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Mononuclear aluminum and binuclear aluminum compounds based on biphenyl skeleton Salen ligand and preparation method and application thereof

An aluminum compound and skeleton technology, applied in the application field of lactone polymerization, can solve the problem of low catalytic activity of catalysts, and achieve the effects of narrow molecular weight distribution, stable properties, high catalytic activity and selectivity

Inactive Publication Date: 2013-04-17
EAST CHINA UNIV OF SCI & TECH
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  • Abstract
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Problems solved by technology

[0005] In conclusion, significant progress has been made in the design of metal complex catalysts to catalyze the ring-opening polymerization of lactide, and the Salen aluminum complex is currently the only catalyst with high isotactic selectivity for the ring-opening polymerization of racemic lactide, but The catalytic activity of such catalysts is very low, so it is still necessary to modify existing complex catalysts or design and synthesize new complexes to obtain catalysts with high activity and high selectivity for ring-opening polymerization such as racemic lactide

Method used

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  • Mononuclear aluminum and binuclear aluminum compounds based on biphenyl skeleton Salen ligand and preparation method and application thereof
  • Mononuclear aluminum and binuclear aluminum compounds based on biphenyl skeleton Salen ligand and preparation method and application thereof
  • Mononuclear aluminum and binuclear aluminum compounds based on biphenyl skeleton Salen ligand and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Synthesis of Ligand L1

[0039] Add 1.79g (8.4mmol) 2,2'-diamino-6,6'-dimethylbiphenyl and 2.53g (10.0mmol) 2,4-dimethyl salicylaldehyde in a 100mL eggplant-shaped bottle, and then Add 30 mL of absolute ethanol to dissolve it. The solution was dark red, heated to ethanol reflux with an oil bath, and reacted for 16 hours. After the reaction was completed, the oil bath was removed, and the reaction solution was slowly cooled to room temperature, and orange-red crystals were precipitated. The reaction solution was filtered, the filter cake was washed with ethanol, and dried to obtain orange-red crystal L1 (3.56 g, yield: 88.5%).

[0040]

[0041] 1 H NMR (CDCl 3 , 400MHz): δ12.12(s, 2H, Ar-OH), 8.33(s, 2H, N=C-H), 7.33(t, 2H, J=7.6Hz, Ar-H), 7.22(d, 2H, J=7.6Hz, Ar-H), 7.02(d, 2H, J=7.6Hz, Ar-H), 6.94(s, 2H, Ar-H), 6.83(s, 2H, Ar-H), 2.22( s, 6H, Ar-CH 3 ), 2.12(s, 6H, Ar-CH 3 ), 2.05(s, 6H, Ar-CH 3 ).Anal.Calcd.for:C 32 h 32 o 2 N 2 : C, 80.64; H, 6.77; N,...

Embodiment 2

[0043] Synthesis of Ligand L2

[0044] Add 1.06g (5.0mmol) 2,2'-diamino-6,6'-dimethylbiphenyl, 1.93g (10.0mmol) 2-tert-butyl-4 methylsalicylaldehyde in a 100mL bottle, and add 30mL without Water and ethanol were heated in an oil bath to reflux the ethanol and reacted for 16 hours. After the reaction was completed, the oil bath was removed, and the reaction solution was slowly cooled to room temperature. It was found that needle-shaped yellow crystals were precipitated in ethanol. The reaction solution was filtered,

[0045] The filter cake was washed with ethanol and dried to obtain yellow crystal L2 (1.8 g, yield: 64.3%).

[0046]

[0047] 1 H NMR (CDCl 3 , 400MHz): δ12.80(s, 2H, Ar-OH), 8.35(s, 2H, N=C-H), 7.30(t, 2H, J=7.6Hz, Ar-H), 7.20(d, 2H, J=7.6Hz, Ar-H), 7.06(d, 2H, J=2.0Hz, Ar-H), 7.01(d, 2H, J=8.0Hz, Ar-H), 6.84(d, 2H, J= 2.0Hz, Ar-H), 2.22(s, 6H, Ar-CH 3 ), 2.07(s, 6H, Ar-CH 3 ), 1.30(s, 18H, Ar- t Bu).Anal.Calcd.for: (contains 0.33AcOEt)C 38 h 44 o ...

