Author Topic: Acetic Acid.  (Read 368 times)

Vesp

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Re: Acetic Acid.
« Reply #20 on: May 14, 2009, 09:45:11 PM »
I've never seen it, but it seems like they should have it. They sell it online, 14oz for 4 bucks. That would be great if I could find it for that price, and it were really 70%
I will look next time as well, seems like you may be more likely to find it in a health food store for some reason, with an inflated price.
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delic

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Re: Acetic Acid.
« Reply #21 on: May 21, 2009, 06:51:34 PM »
An ancient book, "Elements of the Theory and Practice of Chymistry" by Pierre Joseph may be useful:

Quote
To concentrate Vinegar by Frost.

Expose to the air, in frosty weather, the Vinegar you desire to concentrate. Icicles will form in it; but the while liquor will not freeze. Take out those icicles: and if you desire a further concentration of your Vinegar by this method, the liquor which did not freeze the first time must be exposted to a stronger frost. More icicles will form therein, which must likewise be separated, and kept to themselves. The liquor which doth not freeze this second time will be a very strong concentrated Vinegar.

Of course this will only concentrate the vinegar to a point, since pure acetic acid melts at 16.7oC. I was unable to determine the concentration of the lowest-melting mixture from googling.

timecube

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Re: Acetic Acid.
« Reply #22 on: June 04, 2009, 09:39:28 AM »
The most common brand of vinegar essence I could find online "Surig Essig Essenz" only claims to be 25%.  I'm pretty certain they don't sell anything like it in the stores around where I live in the eastern U.S.

Sodium acetate is OTC and cheap enough already that trying to pull it out of vinegar is a waste of time and money.  You will still have to heat it to make it anhydrous, but this will be considerably easier than trying to boil off several liters of water.

time2poop

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Re: Acetic Acid.
« Reply #23 on: June 04, 2009, 12:27:18 PM »
if you can buy sodium diacetate, that would be a great source for acetic acid.  no worry about left over carb/bicarb

Sedit

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Re: Acetic Acid.
« Reply #24 on: June 04, 2009, 03:08:48 PM »
As long as you give the dryed sodium acetate a splash of vineger and evaporate again bicarb should not be an issue, Trust me I had problems with the bicarb :o.

Im finding instead of sulfuric sodium sulfate trumps it hands down. Its well worth the extra cash to get some instead of using sulfuric which will contaminate your AcOH with SO2 which takes a long time to clear up. Using bisulfate you get an slightly milky distillate that clears up overnight or so into a crystal clear AcOH but with H2SO4 it always stays nasty looking for sometime. I think that the H2SO4 is hydrolysising some leftover organics into crap you dont want in your distillate.
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Vesp

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Re: Acetic Acid.
« Reply #25 on: June 08, 2009, 10:38:22 PM »
That is good to know Sodium Bisulfate works better for this! Bisulfate is a nice salt. You can always make it yourself, or if you  distill Nitric acid, or do ghetto nitrations it is likley a byproduct of the reaction.



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zzhuchila_clocker

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Re: Acetic Acid.
« Reply #26 on: June 09, 2009, 06:23:58 PM »
Yes, the essence is realy a popular item here;)
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Vesp

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Re: Acetic Acid.
« Reply #27 on: June 10, 2009, 06:28:06 AM »
Lucky you are able to get it. I've never seen it in my life, but I'll be sure to keep my eyes out for similiar products  :P
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timecube

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Re: Acetic Acid.
« Reply #28 on: June 10, 2009, 05:20:35 PM »
How do you perform this with sodium sulfate?  Just dry distill it with sodium acetate?  I can't see where the hydrogen would come from.

Vesp

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Re: Acetic Acid.
« Reply #29 on: June 10, 2009, 05:37:23 PM »
Sodium Bisulfate
Also known as Sodium Hydrogen Sulfate

It is NaHSO4, it acts like a mixture of  Na2SO4 and H2SO4

NaHSO4 + CH3COONa = Na2SO4 + CH3COOH

Sodium bisulfate really is pretty interesting, since it acts like a mixture of sodium sulfate and sulfuric acid, you are able to dissolve it in a solution of a chloride, nitrate or other and distill the acid. I have made decently concentrated nitric acid by mixing a boiling solution of a potassium nitrate with sodium bisulfate.

When an acid is added to sodium sulfate, it forms some sort of equilibrium like this:

 HX + Na2SO4 <==> NaHSO4 + NaX

The stronger the acid, the more NaHSO4 forms in solution - well, at least that is how I understand it.

I've always have been interested in finding a way to distill nitric acid from ammonium nitrate, a sulfate and a weaker acid such as hydrochloric acid considering bisulfate would sort of form, and might allow the nitric acid to leave, while leaving ammonium chloride.
An acid with a higher boiling point and a less soluble would probably be better suited for that reaction then hydrochloric acid though.  Phosphoric acid sounds like a candidate if it is at all possible.
 Sorry I'm kind of just thinking out loud. There are a few good threads at sciencemadness about bisulfate, you may find them interesting.





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Goldmember

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Re: Acetic Acid.
« Reply #30 on: June 14, 2009, 02:00:00 PM »
One could always choose to make ethyl acetate first from bisulfate,ethanol and the crude acetate and then make your acetic acid from there.

