex has a structure shown in formula I; the co-catalyst is one or more of quaternary ammonium salts, quaternary phosphorus salts and organic bases. Compared with the prior art, the metalloporphyrin complex can be used as a catalyst to catalyze the cyclization reaction of carbon dioxide and epoxide, and the metalloporphyrin complex exhibits extremely high catalytic activity as a main catalyst. In addition, during the cyclization reaction, the metalloporphyrin complex as the main catalyst has high selectivity to the reaction product, which inhibits the formation of polycarbonate and increases the content of cyclic carbonate in the product; the metalloporphyrin The morphine complexes can be recycled and reused while maintaining high catalytic activity.

Description

technical field [0001] The invention relates to the technical field of organic compound synthesis, in particular to a preparation method of a cyclic carbonate. Background technique [0002] Since its birth in the 1930s, cyclic carbonate chemistry has become a subject of increasing interest to chemists. Cyclic carbonate is a very important chemical intermediate, which can obtain high molecular weight polycarbonate by ring-opening polymerization; it is also an important chemical product, which has good biodegradability and solubility, and is a good cleaning electrode It can be used as cosmetic additives, food additives, electrolytes for high-energy density batteries and capacitors, and metal extractants. [0003] The synthesis methods of cyclic carbonate mainly include phosgene method, transesterification method and cycloaddition reaction of carbon dioxide and epoxide. Among them, the cycloaddition reaction of carbon dioxide and epoxide is carried out with carbon dioxide and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/36C07D317/38B01J31/22
CPCB01J31/1805B01J35/0006B01J2231/341B01J2531/025B01J2531/26B01J2531/31B01J2531/842C07D317/36C07D317/38
Inventor 秦玉升郭洪辰王献红王佛松
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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