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Chemosynthesis
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Quote: Originally posted by Craftbrewer  |
You read my mind, as its boiling point makes it dead easy to separate via distillation. Wasn't quite sure how to do this as to oxidise it, one add O2
but evaporates it
Oh shit, brain fart
People are now describing the flavour now after the olive oil addition and shaking (as I stated it before ) as pepermint and solvent like.
Guess what the descriptor is for cyclohexanone is, exactly that. Now I wonder if by shaking the ethanol, with the oil, I have oxidised the cyclohexane
to cyclohexanone.
Gee one more piece of the puzzle in place |
I would be kind of surprised if you oxidized the cyclohexane into cyclohexanone in olive oil. I would suggest chlorination, SN2 reaction with a
hydroxide, then oxidation with permanganate. To be fair, you could perform a Lucas test on the secondary alcohol and convince me. The name eluded me
as it is highly antiquated nowadays, but it is fairly simple with HCl and ZnCl2.
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Craftbrewer
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>>>>>I would be kind of surprised if you oxidized the cyclohexane into cyclohexanone in olive oil. <<<<<
Minor clarification as I worded it badly. What I meant to say I oxidized some cyclohexane into cyclohexanone when I added the olive oil and shook it.
The oxidization didn't occur in the oil, it occurred in the ethanol/water solution.
Just saying and putting it out there where the peppermint oil smell that has suddenly appeared came from.
Further again, I have two people repeating this experiment to see if the results are the same. I have made sure they DONT shake the ethanol water
mixture too much.
Both report the cloudiness then clearness after olive oil addition. Still to do the blind taste test to see what they have.
[Edited on 30-9-2014 by Craftbrewer]
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Chemosynthesis
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So, please correct me if I am wrong, your current working hypothesis is that you oxidized the suspected cyclohexane into cyclohexanone from
atmospheric oxygen? If not, where do you believe the oxygen would come from?
This would seem very unusual to me. I started looking up NIST thermodynamic values, but decided not to bother, as the activation energies would
confound even favorable exothermic values. The reasons I would be skeptical of a cyclohexane oxidation are as follows:
1. The proposed reaction would be entropically unfavorable in the balanced equation. You start with molecular oxygen and cyclohexane, and end with
cyclohexanone. As you didn't see any hydrogen loss, I would suggest temporarily assuming for the sake of argument it combined wifh something else.
That is a net loss in entropy, and so unlikely in ambient conditions.
2. The activation energy must be high. If you add potassium permanganate to cyclohexane, you do not see green indicative of the manganate ion as you
do upon addition to either cyclohexene or cyclohexanol. Permanganate is a strong oxidizer, and would be expected to react much more readily than
oxygen in ambient conditions. Instead, intermediate steps are necessary to achieve this reaction with permanganate.
So if you were to keep this hypothesis, I would be under the impression it would only seem reasonable if you believed an unknown catalyst of some sort
were also in your alcohol, which would be worrisome from a health perspective.
Basing chemical analysis off of taste or olfaction (which influences taste), is not a definitive measure, as roughly 25% of individuals in the U.S.
alone over age 53 appear to be olfactorally impaired (Murphy C, Schubert CR, Cruickshanks KJ, Klein BE, Klein R, Nondahl DM. Prevalence of olfactory
impairment in older adults. JAMA. Nov 13 2002;288(18):2307-12.).
Transient olfactory and gustatory disorders can occur with infection, seasonal allergies, aging, pharmaceutical use, neurological damage, nasal
polyps, etc. A wide range of dynamic factors, including hormones, affect the sensation of taste through cellular signaling, and thus it is not the
best presumptive test for a substance. I would be very interested in seeing some physical data, a qualitative test for the presence of a functional
group you expect, a negative control, and if you want to go above and beyond, perhaps a chemical reaction to a derivative of your presumed product,
then a repeat of physical and qualitative testing, if possible. In the absence of spectroscopic/metric testing, this would essentially convince me
beyond doubt.
If your testing doesn't support the current hypothesis, perhaps a test for an ester could be done. The only appropriate method that comes to mind
would be to hydrolize to a carboxylic acid and use a carbonate/bicarbonate salt to check for liberation of carbon dioxide in an acid/base reaction.
