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Aluminium alkyl coordination complexes containing N,N,N,N-tetradentate chelate pentacoordinate ligands, preparation method of aluminium alkyl coordination complexes and method for catalyzing ring opening polymerization of lactide

A technology of alkylaluminum and complexes, which is applied in the field of catalytic lactide ring-opening polymerization, can solve the problems of no activity and low activity, and achieve the effects of simple operation, low cost and simple process

Active Publication Date: 2017-10-24
北京朗净汇明生物科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] There are also reported N, N bidentate or N, N, N tridentate chelated aluminum complexes, but their activity in the ring-opening polymerization of lactide is not high or has no activity

Method used

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  • Aluminium alkyl coordination complexes containing N,N,N,N-tetradentate chelate pentacoordinate ligands, preparation method of aluminium alkyl coordination complexes and method for catalyzing ring opening polymerization of lactide
  • Aluminium alkyl coordination complexes containing N,N,N,N-tetradentate chelate pentacoordinate ligands, preparation method of aluminium alkyl coordination complexes and method for catalyzing ring opening polymerization of lactide
  • Aluminium alkyl coordination complexes containing N,N,N,N-tetradentate chelate pentacoordinate ligands, preparation method of aluminium alkyl coordination complexes and method for catalyzing ring opening polymerization of lactide

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preparation example Construction

[0031] In the preparation method provided by the present invention, the specific type of solvent can be selected within a wide range, but from the viewpoint of the cost of preparation, preferably, the solvent is selected from at least one of tetrahydrofuran, dichloromethane and toluene, preferably tetrahydrofuran .

[0032] In addition, in the above preparation method, the order of addition of the materials can be selected within a wide range, but considering the yield of the target product, preferably, in the preparation method, the order of addition of the materials is: The bisindole ligand is mixed with a solvent to form a ligand solution; then in the presence of a protective gas, the AlR 3 The solution is added dropwise to the ligand solution;

[0033] After the above-mentioned coordination reaction is completed, the purification method of the product can be selected in a wide range, but in order to simplify the purification steps and increase the purification yield, preferably...

preparation example 1

[0046] Preparation:

[0047] Dissolve indole 2-carboxaldehyde (30.0 mmol), 1,3-propanediamine (15.0 mmol), and p-toluenesulfonic acid (0.03 mmol) in 10 mL ethanol, react at 25°C for 12 hours, filter with suction, and wash with a small amount of cold ethanol Three times, vacuum drying, to obtain the bisimine bridged bisindole ligand with the structure shown in formula (B1).

[0048] The characterization data of the product are: 1 H NMR (500MHz, CDCl3): δ9.68 (s, 2H), 8.26 (s, 2H), 7.64 (d, J = 7.5 Hz, 2H), 7.30 (d, J = 8.0 Hz, 2H), 7.24 ( t,J=8.0Hz,,2H), 7.11(t,J=7.5Hz,2H), 6.75(s,2H), 3.76-3.74(m,4H), 2.10-2.05(m,2H); 13 C NMR (75MHz, CDCl3): δ153.2, 137.3, 135.0, 128.0, 124.4, 121.8, 120.1, 111.6, 108.1, 58.4, 32.4; HRMS (APCI) m / z: calcd for C 21 H 21 N 4 (M+H + ) 329.1761; Found: 329.1764.

preparation example 2

[0050] Preparation:

[0051] The bisimine bisindole ligand with the structure shown in formula (B2) was prepared according to the method of Preparation Example 1, except that 1,3-propanediamine was replaced with ethylenediamine.

[0052] The characterization data of the product are: 1 H NMR(500MHz, CDCl 3 ): δ9.54(s, 2H), 8.23(s, 2H), 7.62(d,J=8.0Hz,2H), 7.33(d,J=8.0Hz,2H), 7.24(t,J=8.0Hz ,,2H), 7.09(t,J=7.5Hz,2H), 6.74(s,2H),3.92(s,3H); 13 C NMR(75MHz, CDCl 3 ):δ 154.2,137.3,135.1,128.0,124.4,121.8,120.1,111.6,108.2,60.9; HRMS(APCI) m / z:calcd for C 20 H 19 N 4 (M+H + ) 315.1604; Found: 315.1601.

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Abstract

The invention discloses aluminium alkyl coordination complexes containing N,N,N,N-tetradentate chelate pentacoordinate ligands, a preparation method of the aluminium alkyl coordination complexes and a method for catalyzing ring opening polymerization of lactide. The structure of the aluminium alkyl coordination complexes is shown as formula (A) in the description, wherein in the formula, R is C1-C6 hydrocarbyl, and R1 is C1-C10 hydrocarbyl. The aluminium alkyl coordination complexes with excellent catalytic performance can be prepared with the preparation method and can catalyze ring opening polymerization of lactide, and the preparation method has the advantages of simple operation, low equipment requirement and high yield.

Description

Technical field [0001] The present invention relates to an alkyl aluminum complex, in particular to an alkyl aluminum complex containing N,N,N,N-tetradentate chelate pentacoordination, a preparation method thereof and a method for catalyzing the ring-opening polymerization of lactide. Background technique [0002] Because polylactide (PLA) has biocompatibility and degradability and its monomers can be obtained from renewable resources, it is used in controlled and sustained release systems for drugs, absorbable sutures, food packaging and apparel products It has a wide range of applications. In the ring-opening polymerization of lactide, in order to achieve the controllability, stereoselectivity and high activity of the catalyst, a variety of metal alkoxide compounds are used to study such catalytic reactions. These metals include aluminum. , Zinc, tin, magnesium, calcium and lanthanide rare earth metals. Among them, the compound containing metallic aluminum has been widely app...

Claims

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Application Information

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IPC IPC(8): C07F5/06C08G63/84
CPCC07B2200/13C07F5/066C08G63/823
Inventor 韦芸王绍武周双六王华
Owner 北京朗净汇明生物科技有限公司
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