What are the complete steps of reaction from sodium benzoate and ascorbic acid to benzene? I can't seem to visualize it, and, much less, find anything online regarding the actual steps of the reaction.

Additionally: how does it make use of, say Cu(II) or Fe(III) to complete the reaction? It seems that the reaction can only proceed with these present.


From Benzene production from decarboxylation of benzoic acid in the presence of ascorbic acid and a transition-metal catalyst:

$\ce {Cu^{2+} + H_2Asc \rightarrow Cu^+ + HAsc^.}$

$\ce {Cu^+ + O_2 \rightarrow Cu^{2+} + O_2^-}$

$\ce {2O_2^- + 2H^+ \rightarrow H_2O_2 + O_2}$

$\ce {Cu^+ + H_2O_2 \rightarrow Cu^{2+} + OH^- + OH^.}$

Then the hydroxyl radical reacts with benzonic acid as opposed to benzoate.


The hydroxl radical abstracts hydrogen from the acidic proton of the benzoic acid, producing water and a benzoate radical. This benzoate releases $\ce{CO2}$, producing a $\ce{C6H5}$ phenyl radical, which can abstract a hydrogen from water to regenerate the hydroxyl radical and produce the benzene. https://en.wikipedia.org/wiki/Benzene_in_soft_drinks

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    $\begingroup$ Which hydroxyl radical? Answers should be self-contained. Please edit it to include how to generate the radical or at least reference another answer if it is explained there. $\endgroup$ – Jan Mar 28 '17 at 18:41

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