Removing ethyl acetate by room temp fractionation

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Re: Removing ethyl acetate by room temp fractionation

Postby engunear » Thu Apr 21, 2016 12:44 pm

"is his alcohol just ethanol" ... yeah, no. But with those acids I figured the ethyl esters would dominate as the ethyl alcohol would dominate.

"complex mix hypothesis" was just the statement that we have esters and ketones e.g. acetone and who knows what else. Nothing controversial.

But I'm figuring we are at end-game here. We know that bicarb alone has low enough pH. We have a good experiment that worked and demonstrates the key principles. Maybe repeating the expt with some vinegar and the cleanest alcohol we can find might be useful, as it is just one ester this thread is on. And most of us don't have those other organic acids, nor do we care.

In the Nine Rules of Debugging, they talk about "making it fail" so you can apply your fix and show it works. Flip it back and forth, so to speak. When you can do that you really know you have it nailed. So maybe the experiment with vinegar, in a home setup, is in order. I'll get my hands on a 6l setup next week, just the right size for this.
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Re: Removing ethyl acetate by room temp fractionation

Postby Bagasso » Thu Apr 21, 2016 5:29 pm

engunear wrote:"is his alcohol just ethanol" ... yeah, no. But with those acids I figured the ethyl esters would dominate as the ethyl alcohol would dominate.

I agree but sometimes small amounts of certain compounds will dominate.

"complex mix hypothesis" was just the statement that we have esters and ketones e.g. acetone and who knows what else. Nothing controversial.

I actually think it probably fits the best.

But I'm figuring we are at end-game here. We know that bicarb alone has low enough pH. We have a good experiment that worked and demonstrates the key principles. Maybe repeating the expt with some vinegar and the cleanest alcohol we can find might be useful, as it is just one ester this thread is on. And most of us don't have those other organic acids, nor do we care.

In the Nine Rules of Debugging, they talk about "making it fail" so you can apply your fix and show it works. Flip it back and forth, so to speak. When you can do that you really know you have it nailed. So maybe the experiment with vinegar, in a home setup, is in order. I'll get my hands on a 6l setup next week, just the right size for this.

I have used sodium hydroxide and bring the pH to around 12. Let it sit over night and the next day the low wines will have lost a lot of smell. The thing is that they still "stink". I think stink is too general a term. What they no longer have is fruity sweet smells.

It looses a lot of the solventy smell and heat as well but that taste that I thought early on was tails, then thought it was sugar bite, followed up by looking into water quality and finally I am thinking is nutes, always made for a bad drink.
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Re: Removing ethyl acetate by room temp fractionation

Postby engunear » Fri Apr 22, 2016 11:18 am

Interesting!

Just an aside, but a bit of background on why think experiments have to be well designed to demonstrate what we are discussing here:

Talking to an advertising person for a major Australian brewery once, she told me that although people will talk about the beer they drink, and how much superior it is to all the other beers (and we are talking VB, Tooheys etc, not the boutique beers), if you put their beer in a blind lineup they cannot pick it. There was even the case recently where a beer that won a boutique beer contest as "Vaucluse Bitter", labelled to imitate the mass produced Victoria Bitter (very ironic) was in fact Victoria Bitter.

So smell measurements are inherently unreliable in my book. The best smell experiments are double blind, and "pick the odd one out of three" is a reliable method.

A second story about measurement - Monster Cables are these heavy speaker cables that cost hundreds of dollars a set. The Hi-Fi world is full of stories about how good they are. And they boast "low oxygen copper" and have arrows showing which way to connect them. But if you talk to a speaker designer, they point out that the series voicecoil impedance is so high that their very low resistance can have no effect compared to a decent piece of light flex. As to the arrows, they violate the electrical engineering principle called "reciprocity". So why do sensible people believe this crap? Imagine a salesman has convinced you to buy some. The price is ouch. You take them home, put on your best record, on some system that cost a bomb, and listen. And it sounds great. Are you going to admit to yourself that they sound the same as before? No way. But if you put the same cables in a double-blind experiment, then the benefit disappears, and circuit theory rules.

So when someone tells me that they left a bottle for three months and it smelled much better at the end, I give it a Mythbusters "Plausible", not "Proven". And we don't have chromatographs to play with, so we have to be careful. I live a lot of my day job measuring things and its a prick to get a good result.

