Getting rid of esters

[rubelstrudel]

I have just completed distilling 100l of sugar wash on my new still. (And, yes, that's all turbo, I know -shit in shit out.) I have gathered about 10L of pure spirits. (plus a few liters of lower quality tails.) The problem is that they all smell strongly of some unknown ester. Well, I recon it's mainly ethyletanoate since this is a sugar wash. It is not unpleasant as such, just a lot of it.

Is there any smart way of getting rid of these esters? If it is ethylethanoate it is difficult getting rid of by distilling since it has boiling point at 77.1C.

Dillute, coal filter and redistill?

[fizzix]

Never made that much at once during my turbo days, but the odor is etched in my nose hairs.
Activated charcoal filtering DOES help. But turbo is turbo in any quantity.

My first charcoal filter tower was PVC with a plastic funnel. I do not recommend that at all -and it's against all that's holy here.
Graduated to a nice stainless filter system for all my neutrals.
Just FYI.

I wish you well with your alcohol and best wishes!

[der wo]

More common is the name ethyl acetate. It smells like glue.
If the smell is during the whole run, then it must be another substance. Ethyl acetate is easy to remove with the foreshots. For a good neutral you want get rid of all traces of it. Diluting and redistilling is the common way to clean up neutrals, if the normal double distilling protocol is not clean enough. What definetely helps is to add a base before distilling (not into a wash! Only into spirits, low wines and feints!) like soda, natron, caustic soda. Search for a thread "vodka lab analysis results I am pissed" or similar.

[rubelstrudel]

In my nose it smells more like "wine". It is the most common ester in wine after all. I'll look up the thread der wo recommends.
The previous run with turbo was fine really. But I let that one ferment at very low temperatures. This last batch fermented much faster and warmer.

I'll experiment onwards with both filtering and redistilling with high PH . Nice to see the difference..

Right now I am simply enjoying how well behaved the still is. It is only the third time I light it up, and it has behaved admirably now all day long. I lowered my takeoff and have been pulling about 1l/h all day. Temperature on the top of the column has been following all the well behaved curves and the product coming out, if we disregard the winey smell, is just what the doctor ordered.

[6 Row Joe]

I run mine through a Brita water filter. I think it helps.

[20literpotstill]

I've been running all my cuts on secondary distillation so I can get through the initial distillation and give the kitchen back to my girlfriend quicker. I run 13 gallons of wash, either fruit or corn/barley, in three primary runs tben one secondary run. I keep the first 250ml of the secondary as foreshots, which I use to wash off the magic marker labeling on my mason jar covers. I write down the vapor temperature range from my column, and the proof, run date and recipe number on each subsequent mason jar, after diluting the primary ABV to 35 to 38% for the secondary run. I run everything through Mr. Coffee activatedcharcoal discs which I lay into my stainless funnel, replacing it when the hearts start dripping. I fill the mason jars with 700ml each and run until I'm getting less than 25% alcohol off the raccoon pisser. I keep the jars that distilled from 170 to 180 degrees Fahrenheit, and from 142 down to 125 proof as hearts. I run the rest of the heads and tails in my next secondary run. My whiskey hearts get diluted to 110 proof with distilled water and I put into a 5 liter charred oak barrel for a few months before bottling the whiskey. If I'm a little short of filling the barrel, I take the cuts closest to the hearts and dilute to 110% before adding to the barrel. I do basically the same thing with my fruit brandy, except I keep it in mason jars and dont run through tbe activated charcoal water filters. I add frozen liter bottles of water to the sink full of water (about 20 gallons) to keep the water about 69° throughout the run. It takes about 20-25 bottles to finish the run, which I pump into the worm column with a 12V aquarium pump attached to a little alarm battery. I just run the water back into the sink. The burn and the stink is gone!

[rubelstrudel]

Ah. When you are working with whisky, you want to retain a bit of those esters. I am now trying to find a way to remove all those esters to make an as pure as possible ethanol neutral.

