Author Topic: Nitroethane (Read 2059 times)

poisoninthestain · « **on:** April 12, 2009, 08:17:34 AM »

Has anyone had success either sourcing or synthing nitroethane?

Sedit · « **Reply #1 on:** April 12, 2009, 04:05:04 PM »

Ill get back to you on that one

, I plan on chlorination followed with sodium nitrite. Its to useful of a chemical to not synthesis.

poisoninthestain · « **Reply #2 on:** April 12, 2009, 04:22:41 PM »

Awesome, I was thinking something with NaNO2 would be the way to go. Fuck silver nitrite and all the ethyl halide shit.

Vesp · « **Reply #3 on:** April 12, 2009, 05:55:30 PM »

Good luck with this! I think you'd be best off oxidizing ethylamine personally. I believe the NaNO2, and Silver nitrite methods both give amazingly low yeilds, but I could be wrong. I've just never heard anyone having success.

If you can acquire ethane, react that with nitric acid to get nitroethane

Sedit · « **Reply #4 on:** April 12, 2009, 09:08:43 PM »

Ethane and nitric you say? Ethane can be produces in a number of fasions given you treat it with the respect if deserves.

Tell me more tell me more.

@poison ethylhalides was the way I was going to go.

Vesp · « **Reply #5 on:** April 12, 2009, 09:32:43 PM »

Are you thinking ethane or ethylene?
ethylene is produced from ethanol and sulfuric acid.

Ethane can be produced by electrolysis of acetates, but that sounds like a pain. Possibly nitroacetate and acetone could produce nitroethane.

You basically just pass nitric acid and ethane vapors in a heated vessel or something like that and you get a mixture of nitroethane and nitromethane along with some other crap i am sure.

Douchermann · « **Reply #6 on:** April 12, 2009, 09:36:28 PM »

I just posted something similar to this in another thread:

The silver nitrite method is the best, if you can economically and reliably dry the ether (dry!). Otherwise, it simply will not work. The silver salt is re-usable (once converted back to silver nitrite), and the ether is reusable. The sodium nitrite method does not work in DMSO, as the ethyl halide will form a complex with it, but I've heard good things about DMF.

Gas phase nitration of propane would work if you could control temps. I could not, and had two explosions attempting this in my home-made 4ft reactor. The reaction tube was cheap soda glass, since I couldn't find any quartz tube, so it would bow in the center, and eventually crack on the edges, which would allow flames to lick at the propane/HNO3 combination. Also, the temp has to be kept moderately low, otherwise it just oxidizes everything. Gas phase nitration of propane would give about 26% nitroethane, the rest being nitromethane, 1 nitro propane, and 2-nitropropane, and the typicals like CO/CO2/H2O/N2/NO/NO2. Gas phase nitration of ethane gives 80% yeilds, according to a patent, but ethane is much harder to procure.

Vesp · « **Reply #7 on:** April 12, 2009, 09:41:47 PM »

Think it would be at all useful to attempt making ethane from acetates? It seems like a concentrated solution of sodium acetate, and a great power supply would be able to produce plenty of ethane. The tricky part would be getting that to react with the nitric acid as it is produced. Wonder what electrolysis of sodium nitrite, and acetate would do?

Douchermann · « **Reply #8 on:** April 12, 2009, 09:43:51 PM »

A typical lab scale or home scale electrolysis set up would be very slow. If one wants to be daring, you can start with large drums and use battery chargers which ahve the high amp car starter choice (50-100 amp)

Vesp · « **Reply #9 on:** April 12, 2009, 09:50:58 PM »

Quote

When sodium propionate and potassium nitrite were used as the two electrolytes, a small quantity of nitroethane was obtained

-- http://books.google.com/books?id=Pew4AAAAMAAJ&pg=PA11&lpg=PA11&dq=nitroethane+nitrite+acetate+electrolysis&source=bl&ots=kZTbHlnp7_&sig=REomNOJ-UlaUL4JuGkrQ1uIQVYc&hl=en&ei=dmHiSaHwJqSwtAOM5b2zCQ&sa=X&oi=book_result&ct=result&resnum=2

Now.. how small is small?
Also this gives me hope that there is some way similiar for producing better amounts of nitroethane

It seems nitroacetates are very unstable and hydrolyze into nitromethane. That is to bad for my nitroacetate:acetate idea, however i think this suggests that nitropropanoic acid is easily decarboxylated to nitroethane. I guess this is just the Alanine nitroethane synthesis all over again. I think if one were to be able to get nitrobutane, reacting that with NaOH might yield some nitropropanoic acid, though I could be wrong.

