Comment by chm | Hacker News Reader

Comment by chm | Hacker News Reader

Under atmospheric pressure, ethanol melts at -114C. One way to "powderize" it is to make it into an ester, which in this case would be an ethyl ester[1,2]. Hydrolysis of the ester will occur under acidic conditions which would be brought about by dissolution of carbonic acid. The latter decomposes in acidic conditions to form CO2 and 2 protons. Ester hydrolysis in acidic conditions is reversible. This would explain why they claim their product to contain ~50% ethanol by weight: they need a lot so that the equilibrium concentration is at around 5%.

Assuming my guessing is correct, the innovation here is in the ester. They must have used a "safe, food grade" carboxylic acid to pass certifications. All the powder contains is probably:

- Food dye

- Flavor

- Carbonic acid

- Some ethyl ester

EDIT: A human stomach is also acidic. Ester hydrolysis in alkaline conditions isn't reversible (saponification). If our stomach were alkaline, drinking Palcohol would be very dangerous. The alcohol content in the stomach would skyrocket even if it were low in the drink.

[1]: http://en.wikipedia.org/wiki/Ester [2]: http://www.chemguide.co.uk/organicprops/esters/hydrolysis.ht...

I can't re-edit my post. Here's a related patent[1] which they might own. The ethanol is apparently trapped by cyclodextrins, I was wrong.

[1]:http://www.google.com/patents/US3795747

I'd doubt this because the rate of de-complexation is usually pretty low (which is why it's useful as a mechanism for slowed drug delivery -- the cyclodextrin-complexed compounds move around much more easily than the usually-hydrophobic drug de-complexes from the cyclodextrin).

Edit: reading the application -- this doesn't appear to be cyclodextrins, but some configuration of small-chain length glucose polymers (mentioned 1-20 with an average of 10).

It looks like the powder is made by a physical process. Just as water absorbs into a towel. Ethanol apparently absorbs into dextrin powder and stays as a dry solid.

From the patent:

EXAMPLE II A 150 g. amount of the bulked 5 DE. MOR-REX dextrin of Example I was blended with 250 g. of 90% by weight water) ethanol in a Hobart mixer at speed No. 2 with a wire whisk for 2 minutes. A dry-tothe-touch free flowing powder was obtained that contained 56.2% ethanol and 8.3% moisture. The bulked ethanol containing flowable powder was packaged in air-tight foil envelopes and after 6 months storage had retained its flowability characteristics and its original alcohol content.

EXAMPLE III A teaspoonful (3 g.) of the product of Example II, when added to 10 ml. of water produced a clear, sparkling low-viscosity alcoholic solution with a nonsweet strong alcohol taste.

As a note, that patent expired years ago. (Patents last at most 21 years). That IP is in the public domain now.

Esters don't hydrolyze that quickly under acidic conditions, especially if the carboxylic acid is bulky at all. Also, some esters have CNS effects all by themselves.

I'm pretty sure the gov't would crack down on any form of alcohol that was an ester since it's a new chemical compound and not ethyl alcohol.

That's why I assumed the innovation was in the carboxylic part of the ester. Seems like they sell ethanol adsorbed onto (cyclo)dextrins.

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