Methanol concentrate in the tails according an EC study

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Kareltje
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Re: Methanol concentrate in the tails according an EC study

Post by Kareltje »

engunear wrote:Hmmm. Interesting.

Just to check my sanity, I calculated and plotted the partial pressure of the dominant constituents here. It has been observed that some of us don't understand partial pressure and its role, and I would be the first to agree (I have n=1 evidence of this: me, so don't be offended). Boiling points say one thing, but partial pressure means that things come off below their boiling point.

So I plotted the partial pressure using the equations and constants from http://ddbonline.ddbst.com/AntoineCalcu ... ionCGI.exe" onclick="window.open(this.href);return false;" rel="nofollow

The partial pressure magnitude order follows the boiling points. i.e. methanol > ethanol > water. Not really surprising. But it says to me that the expectation that methanol would concentrate in the heads is not just about boiling point. By "concentrate in the heads" I mean if the concentration in the wash is X, the concentration in the heads is > X.

By the way, if any of you are thinking of learning a computer language, try Python. Even if you are not, but use excel regularly for calculations, try it. Its great for this kind of stuff, and once you get over the hump, you will kick yourself every time you open excel out of habit. I've added the code for the graph FYI. Python is free (comes native on macs), incredibly powerful (e.g. used by US Met office for weather predictions), and fun. OK, I'll stop the off-topic plug.
I must admit that partial pressure is not my best subject, but the very first post in this thread shows partial pressures of ingredients depending on the percentage of ethanol. So not only dependant of temperature, but also of the other present substances.
In this graph at the right side, above 45 %ABV, the volality of methanol is higher than that of ethanol. That is at the start of a run. At the left, the volality of methanol is lower than that of ethanol, that is at the end of a run.
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Re: Methanol concentrate in the tails according an EC study

Post by thecroweater »

@ Enguneer I for sure do not doubt your dads story, not one bit but your conclusion might be off. As an example I reasently toured a well known distillery and after the tour we sampled a line. Now they gave us a new make and all their range from that, the "white dog" was possibly the worst spirit I've drank but the last sample was a vodka ran 16 times. I was literally embarrassed for them as my tastes detected that they had removed compounds I would associate with fore shots otherwise it was a crisper higher proof version of its progenitor. The problems I see are two fold, the base mash and a lack of good cuts. Now if the POWs as is very likely had a sub par mash/wash and not a great understanding of cuts the result is unlikely to be sterling. As for hangovers there are wide range of causes and the very best libations can make you unwell if you over indulge, have an empty stomach insufficient vitamins (as almost a given with POWs) or a lack of water. Dehydration and/or deplention of vitamins is probably the cause of what most ppl call hangovers and has virtually nothing to do with methanol. Menthol becomes highly dangerous when consumed in the absence of ethanol, it is a compound not conducive to life so limiting its inclusion in spirits via fermenting methods and removable fractions is an important part of distillation.
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Re: Methanol concentrate in the tails according an EC study

Post by Bagasso »

Kareltje wrote:In this graph at the right side, above 45 %ABV, the volality of methanol is higher than that of ethanol. That is at the start of a run. At the left, the volality of methanol is lower than that of ethanol, that is at the end of a run.
It sounds to me like you are thinking of the ethanol content of vapor but the chart, if I'm reading it right, is talking about the liquid in the boiler.

For example, if you do a single/first run then the ABV of ethanol in the boiler might be around 10% or less. At this concentration methanol would be less volatile than ethanol and you will probably get it coming over, in a pot still, through the entire run and there could be a fraction later in the run with a spike in methanol concentration.

Now, if you follow the advice often given here to water down low wines to around 40%, you get methanol right around the same volatility as ethanol at the start of the run and then it drops as the run goes on leaving you with the same situation with just a shift on where the methanol comes over. The point of course is that unless you load your boiler with low wines well over 40% (>60%) you will not cut the methanol out by doing a fores cut.