Actually, what is the alanine method? I know their are two ways one could go about it using alanine. The first being to oxidize the amine to a nitro and then decarboxylate it.
The second, which I want to say would be a cleaner reaction, but lower yielding, would be to make chloropropanoic acid from alanine via diazotization in hydrochloric acid. Then react chloropropanoic acid with a base to get the sodium salt, reacting that again with sodium nitrite to get nitroethane.

This synthesis, but in stead of using chloroacetic acid, use chloropropanoic acid. http://www.orgsyn.org/orgsyn/prep.asp?prep=cv1p0401

Propanoic acid could be prepared from N-propanol. The most OTC source of this I could find is it as some ether (ester?) in Expo cleaning solution. KMnO4 could oxidize that to propanoic acid, which could later then be chlorinated.

It all sounds like a huge hassle to me though so I'd go with a different method.

Vesp · « **Reply #10 on:** May 04, 2009, 11:37:01 PM »

Think it would be practical in any sort of way to make nitroethane from aspartic acid? I don't know how available aspartic acid is, but its decarboxylation looks like it would produce ethylamine. So I would think one could oxidize the amine group on aspartic acid, and then decarboxylate to produce Nitroethane.

Oxidation could likely be achieved with potassium permanganate or a persulfate.

timecube · « **Reply #11 on:** June 03, 2009, 06:28:46 PM »

You can buy aspartic acid by the kilo, but I still think ethyl bromide + NaNO is your best bet.
It seems relatively straight forward.

http://designer-drug.com/pte/12.162.180.114/dcd/chemistry/nitroalkane.html

Vesp · « **Reply #12 on:** June 08, 2009, 07:31:54 PM »

It may be, but I haven't heard of any success with it.

Does potassium permanganate oxidize ethanol directly to acetic acid, or is acetaldehyde an intermediate in the oxidation reaction between the two?

Also does Potassium permanganate oxidize NH3 in solution? I don't think it would but I guess ammonium permanganate in theory would form, and reduce the MnO4- into MnO2, producing N2 and H2O.

I was thinking if acetaldehyde forms in any decent quantity from that reaction, maybe ammonia could be added to the mixture to react with the acetaldehyde to form something similar to hexamine before were further oxidized into acetic acid... assuming the hexamine stuff wasn't oxidized into something else, other then maybe nitroethane itself!

With this acetaldehyde variant of hexamine, ethylamine could be formed with the typical methylamine synth, and then in the same pot, instead of purifying the ethylamine, potassium permanganate could be added again to yield nitroethane.

This reaction doesn't seem that favorable, though it might yield nitroethane and for a lot of us the chemicals are very OTC or can at least be made from common items.

This may be a stupid idea as I haven't looked up the mechanisms of the KMnO4 oxidation, but I figured I'd post it here anyways to maybe get a few more ideas going. What do you think of it?

eesakiwi · « **Reply #13 on:** August 10, 2009, 07:42:46 AM »

NitroEthane is OTC if you look really hard for it, really really hard...

MSDS is your friend.

Look into any sort of solvent in any sort of application & you will nail it down.

Vanadium · « **Reply #14 on:** August 10, 2009, 07:28:51 PM »

Quote from: Vesp on June 08, 2009, 07:31:54 PM

It may be, but I haven't heard of any success with it.

Does potassium permanganate oxidize ethanol directly to acetic acid, or is acetaldehyde an intermediate in the oxidation reaction between the two?

