Dimethylammonium nitrate

Test Yourself What is the pH of 0.010 M dimethylammonium nitrate (Answer 6.39)... 

Pure salts, including ILs, are not generally expected to be good conductors at moderate temperatures because of electrostatic interactions between their ions, which causes a decrease in mobility. Usually the maximiun ionic conductivity is obtained for electrolyte concentrations around 1 M. Angell et al. proved this is not always trae, showing that the neat PlLs of BAN, dimethylammonium nitrate, and ethylammonimn formate have good conductivities, which are less than those for lithimn salts in aqueous solutions but higher than those for nonaqueous lithium salts. 

Vitze, H., Lerner, H.-W. and Bolte, M., Dimethylammonium nitrate, Acta Crystallogr. E63... 

A slight excess of a 10% sodium hydroxide solution was added to a solution of 23 grams of silver nitrate in 300 cc of water. The precipitated silver oxide was washed free of silver ion with distilled water. To a suspension of the silver oxide in 200 cc of water, a solution of 25 grams of (3-hydroxyphenyl)ethyl dimethylammonium iodide in 300 cc of water was added. The precipitate of silver iodide was removed by filtration and the filtrate concentrated to a volume of about 100 cc In vacuo. The remainder of the water was removed by lyophilization. (3-hydroxyphenyl)ethyl dimethylammonium hydroxide was obtained as a hygroscopic, amorphous solid,... 

The reaction is complete when the clear supernatant solution in the reaction vessel no longer contains chlorine as detected by the addition of dilute nitric acid and silver nitrate solution to ca. 1-ml. of the clear solution withdrawn from the reaction flask. After the reaction is complete, the ice bath is removed, and stirring is continued for 2 hours at room temperature. After standing overnight, the dimethylammonium chloride is filtered and washed with n-hexane, with careful exclusion of the moisture of the atmosphere. The combined filtrates are distilled at atmospheric pressure to remove the solvent. The tris(dimethylamino)arsine distills at 36°/2 mm. (55 to 57°/10 mm.). The yield is 402 g. (78%). 

Similar to the imidazolium ILs, very low solubility of the ammonium ILs was observed in alkanes. Eor example, the solubility of butyl(2-hydroxyethyl) dimethylammonium bromide, [(Ci)2C4HOC2N]Br, exhibited a simple eutectic system with immiscibility in the liquid phase in the IL mole fraction range from XjL = 0.02 to 0.70 [53] the other ammonium salt, (benzyl)dimethyl-alkylammonium nitrate, [Be(Ci)2C N] [NOJ showed very small solubility in the liquid phase in hexadecane and it was slightly better in hexane (immiscibility from XjL = 10 to 0.90) [99] for the ammonium salt with an alkane substituent only, didecyldimethylammonium nitrate, [(Cio)2(Q)2N][N03], the solubility in the liquid phase was better in hexane (immiscibility from XjL = 10 to 0.50) than in hexadecane, where the immiscibility was observed in the whole IL mole frachon [100]. In all systems with imidazolium and ammonium salts, an increase in the alkyl chain length of the alkane (solvent) resulted in a decrease of solubility. 

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