Summary:

By reacting the oxalyl chloride with a mixture of two phenols mixed bis(aryl) oxalates may be synthesized.

Student Handout 2011

Changes to published procedure:

We scaled up the procedure and worked without a drying tube on the reaction flask.

We evaporated the acetone with forced air rather than a rotary evaporator.

We limited the choice of phenol to: 2,3,6-trifluorophenol, 2,4,6-trichlorophenol, 4-nitrophenol, and 2,4-nitrophenol.

The fluorescent indicators we used were rubrene, and 9,10-diphenylanthracene.

We performed a UV scan of the products.

Positive:

+ Chemiluminscence is a cool phenomenon. A nice break from the syntheses of white powders and clear liquids.

Neutral:

± This was the most expensive lab to prepare for us.

± The chemiluminescence does not last long: mix the peroxide into the mixture while in a darkened room.

Negative:

- Most of the combinations (phenol and indicator) proposed in the article don’t chemiluminesce. It seems like a good idea for each student to synthesize at least one product that gives off light.

Inquiry & Extension ideas:

● “Let’s make glowsticks,” one student said.

2011 UV

Student Comments Spring 2008 for Synthesis of Chemiluminescent Esters

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