Novel bridged beta-diimido binuclear aluminum compound and preparation method and use thereof

A technology of aluminum compounds and diimines, which is applied in the field of new bridged β-diimine binuclear aluminum compounds, can solve problems such as aluminum complexes containing bridged β-diimine ligands that have not been seen

Inactive Publication Date: 2009-04-29
EAST CHINA UNIV OF SCI & TECH
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  • Summary
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  • Claims
  • Application Information

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Problems solved by technology

Although there are some reports (DaltonTrans., 2005, 1565-1566; DaltonTrans., 2006, 3855-3857; Organometallics, 2007, 26, 3416-3423) about bridged β-diimine organic compounds, but no A report on aluminum complexes containing bridged β-diimine [NN∩NN] ligands

Method used

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  • Novel bridged beta-diimido binuclear aluminum compound and preparation method and use thereof
  • Novel bridged beta-diimido binuclear aluminum compound and preparation method and use thereof
  • Novel bridged beta-diimido binuclear aluminum compound and preparation method and use thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Under argon protection, add 17.16g (50mmol) 4-(2-trifluoromethylphenyl)amino-3-penten-2-one to a 150mL Schlenk bottle, 20mL CH 2 Cl 2 , 9.501g (50mmol) [Et 3 O]+[BF4 ] - 10mLCH 2 Cl 2 Solution, after the dropwise addition, return to room temperature and stir, then add dropwise 15.15g (150mmol) triethylamine and 1.851g (25mmol) 1,3-propanediamine mixed solution to the above reaction solution, and stir for 12 hours after the dropwise addition, then reduce Remove the solvent under pressure to obtain a yellow sticky solid, add 80mL of toluene, filter and drain the solvent to obtain a yellow solid, the initial product is recrystallized with toluene to obtain a light yellow bridged β-diimine ligand: 1,3- Bis(2-(2-trifluoromethylanilino)-pent-2-en-4-ketimino)propane (8.122 g, 62% yield). Its structure is as follows:

[0032]

Embodiment 2

[0034] Under argon protection, add the bridged β-diimine ligand 1,2-bis(2-(2,6-diisopropylanilino)-pent-2-ene-4- Ketoimino) ethane (0.457g, 4.000mmol), n-hexane 30mL, drop AlEt therein at 0°C 3 (0.457g, 4.000mmol), after the dropwise addition was completed, it was allowed to rise to room temperature and stirred, reacted for 12 hours, filtered, concentrated and placed at -20°C to obtain colorless crystals (0.898g, 75%). Code 1a. Its structure is as follows:

[0035]

[0036] 1 H NMR (500MHz, CDCl 3 , 25°C): δ-0.30(dq, 2 J=14.3Hz, 3 J=8.2Hz, 4H, AlCH 2 CH 3 ), -0.10(dq, 2 J=14.3Hz, 3 J=8.2Hz, 4H, AlCH 2 CH 3 ), 0.91(t, 3 J=8.2Hz, 12H, AlCH 2 CH 3 ), 1.22(d, 3 J=6.8Hz, 12H, CH(CH 3 ) 2 ), 1.30(d, 3 J=6.8Hz, 12H, CH(CH 3 ) 2 ), 1.78 (s, 6H, CH 3 ), 2.28(s, 6H, CH 3 ), 3.09(q, 3 J=6.8Hz, 4H, CH(CH 3 ) 2 ), 3.52 (s, 4H, N-CH 2 ), 5.05(s, 2H, γ-CH), 7.24(t, 3 J=7.4Hz, 2H, p-Ar-H), 7.31(d, 3 J=7.4Hz, 4H, m-Ar-H). 13 C{ 1 H} NMR (100MHz, CDCl 3 , 25°C):...

Embodiment 3

[0038] Under argon protection, add ligand 1,2-bis(2-(2,6-dimethylanilino)-pent-2-en-4-ketimino)ethane ( 1.085g, 2.000mmol), n-hexane 30mL, drop AlEt therein at 0°C 3 (0.457g, 4.000mmol), after the dropwise addition, let it rise to room temperature and stir naturally, react for 12 hours, then filter, concentrate and put at -20°C to obtain colorless crystals (1.023g, 72%). Code 1b. Its structure is as follows:

[0039]

[0040] 1 H NMR (500MHz, CDCl 3 , 25°C): δ-0.27(dq, 2 J=14.3Hz, 3 J=8.1Hz, 4H, AlCH 2 CH 3 ), -0.16(dq, 2 J=14.3Hz, 3 J=8.1Hz, 4H, AlCH 2 CH 3 ), 0.75(t, 3 J=8.1Hz, 12H, AlCH 2 CH 3 ), 1.59 (s, 6H, CH 3 ), 2.14(s, 12H, Ar-CH 3 ), 2.17(s, 6H, CH 3 ), 3.44(s, 4H, N-CH 2 ), 4.85(s, 2H, γ-H), 7.04(m, 6H, Ar-H). 13 C{ 1 H} NMR (100MHz, CDCl 3 , 25°C): δ0.9(AlCH 2 CH 3 ), 9.5 (AlCH 2 CH 3 ), 18.7 (Ar-Me), 22.1 (CMe), 22.7 (CMe), 48.6 (N-CH 2 ), 98.0(CH), 125.9(Ar-C), 128.7(Ar-C), 134.0(Ar-C), 144.1(Ar-C), 168.1(NCMe), 170.1(NCMe).Anal.Calcd....

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Abstract

The invention discloses a novel bridged beta-diketiminate homodinuclear aluminum compound, a preparation method thereof and application of the compound in polymerization of lactones. The preparation method is as follows: a bridged beta-diketiminate homodinuclear ligand compound and alkyl aluminum are reacted in an organic medium to give a homodinuclear aluminum complex for a bridged beta-diketminate ligand. The bridged beta-diketiminate homodinuclear aluminum compound is a high-efficiency catalyst which can be used for catalyzing the polymerization of lactones. The bridged beta-diketiminate homodinuclear aluminum compound has the advantages of producing polycaprolactone (Mw / Mn is between 1.4 and 2.3) with high and narrowly distributed molecular weight due to higher catalytic activities and meeting demands of industrial department, along with easily available raw materials, simple synthesis course, high product yield and stable properties. The structural formula of the compounded is shown above.

Description

technical field [0001] The invention relates to a novel bridging β-diimine dinuclear aluminum compound and the application of this compound in lactone polymerization. Background technique [0002] Polylactones such as polycaprolactone and polylactide are completely biodegradable under natural environmental conditions and do not cause any pollution to the environment. Its excellent biocompatibility, permeability, low toxicity and its hydrolytic instability make polylactone materials a substitute for non-degradable polymer products, and can be used to make garbage bags, food containers and agricultural mulch films and other uses, and has high application value in biomedicine, and the mechanical processing properties of some chiral polylactones are even comparable to polypropylene products. [0003] The catalyst systems currently used in the coordination ring-opening polymerization of lactones mainly include stannous octoate, metal aluminum, calcium, magnesium, zinc, titanium ...

Claims

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Application Information

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IPC IPC(8): C07F5/06C08G63/84C08G63/08
Inventor 马海燕杜鹏龚劭刚
Owner EAST CHINA UNIV OF SCI & TECH
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