Imine phenol oxymagnesium compound, and preparation method and application thereof

A technology of iminophenoxymagnesium and compounds, which is applied in the field of iminophenoxymagnesium compounds, can solve the problem of rac-lactide inactivity, etc., and achieve the effects of convenient preparation, high catalytic activity and stable properties

Inactive Publication Date: 2012-12-26
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 2010, Otero reported a magnesium complex containing cyclopentadienylpyrazolyl, which showed high activity on L-lactide, but no activity on rac-lactide (Inorg.Chem.2010, 49, 2859-2871)
In terms of catalyzing the selective polymerization of racemic lactide, previous reports usually obtain atactic polylactide or polylactide with heterotactic tendency, and there are few reports on magnesium catalysts with high selectivity. Therefore, A lot of research work needs to be further carried out to synthesize catalysts with high activity and high stereoselectivity

Method used

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  • Imine phenol oxymagnesium compound, and preparation method and application thereof
  • Imine phenol oxymagnesium compound, and preparation method and application thereof
  • Imine phenol oxymagnesium compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Synthesis of Ligand L1

[0037] Add 0.961g (5mmol) of 3-tert-butyl-5-methylsalicylaldehyde, 0.996g (5mmol) of 2-methoxy-2'-aminobiphenyl, 50mL of ethanol into a 100mL single-necked flask, at 80°C Heated to reflux for 3 h, concentrated to 20 mL, and recrystallized to obtain 1.494 g of orange-red crystals, with a yield of 80%.

[0038]

[0039] 1 H NMR (CDCl 3 , 400MHz): δ13.35(s, 1H, OH), 8.47(s, 1H, N-CH-Ar), 7.41(m, 2H, ArH), 7.34(t, 2H, 3 J=7.5Hz ArH), 7.22(m, 2H, ArH), 7.12(s, 1H, ArH), 7.00(t, 1H, 3 J=7.4Hz ArH), 6.96(m, 2H, ArH), 3.73(s, 3H, CH 3 O-Ar), 2.28(s, 3H, CH3-Ar), 1.37(s, 9H, C(CH 3 ) 3 ). 13 C NMR (CDCl 3 , 100MHz): δ162.77, 158.32, 156.46, 147.34, 137.19, 133.95, 131.29, 131.09, 130.98, 130.06, 128.97, 128.49, 128.41, 126.50, 126.42, 120.35, 118.7 (N-CH-Ar), 55.19 (CH 3 O-Ar), 34.70 (C (CH 3 ) 3 ), 29.23 (C (CH 3 ) 3 ), 20.62 (CH 3 -Ar).HRMS calcd.for C 25 h 27 NO 2 : 373.2042; found: 373.2041.

Embodiment 2

[0041] Synthesis of Ligand L2

[0042] Add 1.172g (5mmol) of 3,5-di-tert-butyl salicylaldehyde, 0.996g (5mmol) of 2-methoxy-2'-aminobiphenyl, and 50mL of ethanol into a 100mL single-necked flask, and heat to reflux at 80°C After 3 hours, it was concentrated to 20 mL and then recrystallized to obtain 1.704 g of orange-red crystals, with a yield of 82%.

[0043]

[0044] 1 H NMR (CDCl 3 , 400MHz): δ13.40(s, 1H, OH), 8.53(s, 1H, N-CH-Ar), 7.43-7.38(m, 3H, ArH), 7.34(m, 2H, ArH), 7.21( t, 2H, 3 J=6.7Hz ArH), 7.15(d, 1H, 4 J=2.3Hz ArH), 6.99(t, 1H, 3 J=7.4Hz ArH), 6.95(d, 1H, 3 J=8.3Hz ArH), 3.77(s, 3H, CH 3 O-Ar), 1.39(s, 9H, C(CH 3 ) 3 ), 1.31(s, 9H, C(CH 3 ) 3 ). 13 C NMR (CDCl 3 , 100MHz): δ163.06, 158.23, 156.47, 147.41, 140.00, 136.75, 134.05, 131.34, 130.96, 128.91, 128.50, 128.46, 127.57, 126.42, 126.37, 120.31, 118.3 (N-CH-Ar), 55.22 (CH 3 O-Ar), 35.01 (C (CH 3 ) 3 ), 34.10 (C (CH 3 ) 3 ), 31.45 (C (CH 3 ) 3 ), 29.27 (C (CH 3 ) 3 ).HRMS calcd.for ...

