Synthesis Of Alkaline Ionic Liquids And Application In Organic Reactions

Ionic liquids are salts that composed entirely of organic cations and inorganic /organic anions and are liquids at room temperature or approaching room temperature. Ionic liquids have many specific properties, such as negligible vapor pressure, wide electrochemically stable window, good electrical conductivity, excellent thermal stabilities, recyle and so on. Therefore, the more and more researchers have focused on the study of ionic liquids in recent years. Alkaline catalyze is very important in technochemisty, but the traditional basic catalyzes have some disadvantages. As the development of the synthesize of functional ionic liquids, we can append basic groups to the structure of ionic liquids through the design of the ionic liquids. By this way, the novel ionic liquids not only have the advantages of the ionic liquids but also have the function of alkaline catalyzes. We try to append some groups to DBU and synthesis a series of basic ionic liquids.We also researched the catalysis of theses ionic liquids.In this paper, three intermediates of ionic liquids:1-butyl-1,8-diazabicyclo (5,4,0) undec-7-ene bromide ([BDBU]Br), 1-hexyl-1,8-diazabicyclo (5,4,0) undec-7-ene bromide ([HDBU]Br) and 1-octyl-1,8-diazabicyclo (5,4,0) undec-7-ene bromide ([ODBU]Br) were prepared which are generated from 1,8-diazabicyclo (5,4,0) undec-7-ene (DBU) with butyl bromide, hexyl bromide and octyl bromide. Then we used these intermediates synthesize six ionic liquids through anions exchange with NaBF₄ and NH₄PF₆.The six ionic liquids are 1-butyl-1,8-diazabicyclo (5,4,0) undec-7-ene tetrafluoroborate ([BDBU]BF₄),1-butyl-1,8-diazabicyclo (5,4,0) undec-7-ene hexadfluorophosphate ([BDBU]PF₆),1-hexyl-1,8-diazabicyclo (5,4,0) undec-7-ene tetrafluoroborate ([HDBU]BF₄),1-hexyl-1,8-diazabicyclo (5,4,0) undec-7-ene hexadfluorophosphate ([HDBU]PF₆),1-octyl-1,8-diazabicyclo (5,4,0) undec-7-ene tetrafluoroborate ([ODBU]BF₄) and 1-octyl-1,8-diazabicyclo (5,4,0) undec-7-ene hexadfluorophosphate ([ODBU] PF₆).They were all characterized by means of IR spectral and 1HNMR.The thermal properties and conductivities of the ionic liquids were also investigated. Three phthalocyanines: CoPc(CONH2)4,CuPc(CONH2)4 and ZnPc(CONH2)4 were synthesized by solid state method. The products were characterized by element analysis, UV /Vis and IR spectral. The influence of reaction temperature, reaction time and the different catalysts were investigated. The result indicated that the best yield and energy economizing were obtained when the reaction temperature was 240℃and the reaction time was 4 hours and that the yield was not affected by species of ionic liquids.The ionic liquids were used in the synthesis of cinnamic acid, Knoevenagel reaction and ester exchange reaction. The ionic liquids showed excellent activity in these reactions and satisfactory yield was obtained over a small amount of catalyst.All the products were characterized by IR spectral.