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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 chemicals inside the plastic tube are a mixture of the dye, the base catalyst, and diphenyl oxalate. The chemical in the glass vial is hydrogen peroxide. By mixing the peroxide with the phenyl oxalate ester, a chemical reaction takes place, yielding two moles of phenol and one mole of peroxyacid ester (1,2-dioxetanedione). [18]
Peroxyoxalate chemiluminescence (CL) was first reported by Rauhut in 1967 [1] in the reaction of diphenyl oxalate. The emission is generated by the reaction of an oxalate ester with hydrogen peroxide in the presence of a suitably fluorescent energy acceptor. This reaction is used in glow sticks.
Oxalate also forms coordination compounds where it is sometimes abbreviated as ox. It is commonly encountered as a bidentate ligand. When the oxalate chelates to a single metal center, it always adopts the planar conformation. As a bidentate ligand, it forms a 5-membered MC 2 O 2 ring. An illustrative complex is potassium ferrioxalate, K 3 [Fe ...
Diphenyl oxalate is obtained by transesterification with phenol in the presence of titanium catalysts, [14] which is again decarbonylated to diphenyl carbonate in the liquid or gas phase. Dimethyl oxalate can also be used as a methylating agent. It is notably less toxic than other methylating agents such as methyl iodide or dimethyl sulfate. [15]
Bis(2,4-dinitrophenyl) oxalate (DNPO) is a source of 1,2-dioxetanedione, a chemical used in glow sticks. [1] Other chemicals related to DNPO used in glow sticks include bis(2,4,6-trichlorophenyl)oxalate (TCPO) and bis(2,4,5-trichlorophenyl-6-carbopentoxyphenyl)oxalate (CPPO).
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TCPO, or bis(2,4,6-trichlorophenyl) oxalate, is a chemical used in some types of glow sticks and is a key chemical in many chemiluminescent reactions. TCPO is classified as damaging to human organs and toxic if inhaled with an inhalable toxicity of 3.02 mg/L and oral toxicity LD50 of 820 mg/kg (rat).