The silver lining, is that the fores/early heads cut in the first run will be cutting out what is thought of, based only on boiling temps, as tails. None of this would negate the importance of good cuts. It just changes the concept of what it is that is being cut out.
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Re: Methanol concentrate in the tails according an EC study

Post by Kareltje »

41_brzinaisparljivostidijagram.jpg
Ah, it works! (Placing attachments!)
Bagasso: I indeed thought about the strength of the vapor. My mistake! :oops:

But as you stated: most people will dilute the load of the boiler to 40 %ABV or less, so only the left part of the graph applies. Unless you have a column with a lot of plates: on the top plates the right part might be interesting.


I found another figure that I have saved some time ago:
Figure 8. Relative volatility of congeners and ethanol.PNG
This shows the relative volality of other congeners and clearly shows why acetaldehyde and ethylacetate are easily driven out. Luckily!

Complication: I think these volalities are measured in mol, not in gram or ml! A y/x of 5,5 at 20 %ABV would give a vapour of over 100 %ABV!

But still: as the volality of methanol is almost equal to the one of ethanol at 40 %ABV and is much less than the one of ethanol at low %ABV, one would expect that the ratio of methanol/ethanol would diminish during a run. But it does not.
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Re: Methanol concentrate in the tails according an EC study

Post by Bagasso »

Kareltje wrote:Unless you have a column with a lot of plates: on the top plates the right part might be interesting.
Edwin Croissant made this other thread, ABV dependent volatility of fusel oils where they talk a bit about columns and the problem that this shifting volatility poses in them.
Complication: I think these volalities are measured in mol, not in gram or ml! A y/x of 5,5 at 20 %ABV would give a vapour of over 100 %ABV!
I'm not sure I understand what you mean by y/x of 5,5. This graph isn't like the Temp/ABV chart on the parent site. None of the graphs in the original post or the graph you posted gives a relation to vapor ABV.
But still: as the volality of methanol is almost equal to the one of ethanol at 40 %ABV and is much less than the one of ethanol at low %ABV, one would expect that the ratio of methanol/ethanol would diminish during a run. But it does not.
I'm not sure exactly how it would work but I think it would be very different to the idea that most of it comes off in the fores. It might start at a certain ratio dependent on ethanol ABV then drop as the ethanol ABV drops and then rise again when the temp hits the spot where it overcomes its low volatility.
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Re: Methanol concentrate in the tails according an EC study

Post by Kareltje »

As far as I understood it, y/x is the volatility, meaning the ratio of a ingredient in the vapour divided by the ratio in the fluid.
Measured in %ABV it can be calculated from the temperature diagram.
F.e. at 5 % in the liquid the boiling temp. is 96 degr C and the concentration in the vapour is about 37 %, so y/x is 37/5 = 7,4.
with liquid is 40 %ABV, temp is 84 degr C and vapour is 77,5 %ABV, so y/x = 77,5/40 = 1,94.

I understood that is the definition of volatility.

But as I said: it is not my forte. In the figure Edwin Croissant gave at 40 %ABV the volatility is about 3, so either it can nog be in %ABV (3 * 40 %ABV = 120 %ABV!!) or I am very mistaken.
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Re: Methanol concentrate in the tails according an EC study

Post by engunear »

Sorry for being so thick and not grasping the significance of that graph. Looking but not seeing. Ah, the mixed blessing of realizing you are an idiot and learning something unexpected! Like the lawyer joke "what do you call it when a lawyer drives your new Ferrari off a cliff?", "A mixed blessing."

But if I read it right, it means that a fractionating column would pull methyl alcohol off first because a good one quickly gets to close to azeotrope at the top, so it operates on the right at the top. Ethyl acetate would also come off as well (which it does). But not because of simple vapour pressure constants.

