CPPO

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

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

Chemical compound

Bis[2,4,5-trichloro-6-(pentyloxycarbonyl)phenyl]oxalate (also known as bis(2,4,5-trichloro-6-carbopentoxyphenyl) oxalate or CPPO) is an organic compound with the formula (C5H11O2CC6HCl3O)2C2O2. A white solid, it is classified as a diester of oxalic acid. It is an active ingredient for the chemiluminescence in glowsticks.[1] It can be synthesized by reacting 2-carbopentoxy-3,5,6-trichlorophenol with oxalyl chloride.

Quick Facts Names, Identifiers ...
"CPPO" redirects here. For dcpos with a minimal element, see complete partial order.

When mixed with hydrogen peroxide in an organic solvent (diethyl phthalate, ethyl acetate, etc...) in the presence of a fluorescent dye CPPO causes the emission of light, following its degradation to 1,2-dioxetanedione (note that many side-groups of the aromatic rings are not shown.):[2]

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.

The following colors can be produced by using different dyes:

More information Color, Compound ...

References

  1. [1]
    Eghlimi, Abbas; Jubaer, Hasan; Surmiak, Adam; Bach, Udo (2019). "Developing a Safe and Versatile Chemiluminescence Demonstration for Studying Reaction Kinetics". Journal of Chemical Education. 96 (3): 522–527. Bibcode:2019JChEd..96..522E. doi:10.1021/acs.jchemed.8b00614.
  2. [2]
    Yoshinaga, Tetsutaro; Tanaka, Yasuo; Ichimura, Teijiro; Hiratsuka, Hiroshi; Hasegawa, Miki; Kobayashi, Michio; Hoshi, Toshihiko (2001). "Solid Surface Enhancement Effects on Chemiluminescence. III. Diaryloxalate as Chemiluminescence Reagent and Inorganic Materials as Media Solids". Bulletin of the Chemical Society of Japan. 74 (8): 1507–1516. doi:10.1246/bcsj.74.1507.
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