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Author: Subject: How do you tell methanol from ethanol?
Vogelzang
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[*] posted on 22-8-2009 at 15:01


Alcoholic beverage Russian roulette. If its methanol you go blind. If its ethanol you just get drunk. No, better not. You might not get your sight back. How about a refractometer?
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[*] posted on 23-8-2009 at 00:58


There is another method, esterification of the alcohol with 3,5-dinitrobenzoic acid, and then measuring the melting temperature, if the sample would be pure, the melting interval should be sharp, another way would be making a TLC analysis with this sample.
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[*] posted on 23-8-2009 at 01:43


Quote:
But here is a better, more beautiful one: boric acid. Methanol burns green with a bit of boric acid mixed in it, while ethanol does not.


uhh.. are you sure? I'd seriously double check that.

also... why wouldn't ethanol reduce copper as does methanol? I'm pretty sure it does...

[Edited on 23-8-2009 by kclo4]




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JohnWW
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[*] posted on 23-8-2009 at 01:51


What about doing an NMR analysis on it? CH3OH only has the alcoholic H on OH plus the three CH3 hydrogens, while ethanol also has a pair of -CH2- hydrogens, which would be distinct.
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[*] posted on 23-8-2009 at 05:10


Quote: Originally posted by JohnWW  
What about doing an NMR analysis on it? CH3OH only has the alcoholic H on OH plus the three CH3 hydrogens, while ethanol also has a pair of -CH2- hydrogens, which would be distinct.


An elegant solution that only requires someone without so much as a heating mantle, to have access to an NMR spectrometer.
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[*] posted on 23-8-2009 at 07:21


If one has a reasonable sensitive set of scales, the difference in solubility of NH4NO3 in the two alcohols could be exploited. Take say 50 cc of each in two separate small flasks or bottles, and add sufficient NH4NO3 to each so that some of the nitrate remains undissolved. Let it sit overnight, if all the nitrate dissolves add some more and let sit for a few more hours. The carefully pour off the clear liquid in order to get 25 cc, pour into a tared beaker or small jar, allow to evaporate, and weigh. MeOH will dissolve 2 to 3 times as much NH4NO3 as EtOH in the 90% to 100% range. 100 g 100% MeOH dissolves 14.6 g NH4NO3 @ 14 C and 16.3 g @ 18,5 C and 17.1 g @ 20.5

Otherwise the methods for those not owning their own NMR, FTIR, mass spec, or even GC, would seem to be

1) boiling point, done in a test tube with the thermometer suspended in the vapour such that some condensate forms on the stem above the bulb.

2) iodoform test, MeOH will not give iodoform while ethanol and isopropanol will.

3) smelling, although many people can not distinguish the two alcohols.

4) density, although this does take a better set of scales and some care in measuring volumes given the small density differences.

5) giving some to a test animal, in amounts small enough that EtOH shouldn't kill it. Using one's neighbors or friends as the test animal may cause inconvenience, as might larger pets especially from your own household. Stick to small rodents and don't talk about it to others.

6) Evaporation of a drop might do it, although when I tried this with 5 side by side comparisons only in one case was the MeOH clearly faster to evaporate. Perhaps do the test on a bulky block of metal so that evaporative cooling doesn't slow down further evaporation of the drops.

Making the standard derivatives works, except that most people don't have the needed reagents at home. It's as easy to take the BP of the alcohol as of an ester, so making an ester and measuring its BP is just extra work.

Oxidising a ml or two with hot acid dichromate and noting the odor might do, as both the corresponding aldehydes and carboxylic acids are fairly distinct in their smells.



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[*] posted on 23-8-2009 at 12:03


Yes the boiling point would be suitable, but the "smell test", for sure one wouldn't distinguish if it was like 2% impurity of methanol in ethanol?
But nontheless maybe if you make the derivative and then have the bp of the liquid and also the bp of the derivative one can make a better quess of the purity.

Concerning the TLC, here is the mobile phase, if someone is interested 8:10:1 cyclohexane:toluene:ethyl acetate.
Visualisation: spray with rhodamine B or UV 254nm.
Yes not very practical indeed.
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[*] posted on 23-8-2009 at 20:57


Ah, but the thread started with two unlabeled bottles, one EtOH and one MeOh, both of lab grade. A side-by-side comparison should be able to distinguish pre MeOH from EtOH with some MeOH denaturant - provide we're talking the oxidiser + smell test.

The possibilty of some MeOH in the EtOH reduces the value of some derivatives, as those of the two alcohols can be *%$%^ hard to separate or purify; although TLC should do so. But you'd need kwon samples of the 2 alcohols to compare RF values of the unknow, and getting known samples of the alcohols is what started this thread.

The boiling point could be done simply by banding two test tubes together and adding one of the unknown samples in each. Place in water bather a bit below the BP of MeOH and fairly slowly raise the bath temperature. The MeOH will start boiling before the EtOH, even a few percent of MeOH in the EtOH shouldn't be too hard to tell from pure MeOH. Raising the temperature above the BP of MeOH wil boil that tube dry while only reducing the volume of the EtOIH to a slight extent.




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JohnWW
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[*] posted on 24-8-2009 at 13:14


Quote: Originally posted by JohnWW  
What about doing an NMR analysis on it? CH3OH only has the alcoholic H on OH plus the three CH3 hydrogens, while ethanol also has a pair of -CH2- hydrogens, which would be distinct.
In addition, the IR spectrum of CH3OH should be distinct from that of CH3CH2OH, as regards both "stretching" frequencies because ethanol has a C-C bond which methanol does not have, and "bending" frequencies because ethanol has a C-C-O bending mode which methanol does not have.

See my upload of the Sigma-Aldrich IR and NMR spectral data and related materials in References, which would certainly include the spectra of both alcohols.

[Edited on 25-8-09 by JohnWW]
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[*] posted on 2-9-2009 at 14:58


Methanol smells similar to acetone but not as floral and much less pungent.
Ethanol smells the same as any liquour.

Wet your pinky and with that your lips at the corner of your mouth. If it feels
and tastes much as liquour then its ethanol. If you feel a burning sensation
that lasts even after you wash , then its methanol.

Of course you must be certain that what you test is pure
and is not something else possibly carcinogenic.

.
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[*] posted on 9-9-2009 at 20:01


Quote: Originally posted by bfesser  
A drop of each on the bench. MeOH should evaporate faster.


I like this idea, simple and smart. Whichever one evaporates slower take a quick, short sniff to make sure it's ethanol.

Another idea might be to try and dissolve table salt in both. More salt should dissolve in methanol.

[Edited on 10-9-2009 by HydroCarbon]
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[*] posted on 9-9-2009 at 20:53


Hah! Simply take a little NaBH4, and dissolve it in your solvent. NaBH4 is fairly stable in Ethanol. Not so in Methanol. It will slowly decompose, liberating bubbles of Hydrogen gas.
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[*] posted on 10-9-2009 at 10:32


So far as evaporation tests go, might as well use your palm or the back of your hand. This mostly gets around the problem of evaporative cooling bringing the evaporation times closer together, and on top of that the methanol should feel colder. In fact using a q-tip or the like to swab some on (rather than just dripping a little drop) would probably give you a better feel for the difference in cooling.
If you're confident they're pure you could also look at the difference in conductivity. Both are effectively insulators, but ethanol has a higher dielectric constant as I recall. Wouldn't take much in the way of dissolved salts to make that a useless measure though.
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