Chiral aluminum complex containing acetylacetone derivative and preparation method and application thereof

A technology of acetylacetone and aluminum complexes, which is applied in the field of chiral aluminum complexes and their preparation, can solve the problems of polluting the ecological environment, slow degradation, and restricting rapid development, and achieves high catalytic activity, diverse structural changes, and controllable molecular weight. good effect

Active Publication Date: 2018-04-24
新泰中学
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Traditional polymer materials using petroleum as raw materials have penetrated into all aspects of economy and life. Traditional polymer materials degrade very slowly under natural conditions. While they bring convenience to people's lives, their use waste constitutes a huge amount. "White garbage" has seriously polluted the ecological environment, and in the case of petroleum as a non-renewable resource facing depletion, the rapid development of polymer materials that rely on petroleum raw materials is greatly restricted

Method used

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  • Chiral aluminum complex containing acetylacetone derivative and preparation method and application thereof
  • Chiral aluminum complex containing acetylacetone derivative and preparation method and application thereof
  • Chiral aluminum complex containing acetylacetone derivative and preparation method and application thereof

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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 1 is methyl; R 2 is methyl, the reaction process is: add 0.25 g of unilaterally protected chiral cyclohexanediamine (a) and equimolar amount of acetylacetone into 20 mL of methanol, heat and reflux for 10 hours, cool and filter after the reaction, and use cold washed with methanol, filtered, collected, dried and weighed to obtain 0.29 g of solid, with a yield of 87.9%.

[0047] The NMR information of the obtained product is as follows, as can be seen from the NMR information, R 1 is methyl; R 2 The ligand for the methyl group was successfully synthesized.

[0048] 1 H NMR (400 MHz, CDCl 3 ) δ 11.10 (s, 1H, O H ), 8.13 (d, J = 7.0Hz, 2H,Ar– H ), 7.62 (d, J = 7.0 Hz, 2H, Ar– H ), 5.26 (s, 1H, C H ), 4.32 (m, 1H, NC H ),3.45 (m, 1H, =NC H ), 2.54 (m, 1H, C H 2 ), 2.10 (s, 6H, C H 3 ), 2.00 (m, 5H, C H 2 ),1.52 (m, 2H, C H 2 ). HRESI-MS: m / z ccld. C 19 h 22 N 2 o ...

Embodiment 2

[0050] The structural formula of the synthesized ligand is the above formula (A), where R 1 is methyl; R 2 is trifluoromethyl, the reaction process is: add 0.30 g of unilaterally protected chiral cyclohexanediamine (a) and an equimolar amount of trifluoroacetylacetone into 20 mL of methanol, heat and reflux for 12 hours, after the reaction Cool and filter and wash with cold methanol, filter, collect, dry and weigh to obtain 0.38 g of solid, with a yield of 80.9%.

[0051] The NMR information of the obtained product is as follows, as can be seen from the NMR information, R 1 is methyl; R 2 The ligand for trifluoromethyl was synthesized successfully.

[0052] 1 H NMR (400 MHz, CDCl 3 ) δ 11.03 (s, 1H, O H ), 8.17 (d, J = 7.2 Hz, 2H,Ar– H ), 7.52 (d, J = 7.2 Hz, 2H, Ar– H ), 5.70 (s, 1H, C H ), 4.33 (m, 1H, NC H ),3.45 (m, 1H, =NC H ), 2.58 (m, 1H, C H 2 ), 2.12 (s, 3H, C H 3 ), 2.04 (m, 5H, C H 2 ),1.61 (m, 2H, C H 2 ). HRESI-MS: m / z cacld.C 19 h 19 f...

Embodiment 3

[0054] The structural formula of the synthesized ligand is the above formula (A), where R 1 is trifluoromethyl; R 2 is a phenyl group, the reaction process is: add 0.20 g of unilaterally protected chiral cyclohexanediamine (a) and an equimolar amount of benzoyltrifluoroacetone to 10 mL of methanol, heat and reflux for 8 hours, and after the reaction Cool and filter and wash with cold methanol, filter, collect, dry and weigh to obtain 0.29 g of solid, with a yield of 80.6%.

[0055] The NMR information of the obtained product is as follows, as can be seen from the NMR information, R 1 is trifluoromethyl; R 2 The ligand for phenyl was synthesized successfully.

[0056] 1 H NMR (400 MHz, CDCl 3 ) δ 12.74 (s, 1H, O H ), 8.08 (d, J = 7.0 Hz, 2H,Ar– H ), 7.53 (d, J = 7.0 Hz, 2H, Ar– H ), 7.42(m, 3H, Ar– H), 7.17 (d, J = 6.2Hz, 2H, Ar– H ), 6.52 (s, 1H, C H ), 4.48 (m, 1H, NC H), 3.92 (m, 1H, =NC H 2 ), 2.57(m, 1H, C H 2 ), 2.10 (m, 5H, C H 2 ), 1.54 (m, 2H...

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Abstract

The invention discloses a chiral aluminum complex containing acetylacetone derivative and a preparation method and application thereof; the chiral aluminum complex has a structural formula shown as formula I that is shown in the description, wherein R1 is trifluoromethyl or methyl, and R2 is phenyl, trifluoromethyl or methyl. The chiral aluminum complex as a catalyst is acquired by subjecting a ligand and trimethylaluminum to reaction; the preparation method is simple, the cost is low, and product yield is high; the chiral aluminum complex has special structure that is variable; divalent N,N,O,O coordination of metallic center aluminum and the ligand may serve as the catalyst for cyclic lactone ring opening polymerization; the catalyst has high catalytic activity, good stereo-selectivity and high reaction speed; polymerization is simple to perform, an obtained polymer has narrow molecular weight distribution, controllable molecular weight and high yield and is widely applicable to cyclic lactone ring opening polymerization and is a very ideal catalyst.

Description

technical field [0001] The invention relates to a chiral aluminum complex containing acetylacetone derivatives and a preparation method thereof, and also relates to the application of the chiral aluminum complex containing acetylacetone derivatives as a catalyst for ring-opening polymerization of cyclic lactones. Background technique [0002] Traditional polymer materials using petroleum as raw materials have penetrated into all aspects of economy and life. Traditional polymer materials degrade very slowly under natural conditions. While they bring convenience to people's lives, their use waste constitutes a huge amount. "White garbage" has seriously polluted the ecological environment, and in the case of petroleum being depleted as a non-renewable resource, the rapid development of polymer materials that rely on petroleum raw materials is greatly restricted. Traditional polymer materials are facing the two major problems of energy crisis and environmental pollution. Finding...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/06C08G63/84
CPCC07F5/069C08G63/823
Inventor 王传旭姚伟高爱红张永芳
Owner 新泰中学
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