Sedit

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Re: Acetic Acid.
« Reply #31 on: June 14, 2009, 05:05:12 PM »
Do you have a reference for this process Goldmember?
 
The post directly under this one suggest that this will produce a totaly different product,

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

The results of EtOH + Sodium Bisulfate = Sodium Ethylsulfate which then can be used in Nitroethane synthesis.

There is no oxidising agent avalible to convert your alcohol to the acetic acid. To get an carboxylic acid one would need to first oxidise this with something like Ozone or KMnO4 and then Ethylate that, But.... if you just make AcOH and thats the product you want I don't see much need to convert it to ethylacetate just to cleave it again back to AcOH.

References brother, because without them were spinning our wheels here.




Speaking of this I will hunt down the reference I have posted over at SciMad for the synthesis of AcOH from EtOH and Fentons reagent or O3 with 80% yeilds IIRC from using O3(did I post that already over in my short experiment threed?). Using Fentons reagent(Fe(II) + H2O2) I did manage to produce some Formates and Acetates so oxidation could prove to be a useful means of formic acid from Methanol.
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Vesp

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Re: Acetic Acid.
« Reply #32 on: June 14, 2009, 09:10:46 PM »
Isn't he is saying is that you mix Sodium Acetate, and Sodium Bisulfate with alcohol to distill Ethyl Acetate. Not just alcohol and Bisulfate.

This seems totally possible to me since the formed sodium sulfate could suck up the extra water, and the bisulfate could work as a catalyst since it is acidic and what not. Also it could possibly work to dehydrate the mixture as well. I think refluxing that mixture for a while with an excess of sodium bisulfate would probably work the best. I don't though, I didn't look for references, etc. Just saying what I think would happen.

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Sedit

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Re: Acetic Acid.
« Reply #33 on: June 14, 2009, 11:17:19 PM »
My mistake. I see where he adds crude Acetate. But as I asked him a reference would be nice so we dont have to go around guessing.
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Goldmember

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Re: Acetic Acid.
« Reply #34 on: June 16, 2009, 10:39:32 PM »
No worries Sedit.Ill dig it up tonight.Im off to work right now.

Goldmember

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Re: Acetic Acid.
« Reply #35 on: June 17, 2009, 01:24:01 PM »
Aw shit,My first post here and Im already running around spreading misinformation. ::)
Although unless it can be shown otherwise,I think Im the one who first coined the idea of distilling bisulfate and acetate to form acetic acid in a SM thread a few years ago and that idea came from a formic acid patent I came across.(this method is not as easy as it sounds btw.)

I must say I havent tried what I stated in the above post,but I think it has a good chance of working.


Anyway,Replace the bisulfate for some sulfuric as described here:
http://chestofbooks.com/food/beverages/Alcohol-Properties/Manufacture-Of-Ethyl-Acetate-Acetic-Ether.html

Note:The author does infer that a replacement esterfication catalyst can be used ,and what better a replacement than the bisulfate yeah?
Reasoning=Same as Vesps.

Ok now the source of my confusion:

Kopp's method is as follows.3 A cooled mixture of 7 parts by weight of alcohol (88 per cent. strength) and 11 parts of strong sulphuric acid, is poured on to 8 parts of anhydrous sodium formate, and the whole carefully distilled from a water-bath. The yield of ester, however, is less than 80 per cent. of the theoretical quantity, and the product contains some formic acid. To remove this it is shaken with milk of lime, then dried with calcium chloride, and rectified.

By using sodium bisulphate instead of sulphuric acid, a better yield is obtained, and the ester produced is nearly free from acid.4 The bisulphate (240 parts) is well crushed, and mixed with 46 parts (weight) of alcohol and 68 parts of sodium formate. This mixture is warmed in a closed vessel, with frequent stirring, for about ten hours at a temperature of 80°; or, alternatively, it may be gently boiled in a vessel fitted with a reflux condenser. At the end of that time, the ethyl formate is distilled off.




http://chestofbooks.com/food/beverages/Alcohol-Properties/index.html  <-- Bloody good book.Check  out the whole thing.

http://books.google.com.au/books?id=3MjdGp1v1YIC&printsec=frontcover&source=gbs_summary_r&cad=0#PPA6,M1 Interesting read



Sorry guys Ill try to be a bit more accurate.

Sedit

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Re: Acetic Acid.
« Reply #36 on: June 17, 2009, 04:33:18 PM »
Its all good, thanks for the information Gold Ill have to have a look thru it later.

As far as using the bisulfate for AcOH synthesis I think its easyer then working with H2SO4. The product comes out cleaner and you dont end up with loads of SO2 contamination if you over shoot your mark and other organics more then likely formed from H2SO4 dehydrating various shit thats also in vineger. This may not be a problem with commercial Sodium acetate but using OTC H2SO4 and OTC Sodium acetate there is problems with foaming(not from excess bicarb either but from something in the H2SO4 I think). The product comes out milky white smelling of SO2 most of the time and takes a few days to clear where as Bisulfate takes only about an hour or so to clear up and produces a superior product.
There once were some bees and you took all there stuff!
You pissed off the wasp now enough is enough!!!