Nitroethane

[148, 149]-Strike couldn't find any decent nitroethane synths except for a couple of Chemical Abstract articles. One suggestion is to treat 1.5 moles of Na2C02 with 1 mole of sodium ethylsulfite and 0.0645 moles of K2C03 at 125-130°C. Another route would be to use silver nitrate and ethyl iodide [8 p119]. This type of reaction has been used to nitrate other paraffins and would probably work.

Luckily for all of you there were a lot of people who contributed some very nice protocols for this extremely important chemical. The first recipe below was sent to Strike unsolicited in the mail by someone named Don Antoine ( a very nice person) [150] (Note: Strike was not given a complete citation with the article and so can only give a partial reference for this article. Sorry):

"Initial Run. - Into each of seven stoppered bottles was placed a mixture of ethyl sulphate [EtO-SOz-OEt] (120 g.) and sodium nitrite [NaNOJ solution (120 g. in 160 c.c. of water.) The bottles were shaken mechanically for 20 hours, the pressure being released at intervals. The contents were then poured into a separating funnel, and the upper layer separated, dried over calcium chloride and distilled at 14mm., the distillate up to 60° being col-

lected (the residue, ca 230 g., consisted of ethyl sulphate and was used again). The distillate was fractionated at atmospheric pressure, and the fraction ofb.p. 114-116° collected. This was shaken with water, dried over calcium chloride, run through charcoal and redistilled ; b.p. 114-115.5°. Yield, 124 g. (31% or allowing for recovered ethyl sulphate, 43.5%).

Routine Run. - A second experiment was then carried out using the same quantities of ethyl sulphate as above. The recovered nitrite solution (lower layer) from the first run was concentrated by adding approximately 16 g. of sodium nitrite per 160 c.c. of solution . Yield, 185 g. (46%, or allowing for recovered ethyl sulphate, 65%)."

This next method was included with a submission by Ritter that appeared in the Theoretical section of this book.

"Ethyl bromide 32g, 26.0 ml (,3mol) or Ethyl iodide 46g, 24ml (.3mol) is poured into a solution of 250 ml Dimethylsulfoxide (DMSO) or N,N Dimethylformamide or N-methylpyrolidone (DMSO preferred), 36 grams sodium nitrite (that's NaN02 pyromaniacs, not sodium nitrate) and 52 grams phloroglucinol dihydrate. This stuff is expensive but it can be recycled. Stopper all this in a flask with a good magnetic stirring bar and stir it in a room temp, water bath for 2 hours or.until an emulsion forms. At this point dump all into 600ml ice water and extract w/ two portions of 200ml methylene chloride. The MeCI2 extracts are washed w/water three times then dried w/ anhydrous magnesium sulfate then evaporated off in a fractional distillation setup, collecting the fraction that boils at 113-116'C at atmospheric pressure as pure nitroethane. Expected yield about 20 grams. That's not a ton of product but this reaction can be scaled to any size you can dream of and yields will stay in the 80% range."

The only other thing Strike has to say is that some have hinted that all of those p-nitropropene reduction methods (or at least

some of them) and others like them (which did not include) can be used to reduce species such as nitroethene to nitroethane. That certainly sounds reasonable. Now where the hell can one find nitroethene?

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