Asymmetric aluminum complex containing o-phenylenediamine group and its preparation method and application

An o-phenylenediamine-based, aluminum complex technology is applied in the field of asymmetric aluminum complexes, which can solve the problems of non-renewability and non-degradability, and achieve good molecular weight controllability, high stereoselectivity, and fast reaction rate. Effect

Active Publication Date: 2020-09-08
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] While traditional polymer plastics that use petroleum as raw materials bring convenience to people's production and life, they also have two fatal shortcomings: non-renewability and non-degradability

Method used

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  • Asymmetric aluminum complex containing o-phenylenediamine group and its preparation method and application
  • Asymmetric aluminum complex containing o-phenylenediamine group and its preparation method and application
  • Asymmetric aluminum complex containing o-phenylenediamine group and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] The structural formula of the synthesized ligand is the above formula (A), where R is hydrogen, and the reaction process is as follows: add 0.40 g of unilaterally protected o-phenylenediamine (a) and an equimolar amount of salicylaldehyde into 20 mL of methanol, and heat to reflux After 12 hours of reaction, after the reaction was completed, it was cooled and filtered, washed with cold methanol, filtered, collected, dried and weighed to obtain 0.50 g of solid, with a yield of 87.7%.

[0047] The product obtained is characterized, and the results are as follows:

[0048] 1 H NMR (400 MHz, CDCl 3 ) δ 12.86 (s, 1H, O H ), 8.42 (s, 1H, Ar H C=N), 7.85(m, 2H, Ar– H ), 7.64 (d, J = 7.0 Hz, 1H, Ar– H ), 7.56 (m, 1H, Ar– H ), 7.44 (m,3H, Ar– H ), 7.32 (m, 2H, Ar– H ), 6.96 (m, 4H, Ar– H ).

[0049] HRESI-MS: m / z cacld.C 21 h 14 N 2 o 3 [M-H] - ; 341.0926, found: 341.0924.

[0050] It can be seen from the above characterization results that the obtained produ...

Embodiment 2

[0052] The structural formula of the synthesized ligand is the above formula (A), where R is a methyl group, and the reaction process is as follows: 0.30 g of unilaterally protected o-phenylenediamine (a) and an equimolar amount of 3,5-dimethyl salicylaldehyde Add 20 mL of methanol, heat to reflux for 12 hours, cool and filter after the reaction, wash with cold methanol, filter, collect, dry and weigh to obtain 0.40 g of solid, with a yield of 85.1%.

[0053] The product obtained is characterized, and the results are as follows:

[0054] 1 H NMR (400 MHz, CDCl 3 ) δ 12.72 (s, 1H, O H ), 8.40 (s, 1H, Ar H C=N), 7.80(m, 2H, Ar– H ), 7.66 (m, 2H, Ar– H ), 7.15 (m, 3H, Ar– H ), 6.92 (s, 1H, Ar– H ),2.15 (s, 3H, ArC H 3 ), 2.04 (s, 3H, ArC H 3 ). HRESI-MS: m / z ccld. C 23 h 18 N 2 o 3 [M-H] - ; 369.1238, found: 369.1238.

[0055] It can be seen from the above characterization results that the obtained product is the ligand in which R is a methyl group in the above...

Embodiment 3

[0057] The structural formula of the synthesized ligand is the above formula (A), where R is bromine, and the reaction process is as follows: add 0.35 g of unilaterally protected o-phenylenediamine (a) and 3,5-dibromosalicylaldehyde in 20 In mL methanol, heated to reflux for 12 hours, after the reaction was completed, cooled and filtered and washed with cold methanol, filtered, collected, dried and weighed to obtain 0.66 g of solid, with a yield of 90.4%.

[0058] The product obtained is characterized, and the results are as follows:

[0059] 1 H NMR (400 MHz, CDCl 3 ) δ 12.64 (s, 1H, O H ), 8.344 (s, 1H, Ar H C=N),7.86 (d, J = 7.2 Hz, 1H, Ar– H ), 7.68 (m, 3H, Ar– H ), 7.42 (m, 2H, Ar– H ), 7.36(m, 1H, Ar– H ), 7.10 (m, 3H, Ar– H ).

[0060] HRESI-MS: m / z cacld.C 21 h 12 Br 2 N 2 o 3 [M-H] - ; 496.9134, found: 496.9136.

[0061] It can be seen from the above characterization results that the obtained product is the ligand in which R is bromine in the above f...

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Abstract

The invention discloses an asymmetric aluminum complex containing o-phenylenediamine group and a preparation method and application thereof, the asymmetric aluminum complex has the structural formulaof formula I, wherein R is hydrogen, C1-C4 alkane or halogen. An asymmetric aluminum complex catalyst containing the o-phenylenediamine group is obtained by reacting a ligand with trimethylaluminum, apreparation method is simple, low in cost and high in product yield, the asymmetric aluminum complex has a special structure, and various structural changes, metal center aluminum can be coordinatedwith divalent N, N, O and O of the ligand, the asymmetric aluminum complex catalyst can be used as a catalyst for ring-opening polymerization of cyclic lactones, has high catalytic activity, good stereoselectivity and fast reaction rate, polymerization operation is simple, the obtained polymerization product has a narrow molecular weight distribution, a controllable molecular weight and a high yield, and the asymmetric aluminum complex catalyst can be widely used for ring-opening polymerization of the cyclic lactones, and is an ideal catalyst.

Description

technical field [0001] The present invention relates to an asymmetric aluminum complex containing an o-phenylenediamine group, and also relates to the asymmetric aluminum complex containing an o-phenylenediamine group, its preparation method and its application as a catalyst for the ring-opening polymerization reaction of a cyclic lactone . Background technique [0002] While traditional polymer plastics that use petroleum as raw materials bring convenience to people's production and life, they also have two fatal shortcomings: non-renewability and non-degradability. Because petroleum is a non-renewable resource, the rapid development of polymer plastic materials that rely on petroleum raw materials is greatly restricted, and polymer plastic materials are difficult to degrade, and a large amount of polymer plastic material waste has accumulated in real life for a long time. Pollution has also gradually increased. Finding renewable resources to replace petroleum and develop...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/06C08G63/08C08G63/84
CPCC07B2200/07C07F5/066C08G63/08C08G63/823
Inventor 姚伟高爱红张永芳王洪宾
Owner UNIV OF JINAN
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