So a plausible recipe for whiskey would be to put in in a fractionating column, let it stabilise, pull off till little nail-polish smell remains, then open wide and do normal cut at the tail. Yes?
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Re: Methanol concentrate in the tails according an EC study

Post by Kareltje »

engunear wrote:Sorry for being so thick and not grasping the significance of that graph. Looking but not seeing. Ah, the mixed blessing of realizing you are an idiot and learning something unexpected! Like the lawyer joke "what do you call it when a lawyer drives your new Ferrari off a cliff?", "A mixed blessing."
I only recently felt it that way, although I must have had a lot of this Aha-Erlebnisse or Eureka's in my life. Never felt it so distinct. Funny how you describe it perfectly!! :P

On topic:
I do not have a fractionating column, not even a normal column, so I do not really know about its behaviour. But as I understand the previous discussion, there is a azeotrope of methanol and water, independent of the azeotrope of ethanol and water.

The EU report about removing of methanol says things about a method to do it, but it is not really feasible: too complicated. too expensive.
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Re: Methanol concentrate in the tails according an EC study

Post by Bagasso »

Kareltje wrote:As far as I understood it, y/x is the volatility, meaning the ratio of a ingredient in the vapour divided by the ratio in the fluid.
Measured in %ABV it can be calculated from the temperature diagram.
You mean like the ABV/Temp chart in the parent site for calculating the ABV of a vapor from the ABV of a liquid but I think these graphs show volatility relative to the volatility of ethanol (hence the name of the graph). That is why this graph has ethanol as 1. It is the baseline.
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Re: Methanol concentrate in the tails according an EC study

Post by der wo »

Yes. The graph shows (if we trust it), that under 40% ethanol, methanol would concentrate in the tails, over 40% it would concentrate in the heads. But both concentrations are very ineffective in comparision to the concentration of acetaldehyde and ethyl acetate in the heads. So if we distill high proof to concentrate the methanol in the heads, a much greater heads cut was needed to get rid of the methanol than of the fores smell. So probably when we have cut successfully much of the methanol, all the fruity esters are cut too. Bad for whiskey and brandy, only good for neutral.
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Re: Methanol concentrate in the tails according an EC study

Post by engunear »

As a regular user of a fractionating column, but mainly for clean alcohol and grappa, it is not my experience that fruit flavours concentrate in the heads. For grapes, also citrus, anise, juniper ... the fruit flavours are terpenes not esters (yeah, I know peaches, strawberries, pineapple, apple etc are esters). I've not put whiskey through the column, but to my nose the smell of the heads in a pot still is not much fruit. Esters get formed during ageing as the longer alcohols combine with the acids. So a methanol reducing whiskey run, though probably a waste of time as there is not much there to begin with, would probably not affect flavour all that much, besides reducing ethyl acetate and a few similar compounds.
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Re: Methanol concentrate in the tails according an EC study

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der wo wrote:Yes. The graph shows (if we trust it), that under 40% ethanol, methanol would concentrate in the tails, over 40% it would concentrate in the heads. But both concentrations are very ineffective in comparision to the concentration of acetaldehyde and ethyl acetate in the heads. So if we distill high proof to concentrate the methanol in the heads, a much greater heads cut was needed to get rid of the methanol than of the fores smell. So probably when we have cut successfully much of the methanol, all the fruity esters are cut too. Bad for whiskey and brandy, only good for neutral.
Yes and acetaldehyde is significantly more toxic than methanol so that is a good reason to chuck the fores, bad taste of far less toxic ethyl acetate aside.

