Pure acids and ester production

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RedwoodHillBilly

Re: Pure acids and ester production

Post by RedwoodHillBilly »

der wo wrote: I drank Wild Turkey only once, in a bar. But in a bar I often like something and at home I don't. Or otherwise. This is really strange. For example I tried two times Highland Park 12 in a bar and I didn't like it. But now I have a bottle at home and it tastes good!
Back to the Wild Turkey: I think it was the cheaper 81 proof one. I liked it, because of the deepness, I thought perhaps deep toasted wood gave it cinnamon. And dried fruits, not floral things. And for that low price it's a good quality. Before I buy a Maker's Mark I would buy the Wild Turkey 81 next time. You see, I tasted different things than you. But I don't trust my taste in a bar...

You should make experiment No.1 with lactic acid soon. Then your view on commercial spirits will change probably. You will get a solid opinion, which spirit has lactic esters and which one not.
Agreed on the experiments. I have some lactic, butyric and formic acids on the way right now, they should be in sometime this week. I just have to run off some azeo in my CCVM from failed runs that I've raised the ph using Ca(OH)2.

On the Wild Turkey, I haven't had the 81 in a while, so I went out and bought a bottle. I diluted a sample of each to 30% for comparison purposes. I think that the notes that I'm looking for are more pronounced in the 101. It wasn't a blind test, so there could be belief bias in the results. I tried to exclude that, but being human it is hard to.
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Re: Pure acids and ester production

Post by kiwi Bruce »

MDH wrote:Low aeration, low pitch rates, high temperature, select strain = more fruitiness.

Try WYEAST 1968, 1187, WLP023, Lallemand British Ale. Believe Derek Bell at some point used White Labs' strain Saccharomyces Trois.
You hit the nail with this post MDH...I'm thinking of either, a small batch yeast and microbe fermentation that's added to the low wine distillation (I think it should give some control) or, a small batch yeast and microbe fermentation that's added directly to the primary fermentation ( I don't think there would be any control at all...but who knows ?) and of course... Low aeration, low pitch rates, high temperature and yeast strain and sub-straight suitable to the end product.

but we're drifting away from the original post...that was, not creating the wanted goodies in our own ferments, but purchasing them and adding them drop wish into a wash before running it...not something I can do right now, but I'm interested in the results of others experiments.
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Re: Pure acids and ester production

Post by RedwoodHillBilly »

kiwi Bruce wrote: Red, you may be able to get a lot of the floral/fruity esters with a change to a high ester forming yeast. I'm about to try safbrew WB06 in a single malt wash. It's a Bavarian brewers yeast specifically made to produce high esters and phenols in wheat beer. It's not cheep at $9.00 a pack, but if it will produce the end result I'm looking for it will be worth every penny. The other thing I've been reading about, but have not tried yet, is to ferment at a temperature that's way higher than normal. This stresses the yeast and can make it produce esters. I haven't tried this yet because I don't know if the results would be constantly reproducible. I will post my results with the WB06...it's just a thought, it may help you too.
I'm hijacking my own thread, but your post on WB06 got me thinking (dangerous I know) about trying Lallemand Abbaye Ale yeast. It's another high ester yeast. Maybe we should continue high ester yeast discussions in another thread.
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Single Malt Yinzer
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Re: Pure acids and ester production

Post by Single Malt Yinzer »

As I read this thread I think we should clarify: What is each acid? Carboxylic acid vs catalytic acid. The principals of this thread know this but the readers might not understand it as well. The carboxylic acids mentioned in the thread include: Formic acid, Acetic acid, Butyric acid, Latic Acid
https://en.wikipedia.org/wiki/Carboxylic_acid" onclick="window.open(this.href);return false;" rel="nofollow (posted only for the list of common carboxylic acids)

I'm not a chemist/biologist so I don't know how to quantify what a "catalytic acid" is. Can it be any acid or only specific ones? It looks like sulfuric acid is a very good one. Is it because sulfuric acid is inorganic? Is it solely due to pH? Are organic acids also able to be used as a catalyst? If one would only use one kind of carboxylic acid would it still produce esters?

