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Synthesis, Characterization and Application of a Novel Type of Organosoluble Chiral Zirconium Phosphonates

Author: LiuJin
Tutor: MaXueBing
School: Southwestern University
Course: Organic Chemistry
Keywords: organosolubility Zirconium phosphonate Homogeneous catalysis and two-phase separation Asymmetric catalysis Diethylzinc
CLC: O643.36
Type: Master's thesis
Year: 2008
Downloads: 2
Quote: 0
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Abstract


A series of zirconium phosphonates had been synthesized by several steps of esterification,Grinard reagent,amino pretection,reduction,Mannich reaction and hydrolysis using L（or D）-phenylalanine,L（or D）-phenylethylamine as raw materials,in which chiralβ-amino alcohols were covalently linked to the backbone of zirconium phosphonate,and the structure and morphology of zirconium phosphonates had been characterized by IR,XPRD,TG,elemental analysis,31P NMR,SEM and TEM.This type of zirconium phosphonates（5a-b,10a-d）had good organosolubility in organic solvents such as toluene,tetrahydrofunan and trichloromethane.The organic moieties in zirconium phosphonates played an important role in determining the type of solvent.If the stirred time above 10 h continued at 80℃in the preparation of zirconium phosphonates,it was found that the organosoluble zirconium phosphonates became insoluble,which was attributed to the conversion of nanocomposite filiform molecular structure to laryered and mesoporous banckbone.Due to the organosolubility of zirconium phosphonates in organic solvents such as toluene and tetrahydrofunan,the catalytic addition of diethylzinc to benzaldehyde can proceed in homogeneous phase to realize the homogeneous catalysis by using the inorganic material-supported catalyst,in which the 80-90%yield and 14-31%ee enantioselectivity had been obtained.The optium catalytic condition was that the molar ratio of benzaldehyde to diethylzinc was 1 to 2,and 10 molar percent of catalyst was used and stirred for 72 h at room temperature.After the catalytic reaction was completed and the solvent such as petroleum ether or cyclohexane was added,the zirconium phosphonates could work up and be recycled by filtration or centrifugation to realize the liquid/solid two-phase separation and the reuse of zirconium phosphonates.

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CLC: > Mathematical sciences and chemical > Chemistry > Physical Chemistry ( theoretical chemistry ),chemical physics > Chemical kinetics,catalysis > Catalytic > Catalyst
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