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axehandle
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NaHSO4
Sorry for cross-posting, but this merits attention:
"NaHSO4 mixed with alcohol gives a solution of H2SO4 in alcohol and Na2SO4 as a precipitate.
Boil, or better, distil off the alcohol and get the acid."
2NaHSO4 + C2H5OH --> H2SO4 + Na2SO4 + C2H5OH
LOOKS valid, and if it worked it would be kind of a H2SO4 holy grail (NaHSO4) can be
bought by the tons at pool supplier's.
Anyone ever tried this? Have I missed something (sometimes I can't even hit a barn with a BB-gun, sometimes I'm so right you could cry... =)
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BromicAcid
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Immediately I would wonder about the ability of the reaction to go foreword. If you dropped sodium hydrogensulfate into alcohol and it is not soluble
to begin with then the reaction would proceed incredibly slow. Even if it is soluble in alcohol then you have the problem of an insoluble solid
forming on the outside of the sodium hydrogensulfate and preventing further reaction.
You would probably have to dissolve the sodium hydrogensulfate in something like water then add and watch the precipitate but the water is going to be
able to dissolve appreciable amount of the sodium sulfate formed, and the alcohol is going to distill off before the water so this reaction would get
all mucked up.
In addition if you managed to get pure sulfuric acid and ethanol then if you try and boil it off you'll produce ethane and diethyl ether due to
the anhydrous acid concentration continuously rising and the temperature being elevated. But, all this is off the top of my head, I should look up
some solubility's but just giving my two cents for now.
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axehandle
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Here are my 3 cents:
http://www.jackspcs.com/chemdesc.htm
"SODIUM BISULFATE
Other names: Sodium acid sulfate; sodium hydrogen sulfate; sodium bisulphate; acid sulfate; sodium pyrosulfate; niter cake (impure).
Description: Sodium bisulfate is available as colorless, free-flowing crystals or as white, fused lumps; One part of the anhydrous bisulfate is
soluble in 2 parts water or 1 part boiling water, but alcohol decomposes it into sodium sulfate and sulfuric acid.
Precautions: Keep container tightly closed. Use with adequate ventilation. Do not inhale dust as contact with sodium bisulfate causes burns. Avoid
contact with eyes, skin, and clothing. Always wear safety glasses or goggles and rubber or similar impervious gloves. Do not swallow.
First Aid: For eye contact irrigate the eyes thoroughly with plenty of water, then contact a physician or an eye specialist. Thoroughly flush
contacted skin with plenty of water. Remove contaminated clothing at once and wash clothing before re-use. If swallowed, wash out mouth thoroughly
with plenty of water; give much water to drink, then give milk of magnesia. Call a physician at once.
Photographic Formulas: Iron Green/Blue Toner."
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The_Davster
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To make sure little/no diethyl ether is formed couldent you just mix the reactants in stoichiometric ammounts? or am I missing something really
obvious here?
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axehandle
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Where would the diethylether come from?
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axehandle
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Ah, sorry BromicAcid, I see your point. I'll just have to make damned sure my fume hood is working properly.
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chemoleo
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Well, if this works it's great!
For one thing, you *will* get diethylether, and temporarily ethylsulphate, but the good thing is alcohol is continuously shuffled out of the system by
distilling it off, as ether.
What I don't see, however, is, if only H2SO4 and Na2SO4 are present (the alcohol is now all boiled off as ether), what stops them from
recombining to NaHSO4? In other words, what we DON'T want is to destill off the C2H5OH, as it maintains the equilibrium being shifted to the
right side!
So, the question then poses - how are you going to purify the H2SO4 if you can't get rid of the Ethanol by destillation?
Conversely, you need to find a way to separate the H2SO4 from the Na2SO4 - and then you are all set 
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axehandle
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Na2SO4 is precipitated as a solid. I'll just pass
the ethanol/H2SO4 solution through a filtering
paper. Na2SO4 == history. =)
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chemoleo
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did you try it? If you can easily separate the two, then i guess all your problems are solved! Congratulations, you just found a way to make H2SO4
from NaHSO4, and ether as a byproduct!
Anyway, let us know if you get it to work well.
PS by the way, filtering paper is almost certainly not good, as you will turn it into carbon with the conc H2SO4! Borosilicate filter might be better,
or just let it settle.
[Edited on 29-1-2004 by chemoleo]
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axehandle
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chemeleo: Thanks for the tip. To think that I
was going to use a coffee filter *shudder*. What was I thinking?
I'll just let it settle, then pour off as much as
I can. Without the Na2SO4 there should be
no ether, right? In that case, a slow boil on
the stove's lowest setting might do just the
trick to remove the ethanol.
And in fact, I'm gonna try the method today!
I found NaHSO4 for appr. $20/7kg.
Then I'm gonna buy 4 liters of 95% ethanol.
Wish me luck, and I'll report my success (or failure) later.
[Edited on 2004-1-29 by axehandle]
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chemoleo
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forgot to say, maybe it might be wise to use an *excess* of ethanol - the reason being that it will be easier to filter off any precipitated Na2SO4 or
unreacted NaHSO4.
I would try to do this quantiatively, for instance take 10 g of NaHSO4, and calculate the theoretical amount of H2SO4 you'd get. Then calculate
how much Na2CO3 you'd need to neutralise the carbonate to get Na2SO4. If you manage to dissolve the carbonate with bubbles appearing to the very
end (CO2), then you know that the yield was very good. If there are no more bubbles after you added half of the theoretical amount necessary, then you
know the yield is at 50% and so on.
