Names | |
---|---|
Preferred IUPAC name
Bis{3,4,6-trichloro-2-[(pentyloxy)carbonyl]phenyl} oxalate | |
Other names
CPPO
| |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
ECHA InfoCard | 100.045.618 |
PubChem
CID
|
|
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C26H24Cl6O8 | |
Molar mass | 677.17 g·mol−1 |
Melting point | 188 to 192 °C (370 to 378 °F; 461 to 465 K) |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
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.
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:
Color | Compound |
---|---|
Blue | 9,10-Diphenylanthracene |
Green | 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 | 2,4-Di-tert-butylphenyl 1,4,5,8-tetracarboxynaphthalene diamide, Rhodamine 101, Rhodamine B |
Names | |
---|---|
Preferred IUPAC name
Bis{3,4,6-trichloro-2-[(pentyloxy)carbonyl]phenyl} oxalate | |
Other names
CPPO
| |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
ECHA InfoCard | 100.045.618 |
PubChem
CID
|
|
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C26H24Cl6O8 | |
Molar mass | 677.17 g·mol−1 |
Melting point | 188 to 192 °C (370 to 378 °F; 461 to 465 K) |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
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.
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:
Color | Compound |
---|---|
Blue | 9,10-Diphenylanthracene |
Green | 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 | 2,4-Di-tert-butylphenyl 1,4,5,8-tetracarboxynaphthalene diamide, Rhodamine 101, Rhodamine B |