Diphenyl oxalate

Names
Preferred IUPAC name

Diphenyl oxalate

Other names

diphenylethandioate, oxalic acid diphenyl ester, cyalume, DPO

Identifiers

CAS Number

* 3155-16-6 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 17449 N

ECHA InfoCard | 100.203.380

PubChem CID

* 18475

CompTox Dashboard (EPA)

* DTXSID50185452

InChI

* InChI=1S/C14H10O4/c15-13(17-11-7-3-1-4-8-11)14(16)18-12-9-5-2-6-10-12/h1-10H N

Key: ULOZDEVJRTYKFE-UHFFFAOYSA-N N

* InChI=1/C14H10O4/c15-13(17-11-7-3-1-4-8-11)14(16)18-12-9-5-2-6-10-12/h1-10H

Key: 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 (ΔfH⦵298)

| 129·0 ± 0·8[1]
Related compounds

Related compounds

| Dimethyl oxalate

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)

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.[2] 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.[clarification needed] 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

[edit]

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.

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency