Diphenyl oxalate

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Diphenyl oxalate
Phenyl oxalate ester.png
Diphenyl oxalate 3D ball.png
Names
Preferred IUPAC name
Diphenyl oxalate
Other names
diphenylethandioate, oxalic acid diphenyl ester, cyalume, DPO
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.203.380 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
  • 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 X mark.svgN
    Key: ULOZDEVJRTYKFE-UHFFFAOYSA-N X mark.svgN
  • 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
  • O=C(Oc1ccccc1)C(=O)Oc2ccccc2
Properties
C14H10O4
Molar mass 242.227 g/mol
Appearancesolid
Melting point 136 °C (277 °F; 409 K)
Thermochemistry
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).
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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.

Cyalume-reactions.svg

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:

ColorCompound
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

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<span class="mw-page-title-main">Phosphorescence</span> Process in which energy absorbed by a substance is released relatively slowly in the form of light

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<span class="mw-page-title-main">Luminol</span> Chemical compound

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<span class="mw-page-title-main">Diazonium compound</span> Group of organonitrogen compounds

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Bis[2,4,5-trichloro-6-(pentyloxycarbonyl)phenyl]oxalate is a solid ester whose oxidation products are responsible for the chemiluminescence in a glowstick. It can be synthesized by reacting 2-carbopentoxy-3,5,6-trichlorophenol with oxalyl chloride.

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Dimethyl carbonate (DMC) is an organic compound with the formula OC(OCH3)2. It is a colourless, flammable liquid. It is classified as a carbonate ester. This compound has found use as a methylating agent and more recently as a solvent that is exempt from the restrictions placed on most volatile organic compounds (VOCs) in the United States. Dimethyl carbonate is often considered to be a green reagent.

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<span class="mw-page-title-main">Electrochemiluminescence</span> Emission of light from electrochemical reactions

Electrochemiluminescence or electrogenerated chemiluminescence (ECL) is a kind of luminescence produced during electrochemical reactions in solutions. In electrogenerated chemiluminescence, electrochemically generated intermediates undergo a highly exergonic reaction to produce an electronically excited state that then emits light upon relaxation to a lower-level state. This wavelength of the emitted photon of light corresponds to the energy gap between these two states. ECL excitation can be caused by energetic electron transfer (redox) reactions of electrogenerated species. Such luminescence excitation is a form of chemiluminescence where one/all reactants are produced electrochemically on the electrodes.

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<span class="mw-page-title-main">Diphenyl carbonate</span> Chemical compound

Diphenyl carbonate is the organic compound with the formula (C6H5O)2CO. It is classified as an acyclic carbonate ester. It is a colorless solid. It is both a monomer in combination with bisphenol A in the production of polycarbonate polymers and a product of the decomposition of polycarbonates.

<span class="mw-page-title-main">1,2-Dioxetanedione</span> Chemical compound

The chemical compound 1,2-dioxetanedione, or 1,2-dioxacyclobutane-3,4-dione, often called peroxyacid ester, is an unstable oxide of carbon (an oxocarbon) with formula C2O4. It can be viewed as a double ketone of 1,2-dioxetane (1,2-dioxacyclobutane), or a cyclic dimer of carbon dioxide.

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TCPO, or bis(2,4,6-trichlorophenyl) oxalate, is a chemical used in some types of glow sticks.

<i>o</i>-Cresolphthalein Chemical compound

o-Cresolphthalein is a phthalein dye used as a pH indicator in titrations. It is insoluble in water but soluble in ethanol. Its solution is colourless below pH 8.2, and purple above 9.8. Its molecular formula is C22H18O4. It is used medically to determine calcium levels in the human body, or to synthesize polyamides or polyimides.

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.