[Edited on 30-9-2014 by Chemosynthesis]
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forgottenpassword
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Obviously claims of cyclohexane oxidation are a nonsense, but the method of extracting it (or any alkane) with oil is perfectly reasonable.
Despite what the label says, I would imagine that anything called "metho" and sold as "methylated" spirits does actually contain methanol/methyl
alcohol.
You seem to have taken the manufacturer's claims that it is non toxic to USE to mean that it is non toxic to DRINK. Unless you made it plain that you
were speaking of drinking it, I think that it is safe to assume that you were talking at cross purposes.
If you intend to drink a lot of this, you should definitely get it professionally analysed, or at least test it for methanol as recommended by others.
I am entirely confused by your claims of "very exothermic" extraction of cyclohexane by oil. It makes no sense whatsoever. Nor does your claim of
oxidising (supposedly) cyclohexane to cyclohexanone.
Please describe the "VERY exothermic" reaction that you observed when you added oil. How hot did it get? Your statement is quite unbelievable. It
seems to be a blatant lie.
[Edited on 30-9-2014 by forgottenpassword]
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Chemosynthesis
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I am just trying to show him how I view the proposal as I understand it since he appeared to dispute
earlier scepticism displayed by both IrC and Blogfast25, and gave us a run through of his thought processes in the original post. The latter suggests
to me that he might be open to socratic discussion rather than my usual approach. Normally I would post all about bad lab practice and toxicities,
especially when sharing substances of unknown purity or identity with others, but it appears that ship has sailed.
| Quote: |
You seem to have taken the manufacturer's claims that it is non toxic to USE to mean that it is non toxic to DRINK. Unless you made it plain that you
were speaking of drinking it, I think that it is safe to assume that you were talking at cross purposes.
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This is an excellent point. I am not Australian, and generally just ignore foreign legalities as they have
no bearing on me, but I suspect craft brewer is referencing the Work Health and Safety (WHS) Regulations, which I just glanced over. If this is the
case, they do appear to be describing only acute toxicities or hazards risked by exposure to chemicals or products within the scope of intended use
only. Much could be said about that from a toxicological perspective.
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blogfast25
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Nowhere in the article does it state MASH. It is in fact vague and very short on details. As always you report very sloppily, then claim it's 'fact'.
Nor does it constitute the kind of pandemic you were painting in broad brush strokes. If 'thousands' were affected by it, it would be in the news
constantly and the forums would be buzzing with it. Turbo yeast would be banned from use in home brewing.
I will run the cyclohexane tests later on.
I find it rather funny that someone claims to have found cyclohexane w/o even possessing a reference sample of that material.
[Edited on 30-9-2014 by blogfast25]
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blogfast25
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| Quote: Originally posted by Craftbrewer |
Guess what the descriptor is for cyclohexanone is, exactly that. Now I wonder if by shaking the ethanol, with the oil, I have oxidised the cyclohexane
to cyclohexanone.
Gee one more piece of the puzzle in place |
Gee-whiz, how much LOWER can you lay bar for the burden of proof, huh?
Do you know how hard it is to oxidise cyclohexane to cyclohexanone?
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Little_Ghost_again
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Hi
I have a copy of what will be published, now I know technically you could argue it isnt published yet therefore its not valid...... To the best of my
knowledge it has been reviewed and awaiting printing deadlines.
My dad has circled the bits I can use and scribbled over the bits I cant (not yet anyway). Its a fair bit of typing so I will try and do it later. If
you have questions after your gonna have to email my dad as i dont get 3/4 of what is written  .
But in simple terms what I can work is, Turbo yeast will only convert upto 13.4% ETHANOL with SUCROSE used. After that it gets funny and starts making
a whole list of other things. This is not the case however with different sugars, I will post those figures later and as soon as its published I will
come back and link to the journal.
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blogfast25
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Thanks, Little_Ghost.
| Quote: Originally posted by Chemosynthesis | This would seem very unusual to me. I started looking up NIST thermodynamic values, but decided not to bother, as the activation energies would
confound even favorable exothermic values. The reasons I would be skeptical of a cyclohexane oxidation are as follows:
1. The proposed reaction would be entropically unfavorable in the balanced equation. You start with molecular oxygen and cyclohexane, and end with
cyclohexanone. As you didn't see any hydrogen loss, I would suggest temporarily assuming for the sake of argument it combined wifh something else.
