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Bridged diamidine-based zinc catalyst and preparation method and application thereof

A catalyst, zinc amidinate technology, applied in the field of transition metal catalysts for lactide polymerization, can solve the problems of PLA limitation, aluminum ion cannot be metabolized, and limit the application of PLA, and achieve the effect of low price, high yield and simple preparation method

Inactive Publication Date: 2012-01-18
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the strong toxicity of most tin compounds, the medical application of PLA prepared by stannous octoate is greatly limited; and aluminum ions cannot be metabolized in humans or animals, and are suspected to cause Alzheimer's disease , therefore, PLA prepared by these two catalysts also has many limitations

Method used

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  • Bridged diamidine-based zinc catalyst and preparation method and application thereof
  • Bridged diamidine-based zinc catalyst and preparation method and application thereof
  • Bridged diamidine-based zinc catalyst and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Preparation and characterization of embodiment 1 catalyst 2a

[0015] (1) Preparation of lithium salt

[0016] Under the protection of nitrogen and ice water bath, dimethylsilyl bridged diphenylamine (6.0g, 24.8mmol) was dissolved in ether (200cm 3 ), under stirring, slowly add LiBu n n-hexane solution (2.8mol dm -3 , 17.7cm 3 , 49.6mmol), after the reaction mixture returned to room temperature, continued to stir for 2 hours, cooled the reaction solution to 0°C, and added PhCN (5.06cm 3 , 49.6mmol), after the reaction mixture returned to room temperature, continued to stir for 5 hours, and recrystallized the white solid obtained after the reaction with tetrahydrofuran to obtain a yellow crystalline bridging bis-amidine ligand lithium salt 1a.

[0017] (2) Dissolve the bridged bisamidine lithium compound 1a (2.05g, 2.44mmol) in tetrahydrofuran (ca. 30mL) to obtain a yellow clear liquid, and slowly add anhydrous dichloro Zinc chloride (0.335g, 2.44mmol), after the re...

Embodiment 2

[0022] 1. The preparation of catalyst 2a is the same as in Example 1.

[0023] 2. Lactide polymerization: Dissolve lactide (0.81g, 5.62mmol) in 3% n-butanol in tetrahydrofuran (20mL), and then add bridged bisamidinyl zinc catalyst 2a (0.053g, 0.0562mmol) , the ratio of catalyst to lactide is 1:100, react for 24 hours, drop a few drops of analytically pure hydrochloric acid into the reaction solution to terminate the reaction, then slowly add ethanol to the solution, a large amount of white insoluble matter will appear, after standing Filter and drain the solvent to obtain a colorless transparent jelly, which is polylactic acid product. Conversion rate 84.8%

Embodiment 3

[0025] 1. The preparation of catalyst 2a is the same as in Example 1.

[0026] 2. Lactide polymerization: Dissolve lactide (0.875g, 6.08mmol) in tetrahydrofuran solution (20mL), then add bridged bisamidinyl zinc catalyst 2e (0.057g, 0.0608mmol), catalyst and lactide The ratio is 1:100, react for 24 hours, drop a few drops of analytically pure hydrochloric acid into the reaction solution to terminate the reaction, then slowly add ethanol to the solution, a large amount of white insoluble matter will appear, filter after standing, and drain the solvent to obtain The colorless transparent jelly is a polylactic acid product. Conversion rate 89.8

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Abstract

The invention provides a bridged diamidine-based zinc catalyst, which relates to a lactide ring opening polymerization catalyst, in particular to a catalyst of a diamidine-based ligand zinc composition having the N-C-N-Si-N-C-N characteristic and taking zinc as a central atom. A preparation method of the catalyst comprises the following steps of: transforming butyl lithium into a dilithium salt by taking bridged diamine as an initial raw material under the protection of nitrogen gas; adding cyanophenyl for undergoing an addition reaction; transferring a silicon base twice to form a bridged diamidine-based ligand; and reacting the ligand with zinc dichloride to obtain the catalyst. The synthesis method has the advantages of general applicability, mild reaction condition, simple and readily-available materials, low cost, simple steps and high yield. A compound has high catalytic activity on a ring opening polymerization reaction of lactide and good application prospect.

Description

technical field [0001] The invention relates to a lactide polymerization transition metal catalyst, in particular to a bridged bisamidinyl zinc catalyst with an N-C-N-Si-N-C-N skeleton, a preparation method and application thereof. Background technique [0002] Polylactic acid (PLA) is an important derivative of lactic acid because it is non-toxic, biodegradable, and has good biocompatibility. Ring-opening polymerization of lactide is a common method for preparing high molecular weight PLA. The catalysts currently being used in industry mainly include stannous octoate and aluminum triisopropoxide. However, due to the strong toxicity of most tin compounds, the medical application of PLA prepared by stannous octoate is greatly limited; and aluminum ions cannot be metabolized in humans or animals, and are suspected to cause Alzheimer's disease , Therefore, PLA prepared by these two catalysts also has many limitations. Zinc is an essential trace element for the human body, an...

Claims

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Application Information

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IPC IPC(8): C08G63/83C08G63/08C07F19/00
Inventor 白生弟关飞刘瑞琴刘滇生
Owner SHANXI UNIV
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