Embodiment 3

[0049] Synthesis of Ligand L3

[0050] Add 1.06g (5.0mmol) 2,2'-diamino-6,6'-dimethylbiphenyl, 3.305g (10.0mmol) 2,4-dipentyl salicylaldehyde, 30mL anhydrous Ethanol, heated with an oil bath to reflux the ethanol, and reacted for 16 hours. After the reaction was completed, the oil bath was removed, and the reaction solution was slowly cooled to room temperature. It was found that needle-shaped yellow crystals were precipitated in ethanol. The reaction solution was filtered, the filter cake was washed with ethanol, and dried with B to obtain yellow crystal L3 (3.9 g, yield: 84.8%).

[0051]

[0052] 1 H NMR (CDCl 3 , 400MHz): δ12.54(s, 2H, Ar-OH), 8.09(s, 2H, N=C-H), 7.30(d, 2H, J=8.0Hz, Ar-H), 7.24(m, 8H, Ar-H), 7.16(m, 8H, Ar-H), 7.06(m, 8H, Ar-H), 6.95(d, 2H, J=2.0Hz, Ar-H), 6.81(d, 2H, J =8.0Hz, Ar-H), 1.90(s, 6H, Ar-CH 3 ), 1.68(s, 12H, cumyl-CH 3 ), 1.52(s, 6H, cumyl-CH 3 ), 1.50(s, 6H, cumyl-CH 3 ).Anal.Calcd.for:C 64 h 64 o 2 N 2 : C, 86.06; H, 7.22; N, ...

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Abstract

The invention discloses mononuclear aluminum and binuclear aluminum compounds based on biphenyl skeleton Salen ligand, a preparation method of the mononuclear aluminum and binuclear aluminum compounds, and an application of the mononuclear aluminum and binuclear aluminum compounds in ring-opening polymerization of catalytic internal ester. The preparation method of the mononuclear aluminum and binuclear aluminum compounds based on the biphenyl skeleton Salen ligand comprises the following steps of: adding a ligand compound to directly react with aluminum alkyl in an organic medium, filtering, concentrating and recrystallizing to obtain a target compound; and adjusting the mole ratio of the ligand compound to the aluminum alkyl, thus obtaining the mononuclear aluminum or binuclear aluminum compound respectively. The mononuclear aluminum and binuclear aluminum compounds based on the biphenyl skeleton Salen ligand are efficient catalysts for ring-opening polymerization of internal ester, and can be used for polymerization of lactide, epsilon-caprolactone and the like; and the source of raw materials is wide, the synthesis is easy, the product yield is high, the performance is stable, the catalytic activity is high, a polymer with high molecular weight can be obtained, and the requirements of industrial departments can be met. The structural formulae of the compounds are as shown in the specification.

Description

technical field [0001] The invention relates to a class of biphenyl skeleton Salen ligand mononuclear and binuclear aluminum compounds and the application of such compounds in lactone polymerization. Background technique [0002] Polyolefin materials are high-quality and cheap, which brings great convenience to people's production and life. However, with the depletion of oil resources and the rising international oil prices, it is easy to cause environmental pollution. Its development is inevitably affected. limit. Aliphatic lactone polymers can be used as a substitute for polyolefin materials due to their degradability, biocompatibility and good mechanical processing properties, as well as in biomedical fields, such as sutures for surgical operations Threads, biocompatible prosthetics, and drug-controlled release carriers, among other materials. Currently, the monomers used in lactone polymerization research are mainly lactide and caprolactone, and the raw material of lac...

Claims

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Application Information

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IPC IPC(8): C07F5/06C08G63/84C08G63/08
Inventor 马海燕葛纪累
Owner EAST CHINA UNIV OF SCI & TECH
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