That is a net loss in entropy, and so unlikely in ambient conditions.
2. The activation energy must be high. If you add potassium permanganate to cyclohexane, you do not see green indicative of the manganate ion as you
do upon addition to either cyclohexene or cyclohexanol. Permanganate is a strong oxidizer, and would be expected to react much more readily than
oxygen in ambient conditions. Instead, intermediate steps are necessary to achieve this reaction with permanganate.
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The oxidation of cyclohexane to cyclohexanone is likely to be very exothermic, see for instance propane to propanone, (NIST values):
Propane ΔH<sub>F, liquid</sub><sup>0</sup> = - 119.8 kJ/mol
Propanone ΔH<sub>F, liquid</sub><sup>0</sup> = - 249.4 kJ/mol
But the activation energy is prohibitive. Higher temperature, a much stronger oxidiser (than oxygen) and a specific catalyst might do it.
[Edited on 30-9-2014 by blogfast25]
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Chemosynthesis
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Agreed; thanks, LittleGhost!
| Quote: Originally posted by blogfast25 |
The oxidation of cyclohexane to cyclohexanone is likely to be very exothermic, see for instance propane to propanone, (NIST values):
Propane ΔH<sub>F, liquid</sub><sup>0</sup> = - 119.8 kJ/mol
Propanone ΔH<sub>F, liquid</sub><sup>0</sup> = - 249.4 kJ/mol
But the activation energy is prohibitive. Higher temperature, a much stronger oxidiser (than oxygen) and a specific catalyst might do it.
[Edited on 30-9-2014 by blogfast25] |
Yes, I was hoping to convey that with my post. I believe I had hit every point. The requirement for an unknown and contaminant catalyst alone was
meant to cause hesitation at the consumption of uncharacterized product. (edit: assuming an actual oxidation as his working hypothesis, solely for
the sake of argument.)
I was going to get into Hess's Law for craft brewer to see how I think about reactions, enthalpy being where I tend to start, but thought better of it
as it may have just been confusing and was around 4am in my region at the time. Explaining catalysis without getting into transition states, comparing
them to the intermediates in the reaction scheme I proposed, and then confounding the exothermic mixing (likely not reaction) in terms of enthalpies
of mixing was not something I wanted to bother with seeing as how I haven't had a response yet and don't want to seem too pedantic.
Also, I felt posting a half reaction as cyclohexane to cyclohexanone might not be giving craft brewer enough credit, as one could theoretically argue
the other half of the equation (where did the oxygen come from?) may offset the negative enthalpy, making the sum endothermic. How that would be
reasonable would obviously be debatable, but it is possible, and so so I chose to avoid it due to its irrelevance. And yes, I know arguing such would
be thermodynamically counterproductive, but I want to see how craft brewer views the situation thermodynamically, and then kinetically in light of
permanganate, a much stronger oxidizer as you noted, not oxidizing cyclohexane.
Thermodynically, this is also why I was careful to try to state that craft brewer did not note the evolution of hydrogen gas, as this could be used to
argue zero sum entropy, which could appear more favorable than decreasing entropy under standard lab conditions (lack of pressure).
Again, I am not trying to suggest this is reasonable, but I think we both know you can make the math say whatever you want in the absence of data. The
last thing I want to is have someone infer that I find it reasonable to succuss cyclohexane with enough force to cause spontaneous atmospheric
oxidation and the byproduct water, which would be close to zero sum entropically, cloud up the oil due to differences in refraction indices, be
exothermic, and yet still so fanciful as to make me regret typing it right now.
[Edited on 30-9-2014 by Chemosynthesis]
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blogfast25
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Thanks Chemosynthesis, super thorough.
Ok, here’s my experiment. In four clean test tubes was loaded:
1. 2 ml cyclohexane 99.9 %
2. 2 ml pure ethanol (a Sigma Aldrich standard material)
3. and 4. 2 ml of freshly bought extra virgin olive oil each
All tubes were cling filmed and immersed in a cup of RT water for 30 minutes for temperature equalisation. The temperature read 22.9 C, just prior to
carrying out the experiments.
Experiment 1:
The contents of 1. was added to 3. with gentle stirring using the thermo couple as stirring rod. The cyclohexane dissolved in the olive oil
effortlessly. The end temperature was 22.2 C, so no exotherm. As I expected the dissolution of cyclohexane in olive oil is purely entropy driven, not
enthalpy driven.
