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Method for Catalyzing Lactide Polymerization Using Asymmetric Aluminum Complex Containing Acetylacetone Derivatives

A technology of acetylacetone and aluminum complexes, which is applied to compounds containing elements of Group 3/13 of the periodic table, chemical instruments and methods, organic chemistry, etc. The effect of narrow distribution, high stereoselectivity and high product yield

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

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Problems solved by technology

[0002] Traditional plastics based on petroleum have unparalleled advantages, but there are two fatal disadvantages: non-renewable and non-degradable

Method used

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  • Method for Catalyzing Lactide Polymerization Using Asymmetric Aluminum Complex Containing Acetylacetone Derivatives
  • Method for Catalyzing Lactide Polymerization Using Asymmetric Aluminum Complex Containing Acetylacetone Derivatives
  • Method for Catalyzing Lactide Polymerization Using Asymmetric Aluminum Complex Containing Acetylacetone Derivatives

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] The structural formula of the synthesized ligand is the above formula (A), where R 1 is methyl; R 2 For methyl, the reaction process is: Add 0.30 g of ethylenediamine (a) with unilateral protection and equimolar amount of acetylacetone into 12 mL of methanol, heat and reflux for 12 hours, cool, filter and wash with cold methanol after the reaction , filtered, collected, dried and weighed to obtain 0.35 g of solid, with a yield of 81.4%.

[0045] 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.

[0046] 1 H NMR (400 MHz, CDCl 3 ) δ 10.85 (s, 1H, O H ), 8.03 (d, J = 6.4Hz, 2H,Ar– H ), 7.56 (d, J = 6.4Hz, 2H, Ar– H ), 5.23 (s, 1H, C H ), 4.25 (m, 2H, NC H 2 ),3.42 (m, 2H, =NC H 2 ), 2.08 (s, 6H, C H 3 ). HRESI-MS: m / z ccld. C 15 h 16 N 2 o 3 [M-H] - ;271.1085, found: 271.1090.

Embodiment 2

[0048] The structural formula of the synthesized ligand is the above formula (A), where R 1 is methyl; R 2 It is trifluoromethyl, and the reaction process is as follows: Add 0.20 g of ethylenediamine (a) with unilateral protection and equimolar amount of trifluoroacetylacetone into 10 mL of methanol, heat and reflux for 12 hours, cool and filter after the reaction is completed and use Washed with cold methanol, filtered, collected, dried and weighed to obtain 0.30 g of solid, yield 88.2%.

[0049] 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.

[0050] 1 H NMR (400 MHz, CDCl 3 ) δ 11.25 (s, 1H, O H ), 8.05 (d, J = 6.6 Hz, 2H,Ar– H ), 7.58 (d, J = 6.6 Hz, 2H, Ar– H ), 5.62 (s, 1H, C H ), 4.26 (m, 2H, NC H 2 ),3.45 (m, 2H, =NC H 2 ), 2.09 (s, 3H, C H 3 ). HRESI-MS: m / z cacld.C 15 h 12 f 3 N 2 o 3 F[M-H] - ; 325.0802, fo...

Embodiment 3

[0052] The structural formula of the synthesized ligand is the above formula (A), where R 1 is trifluoromethyl; R 2 is phenyl, the reaction process is: Add 0.25 g of ethylenediamine (a) with unilateral protection and equimolar amount of benzoyltrifluoroacetone into 20 mL of methanol, heat and reflux for 12 hours, cool and filter after the reaction and use Washed with cold methanol, filtered, collected, dried and weighed to obtain 0.45 g of solid, yield 88.2%.

[0053] 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.

[0054] 1 H NMR (400 MHz, CDCl 3 ) δ 12.05 (s, 1H, O H ), 8.07 (d, J = 6.8 Hz, 2H,Ar– H ), 7.60 (d, J = 6.8 Hz, 2H, Ar– H ), 7.56-7.47(m, 3H, Ar– H), 7.19 (d, J =6.0 Hz, 2H, Ar– H ), 6.47 (s, 1H, C H ), 4.34 (m, 2H, NC H 2 ), 3.92 (m, 2H, =NC H 2 ). HRESI-MS: m / z cacld.C 20 h 15 f 3 N 2 o 3 [M-H] - ; 387...

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Abstract

The invention discloses a method for catalyzing the polymerization of lactide by using an asymmetric aluminum complex containing acetylacetone derivatives, which comprises the following steps: mixing a catalyst, an organic solvent, a benzyl alcohol auxiliary agent and lactide, and The ring-opening polymerization reaction is carried out under the protection of oxygen and inert gas, and after the reaction, the reactants are processed to obtain polylactide; the catalyst is an asymmetric aluminum complex containing acetylacetone derivatives. The invention uses the asymmetric aluminum complex containing acetylacetone derivatives as the catalyst, benzyl alcohol as the co-catalyst, has good reaction controllability, high stereoselectivity of the catalyst, and the obtained polylactide has controllable molecular weight and high yield, and has the advantages of Excellent physical and chemical properties can meet the needs of the market.

Description

technical field [0001] The invention relates to a lactide polymerization method, in particular to a lactide polymerization method catalyzed by an asymmetric aluminum complex containing acetylacetone derivatives. Background technique [0002] Traditional plastics based on petroleum have unparalleled advantages, but there are two fatal disadvantages: non-renewable and non-degradable. Under the situation that petroleum is facing depletion as a non-renewable resource, the rapid development of polymer materials that rely on petroleum raw materials is greatly restricted, and polymer materials are difficult to degrade, and a large amount of polymer waste has been accumulated in real life for a long time. The pollution caused by human living environment is gradually increasing. Therefore, it is very urgent to find renewable resources to replace petroleum. [0003] Because polyester is non-toxic, non-irritating, and has good biocompatibility, polyester is a biodegradable and enviro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G63/84C08G63/08C07F5/06
CPCC07F5/066C08G63/08C08G63/823
Inventor 王洪宾姚伟高爱红张永芳
Owner TAISHAN MEDICAL UNIV
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