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Author: Subject: Question on making CH3NO2?
kclo4
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[*] posted on 13-5-2005 at 21:04
Question on making CH3NO2?


Would this work for making CH3NO2?

If methyl chloride (CH3Cl) was to be added to potassium nitrite (KNO2) would it react and make CH3NO2 and KCl or would there be a different reaction?




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ChemPhile
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[*] posted on 14-5-2005 at 00:16


I donnt think so. i think you ll get this product, methyl nitrite ester, whose molecular formula is CH3ONO, not CH3NO2.
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[*] posted on 14-5-2005 at 00:32


There will be no reaction at all IIRC.

[Edited on 14-5-2005 by Borek]




Marvin
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[*] posted on 14-5-2005 at 06:40


Well, I dont see anything obvious to say it can't work.

Methyl chloride being a gas would introduce some problems, the reaction is going to be really slow even at high concentrations. This means doing the experiment under pressure. You'll need a solvent that dissolves both the nitrite and the methyl chloride, the classic DMSO should potentially work. You'll want to switch to sodium nitrite for solubility reasons I think. You will also need something to destroy nitrites as they are formed, but in such a way as your container doesnt explode.

If the plan was just to bubble the gas through something and say 'tada nitromethane' you'll be very dissapointed, but in principle it can be done I think.
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kclo4
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[*] posted on 14-5-2005 at 07:47


Would ammonium hydroxide work? The reaction would be CH3Cl + NH4OH = CH3NH2 +H2O + HCl since it makes HCl it would then react with the CH3NH2 and make CH3Cl and NH3Cl


Were did the other post go that says CH3Cl + NH4 compound would work in solution

[Edited on 14-5-2005 by kclo4]




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cyclonite4
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[*] posted on 14-5-2005 at 08:36


Quote:
Originally posted by kclo4
Would ammonium hydroxide work? The reaction would be CH3Cl + NH4OH = CH3NH2 +H2O + HCl since it makes HCl it would then react with the CH3NH2 and make CH3Cl and NH3Cl


CH3NH2 is methanamine, not nitromethane. And that reaction would be more correctly:
CH3Cl + NH3 ----> CH3NH2 + HCl
Generalised:
Haloalkane + Ammonia ----> Amine + Hydrogen Halide

EDIT: Spelling
-and-
If an acid were to react with an amine, it would form an amine salt, e.g.
CH3NH2 + HCl <---> CH3NH3+Cl-

[Edited on 14-5-2005 by cyclonite4]




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kclo4
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[*] posted on 14-5-2005 at 12:09


CH03NH2 can be oxidized by H2O2 to make CH3NO2

[Edited on 14-5-2005 by kclo4]




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kclo4
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[*] posted on 14-5-2005 at 21:28


Could this reaction work and if not why not?
CH4OH + NH4Cl = CH3NH2 + HCl + H2O




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12AX7
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[*] posted on 14-5-2005 at 22:07


I would suspect not as ammonium is a stable ion and would prefer the Cl, unless you can get the methylamine/methlammonium to precipitate, or something.

Tim
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sparkgap
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[*] posted on 18-5-2005 at 08:53


I see no reason for ammonium ion to readily cleave a nice and stable C-O bond.

That, and -OH is a poor leaving group.

sparky (~_~)




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[*] posted on 18-5-2005 at 11:47


I made CH3NO2 by dissolving about 20g NaNO2 (I'm sure KNO2 would work) in a mixture of 100ml methanol and 100ml water, and then adding 100ml 50% H2SO4 dropwise from a sep funnel. the gas that bubbles off is CH3NO2. The reaction is immediate being why I add the acid slowly.
The amounts mentioned are not accurately worked out, just a thumbsuck which worked fine in this case.




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[*] posted on 18-5-2005 at 13:08


froot, you realise you made methylnitrite CH3ONO, and not nitromethane CH3NO2?