Experiment 2:
To 2. were added 5 drops (about 0.25 ml) of cyclohexane 99.9 % and the mixture gently stirred. No exotherm was observed.
That mixture was added to 4. This of course did not form one phase: the alcohol sat neatly on top. Intense stirring caused a suspension of the two
liquids, presumably with transfer of the cyclohexane into the olive oil phase. The final temperature was 20.3 C, so no exotherm either.
After a few minutes the phases separated out very cleanly.
General view at start:
Cyclohexane 99.9 %:
Craftbrewer needs to go back to his exotherm to confirm that it is actually there.
[Edited on 30-9-2014 by blogfast25]
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Craftbrewer
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>>>>Craftbrewer needs to go back to his exotherm to confirm that it is actually there.<<<<
Mate
thanks for doing the experiment. Really appreciate it. The exothermic observation was just that, an observation without an actual thermometer. The
solution felt real warm after the addition, BUT obviously that must be a mistake, even drunken fact, who knows.
Good to see the oil oil actually does what its susposed to by the way, so overall everything is still very much on track. Just eliminated one varable.
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Craftbrewer
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>>>>>>So, please correct me if I am wrong, your current working hypothesis is that you oxidized the suspected cyclohexane into
cyclohexanone from atmospheric oxygen? If not, where do you believe the oxygen would come from?<<<<
This is what I am throwing out there for understanding. Orginally the ethanol/x/water mixture did BOT HAVE a peppermint smell (as described by
others). More sweet/ slighty fruity/solvent.
The addition of oil oil, dilution with water, shaking and a few days and a distinct peppermint smell is there. No mistake.
Further that smell is now only in the oilive oil, NOT in the ethanol mix when the olive oil is decanted off. Whats left is a very clean ethanol smell.
Now that's where this ends as what I know, Speculation starts after this and all the stuff about cyclohexane, as its the candidate at present that "
fits the bill".
>>>Basing chemical analysis off of taste or olfaction (which influences taste), is not a definitive measure, as roughly 25% of individuals
in the U.S. alone over age 53 appear to be olfactorally impaired (Murphy C, Schubert CR, Cruickshanks KJ, Klein BE, Klein R, Nondahl DM. Prevalence of
olfactory impairment in older adults. JAMA. Nov 13 2002;288(18):2307-12.).<<<<
As a brewer smell and taste tests are VERY important, if not critical in out brewing process. The people doing the testing are BJCP trained tasters,
they know their flavours. That said, I know what you mean. I am supersensitive to diacetyl, yet totally blind to many phenols
I go by the masses
>>>> If your testing doesn't support the current hypothesis, perhaps a test for an ester could be done. The only appropriate method that
comes to mind would be to hydrolize to a carboxylic acid and use a carbonate/bicarbonate salt to check for liberation of carbon dioxide in an
acid/base reaction.<<<
Will do, in fact I prefer an ester, solely on the drinking safely angle. I haven't ruled it out by the way, just need to fully explore the cyclohexane
angle first, ALL THE POSSIBILITIES, why it can or cant be it, and so on, then onto esters.
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Craftbrewer
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>>>>Obviously claims of cyclohexane oxidation are a nonsense,<<<<
Just throwing it out there as a possibility. Its looking shaky
>>>.
Despite what the label says, I would imagine that anything called "metho" and sold as "methylated" spirits does actually contain methanol/methyl
alcohol.<<<
That I disagree, Yes in the past it was methanol, then contained methanol, and that's whats the public expect. Now the name methylated spirits is such
a common name, the public wont where a name change, and companies wont want to lose market share. So they can change the denaturant, even remove
methanol, and will still call it Methylated spirits.
I am extremely confident there is no methanol in it.
(ne says as he goes blind, reals over and dies)
>>>You seem to have taken the manufacturer's claims that it is non toxic to USE to mean that it is non toxic to DRINK. Unless you made it
plain that you were speaking of drinking it, I think that it is safe to assume that you were talking at cross purposes.<<<
The James Hardy experience over here as sent companies in a panic (basically selling asbestos products, knowing its in their products, even warning
people). They got sued to the hilt. At least in the western countries, companies are moving to non toxic metho, as they know the drunks, bums,
suceptable (and mad idiots) are drinking it.
