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Craftbrewer
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Have I made drinkable ethanol from metylated spirits
I thought I would share my simple experiment of making drinkable ethanol from methylated spirits as of interest to anyone.
In Australia, I used a clear brand as my starter. Diggers Methylated Spirits. The bottle and spec sheet state 95%ethanol, <5% water. I assumed from
this the ethanol is sourced from natural fermentation and distillation then the denaturing agents added.
http://www.recochem.com.au/index.php/products/consumer_produ...
Contacting the manufacturer, They would not state what they were, BUT were very persistant that their methylated spirits had no toxic ingredients to
humans. Over here companies are worried about being sued as they know drunks drink the stuff, so make it " non-toxic".
OK lets look at the facts
In methylated spirits, what they do is add basically three categories of additions.
1. Sometimes a colouring agent to tell you not to drink it.
2. an agent that smells terrible to tell you dont drink it.
3. an agent that tastes terrible so you dont swallow it.
So I set up a good fractional column and gave it a go
1. There is no Methanol in it. It is about 95% ethanol, The temperature racing and sitting at a flat 78.5C right thru the distillation
2. Do the fractional distillation and in the remaining wash (I collected 90 percent of the volume), leaves a hydrocarbon that smells very much like
thinners used in car paint.
3. Add acid and fractional distill and you remove a salt crystal that is the main bittering agent
The important bit
4. The remaining is all ethanol and one minor agent and it has a very fruity/floral smell.
5. Add water to this at 50% ethanol strength, and the compound comes out of solution (it goes cloudy)
6. It is non toxic by the way, leaves a extremely slight tingle at the front of the mouth, and is quite pleasant.
BITTERESS
Utterly no problem here. a simple acid addition, renders the bitterness agent a salt, and it wont distill out. The final product is not bitter at all,
in fact very drinkable in terms of bitterness. Dare I say it, any alcoholic could drink themselves silly on the stuff.
FLAVOUR
Now the fun begins. This is where we get into some chemistry.
No matter whether its a fractional distil, or many distils, a compound comes thru that is described by all I test as " sweet smelly, a cross between
thinners, and roses, or a taste like medicine."
Now lets look at separating and identifiying the flavouring compound, and even removing it to make pure drinking ethanol.
Again lets look at the facts
1.Digger insist all there metho is NON TOXIC to humans
2. Then the flavour that is distilled even thru fractional distillation means its has properties similar to water and ethanol. Totally solubile
(Miscible in ethanol), comes out of solution in water at certain level (insoluble)
3. I can separate a crystal at minus 18C from a solution of 43% distillate , BUT that might be water.
4. I cant rule in or out either an ester or an aromatic hydrocarbon.
5. Smell is always described as sweet, and not petrol like. Various descriptions from fruity, floral to slight solvent-like.
Lets look at an ester.
Its probably industry based, strong, and as stated non Toxic
BUTYL ACETATE – its good, fruity, and used in industry. Its a known solvent, and totally soulble in ethanol, poor in water it seems. While fruity
hasn't been described by people, its not a stretch to imagine that as a smell. One problem is the boiling point, 128C, well outside the normal
distillers range.
Its also clear we could be dealing here with an aromatic hydrohydrocarbon with an azeotrope that matches and even combines with the water/ethanol
azeotrope, and thus impossible to separate thru normal distillation, no matter how refined you make it. So thats leads to you the benzene family of
hydrocarbons. So what molecules do match ALL the things we know about what we have distilled. Eliminate those that smell like petrol and its industry
and you remove most. Then find ones that smell sweet, and have boiling points arround 80C (ethanol) Only one really falls into place.
But lets deal with one mentioned a lot
BENZENE – it fits the bill. Impossible to separate from water/ethanol mixture, boiling point right in the range of home distillers. However two main
problems.
1. Its smell and flavour is described as petrol smells. thats not what one gets. It just doesn't smell like that.
2. Its toxic to human health, and Diggers have insisted they dont have any toxic compounds to human health.
so that can be ruled out
BUT the contenter that raises it head and fits the bill
CYCLOHEXANE
Most interesting compound, a deviritive of benzene.