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Blind Angel
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[*] posted on 18-5-2005 at 17:25


the Niromethane method on syntethikal use a two step method very similar:
MeOH + H2SO4 -> MeHSO4
MeHSO4 + NaNO2 -> MeNO2

(very big picture)

It might be possible to make it one pot?




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froot
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[*] posted on 18-5-2005 at 23:41


OOOPS!! :o

And here I was thinking that nitromethane was CH3ONO2. Sorry Chemoleo




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alchemie
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[*] posted on 21-5-2005 at 04:58


Quote:
Originally posted by Blind Angel
the Niromethane method on syntethikal use a two step method very similar:
MeOH + H2SO4 -> MeHSO4
MeHSO4 + NaNO2 -> MeNO2

(very big picture)

It might be possible to make it one pot?


Actually there are very important differences between the two methods.

The method you are refering to consists in the solventless reaction between NaSO4CH3 and NaNO2. Wich yields nitromethane. This is different from the method root used, in wich H2SO4 is added to an aqueous solution of NaNO2 and methanol. This yields methyl nitrite.


This reaction:
MeOH + H2SO4 -> MeHSO4 + H2O
needs anhydrous conditions and would never occur in an aqueous solution. Actually, forming the methyl sulphuric acid is accomplished in methanol solution, with the aid a drying agent, like Na2SO4, to remove the water formed in the esterification of the acid.
The second step, formation of nitromethane from NaMeSO4 and NaNO2, also has to be done with exclusion of water, for the same reasons: hydrolysis of the sulphuric ester.

The reaction between NaMeSO4 and NaNO2 needs relatively high temperatures, wich requires heating the intimately mixed solid reagents. These reasons preclude the use of a solvent, making the one pot impossible.
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[*] posted on 21-5-2005 at 11:28


Not exactly.

Search WD.
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The_Davster
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[*] posted on 21-5-2005 at 21:01


It should be noted that methylsulfuric acid can be used as a chemical weapon...

EDIT: changed 'is a chemical weapon' to 'can be used as a chemical weapon'

[Edited on 22-5-2005 by rogue chemist]




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[*] posted on 25-5-2005 at 04:27


What I don't get from the whole thread is:

nitrocompounds are derivatives of the nitric acid, yet you want to prepare nitromethane from nitrite, not nitrate.

How come?

Smarkotan oz gluthozmaz

[Edited on 25-5-2005 by Borek]




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[*] posted on 25-5-2005 at 14:45


Nitromethane is MeNO2
MeNO3 (the one prepared with nitrate) is Methyl Nitrate




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[*] posted on 26-5-2005 at 15:04


Quote:
Originally posted by Blind Angel
Nitromethane is MeNO2
MeNO3 (the one prepared with nitrate) is Methyl Nitrate


That's not what I am referring to. Methyl nitrate is an ester and that's something totally different.
Take nitrobenzene - to prepare it you use mixture of sulphuric and nitric acid. Why? Because you need N(V) from nitric acid. I would expect that to produce nitromethane you need N(V) as well, not N(III).




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[*] posted on 27-5-2005 at 16:33


How can you make NaSO4CH3 I goggled it and found three sites with no information on it, or how to make it?



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Blind Angel
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[*] posted on 28-5-2005 at 09:26


Look on synthetikal, there is an easy and detailled work-up posted there.



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tetrachloromethane
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[*] posted on 27-6-2005 at 14:39


It is made commercially by reacting nitric acid vapor and methane at 400C. If the two reactants were mixed and passed through a very hot borosilicate tube, the resulting vapor could be condensed by a double jacket condenser. The only problem would be reaction rate. I'm not so good with chem kinetics, so could someone with greater knowlege in this area speak up?
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[*] posted on 6-12-2005 at 10:54


I just ask how come sometimes nitromethane is MeNO2 and sometimes it is CH3NO2?:o
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[*] posted on 6-12-2005 at 13:44


They are the same thing, Me is an abbreviation for Methyl. Methyl is the CH3 group you see there. Would it be possible to produce nitromethane by bubbling methane through nitric acid with a catalyst present? If so, what catalyst would be a good one.



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