--------
As I have been reading on the subject it seems that people are preferring longer chain carboxylic (fatty) acids over the their shorter chain cousins.
https://en.wikipedia.org/wiki/Fatty_acid" onclick="window.open(this.href);return false;" rel="nofollow (posted to list the common ones)

Interesting note: I've read people joke about seeing goat heads in muck(dunder) pits:
Decanoic acid (capric acid) is a saturated fatty acid. Its formula is CH3(CH2)8COOH. Salts and esters of decanoic acid are called decanoates or "caprates". The term capric acid is derived from the Latin "caper / capra" (goat) because the sweaty, unpleasant smell of the compound is reminiscent of goats. it is found is the fat of goats.
--------

Speaking of yeast, do we know what makes it a high ester yeast? What does this yeast produce differently than a lower ester one?
I found this: https://www.gastrograph.com/blogs/gastr ... ation.html" onclick="window.open(this.href);return false;" rel="nofollow
There are however different amounts and ratios of esters produced by each different strain of yeast within a species. These different ratios are the result of the yeasts making different kinds of organic acids and alcohols to react and create esters. The yeast will make esters out of whatever acids and alcohols are available. However some yeast produce different acids preferentially.
--------

Der Wo, RHB and everyone else contributing to this thread: Thanks, I'm learning a lot!
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Re: Pure acids and ester production

Post by kiwi Bruce »

RedwoodHillBilly wrote:I'm hijacking my own thread, but your post on WB06 got me thinking (dangerous I know) about trying Lallemand Abbaye Ale yeast. It's another high ester yeast. Maybe we should continue high ester yeast discussions in another thread.
I absolutely agree...Trappist beers are traditionally brewed warmer than most ales and Abbaye Ale yeast is made by five or six companies so it should only cost a couple of bucks...so YES! a new thread please! There must be dozens of HDer's with stakes of experience with the wilder side of the yeasts.
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Re: Pure acids and ester production

Post by RedwoodHillBilly »

Damn, it's going to feel like some of my organic chemistry classes again (without the cool analytical tools). I now have a series of carboxylic acids coming for ester experiments. It'll be interesting to see what the esters formed from the higher alcohols (like those found in tails) are like as well.

1) Lactic acid
2) Propionic acid
3) Formic acid
4) Butyric acid
5) Isovaleric acid
6) Hexanoic (Caproic) acid
7) Heptanoic (Enanthic) acid

I will probably try some of the longer chains later, Octanioc (Caprylic) acid looks promising

I knew going into this that it was going to be a rabbit hole. Even if none of these make it into my likker, at least I'll learn something new.
RedwoodHillBilly

Re: Pure acids and ester production

Post by RedwoodHillBilly »

I started a placeholder thread viewtopic.php?f=39&t=67528#p7485963 as place to discuss using high ester producing yeasts for whiskey so we don't get too off topic in this thread.

After searching the forum, I've seen some mention of high ester yeasts, but no real coherent discussions. I don't have much to contribute to it yet, but I hope that it may be useful in the future.
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Re: Pure acids and ester production

Post by Single Malt Yinzer »

https://www.bruichladdich.com/article/b ... filtration" onclick="window.open(this.href);return false;" rel="nofollow
4 main fusel alcohols, most pleasant is phenylethyl alcohol. Propanol, isobutanol, isoamyl & pentanol are the major contributors.
There's a good start for you.
RedwoodHillBilly

Re: Pure acids and ester production

Post by RedwoodHillBilly »

Single Malt Yinzer wrote:https://www.bruichladdich.com/article/b ... filtration
4 main fusel alcohols, most pleasant is phenylethyl alcohol. Propanol, isobutanol, isoamyl & pentanol are the major contributors.
There's a good start for you.
Good article, thanks. I have some high purity propanol here and was thinking to get some butanol as well. Methanol is easy to get. If I did that I would have the 1st 4 alcohols to play with, maybe I should get some pentanol as well so I have the the 1st 5 alcohols. Damn, 5 alcohols and 8 acids give a large experimental space.
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Re: Pure acids and ester production

Post by der wo »

Single Malt Yinzer wrote:I'm not a chemist/biologist so I don't know how to quantify what a "catalytic acid" is. Can it be any acid or only specific ones? It looks like sulfuric acid is a very good one. Is it because sulfuric acid is inorganic? Is it solely due to pH? Sulfuric acid is not only a good proton donor, but also a good dehydrating agent, what prevents that esters and water turn back again to acids and alcohol. Are organic acids also able to be used as a catalyst? At least citric acid doesn't work. I have tried. If one would only use one kind of carboxylic acid would it still produce esters? I am not sure what you mean. Yes it only needs one kind of acid. But then you don't get many different esters.

