Removing ethyl acetate by room temp fractionation

Post by **francis** » Sun Jun 21, 2015 6:28 pm

So I'm back to trying to remove ethyl acetate again.

Previously I was able to reduce it by putting an airstone in a jar of heads and bubbling for a day whereupon 5% of the volume was lost, and the nail polish smell was greatly reduced. But I'm sure I lost almost as much ethanol as ethyl acetate with that.

Because the ethanol and ethyl acetate have such close vapor points I think we need some sort or reflux to concentrate the ethyl acetate before discarding it.

My current experiment is to build a room temperature fractionating still. I've wanted to play around with this anyway, just because no one else is.

So . . . I made a kind of a mini thumper in a jar. A 10' copper spiral (1/4" od) comes out of the top of the lid. It's bottom end is above the surface of the distillate. A second piece of copper (1/4" od) goes into balsa wood airstone submerged in the distillate. An aquarium pump pushes air in.

The wood airstone bubbles and the vapor laden air exits via the spiral where it tends to recondense, revaporize and recondense again as it works it's way upwards. Almost all of it will recondense, wind it's way down the spiral, and return to the jar.

But some portion of vapor will exit the spiral, and that fraction should be richer in ethyl acetate than ethanol. Or so I hope.

We shall see . . .

It seems ethyl acetate is easier to separate from ethanol when methanol is present. The ethanol / water mix separates from the ethyl acetate / methanol mix. So ironically, if I had more methanol in my wash I would get a sharper cut of ethyl acetate in the heads.

Post by **masonsjax** » Mon Jun 22, 2015 12:57 am

Do you have a pic of this? I think I've got the idea, but a photo should make it all clear. Thanks!

Post by **francis** » Mon Jun 22, 2015 5:07 am

masonsjax wrote:Do you have a pic of this? I think I've got the idea, but a photo should make it all clear. Thanks!

At work, but does this drawing help? I only have paint in windows :-(

Post by **bearriver** » Mon Jun 22, 2015 6:26 am

francis wrote:Because the ethanol and ethyl acetate have such close vapor points I think we need some sort or reflux to concentrate the ethyl acetate before discarding it.

Saying the membership needs reflux to make good cuts, paints some very broad strokes... The process of making cuts is how we make sure that the levels of unwanted substances like EA are kept at an acceptable level. Reflux helps with that cause sure, but only if it fits the style of spirit being made made.

Like carbon filtering, this can be used as a crutch that hinders the learning process. Learning to make a drop that doesn't require post processing is a big win. If you could figure out how to eliminate the oaking process for example, you'd be billionaire.

Why do you think EA is such a concern, even after making good cuts? I'm not trying to knock your efforts or dissuade you from exploring new things. I just think your efforts may be more fruitful if you choose to follow more standard methods of success.

Post by **shadylane** » Mon Jun 22, 2015 7:48 am

How are you measuring the amount of ethyl acetate in the distillate ?

Post by **Jimbo** » Mon Jun 22, 2015 8:20 am

Crazy science experiments for the sake of learning are great, but what are you trying to achieve exactly? Looks like you want to turn heads into something drinkable? Thats a dangerous proposition, there's plenty other compounds that boil off early to worry much more about than Ethyl Acetate which is considered low toxicity, and is low in distilled beverages anyway unless you have a vinegar creating infection. Why are you so concerned about ethyl acetate?

Curious also that you bubbled O2 into your drink thinking youre removing EA. Oxygen exacerbates the problem, not reduces it, due to the oxidation of ethanol into acetaldehyde.

Post by **francis** » Mon Jun 22, 2015 8:26 am

Detecting by smell.

Reduce it then run the heads again with the next batch.

I would love to know how to minimize it's formation in the first place. I am using sodium bicarbonate after the stripping run. I don't think I am under pitching the wash either.

I got lots of this with a turbo wash, but I can smell it still with Birdwatchers TPW.

Post by **Jimbo** » Mon Jun 22, 2015 8:33 am

hmmm. Are you thorough about sanitizing everything? You might have an acetobacter type bacteria in your process. Ethyl Acetate is the ester of Acetic acid and Ethanol. Or maybe youre just very sensitive to the 'sugar bite' in sugarheads. Some of us are more than others. Try making an all grain spirit and see if you pick up the same problem. Id suggest a single malt first. Very easy. Just get your water to 156F and then add 2 lbs milled malt per gallon and wrap up tight for an hour. Cool and pitch. Youll still get heads that need to be cut, but you might be pleasantly surprised.

Bagasso · Post by **Bagasso** » Mon Jun 22, 2015 1:43 pm

I like the idea. One thing to keep in mind is that it might not be ethyl acetate that you are sensing but it really doesn't matter because if your idea works then what ever it is would have been taken care of.

Yeast produce acetic acid so there is always going to be some even without acetobactor infections.