If a company knows this, they must take ALL precautions in what they put in it. The burden of proof has changed.
>>>> Please describe the "VERY exothermic" reaction that you observed when you added oil. How hot did it get? Your statement is quite
unbelievable. It seems to be a blatant lie.<<<<
I'll wear that one on the chin. Logic says it cant be exothermic, do know why I thought this. Should have done more before blurting that one out.
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Craftbrewer
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>>>>Gee-whiz, how much LOWER can you lay bar for the burden of proof, huh?
Do you know how hard it is to oxidise cyclohexane to cyclohexanone? <<<
I only threw it out there as a possibility.
I have a peppery /solvent smell I cant explain, and its now only in the olive oil. It made sense at the time. Good idea, BUT as stated looks a little
shaky.
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Craftbrewer
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>>>>But in simple terms what I can work is, Turbo yeast will only convert upto 13.4% ETHANOL with SUCROSE used. After that it gets funny
and starts making a whole list of other things. This is not the case however with different sugars, I will post those figures later and as soon as its
published I will come back and link to the journal.<<<<
Gee, back to wine yeast, or even yeast used for sake. I can push them to 15-16%.
As for other things, I know lots of methanol gets produced, and even more acetone too. I I personally don't like using it, so keen for the results
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Craftbrewer
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>>>Nowhere in the article does it state MASH. It is in fact vague and very short on details. As always you report very sloppily, then claim
it's 'fact'.<<<<
You wanted proof that its occurring, I give it. Wont go any further. These guys were using Turbo yeast by the way. They kept the first running chock
full of methanol. What happened as they got drunk, they forgot which bottle they kept the first running and drunk it. That's the story.
>>>Nor does it constitute the kind of pandemic you were painting in broad brush strokes. If 'thousands' were affected by it, it would be in
the news constantly and the forums would be buzzing with it. Turbo yeast would be banned from use in home brewing.<<<
There is no pandemic, Russian die by the thousands thru poor distillation, And of course people are dropping dead in Indonesia from poor distillation,
including a healthy dose of tourists. Including Aussies. Turbo yeast is safe if you do it properly. And remember these buggers should not be
distilling, so the yeast aint in fault persay.
And yes, plenty of media when weddings in India end up with half the guests dies from methanol poisoning.
Its spread soooo thinly around the world it goes under the radar, and acceptable.
Like gun killings, and road death, all normal, nothing to see here
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hyfalcon
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Temperature control essentially eliminates any problem with methanol. The BP of methanol and ethanol are so far apart that there shouldn't be any
contamination as long as proper boiling points are used and cuts made when they change.
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blogfast25
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| Quote: Originally posted by Craftbrewer | Gee, back to wine yeast, or even yeast used for sake. I can push them to 15-16%.
As for other things, I know lots of methanol gets produced, and even more acetone too. I I personally don't like using it, so keen for the results
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You measured the ABV? If so, how?
Same with methanol/acetone: how did you ascertain/measure this?
| Quote: Originally posted by Craftbrewer | You wanted proof that its occurring, I give it. Wont go any further. These guys were using Turbo yeast by the way. They kept the first running chock
full of methanol. What happened as they got drunk, they forgot which bottle they kept the first running and drunk it. That's the story.
There is no pandemic, Russian die by the thousands thru poor distillation, And of course people are dropping dead in Indonesia from poor distillation,
including a healthy dose of tourists. Including Aussies. Turbo yeast is safe if you do it properly. And remember these buggers should not be
distilling, so the yeast aint in fault persay.
And yes, plenty of media when weddings in India end up with half the guests dies from methanol poisoning.
Its spread soooo thinly around the world it goes under the radar, and acceptable.
Like gun killings, and road death, all normal, nothing to see here
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The article says nothing about Turbo yeast.
The rest is more of your trademark ‘I know’. If it's under the radar, how come you know about it?
And I have pixies in the back of my garden, because ‘I know’.
I think you experiment was quite interesting and some of your reasoning sound. But your evidence base is flimsy and you're all too happy to accept
that. Not scientific...
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Craftbrewer
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>>>>The article says nothing about Turbo yeast.
The rest is more of your trademark ‘I know’. If it's under the radar, how come you know about it <<<<<
Well when your in the industry you take an interest in these things, so a quick talk to the my police contact got me the information.
