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Acetic Acid (Ethyl Acetate) from Ethanol

05/25/2017 10:18 AM

Which Products can we Extract from Ethyl alcohol (ETHANOL) through distillation and What should be detailed and complete process to extract them?

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i want to extract Acetic acid,Butyle acetate and any product which can be Extracted from Ethanol through Distillation and what will be complete Process to Extract any product From Ethanol.

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#1

Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/25/2017 10:30 AM

Distillation of ethanol will produce ethanol. Think brandy, whisky, vodka etc.

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#2
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/25/2017 10:50 AM

Dear Sir

i know that but actually i was asking what products further can be distilled from Ethanol and how?

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#6
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/25/2017 12:00 PM

There is no point in repeating a question that has already been answered.

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#19
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/26/2017 12:23 PM

By distillation, basically any compound with a different boiling point; so it all depends on your feedstock.

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#22
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/26/2017 12:45 PM

basically any compound with a different boiling point;

the basic concept of a Wiped Film Evaporator on how deep of a cut you want to make.

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#3

Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/25/2017 11:16 AM

Distillation can only isolate chemicals that are already in a mix of fluids. It cannot create new chemicals. If you only have ethanol then you can only get ethanol from distillation.

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#4

Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/25/2017 11:41 AM

JohnDG and redfred are both right.

If you are starting ONLY with ethanol, you will distill ONLY ethanol.

If however, you have a mixture of ethanol with other side products of a reaction, distillation can help separate the components of the mixture.

If you do have such a mixture, the components with the lower boiling points will come off first. Some components together form what are called azeotropes which are harder to separate by distillation. At that point you would start looking into how many stages your distillation column would need or into a packed column. Distillation at reduced pressure is often done as well.

I see from your previous thread that you are wanting to design a fermenter. I am assuming that this query is related.

As for wanting the complete process, it cannot be made available here. It takes years to understand the math and physics involved.

Hire a chemical engineer.

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#7
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/25/2017 12:02 PM

<...Hire a chemical engineer...>

GA for that.

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#5

Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/25/2017 11:57 AM

There are problems with this post:

  • Distillation is a physical process, not a chemical one. So whatever was in the <...Ethyl Alcohol...> before it was distilled will be in the condensed vapours, albeit at different concentrations from the original mix.
  • Acetic acid can be extracted from wine vinegar by distillation.
  • Butyl acetate is a compound achieved by chemical reactions away from the original feedstock.

Awaiting clarification on the intended process.

<...can we Extract...> this thread gives little confidence in the ability of the <...we...> to do anything in particular.

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#8

Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/25/2017 12:44 PM

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#9

Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/25/2017 1:02 PM

The only thing you can do is to bring it to 200 proof (pure Ethyl alcohol) if its not already.

If you want to distill to get acetic acid, you have to have the correct feed stock. and Ethanol is NOT the correct feed stock.

We product liquid smoke and acetic acid (hydrogen acetate) is one of the products we distill. We use it as a browning agent.

Back in my day as a freshmen in high school biology class, we used wooden tongue depressors and applied a Pyrolysis process to distilled methanol, and one of the by products was hydrogen acetate.

And when you cleaned up after your experiment, if your not careful, you stain you skin, cloths what ever cam in contact with the hydrogen acetate.

You may be a little confused here also... Now are you talking ethanol or methanol? not that it would make any difference.

Methanol is poisonous, and it is one of the chemicals that can be used to poison denatured alcohol.

Isopropyl alcohol is a slightly bigger molecule than ethanol

  • Methanol is CH4O
  • Ethanol is C2H6O
  • Isopropyl alcohol is C3H8O
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#10
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/25/2017 3:10 PM

I have never heard of anyone in 60 years of studying/working in chemistry call acetic acid - "hydrogen acetate."

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#11
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/25/2017 3:20 PM

When started working here, the plant engineer kept referring to HA. (say the letters H A). this confuse me quite a bit, because it sounded like he should be referring to Acetic Acid in the context of his conversation.

I questioned him about that, and his response was 'Same Thing'.

I had to look it up. Wasn't in my Perry's handbook, then I went to Google, and damn,... there it was, both were always tied or mentioned together.

