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Schiff base aluminum compound, preparation method thereof and preparation method of polylactic acid

A technology of Schiff base aluminum and compound, which is applied in the preparation of polylactic acid, Schiff base aluminum compound and its preparation field, can solve the problems of catalytic reaction selectivity and low activity, achieve selectivity enhancement, enhance reaction activity, improve active effect

Active Publication Date: 2012-11-21
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reported catalysts are all single-metal center Schiff bases obtained by the reaction of salicylaldehyde or substituted salicylaldehyde with diamines, and the selectivity and activity of the catalytic reaction are relatively low.

Method used

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  • Schiff base aluminum compound, preparation method thereof and preparation method of polylactic acid
  • Schiff base aluminum compound, preparation method thereof and preparation method of polylactic acid
  • Schiff base aluminum compound, preparation method thereof and preparation method of polylactic acid

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preparation example Construction

[0048] Optionally, when R is -CH 3 or -CH 2 CH 3 , the present invention also provides a method for preparing a Schiff base aluminum compound, comprising the following steps: combining the Schiff base with the structure of formula (II) and Al(R′) 3 React in a solvent to obtain the Schiff base aluminum compound with the structure of formula (III). Wherein, the solvent is an organic solvent well known to those skilled in the art, preferably tetrahydrofuran or toluene.

[0049] R 1 and R 2 The choice of influences the choice of solvent, when R 1 and R 2 independently selected from -H, -F, -Cl, -Br or -NO 2 When, the reaction solvent is preferably tetrahydrofuran, when R 1 and R 2 independently selected from -CH 3 、-CH 2 CH 3 、-CH(CH 3 ) 2 、-C(CH 3 ) 3 When, the reaction solvent is preferably toluene.

[0050]

[0051] R 1 and R 2 independently selected from -H, -CH 3 、-CH 2 CH 3 、-CH(CH 3 ) 2 、-C(CH 3 ) 3 , -F, -Cl, -Br or -NO 2 ;

[0052] R' is -CH...

Embodiment 1

[0074] The preparation of embodiment 1 pentaerythramine

[0075] 1.1 Stir 13.6g of pentaerythritol and 100ml of pyridine in an ice bath, slowly add 51.5g of methanesulfonyl chloride, and react for 3 hours, pour the reaction solution into a mixture of 200ml of concentrated hydrochloric acid, 400ml of water and 1000ml of methanol, filter, and separate After washing with water and methanol three times, it was sucked dry to obtain compound VIa.

[0076]1.2 Slowly heat 11.2g of the compound VIa obtained in 1.1, 500ml of DMSO and 10g of sodium azide to 100°C while stirring, and after 25 hours of reaction, pour the reaction system into 600ml of water, extract three times with petroleum ether, and combine the organic phases , washed three times with water, dried over anhydrous magnesium sulfate, filtered, and the organic solvent was removed by rotary evaporation to obtain white crystals as compound VIb.

[0077] 1.3 Under the conditions of ice bath and argon protection, add 1.5g of l...

Embodiment 2

[0078] Embodiment 2 structural formula is the synthesis of the Schiff base IIa of II

[0079] IIa: R 1 =R 2 =-H

[0080] Dissolve 1.32g of the pentaerythramine obtained in 1.3 in 20ml of ethanol, slowly dropwise add 50ml of ethanol containing 4.88g of salicylaldehyde, reflux for 14h, remove most of the solvent by rotary evaporation, filter to obtain a yellow powder, mix with chloroform and ethanol Solvent washing affords the Schiff base IIa.

[0081] Utilize nuclear magnetic resonance to analyze the Schiff base IIa obtained in embodiment 2, obtain its hydrogen spectrum, the result is as follows:

[0082] 1 H NMR (300.00MHz, d 6 -DMSO): δ=13.24(s, OH 4H), 8.61(s, NCH 4H), 7.45, 6.86(m, PhH 16H), 3.76(s, CCH 2 N 8H).

[0083] The Schiff base IIa obtained in Example 2 was analyzed by elemental analysis to obtain the content of each atom.

[0084] Elem. Anal. (%): Calcd. C 72.24; H 5.88; N 10.21. Found: C 72.13; H 5.81; N 10.20.

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Abstract

The invention provides a Schiff base aluminum compound, a preparation method thereof and a preparation method of polylactic acid. The formula (I) of the Schiff base aluminum compound is shown in the description. Compared with the metal-centered Schiff base in the prior art, tetramine compounds are used to connect four C=N functional groups, so that two metal active center binding sites are provided to form the double-metal-centered Schiff base. The double-metal-centered Schiff base has larger molecular space and larger steric hindrance, so that selectivity of lactide ring opening polymerization of the double-metal-centered Schiff base is improved, and spacially structural regularity of polymerizate is improved; reaction activity of the catalyst is improved by introducing the double metal centers, and activity of polymerization reaction is improved.

Description

technical field [0001] The invention belongs to the field of catalysts, and in particular relates to a Schiff base aluminum compound, a preparation method thereof, and a preparation method of polylactic acid. Background technique [0002] Polylactic acid is a chemically synthesized biodegradable material, which is widely used in packaging materials, biomedicine and pharmaceutical industries. The synthesis of polylactic acid usually adopts two methods, namely, ring-opening polymerization of lactide (a cyclic dimer of lactic acid) and direct polymerization of lactic acid. Among them, polylactic acid of macromolecule generally adopts the method of ring-opening polymerization of lactide, and a large number of documents and patents have carried out relevant reports on the ring-opening polymerization of lactide, such as U.S. Patent No. 5235031 and U.S. Patent No. 5357034 US patent. [0003] Lactide is divided into three stereoisomers: L-lactide (LLA), D-lactide (DLA) and meso-la...

Claims

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Application Information

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IPC IPC(8): C08G63/84C08G63/08
Inventor 庞烜曲智段然龙张涵陈学思庄秀丽
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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