Oxygen is supposed to make things worse but who knows how exact that claim is.

Post by **francis** » Mon Jun 22, 2015 2:08 pm

Jimbo wrote:hmmm. Are you thorough about sanitizing everything? You might have an acetobacter type bacteria in your process. Ethyl Acetate is the ester of Acetic acid and Ethanol. Or maybe youre just very sensitive to the 'sugar bite' in sugarheads. Some of us are more than others. Try making an all grain spirit and see if you pick up the same problem. Id suggest a single malt first. Very easy. Just get your water to 156F and then add 2 lbs milled malt per gallon and wrap up tight for an hour. Cool and pitch. Youll still get heads that need to be cut, but you might be pleasantly surprised.

I think I am very sensitive to it by smell. Definitely an all grain spirit next.

I have my fermenting stuff in the garage, and I do notice vinegar flies hanging around the airlock.

----------------------

Jimbo wrote:Crazy science experiments for the sake of learning are great, but what are you trying to achieve exactly? Looks like you want to turn heads into something drinkable? Thats a dangerous proposition, there's plenty other compounds that boil off early to worry much more about than Ethyl Acetate which is considered low toxicity, and is low in distilled beverages anyway unless you have a vinegar creating infection. Why are you so concerned about ethyl acetate?

Curious also that you bubbled O2 into your drink thinking youre removing EA. Oxygen exacerbates the problem, not reduces it, due to the oxidation of ethanol into acetaldehyde.

Well I'm bubbling air through it, not O2, but I suppose if I had a source of carbon dioxide or pure nitrogen I could use that. Actually I do have a source of CO2, the bubbles from the next wash. I could run a hose from the airlock, to the airstone, but there are also other aromatics in there. Hummm . . . nice ones. I really like the smell of the fermenting wash.

Post by **francis** » Tue Jun 23, 2015 8:29 pm

Well . . . it worked and it didn't. After bubbling for 3 days (I didn't check on it sooner), the nail polish smell is gone. But the volume is down by about 15%. There was no liquid dripping from the bottom of the sprial. So not sure if the spiral did anything more that just an airstone by itself would have done. Assuming the ethyl acetate (if that was the cause) was there at a low concentration in the first place, if it was preferentially removed I would still lose a lot of ethanol (and water) as well. I think the abv is down a bit. I didn't keep notes, but now the hydrometer reads 65%.

Assuming 800 ml of distillate in the jar and 200 ml gone . . . if I had simply re-run it in the next run, could I have recovered 600 ml of ethanol without any ethyl acetate and whatever else was in the 200 ml lost ? Not sure. Anyway 200 ml is not that much. I've spilled more than that in various mishaps for sure. I was discarding this before( after having fun lighting it and watching it burn with a blue flame), but then I realized I could keep it to clean my phone, etc.. The 600 ml left is keepable. It smells neutral. I don't think I need to run it again.

Post by **rad14701** » Tue Jun 23, 2015 9:05 pm

You haven't really proven anything... If anything, you've proven that you hypothesized and experimented improperly... Nothing more... You needed a simple repeatable initial baseline to work from...

Bagasso · Post by **Bagasso** » Tue Jun 23, 2015 10:04 pm

rad14701 wrote:You haven't really proven anything... If anything, you've proven that you hypothesized and experimented improperly... Nothing more... You needed a simple repeatable initial baseline to work from...

I disagree. Even a failure can yield useful information. If nothing else, this proves that a 10ft 1/4" copper air coil won't fraction the saturated stream produced by bubbling.

It also shows that the smell, a taste test would also be in order, can be stripped from a heads fraction. We already knew this but, there is always that question of o2 and distillate producing more heads. Even if true, maybe bubbling gets rid of it faster than it produces it.

Something has to explain the results even if we don't know what it is.

Sure tighter experiment parameters would be better but around here, even if carried out correctly, there always seems to be a strong resistance.

Post by **googe** » Tue Jun 23, 2015 11:20 pm

Could rotary evaporation be used for this?.

Post by **Yummyrum** » Wed Jun 24, 2015 2:26 am

Sorry but I gotta ask ...and hey there might be something in it but.....Would you use a different direction of coil in the southern Hemisphere

Bagasso · Post by **Bagasso** » Wed Jun 24, 2015 9:47 am

googe wrote:Could rotary evaporation be used for this?.

I think they are different ways to skin that same cat but rotary evaporation requires special equipment and you usually want to save the distillate.

This seems to be express delivery of the angel's share.

Yummyrum wrote:Would you use a different direction of coil in the southern Hemisphere

No.

Post by **Jimbo** » Wed Jun 24, 2015 9:49 am

Bagasso wrote: This seems to be express delivery of the angel's share.

Post by **francis** » Wed Jun 24, 2015 10:06 am

If nothing else, this proves that 10ft 1/4" copper air coil won't fraction the saturated stream produced by bubbling.

