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A kind of aminophenoxy potassium complex and its preparation method and application

A technology of potassium aminophenoxy complexes, which is applied in the field of potassium aminophenoxy complexes, can solve the problems of low molecular weight of polymers, and achieve the effects of convenient preparation, stable properties and wide application prospects

Active Publication Date: 2020-08-11
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 2015, the Cano group designed and synthesized a series of potassium iminophenolate complexes, which catalyzed the polymerization of 100 equivalents of rac-LA, and the monomer conversion rate could reach 99% in 0.5 minutes, but this series of complexes catalyzed rac-LA The polymer obtained by polymerization has a lower molecular weight (Organometallics, 2015, 34, 477)
[0005] So far, potassium complexes have been used as lactone ring-opening polymerization catalysts, and racemic lactide has shown high catalytic activity, but due to the high sensitivity of the complex to water, oxygen, and impurities, it is difficult to catalyze A large proportion of monomers are polymerized to obtain very high molecular weight polylactide

Method used

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  • A kind of aminophenoxy potassium complex and its preparation method and application
  • A kind of aminophenoxy potassium complex and its preparation method and application
  • A kind of aminophenoxy potassium complex and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Synthesis of Potassium Complex K1

[0047] Add Ligand L to a 50 mL Schlenk bottle 1 H (633mg, 1.00mmol), add 2mL of toluene to dissolve it, slowly drop KN(SiMe 3 ) 2 (200mg, 1.00mmol) in toluene (2mL), stirred overnight at room temperature. After filtration, the filtrate was drained to obtain a pale yellow foamy solid, which was recrystallized with a mixed solvent of toluene and n-hexane, and a pale yellow solid was precipitated, which was drained to obtain a pale yellow solid K1 (421 mg, 51%).

[0048]

[0049] 1 H NMR (C 6 D. 6 ,400MHz,298K):δ7.88–7.47(m,6H,ArH),7.27–7.20(m,2H,ArH),7.14–7.08(m,6H,ArH),7.07–7.03(m,2H,ArH ),7.03–6.94(m,5H,ArH),4.82(d,1H, 2 J=7.8Hz,CHN),4.59(pseudo-t,1H, 2 J≈ 3 J=7.0Hz,CH 2 O),4.29(d,1H, 2 J=10.0Hz, ArCH 2 ),3.26(d,1H, 2 J=10.0Hz, ArCH 2 ),3.04–2.84(m,3H,2H of NCH 2 C=N,1H of CHCH 2 ),2.83–2.73(m,2H,1Hof CHCH 2 ,1H of CH 2 CHCH 2 ),2.31(s,3H,ArCH 3 ),1.98–1.88(m,1H,CH 2 ofcyclohexyl), 1.74–1.64 (m, 1H, CH 2 of cy...

Embodiment 2

[0051] Synthesis of Potassium Complex K2

[0052] Ligand L 2 H (607mg, 1.00mmol), KN (SiMe 3 ) 2 (200mg, 1.00mmol), the rest of the steps are the same as in Example 1. K2 was obtained as a pale yellow solid (381 mg, 59%).

[0053]

[0054] 1 H NMR (C 6 D. 6 ,400MHz,298K):δ7.70–7.34(m,6H,ArH),7.27–7.17(m,2H,ArH),7.13–6.94(m,12H,ArH),6.92(m,1H, 3 J=8.0Hz, ArH), 5.20–4.86 (br, 1H, CHN), 4.64–4.56 (m, 1H, CHN) 2 O), 4.48–4.20 (br, 1H, ArCH 2 ),3.50–3.04(br,1H,ArCH 2 ),3.04–2.63(m,4H,2HofNCH 2 C=N,2H of CHCH 2 ), 2.62–2.42 (br, 1H, NCH 2),2.41–2.30(m,1H,NCH 2 ),2.23(s,3H,ArCH 3 ),1.36–1.15(m,2H,NCH 2 CH 2 ), 1.13–0.96 (m,2H,CH 2 CH 3 ),0.76(t,3H, 3 J=7.2Hz,CH 2 CH 3 ). 13 C{ 1 H}NMR (C 6 D. 6 ,100MHz,298K):δ167.8(OC=N),166.7,142.3,140.2,137.9,133.3,132.3,131.9,129.3,128.8,128.6,127.5,127.0,125.70,125.66,125.4,125.2,114 Ar-C), 82.7(CHN), 76.6(CHO), 64.3(Ph 3 C), 50.4 (ArCH 2 ), 39.6 (NCH 2 C=N),28.4(NCH 2 CH 2 ), 27.6 (PhCH 2 CH),21.46(NCH 2 CH 2 ...

