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Method for Catalyzing Caprolactone Polymerization Using Aluminum Complex Containing Salicylaldehyde Group

A technology of aluminum complex and caprolactone, applied in the direction of organic chemistry, can solve the problems of non-renewability and non-degradability, and achieve the effect of diverse catalyst structure, high stereoselectivity and high stereoselectivity

Active Publication Date: 2020-09-29
UNIV OF JINAN
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  • Abstract
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  • Application Information

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Problems solved by technology

[0002] Petroleum-based traditional plastics have had a great influence in the industry since the 1940s. These traditional plastics have unparalleled advantages, but there are two fatal disadvantages: non-renewable and non-degradable

Method used

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  • Method for Catalyzing Caprolactone Polymerization Using Aluminum Complex Containing Salicylaldehyde Group
  • Method for Catalyzing Caprolactone Polymerization Using Aluminum Complex Containing Salicylaldehyde Group
  • Method for Catalyzing Caprolactone Polymerization Using Aluminum Complex Containing Salicylaldehyde Group

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] The structural formula of the synthesized ligand is the above formula (A), where R is hydrogen, and the reaction process is as follows: add 0.20 g of ethylenediamine (a) with unilateral protection and an equimolar amount of salicylaldehyde into 10 mL of methanol, and heat to reflux for reaction After 12 hours, after the reaction was completed, it was cooled and filtered, washed with cold methanol, filtered, collected, dried and weighed to obtain 0.27 g of solid, with a yield of 87.1%.

[0044] The product obtained is characterized, and the results are as follows:

[0045] 1 H NMR (400 MHz, CDCl 3 ) δ 12.85 (s, 1H, O H ), 8.26 (s, 1H, Ar H C=N),7.80 (d, J = 5.4 Hz, 2H, Ar– H ), 7.68 (d, J = 5.4Hz, 2H, Ar– H ), 7.24–7.16 (m,1H, Ar– H ), 7.11 (m, 1H, Ar– H ), 6.97 (d, J = 8.3 Hz, 1H, Ar– H ), 6.75 (td, J =7.5, 1.0 Hz, 1H, Ar– H ), 4.20 (m, 2H, NC H 2 ), 4.10 (m, 2H, NC H 2 ). HRESI-MS: m / zcacld. C 17 h 14 N 2 o 3 [M-H] - ; 293.0927, found: 293....

Embodiment 2

[0048] The structural formula of the synthesized ligand is the above formula (A), wherein R is a methyl group, and the reaction process is as follows: add 0.25 g of ethylenediamine (a) with unilateral protection and an equimolar amount of 3,5-dimethyl salicylaldehyde In 20 mL of methanol, heat to 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 90.5%.

[0049] The product obtained is characterized, and the results are as follows:

[0050] 1 H NMR (400 MHz, CDCl 3 ) δ 12.61 (s, 1H, O H ), 8.20 (s, 1H, Ar H C=N),7.73 (d, J = 5.5 Hz, 2H, Ar– H ), 7.66 (d, J = 5.4 Hz, 2H, Ar– H ), 6.96 (s, 1H,Ar– H ), 6.75 (s, 1H, Ar– H ), 4.31– 4.28(m, 2H, NC H 2 ), 4.20–4.15 (m, 2H, NC H 2 ),2.17 (s, 3H, C H 3 ), 2.15 (s, 3H, C H 3 ). HRESI-MS: m / z cacld.C 19 h 18 N 2 o 3 [M-H] - ;321.1238, found: 321.1236.

[0051] It can be seen from the above characteriza...

Embodiment 3

[0053] The structural formula of the synthesized ligand is the above formula (A), where R is bromine, and the reaction process is as follows: add 0.22 g of ethylenediamine (a) with one side protection and 3,5-dibromosalicylaldehyde in an equimolar amount to 15 mL In methanol, heat to reflux for 12 hours. After the reaction, cool and filter and wash with cold methanol, filter, collect, dry and weigh to obtain 0.46 g of solid, with a yield of 88.5%.

[0054] The product obtained is characterized, and the results are as follows:

[0055] 1 H NMR (400 MHz, CDCl 3 ) δ 13.90 (s, 1H, O H ), 8.19 (s, 1H, Ar H C=N),7.82–7.74(m, 2H, Ar– H ), 7.67–7.60 (m, 2H, Ar– H ), 7.54 (s, 1H, Ar– H ), 7.15 (s,1H, Ar– H ), 4.30–4.27 (m, 2H, NC H 2 ), 4.25–4.20 (m, 2H, NC H 2 ). HRESI-MS: m / zcacld.C 17 h 12 Br 2 N 2 o 3 [M-H] - ; 448.9136, found: 448.9138.

[0056] It can be seen from the above characterization results that the obtained product is the ligand in which R is bromin...

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Abstract

The invention discloses a method for catalyzing caprolactone polymerization by utilizing an aluminum complex containing a salicylaldehyde group. The method comprises the following steps: mixing a catalyst, an organic solvent, benzyl alcohol co-catalyst and caprolactone, carrying out ring opening polymerization reaction under the protection of anhydrous oxygen-free and inert gas, and then treatingthe reaction product to obtain polycaprolactone. According to the method disclosed by the invention, the self-developed aluminum complex containing the salicylaldehyde group is used as a catalyst to carry out the ring-opening polymerization reaction of caprolactone, the preparation method of the salicylaldehyde-containing aluminum complex catalyst is simple, the cost is low, the product yield is high, and the structure of the catalyst is diversified, the metal center aluminum coordinates with two-valent N,N,O,O of the ligand, the calytic activity is high, the stereoselectivity and the reactionrate are high, and the obtained polymer is a benzyloxy-terminated polymer, the molecular weight distribution is narrow, the molecular weight is controllable, the yield is high, and the market demandis met.

Description

technical field [0001] The invention relates to a method for catalyzing the polymerization of caprolactone, in particular to a method for catalyzing the polymerization of caprolactone by using an aluminum complex containing a salicylaldehyde group. Background technique [0002] Traditional plastics based on petroleum have had a great influence in the industry since the 1940s. These traditional plastics have unparalleled advantages, but there are two fatal disadvantages: non-renewability and non-degradability. Under the situation that petroleum is facing depletion as a non-renewable resource, the rapid development of polymer plastic materials that rely on petroleum raw materials is greatly restricted, and polymer polymer plastic materials are difficult to degrade, and a large amount of polymer polymer plastic material waste has been accumulated in reality for a long time The pollution caused to the living environment of human beings in daily life is gradually increasing. Fin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G63/84C08G63/08C07D209/48
CPCC07D209/48C08G63/823
Inventor 姚伟高爱红张永芳王洪宾
Owner UNIV OF JINAN
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