Preparation Of Cellulose-(4-Chlorophenylcarbamate) Chiral Stationary Phases And Enantioseparation

With the development of life sciences and organic stereochemistry, chiral recognitionexhibits the important practical significance. In the separation technology of optical isomers,chiral chromatographic separation techniques growing fastest and widely used, which, HPLCchiral stationary phases (CSPs) method is much con cerned because of its fast speed and highefficiency, the key to this technology is the design and preparation of chiral stationary phase.Currently, the polysaccharide derivatives CSPs are widely used in chiral separation, amongthem, the microcrystalline cellulose is the most readily available natural polymer optics, andeasily modified, as chiral stationary phase showed the good chiral recognition ability andthere are a lot chiral columns has been commercialized. Preparation of cellulose derivativesCSPs has two mainly methods: the coating method and bonding method. A chiral columnprepared by coating method has strong chiral recognition ability, but a narrow range ofmobile phase to select; bonded chiral stationary phase, the choice of mobile phase are widerand variety of solvents can be used as polar additives, such as methylene chloride, chloroformand THF that is more chiral compounds can be separated hopefully, but the separation abilityis relatively weak. The two methods for preparing chiral column play a complementary role inthe separation of specific compound.This thesis consists of six parts: the first discusses the importance of chiral and chiralseparation, describes the methods and types of chiral stationary phase HPLC, and finallyelaborates the research progress of cellulose chiral stationary phase; Chapter II synthesizedCellulose-tris(4-Chlorophenylcarbamate) derivatives using coating method, the compoundswere characterized by1H-NMR and IR then coated on aminopropyl silica and zeolite SBA-15subsequently, made of chiral stationary phase to evaluate the chiral recognition abilitythrough HPLC method by use of12kinds of chiral compounds; Third, IV and V chaptersusing hexamethylene diisocyanate,4,4’-diphenylmethane diisocyanate and3-(triethoxysilyl)-propyl isocyanate as the bonding agent, three novel bonded cellulose-(4-chlorophenycarbamate) CSPs were prepared first by using regional selective and non-regional selectivemethods repectively. In the conventional and unconventional mobile phase, evaluated thechiral resolution ability of three chiral column, then coated type, bonded type and differentbonding reagents of the chiral column which separation abilities were compared; In the lastchapter, arginine and diclofop were directly resolved by high performance liquidchromatography on the Chiralcel OD-H, Chiralcel OJ-H and Chiralcel AD-H chiral column,the influence of the volume of isopropanol, flow rate and temperature on the separation ofarginine and diclofop were investigated. The chiral recognition mechanisms of the three chiralcolumns were studied by stoichiometric displacement model for retention and thermodynamictheory. Study the chiral recognition mechanism for the development of new chiral stationaryphase, separation different types of compounds and pharmacokinetic study and so has a very important significance.