Not being critical mind, well, other than trying to inject healthy doubt. So when we have a mix of smells, and smell tests a day or a month apart, I'm thinking "I want to believe, but do I?". The chemistry is solid. So I tried to pick something where the ethyl acetate was so strong I could convince myself and failed, for reasons understood.
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Re: Removing ethyl acetate by room temp fractionation

Postby Bagasso » Fri Apr 22, 2016 1:51 pm

engunear wrote:So smell measurements are inherently unreliable in my book. The best smell experiments are double blind, and "pick the odd one out of three" is a reliable method.

Agreed but that is all I have. That is all Grim had as well.

There is a point where things are just different or rather where the difference is big enough so that it isn't just bias.
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Re: Removing ethyl acetate by room temp fractionation

Postby engunear » Sat Apr 23, 2016 11:55 am

Agreed. And you know your nose better than I do. Mine is erratic at best.

Have you ever tried a 2/3 double blind test? Or even a test with two or more glasses, you know what is in them but you don't know which is which, now identify them? Whenever I've done such a test I've been shocked at how poorly I've done. They are also a lot of fun, at the extreme end: a bunch of friends, 6 whiskeys or wines, one person to do the pouring and blinding. Some food as that is a lot of tasting. Put in a curve ball - something you think is pretty ordinary, e.g. Johnnie W Red. See how it fares. This is off topic, but still. The key lesson for me has been that preconceptions are incredibly powerful.

When I get time, the following might be in order:

1. Distill some hearts with calcium oxide or sodium hydroxide and carbon to get the cleanest alcohol I can make.
2. Add acetic acid and distill. This should make the dread compound in sufficient quantity.
3. Put some aside.
4. Put remainder with calcium oxide or sodium hydroxide, water, and distil.
5. Compare. Will blinding be necessary?

Because if we know the method works (right base, right qty, right temperature, right time) then we also know that what remains is not an ester.

A question, in Grim, he said his heads were estery. I wonder if the reaction had not gone through yet, so a little reflux might have given clean heads?
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Re: Removing ethyl acetate by room temp fractionation

Postby Bagasso » Sat Apr 23, 2016 6:02 pm

engunear wrote:Have you ever tried a 2/3 double blind test?

No, it's just me and my hooch. All I have is side by side.

Sometimes I wonder what I'm actually shooting for. What if pure etho/water taste bad?

I've read people say that they don't use AC because it adds a flavor they don't like. What if it is like RO or distilled water which some people dislike dispite being really pure? Could it be stripping away flavors and exposing the hydrocarbon solvent taste that belongs to etho? Not the smell but the taste, since it is supposed to smell sweet.

Because if we know the method works (right base, right qty, right temperature, right time) then we also know that what remains is not an ester.

I figured that much because the "stink" I was left with was not fruity or solventy. It was a musty scent.

A question, in Grim, he said his heads were estery. I wonder if the reaction had not gone through yet, so a little reflux might have given clean heads?

What does estery mean though, sweet, fruity? There are other chemicals which smell fruity without being esters. Ethyl aldehyde, for example, is said to smell like green apple and ethyl maltol is said to smell like caramelized sugar or cooked fruit and it is a pyrone.

The more I look into it the more complex the mix seems to be.
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Re: Removing ethyl acetate by room temp fractionation

Postby engunear » Sat Apr 30, 2016 3:40 pm

Well I have run the bottle left for months. And I get the nailpolish to solventy shift.

The first fraction is still nailpolish though, so I'm wondering if it takes a bit of time to go through. This is reported by Grim as well. Some time in full reflux would be a good idea.

Also if Grim is saying that temperature is the key, then water content is probably also important as it dissolves the calcium carbonate and pushes the temperature up before boiling starts.

I had a glass of the stuff on the bench for A/B comparisons and my wife cleaned the kitchen. Oh well.
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Re: Removing ethyl acetate by room temp fractionation

Postby Bagasso » Sat Apr 30, 2016 11:39 pm

engunear wrote:The first fraction is still nailpolish though, so I'm wondering if it takes a bit of time to go through. This is reported by Grim as well. Some time in full reflux would be a good idea.

As croweater pointed out earlier, acetone is also nailpolishy, it is bound to be concentrated in the first fraction and is probably not affected by alkali. No amount of time is going to make a difference if that is the case.

I think it brings us right back to the "complex mix hypothesis".
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Re: Removing ethyl acetate by room temp fractionation

Postby MDH » Sun May 01, 2016 4:45 pm

I am sticking by the argument that if you argue ethyl acetate is responsible for harsh spirits, you are also arguing that all highly aged spirits are therefore harsh, because it is well known that aged spirits are oxidized and contain very large amounts of it. Harshness will always be the fault of aldehydes, specific alcohols, and certain short-chain fatty acids (Some of which are actually precursors to better tasting compounds with age).
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Re: Removing ethyl acetate by room temp fractionation

Postby Bagasso » Mon May 02, 2016 12:03 am

MDH wrote:I am sticking by the argument that if you argue ethyl acetate is responsible for harsh spirits, you are also arguing that all highly aged spirits are therefore harsh

Not necessarily. The argument is that heads may be harsh, in part, due to ethyl acetate.

