Neha Patil (Editor)

Diphenyl oxalate

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Related compounds
  
Dimethyl oxalate

Molar mass
  
242.227 g/mol

Formula
  
C14H10O4

Appearance
  
solid

Diphenyl oxalate httpsuploadwikimediaorgwikipediacommonsthu

Hydrogen peroxide and diphenyl oxalate experiment


Diphenyl oxalate (trademark name Cyalume) is a solid ester whose oxidation products are responsible for the chemiluminescence in a glowstick. It can be synthesized by fully esterifying phenol with oxalic acid. The reaction with hydrogen peroxide that diphenyl oxalate undergoes produces phenol and 1,2-dioxetanedione, which excites the dye and releases a photon as it decomposes to carbon dioxide.

Diphenyl oxalate Diphenyl oxalate Wikipedia

The reaction rate is pH dependent, and slightly alkaline conditions achieved by adding a weak base, e.g., sodium salicylate, will produce brighter light. The 2,4,6-trichlorophenol ester of oxalic acid is a solid and thus easier to handle. Furthermore, since trichlorophenolate is the better leaving group, the reaction will proceed faster, again producing brighter light, as compared to the phenol ester.

Diphenyl oxalate 3155166Diphenyl oxalateWikipediaorgDPOcyalumediphenyl

The following colors can be produced by using different dyes:

Diphenyl oxalate Phenyl Oxalate Ester by Emily Bryk on Prezi

Diphenyl oxalate Compound Interest

References

Diphenyl oxalate Wikipedia