The Govt wanted to scare the public with all the home distillation going on, so the media release was tailored for that purpose. And reporters
nowadays are on a 24 hour cycle, so no investigation, just print the police statement.
>>>> And I have pixies in the back of my garden, because ‘I know’.<<<
Nah, The "salties" have eaten all mine, its a shame really, a little bit of pixie dust would have saved me in my ethanol/water distillate. It would
have cleared it nicely
>>>>>I think you experiment was quite interesting and some of your reasoning sound. But your evidence base is flimsy and you're all too
happy to accept that. Not scientific...<<<<<
Oh agree its not totally scientific. Its on the first step thou. Observation of what goes on, form an opinion of what might be going on, test with
further observations, That's as far as I have got.
Haven't form the theory or hypothesis yet. Still exploring the observations. Haven't tested repeatibity, nor even try to disprove any hypothesis, (how
can one if I haven't nailed it down yet.
Then again I could adopt a simple budhist approach - there are things in life that never can be explained, so don't worry about them.
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Craftbrewer
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Blogfast 25
There is one experiment that you haven't carried out - it would definitely rule out a number of things
1. Mix a drop of cyclohexane in a few ml of ethanol and mix. It should dissolve totally
2. Add water of say equal volume. That should make the mixture cloudy, as the cyclohexane goes out of solution
3. Add a couple of drops of olive oil and mix.
Measure temperature and more smell after a day. Any sign of temperature rise, OR peppermint/solvent smell.
Worth a go
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Craftbrewer
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And another update, as the experiment is repeated by others.
The significance of the peppermint/solvent aroma may be due to the brand of Olive oil used. Sampled another two similar methods, and definitely no
peppermint/solvent smell.
So maybe something in the olive oil, depending on brand thus composition of aromatics, maybe causing that smell, especially mixing with our mystery x
compound.
On the otherside, again all report the same add water cloudiness, add oil, clears. Spirit very clean tasting.
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Craftbrewer
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Separate post on Turbo Yeast and my Carbon treatment.
Got my Turbo Carbon, basically super fine carbon added to a Turbo yeast wash during fermentation. Read thru the propaganda, and basically they state
its to mop up all the byproducts of specifically turbo yeast fermentation.
Make that what you like BUT!!!!!!!!!!
adding a small amount to the ethanol/water mix as a final cleaning up of the distillate. As its quite clean wont need much. Should be interesting
especially as it also contains sulphites-
will be fun to taste test
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blogfast25
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| Quote: Originally posted by Craftbrewer | Blogfast 25
There is one experiment that you haven't carried out - it would definitely rule out a number of things
1. Mix a drop of cyclohexane in a few ml of ethanol and mix. It should dissolve totally
2. Add water of say equal volume. That should make the mixture cloudy, as the cyclohexane goes out of solution
3. Add a couple of drops of olive oil and mix.
Measure temperature and more smell after a day. Any sign of temperature rise, OR peppermint/solvent smell.
Worth a go |
I'll definitely do that, probably tonight.
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Little_Ghost_again
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Looking on ebay one company in particular has all kinds of turbo yeast and makes a lot of claims.
They recommend the use of charcoal, from the little I know I would think when you measure by hydrometer then yes you get a high alcohol reading, but I
wonder how much of that is actually ETHANOL?
I would really like to set up some experiments with different yeasts and sugars, maybe if I can talk my dad into taking the resulting samples into
work and running them through the CG and other stuff there it might show whats in them.
Alchotech mention Dextrose, but I still doubt that would give great results. I will keep using bakers yeast  , yes lower production of Ethanol but it does some benefits .
The other thing that makes a difference is the water, low oxygen content is good, purging the vessel with CO2 (2 days before adding yeast) also gives
better results.
I cant yet quantify better (not allowed yet). I was going to post what I could, but its going to leave more questions than answers. So probably better
I wait until its actually printed then I can link you to a full paper. Only 1/3 of the paper relates to yeast though.
The other paper I want to link to is more about yeast, I am waiting for the ok to post a link. Last thing I want to do is get my dad into trouble,
they publish loads of papers and some they release free of charge. Other papers are from research that they are paid to do by others, apparently these
papers need permission to be released.
You guys will know way more about how publishing papers work than me! I assumed once it was reviewed etc then the people that wrote it could do what
they want with it, but I am told this is not always so!
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