Tomorrow I am going to do an experiment. I will take everything that ended up as 95% from todays run and throw it back into the boiler with some fresh water and a couple of tablespoons of Caustic Soda (NaOH - Sodium Hydroxide). Stir until dissolved and test PH. Stop adding NaOH when PH rises. Ethyl acetate reacts with sodium hydroxide when the two are mixed. This is called ester hydrolysis and yields ethyl alcohol and sodium acetate.

CH3CO2C2H5(aq) + NaOH(aq) --> C2H5OH(aq) + CH3CO2Na(aq).

Sodium Acetate should precipitate out of the solution. This should work with other acetates as well.

Now. If I add to much NaOH there will be a surplus of OH- in my "wash", making it basic. Wether this will carry over through the distillation process will remain to be seen. I do not think this will happen. At least as long as I am producing azeotropic ethanol. I'll just have to save a strip or two of litmus paper and see how the PH is after.

I did a small test with NaOH and my distillate today. Dilluted to about 40%. One sample got added a sprinkling of NaOH and one did not, for control. Stir and wait for a minute. The reaction wasn't visible in any way, but after a few seconds the NaOH treated sample smelled noticeably less of EthylAcetate. So I believe this is worth a try.

[der wo]

I think it's better to reach a pH higher than 7.
1g caustic soda per liter 40% will give you probably around pH 11, if I remember right.

[rubelstrudel]

Thats probably right. Some of my NaOH will be converted though. At least I hope so.

[zapata]

oh- will definitely not distill over through a reflux still!
ethyl acetate should be easy to remove with fores and heads, if not you are running too fast and/or not cutting enough. It forms several azeotropes, so traces of it come over more or less throughout heads.
Treating low wines (or distillate of any kind really) with a base does absolutely work. I use washing soda to treat low wines.
In hopes of producing as few esters as possible, I treat my neutral washes with far more sterility than my flavored washes get. Fewer bacteria mean fewer acids mean fewer congeners. So I will use heat to sterilize the wash, micron filters on the aeration pump, star san the fermenters, use air locks etc. None of which I do with flavored washes. And of course, keep your yeast happy, pitch a sufficient amount and ferment them at a controlled temperature.

[rubelstrudel]

Zap, that shows some serious dedication. Right now I am learning to treat the worst of the worst to become halfway acceptable. My next batches of wash I'll try to implement some of your measures, and use a better recipe to avoid as much esters as possible. .... "micron filter on the aeriation pump" - however. Hehe. You're way ahead of my simple game.

[WIski]

6 row joe wrote;
I run mine through a Brita water filter. I think it helps.

Is this a plastic body filter made for water that would break down chemically while filtering high proof spirits? I sure wouldn't want plastic carcinogens in my hooch............

[6 Row Joe]

6 row joe wrote;
I run mine through a Brita water filter. I think it helps.

Is this a plastic body filter made for water that would break down chemically while filtering high proof spirits? I sure wouldn't want plastic carcinogens in my hooch............

Yep it is a plastic body but according to Brita it is BPA free which is good. Heck there are carcinogens in charcoal and small amounts of lead in glass that you store your supplies and finished products in. There is BPA in the thermo paper receipt that you get at the cash register at the grocery store. I should get some charcoal and a stainless funnel to be safe.

[fizzix]

6 row joe wrote;
I run mine through a Brita water filter. I think it helps.

Is this a plastic body filter made for water that would break down chemically while filtering high proof spirits? I sure wouldn't want plastic carcinogens in my hooch............

Yep it is a plastic body but according to Brita it is BPA free which is good. Heck there are carcinogens in charcoal and small amounts of lead in glass that you store your supplies and finished products in. There is BPA in the thermo paper receipt that you get at the cash register at the grocery store. I should get some charcoal and a stainless funnel to be safe.

Hey 6 Row --I hate to be THAT guy, but Britas cannot be discussed. Plastics discussion of ANY kind, unless a product is proven with data to be safe, is verboten.
Britas have pretty much been proven to be otherwise. What's safe for water and food often breaks down in the octane of alcohol.

I hate to be a dick while trying to keep you safe, so I apologize. Better me though, than some hard-liner here.

[6 Row Joe]

6 row joe wrote;
I run mine through a Brita water filter. I think it helps.