This paper Flavour Components of Whiskey. II. Ageing Changes in the High-Volatility Fraction
shows 533mg of of ethyl acetate per liter of absolute alcohol in 6 year old whiskey.

Compared to Photonic's Fusel Oil Lab Analysis Results # 1 which shows 2,124.4 mg/l at 67.65 ABV heads.

Adjusting the 533mg/l absolute to 68% ABV gives 355 mg/l for the whiskey. That's almost 6 times more ethyl acetate in photonics heads fraction than the 6 year old whiskey.

Taking into account that the sensory threshold for ethyl acetate is around 200 mg/l and that the whiskey in that study had 148 mg ethyl acetate, per absolute liter, out of the still it would seem that good cuts where made despite there still being ethyl acetate in the green distillate.

Then we have what this says "The sensory detection threshold for ethyl acetate is very low and can be challenging to detect in some beers due to masking effects of other flavours."

It isn't out of the question to believe that the flavors that develop in a highly aged spirit outpace the rise in ethyl acetate.

Still, just comparing to the numbers in photonic's lab results we see that there is a big difference in the amount's of ethyl acetate in his heads fraction and the amount in a highly aged spirit.

ETA: It just dawned on me that if that 533 mg/l is watered down to 40% ABV the concentration of ethyl aceteate goes down to 213.2 mg/l barely above the sensory threshold making that much easier for the other flavors to mask it. So, while we can say that ethyl acetate goes up in an aged spirit we also have to take into account where the concentration ends up.
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Re: Removing ethyl acetate by room temp fractionation

Postby engunear » Tue Oct 10, 2017 8:35 pm

OK, its not low temp fractional distillation.

Took 550ml of 82% ethanol. A bit fruity but clean enough. Diluted to 40% ABV. Took 30ml off into a glass. Added 2-3ml analytic reagent ethyl acetate. Took 30ml off into a second glass. And a stinky mess that is.

Added 1 tbsp of Calcium Carbonate made as described above. Distilled, then diluted to 40% ABV.

And it is still stinky. So maybe it is proven chemistry, but it seems to me that there is a pH or concentration or time factor missing from the treatment. So is there any chemist watching this who knows how to work out the conditions to make this reaction go through? Should we use sodium hydroxide? How much per liter?

When we know how to jam this reaction through, then if we do it on a some unclean batch, whatever is left is not ethyl acetate.
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Re: Removing ethyl acetate by room temp fractionation

Postby engunear » Tue Oct 10, 2017 9:02 pm

I'm gonna reply to my own post and leave it there as a reminder of the hazards of rushed results. Yes, the early part may have been stinky, but when it was aggregated and compared to glass 2, there was a big reduction in stink. I'm going to let it sit and run some noses over the results to see what they say.
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Re: Removing ethyl acetate by room temp fractionation

Postby der wo » Wed Oct 11, 2017 1:22 am

You could add a stronger base. Caustic soda. I normally add to low wines or feints I want to turn into vodka 1g per liter 40%abv or lower.

But perhaps you only have to wait a little longer. Did you measure the pH?
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Re: Removing ethyl acetate by room temp fractionation

Postby engunear » Wed Oct 11, 2017 1:37 pm

But perhaps you only have to wait a little longer. Did you measure the pH?


... a dangerous question. Pretty soon we'll start acting like ... scientists !!!!! What, you want ... reproducible results? Go wash you mouth out with caustic soda 0.1M for at least 5 minutes at a temperature greater than 30C.
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Re: Removing ethyl acetate by room temp fractionation

Postby der wo » Wed Oct 11, 2017 1:46 pm

I don't understand. Probably it's a joke?

