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Multifunctional metalloporphyrin complex and preparation method thereof, and preparation method of polycarbonate

A metalloporphyrin and complex technology, applied in the preparation of polycarbonate, multifunctional metalloporphyrin complexes and the field of preparation thereof, can solve the problems of many cyclic by-products, difficult to control the composition ratio of polymer products, insufficient activity and the like , to achieve the effect of high catalytic activity

Active Publication Date: 2022-01-14
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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Problems solved by technology

[0003] Since Inoue realized the copolymerization of carbon dioxide and propylene oxide for the first time in 1969, people have studied various catalytic systems, but these catalysts have more or less insufficient activity, and there are many cyclic by-products in the polymerization process, and the composition ratio of polymerization products is difficult to control and other shortcomings

Method used

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  • Multifunctional metalloporphyrin complex and preparation method thereof, and preparation method of polycarbonate
  • Multifunctional metalloporphyrin complex and preparation method thereof, and preparation method of polycarbonate
  • Multifunctional metalloporphyrin complex and preparation method thereof, and preparation method of polycarbonate

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preparation example Construction

[0071] The present invention provides a kind of preparation method of polyfunctional metalloporphyrin complex described in above-mentioned technical scheme, comprises the following steps:

[0072] reacting the multifunctional ligand with the structure of formula III with the organic compound containing M and X groups to obtain the multifunctional metalloporphyrin complex with the structure of formula I;

[0073] The M is magnesium, aluminum, zinc, chromium, manganese, iron, cobalt, titanium, yttrium, nickel or ruthenium;

[0074] The X is halogen, -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 oxyanion, 3,5-dichlorophenol oxyanion, 3,5-difluorophenol oxyanion, 3,5-di-trifluoromethyl Phenol oxyanion or pentafluorophenol oxyanion;

[0075]

[0076] R' is a s...

preparation example 1

[0095] Add 15g (120mmol) of 3-hydroxybenzaldehyde, 68.1g (370mmol) of 4-bromobenzaldehyde and 33g (490mmol) of pyrrole into 500mL of propionic acid, heat up to about 130°C, reflux for 1.5h, and cool down after the reaction To room temperature, the reaction solution was concentrated to 200 mL, cooled overnight in the refrigerator after adding methanol, and the resulting product was filtered through silica gel column chromatography (CHCl 3 / CH 3 OH) to obtain the product EL1 with a yield of about 7.8%. 1 H-NMR (CDCl 3 , ppm): 8.9, 8.8, 8.1, 7.8, 7.2, -2.8. High-resolution electrospray mass spectrometry analysis, the analysis result is [C44H27Br3N4O]: 863.97, found: 863.86;

[0096] Under the protection of nitrogen, dissolve 2g (2.3mmol) of EL1 in 20mL of anhydrous THF, drop in 0.26g (2.5mmol) of methacryloyl chloride and 0.25g (2.5mmol) of triethylamine at low temperature, and mix thoroughly The above mixture was reacted at room temperature for 12h. After the reaction, the ...

preparation example 2

[0101]Under nitrogen protection, 1g (1.07mmol) EL2, 0.17g (1.07mmol) dimethylaminoethyl methacrylate (DMAEMA), 8.78mg (5.35×10 -2 mmol) azobisisobutyronitrile (AIBN) and 38.98mg (0.107mmol) RAFT reagent (DDMAP) were dissolved in 20mL of anhydrous THF, and after freezing-pumping-thawing three times to remove oxygen, the above mixture was heated to 70°C for 36h . After the reaction was completed, the reaction vessel was quenched and thawed in liquid nitrogen, and the precipitation was dissolved and precipitated repeatedly through the dichloromethane / ether system, and 0.72 g of multifunctional porphyrin ligand EL4 was obtained by isolation. 1 H NMR NMR and GPC tests show that m is 9 and n is 10;

[0102] Under the protection of nitrogen, the above ligand EL4 was dissolved in dichloromethane, and AlEt was added dropwise 2 Cl (diethylaluminum chloride), stirred at room temperature for 2 h. The obtained product was purified by column chromatography and dried to obtain the desired...

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Abstract

The invention provides a multifunctional metalloporphyrin complex and a preparation method thereof, and a preparation method of polycarbonate. The complex has a structure as shown in a formula I. According to the invention, the porphyrin complex is prepared by carrying out random copolymerization on a porphyrin monomer and a specific organic alkali monomer, and the scheme can be used for rapidly preparing the porphyrin complex containing a plurality of active centers. Compared with the prior art, interaction between the active centers and organic alkali and even the catalytic performance can be adjusted by changing the substituent group of the porphyrin monomer, a ratio of the porphyrin monomer to the organic alkali monomer and the type of the organic alkali. The produced catalyst shows very high catalytic activity, product selectivity and high-temperature stability when catalyzing copolymerization of carbon dioxide and alkylene oxide.

Description

technical field [0001] The invention belongs to the technical field of catalysts, and in particular relates to a polyfunctional metal porphyrin complex, a preparation method thereof, and a polycarbonate preparation method. Background technique [0002] In industrial production, carbon dioxide is a non-toxic and harmless carbon-oxygen resource with abundant reserves while serving as a greenhouse gas. The polycarbonate prepared by alternating copolymerization with epoxide is fully degradable, and it also provides a good substitute for the increasingly scarce non-renewable resources such as petroleum. It is more important now that the "carbon neutral" strategy is getting more and more attention. It is an important means of carbon dioxide utilization. Not only that, the obtained polycarbonate has excellent transparency and excellent barrier properties, and can be used as engineering plastics, disposable medicine and food packaging materials, adhesives, etc. [0003] Since Inou...

Claims

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Application Information

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IPC IPC(8): C08F220/34C08F8/42C08G64/34
CPCC08F8/42C08F220/34C08G64/34
Inventor 张若禹刘顺杰曹瀚王献红
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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