Embodiment 3

[0056] Synthesis of Potassium Complex K3

[0057] Ligand L 3 H (607mg, 1.00mmol), KN (SiMe 3 ) 2 (200mg, 1.00mmol), the rest of the steps are the same as in Example 1. K3 was obtained as pale yellow solid (381 mg, 59%).

[0058]

[0059] 1 H NMR (C 6 D. 6 ,400MHz,298K):δ7.64–7.32(m,5H,ArH),7.20–7.16(m,3H,ArH),7.13–6.99(m,10H,ArH),6.98–6.90(m,4H,ArH ), 6.60 (s, 1H, ArH), 4.50–4.24 (br, 1H, CHN), 4.14–3.94 (br, 1H, CHN 2 O),3.68–3.20(br,3H,1H of CH 2 O,2H of ArCH 2 ), 3.06–2.74 (br, 3H, 2Hof NCH 2 C=N,1H of NCH 2 CH 2 ),2.68–2.43(br,2H,1H of NCH 2 CH 2 ,1H of PhCH 2 CH),2.39–2.29(m,1H,PhCH 2 CH),2.25(s,3H,ArCH 3 ), 1.45–1.30 (br, 2H, NCH 2 CH 2 ), 1.24–1.09 (m,2H,CH 2 CH 3 ),0.86(t,3H, 3 J=7.2Hz,CH 2 CH 3 ). 13 C NMR (C 6 D. 6 ,100MHz,298K):δ168.0(NCH 2 C=N), 166.7, 138.0, 137.9, 135.6, 133.4, 132.3, 129.5, 129.3, 129.0, 128.6, 127.0, 125.7, 125.0, 114.8 (All ArC), 71.1 (CHN), 67.4 (CH 2 O), 64.4 (Ph 3 C), 49.7 (ArCH 2 ), 41.9 (NCH 2 C=N),32.0(...

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Abstract

The invention discloses an amido phenoxy potassium complex containing oxazoline rings or benzoxazole rings, a preparation method of the complex and an application of the complex to high-activity catalysis lactone ring opening polymerization. The preparation method of the amido phenoxy potassium complex containing the oxazoline rings or the benzoxazole rings includes the steps: directly reacting neutral ligands with metal raw material compounds in organic media; performing filtration, concentration and recrystallization to obtain target compounds. The amido phenoxy potassium complex is providedwith an efficient lactone ring opening polymerization catalyst, can be used for catalyzing polymerization reaction of lactones such as lactide and is particularly used for catalyzing racemic lactonesto obtain a polymer with high-molecular weight. The amido phenoxy potassium complex has obvious advantages that raw materials are easily acquired, a synthetic route is simple, product yield is high,the complex has high catalytic activity, polyester materials with high-molecular weight can be acquired, and the requirements of industrial departments can be met. The structural formula of the amidophenoxy potassium complex is as shown in the specification.

Description

technical field [0001] The invention relates to a class of potassium aminophenolate complexes containing oxazoline rings or benzoxazole rings and the application of such complexes in lactone polymerization. Background technique [0002] As a class of polymers that can replace traditional petroleum-based polyolefin materials, aliphatic polyesters have attracted extensive attention due to their good biocompatibility and degradability. Among many degradable polymers, polylactic acid not only has good biocompatibility, degradability and excellent processability, but also has renewable raw materials. It is an environmentally friendly polymer and is a promising aliphatic polymer. Esters have been widely used in medical devices, drug-carrying and tissue engineering materials, and food packaging materials. In recent years, the ring-opening polymerization of lactic acid cyclic dimer lactide as raw material under the catalysis of nucleophilic small organic molecules or metal complexe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/06C08G63/08C08G63/83
CPCC07F1/005C08G63/823
Inventor 马海燕胡建文黄洋
Owner EAST CHINA UNIV OF SCI & TECH