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Author: Subject: Acetic Acid Synth. Easy Home Version.
Have2Know
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[*] posted on 26-3-2014 at 12:26
Acetic Acid Synth. Easy Home Version.


Recently I ran into something really annoying....All over eBay was cheap glacial acetic acid, which was teasing me since no one on eBay will ship acetic acid to Hawaii. At first I wondered " conspiracy " . So I tried several home methods, I ended up using my original Ethyl Acetate + NaOH = Sodium Acetate + 80% H2SO4 = Acetic Acid, it always works, and it is predictable as heck. I wanted to see how much sodium acetate I could make this way in one batch, while managing the exothermic reaction as to not boil of my ethyl acetate, or need exotic cooling. 6 moles is the max at once with SS kitchen stuff and ice. I buy the 99% Ethyl Acetate at the hardware store, in 1 gal cans, where it is now sold as MEK Substitute, thus in the effort to make things more healthy, ethyl acetate went OTC.

Simply mix the ethyl acetate with lewis lye in a 1 mole NaOH + 1.1 mole Ethyl Acetate ratio, 1.1 since some is lost to evap. I just zero a kitchen scale to the Wally Mart SS beaker, mix x grams of lye, and x grams of ethyl acetate, and the easy part is done. Now you can take a small break, But do not do what I did, and leave even a "Tiny" 1-2 mole jar in the kitchen with your in laws and forget about it, when I remembered, they had already withdrawn from this kitchen and in the jar my sodium acetate ( mostly) was bone dry, so they must have been treated to my new super strength ethyl acetate / alcohol air freshener!

When you mix it, it just sits there....and does nothing for say about 10 min, then ever so slowly the temp rises and warm spots form, heat of course accelerates the reaction. Then the reaction speeds up big time, and requires cooling. I just use a big stainless steel beaker, with an ice filled bowl on top to act as a reflux condensor. With this plopped into an ice bath and me stirring like mad I can control about 6 moles with confidence. It is funny how the small lye prills morph into larger identical shaped sodium acetate prills, for some reason the starting lye physical state is carried forward and perfectly preserved in the first reaction, they are 3-5 times bigger though.

When the reaction subsides, I seal the Sodium Acetate prills in a jar with a jigger of ethyl acetate, for 24 hr, just to make sure there is no lye left.

For Distilation:

Since we can't get any non added surficant's, chromates, or other added crap added phosphoric acid here, I use 75-80% sulfuric acid, I am always sure to add the acid to the ice water to make 80%. The reason is at 98% sulfuric chars the Sodium Acetate, and gets way to hot. At 80% it still self distills in the beginning, and reacts fast.

Just for reference one 6 mole batch makes about 350 ml glacial acetic acid. I do not know why acetic acid is so hard to find here, all the organic farmers want it so they can spray weeds with 15-20% acetic acid solution, while keeping your organic farm certification. For me the best part is that you can replant / plant seed the next day : )

Last there is a small bonus in this acetic acid workup, the reaction by product is pure 200 proof ethanol, and its surprisingly easy to get it ethyl acetate free, just distil. I know there are so many ways of making acetic acid, for me this synth. is simply the easiest one for me, with no boiling down 20 liters down to one liter crap.

Enjoy : )

[Edited on 26-3-2014 by Have2Know]
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HgDinis25
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[*] posted on 26-3-2014 at 13:35


That is one of the best ways to get OTC Acetic Acid and pure ethanol. I didn't even know you could buy that quantity of Ethyl Acetate, in such a pure form. I've never found any in my usual stores.
Anyway, I don't know if you know but you can use Sodium Bisulfate instead of sulfuric acid to produce the acetic acid. I would use Sulfuric Acid anyway, but just in case...
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[*] posted on 26-3-2014 at 14:12


Nice work! I've not been able to find any good ethanol, so I'm certain that I will use this method.

Remember that even if x grams equals one mole of one substance, x grams of another substance may not be one mole. Go by number of moles, as you described first, and not only by mass.




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[*] posted on 26-3-2014 at 14:39


Nice work, were you going for pure glacial acetic acid?
A simple test to find the concentration of your acetic acid is to add some to sodium carbonate/sodium bicarbonate, If there is little to no reaction upon addition you have very pure glacial acetic acid, If it reacts and does the "volcano" reaction then you have a vinegar solution. Food for thought.




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Dr.Bob
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[*] posted on 27-3-2014 at 04:09


That is an excellent OTC prep of acetic acid. Thanks for posting it. Maybe you could write it up in a detailed experimental and take afew photos and post it on the experimental writeups section.
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[*] posted on 27-3-2014 at 07:55


For the sodium acetate would it not be possible to use sodium hydrogen carbonate and dilute acetic acid. NaHCo3+CH3COOH->C2H3O2Na+H2Co3.
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[*] posted on 27-3-2014 at 07:59


Quote: Originally posted by Spock  
For the sodium acetate would it not be possible to use sodium hydrogen carbonate and dilute acetic acid. NaHCo3+CH3COOH->C2H3O2Na+H2Co3.