Another consideration for methanol in brandy would be not using pectinase since it would appear starting with the least concentration of methanol in the wash is preferable.
Excluding pectin before it goes into the still not necessarily during fermentation, the methyl esters will hydrolyse with increasing temperature for any given pH(hydrolysis is much faster under strong acid or strong base).
So not overheating pulp and adding some calcium carbonate to buffer the pH might help to keep the majority of pectin in the pulp which you can then strain out maybe.
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Re: Methanol concentrate in the tails according an EC study

Post by johnnyv »

Just found a paper on boiling point of methanol in various aqueous concentrations.
https://www.google.co.nz/url?sa=t&rct=j ... GUuiHac38A" onclick="window.open(this.href);return false;" rel="nofollow

% Methanol,B.P. (ºC),B.P. Elevation (ºC)
90 69.04 4.34
80 73.84 9.14
70 77.73 13.0
60 79.49 14.8
50 82.92 18.2
40 81.79 17.1
30 85.57 20.9
25 87.95 23.3
20 89.49 24.8
15 91.14 26.4
10 92.64 27.9
5 96.03 31.3

Ethanol shows similar BP increase with water. Probably Propanol and isopropanol as well as they are all water miscible and strong hydrogen bonding. Unlike water miscible but much lower hydrogen bonding acetone and acetaldehyde.
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Re: Methanol concentrate in the tails according an EC study

Post by engunear »

Yes and acetaldehyde is significantly more toxic than methanol so that is a good reason to chuck the fores, bad taste of far less toxic ethyl acetate
aside.
Thats a good post. Welcome. Yeah, methanol gets a bad rap. Its toxic and kills people, though that is pretty uncommon and quite hard to do. Acetaldehyde, as you say, smells terrible and is more poisonous.

As an aside acetaldehyde is fun to play with, a solid at room temperature and it burns with these whispy clouds of solid. Oliver Sachs's great book Uncle Tungsten describes a world where you could buy all these chemicals at the local supplier and take them home to play with, and blow yourself up if you are an idiot. Now, school kids get raided when they bring some ammonium nitrate home from the farm. A different world. But I digress.
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Re: Methanol concentrate in the tails according an EC study

Post by der wo »

I don't think acetaldehyde is a problem. The volatility is so high. Even without cutting any fores, a week airing and it's ok probably.
Edit: Not recommended of course.
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Re: Methanol concentrate in the tails according an EC study

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der wo wrote:But both concentrations are very ineffective in comparision to the concentration of acetaldehyde and ethyl acetate in the heads. So if we distill high proof to concentrate the methanol in the heads, a much greater heads cut was needed to get rid of the methanol than of the fores smell. So probably when we have cut successfully much of the methanol, all the fruity esters are cut too. Bad for whiskey and brandy, only good for neutral.
I have heard that methanol smells sweet and some people go as far as calling it pleasant. That makes me wonder if it is even a guilty party of the fores smell.

I started to type out a reply about the chart and the numbers posted by johnnyv but started thinking about azeotropes and did a quick check on the wikipedia entry for Azeotrope tables.

Methanol does not seem to form an azeotrope with water or ethanol but it does form one with many others. The thing is that the BP of all of its mixtures are below 70°C.

Feels like we are going around in circles.
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Re: Methanol concentrate in the tails according an EC study

Post by engunear »

I don't think acetaldehyde is a problem.
... but is methanol actually a problem? This is a good thread because it forces us to think hard, but I'm not convinced it solves any problem. That being said we know from another thread that some people did die in Australia due to home brewed distilled spirits but without knowing what they did. Maybe if you use boiled fruit you can get the pectin up high enough you can do it.
Bad for whiskey and brandy, only good for neutral
My experiments with a column with whiskey and grappa (proto brandy) produce heads that are just plain stinky. I get no estery smells. Now maybe thats because they are buried, and if one had a really good ester producing yeast one would find esters in the heads. But maybe the key esters are made due to wood interaction i.e. post distillation.
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Re: Methanol concentrate in the tails according an EC study

Post by der wo »

