Making NITRO for my CAR
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- เผยแพร่เมื่อ 30 ก.ค. 2024
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/ hexazine
In this video I show you how nitromethane is made in the lab from chloroacetic acid.
Fist I prepared 100 ml 40% NaOH solution. I also dissolved 59 grams of NaNO2 in 80 ml of distilled water. In 1 liter 3 necked round bottom flask I placed 100 grams of chloroacetic acid and mixed it with 150 grams of crushed ice. To this mixture I added about 70 ml of the NaOH solution until the pH became basic. The temperature should not exceed 20 degrees during this step to prevent chlorine replacement with hydroxyl group. After the solution was neutralized, I added the NaNO2 solution to the mixture. The flask was heated slowly on an oil bath. When the temperature reaches 60 degrees CO2 starts to come off. Care should be taken so the solution will not bubble over. The nitromethane distills alongside with some water and separates in the receiver. The distillation was continued until no more CO2 and nitromethane came off. The nitromethane layer was separated, and the aqueous layer was saturated with NaCl and distilled. This yielded a few more ml of nitromethane. The combined amounts were washed with saturated NaCl solution and dried with some anhydrous Na2SO4. The salt was filtered, and the liquid distilled. The fraction between 96 and 99 ℃ was collected.
Yield 25 grams, 31%.
Boiling point 96-99 °C
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Hi Hexazine,
The low yield is not your fault; it is mostly due to the ambivalent behaviour of the nitrite anion into the exchange reaction.
R-X + Na-O-N=O --> R-NO2 + R-O-N=O + NaX
As you see you have nitroalcane but also alkyle nitrite.
One of the main drawbacks of the nitrite ester is its volatility, and its hydrolysibility.
R-O-N=O + H2O R-O-H + HO-N=O
From this one sees that one of the side product is HO-CH2-CO2H that you tried to avoid during neutralisation of Cl-CH2-CO2H by NaOH.
There have been many trials to improve the yield of desired nitro-product:
-change the solvent to maximize the solubility of the nitrite into the reaction solvent and increase the substitution reaction
-change the nitrite cation (Na, K, Li, Ag,...); silver is the most efficient for the nitro vs nitrite ratio, but AgNO2 has limited solubility (it is a way of isolating nitrite vs nitrate because nitrite is almost insoluble). Silver salts also have their price.
-change the halide into R-X (I > Br > Cl for the substitution reaction but so does the price and availability is more Cl > Br > I)
So with a limited amount of money and of availability to chems, hard to make much better.
Also with those, you can hardly go to the 50%; the limit being in the 60%.
Kind regards,
PHZ
(PHILOU Zrealone from the Science Madness forum)
nice video! however, common misconception, anhydrous sodium sulfate only removes about 95-98% of the water (trust me, i checked with Karl Fischer Titration). Best practice is to use molecular sieves.
Well, from my professional experience there is no water peak in the NMR spectrum when using Na2SO4, so it should be mostly fine. For some special purposes I agree that additional drying steps would be needed.
Small amounts of water is no problem, for RC or drag fuel.
Justin, do you have this data on CaCl2 & MgSO4 ? what is their percentage?
Would calcium oxide work?
I can only agree. There is even a paper about the efficiency of molecular sieves. They are unbeatable.
Nice video again with extra 3rd level humour... :o)
Beware that in your description there must be a mistake regarding the mp... 133-135°C is about 33°C higher than the bp what is arround 101°C... and this is very unusual for a compound to display a melting point higher than its boiling point...
********************************
For the rest there are side reactions...
The desired pathway is:
Cl-CH2-CO2-Na + NaNO2 --> O2N-CH2-CO2Na + NaCl
O2N-CH2-CO2Na -heat/H2O-> O2N-CH3 + NaHCO3
2 NaHCO3 -heat-> Na2CO3 + H2CO3
H2CO3 -heat-> H2O + CO2(g)
1) an excess of NaOH base in your neutralization will turn the nitromethane or nitroacetic acid orange brown due to a aci-nitromethanate or a aci-nitro-acetate...like this
CH3-NO2 + NaOH CH2=N(O)-Na + H2O
The Na nitronates (from nitromethane or from nitroacetate) are salts...thus non distillable...they also decompose with heat and suffer hydrolysis into aldehydes derivatives very reactive towards nitroalkyles to form nitroaldols and nitroalcenes (in basic media what is your case).