It ticks all the boxes
1. Non toxic to humans
2. described as sweet, fruity, alderhyde, permume, slighty solvant
3. will bind to ethanol/water distillation, impossible to separate thru normal distillation
4. used in distinfectants, soaps, detergents and household chemicals to give a pleasant flavour, very safe
5. freezes at 5 c, boils at 80c (ethanol boils at 78C)
It just ticks all the boxes. Well almost, flavour described as petrol=like, which is rather obscure. Is those describing it as slightly solvent cover
that bill, I just dont know. Some decriptions have detergent like smells, and its not that at all. Objectively cant rule this in or out, BUT overall
to me this is the compound I have to separate
So two contenders
Butyl acetate and cyclohexane. I favour cyclohexane, as its physical properies match well to water/ethanol, it is not soluble in water, so the
cloudiness. We do havean aromatic hydrocarbon, its has a noticable smell, and is safe to consume. BUT we also now have a way to remove it, no matter
which it is.
next is how to remove it
OK How to remove the cyclohexane, thus making basically ethanol and water.
Lets revise the critcal facts
1. in ethanol, cyclohexane is totally soluble.
2. in water, cyclohexane is totally insoluble.
So when we dilute our distilled ethanol with water to about 43% ethanol, being soooo much water there, the cyclohexane comes out of solution and forms
a haze. This haze is an emulsion (like fat in milk, extremely small droplets thru out the liquid.) Being an emulsion, we now can actually "see" the
cyclohexane, so if we remove the haze, we remove the cyclohexane.
Now I was looking at various methods of removing an emulsion and there are a few, BUT wanted a backyard science method of doing it. I found two very
simple methods. One I have tried with great success and detail below. The other I am still yet to test so will report when that is ready
And to go weird on people here are two facts about olive oil
3. cyclohexane is miscible with olive oil
4. ethanol/water mixes dont disolve in olive oil
What this means is cyclohexane will disolve with olive oil, no matter what the concentration is of either. So if I add olive oil, it will float on the
surface, and absorb some of the cyclohexane that makes contact with it. If I shake the bottle, more will make contact with it and be absorbed. BUT
only so much will over time.
Mow apply a little bit of lateral thinking and you will see where this goes.
Ethanol and water are also are miscible. Leave ethanol and water in a glass and over time, the ethanol evaporates and your left with water. Put olive
oil over ethanol and water and it seals it from the atmosphere, and very little evaporates. BUT if its an olive oil and cyclohexane mix, well it still
stops the ethanol evaporating, as its mixed with the water, but the cyclohexane can evaporate.
Thus the olive oil absorbs the emulsion of cyclohexane, and evaporated it to the atmosphere at the same time. my 5 litres of 43 percent hazzy
distilled ethanol totally went from you couldn't see thru it to light haze in a day, and clearish in two days to totally clear in 3 days. The olive
oil was simply decanted off.
The end result was very clean, no sign of the cyclohexane taste at all. Perfectly drinkable vodka. A further dilution down to 10 percent showed
utterly no haze at all, meaning I had removed ALL the cyclohexane (or at least to below taste threshold levels).
So there you go, a very simple method that worked a treat.
Thought I would share this
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blogfast25
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Whatever you do with your end product (sell it or consume it yourself) have it at least analysed by a competent and independent laboratory.
It's a nice post but you're at risk of trying to bend reality into what you want it to be, without straightforward empirical evidence on the
composition of your end product.
"Ethanol and water are also are miscible. Leave ethanol and water in a glass and over time, the ethanol evaporates and your left with water."
for instance shows you know less than you think you do. Water and ethanol form a azeotrope at the high end of ethanol content: water and ethanol can
thus not be separated beyond the azeotrope with mere evaporation of distillation. It's one of the best known azeotropes in the world, BTW.
Don't take this the wrong way but I wouldn't consume your product if my life depended on it, w/o some legit certificate of analysis. No one else
should either.
You make some other categorical statements:
”There is no Methanol in it. It is about 95% ethanol, The temperature racing and sitting at a flat 78.5C right thru the distillation”
W/o analysis you can’t be that certain.
”BITTERESS
Utterly no problem here. a simple acid addition, renders the bitterness agent a salt, and it wont distill out.”
There are quite a few bitterants out there. W/o knowing which one is in the bought product how can you be so sure of your statement?
