Tri-(beta-diketone imidogen) rare earth metal complex and uses thereof

A technology based on diketimine and rare earth metals, which is applied in the field of rare earth metal complexes, can solve the problems of no ring-opening polymerization, etc., and achieve the effects of long active life, high molecular weight and moderate molecular weight distribution

Inactive Publication Date: 2009-01-14
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, so far, in the application of β-diketoimine rare earth complexes in catalyzing the ring-opening polymerization of cyclic esters reported in the literature, β-diketoimine is only used as an auxiliary ligand to stabilize the activity of rare earth metals. center, that is, when the ring-opening polymerization of cyclic esters is catalyzed by β-diketoimine rare earth complexes, the active center structure is still rare earth-alkoxy, rare earth-amine, rare earth-hydroboration bonds, etc., and no relevant three (β-diketoimino)rare earth complexes as one-component catalysts for ring-opening polymerization of ε-caprolactone and L-lactide

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1: Ln[p-Me-C 6 h 4 NC(Me)CHC(Me)NC 6 h 4 -p-Me] 3 Synthesis of Complex Ln=Nd

[0021] The in situ generated Li[p-Me-C 6 h 4 NC(Me)CHC(Me)NC 6 h 4 -p-Me] (6.00 mmol) in toluene-hexane (15 mL) was added to NdCl in 15 mL THF 3 (0.50 g, 2.00 mmol) in the turbid liquid, reacted at room temperature for 24 hours, heated to 50°C for 48 hours, centrifuged, and discarded very little precipitate. The mother liquor was drained, added toluene for extraction, and centrifuged. The resulting clear liquid was concentrated and frozen overnight at 0° C. to obtain 1.27 g (1.30 mmol) of yellow-green crystals, with a yield of 65%.

[0022] Example 2: Ln[p-Cl-C 6 h 4 NC(Me)CHC(Me)NC 6 h 4 -p-Cl] 3 Synthesis of Complex Ln=Pr, La, Ce, Gd, Sm, Eu, Y

[0023] The in situ generated Li[p-Cl-C 6 h 4 NC(Me)CHC(Me)NC 6 h 4 -p-Cl] (9.00 mmol) in toluene-hexane (30 mL) was added to 25 mL of THF in LnCl 3 (0.74 g, 3.00 mmol) in the turbid solution, reacted at room temperatu...

Embodiment 3

[0024] Embodiment three: Ln[p-F-C 6 h 4 NC(Me)CHC(Me)NC 6 h 4 -p-F] 3 Synthesis of Complex Ln=Nd

[0025] The in situ generated Li[p-F-C 6 h 4 NC(Me)CHC(Me)NC 6 h 4 -p-F] (7.17 mmol) in toluene-hexane (20 mL) was added to NdCl in 15 mL THF 3 (0.60 g, 2.39 mmol) in the turbid solution, reacted at room temperature for 24 hours, heated to 50°C for 48 hours, centrifuged, and discarded very little precipitate. The mother liquor was frozen overnight at 0°C to obtain 1.82 g (1.67 mmol) of yellow-green crystals, with a yield of 70%.

Embodiment 4

[0026] Embodiment four: Ln[o-Me-C 6 h 4 NC(Me)CHC(Me)NC 6 h 4 -o-Me] 3 Synthesis of Complex Ln=Nd

[0027] The in situ generated Li[o-Me-C 6 h 4 NC(Me)CHC(Me)NC 6 h 4 -o-Me] (4.80 mmol) in toluene-hexane (15 mL) was added to 15 mL of THF in NdCl 3 (0.40 g, 1.60 mmol) in the turbid liquid, reacted at room temperature for 24 hours, heated to 50 ° C for 48 hours, centrifuged, and discarded very little precipitate. The mother liquor was drained, added toluene for extraction, and centrifuged. The resulting clear liquid was concentrated and frozen overnight at 0° C. to obtain 1.09 g (1.12 mmol) of yellow-green crystals, with a yield of 70%.

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PUM

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Abstract

The invention discloses a tri-(Beta-Diketiminato) rare-earth metal complex, having the following chemical formula: Ln[(C6H4X)NC(Me)CHC(Me)N(C6H4X)]3, wherein, Ln represents rare earth metal; and X is a substituent selected from Cl, F, H, p-CH3 or o-CH3. Meanwhile, the invention discloses an application of the complex in the ring-opening polymerization reaction of Epsilon-caprolactone and L-lactide as a catalyst. The tri-(Beta-Diketiminato) rare-earth metal complex can take Beta-Diketiminato as an active group to initiate the ring-opening polymerization reaction of Epsilon-caprolactone and L-lactide, and can catalyze the ring-opening polymerization by extreme high activity under mild conditions, the obtained polycaprolactone and polylactic acid have rather high molecular weight, and the molecular weight distribution is moderate.

Description

technical field [0001] The present invention relates to a rare earth metal complex, in particular to a tris(β-diketoimine) rare earth metal complex and its application in the ring-opening polymerization of ε-caprolactone and L-lactide . Background technique [0002] Polycaprolactone and polylactic acid (also known as polylactide) are two types of degradable synthetic polyalkyl esters with excellent biocompatibility, which have been widely used as biomedical polymer materials. In addition, as green polymer materials It also has great application prospects in eliminating white pollution caused by traditional plastics. These two types of polyalkyl esters are mainly synthesized by ring-opening polymerization of epsilon-caprolactone and L-lactide. [0003] At present, people have developed many catalytic systems for the ring-opening polymerization of the above-mentioned cyclic esters. The catalysts used can be main group metals, transition metals, and rare earth metal alkoxides...

Claims

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Application Information

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IPC IPC(8): C07C211/65C07F5/00C08G63/84C08G63/08
Inventor 薛明强沈琪焦锐
Owner SUZHOU UNIV
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