Low melting inorganic salts of alkyl-, fluoroalkyl-, alkyl ether-, and fluoroalkyl ether-substituted oxazolidine and morpholine

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 degreesC 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 degreesC and are thermally stable with long liquid ranges as determined by thermal gravimetric analyses. For compounds 12, 16, and 18, thermal stabilities of greater than or equal to400 degreesC were observed. All the new compounds were characterized by spectroscopic and elemental analyses. Their densities and viscosities were also determined.