Is this a plastic body filter made for water that would break down chemically while filtering high proof spirits? I sure wouldn't want plastic carcinogens in my hooch............

Yep it is a plastic body but according to Brita it is BPA free which is good. Heck there are carcinogens in charcoal and small amounts of lead in glass that you store your supplies and finished products in. There is BPA in the thermo paper receipt that you get at the cash register at the grocery store. I should get some charcoal and a stainless funnel to be safe.

Hey 6 Row --I hate to be THAT guy, but Britas cannot be discussed. Plastics discussion of ANY kind, unless a product is proven with data to be safe, is verboten.
Britas have pretty much been proven to be otherwise. What's safe for water and food often breaks down in the octane of alcohol.

I hate to be a dick while trying to keep you safe, so I apologize. Better me though, than some hard-liner here.

Got it.

[kiwi Bruce]

The problem with plastics is... Ethanol is very good at dissolving esters and esters are a major building block in most plastics...even though phthalate esters, a common plasticizer and very toxic "shown to damage liver and testes" You read that right...your TESTES...BALLS to you and I. Phthalate is being replaced by safer products, but the replacements are still esters and will still dissolve in "High Test" ethanol. Don't rely on the manufacturers. They aren't expecting someone to put "High Test" into or around their product. But if you want to drink something that will FU@#K UP your balls go right ahead...not me, I like my balls just the way they are.

[rubelstrudel]

Ok, so I put my 6l of very-ester-spirits back in the boiler, added 30 liters of water and two spoonfuls of NaOH. That took care of the smell of Ethyl Acetate. After about a minute after adding the lye, the low wine didn't stink so much of "wine" any more. Then I put the boiler on and distilled my spirits a second time. This time I took out about 2 dl of fores and put in my camp fuel cannister, and I stopped the still as soon as the temperature started rising. I didn't bother collecting the last two-three deciliters.

At at about 55 minutes/liter, it took all day. But at least the end result is much cleaner than what I had at the start. At the moment i am not able to differentiate between the bottles. Maybe I'll be able to taste/smell some development through the run in a day or so. My utter complete inexperience comes to play here. Now that the overwhelming smell of ethyl acetate is gone, I am back to not knowing what I am supposed to look for.


Anyway. When I emptied the boiler, there was a fine dusting of some powder in the bottom. Presumably Sodium Acetate. The water left didn't feel soapy, so I may have spent all of the lye hydrolyzing ethyl acetate. Maybe I should have put in even a bit more. There was still a whiff of the ester when I opened up for cleaning.

[der wo]

Ethanol is very good at dissolving esters and esters are a major building block in most plastics.

PET and PVC contain esters. PP and PE don't.
Brita would be very stupid, if they would use PET or PVC. Someone would find out and noone would buy it anymore.
If the spirit you want to filter isn't hot and doesn't contain much foreshots, IMO PE (or at least HDPE) and PP are safe. If we trust PTFE in distillation, because we read in chemical resistant charts, that it is safe for ethanol vapor, I don't know why we don't trust the same chart with cold ethanol and PP and PE. I often smile when I see a thread with a new distiller who is unhappy with the taste of his first product and a member sees a plastic funnel somewhere on the pic of his still and is sure, that the problem is dissolved plastics.
But a Brita filter is a toy. Many distillers filter through more than 2 meter charcoal. And they have a reason for this. A few cm simply don't help much.

[zapata]

Zap, that shows some serious dedication.

Not really. It's a few details, but hardly much time or expense. Most use heat to dissolve their sugar, I just make sure there is enough heat to pasteurize. A hepa filter for the air pump is $5, the air pump IDK, $10? I keep starsan on hand for beer and wine, but a small bottle is probably $10? And temp control, well I probably went overboard, it COULD be as simple as choosing the right yeast for your habitat, but I have a controlled upright freezer that can hold a full drum but the freezer was free

[rubelstrudel]

A little update

I control checked my observations with a chemist friend, and it seems I have been doing it correctly - at least seen from a chemists viewpoint. NaOH is just about perfect for hydrolyzing ethyl esters in a low wine. Exactly what it does to other esters is a bit more of a open case, but my big problem was Ethyl Acetate. The NaOH reacted with ethyl acetate and created sodium acetate that precipitated out of the solution, and converted the ethyl-part back into ethyl alcohol. With the amount of ethyl acetate I had in my original product I could have thrown in even more than the two tablespoons I used. A bit extra does not carry over through the distillation process and keeps more esters from being created.