I bet you look it up also

Chemistry isn't my strong suit. Maybe you can tell me this, is it incorrect?

Acetic acid
Molecular Formula: C2H4O2
Average mass: 60.052 Da
Monoisotopic mass: 60.021130 Da
ChemSpider: ID171

Hydrogen acetate (1:1)
Molecular Formula: C4H8O4
Average mass: 120.104 Da
Monoisotopic mass: 120.042259 Da
ChemSpider ID: 26667348

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#12
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/25/2017 4:43 PM

Chemspider shows 2 acetic acid molecules for the structure, sort of as if it were a dimer. I have never heard of this before for acetic acid. I'd say that Chemspider entry is bunk!

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#26
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/29/2017 10:48 PM

Can't think of any citations right now, but it is correct for glacial (almost pure) and non-polar solutions of acetic acid or almost any shorter chain simple organic acid. There is a strong hydrogen bonding between the OH on one molecule with the O= on another, that is reflected between the OH on the second and the O= on the first. So really, it is a hydrogen bonded dimer. This is known to contribute to the high boiling points of these acids as it effectively doubles their molecular weight.

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#27
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/29/2017 11:58 PM

OK Thanks! I can buy that, maybe. The size of the molecules - the distance from -OH to =O is small / short enough to get more interactions between all molecules. After that, I wonder what makes them pair up? I'm not saying that I don't believe it, I just want to find out why that is so. Do you know?

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#28
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/30/2017 6:40 AM

Yes- it's the functional groups being identical in size and structure, and being available on an easily accessible primary carbon that contribute to this effect. So they would tend to bond in a mirror image pattern, effectively structured ----<>----.

This is found in the gas phase or in non-polar solutions, where the acids exist in a largely non ionized state that allows for this bonding to take place. In water etc. the attraction of the polar water molecule tends to interfere with this, as well as ionization.

It's mostly why multiprotic Acids such as oxalic and citric acids are crystalline instead of liquid. With simple monoprotic acids, as the chain length get bigger this still happens but London forces between the hydrocarbon backbones have a more prominent role in physical characteristics.

This really is not a true dimer though, it's more of a local attraction that is limited to two molecules per complex.

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#29
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/30/2017 7:08 AM

My question is,... is calling it 'Hydrogen Acetate' correct or is that just something that was put together by a layman, or a chemist trying to put it in layman's terms..

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#30
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/30/2017 8:22 AM

I don't know!

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#31
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/30/2017 8:36 AM

It makes as much sense as calling nitric acid 'hydrogen nitrate' or sulfuric acid as 'hydrogen sulfate' - that is to say, no sense.

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#32
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/30/2017 9:05 AM

That's the problem, 'you don't know, what you don't know'.

When I run into our chemist here, I'll ask him the reasoning and why its called HA. could all have started out as an uninformed bad habit years ago.

If there is a sound reason for it,... I'll pass it along.

thanks

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#33
In reply to #31

Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/30/2017 5:00 PM

It makes sense to Ester

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#34
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

06/05/2017 4:50 AM

Just to add - HCl as a gas is called hydrogen chloride. It's readily soluble in water to give hydrochloric acid. But the strength of hydrochloric acid is limited by the solubility, so maximum is about 35% w/w, unlike nitric, sulphuric and indeed acetic, which can be 100%.

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#35
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

06/05/2017 9:07 AM

Yes that's true - HCl gas is a covalent compound - therefore not ionized. Only when it is dissolved in water does it become H+ and Cl- and therefore 'hydrochloric acid.' In actual fact the H+ ion (a single proton) is always associated with one water molecule in solution and is better written as H3O+ (hydronium ion).

Here's a question for you: pH = - log10 [H+] (hydrogen ion concentration in moles per liter). In concentrated hydrochloric acid (35% HCl by weight) the concentration of H+ is 1 mole/liter. Therefore the pH = 0.

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#36
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

06/05/2017 9:45 AM

A decimal point out here. 35% is equivalent to 35g/100 ml, more nearly 10moles/litre, making the pH -1

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#38
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

06/05/2017 10:41 AM

Correct! My error.

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#37
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

06/05/2017 10:24 AM

OK, what's the question?

