Prepartion Of Cyclodextrin Derivatives As Chiral Stationary Phases And Study On Their Enantiosperation Of Chiral Insecticide's Intermediate

The separation of enantiomers has become very important in chiral insecticides study. Capillary gas chromatography using chiral stationary phase is a simple and convenient way for enantioseparation and a powerful tool among many analysis methods.The purpose of study is to investigate the synthesis and application of new cyclodextrin derivatives as stationary phase on separation of chiral insecticide's intermediates. The work can be divided into two parts:Firstly, after reviewing the importance of cyclodextrin derivatives(CDs) as stationary phase in capillary gas chromatography and the advance in separtion of chiral insecticides, we find it is probable to separte the chiral insecticides by modifying the CDs' structure. So, two series of CDs (total seven compounds) are designed and prepared, according to the fundmental principle designing for chiral stationary phase. The structures of these compounds are confirmed by IR and 'HNMR, and they are novel, which have deen searched through STN.Secondly, ten capillary gas chromatographic columns are prepared with static method, including seven CDs and three conventional stationary phase. Their chromatographic performances are as follows:(1) Some of the prepared CDs chiral stationary phases, have good film-forming ability and their column efficiency are more than 2000 plate/m, but others have poor film-forming ability. The polarity of novel CDs chiral stationary phases are tested and compared with the same kind CDs chiral stationary phases reported. The results show their polarity are moderate. The polarity of H1-CD is the strongest, SP1-CD the weakest among them.(2) The separation of new CDs chiral stationary phases for general compound is examined with Grab. The results display strong retention and favourable separation for general compounds, especially for aromatic isomers, such as xylene, cresol and chlorotolune, which are difficult to be separated on SE-54 and PEG-20M.(3) It is found that some chiral columns, including H-CD, P-CD and SP1-CD, possess excellent enantioseparation's ability. More than twenty general chiral compounds are separated, such as 2-chloropropionic acid methyl ester, allethyone acetate and propargyllone acetate etc.(4) We study enantioseparation of some chiral insecticide's intermediates on H1-CD. Eleven pyrethroid derivatives are separated. The results show the pyrethroid derivatives are well separated, including pyrethroic acid methyl esters (containing two chiral center and four chiral isomers), pyrethroic acid sec-butyl esters (containing three chiral center and eight chiral isomers).(5) The mechanism of enantioseparation is discussed from the view point of thermodynamics simply.