In my resulting distillate, I can still smell ethyl acetate in the first bottle. But after that it is not present in my product. All in all a positive experience and a fun way to use practical chemistry.

[kiwi Bruce]

Ethanol is very good at dissolving esters and esters are a major building block in most plastics.

PET and PVC contain esters. PP and PE don't.
Brita would be very stupid, if they would use PET or PVC. Someone would find out and noone would buy it anymore.

We are dealing with nubee's here and I'd rather discourage the use of plastics with new people until they understand the difference between a PETie, PVCie or a POOPie ... the phthalate esters were banned in the EU within 90 days of them discovering how bad they really are, Canada Aussie and home followed almost immediately, they are still allowed in the US and they are still being used, FOUR YEARS LATER!...so yes, in the US Brita could still be using ANY of the bad plastics that are banned where you are. Just sayin...the HD has this rule for a very good reason.

Hey 6 Row --I hate to be THAT guy, but Britas cannot be discussed. Plastics discussion of ANY kind, unless a product is proven with data to be safe, is verboten.
Britas have pretty much been proven to be otherwise. What's safe for water and food often breaks down in the octane of alcohol.

I hate to be a dick while trying to keep you safe, so I apologize. Better me though, than some hard-liner here.

I'd rather be a dick that lose my junk...or have someone else lose theirs ...stay away from plastic! Just saying

[6 Row Joe]

Sorry guys. I read on a couple other sites that recommended a Brita or comparable filter to run your product through. You guys here are very knowledgeable and I have learned a lot in the last few days. I am no chemist for sure but some of you are. I don't mean to start a shit storm here but I hope other newbies read along and heed the warning. I smelled and tasted and made my cuts and thought a little filtering could make it just a little better. The batch I didn't filter turned out just fine. I seemed to get more out of some oak chips to smooth things a bit. Thanks for the info. You are all great and very smart about your craft. 6 Row

[kiwi Bruce]

6 Row Joe, don't apologize...it's not a mistake, you haven't offended anyone and believe me this is not a "Shit storm" ...when they happen they are ugly and people get "warnings" from the Mods...and sometimes people just "go away" they are removed from the site, and not without just cause. The HD philosophy is, and always has been "Iron sharpens iron" There are some very smart people here who are more than willing to share the huge pool of knowledge and experience they have accumulated with the rest of us, so that we can sharpen our skills and not have to reinvent the wheel or in this instance the still or the wash or the...you get the picture. Just have some fun and keep on stilling.

[6 Row Joe]

6 Row Joe, don't apologize...it's not a mistake, you haven't offended anyone and believe me this is not a "Shit storm" ...when they happen they are ugly and people get "warnings" from the Mods...and sometimes people just "go away" they are removed from the site, and not without just cause. The HD philosophy is, and always has been "Iron sharpens iron" There are some very smart people here who are more than willing to share the huge pool of knowledge and experience they have accumulated with the rest of us, so that we can sharpen our skills and not have to reinvent the wheel or in this instance the still or the wash or the...you get the picture. Just have some fun and keep on stilling.

Thanks Bruce.

[rubelstrudel]

In conclusion to my original question: What to do about loads of esters? - Here is an update of what i Have done.

After the first distilling I dumped everything back in the boiler with clean water and two tablespoons of NaOH to hydrolyze the Ethyl Acetate. This worked wonders. The smell of Ethyl Acetate disappeared in seconds and after my second distilling I could clearly see Sodium Acetate precipitated out of the low wine. Judging from the pH of what was left in the boiler after the second distilling I could have put in even more NaOH - apparently everything I threw in was converted to Sodium Acetate and ethanol.