You may well be right about all these things but it seems to me there's a lot of wishful thinking in your post.
[Edited on 28-9-2014 by blogfast25]
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HeYBrO
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Now just test it with HPLC!
Edit: blogfast beat me
[Edited on 28-9-2014 by HeYBrO]
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IrC
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You mentioned Butyl Acetate but not Ethyl Acetate which is often used to denature ethyl alcohol.
http://en.wikipedia.org/wiki/Specially_denatured_alcohol
Also: http://en.wikipedia.org/wiki/Denatured_alcohol
From this: "Different additives are used to make it difficult to use distillation or other simple processes to reverse the denaturation. Methanol is
commonly used both because its boiling point is close to that of ethanol and because it is toxic. Another typical denaturant is pyridine. Often the
denatured alcohol is dyed with methyl violet."
I wonder if you considered any of these alternatives before arbitrarily deciding it must be cyclohexane. Since you stated the source was from
fermentation for some industrial purpose (non drinkable) I also wonder if you considered they might allow higher concentrations of fusel alcohols than
what they would allow for alcohol produced for consumption.
http://en.wikipedia.org/wiki/Fusel_alcohol
From this: "Excessive concentrations of some alcohols other than ethanol may cause off-flavors, sometimes described as "spicy", "hot", or
"solvent-like". Some beverages, such as rum, whisky (especially Bourbon), incompletely rectified vodka (e.g. Siwucha), and traditional ales and
ciders, are expected to have relatively high concentrations of non-hazardous alcohols as part of their flavor profile. However, in other beverages,
such as Korn, vodka, and lagers, the presence of other alcohols than ethanol is considered a fault.
The compounds involved are chiefly:
2-methyl-1-butanol - sometimes called "active" amyl alcohol
isoamyl alcohol - also known as isopentyl alcohol
isobutyl alcohol - one of the least toxic of the butanols.
n-propyl alcohol
During distillation, fusel alcohols are concentrated in the feints or "tails" at the end of the distillation run. They have an oily consistency, which
is noticeable to the distiller, hence the other name "fusel oil". If desired, these heavier alcohols can be almost completely separated in a reflux
still. Freeze distillation, on the other hand, does not remove fusel alcohols."
Some of these possibilities do give various flavors to the alcohol. While chemistry is not my strong point I mention these alternatives because you
seemed to jump to a conclusion arbitrarily without giving consideration to the points I make here. Or at least you did not mention looking at these
alternatives.
"Science is the belief in the ignorance of the experts" Richard Feynman
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xfusion44
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@OP
Nice experiment, but why not rather make your own ethanol, by fermenting the sugar? This way you would be at least sure, that there's no toxic
denaturants.
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blogfast25
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During Prohibition a test for methanol in various bootleg alcohols was developed by Alexander Gettler (the famous American toxicologist). It relies on
methanol being converted to the acrid formaldehyde (methanal). Here’s a version from a google book:
![](http://oxfordchemserve.com/wp-content/uploads/products_img/methanol_test.png)
[Edited on 28-9-2014 by blogfast25]
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hissingnoise
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Quote: Originally posted by xfusion44 ![](images/xpblue/lastpost.gif) | @OP
Nice experiment, but why not rather make your own ethanol, by fermenting the sugar? This way you would be at least sure, that there's no toxic
denaturants. |
Just ethanol and acetaldehyde, both of which are also toxic . . .
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blogfast25
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Quote: Originally posted by xfusion44 ![](images/xpblue/lastpost.gif) | @OP
Nice experiment, but why not rather make your own ethanol, by fermenting the sugar? This way you would be at least sure, that there's no toxic
denaturants. |
His is a short cut: 2 - 3 weeks of fermentation, then rectifying to 95 % azeotrope.
Acetaldehyde? Huh? During digestion yes, but during fermentation?
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hissingnoise
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Just me assuming some oxidation occurs in the mash . . .
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SimpleChemist-238
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testing for methanol is easy, just heat a copper wire and place it in then smell and see is it smells like formaldehyde. this method was used during
probation in america to test alcohol if it was safe.
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hissingnoise
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Quote: | this method was used during probation in america to test alcohol if it was safe. |
And didn't work particularly well then, by all accounts!
