Ethyl nitrate

[Ethyl]

I know that ethyl nitrate can be made from ethyl bromide and silver nitrate. But how is that done? Is the silver nitrate dissolved in some solvent and then EtBr is poured in and EtONO2 forms as a layer of liquid?

And could AgNO3 be replaced by Pb(NO3)2?

[Bugger]

The driving-force of that reaction would be the high lattice energy and hence high insolubility of AgBr (which with the price of Ag now would be worth refining for it afterwards). PbCl2 similarly being insoluble, it may be usable as a substitute. It would have to be carried out in some solvent in which both C2H5Br and AgNO3 or Pb(NO3)2 are very soluble, and in which the C2H5Br is significantly ionized, but with which NO3- and Ag+ or Pb++ do not react or easily form sparingly soluble salts. I would think suitable solvents are likely to be polar aprotic ones, especially ethers, like diethyl ether, furan, tetrahydrofuran, oxane, dioxane; and possibly ketones like acetone. Pyridine or other amine solvents may crystallize out as nitrates.

[Ethyl]

Thank you for the info.

It would be very nice if acetone would work. It is cheap, easy to get and EtONO2 would be easily separated from the reaction mixture by first filtering out PbBr2 and then pouring the remaining solution in water. As acetone is miscible with water they would mix and EtONO2 would fall out from the solution.
I will test the solubility of Pb(NO3)2 in acetone to see if it could work.

How could EtONO2 be separated from diethyl ether? Pouring in water would not work as ether is not miscible with water so EtONO2 would not fall out of solution. Perhaps leaving ether to evaporate from the nitrate would work? But I believe ethyl nitrate is also very volatile so a lot of it would also evaporate.