As I have been reading on the subject it seems that people are preferring longer chain carboxylic (fatty) acids over the their shorter chain cousins.
https://en.wikipedia.org/wiki/Fatty_acid" onclick="window.open(this.href);return false;" rel="nofollow (posted to list the common ones)
I think, here are opinions about yeast selection and circumstances for the yeast mixed with knowledge about bacterial esters. Your yeast and how you treat it (Temperature, pitching rate, aeration...) has an influence on fatty acids (how many and which ones). When you have a dunder pit, you will get much butyric acid. When you let ferment an unboiled AG for a long time, you get lactic acid. When you let a fermented wash open to atmosphere, you will get acetic acid. Then short chain esters. And then longer ones, but this needs time. And after my experiments I think the fast and easy to get short ones smell very "original".

Speaking of yeast, do we know what makes it a high ester yeast? What does this yeast produce differently than a lower ester one?
I found this: https://www.gastrograph.com/blogs/gastr ... ation.html" onclick="window.open(this.href);return false;" rel="nofollow
There are however different amounts and ratios of esters produced by each different strain of yeast within a species. These different ratios are the result of the yeasts making different kinds of organic acids and alcohols to react and create esters. The yeast will make esters out of whatever acids and alcohols are available. However some yeast produce different acids preferentially.
Very interesting. This is something I thought and looked for, but didn't find. Thanks. So there are no "high ester yeasts", they should be named "high acid yeasts".
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Re: Pure acids and ester production

Post by MDH »

Yeasts do produce esters during the growth phase with the use of an enzyme.

I have a google scholar feed attatched to my google news feed. There are lots of bio / chem engineers in the food industry working on these kind of things all the time.

Was just reading this one from 2015: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4556718/" onclick="window.open(this.href);return false;" rel="nofollow
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RedwoodHillBilly

Re: Pure acids and ester production

Post by RedwoodHillBilly »

MDH wrote:Yeasts do produce esters during the growth phase with the use of an enzyme.

I have a google scholar feed attatched to my google news feed. There are lots of bio / chem engineers in the food industry working on these kind of things all the time.

Was just reading this one from 2015: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4556718/" onclick="window.open(this.href);return false;" rel="nofollow
Perhaps this would be better posted in the High ester yeast for whiskey thread viewtopic.php?f=39&t=67528 that I started to keep this thread on topic.
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Re: Pure acids and ester production

Post by RedwoodHillBilly »

Well, I've got all of the carboxylic acids for my experiments. I'm just waiting for my 98% H2SO4. My plan is to use a standard solution of 15 mL of the various alcohols, 150 uL of the various carboxylic acids, and 15 uL H2SO4 for initial smell tests. I won't drink any of the initial test, just smell them.

I must admit, that the higher carboxylic acids smell pretty rank, but the esters are supposed to smell pretty good. We'll see.
Most smell like puke or worse.

Here is another experiment (that I'll leave to someone else), get drunk, puke into your low wines, add H2SO4 then distill it. :D
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Re: Pure acids and ester production

Post by Single Malt Yinzer »

RedwoodHillBilly wrote:I must admit, that the higher carboxylic acids smell pretty rank, but the esters are supposed to smell pretty good. We'll see.
Most smell like puke or worse.
Here is another experiment (that I'll leave to someone else), get drunk, puke into your low wines, add H2SO4 then distill it. :D
hahaha The things we do to make a better product.
RedwoodHillBilly wrote:Well, I've got all of the carboxylic acids for my experiments. I'm just waiting for my 98% H2SO4. My plan is to use a standard solution of 15 mL of the various alcohols, 150 uL of the various carboxylic acids, and 15 uL H2SO4 for initial smell tests. I won't drink any of the initial test, just smell them.
So the thing I think about with Sulfuric is the unintended consequences. Since in the Fisher esterification process it is the catayst and isn't used up. But it's a powerful acid and won't be happy until it gets used up. With a previous experiment Der Wo used it with less than happy results. I think the amount of sulfuric acid is way to high. Maybe start with 1% and work your way up.