Also, for starters, i would grind the NaHSO4 as fine as possible, and also heat the solution up to 60 deg C or so (not over a Bunsen flame, but heat
plate!!!! ). This with continuous stirring. Do it for an hour or so. Actually, you might want to reflux it - that way you will keep the ether.
Good luck
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Ramiel
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I may be wrong too, but here's my 2 peneth worth (that's about 1/4 cents!  ).
If there is little water, and the H<sub>2</sub>SO<sub>4</sub> is more ionic than the NaHSO<sub>4</sub>, then
won't the sulphuric displace the less ionic salt from solution, and favour the forward reaction?
something sounds fishy about all this, but I just wonder if this helps the mechanism of the reaction (to do what one might not expect!).
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notagod
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axehandle! Where did you get the NaHSO4 from. (which company, city). You can PM me if you don't want to reply in thread.
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axehandle
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Any swimming pool chemical supplier should carry it.
17:15 I've just begun the first experiment, at room temp. The reaction is going slowly, so I'm heating the reaction vessel with a hair
drier.
17:25 Definitively getting an acid response. Litmus paper turned red almost instantly.
We'll see how it goes. Don't get too excited and blow all your money on NaHSO4 now, mates.... I'll fill you all in on the developments.
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axehandle
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17:40 Added an aqarium air pump as an ad-hoc stirring device. Temp. of alcohol approaching 50 degrees C.
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axehandle
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17:44 Stupidly tasted some of the liquid. Shock. Tish, tish, definitily acidic.
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axehandle
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17:48 Decided to go and wash my hands to avoid further acidic nailbiting incidents.
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axehandle
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This rection takes forever, albeit *something*
is definitely happening. I should have put the NaHSO4 prills (~2mm dia) in my ball mil first.
Trouble is, NaHSO4 is toxic as hell and can be absorbed through the skin as well as the lungs. Wouldn'r really want to inhale the stuff when
it's airfloat.....
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axehandle
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Have I finally found the holy grail?
I dissolved 1 part NaHSO4 in 1 part (by mass)
cold water. (Credits to BromicAcid for the suggestion.) Then I added a generous amount of ethanol. A precipitate immediately formed,
making the liquid milky until it sank to the bottom.
Litmus paper test indicated strong acidity. Turned bright red instantly.
I'm going to perform a larger test in a 2 liter
PET bottle.
Does anyone know if PET is resistant to BOTH ethanol AND sulfuric acid?
[Edited on 2004-1-29 by axehandle]
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BromicAcid
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Just a note, sodium bisulfate itself is strongly acidic in solution.
NaHSO4 ----> Na(+) + H3O(+) + SO4(2-)
So just testing for acid really isn't enough. You would probably need a titration to get the most accurate reading of how much H2SO4 you
produce.
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axehandle
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Yes, I know. From breathing the stuff firsthand. Very nasty stuff this.
Since I've forgotten all my college chemistry, could you please tell me of a kitchen-method way of detecting sulfuric acid?
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axehandle
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Whooo haaa!!!!!! Look at THAT precipitate!!!
It's INSTANT.
(Just added about 1 liter of ethanol to one liter of water+NaHSO4 solution.)
Now for the slow boil until (hopefully) white fumes appear.....
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axehandle
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If this really works, I'll have to build a condenser for the ethanol. I just spent 5 liters
for a measly 0.5kg of NaHSO4, and that makes
about $18 just for the ethanol.
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Polverone
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Don't get ahead of yourself
NaHSO4 itself is probably much less soluble in ethanol than it is in water, just like most other ionic solids. If you made a strong solution of NaCN
in water and then added ethanol, you would get a precipitate also, but it doesn't mean the NaCN, water, or alcohol have changed. The solubility
of the solvent system is just different.
Further, ethanol that contains even a little bit of water could possibly dissolve enough NaHSO4 to give an acid reaction on test paper, without any
significant formation of ether, sulfuric acid, or ethyl hydrogen sulfate.
Finally, sodium pyrosulfate is (contrary to that information above) distinct from sodium bisulfate, and I would expect it to react with alcohol more
than I would expect sodium bisulfate to. Sodium bisulfate can be transformed to sodium pyrosulfate by heating at 150-200 C for a couple of days (!) or
by heating somewhat higher than that for a few minutes. If it behaves like potassium bisulfate, it will melt, give off some vapor (water), then
solidify again, requiring much higher application of heat to melt once more. This higher-melting solid should be mostly sodium pyrosulfate, and I
think it could be worth trying to prepare and use some if your experiments with sodium bisulfate end in failure.
I don't want to rain on your parade, just warn that initial encouraging results can be misleading. Also, no reaction conditions were given for
the reaction of NaHSO4, so it may be that you'll get satisfactory results from it but only if you're willing to wait a long time or perform
the reaction with, say, hot ethanol vapor run over heated NaHSO4.
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guaguanco
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| Quote: | Originally posted by Polverone
perform the reaction with, say, hot ethanol vapor run over heated NaHSO4. |
Off the top of my head, running EtOH vapor over hot (presumably anhydrous) NaHSO4 sounds like a good way to produce either ethylene or diethylether.
Hot NaHSO4 is an excellent cracking catalyst.
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