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Diphenyl oxalate

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Diphenyl oxalate
Skeletal formula of diphenyl oxalate
Ball-and-stick model of the diphenyl oxalate molecule
Names
Preferred IUPAC name Diphenyl oxalate
Other names diphenylethandioate, oxalic acid diphenyl ester, cyalume, DPO
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.203.380 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C14H10O4/c15-13(17-11-7-3-1-4-8-11)14(16)18-12-9-5-2-6-10-12/h1-10HKey: ULOZDEVJRTYKFE-UHFFFAOYSA-N
  • InChI=1/C14H10O4/c15-13(17-11-7-3-1-4-8-11)14(16)18-12-9-5-2-6-10-12/h1-10HKey: ULOZDEVJRTYKFE-UHFFFAOYAB
SMILES
  • O=C(Oc1ccccc1)C(=O)Oc2ccccc2
Properties
Chemical formula C14H10O4
Molar mass 242.227 g/mol
Appearance solid
Melting point 136 °C (277 °F; 409 K)
Thermochemistry
Std enthalpy of
formation (ΔfH298) 		129·0 ± 0·8
Related compounds
Related compounds Dimethyl oxalate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Diphenyl oxalate (trademark name Cyalume) is a solid whose oxidation products are responsible for the chemiluminescence in a glowstick. This chemical is the double ester of phenol with oxalic acid. Upon reaction with hydrogen peroxide, 1,2-dioxetanedione is formed, along with release of the two phenols. The dioxetanedione then reacts with a dye molecule, decomposing to form carbon dioxide and leaving the dye in an excited state. As the dye relaxes back to its unexcited state, it releases a photon of visible light.

The reaction rate is pH dependent, and slightly alkaline conditions, achieved by adding a weak base, such as sodium salicylate, give a faster reaction and therefore produce brighter light. The 2,4,6-trichlorophenol ester 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.

The following colors can be produced by using different dyes:

Color Compound
Green 9,10-Diphenylanthracene
Blue 9,10-Bis(phenylethynyl)anthracene
Yellow-green Tetracene
Yellow 1-Chloro-9,10-bis(phenylethynyl)anthracene
Orange 5,12-Bis(phenylethynyl)naphthacene, Rubrene, Rhodamine 6G
Red Rhodamine B

References

  1. Carson, A. S.; Fine, D. H.; Gray, P.; Laye, P. G. (1971). "Standard enthalpies of formation of diphenyl oxalate and benzoic anhydride and some related bond dissociation energies". Journal of the Chemical Society B: Physical Organic: 1611. doi:10.1039/J29710001611.
  2. Orosz, György (January 1989). "The role of diaryl oxalates in peroxioxalate chemiluminescence". Tetrahedron. 45 (11): 3493–3506. doi:10.1016/S0040-4020(01)81028-0.
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