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Novel three-tooth nitrogen ligand and rare earth metal complex

A technology of rare earth complexes and rare earth metals, which can be used in the preparation of organic compound/hydride/coordination complex catalysts, organic silicon compounds, imino compounds, etc., which can solve problems such as environmental pollution and materials that do not have biodegradable properties.

Inactive Publication Date: 2009-07-29
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] In recent years, while polymer materials bring convenience to people's lives, most of them do not have the characteristics of biodegradation, causing serious environmental pollution problems after being discarded.
At present, the disposal methods of non-degradable products are often landfill and incineration, which can only alleviate environmental pollution

Method used

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  • Novel three-tooth nitrogen ligand and rare earth metal complex
  • Novel three-tooth nitrogen ligand and rare earth metal complex
  • Novel three-tooth nitrogen ligand and rare earth metal complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] In a 250mL three-necked flask, add 2-(2,6-diisopropylanilino)-2-penten-4-one (5.5g, 21.5mmol), N-tert-butyl-(1,2-ethanedi amine) (2.5 g, 21.5 mmol), a catalytic amount of p-toluenesulfonic acid, and 100 mL of toluene. Under the protection of nitrogen, the water was refluxed for 24 hours. Finally, 13.4 g (136° C. / 5 Pa) of the tridentate nitrogen ligand L was obtained as a light yellow oily product, with a yield of 45%. by 1 HNMR, 13 C NMR and mass spectrometry characterized the structure of the ligands. 1 H NMR (300MHz, C 6 D. 6 , 25°C): δ (ppm) 11.03 (br, 1H, MeC (NH) CH), 7.06-7.18 (m, 3H, ArH), 4.67 (s, 1H, MeC (N) CH), 3.14 (sp, 3 J HH = 6.6Hz, 2H, ArCHMe 2 ), 2.97 (q, 2H, NCH 2 ), 2.45(t, 3 J HH = 6.3Hz, 2H, NCH 2 ), 1.68(s, 3H, MeC), 1.64(s, 3H, MeC), 1.24(d, 3 J HH = 6.9Hz, 6H, ArCHMe 2 ), 1.20(d, 3 J HH = 6.9Hz, 6H, ArCHMe 2 ), 0.88(s, 9H, NCMe 3 ), 0.45 (br, 1H, t Bu-NH). 1 H NMR (300MHz, CDCl 3 , 25°C): δ (ppm) 10.83 (br, 1H, MeC (NH) CH),...

Embodiment 2

[0044] In a 250mL three-necked flask, add 2-(2,6-diisopropylanilino)-2-penten-4-one (14.6g, 56.3mmol), N-2,6-dimethylphenyl- (1,2-Ethylenediamine) (9.5 g, 57.8 mmol), catalytic amount of p-toluenesulfonic acid and 100 mL of toluene. Under the protection of nitrogen, the water was refluxed for 24 hours. After the reaction was complete, the solvent was removed in vacuo to obtain a brown viscous substance. The tridentate nitrogen ligand L212g was obtained as a white solid by recrystallization from methanol with a yield of 52%. by 1 H NMR, 13 C NMR and mass spectrometry characterized the structure of the ligands. 1 H NMR (300MHz, C 6 D. 6 , 25°C): δ (ppm) 11.18 (br, 1H, MeC (NN) CH), 7.13-7.22 (m, 3H, ArH), 6.87-6.96 (m, 3H, ArH), 4.71 (s, 1H, MeC(NH)CH), 3.17(sp, 3 J HH =7.2Hz, 2H, ArCHMe 2 ), 3.15 (br, 1H, NH), 2.92 (br, 2H, NCH 2 ), 2.86 (br, 2H, NCH 2 ), 2.14(s, 6H, ArMe), 1.67(s, 3H, MeC), 1.58(s, 3H, MeC), 1.22(d, 3 J HH = 6.9Hz, 6H, ArCHMe 2 ), 1.21(d, 3 J ...

Embodiment 3

[0046]In a 250mL three-necked flask, add 2-(2,6-diisopropylanilino)-2-penten-4-one (7.06g, 27.2mmol), N-2,6-diisopropylphenyl -(1,2-Ethylenediamine) (6 g, 27.2 mmol), catalytic amount of p-toluenesulfonic acid and 100 mL of toluene. Under the protection of nitrogen, the water was refluxed for 24 hours. After the reaction was complete, the solvent was removed in vacuo to obtain a brown viscous substance. Methanol recrystallization gave 35.5 g of tridentate nitrogen ligand L as a white solid, with a yield of 44%. by 1 HNMR, 13 CNMR and mass spectrometry characterized the structure of the ligand. 1 HNMR (300MHz, C 6 D. 6 , 25°C): δ (ppm) 11.29 (br, s, 1H, MeC(NH)CH), 7.24-7.25 (br, m, 6H, ArH), 4.80 (s, 1H, MeC(NH)CH), 3.36 (sp, 3 J HH =7.2Hz, 2H, ArCHMe 2 ), 3.23 (sp, 3 J HH = 6.9Hz, 2H, ArCHMe 2 ), 3.15 (br, 2H, NCH 2 ), 2.98 (br, 2H, NCH 2 ), 1.75(s, 3H, MeC), 1.74(s, 3H, MeC), 1.29(d, 3 J HH = 7.2Hz, 12H, ArCHMe 2 ), 1.25(d, 3 J HH = 6.9Hz, 12H, ArCHMe 2 ...

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Abstract

The invention relates to a novel tridentate nitrogen ligand, rare earth metal complexes thereof and the application of the rare earth metal complexes in the olefin hydroamination reaction and the polyester synthesis. The ligand of the kind can be obtained from corresponding beta diketone and amine by two-step condensation reaction; the rare earth complexes can be obtained by the reaction between the ligand and rare earth metal alkyl and amidine compounds. The rare earth complexes can effectively catalyze the olefin hydroamination reaction and the ring-opening polymerization of lactones. The structural general formulas of the tridentate nitrogen and the corresponding rare earth complexes are shown as above.

Description

Technical field: [0001] The invention relates to a novel tridentate nitrogen ligand and its rare earth metal complex and its application in olefin hydroamination and lactone ring-opening polymerization. technical background: [0002] In recent years, rare earth metal complexes have shown good catalytic activity in many organic reactions and polymer synthesis reactions. Among them, the most widely studied are rare earth metal complexes containing cyclopentadienyl ligands. However, the synthesis cost of such complexes is relatively high. Therefore, people have studied many non-cyclopentadienyl-type rare earth metal complexes. Nitrogen-containing ligands play an important role in non-cene-type rare earth metal complexes. Nitrogen-containing ligands are generally easy to synthesize and low in cost, and the formation of rare earth metal-nitrogen bonds helps to stabilize rare earth metal compounds with high electrophilicity and high reactivity. Among a series of nitrogen-conta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/12C07F5/00C07F7/08C07F7/10C07C249/02B01J31/22C07C209/60C08G63/84
Inventor 陈耀峰陆而立甘伟
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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