To avoid this the use of weaker bases like NaHCO3 or Na2CO3 may be considered since chloracetic acid is more acid than acetic acid (vinegar)...and vinegar is a characteristic test acid to reveal carbonates or hydrogenocarbonate via carbonic acid evolution (CO2 bubbles)...so you will get less heat, CO2 bubbles and the desired sodium chloroacetate with much less basicity (more neutral media after neutralization)
2) The nitrite may substitute the activated chloride atom from chlor(o)acetic acid in a desired nitroacetic fashion (O2N-CH2-CO2H)... but also into a nitrite ester of hydroxyacetic acid/glycolic acid (O=N-O-CH2-CO2H)...the later is very hydrolitically sensitive towards water to form glycolic acid and nitrous acid...that turn into nitrite of sodium with the sodium carbonate present (one end product of O2N-CH2-CO2Na production)...thus most of the nitrite ester turns to nothing worthy...thus lost chloracetic acid...since the glycolate can't subsitute its hydroxy (alcool) with nitrite anion in basic or neutral media...while nitrous acid could... indeed the ease of formation of nitrous esters from alcohols and nitrous acid is very easy and rapid... as much as its reversal hydrolysis reaction.
It is possible that a very small part of the nitrite ester succeed to the nitroalkyle conversion...but usually this calls for higher temperatures arround 115-140°.
Those side reactions 1) and 2) lower your yield.
Also, in your procedure you multiply the number of aqueous distillations and decantations... so each time some of your yield is reduced by losses on the walls into the column, in beakers, balloons and also with the filtration (filter paper is really a sponge each pore and the thin air layer between filter and filter paper keep valuable nitromethane by capillary...what is lost by further evaporation.
It could be beneficial to add CaCl2 to your first distillate to saturate your watery layer, break the emulsion and kick nitromethane out of it... CaCl2 is very soluble into water and will make it very dense what will help decantation a lot more than NaCl does...then add your dessicant.
Transfer in a vial or recipient by pouring most of the upper layer and leave a little nitromethane with the remaining heavier partially hydrated dessicant...take the remaining nitromethane with a long needle syringe ... that way your yield should be optimized.
PHZ
(PHILOU Zrealone from the Science Madness forum)
Wow! That's such a great explanation! I corrected the boiling point mistake 🙂.
I think you will also get some chloroform due to decarboxylation of chloroacetate before it has a chance to react with nitrite, thus why not to do a reflux before going straight into distilllation ?
@@papanyanz
Nope,
I think
Following you..why, how and from what reaction?
Chloracetic, dichloracetic and trichloracetic acid don't form the way chloroform does form methylketons...or from methyl group next to a carbonol atom (ethanol, isopropanol, R-CHOH-CH3)
The first need Cl° (radicalar reaction) or Cl(-) source (strong and reactive halogenators)... the second needs a Cl(+) source (hypochlorite, haloamine, haloamide) with a base.
Those halogenators Cl(+) or Cl° or active Cl(-) are not present in the media.
Also acetic acid or acetate do not react with base and hypochlorite to acheive any halogenation of the CH3 part..
Chloracetic acid is not formed easily and cannot form dichloracetic acid or trichloracetic acid without activated strong halogenator.
If you start from acetone to get chloroform from bleach (basic NaOCl, NaOH, NaCl)...the resulting unafected part is acetic acid as Na acetate... you only get one HCCl3, not two, from CH3-CO-CH3 despite the molecular symetry.
This proof CH3-CO-OH is unreactive despite CH3-CO-R is.
PHZ
(PHILOU Zrealone from the Science Madness forum)
@@philouzlouis2042 Sorry, I was thinking of trichloroacetic acid while writing that and this stuff does form chloroform through decarboxylation - there was a video of one guy obtaining chloroform using that method! Thanks for pointing out.
@@papanyanz
It is indeed possible to make chloroform via trichloroacetate decarboxylation (thermolysis)... but it has little to do with the reaction from the video ;o)
I loved it, keep the good work up man
bromobenzene? nitromethane? don't you think that's getting a little bit sus?
jokes aside that was a good video, I hope you keep making content like this
he's gonna make some mmc 😂😂😂
Very nice! I like both the presentation and the actual lab skill of yours.
Thank you!
Good job! 👍
Много се радвам да видя колега от БГ в ютуб! 😊 Успех!
Nice work. I enjoyed this video and look forward to seeing what else is on your channel.
Thanks.