Bagasso wrote:I have heard that methanol smells sweet and some people go as far as calling it pleasant. That makes me wonder if it is even a guilty party of the fores smell.
At least wikipedia says, methanol and ethanol have almost the same smell.
Bagasso wrote:I started to type out a reply about the chart and the numbers posted by johnnyv but started thinking about azeotropes and did a quick check on the wikipedia entry for Azeotrope tables.
I always be astonished by azeotrope datas. So illogical! Only by the way.
engunear wrote: ... but is methanol actually a problem?
No problem probably. But many distillers think it is a problem and think it can be solved with cutting the fores. Both is wrong probably.
engunear wrote: This is a good thread because it forces us to think hard, but I'm not convinced it solves any problem. That being said we know from another thread that some people did die in Australia due to home brewed distilled spirits but without knowing what they did. Maybe if you use boiled fruit you can get the pectin up high enough you can do it.
I remember. I think, one of them is lying. Somebody added methanol.
My experiments with a column with whiskey and grappa (proto brandy) produce heads that are just plain stinky. I get no estery smells. Now maybe thats because they are buried, and if one had a really good ester producing yeast one would find esters in the heads. But maybe the key esters are made due to wood interaction i.e. post distillation.
The first heads are always very stinky with a column. Yes. Definetely a fores cut is good IMO. But generally I disagree with you. I often pour jars which are alone too chemical fruity into the hearts. At least if I want to age it a long time. I believe, here are the fruity flavors. But yes, perhaps I undervalue the creation of esters by the wood. But fruity esters? Hard to say because of the time factor.
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Re: Methanol concentrate in the tails according an EC study

Post by engunear »

I think, one of them is lying. Somebody added methanol.
There were two cases. In one, the dad had a bottle of methanol unlabelled, and added it. In the second there was no evidence of that, and from the coroners report it sounded like they had fermented all kinds of stuff together. It was very unclear as they did not keep detailed records. Its possible they added methanol, but its quite hard to purchase in Australia because people would drink it.
I often pour jars which are alone too chemical fruity into the hearts. At least if I want to age it a long time.
We are one there! Ahhh, for a gas chromatograph so we could actually find out whats in those heads!!
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Re: Methanol concentrate in the tails according an EC study

Post by Bagasso »

engunear wrote:That being said we know from another thread that some people did die in Australia due to home brewed distilled spirits but without knowing what they did. Maybe if you use boiled fruit you can get the pectin up high enough you can do it.
Is this the story: Homemade grappa only drink consumed by three men who died in Ballandean

Something is wrong with that story. A bunch of unlabeled containers were found that contained ethanol, methanol and caustic soda. "Joshua told police the boys asked his father to make the drink and watched him make the alcohol inside the house with contents of several containers."
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Re: Methanol concentrate in the tails according an EC study

Post by engunear »

Interesting. The thread that goes into this in more detail is here. http://homedistiller.org/forum/viewtopi ... l#p7413977

But I think I agree with der wo, they had unlabelled methanol in the shed. They were stoned and drunk. To be sure that the liquor had no added methanol is a stretch.

Our problem is we think and read, but don't have the instruments. I'd love it if someone who can get methanol could mix it with ethanol and put it through a good column and see how much boiling point depression they get. Because if they get a significant BP depression it tells us that we pull a significant portion out in the heads. I have the column and the will but not the methanol. Frustrating.
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Re: Methanol concentrate in the tails according an EC study

Post by johnnyv »

Bagasso wrote:
der wo wrote:But both concentrations are very ineffective in comparision to the concentration of acetaldehyde and ethyl acetate in the heads. So if we distill high proof to concentrate the methanol in the heads, a much greater heads cut was needed to get rid of the methanol than of the fores smell. So probably when we have cut successfully much of the methanol, all the fruity esters are cut too. Bad for whiskey and brandy, only good for neutral.
I have heard that methanol smells sweet and some people go as far as calling it pleasant. That makes me wonder if it is even a guilty party of the fores smell.

I started to type out a reply about the chart and the numbers posted by johnnyv but started thinking about azeotropes and did a quick check on the wikipedia entry for Azeotrope tables.

