Bis(2,4,5-trichloro-6-(pentyloxycarbonyl)phenyl)oxalate


Bisoxalate is an organic compound with the formula. A white solid, it is classified as a diester of oxalic acid. It is an active ingredient for the chemiluminescence in glow sticks. It can be synthesized by reacting 2-carbopentoxy-3,5,6-trichlorophenol with oxalyl chloride.
When mixed with hydrogen peroxide in an organic solvent in the presence of a fluorescent dye CPPO causes the emission of light, following its degradation to 1,2-dioxetanedione :
The reaction rate is pH dependent, and slightly alkaline conditions achieved by adding a weak base, e.g. sodium salicylate, will produce brighter light. Developed by American Cyanamid in the 1960s, the formulation containing CPPO, a fluorescer, and a glass capsule containing hydrogen peroxide and a base catalyst, all in dialkyl phthalate solvents, was marketed as Cyalume. Current Cyalume products no longer use any phthalate solvents.
The following colors can be produced by using different dyes:
ColorCompound
Blue9,10-Diphenylanthracene
Green9,10-Bis(phenylethynyl)anthracene
Yellow-greenTetracene
Yellow1-Chloro-9,10-bis(phenylethynyl)anthracene
Orange5,12-Bis(phenylethynyl)naphthacene, Rubrene, Rhodamine 6G
Red2,4-Di-tert-butylphenyl 1,4,5,8-tetracarboxynaphthalene diamide, Rhodamine 101, Rhodamine B