Demo This!: Trautz-Schorigin Reaction of Polyphenols in Green Tea

Periodically, I plan to cover a new demonstration from the recent chemical education literature in a feature I’m calling Demo This! Today’s featured demonstration comes from a recent J. Chem. Educ. article, which highlights the use of polyphenols in green tea for the luminescent Trautz-Schorigin reaction.

Background

Pyrogallol, or what we might call 1,2,3-trihydroxybenzene, undergoes an interesting set of transformations under oxidative conditions. In the presence of water, formaldehyde, base, and hydrogen peroxide, pyrogallol is oxidized and excited singlet oxygen is produced. Relaxation of singlet oxygen to its ground state produces red luminescence.

The Trautz-Schorigin Reaction: see if you can draw a mechanism for this beast!

The Trautz-Schorigin Reaction: see if you can draw a mechanism for this beast!

A quick literature search has revealed that this reaction has been understudied (or at least underpublished) over the years. See if you can draw a mechanism accounting for all the products! All manner of oxygen-containing species may be present under these harsh conditions, including superoxide anion and hydroperoxide anion.

This reaction can be slowed or prevented by treatment with boric acid (forming cyclic borate esters, which are resistant to oxidation) or by treatment with ascorbic acid, which can reduce the 1,2-keto intermediate back to pyrogallol and (in a separate reaction) react with singlet oxygen. Considering these quenching reagents, this demonstration has all the trappings of a “green,” easy-to-prepare experiment.

Experiment

This demo can be carried out either with the parent pyrogallol or with polyphenols found in green tea. Either way, set up is straightforward, and the article claims that the entire kit and kaboodle takes less than one hour. Assuming that a tea bag holds about 2 grams of tea leaves, infusing for ~3 minutes in 200 mL of hot water is long enough to push a sufficient quantity of polyphenols into the water. Paraformaldehyde and sodium carbonate are then added to the hot tea with stirring, and the solution is allowed to cool to room temperature in a water bath. The pH of the solution is checked using pH paper or indicator before adding hydrogen peroxide (it should be ~11). 50 mL of the pH 11 solution are transferred to an empty beaker, and the lights are killed. Finally, 50 mL of dilute (3%) hydrogen peroxide are added. Luminescence should be instantaneous, and lasts for 5-10 seconds.

Ascorbic acid completely shuts down the reaction, while boric acid only slows it down. These quenching reagents should be added just before the lights are killed, right before the addition of hydrogen peroxide.

Source

Panzarasa, G.; Sparnassi, K. J. Chem. Educ. 2012ASAP. doi: 10.1021/ed200810c

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