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vmelkon
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Quote: Originally posted by blogfast25 ![](images/xpblue/lastpost.gif) |
Quote: Originally posted by xfusion44 ![](images/xpblue/lastpost.gif) | @OP
Nice experiment, but why not rather make your own ethanol, by fermenting the sugar? This way you would be at least sure, that there's no toxic
denaturants. |
His is a short cut: 2 - 3 weeks of fermentation, then rectifying to 95 % azeotrope.
Acetaldehyde? Huh? During digestion yes, but during fermentation? |
I think that acetyldehyde does form but not 100% sure. Anyway, some aldehyde does form. You can do a aldol condensation by adding
NaOH, letting it dissolve and let it sit for 1 day.
A yellow oily liquid forms and sits at the bottom.
And perhaps products from acyloin condensation?
http://www.perfumerflavorist.com/flavor/research/4236701.htm...
This enzyme was first discovered in bakers yeast. It is responsible for the break down of alcohols into aldehydes and ketones.
http://en.wikipedia.org/wiki/Alcohol_dehydrogenase
As for the ketone part, is it possible that it form propanone, the simplest ketone? I don't know.
So when you make ethanol via the fermentation method, you might get some acetyldehyde and propanone as well.
[Edited on 28-9-2014 by vmelkon]
Signature ==== Is this my youtube page? https://www.youtube.com/watch?v=tA5PYtul5aU
We must attach the electrodes of knowledge to the nipples of ignorance and give a few good jolts.
Yes my evolutionary friends. We are all homos here.
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Oxirane
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If you guys have any neat tricks to remove MEK from ethanol, I'm listening.
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Texium
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Sometimes acetaldehyde will form in small amounts during fermentation, but it is usually undesirable and will only be present in noticeable amounts if
there was something wrong with the fermentation. It adds a green-apple-like flavor and aroma.
Also, acetone, not propanone, is the simplest ketone.
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Amos
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Quote: Originally posted by zts16 ![](images/xpblue/lastpost.gif) | Sometimes acetaldehyde will form in small amounts during fermentation, but it is usually undesirable and will only be present in noticeable amounts if
there was something wrong with the fermentation. It adds a green-apple-like flavor and aroma.
Also, acetone, not propanone, is the simplest ketone. |
Heh.
Acetone IS propanone.
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Texium
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Quote: Originally posted by No Tears Only Dreams Now ![](images/xpblue/lastpost.gif) | Quote: Originally posted by zts16 ![](images/xpblue/lastpost.gif) | Sometimes acetaldehyde will form in small amounts during fermentation, but it is usually undesirable and will only be present in noticeable amounts if
there was something wrong with the fermentation. It adds a green-apple-like flavor and aroma.
Also, acetone, not propanone, is the simplest ketone. |
Heh.
Acetone IS propanone. | ...
(facepalm)
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blogfast25
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Hmmm... going by PBS' 'The Poisoner's Handbook', an excellent documentary about the lives and works of Alexander Gettler and Charles Norris, it
actually worked rather well. Unfortunately some of the authorities had come up with a plan to combat methanol poisoning from bootlegged alcohol by
further increasing the amount of methanol in denaturated ethanol. According to the story the deaths by methanol poisoning shot up proportionally!
Detection of methanol in drinking alcohol with the copper wire method works well because methanal and ethanal smell significantly differently.
[Edited on 28-9-2014 by blogfast25]
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hissingnoise
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Quote: | Unfortunately some of the authorities had come up with a plan to combat methanol poisoning from bootlegged alcohol by further increasing the amount
of methanol in denaturated ethanol. According to the story the deaths by methanol poisoning shot up proportionally! |
Wow ─ 'some authorities'?
The words "bastards" and "complete" fairly spring to mind . . .
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Craftbrewer
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There was nothing arbitrary about choosing cyclohexane. I was n't going to list every possible chemical out there and the reason why it was
eliminated. I only went for those that fit the bill. Remember it has to fit the physical profile of what I have observed, and match the taste profile.
Ethyl acetate was considered (and in low concentrations I would not mind, as it found in wine), BUT it soluble in water and always described as " pear
like" or " very fruity". That does not match what I got.
It was good thought thou. Like cyclohexane, impossible to separate from ethanol/water in distillation. There are a lot of paper on the addition of
cyclohexane as an additive to ethanol to denature it. All are about the safety of it if comsumed.