Now I had this double distilled and fairly clean product. But there was still some Ethyl Acetate smell in the heads, and a slight whiff of gym socks in the tails. So I put the definite hearts away and dilluted everything else down to 40% and did a slow coal filtering. After filtering I could no longer discern any off odours from my product. Not bad for something that started off as 50l of fast fermented turbo wash.

At the same time I had set up a tincture with stuff I had available. Clementine Peel, root of Sweet Fern and Cinnamon. The Sweet Fern I collected from the garden. This tincture I used to put flavour to my now 40% neutral, and it is actually really good right away. Sweet Fern is supposed to get even better with a bit of aging, so in the cupboard my bottles went.

I have a colleague that broke his foot in three places two weeks ago. He is coming back to work next week and I promised to have some medicine ready for him when he came back. My first proper production was then christened "Medigin" and given this label:

Medigin label

Now I have to find some glue. That turned out to be more difficult. No glue in the house.

my first production

[kiwi Bruce]

A thin white flower and water paste... hold the label (which is very good, by the way) in place with rubber bands until the flower glue dries.

[rubelstrudel]

Found glue later in the evening. But flour paste would do it.

[charcoal]

In conclusion to my original question: What to do about loads of esters? - Here is an update of what i Have done.

After the first distilling I dumped everything back in the boiler with clean water and two tablespoons of NaOH to hydrolyze the Ethyl Acetate. This worked wonders. The smell of Ethyl Acetate disappeared in seconds and after my second distilling I could clearly see Sodium Acetate precipitated out of the low wine. Judging from the pH of what was left in the boiler after the second distilling I could have put in even more NaOH - apparently everything I threw in was converted to Sodium Acetate and ethanol.

Now I had this double distilled and fairly clean product. But there was still some Ethyl Acetate smell in the heads, and a slight whiff of gym socks in the tails. So I put the definite hearts away and dilluted everything else down to 40% and did a slow coal filtering. After filtering I could no longer discern any off odours from my product. Not bad for something that started off as 50l of fast fermented turbo wash.

At the same time I had set up a tincture with stuff I had available. Clementine Peel, root of Sweet Fern and Cinnamon. The Sweet Fern I collected from the garden. This tincture I used to put flavour to my now 40% neutral, and it is actually really good right away. Sweet Fern is supposed to get even better with a bit of aging, so in the cupboard my bottles went.

I have a colleague that broke his foot in three places two weeks ago. He is coming back to work next week and I promised to have some medicine ready for him when he came back. My first proper production was then christened "Medigin" and given this label:
medigin_mini.png

Now I have to find some glue. That turned out to be more difficult. No glue in the house.
medigin_with_label.jpg

I used the same method. Worked very well. It is a nasty chemical but very powerful.

PSA. Sodium Hydoxide WILL REMOVE YOUR SKIN IF YOU TOUCH IT.

[Tut69]

oh- will definitely not distill over through a reflux still!
ethyl acetate should be easy to remove with fores and heads, if not you are running too fast and/or not cutting enough. It forms several azeotropes, so traces of it come over more or less throughout heads.
Treating low wines (or distillate of any kind really) with a base does absolutely work. I use washing soda to treat low wines.
In hopes of producing as few esters as possible, I treat my neutral washes with far more sterility than my flavored washes get. Fewer bacteria mean fewer acids mean fewer congeners. So I will use heat to sterilize the wash, micron filters on the aeration pump, star san the fermenters, use air locks etc. None of which I do with flavored washes. And of course, keep your yeast happy, pitch a sufficient amount and ferment them at a controlled temperature.

"oh- will definitely not distill over through a reflux still!"...
I'm fairly new so don't beat me up when I ask why not reflux?

[whiskymonster]

Somebody linked here from reddit talking about converting store bought eth acetate into drinkable hooch with a handful of lye.

For anyone who came her from reddit, whilst this might theoretically work please dont take the information in this thread to mean this isnt a terrible idea.

Converting a little ethyl acetate from a relatively clean ferment is one thing, using it as feedstock is entirely another.

Figured some of you old hands would weigh in and drive this idea into the ground where it belongs.