Study Of Enantioseparation Using Polysaccharide Derivative Chiral Stationary Phase

Many enantiomers of chiral pharmaceuticals and pesticides showdifferent biological activities and toxicity, so the separation of enantiomersis very important. The enantioseparation of several typical chiralpharmaceuticals and pesticides was investigated on commercialpolysaccharide-derivative chiral stationary phases and self-preparedcellulose-derivative chiral stationary phases using high performance liquidchromatography.In first part, using 4,4'-methylenediphenyl diisocyanate as bondingspacer, cellulose benzoate(bonded-CTB) and cellulose 3,5-dimethylphenyl-carbamate(bonded-CDMPC) were bonded to aminopropylsilica gel at6-position, the preparation of bonded-CTB and its application ofenantioseparation have not seen literature report at present. Theself-prepared chiral stationary phases were characterized by FT-IR, and theenantioseparation of benzoin, trans-stilbene oxide and troger's base wasstudied onself-prepared columns, and on bonded-CDMPC get betterseparation.In the second part, the herbicide naproanilide was separated onChiralcel OD, OJ and self-prepared columns. The influence of mobile phase additives, concentration and temperature on the enantioseparationwas studied, and the two self-prepared columns can use withtetrahydrofuran(THF) as mobile phase modifier, especially naproanilidecan get baseline separation on bonded cellulose benzoate, it can be used forquantitative analysis of naproanilide enantiomers.In the third part, the chiral separation of2,3-diaryl-5-chloromethyl-1,3-oxazolidines and 2-(4'-nitro)-aryl,3-aryl-5-chloromethyl-1,3-oxazolidines was performed on chiralcel OD, chiralpakAD and Chiralpak AS. On Chiralcel OD, the four isomers of2,3-diaryl-5-chloromethyl-1,3-oxazolidines got baseline separation, and onChiralpak AD there was no separation of enantiomers, and on Chiralpak ASthe enantiomer were separated; due to the nitryl, the interaction between2-(4'-nitro)-aryl,3-aryl-5-chloromethyt-1,3-oxazolidines and CSPs can formstrongπ-πinteraction, and on Chiralpak AD the retention time was longest,and the elution sequence was also different from the other columns.In the final part, the enantioseparation of six triazole compounds andthree flavanone derivatives was studied on self-prepared columns, they allcan be separated completely on Bonded-CDMPC, while on Bonded-CTBthere is no obvious seperated peak at the experimental condition.