I measured 1g caustic soda in 1l 40% low wines pH 12. Yes, that's probably not nice for teeth. But both the copper and the ss of my still didn't have a problem. I also tried 2g/l. PH 13... Same result after the spirit run. Very clean and no corrision.
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Re: Removing ethyl acetate by room temp fractionation

Postby engunear » Wed Oct 11, 2017 1:53 pm

Absolutely a joke. My frustration rises when I hear things along the lines "I added some X (unspecified quantity) and tasted it three weeks later and it tasted like Y so X causes Y. I get even more frustrated when I write it. So I just love the high level of this thread!
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Re: Removing ethyl acetate by room temp fractionation

Postby MDH » Thu Oct 12, 2017 12:52 pm

http://spiritsjournal.klwines.com/klwin ... alker.html

just read this, hit control+f and type in "Acetate".
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Re: Removing ethyl acetate by room temp fractionation

Postby engunear » Thu Oct 12, 2017 1:09 pm

Curious. It is also the opposite of the suggestion (as previously on this thread) that leaving a bottle free to the air (room temp fractionation) reduces ethyl acetate.

I tried room temp fractionation with a stinky bottle. Not quite heads, but foreshots. For a while I was not convinced it worked. Then life then got in the road and I forgot about it. And when I came back it was free of the stinkiness. Its a hard question for us amateurs, we have a mix of low boiling point aromatics, and we know one is ethyl a. And we can look up the chemistry of ethyl acetate. But thats where it ends.
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Re: Removing ethyl acetate by room temp fractionation

Postby Kareltje » Thu Oct 12, 2017 2:42 pm

der wo wrote:I don't understand. Probably it's a joke?

No wonder:
We have an advertisement for a German car and one of the lines is:
"You are making jokes!"
The stern answer:
"Germans never make jokes!"
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Re: Removing ethyl acetate by room temp fractionation

Postby Bagasso » Thu Oct 12, 2017 3:03 pm

MDH wrote:http://spiritsjournal.klwines.com/klwinescom-spirits-blog/2015/3/12/more-on-canadian-whisky-hiram-walker.html

just read this, hit control+f and type in "Acetate".

Everything I have ever read in making ethyl acetate from ethanol involved oxygen, acetic acid and catalysts at very high temps or some living organism.

Anything to back up the idea that exposure of ethanol to plain old to air makes ethyl acetate?
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Re: Removing ethyl acetate by room temp fractionation

Postby engunear » Thu Oct 12, 2017 3:27 pm

Yeah, and its not the only hint of the subtle smell of bs in that article. Now bs, like rotten shrimp (trasi) is something that is very appealing in low concentrations, but in high it becomes overpowering.

Once we hit around 77oC, that’s where the ethyl acetate comes out—that nice fruity character
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Re: Removing ethyl acetate by room temp fractionation

Postby NZChris » Thu Oct 12, 2017 4:47 pm

Flavour Components of Whiskey. II. Ageing Changes in the High-Volatility Fraction.
K. MacNamara , C.J. van Wyk, O.P.H. Augustyn and A. Rapp, Page 79
http://www.sawislibrary.co.za/dbtextimages/17148.pdf

Similar increases in bourbon whiskey are recorded (Reazin et
at., 1976; Reazin, 1981) and the mechanism involved has been
described by the same workers. By adding a small amount of
radioactive ethanol to a whiskey at the start of ageing, they
found over a 56-month period that this radioactivity is incorporated
into acetaldehyde, ethyl acetate and acetic acid. The
mechanism involves oxidation of ethanol by molecular oxygen
to produce acetic acid via acetaldehyde. Excess ethanol combines
with acetic acid to produce ethyl acetate, and with
acetaldehyde to produce diethyl acetal (Reazin, 1981).
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Re: Removing ethyl acetate by room temp fractionation

Postby engunear » Thu Oct 12, 2017 6:10 pm

OK, I stand corrected!
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Re: Removing ethyl acetate by room temp fractionation

Postby Bagasso » Thu Oct 12, 2017 8:07 pm

NZChris wrote:
The mechanism involves oxidation of ethanol by molecular oxygen to produce acetic acid via acetaldehyde. Excess ethanol combines with acetic acid to produce ethyl acetate, and with acetaldehyde to produce diethyl acetal (Reazin, 1981).


This is vague.

Looking into it I see a lot mentioned in reference to Oxidation mechanisms occurring in wines but they also mention that the process starts with polyphenols and the need for metal ions:

Danilewicz (2003) and then Waterhouse and Laurie (2006) have examined the proposed mechanisms by which oxygen and its intermediate reducing products react with wine constituents, as well the participation of transition metal ions in these reactions. The authors have concluded that oxygen does not react directly with phenolic compounds without the presence of transition metal ions. Moreover, an intervention of iron, copper, and manganese ions in wine oxidation had already been observed (Cacho, Castells, Esteban, Laguna, & Sagristá, 1995).


I'm thinking it might be something similar happening in whiskey or other aged products with the woods offering those needed compounds.

