The Hive > Methods Discourse

question about Nitroethane-synths

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Rhodium:
It doesn't work like that. Simple nitroalkanes are O-alkylated by alkyl halides, not C-alkylated. Besides, methyl chloride is a gas, and very hard to work with.

xxxxx:
have not performed reations, but had a document stating sodium nitromethane could be reacted with alkyl halides.

n00dle:
The bottom of that OrgSyn page says:

(..blahblah) 1-Nitroöctane has been prepared from (blahblah), from octane by boiling with nitric acid (more blah.)

if we can boil octane and nitric acid to nitroctane, then surely we could make nitroethane (if only the boiling point was in our favour) from ethane and nitric acid. Obviously its not possible because ethane boils too low. Perhaps ethane could be contained with nitric acid somehow? perhaps even ethane bubbled through nitric acid might form nitroethane?

sorry if SWIM offends anyone with his/her stupidity, he/she is just trying to help.

gsus:
alkane + HNO3 is how the lower aliphatic nitroalkanes are made in industry. this is not suited for most people but if you like to build things...and it doesn't seem that there are simpler alternatives using these alkanes.

you get a mixture of nitroalkanes with ethane and the ratio of products is highly dependent on conditions. high temp vapor-phase is generally used, probably multi-pass as well, i don't remember. see Patent US1967667 for why a more convenient method isn't around, AFAIK. you could probably find more with a "referenced by" search of the patent databases, this is the classic patent on this.

ten years ago i read a great Ind. Eng. Chem. article full of yields of various nitroalkanes under various conditions from methane to butane, in neat tables. a definitive article with much text as well. and came away thinking...silver nitrite and ethyl iodide. but i dont remember which article and of course you ask on a day on which all libraries are closed in the usa!

the inventor of vapor phase nitration, Hass, has a lot of Ind. Eng. Chem. articles, and some in JOC and JACS. his name got a lot of hits in TFSE, btw. so i don't know which of the following is best for the industrious, able bee, if any. all are by Hass, industrial methods not very well suited for most but you get the idea, and in Ind. Eng. Chem:
nitration of ethane: 32, 427 (1940)
various: 41, 2266 (1949), 33, 1138 (1941), 38, 251 (1946)
review: 39, 817 (1947)

n00dle:
I dont think it would be hard to build. I think it would look quite like methanol oxidation setup, using copper coated 300C tubing.  Only in this case we'd use pyrex glass and for reaction, i dont know. maybe a small tube of just barely gold plated piping. Flask of nitric acid --> glass tubing --> nitric acid resistant tubing which you heat with propane torch --> condensor at 45 degree angle --> dual head adaptor to pipe unreacted ethene gas away from propane torch (ugh!) and to collect nitric acid out other adaptor head. Any ideas? If it works, then all ppl need to do is chuck thier heads together to make the apparatus a bit more workable and we can turn the dream into reality.

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