NaHCO3+CH3COOH->C2H3O2Na+H2O + CO2.

That would work, but then you'd have to evaporate off a lot of water before going on to the next step.




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[*] posted on 27-3-2014 at 13:09


Thanks for the write up. It is interesting as a source of duty free ethanol, rather than using methylated spirits.
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[*] posted on 28-3-2014 at 20:34


Glad to see you ended up posting this, it definitely makes GAA and Absolute Ethanol more OTC.:)
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[*] posted on 10-4-2014 at 15:09


I followed along pretty well to your very humorous and useful preparation of GAA (and EtOH). I would probably try doing this with regular glassware – only because I have it (plus I would probably lose further use of my extremities from the administration of my wife's "home correction program")

The only part I couldn't see clearly, was how the ice filled bowl, on top of the pot would return all the condensing vapors to the "still pot". If the perimeter of the bowl were bigger than that of the pot (which it would have to be) would vapors not drip down, ultimately outside the pan/pot?

And, if the free 200 proof ethanol weren't enough, ethyl acetate being an MEK substitute!?! How lucky is that? It's like the opposite of Murphy's Law. I'm going to check out our substitute, is probably Japan stripper or something– Murphy's Law is still alive and well here.

Thank you for posting.
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[*] posted on 10-4-2014 at 15:09


I don't know how to delete a post :-)

[Edited on 10-4-2014 by CaptainPike]
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[*] posted on 10-4-2014 at 15:52


Quote: Originally posted by CaptainPike  
I don't know how to delete a post :-)

[Edited on 10-4-2014 by CaptainPike]


You must do it under 24 hours from the initial post while you still see an edit button upper right of your post. Go to edit, scroll down, you will see a box to check '! Delete this message !'. Check it, select 'edit post'.




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[*] posted on 12-4-2014 at 09:51


okay so the KLEEN STRIP MEK substitute is, indeed, 100% EtOAC. This news is, by itself is worth the trip to the Home Depot. I didn't do so well with the sodium hydroxide. The drain opener, alkaline version was hypochlorite-based potassium hydroxide secondary.

What I'm more interested in however is writing out a balanced equation and understanding how the anhydrous ethanol and the glacial acetic acid are separated. There may not be azeotropes here – i.e., I see how one could distill off the ethanol, possibly, but wouldn't that leave the glacial acetic acid contaminated with ethyl acetate?

So, can the ethanol really be gotten out by simple distillation? I'm still very happy to learn about this saponification (?), since it provides a very inexpensive and elegant solution to a couple of little problems I have. Will you please provide a little more info on the "acid workup" part of this preparation? Such as, how much "pretty strong" sulfuric acid vs ice is needed. I may use my liquid fire drain opener sulfuric acid for this.

Attachment: 1636 KS MEK Substitute.pdf (28kB)
This file has been downloaded 363 times

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[*] posted on 18-4-2014 at 06:37


OP mentions phosphoric acid. Could the second step distillation be accomplished with 85% phosphoric acid instead on using the sulfuric acid, or would it still need to be diluted down to 75-80%? Another thought, If we are introducing a diluted acid into the equation then how do we expect to get absolute alcohol out of it also. With ethanol's affinity for water I don't see how you could get away with not picking of water out of the equation.
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[*] posted on 18-4-2014 at 08:16



This is a nice piece of information, both for informing readers about the availability of cheap OTC ethyl acetate, and the production of near anhydrous ethanol & Sodium acetate/glacial acetic acid.

The procedure is understandable to me- And I can write out the equations. But OP could REALLY benefit from a little bit of an edit for clarity. Also, maybe include balanced equations? Perhaps a picture of your equipment setup? Brief mention of temperatures for the two products you're distilling off? The second distillation of the ethanol to separate from any remaining ethyl acetate?

[Edited on 18-4-2014 by Bert]




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[*] posted on 18-4-2014 at 08:23


Yeah, I figured out we were actually looking at two separate reactions here.

You're still going to be left with a mix of ethyl acetate and ethanol. That's going to be difficult to separate due to their close BP's. I don't know if vacuum would give you any separation in those BP's or not. I suspect it would and that's a wild guess, but ethyl acetate has a very low flash temperature. Someone correct me if I'm wrong, but doesn't that mean it begins emitting ethyl acetate vapor at that temperature at sufficient quantity that it can ignite? Ethanol's flash temperature is close to room temperature where ethyl acetate's, according to the pdf in this thread is sub-freezing. I would think there would be a way to take advantage of this with some careful vacuum distillation.

