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Author: Subject: Brown Ethanol
Meltonium
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[*] posted on 27-12-2016 at 07:12
Brown Ethanol


So I was following a procedure for Doug's Lab where he demonstrated where he got his ethanol from.

https://www.youtube.com/watch?v=rq7a5_tvBPM

He refluxed sodium hydroxide with this product

http://www.homedepot.com/p/Klean-Strip-1-qt-Green-Denatured-...

and that hydrolyzed the ethyl acetate that was present to give the ethanol and water

Anyway, I was bringing the ethanol/NaOH solution to reflux adn stepped out of the room for a moment to fix my morning coffee. When I came back no more than 3 minutes later, the solution looked like this:


IMG_0412.JPG - 1MB


My sodium hydroxide is 99% pure and nothing like this has ever happened when I have used it before. I used the exact same product that Doug used (although in the link the label has changed, but the MSDS are still the same) What could cause this change in color?
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Dr.Bob
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[*] posted on 27-12-2016 at 07:23


Likely the ethyl acetate was deprotonated and had a reaction with itself to form complex hydroxyketones, which can eliminate the hydroxyl and/or further polymerize. There also may have been other compounds in the denatured ethanol. If you distill the final ethanol, that will get rid of most of the crud, and will help remove any remaing ethyl acetate from the product. They pick compounds to denature ethanol based on the fact that they are hard to separate from it. The ATF is not stupid, if they used something easy to denature the ethanol, more people would purify it and drink it, thus avoiding paying taxes to the government, which they are trying to prevent. It may take several steps to get it pure.

It is likely easier to just make your own ethanol in the first place, and then distill it well, if you want pure ethanol, or buy it already pure, as Everclear, if you only need small amounts. Since purifying denatured ethanol is also illegal, there is no real difference between making your own, and purifying store bought stuff. Both are technically illegal, although it is doubtful that you will be bothered unless selling or distributing it. Also, the MSDS may not be current or entirely correct, they might change the formula and fail to update the MSDS quickly. But I doubt that.
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