Well, I am not sure. When I checked on it after 3 days there was nothing dripping from the bottom of the spiral.

I do need better notes. But (a) it's a hobby not a job, and (b) sometimes you need to follow a hunch, then follow up with more care if it works out. I think this could be useful so I will follow up.

Also I should mention I could have done a better job of sealing the entry of the tubes in the lid of the jar. I just made holes. But next run I will seal them with hot glue.

In Riku's ARC still with heads collection the product takeoff point is about half way up. So there is just as much packed column below the takeoff point as there is between the takeoff and the heads reservoirs. It takes a lot of reflux fractionation to separate the ethanol from the ethyl acetate, because they are so close in vapor points. Either a taller column, or more reflux, or less leakage

Post by **Jimbo** » Wed Jun 24, 2015 10:11 am

+1 crazy experiments are a hoot. Just make sure you take at least enough notes to know how to repeat it on teh off chance it works. Many of my experiments dont work (like Dildo Dram). Thats just fine with me. Doesnt mean we wont bust your stones for some good natured entertainment tho.

Post by **francis** » Wed Jun 24, 2015 10:19 am

Jimbo wrote:+1 crazy experiments are a hoot. Just make sure you take at least enough notes to know how to repeat it on teh off chance it works. Many of my experiments dont work (like Dildo Dram). Thats just fine with me. Doesnt mean we wont bust your stones for some good natured entertainment tho.

It's all good fun, and I appreciate all the feedback. I haven't proven anything . . .yet.

Post by **Jimbo** » Wed Jun 24, 2015 10:27 am

Keep at it. Most folks thought Edison was a looney in his day too

Why are you a tomato? If you dont mind me askin

Post by **francis** » Wed Jun 24, 2015 10:56 am

Jimbo wrote:Keep at it. Most folks thought Edison was a looney in his day too

Why are you a tomato? If you dont mind me askin

When I first started I tried turbos, but then I found Birdwatchers TPW. It's simple and works. I did another wash with some chicken feed I had (after pressure cooking it). It stalled, but after adding a couple of cans of tomato paste, it took off again.

Yeast really like tomato.

I found you can use canned dced tomato too, if no salt has been added. It may work better than paste, but you have to use twice as much. It's cheaper though. Moot if you recycle into a sour TPW wash. That's going really well too.

Max_Vino · Post by **Max_Vino** » Wed Jun 24, 2015 11:51 am

I don’t think your going to get much of a separation because the boiling points of the two components are too close together. You don’t have to use the bubbler you will get the same separation simply by opening the jar to the atmosphere. This all corresponds to Raoults law and Dalton’s Law of partial pressure. You would have a better chance at separating them by freezing. The freezing temperature of ethyl acetate is -83.6° C and the freezing temperature of ethanol is -114° C…. so you could immerse liquid in a liquid nitrogen bath and by monitoring the temperature you could affect a separation. The most energy efficient method of doing this would be to put a line trap into a liquid nitrogen bath. You would then bubble your ethanol mixture and pass the vapor through the line trap and then to a secondary condenser. The ethyl acrylate would form a frost on the inside of your line trap. Here is a picture of a line trap.

Max

Bagasso · Post by **Bagasso** » Wed Jun 24, 2015 1:04 pm

francis wrote:I do need better notes. But (a) it's a hobby not a job

Hey I'm on your side but if in the previous bubbling you lost 5% in one day and in this one you lost 15% in 3 days then, nothing was being refluxed.

I'm not saying it can't be done, I'm saying that it seems your room temp coil didn't do it.

engunear · Post by **engunear** » Sat Jul 18, 2015 12:36 pm

A post here taken down by author as it missed the point.

Bagasso · Post by **Bagasso** » Sat Jul 18, 2015 12:56 pm

engunear wrote:Maybe after a few hours open it up a bit faster.

This is why people are still looking for other ways to skin that cat.

Post by **shadylane** » Sat Jul 18, 2015 5:11 pm

Nothing ventured, nothing gained. Even a failed experiment yields information.
Here's a proven way to get rid of some of the unwanted conigers that distillation and cuts missed.

Tomb · Post by **Tomb** » Fri Nov 20, 2015 9:41 am

Shadylane:

Sorry, I am either missing the obvious in the photo or am taking a wry remark seriously.
What process is the photo depicting?

Tom

Post by **raketemensch** » Fri Nov 20, 2015 9:54 am

Tossing a Molotov cocktail very quickly gets rid of any congeners in the alcohol by spreading the alcohol over a wide breathing surface, and also by burning it with fire.

Bagasso · Post by **Bagasso** » Fri Nov 20, 2015 10:06 am

Tomb wrote:Sorry, I am either missing the obvious in the photo or am taking a wry remark seriously.
What process is the photo depicting?

Plain old airing out.

It's actually what the OP is trying to do but they want to speed it up.

Home Distiller