Also, where did you get your sulfuric acid? I want to get in on this action... :)
RedwoodHillBilly

Re: Pure acids and ester production

Post by RedwoodHillBilly »

Single Malt Yinzer wrote:
RedwoodHillBilly wrote:I must admit, that the higher carboxylic acids smell pretty rank, but the esters are supposed to smell pretty good. We'll see.
Most smell like puke or worse.
Here is another experiment (that I'll leave to someone else), get drunk, puke into your low wines, add H2SO4 then distill it. :D
hahaha The things we do to make a better product.
RedwoodHillBilly wrote:Well, I've got all of the carboxylic acids for my experiments. I'm just waiting for my 98% H2SO4. My plan is to use a standard solution of 15 mL of the various alcohols, 150 uL of the various carboxylic acids, and 15 uL H2SO4 for initial smell tests. I won't drink any of the initial test, just smell them.
So the thing I think about with Sulfuric is the unintended consequences. Since in the Fisher esterification process it is the catayst and isn't used up. But it's a powerful acid and won't be happy until it gets used up. With a previous experiment Der Wo used it with less than happy results. I think the amount of sulfuric acid is way to high. Maybe start with 1% and work your way up.

Also, where did you get your sulfuric acid? I want to get in on this action... :)
I read that 10% or so of H2SO4 to the the carboxylic acid is used for the Fischer esterification reaction. I may be wrong, if so please enlighten me.

I ordered the H2SO4 from the same place that I got my phosphoric acid. http://www.dudadiesel.com" onclick="window.open(this.href);return false;" rel="nofollow
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Re: Pure acids and ester production

Post by Single Malt Yinzer »

As for the 1% or 10% ratio I don't know. Thanks for the link!
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Re: Pure acids and ester production

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RedwoodHillBilly wrote:I read that 10% or so of H2SO4 to the the carboxylic acid is used for the Fischer esterification reaction. I may be wrong, if so please enlighten me.
I would rely more on Arroyo's premise that the pH can be lowered to 5.5 to 5... so the amount of H2SO4 will depend on the amount of lye that was present. Concentrated H2SO4 is hugely acidic and it may only take one or two drops to reach the pH that's required.
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Re: Pure acids and ester production

Post by RedwoodHillBilly »

kiwi Bruce wrote:
RedwoodHillBilly wrote:I read that 10% or so of H2SO4 to the the carboxylic acid is used for the Fischer esterification reaction. I may be wrong, if so please enlighten me.
I would rely more on Arroyo's premise that the pH can be lowered to 5.5 to 5... so the amount of H2SO4 will depend on the amount of lye that was present. Concentrated H2SO4 is hugely acidic and it may only take one or two drops to reach the pH that's required.
Exactly, 15uL is only 2 drops or so.
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Re: Pure acids and ester production

Post by raketemensch »

kiwi Bruce wrote: I would rely more on Arroyo's premise that the pH can be lowered to 5.5 to 5... so the amount of H2SO4 will depend on the amount of lye that was present. Concentrated H2SO4 is hugely acidic and it may only take one or two drops to reach the pH that's required.
How about using acid to control the ph in a multi-gen wash instead of backset? I’d imagine we could work out a baseline per gallon.

It seems that most of the experiments so far are with adding dunder to low wines, is anyone working directly with their wash?
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Re: Pure acids and ester production

Post by RedwoodHillBilly »

raketemensch wrote:
kiwi Bruce wrote: I would rely more on Arroyo's premise that the pH can be lowered to 5.5 to 5... so the amount of H2SO4 will depend on the amount of lye that was present. Concentrated H2SO4 is hugely acidic and it may only take one or two drops to reach the pH that's required.
How about using acid to control the ph in a multi-gen wash instead of backset? I’d imagine we could work out a baseline per gallon.

It seems that most of the experiments so far are with adding dunder to low wines, is anyone working directly with their wash?
I guess that I wasn't clear. This is about creating esters from carboxylic acids and alcohols. H2SO4 acts as a catalyst for that reaction. Not about reacting with lye. Now about controlling ph in a mash, many craft distillers (myself included) use phosphoric acid as a ph reducer instead of backset.
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Re: Pure acids and ester production

Post by der wo »

kiwi Bruce wrote:
RedwoodHillBilly wrote:I read that 10% or so of H2SO4 to the the carboxylic acid is used for the Fischer esterification reaction. I may be wrong, if so please enlighten me.
I don't know. I used much less sulphuric acid compared to the carboxylic acid. And I used much more carboxylic acid compared to ethanol. But I think, also Redwoods amounts will work.