I think you're a factor of about 10 out. 35% w/w is 35gm HCl in 100gm acid as supplied. SG is ~ 1.18 so concentration = 35*10*1.18 = 423gm/l = 423/36.5 = 11.6mole/litre. So assuming (100% ionisation) pH = -1.06.

Ionisation won't be 100% so pH somewhat higher. In principle pH 0 or -1 is possible, whether it ever happens in practice I wouldn't know offhand.

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#39
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

06/06/2017 12:47 AM

Can't be 0 - it's log-scale.

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#40
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

06/06/2017 3:41 AM

What is the logarithm of one?

logb(1) = ?

The logarithmic function

y = logb(x)

is the inverse function of the exponential function

x = by

The logarithm of x=1 is the number y we should raise the base b to get 1.

The base b raised to the power of 0 is equal to 1,

b0 = 1

So base b logarithm of one is zero:

logb(1) = 0

For example, the base 10 logarithm of 1:

Since 10 raised to the power of 0 is 1,

100 = 1

Then the base 10 logarithm of 1 is 0.

log10(1) = 0

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#13
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/25/2017 6:33 PM

Well that's what you link says, but it certainly is not used by chemists.

However it is a common shorthand to write acids as: HX the X referring to the acid radical e.g. Cl, NO3, SO4, COOH etc. In reaction equations in organic chemistry, acetic acid is often abbreviated as HAc, but it is understood as "acetic acid" not "hydrogen acetate."

e.g. the formation of ethyl acetate from ethanol and acetic acid.

C2H5OH + HAc → C2H5COOCH3 + H2O

When writing chemical reactions it is common to use a shorthand such as Φ (phi) to represent C6H5 - (phenyl), so that chlorobenzene (phenyl chloride) can be shortened to ΦCl. Seems lazy but saves a lot of wrist action when taking notes!

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#14
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/25/2017 6:41 PM

Thanks, I'm glad I brought that up,... I have a few questions... but too tire to post..

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#15
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/26/2017 7:43 AM

Just to muddy the water, acetic acid also goes by the name of ethanoic acid, which my spell-checker shortens to ethnic acid.

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#16
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/26/2017 7:55 AM

Yes, that's the systematic name under the IUPAC convention. Acetic acid would be the "trivial name." The trivial names are commonly used for well known chemicals. For example, the IUPAC name for acetone is "propan-2-one." Imagine going into Home Depot and asking for a can of it - they'd probably call the police.

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#17
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/26/2017 11:21 AM

Actually it could be shortened to just propanone. You cannot have a ketone carbonyl on a 3-carbon chain in any other position than at '2'. Either of the other positions would make it an aldehyde.

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#18
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/26/2017 12:19 PM

That's true, but see Wikipedia: some archaic names there:

Preferred IUPAC name Propan-2-one

Other names
  • Acetone
  • Dimethyl ketone[2]
  • Dimethyl carbonyl
  • β-Ketopropane[2]
  • Propanone[3]
  • 2-Propanone[2]
  • Dimethyl formaldehyde[4]
  • Pyroacetic spirit (archaic)[5]
  • Ketone propane[6]
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#20
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/26/2017 12:26 PM

That's it! I'm calling it pyroacetic spirits from now on!

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#21
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/26/2017 12:38 PM

Wikipedia must have used a ghost writer.

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#23
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/26/2017 2:10 PM

I'd like some pyroacetic spirits on my arugula. Yum.

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#41
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

06/09/2017 12:17 AM

phoenix911,

Not quite on the 200 proof portion of your answer. The constant boiling azeotrope is 95% ethanol at atmospheric pressure, so you get 190 proof ethanol. There are many methods for getting rid of the water, however.

--JMM

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#24

Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/27/2017 7:49 PM

Acetic acid can be produced from ethanol by Aqueous-Phase Oxidation. Is this what you are referring to?

Formation of Acetic Acid by Aqueous-Phase Oxidation of Ethanol with Air in the Presence of a Heterogeneous Gold Catalyst

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#25
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Re: Acetic Acid (Ethyl Acetate) from Ethanol

05/28/2017 9:55 PM

No, (s)he is doing a fermentation. (S)He posted earlier on how to make a fermentation tank.

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