Low Melting Inorganic Salts of Alkyl-,Fluoroalkyl-,Alkyl Ether-,and Fluoroalkyl Ether-Substituted Oxazolidine and Morpholine

摘要

N-Alkyl- and N-fluoroalkyl-substituted oxazolidinium- and morpholinium-based quaternary salts and ionic liquids have been synthesized and characterized.Reactions of N-methyloxazolidine(1)or N-methylmorpholine(2)with 3-fluoropropyl bromide or iodopropane in THF at 25 deg C gave the quaternary salts(3a,b,4a,b).These salts were metathesized with various metal salts to yield the corresponding ionic liquids(5a-h,6a-i).N-Alkoxyethyl- and N-(fluoroalkoxy)ethyl-substituted morpholines(8-11)were prepared and quaternized with methyl iodide(8a-11a).Their corresponding ionic liquids(12-18)were obtained by anion exchange and characterized.For both series of compounds,nitrate,hexafluorophosphate,perchlorate,triflate,and bis(trifluoromethanesulfonyl)amide were utilized.Most of the final products are liquids at 25 deg C and are thermally stable with long liquid ranges as determined by thermal gravimetric analyses.For compounds 12,16,and 18,thermal stabilities of >=400 deg C were observed.All the new compounds were characterized by spectroscopic and elemental analyses.Their densities and viscosities were also determined.