ORGLIST: Conditions for the conversion of phenol into benzene (non-chemist's question)

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From: Joshua McGee (joshua$##$mcgees.org)
Date: Mon Oct 20 2008 - 02:12:24 EDT


I am not an organic chemist. I do not have a firm command of the
vocabulary, and my question, in three parts, is likely to be imprecise and
badly-worded. I appreciate your tolerance of my intrusion.

For the context in which my question arose, I was having a discussion with
another non-chemist about the production of scotch whisky. In some cases,
grain is dried over a peat fire. This impregnates the grain with phenolic
compounds, including simple phenol, which is retained in the final product
following distillation.

Yes, the resulting product is consumed intentionally by some people. :^)

The first part of my question is to establish under what conditions simple
phenol can be converted into benzene. If I understand correctly, this would
entail the replacement of a hydroxyl group with a hydrogen atom.

I understand that the reverse conversion -- benzene to phenol -- can be
accelerated by (or is impossible without, I don't know) copper-containing
compounds. The conditions of the distillation under discussion involve the
presence of ethanol and other yeast metabolites (including other alcohols),
various organic compounds, elemental copper from the still, and the
application of direct heat. Thus, the second part of my question (which
may, to answer, require more information than I have provided) is whether
the conversion of phenol to benzene would be likely to arise accidentally in
the process of commercial whisky distillation.

Finally, I am wondering the likelihood of benzene surviving into the final
bottled product, which is the "middle cut" (the period of the still run
including the portion containing the highest percentage of ethanol) diluted
with water.

I do not have access to an adequate textbook. I have been unsuccessful in
answering this question through search engine queries, likely because I am
not providing the correct keywords. I have read the charter and believe
that my question is within the bounds of discussion.

Thank you,

Joshua McGee
http://www.mcgees.org


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