Nitrogen-containing ligand rare earth catalyst and application thereof in polyester synthesis

A technology of rare earth complexes and ligands, applied in the field of novel tridentate nitrogen ligands and rare earth complexes thereof, can solve the problems of materials not having biodegradation characteristics and environmental pollution, etc.

Inactive Publication Date: 2008-05-28
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] 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 pol

Method used

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  • Nitrogen-containing ligand rare earth catalyst and application thereof in polyester synthesis
  • Nitrogen-containing ligand rare earth catalyst and application thereof in polyester synthesis
  • Nitrogen-containing ligand rare earth catalyst and application thereof in polyester synthesis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037]Dissolve 8.20 g of 2-(2,6-diisopropylanilino)-2-penten-4-one, 2.79 g of N,N-dimethylethylenediamine and 50 mg of p-toluenesulfonic acid in 30 mL of benzene , heated to reflux for water separation for 24 hours, removed the solvent in vacuo, and distilled under reduced pressure to obtain 7.02 g of yellow oily tridentate nitrogen ligand L1 with a yield of 67%. by 1 HNMR, 13 CNMR, mass spectrometry and elemental analysis characterized the structure of the ligands. Anal.Calcd.for C 21 h 35 N 3 : C, 76.54; H, 10.71; N, 12.75. Found: C, 76.65; H, 10.86; N, 12.76. 1 H NMR (300MHz, C 6 D. 6 , 25°C): δ (ppm) 11.04 (br s, 1H, NH), 7.24-7.14 (m, 3H, Ar-H), 4.71 (s, 1H, MeC (N) CH), 3.20 (sp, 3 J HH = 6.9Hz, 2H, ArCHMe 2 ), 2.97(t, 3 J HH = 6.3Hz, 2H, NCH 2 ), 2.18(t, 3 J HH = 6.3Hz, 2H, NCH 2 ), 1.95 (s, 6H, NMe 2 ), 1.69(s, 3H, MeC(NHAr)), 1.66(s, 3H, MeC(NCH 2 CH 2 NMe 2 )), 1.27(t, 3 J HH = 7.8Hz, 12H, ArCHMe 2 ). 1 H NMR (300MHz, CDCl 3 , 25°C): δ(ppm) 1...

Embodiment 2

[0039] Dissolve 5.79 g of 2-(2,6-diisopropylanilino)-2-penten-4-one, 2.59 g of N,N-diethylethylenediamine and 50 mg of p-toluenesulfonic acid in 30 mL of toluene , heated to reflux for water separation for 24 hours, removed the solvent in vacuo, and distilled under reduced pressure to obtain 4.51 g of yellow oily tridentate nitrogen ligand L2 with a yield of 56%. by 1 HNMR, 13 CNMR, mass spectrometry and elemental analysis characterized the structure of the ligands. C 23 h 39 N 3 Elemental analysis data: Calculated value C, 77.26; H, 10.99; N, 11.75. Measured value: C, 77.45; H, 10.95; N, 11.64. 1 H NMR (300MHz, C 6 D. 6 , 25°C): δ (ppm) 10.95 (br s, 1H, NH), 7.23-7.13 (m, 3H, Ar-H), 4.72 (s, 1H, MeC (N) CH), 3.21 (sp, 3 J HH = 6.9Hz, 2H, ArCHMe 2 ), 2.99 (q, 2H, NCH 2 ), 2.38(t, 3 J HH = 6.9Hz, 2H, NCH 2 ), 2.30(q, 4H, N(CH 2 CH 3 ) 2 ), 1.70(s, 6H, MeC(NHAr) and MeC(NCH 2 CH 2 NET 2 )), 1.28(d, 3 J HH = 6.9Hz, 6H, ArCHMe 2 ), 1.24(d, 3 J HH = 6.2Hz, ...

Embodiment 3

[0041] Dissolve 5.01 g of 2-(2,6-diisopropylanilino)-2-penten-4-one, 2.47 g of N-(2-aminoethyl)piperidine and 50 mg of p-toluenesulfonic acid in 25 mL of toluene , heated to reflux for water separation for 24 hours, removed the solvent in vacuo, and distilled under reduced pressure to obtain 4.19 g of yellow oily tridentate nitrogen ligand L3 with a yield of 59%. by 1 HNMR, 13 CNMR, mass spectrometry and elemental analysis characterized the structure of the ligands. C 24 h 39 N 3 Elemental analysis data: Calculated: C, 77.99; H, 10.64; N, 11.37. Found: C, 78.01; H, 10.46; N, 10.93. 1 H NMR (300MHz, C 6 D. 6, 25°C): δ (ppm) 11.01 (br s, 1H, NH), 7.24-7.16 (m, 3H, Ar-H), 4.71 (s, 1H, MeC (N) CH), 3.20 (sp, 3 J HH = 6.9Hz, 2H, ArCHMe 2 ), 3.03(t, 3 J HH = 6.9Hz, 2H, NCH 2 ), 2.27(t, 3 J HH =6.6Hz, 2H, NCH 2 ), 2.19(m, 4H, N(CH 2 CH 2 ) 2 CH 2 ), 1.69(s, 3H, MeC(NHAr)), 1.67(s, 3H, MeC(NCH 2 CH 2 NC 5 h 10 )), 1.39(m, 4H, N(CH 2 CH 2 ) 2 CH 2 ), 1.29(d,...

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Abstract

The invention relates to a new N-N-N tridentate ligand, relative rare-earth complex and relative application in the synthesis as poly-lactide acid or poly-caprolactone. The inventive ligand can be prepared from relative beta-diketone and amine via two-step condensation, the rare-earth complex can be prepared from the ligand with rare-earth alkyl compound or aamino-compound. The complex can catalyze lactide to open ring and polymerize to obtain polymer polyester, and catalyze caprolactone to polymerize. The formula of the complex is represented as above, wherein Ln is rare-earth metal ion as Y, Nd, Sm, Sc or the like, R1 is alkane of C1-10, R2 is alkane of C1-6, R2 is chain or cyclic alkane of C1-10, and X is alkyl, amido or alkoxy bonded with rare-earth ion.

Description

Technical field: [0001] The invention relates to a novel tridentate nitrogen ligand and its rare earth complex and its application in the synthesis of polylactide and polycaprolactone. technical background: [0002] In recent years, rare earth metal complexes have shown good catalytic activity in many organic reactions and polymer synthesis. The most researched category is rare earth metal compounds, but due to the relatively high cost of synthesizing such compounds, people gradually turn their attention to the rare earth metal complexes of nitrogen-containing ligands with lower synthesis costs, and rare earth metal complexes - Nitrogen bond formation helps to stabilize highly electrophilic, unstable rare earth metal compounds. Among a series of nitrogen-containing ligands, the most potential for development is the β-diimine ligand, which can be prepared by condensation of the corresponding β-diketone and amine. The steric and electronic effects of such ligands can be easi...

Claims

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Application Information

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IPC IPC(8): C07F5/00C08F4/52C08G63/08
Inventor 陈耀峰徐信
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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