Synthetic Camphor Derived Chiral Ionic Liquids And Its Application

Ionic liquid has aroused the attention of scientists, because of its low vapor pressure, excellent chemical stability and strong solubility. With the progressive development of green chemistry, ionic liquid gradually replaced the traditional organic solvent and has been widely used in separation, electrochemistry, chemical reaction. Ionic liquid has become a research hotspot in green chemistry research field in recent years.Chiral ionic liquids can be used not only as reaction solvent, but also as chiral catalyst. As a chiral catalyst, it can induce the asymmetric or unasymmetric selectivty. Ionic liquids as mild condition reaction solvent can get recycling. Therefore, the synthesis of chiral ionic liquids can make the recycling of the expensive chiral catalyst. Even that, there are several limitation to restrict the development of chiral ionic liquids, for example, expensive prices, difficulty in synthesis and so on. That is the reason why the chiral catalyst’s research is still in infancy. Because of natural chiral compounds have natural chiral centre. The best way to resolve the difficulty of synthesis chiral ionic liquid is that using natural chiral compound as the starting material to synthesize chiral ionic liquids by refined modification. In this thesis, we will report the synthesis of new chiral ionic liquids based on the natural chiral (D)-camphor.Thesis mainly includes the following three parts:In the first part, the definition and classification of chrial ionic liquids were summarized. The new developments and applications, two typical synthesis methods were included in this part. Based on the above knowledge, the research thought of this thesis was drawn and analyzed at the end of chapter.In the second part, with natural chiral source D-camphor as starting material, two kinds of chiral ionic liquids were synthesized via sulfonylation, cyclization, halogen substitution, reduction of C-N double bond and than via N-methyl imidazole alkylation. the structure of chiral ionic liquids was analyzed by FT-IR,1H/13C-NMR and confirmed with expected structure. The optical rotation data of chiral ionic liquids was detected by polarimetry.In the third part, the catalytic activity of chiral ionic liquids was investigated by using it in Diels-Alder reaction. The results show that the ionic liquid has good catalytic activity and diastereoisomer selectivity. It was also verified that the catalyst can be recovered and reused5times remained stable activity. All the investigation proves the synthesis chiral ionic liquids have good activity, simple operation and friendly to environment. The synthesis chiral ionic liquids are consistent with the requirements of green chemistry.