That said, the amount in the Flavour Components of Whiskey for ethyl acetate is 0.17 mg/L per day. It would seem to me that it would evaporate faster than it could be made.
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Re: Removing ethyl acetate by room temp fractionation

Postby MDH » Thu Oct 12, 2017 8:47 pm

Not sure of the relevance of phenols to this discussion. We're talking about oxidation of ethanol. As has been pointed out a few posts above by Chris' citation, alcohol is oxidized by O2 to acetaldehyde, to acetic acid which then reacts with remaining etOH.

Plus, Don Livermore is not the kind of person who spews bullshit. He literally has a PhD in this.

I remain convinced that ethyl acetate is not the culprit of harsh or overtly chemical smelling spirits; but instead basic aldehydes, ketones and other volatile compounds like concentrated diacetyl.
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Re: Removing ethyl acetate by room temp fractionation

Postby Bagasso » Thu Oct 12, 2017 8:58 pm

MDH wrote:Not sure of the relevance of phenols to this discussion. We're talking about oxidation of ethanol. As has been pointed out a few posts above by Chris' citation, alcohol is oxidized by O2 to acetaldehyde, to acetic acid which then reacts with remaining etOH.

From what I quoted. keep in mind it is about wines;
During the non-enzymatic oxidation process, also called chemical oxidation of wine, the oxidative processes is favored by the oxidation of polyphenols containing an ortho-dihydroxybenzene moiety (a catechol ring) or a 1,2,3-trihydroxybenzene moiety (a galloyl group), such as (+)-catechin/(−)-epicatechin, gallocatechin, gallic acid and its esters, and caffeic acid, which are the most readily oxidized wine constituents (Singleton, 1987; Singleton, 2000; Kilmartin, Zou, & Waterhouse, 2001; Danilewicz, 2003; Li et al., 2008).


I was just thinking that nobody cares about oxidation of ethanol in vodka, at least I couldn't find anything on it and I proposed why that could be based on the two things posted, wine and whiskey, being aged products.

Plus, Don Livermore is not the kind of person who spews bullshit. He literally has a PhD in this.

Anyone could have incomplete info.

I remain convinced that ethyl acetate is not the culprit of harsh or overtly chemical smelling spirits; but instead basic aldehydes, ketones and other volatile compounds like concentrated diacetyl.

You could be right but the question was, could you get rid of them at room temp by just airing out?

Especially if the O2 creating ethyl acetate isn't the culprit.
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Re: Removing ethyl acetate by room temp fractionation

Postby engunear » Thu Oct 12, 2017 11:17 pm

You could be right but the question was, could you get rid of them at room temp by just airing out?


Isn't this likely to need a case-by-case answer? Treatment with bases does not remove solventy smell -> there are solventy smells besides ethyl acetate.

Acetaldehyde has BP 20C, so it is likely to evaporate preferentially. Ethyl acetate has BP 1C away from ethanol, so it is less likely.

Since I have a bottle that I know contains only ethyl acetate, I'm happy to run that test. And we could treat some stinky heads with calcium carbonate to remove ethyl acetate and run the experiment on whatever is left. So much junk in my shed, this won't be much extra. It might take a year.
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Re: Removing ethyl acetate by room temp fractionation

Postby Bagasso » Thu Oct 12, 2017 11:57 pm

engunear wrote:Acetaldehyde has BP 20C, so it is likely to evaporate preferentially. Ethyl acetate has BP 1C away from ethanol, so it is less likely.

But there is a lesser amount than ethanol so if you air out and lose say 1% abv, would that mean that the ethyl acetate is mostly gone?

I mean, we all seem to agree that things don't come off one at a time but things come off with a higher percent at about their BP unless there are azeotropes formed with other chemicals which means the BP is shifted but that would also apply to a normal run and cuts done on that run.

So, you do a standard run but don't do a fores or heads cut. You collect everything up to where the tails start to come over. You take some tails for later but in another container. You now have fores, heads and hearts in a single container, if you leave it open will the fores and heads evaporate, taking some of the hearts with it, would it leave you with a larger hearts portion?

Looking at it another way. You do a normal run. Cut fores and toss. Keep heads, hearts and tails separate. If you air out the heads would it eventually become hearts?

Since I have a bottle that I know contains only ethyl acetate, I'm happy to run that test. And we could treat some stinky heads with calcium carbonate to remove ethyl acetate and run the experiment on whatever is left. So much junk in my shed, this won't be much extra. It might take a year.

What does it smell like? I'm not saying you should but I would probably dip my finger in it and rub a fair amount around my lips just to see if it causes that burning sensation you get from heads.
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