Also does Potassium permanganate oxidize NH3 in solution? I don't think it would but I guess ammonium permanganate in theory would form, and reduce the MnO4- into MnO2, producing N2 and H2O.

I was thinking if acetaldehyde forms in any decent quantity from that reaction, maybe ammonia could be added to the mixture to react with the acetaldehyde to form something similar to hexamine before were further oxidized into acetic acid... assuming the hexamine stuff wasn't oxidized into something else, other then maybe nitroethane itself!

With this acetaldehyde variant of hexamine, ethylamine could be formed with the typical methylamine synth, and then in the same pot, instead of purifying the ethylamine, potassium permanganate could be added again to yield nitroethane.

This reaction doesn't seem that favorable, though it might yield nitroethane and for a lot of us the chemicals are very OTC or can at least be made from common items.

This may be a stupid idea as I haven't looked up the mechanisms of the KMnO4 oxidation, but I figured I'd post it here anyways to maybe get a few more ideas going. What do you think of it?

If acetaldehyde is formed, it would be in very small quantities. A better bet would be to utilize the rather low boiling point of acetaldehyde in comparison to EtOH and AcOH and set up some sort of very slow or gas-phase oxidation; perhaps with Ca(OCl)2. Further, I seriously doubt that a dimethylene variation on HMTA would be formed as the ring strain is too high for that to occur. Unless you have refs...

Glutamate sounds fascinating though; does anyone have a ref on it?

Sedit · « **Reply #15 on:** August 10, 2009, 07:39:39 PM »

Quote

Also does Potassium permanganate oxidize NH3 in solution? I don't think it would but I guess ammonium permanganate in theory would form, and reduce the MnO4- into MnO2, producing N2 and H2O.

morethen likely create nitrates and nitrites. I once performed the oxidation of ammonia with H2O2. Im pretty sure I posted the nitrate paper detailing this over in the Nitrite threed at Science madness.

Formula409 · « **Reply #16 on:** September 19, 2009, 10:51:39 AM »

Been doing some research....
Is there a nitroethane synth that actualy porduces a usable yeild?
I have 500g of NaNO2 and could get by with 50ml of EtNO2

At the moment the only real option looks like AgNO2, silver is a bit of a problem but still a maby....
Is the Sodium Ethyl Sulfate method worth my time?

GAH!

Vesp · « **Reply #17 on:** September 19, 2009, 05:26:46 PM »

http://127.0.0.1/talk/index.php/topic,247.0.html

I'd try ball milling the nitrite and ethyl sulfate together. There is already a thread on this... don't forget to search!

Douchermann · « **Reply #18 on:** September 19, 2009, 07:04:30 PM »

AgNO2 is only worth it if you can make your ether absolutely anhydrous. If it has the slightest bit of water present, it just does not work. Not slow, not sluggish, just not at all hahaha. NaNO2 + EtNaSO4 has been shown to work, but the yeilds rely on how well you can mix the two together. I've tried the aqueous, and it's shite. The dry distillation is where it's at. Like vesp said, use a ball mill to mix them together. ...funny, I think I was the one that suggested that to vesp...

haha

Sedit · « **Reply #19 on:** September 19, 2009, 07:20:31 PM »

I merged this with one of the other Nitroethane synthesis.

Author Topic: Nitroethane (Read 2059 times)

poisoninthestain

Nitroethane

Sedit

Re: nitroethane

poisoninthestain

Re: nitroethane

Vesp

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Sedit

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Vesp

Re: nitroethane

Douchermann

Re: nitroethane

Vesp

Re: nitroethane

Douchermann

Re: nitroethane

Vesp

Re: nitroethane

Vesp

Re: nitroethane

timecube

Re: nitroethane

Vesp

Re: nitroethane

eesakiwi

Re: Nitroethane

Vanadium

Re: nitroethane

Sedit

Re: Nitroethane

Formula409

NitroEthane

Vesp

Re: NitroEthane

Douchermann

Re: NitroEthane

Sedit

Re: Nitroethane