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Chiral aluminum compound and preparation method thereof and preparation method of polylactic acid

A technology of aluminum compound and polylactic acid, which is applied in the field of preparation of polylactic acid, chiral aluminum compound and its preparation, can solve the problems of low selectivity and activity

Active Publication Date: 2013-12-04
普立思生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the reported catalysts all catalyze the ring-opening polymerization of lactide with low selectivity and activity.

Method used

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  • Chiral aluminum compound and preparation method thereof and preparation method of polylactic acid
  • Chiral aluminum compound and preparation method thereof and preparation method of polylactic acid
  • Chiral aluminum compound and preparation method thereof and preparation method of polylactic acid

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preparation example Construction

[0049] Optionally, when R is -CH 3 or -CH 2 CH 3 When, the present invention also provides a preparation method of a chiral aluminum compound, comprising the following steps: combining the chiral ligand with the structure of formula (II) with Al(R′) 3 React in a solvent to obtain a chiral 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.

[0050] R 1 , R 2 , R 3 and R 4 The choice of influences the choice of solvent, when R 1 , R 2 , R 3 and R 4 independently selected from -H, -F, -Cl, -Br or -NO 2 When, the reaction solvent is preferably tetrahydrofuran, when R 1 , R 2 , R 3 and R 4 independently selected from -CH 3 、-CH 2 CH 3 、-CH(CH 3 ) 2 、-C(CH 3 ) 3 When, the reaction solvent is preferably toluene.

[0051]

[0052]

[0053] R 1 , R 2 , R 3 and R 4 independently selected from -H, -CH 3 、-CH 2 CH 3 、-CH(CH 3 ) ...

Embodiment 1

[0074] Embodiment 1 structural formula is the synthesis of the ligand IIa of II

[0075] IIa: R1=R2=R3=R4=-H

[0076] Under nitrogen atmosphere, dissolve 0.09g of palladium acetate and 0.50g of binaphthyl diphenylphosphine in 50mL of toluene, slowly add 1.50g of 2-bromoanisole and 2.27g of S-type or R-type 2,2'-diamino-1 , 1'-binaphthyl, stirred at room temperature for 5 minutes, added 1.152g of sodium tert-butoxide, stirred at room temperature for 10 minutes, then placed in a 70°C oil bath and stirred for 6 hours, cooled to room temperature, added 60mL of ether, washed with saline, and separated Afterwards, sodium carbonate was dried, concentrated, and the obtained crude product was separated by column chromatography, and the eluent was hexane:ethyl acetate (volume ratio of 10:1), which included 2% triethylamine, and the obtained product was colorless Solid VIa;

[0077] Dissolve VIa (0.390g, 1.00mmol) and salicylaldehyde (0.122g, 1.00mmol) in 10ml of ethanol, heat to reflu...

Embodiment 2

[0084] Embodiment 2 structural formula is the synthesis of the ligand IIb of II

[0085] IIbR1=-F, R2=R3=R4=-H,

[0086] Under a nitrogen atmosphere, dissolve 0.090 g of palladium acetate and 0.50 g of binaphthyl diphenylphosphine in 50 mL of toluene, slowly add 1.64 g of 2-bromo-5-fluoroanisole and 2.27 g of S-type or R-type 2,2'- Diamino-1,1'-binaphthyl, stirred at room temperature for 5 minutes, then added 1.15g of sodium tert-butoxide, stirred at room temperature for 10 minutes, then placed in a 70°C oil bath for 6 hours, cooled to room temperature, added 60mL of ether, washed with saline After washing and separating, dry with sodium carbonate and concentrate, the obtained crude product is separated by column chromatography, the eluent is hexane:ethyl acetate (volume ratio is 10:1), which includes 2% triethylamine, and finally obtains The product is a colorless solid VIb;

[0087] Dissolve VIb (0.408g, 1.00mmol) and salicylaldehyde (0.122g, 1.00mmol) in 10ml of ethanol, ...

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Abstract

The invention provides a chiral aluminum compound and a preparation method thereof and a preparation method of polylactic acid. The structure of the chiral aluminum compound is shown as a formula (I). In the structural formula (I), on one hand, a chiral molecule has relatively large molecular space and obtains relatively large spatial steric hindrance, so that the selectivity of the chiral molecule for ring opening polymerization of lactide is enhanced and the regularity of the spatial structure of a polymerization product is improved, and on the other hand, with metal aluminum as a central atom, the reactivity of a catalyst is enhanced and the activity of polymerization reaction is improved. The invention further provides the preparation method of the polylactic acid. The polylactic acid obtained by catalyzing racemic lactide with the chiral aluminum compound is polylactic acid with isotactic components as predominant components, and the isotactic components account for 0.64.

Description

technical field [0001] The invention belongs to the field of catalysts, and in particular relates to a chiral aluminum compound, a preparation method thereof, and a preparation method of polylactic acid. Background technique [0002] Polylactic acid is a biodegradable polymer material prepared by chemical methods, 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. Wherein the polylactic acid of high molecular weight is generally obtained by the method for ring-opening polymerization of lactide, and a large amount of documents and patents have carried out relevant reports to the ring-opening polymerization of lactide now, as the U.S. patent that the patent publication number is 5235031 and U.S. Patent Publication No. 5,357,034. [0003] Lactide is divided int...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/06C08G63/08C08G63/84
Inventor 庞烜高波段然龙曲智李想庄秀丽陈学思
Owner 普立思生物科技有限公司
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