I would rely more on Arroyo's premise that the pH can be lowered to 5.5 to 5... so the amount of H2SO4 will depend on the amount of lye that was present. Concentrated H2SO4 is hugely acidic and it may only take one or two drops to reach the pH that's required. The 5.5 is about to have a nice environment for the bacteria, it's not a special pH for the highest esterification.
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Re: Pure acids and ester production

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Here is a new read F.I, Scard...https://www.bostonapothecary.com/wp-con ... m-1920.pdf" onclick="window.open(this.href);return false;" rel="nofollow
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Re: Pure acids and ester production

Post by engunear »

This is a totally amazing thread. My compliments to the contributors.

A question which is off-topic, but at the same time sits better here than any other thread I know of: this thread is about the esterification reaction: acid+alcohol -> ester + water reaction ... which has a reverse.

Noting that Scotch whiskey has no ethyl acetate notes, but they recycle heads, one wonders where the ethyl acetate goes? A well known feature of Scotch is that the stills have finite life. The copper dissolves. So is it possible that the acetate ion dissolves the copper, falling back into the wash, freeing the alcohol? This can be a weaker reaction than the ester formation and still be effective as the heads are recycled multiple times.
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Re: Pure acids and ester production

Post by der wo »

This is a question I gave Single Malt Yinzer for the ester interview:
http://homedistiller.org/forum/viewtopi ... =3&t=68005
The glue smell of Bourbon is obviously ethyl acetate. Produced by vinegar bacterias. Open fermentation seems to be the reason. But why even young Malt Whiskies doesn't have it? They also are fermented open normally. Is the key the fores cut of pot distillation vs no fores cut in continuous distillation. Or are there other causes like the warmer climate in Kentucky than in Scotland?
AFAIK all the fores are recycled in Scotch. But there are also sources claiming they toss them a few times a year. I don't know. Perhaps there is a reaction with copper? Or perhaps the ethyl acetate is such volatile that much of it evaporates before the next low wines where it's added to? Like our heads jars improve from airing?
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Re: Pure acids and ester production

Post by engunear »

I should check my notes but my memory is that Abelour chucks them once per year only during the maintenance period. Its that or Glenlivet (the two in the Spey region I visited.)

A flip question is if not the ethyl acetate, then what dissolves the still? Presumably an acid as copper is stable with bases, which still suggests de-esterification.
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Re: Pure acids and ester production

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engunear wrote:A flip question is if not the ethyl acetate, then what dissolves the still? Presumably an acid as copper is stable with bases, which still suggests de-esterification.
Is it really corrosion of the riser and lyne arm which ends the life of a Scottish potstill? I think it's the boiler. The acids in the boiler, and the agitator chains if they have them (direct fired potstills have agitators, heated with steam coils ones not AFAIK).
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Re: Pure acids and ester production

Post by engunear »

Both I believe. Can't remember where I read it, but it stuck with me as it is unexpected.

There is the story about one of the distilleries that had a ding, and insisted that the new still be made with the ding recreated in case it was important. Now thats clearly apocryphal, but the premise is that the top part was being replaced.
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Re: Pure acids and ester production

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Perhaps it's the acetaldehyde? It's not a real acid, but I just read it has pH 5. Every fermentation produces acetaldehyde.
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Re: Pure acids and ester production

Post by engunear »

Possibly. But it could be the acetate, which would tell us where it goes, without requiring a explanation along the lines of "it accumulates and one a year it is discarded, and December barrels have a higher concentrate than January but, but with ageing and blending it all gets lost. I could find none at all in a June un-aged spirit. And I hate it.
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Re: Pure acids and ester production

Post by der wo »

Like I wrote for the interview:
Or are there other causes like the warmer climate in Kentucky than in Scotland?
What I mean is, that the hot climate perhaps helps vinegar fly infections. Colder climate -> less ethyl acetate. So in general a Scotch has less glue smell than a Bourbon. Also possible I think. We will see if he has an answer.
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