Thank you!🙂
Nice logo ;o)
PHZ
(PHILOU Zrealone from the Science Madness forum)
Link for my Patreon account:
www.patreon.com/Hexazine
Колега, всичко е страхотно и много ти се радвам! Имам само една забележка - 40 г NaOH във 100 мл вода не прави 40% разтвор. Продължавай в същия дух, с интерес ще следя синтезите ти! ;)
Благодаря! Малко не съм го догледал 😅
@@Hexazine0 in wikipedia they say that industrially it is produced by combining propane and nitric acid in the gas phase at 350to450°c
I would assume that reaction would be more efficient
Is it doable at a small scale or too dangerous?
@@FirstLast-tx3yj Bro you mixing 2 very dangereus thing at 300 celcius what you expect
@@emir4707 that is how wikipedia says the industry produces it
@@FirstLast-tx3yj
The reaction is not that complicated at a lab scale; except for the volume you have to deal with (1 mole of any gas at STP is roughly 22,41 liters and following the same "perfect" gas law, this applies also for HNO3 or any liquid that is gaseous at 400-450°C).
The main problem comes from scaling up for an industrial scale.
The proces from HNO3 is exothermic so you have to temper it a bit (tinier batch, water of dilution, temperature control, heat exchanger, ...).
Usually one would start from CH4 but the reaction in this case calls for 450°C instead of 400°C for higher alcanes.
Methane gives mostly CH3-NO2 and oxidation products.
Ethane gives CH3-NO2, CH3-CH2-NO2 and oxidation products (those goes up with each extra C connected).
You can manage the risk of "explosion" or runaway/burning by playing with an out of stoechiometric mix (more HNO3 but this would result in more oxidation products; or more alcane (more reductive atmosphere and exces alcane, especially gaseous or liquid ones are easily separable).
With higher MW alcanes, you end up with more and more side products linked to oxidation, cracking).
The purification calls for distillation to isolate a specific product in a temperature range; and maybe a specific derivative.
In industry they often use available alcanes like propane or butane but oxidation products also go up and for the cracking products (porpane will provide oxidation products of methane, ethane, propane; and butane will deal with oxidation products of methane, ethane, propane and butane).
Also
methane --> nitromethane
ethane --> (1-)nitroethane
propane --> 1-nitropropane + 2-nitropropane
butane --> 1-nitrobutane + 2-nitrobutane (+ 3-nitrobutane + 4-nitrobutane) (those last two are identical to the two first due to rotation of 180° (symetry).
etc.
For example one simply will need to pass vapour of diluted HNO3 into liquid hexane (or gaseous) to get nitrohexanes and lower nitro-products aside with hexanone, hexadione, hexanoic acid, hexandioic acid, ...
I have even read that concentrations as low as 13% HNO3 can do the trick when codistilled.
A good chemist would then work from methane, ethane, propane or butane (all gaseous) or from n-pentane an n-hexane (both low bp liquids)).
Of course one soon realises that for the desired CH3-NO2, calling for higher alcanes, also means implicitely an exponential need for HNO3.
Kind regards
PHZ
(PHILOU Zrealone)
Looks like about enough to mix up 1 tank of race fuel for an R/C car! Pretty sure it's not much more than nitromethane (a range of 5-40% is what I remember the hobby shops having), methanol or ethanol balance, and a couple percent of castor oil. Oil might be synthetic these days, probably still just as gross when it runs out of the pipe though.
Please attempt twistane!! I swear one day ill have a channel per platonic solid
Кофичката Верея
Yooooo pal 😎😎👍👍...just came from the discord server
Welcome to my channel! 😀
Следваща молекула - кубан. Продължавай е същия дух xD
Кубана го прави Explosions and fire. Аз мисля да опитам твистан.
You might have the chemology figured, but have you run the numbers to see if the combustion will happen with the desired characteristics? No pre-ignition? How will this impact the strength of materials in your engine? Will combustion pressures remain within design limits?
Hello! Is there a similar procedure with cloro-ethanoic acid? I am interested in making nitro ethane. I need it to weld 3D printed plastic, solvent welding is really cool.
Will u put this in your car or do you need to scale it up a bit to get more Nitromethane? Why did you get a low yield 30 percent compared to 42 percent? Neat video.
Well, the whole car thing was more of a joke than an actual plan. It's mainly used in special race cars and you definitely need a lot more than 20 ml. 30% yield when 42 is the literature one is fairly good.
Great video and like your style. Can you send the reference paper? It would be helpful.
It's from prepchem
www.prepchem.com/synthesis-of-nitromethane/
Very interesting. I read that you can make nitro methane by passing methane gas through a fine mist of nitric acid and it will bind an NO to the molecule and condense into a liquid. I don't know the method used, probably big stainless steel containers, perhaps under pressure. It's not cheap fuel.