[Edited on 18-4-2014 by hyfalcon]

[Edited on 18-4-2014 by hyfalcon]
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[*] posted on 6-11-2014 at 18:46


Ketene production was discussed in acetic anhydride topic. I became aware that acetic acid can be made by reacting ketene with water. Could this be a viable route?
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[*] posted on 7-11-2014 at 03:22


Quote: Originally posted by Have2Know  
. I just use a big stainless steel beaker, with an ice filled bowl on top to act as a reflux condensor. With this plopped into an ice bath and me stirring like mad I can control about 6 moles with confidence

are you sure this is a good idea for a condenser?
because i remember trying out the same thing back in high school while i was doing the cannizzaro reaction with benzaldehyde and NaOH(i had put a china dish filled with ice cold water on the mouth of an erlenmeyer flask but though some of the vapors were condensing ,most of it was escaping (as i could smell the benzaldehyde)

also you say that you use a stainless stell vessel to run the reaction so i am assuming that it has only one mouth .so how can you stir the reaction mixture when the ice bowl is covering the mouth?
Quote: Originally posted by Steam  

A simple test to find the concentration of your acetic acid is to add some to sodium carbonate/sodium bicarbonate, If there is little to no reaction upon addition you have very pure glacial acetic acid, If it reacts and does the "volcano" reaction then you have a vinegar solution. Food for thought.

steam ,is it because as glacial acetic acid is so strong ,it will not ionize at all and hence not react?
Quote: Originally posted by Oxirane  
Ketene production was discussed in acetic anhydride topic. I became aware that acetic acid can be made by reacting ketene with water. Could this be a viable route?

yes that is a viable route ,but ketene is very toxic
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[*] posted on 7-11-2014 at 05:30


When I require ethyl acetate, I don't like to spend large amounts of funds on large quantity's of reagents so I buy smaller amounts in stores. I purchase non-acetone nail polish remover but its not very pure so fractional distillation is required. First to come over is the fragrance, once all of it is over replace the receiving flask and collect the rest which is all ethyl acetate. A brown stuff will leave a residue in the boiling flask but it is easy cleaned. You will yield 200ml of some what dry ethyl acetate.



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[*] posted on 22-11-2014 at 09:32
Ethyl acetate hydrolysis


Good day for all (i hope) and i have a question about ethyl acetate hydrolysis to obtain pure ethanol and acetic acid (glacial = desirable).
Both are relatively complicated to buy here.
I have the opportunity to build more or less complex apparatus.

Question A: Is there possible way to hydrolyse it using only water(steam) and catalyst, condense and then fraction distllation of mixture consists of unreacted EtAc, Acetic acid and ethanol?

Question B: In practice while using NaOH solution (or NH4OH to get acetamide) for EtAc hydrolysis, what byside products form? Because yield is not so high.
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[*] posted on 22-11-2014 at 10:12


The are no byproducts, other than the usual byproducts in the case of acetamide from ammonium acetate, which needs a certain following of protocol for good yields or else you'll lose all your ammonia, which you'll lose a lot of when starting with an aq. solution instead of dry ammonium acetate salt. The separate ethyl acetate layer should completely disappear. Reflux with NaOH shouldn't leave any unreacted ester whatsoever. If there's any left, the reflux time or concentration or excess of NaOH wasn't enough.



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[*] posted on 22-11-2014 at 10:57


Thank you.

Consequently in case of NaOH I'll get 95% spirit and NaOAc as a solution with yields not far from 100%.

And what about question A? Need Acetic acid and Ethanol as technical quality products in one step
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[*] posted on 22-11-2014 at 13:48


Quote: Originally posted by S.C. Wack  
The separate ethyl acetate layer should completely disappear. Reflux with NaOH shouldn't leave any unreacted ester whatsoever. If there's any left, the reflux time or concentration or excess of NaOH wasn't enough.


So you reflux the ester straight over pure NaOH? No water whatsoever? If so, is it practical to distil off the EtOH while hydrolysis in on-going?

[Edited on 22-11-2014 by blogfast25]




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[*] posted on 22-11-2014 at 14:08


I'd bet on that producing side products.
http://en.wikipedia.org/wiki/Claisen_condensation
(and by analogy with this)
http://www.orgsyn.org/demo.aspx?prep=cv1p0199

Also the boiling points of ethanol and its acetate are very similar so you won't be able to distil out the ethanol as it's formed
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[*] posted on 22-11-2014 at 14:13


The production of ethanol and glacial acetic acid from (cheap!) over the counter ethyl acetate and sodium hydroxide was discussed recently at some length...

I will be merging this thread with the above linked thread shortly.






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3. Mention anything you have learned from your target.
4. Only then are you permitted to say so much as a word of rebuttal or criticism.

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