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Tetradentate pyridyl Schiff base metal complexes, methods for their preparation and methods for cyclic carbonates

A technology of tetradentate pyridine-based mats and metal complexes, applied in the direction of organic compound/hydride/coordination complex catalysts, magnesium organic compounds, zinc organic compounds, etc., can solve the problem of long reaction time, low selectivity, and reaction conditions Harshness and other problems, to prevent the toxic metal content from exceeding the standard, and to facilitate the promotion and application of the effect

Active Publication Date: 2016-03-30
中科应化(长春)科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Heterogeneous catalysts are easier to remove from the product, but they have problems such as low catalytic activity, low selectivity, long reaction time and harsh reaction conditions
In order to realize the cycloaddition reaction of carbon dioxide and epoxides under milder conditions, the prior art has developed homogeneous catalysts, such as metal complexes, especially tetradentate Schiff bases with cobalt, chromium, etc. as active centers Metal complexes show high catalytic activity under milder reaction conditions, but their selectivity is low, and by-products such as polycarbonate will be formed in the cycloaddition reaction product

Method used

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  • Tetradentate pyridyl Schiff base metal complexes, methods for their preparation and methods for cyclic carbonates
  • Tetradentate pyridyl Schiff base metal complexes, methods for their preparation and methods for cyclic carbonates
  • Tetradentate pyridyl Schiff base metal complexes, methods for their preparation and methods for cyclic carbonates

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preparation example Construction

[0101] The present invention also provides a preparation method of a tetradentate pyridyl Schiff base metal complex having a structure shown in formula (II), comprising the following steps:

[0102] reacting the first intermediate product obtained by the above technical scheme with a reducing agent in a solvent to obtain a second intermediate product;

[0103] The second intermediate product is reacted with a metal chloride in an organic solvent to obtain a tetradentate pyridyl Schiff base metal complex having a structure represented by formula (II).

[0104] In the present invention, the first intermediate product is preferably dissolved, and then the obtained first intermediate product solution is cooled, and then a reducing agent is added therein, stirred, and reacted to obtain a second intermediate product. In the present invention, the cooling temperature is preferably -5°C to 5°C, more preferably -2°C to 2°C, most preferably 0°C.

[0105] In the present invention, the r...

Embodiment 1

[0127] Add 5.63g of 2-pyridinecarbaldehyde and 3.00g of 1,2-cyclohexanediamine into 50mL of anhydrous methanol, stir and react the resulting mixed solution at room temperature for 4h, remove the solvent in the reaction solution in vacuo, and dissolve the obtained solid with diethyl ether The reaction product was obtained after washing.

[0128] The present invention carries out structural identification of the reaction product obtained, and the results show that the reaction product obtained in this embodiment has a structure shown in formula (XX);

[0129] The present invention calculates that the yield of the compound represented by the formula (XX) in this example is 75%.

[0130]

[0131] 2.00 g of the compound represented by the formula (XX) was dissolved in dichloromethane, and excess ferric chloride was added thereto. The reaction was stirred overnight at room temperature and filtered. Diethyl ether was added to produce precipitation, and the tetradentate pyridyl S...

Embodiment 2

[0134] Dissolve 2.00 g of the compound of the formula (XX) obtained in Example 1 in 25 mL of anhydrous methanol, cool the obtained solution of the compound of the formula (XX) to 0° C., and slowly add 2.59gNaBH 4 , the reaction system was warmed up to room temperature and continued to stir for 12 h. Remove the solvent in the reaction solution in vacuo, add 100mL dichloromethane and 50mL water to the obtained solid for extraction, collect the organic phase; extract the water phase with 100mL dichloromethane for 2 times, combine the organic phases with anhydrous magnesium sulfate Drying, filtration to remove magnesium sulfate, and removal of solvent in vacuo afforded the reaction product.

[0135] The present invention carries out structural identification of the reaction product obtained, and the results show that the reaction product obtained in this embodiment has a structure shown in formula (XXI);

[0136] The present invention calculates that the yield of the compound ha...

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Abstract

The invention provides a quadridentate pyridyl schiff base metal complex with a structure as shown in a formula (I) or (II), a preparation method of the metal complex as well as a preparation method of cyclic carbonate. The cyclic carbonate is prepared by cycloaddition of carbon dioxide and epoxide in the presence of the quadridentate pyridyl schiff base metal complex and a catalyst promoter, namely quaternary ammonium salt. During cycloaddition, the quadridentate pyridyl schiff base metal complex as a main catalyst has high catalytic activity, thereby enhancing the reaction rate of cycloaddition, and also has good product selectivity, thereby enhancing the yield of cyclic carbonate in a product. Experiment results show that the product selectivity of the quadridentate pyridyl schiff base metal complex is higher than 99% and cycloaddition singly generates cyclic carbonate.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a tetradentate pyridyl Schiff base metal complex, a preparation method thereof and a cyclic carbonate method. 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 d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/22C07F15/02C07F3/02C07F3/06C07F13/00C07D317/36
Inventor 盛兴丰秦玉升王献红王佛松
Owner 中科应化(长春)科技有限公司
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