Embodiment 3

[0046] Synthesis of Ligand L3

[0047] Add 0.751g (5mmol) of 3,5-dimethyl salicylaldehyde, 0.996g (5mmol) of 2-methoxy-2'-aminobiphenyl, and 50mL of ethanol into a 100mL single-necked flask, and heat to reflux at 80°C for 3h , concentrated to 20 mL and then recrystallized to obtain 1.408 g of yellow crystals, with a yield of 85%.

[0048]

[0049] 1 H NMR (CDCl 3 , 400MHz): δ12.63(s, 1H, OH), 8.46(s, 1H, N-CH-Ar), 7.42-7.35(m, 4H, ArH), 7.24(dd, 1H, 3 J=7.4Hz, 4 J=1.7Hz ArH), 7.18(dd, 1H, 3 J=7.8Hz, 4 J=1Hz ArH), 7.01(m, 2H, ArH), 6.94(m, 2H, ArH), 3.71(s, 3H, CH 3 O-Ar), 2.26(s, 3H, CH 3 -Ar), 2.18(s, 3H, CH 3 -Ar). 13 C NMR (CDCl 3 , 100MHz): δ162.73, 157.14, 156.51, 147.78, 134.96, 133.74, 131.27, 131.15, 129.64, 129.09, 128.56, 128.49, 127.12, 126.39, 125.85, 120.50, 118.4 (N-CH-Ar), 55.35 (CH 3 O-Ar), 20.33 (CH 3 -Ar), 15.50 (CH 3 -Ar).HRMS calcd.for C 22 h 21 NO 2 : 331.1572; found: 331.1570.

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Abstract

The invention discloses an imine phenol oxymagnesium compound, a preparation method and application thereof in catalyzing lactone ring opening polymerization. The preparation method comprises the following steps of: enabling neutral ligands to directly react with magnesium amide in methylbenzene, and then conducting filtration, concentration and recrystallization to obtain target compounds from reaction products. The imine phenol oxymagnesium compound provided by the invention is a high-efficiency catalyst for lactone ring opening polymerization, and can be used for polymerization of lactide, epsilon-caprolactone and the like. The imine phenol oxymagnesium compound provided by the invention has very remarkable advantages that the raw materials are easy to obtain, the synthesis line is simple, the product yield is high, the property is comparatively stable, the catalytic activity is higher, high-molecular-weight polylactide and polycaprolactone can be obtained, and the needs of industrial departments can be met. The structural formula of the imine phenol oxymagnesium compounds is shown as the accompanying drawing.

Description

technical field [0001] The present invention relates to a class of imine phenoxymagnesium compounds and the application of such compounds in lactone polymerization. Background technique [0002] Aliphatic polyester materials are widely used in the field of biomedicine due to their good biocompatibility and degradability, such as slow-release materials for drugs and medical suture materials. At the same time, its good mechanical processing performance and easy degradation determine that it will become an important substitute for polyolefin materials in the future when oil resources are increasingly tight, and it can well solve the current "white pollution" problem. The monomers currently used in the research of lactone polymerization include lactide, caprolactone, glycolate and butyrolactone; among the above-mentioned monomers, lactide can be obtained by lactic acid dimerization, and the source of raw materials is wide and the price is low. low. Lactide has three isomers, L...

Claims

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Application Information

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IPC IPC(8): C07F19/00C08G63/83C08G63/08
Inventor 马海燕易炜
Owner EAST CHINA UNIV OF SCI & TECH
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