Tetradentate schiff base metal complexes, metal porphyrin complexes and preparing method of polycarbonate

A technology of tetradentate Schiff bases and metal complexes, which is applied in chemical instruments and methods, magnesium organic compounds, compounds of Group 5/15 elements of the periodic table, etc., can solve the problems of polycarbonate toxicity that cannot be applied to actual industrial production, and polycarbonate Problems such as excessive metal content

Active Publication Date: 2012-07-11
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
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Problems solved by technology

However, such catalysts generally use toxic metals such as cobalt and chromium as active centers, resulting in excessive toxic metal content in the polycarbonate produced by catalytic polymerization, which has become an important obstacle for the application of polycarbonate materials in the fields of food and medical packaging. Therefore, This kind of tetradentate Schiff base cobalt complex catalysts with high activity has been unable to be applied to actual industrial production.

Method used

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  • Tetradentate schiff base metal complexes, metal porphyrin complexes and preparing method of polycarbonate
  • Tetradentate schiff base metal complexes, metal porphyrin complexes and preparing method of polycarbonate
  • Tetradentate schiff base metal complexes, metal porphyrin complexes and preparing method of polycarbonate

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preparation example Construction

[0086] The present invention also provides a kind of preparation method of polycarbonate, comprising:

[0087] Under the catalysis of the metal porphyrin complex of the formula (II), carbon dioxide and epoxide undergo a copolymerization reaction to generate polycarbonate;

[0088]

[0089] where: R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 each independently selected from hydrogen, halogen, a substituted aliphatic group, a substituted heteroaliphatic group, a substituted aryl group, a substituted heteroaryl group or a substituent of the formula (III), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 At least one of them is a substituent of formula (III):

[0090]

[0091] In the formula (III), Q is a quaternary ammonium salt, a quaternary phosphonium salt or a bulky orga...

Embodiment 1

[0098] Preparation of complex CAT-1

[0099] Add 2.16g of sodium hydride and 30ml of tetrahydrofuran into a 250ml round bottom flask, stir to dissolve and cool to 0°C. 20 ml of tetrahydrofuran solution in which 3.0 g of TBD was dissolved was slowly added dropwise to the above-mentioned round bottom flask. After the dropwise addition was completed, it was raised to room temperature, and the reaction was continued for 2 h, and 20 ml of a tetrahydrofuran solution in which 5.39 g of 2-tert-butyl-4-(4-bromobutyl)anisole was dissolved was added dropwise. After the dropwise addition was completed, it was raised to room temperature and reacted for another 20 h until the reactants were completely converted. The insoluble matter in the reaction solution was removed by filtration, and the solvent was removed under reduced pressure to obtain an orange oil. Dissolve the orange-yellow oil in a small amount of ethyl acetate, add 80ml of 2mol / L dilute hydrochloric acid, stir vigorously for ...

Embodiment 2

[0119] After dissolving 3.23g of p-bromomethylbenzaldehyde in 1800ml of chloroform, 1.088g of pyrrole was added. Add 0.6721ml BF under argon protection 3 / OEt 2 After 1 hour of reaction, 2.76 g of dichlorodicyanobenzoquinone was quickly added, and the reaction was continued for 1 hour. The solvent was removed under reduced pressure, and the obtained solid was washed with methanol until the filtrate was colorless, and a bright purple solid CPD4-a was obtained with a yield of about 51%.

[0120] Dissolve 1.4g TBD and 0.96g sodium hydride in 30ml of tetrahydrofuran at room temperature, slowly add 30ml of tetrahydrofuran solution containing 7.89g CPD4-a, after the dropwise addition, react for 48h and filter, the filtrate is vacuum-dried, and the obtained solid is used Separation by silica gel column chromatography gave 6.04 g of purple solid CPD4-b with a yield of about 62%. CPD4-b was analyzed by high-resolution electrospray mass spectrometry, and the analysis result was [C78H8...

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Abstract

The invention provides tetradentate schiff base metal complexes with formula (I) and metal porphyrin complexes with formula (II). The active centers of the two complexes are non-toxic zinc, magnesium, manganese or iron. The invention also provides a method for preparing polycarbonate by using the complexes as a catalyzer. The ligand of the two complexes contain at least one or more quaternary ammonium salt or strong sterically hindered organic base group, so the two complexes have higher catalytic activity, meanwhile the complexes have non-toxic active center metal like zinc, magnesium, manganese or iron, can effectively prevent the problem of the exceeding content of toxic metals in polycarbonate and ensure that the product does not contain toxic metal residues.

Description

technical field [0001] The invention relates to the field of catalysts, in particular to a tetradentate Schiff base metal complex, a metal porphyrin complex and a method for preparing polycarbonate. Background technique [0002] Carbon dioxide is the main gas that causes the greenhouse effect, and it is also one of the most abundant carbon sources on the earth, and it is also a cheap carbon and oxygen resource. Carbon dioxide as a carbon and oxygen resource is an important research topic in the synthesis of bulk basic chemicals, fuels and polymer materials. Among them, aliphatic polycarbonate, which is copolymerized with carbon dioxide and epoxy as raw materials under the action of a catalyst, is a fully degradable polymer material with good transparency and excellent oxygen and water barrier properties. As engineering plastics, biodegradable non-polluting materials, disposable pharmaceutical and food packaging materials, adhesives and composite materials, etc., it has wide...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00C07D487/04C07F19/00C07F9/50C07F3/02C07D213/74C07D487/22C08G64/34
Inventor 秦玉升王献红赵晓江王佛松
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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