Methanol does not seem to form an azeotrope with water or ethanol but it does form one with many others. The thing is that the BP of all of its mixtures are below 70°C.

Feels like we are going around in circles.
Azeotropes can be broken, for instance adding benzene to ethanol and water breaks that azeotrope by changing the interactions between the water and ethanol.
Complex solvent mixtures often do not behave anything like single or simple mixes.

I design coatings and adhesives for a living.
I once had to make a primer based on a water soluble binder and I couldn't use water or alcohols due to requirements of subsequent build coats, A mix of three solvents including a ketone an ester and a aromatic hydrocarbon worked even though none of them would solvate the resin alone or in pairs.

So yes we are going round in circles, although perhaps it may emphasize that you can not rely on distillation to sort out all your problems and have to look to the mash/must design and also post aging to give the best outcome.
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Re: Methanol concentrate in the tails according an EC study

Post by LWTCS »

Here is a little insight to whiskey run results with three separate systems.
A pot still is R1.
A two plate hybrid is R2.
And a six plate column is R3.

Note R3 how the Active Amyl Alcohols (esters) have increased in spite of more distillation cycles.
And R2 is a slight reduction on the Active Amyl Alcohols compared to pot stilling.

One might assume that the 6 plate system would eliminate even more of the Active Amyl Alcohols.
But it seems clear that the plates will ultimately entrain some compounds to the point where some of these compounds are actually more concentrated on a plated column. This is why plated columns do indeed make a flavored spirit even though abv can be quite high. And protracted refluxing can further promote esterfication and entrainment of esters on the plates even though the extra refluxing can enrich the abv.

Hope I didn't drift too far off of the OP's intended subject matter?
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Re: Methanol concentrate in the tails according an EC study

Post by Bagasso »

johnnyv wrote:Azeotropes can be broken, for instance adding benzene to ethanol and water breaks that azeotrope by changing the interactions between the water and ethanol.
Complex solvent mixtures often do not behave anything like single or simple mixes.
Of course but it has to be done on purpose.
So yes we are going round in circles, although perhaps it may emphasize that you can not rely on distillation to sort out all your problems and have to look to the mash/must design and also post aging to give the best outcome.
That is an old approach around here. It is one of the reasons turbo yeasts, high ABV mashes are frowned upon.
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Re: Methanol concentrate in the tails according an EC study

Post by Bagasso »

LWTCS wrote:Hope I didn't drift too far off of the OP's intended subject matter?
Well methanol stayed the same in R1 and R2 and only dropped by 3 mg/L in R3.

Just bringing it back on topic.
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Re: Methanol concentrate in the tails according an EC study

Post by LWTCS »

Bagasso wrote:
LWTCS wrote:Hope I didn't drift too far off of the OP's intended subject matter?
Well methanol stayed the same in R1 and R2 and only dropped by 3 mg/L in R3.

Just bringing it back on topic.

:)

Also to add,,,,,, with respect to what we do,,, Methanol simply gets far too much credit by so many hair splitting egg heads and/or nubes.
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Re: Methanol concentrate in the tails according an EC study

Post by Bagasso »

LWTCS wrote:Methanol simply gets far too much credit by so many hair splitting egg heads and/or nubes.
+1

It gets a bad rap for sure. Fruit juices can have up to 80 mg/L and nobody says that it is causing their juice to stink, burn or cause massive hangovers.
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Re: Methanol concentrate in the tails according an EC study

Post by engunear »

Hi LWTCS, thanks for posting that. Not quite what I'd asked for, but equivalent.
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Re: Methanol concentrate in the tails according an EC study

Post by CraftyZA »

How do commercial breweries deal with methanol in high pectin fruit distillates?
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Re: Methanol concentrate in the tails according an EC study

Post by NZChris »

CraftyZA wrote:How do commercial breweries deal with methanol in high pectin fruit distillates?
That question is covered in the link provided in the OP.
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