It forma a tri azetrope, ie ethanol/cyclohexane/water and repeated distillation will actually increase its concentration.
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cyanureeves
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for pete's sake dont drink it and risk blindness or death.i made strong ethanol using aluminum tubing and real corn mash and smelled so wonderful.i
used a steel can as a still and i'm sure it was poisonous but boy was i tempted to drink it.i once drank a substance that had detonium as a bitterent
and it was horrible,i think its called detonium but i'm not sure.
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blogfast25
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Quote: Originally posted by cyanureeves ![](images/xpblue/lastpost.gif) | for pete's sake dont drink it and risk blindness or death.i made strong ethanol using aluminum tubing and real corn mash and smelled so wonderful.i
used a steel can as a still and i'm sure it was poisonous but boy was i tempted to drink it.i once drank a substance that had detonium as a bitterent
and it was horrible,i think its called detonium but i'm not sure. |
What makes you so sure it was poisonous? Decent moonshine, properly distilled is not substantially different from what whiskey makers distil.
I think you meant 'denatonium'.
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Craftbrewer
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Quote: Originally posted by cyanureeves ![](images/xpblue/lastpost.gif) | for pete's sake dont drink it and risk blindness or death.i made strong ethanol using aluminum tubing and real corn mash and smelled so wonderful.i
used a steel can as a still and i'm sure it was poisonous but boy was i tempted to drink it.i once drank a substance that had detonium as a bitterent
and it was horrible,i think its called detonium but i'm not sure. |
too late, made some gin out of it. I made the sacrifice for the sake of science and inebriation and its all good on that front.
More on that latter
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Craftbrewer
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Quote: Originally posted by blogfast25 ![](images/xpblue/lastpost.gif) |
You make some other categorical statements:
”There is no Methanol in it. It is about 95% ethanol, The temperature racing and sitting at a flat 78.5C right thru the distillation”
W/o analysis you can’t be that certain.
”BITTERESS
Utterly no problem here. a simple acid addition, renders the bitterness agent a salt, and it wont distill out.”
There are quite a few bitterants out there. W/o knowing which one is in the bought product how can you be so sure of your statement?
[Edited on 28-9-2014 by blogfast25] |
Think about the experiment and the facts.
Methanol.
1. Diggers insist from numerious sources other than me that there metho is non - toxic to humans
2. The fractional column just did not stop, slow or even glitch at anywhere at Methanols boiling temp, it shot to Ethanols temperature and sat there.
3. In Australia, if its toxic to humans it must be listed. Nothing on the bottle nor spec sheet.
Will test for methanol, BUT no real need. Its not there.
Bitterness agent.
It aint there in the distilled product. Its been drunk by quite a few people (for analysis ) and no-one finds any bitterness what so ever,
It has been removed.
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Craftbrewer
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Quote: Originally posted by xfusion44 ![](images/xpblue/lastpost.gif) | @OP
Nice experiment, but why not rather make your own ethanol, by fermenting the sugar? This way you would be at least sure, that there's no toxic
denaturants. |
But that's the point.
make a sugar mix and distil, and its both VERY time consuming and you have a host of potentially toxic chemicals in the mix. , When you use those
Turbo Yeasts, its even worse.
Methanol, acetone, acetaldehyde, Higher alcohols are all there and in many very noticeable. Do the distil of this toxic mess wrongly, and you
concentrate these, and yes even kill some-one, that happens every year around the world in the thousands.
Least with non-toxic metho, I have at least the potential to make a far safer drink, that is quite pure. If anything is toxic, or at toxic levels,
well the manufacturer by law has to either state it, or make it notable so one doesn't drink it.
So far in general no-one hasn't found any substantial fault with what I have done, BUT ears are open.
As a final clean, I plan to mix and separate liquid carcoal in the mix to be totally anal. Just to get that last little bit.
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Craftbrewer
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Oh, The safety warning ie don't try this at home bit!!!!!
Metho around the world has a wealth of things added to it to denature it. Many are indeed quite toxic (methanol) or cancer causing (benzene). This
experiment I did I picked my mark on the metho that was " more safe" than most.
I wouldn't do this on metho in countries where they add just about anything to the metho.
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