Theoretically (and practically) its should work that way.
Although for conveniance and control, I would drive a mix of alcane and HNO3 in a reaction zone, and condense all reaction products for isolation and recirculation of the alcane to the first stage.
Won't that produce a lot of byproducts? I think that nitro propane/ethan/methan/and butane would all work in my project, however. "It's a SCIENCE experiment!!" I am concerned with a combustion product of nitric acid and the RC and Dragster people use an oil to combat it or Kerosene .
@@TheWadetube
The synthesis produces more side products as the number of C linked to other C increases (more nitro possibilities, more oxidation possibilities as ketons or carboxilic acids, more elimination of alcohols to alcenes or decarboxilation to CO2).
The product needs to be purified first by distillation to get only the desired nitro-alcane (preferably NM).
The chemistry into the motor is way to complex since benzine and oil are already an awfull mix. I personnaly have very little interest in that aspect.
Of course playing with NM can turn your motor into a space shuttle motor, but usually the mechanic doesn't follow (pressure, temperature, rotating speed and octane index of the burning/knocking burning or explosion) can easily ruin your motor.
You rarely see people driving with 100% NM istead of benzine + a few % NM.
PHZ
(PHILOU Zrealone from the Science madness forum)
@@philouzlouis2042 The motor in mind IS a rocket motor. A heavy lift design that can withstand super high pressures and very high temperatures and so Nitro Methane is suitable for that end and with less oxygen consumption. My concern is Residence burn time in the combustion chamber for a small 6 inch tall chamber for Stoichiometric results with minimal oxygen and safe burn by-products... no cyanide and no nitric acid . Wish me luck.
@@TheWadetube
Good luck then :o)
The fact you want to make a rocket should be OK.
It is a rocket not for space (so not in vaccuum) and hence you have acces to some air (oxygen) arround and flying assistance (supporting fluid).
Air is important because all the oxygen that is not embarqued means a lighter overal weight for the rocket and thus more overal thrust.
Just to give an example, you have benzine what is mostly considered as a mix of alcanes (CxH(2x+2 )), if you have one kg of it this has more power than an equivalent weight of TNT ,glycerine trinitrate or NM.
This is the reason for the power of FAE (fuel air explosives) because the biggest part of the weight does come from the oxidiser that is on site all arround and as a minor part from the fluel; you only need the right timing and geometry to disperse the fuel and to ignite it as a mist.
PHZ
If you substituted 3-chlropropionic acid for the chlroroacetic acid, this synthesis would work for nitroethane pretty identically, no?
You would need 2-chloropropionic acid.
The EWG group (electro-withdrawing group (aka -NO2)) must be viccinal to the carboxilic group for such CO2 elimination to be possible.
Very nice video. But I don't understand why did you add NaOH at the beginning...
You need it alkaline so the nitrite ion is better nucleophile.
Ok thanks 👍
why you didnt use hno3 h2so4 and methanol ?
it can't produce nitromethane, only methyl nitrate and a lot of oxidation products
Where did you get the Chloro-acetic acid? it is like almost impossible to obtain for amature chemist! If you have access to the chloro-acetic asid, Why haven't you bought the nithromethane rightaway...
CAA is a way more available for amateurs than nitromethane. It can be produced from very OTC reagents like ethylene glycol, HCl and nitric acid, however this process isn't health-friendly
@@dimaminiailo3723 where can I find that process?
Между другото, не е много трудно - да купите RC-model гориво, а ето как да го почистите от MeOH & рициново масло вече е по-интересно
Is it true you can make nitro out of methane and nitric acid? Found a patent for the process on Google.
Yes but only in industrial environment
@@Hexazine0 Btw you can try doing that, the process itself isn't very complicated. Propane would be the best choise. I can send you a small paper about that process if you are interested in it
A horse can actually provide up to 14.9 horsepower!
Wasn't it Nitrous oxide in "The fast and the furious"?
obviously not
Yes it was in the one where they press the button and go faster
2fast2furious
Откъде взехте хлороцетната киселина? това е почти невъзможно да се получи за опитен химик! Ако имате достъп до хлороцетна киселина, защо не сте купили нитрометан веднага...
Chloroacetic acids pricey.
I make it for my truck. We are not the same.
I was sure nitromethane burns in a way more violent way.
Or you can just purchase a can of nitro from V.P. fuels, and "tip the can" into some alcohol, dump it into your fuel tank, and burn your engine up. . . 🤷🏻
Crap