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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]
Oxalate (systematic IUPAC name: ethanedioate) is an anion with the chemical formula C 2 O 2− 4.This dianion is colorless. It occurs naturally, including in some foods. It forms a variety of salts, for example sodium oxalate (Na 2 C 2 O 4), and several esters such as dimethyl oxalate ((CH 3) 2 C 2 O 4).
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]
Luminol (C 8 H 7 N 3 O 2) is a chemical that exhibits chemiluminescence, with a blue glow, when mixed with an appropriate oxidizing agent.Luminol is a white-to-pale-yellow crystalline solid that is soluble in most polar organic solvents but insoluble in water.
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.
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).
Unlike other malonic esters that are derived via malonic ester synthesis, diethyl phenylmalonate is typically indirectly derived via a Claisen condensation with diethyl oxalate and ethyl phenylacetate followed by decarbonylation. [2]