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The Synthesis Of Chiral Helical Poly[(S)-4,4,4-triphenyl-1-butene Oxide] And Its Application As HPLC Stationary Phase

Posted on:2010-10-18Degree:MasterType:Thesis
Country:ChinaCandidate:H R GuanFull Text:PDF
GTID:2231360302955873Subject:Organic Chemistry
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High-performance liquid chromatography (HPLC) as a convenient and fast method of separation and analysis of chemicals is widely used in medicine, food, chemical, pesticide residues, petroleum and other areas. Preparation of liquid chromatography stationary phase is key to the development of HPLC technologyThere are kinds of HPLC stationary phase in the market. A lot of chiral helical polymers are used for chiral HPLC stationary phase. Poly[(S)- 4,4,4-triphenyl-1-pentene oxide] (PTPBO) has helical structure, which has the potential of chiral resolution; Because of PTPBO’s structure contains a large number of benzene rings, the polymer has the potential capacity of reversed-phase chromatographic separation of aromatic hydrocarbon.PTPBO(initiated by potassium hydroxide) was coated on the silica gel to obtain polyether-type HPLC column. Its performance of chirally chromatographic separation was investigated in a variety of conditions. And it was found that the Oligomeric helical polyether (PTPBO) was not stable enough on the silica gel under the high-pressure conditions.Ether-bonded stationary phase is a kind of important stationary phase, and its production technology is also at hand. However, the report of production of polyether stationary phase in literatures is rare. In this paper, we have tried a variety of methods to make polyether-bonded stationary phase. Among the tried methods, the best one was that a coupling agent KH560 was coplymerization with PTPBO at the end of the anionic polymerization (initiated by potassium hydroxide) of (S)- 4,4,4-triphenyl-l-pentene oxide to obtain copolyether with KH560 as an end group. Then the coplymer was bonded to the surface of silica gel to get the polyether stationary phase PTPBO-KH560-Silical gel (PTKS). The structure of PTKS was characterized by infrared spectroscopy and elemental analysis. In reversed-phase high performance liquid chromatography (RP-HPLC) conditions, nine polycyclic aromatic hydrocarbons were separated by the stationary phase of PTKS. It was shown that in conditions of reversed-phase, there was goodπ-πreciprocity between the solute molecules and the aryl of PTKS, which is favorable for the next step to explore the capability of chiral separation. The stationary phase is stable enough in methanol, which also confirmed our initial idea: chiral stationary phase of helical polyether is more durable than the CSP of the helical polyester in the mobile phase of methanol.
Keywords/Search Tags:Helical polyether, PAHs, RP-HPLC, Chiral stationary phase
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