TCPO
Chemical compound
From Wikipedia, the free encyclopedia
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.
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_oxalate.jpg) Sample of pure compound | |
| Names | |
|---|---|
| Preferred IUPAC name
Bis(2,4,6-trichlorophenyl) oxalate | |
| Other names
Bis(2,4,6-trichlorophenyl) ethanedioate; Oxalic acid, bis(2,4,6-trichlorophenyl) ester | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.157.526 |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C14H4Cl6O4 | |
| Molar mass | 448.88 g·mol−1 |
| Appearance | White crystalline powder |
| Density | 1.698 g/cm3 |
| Melting point | 188 to 192 °C (370 to 378 °F; 461 to 465 K) |
| Boiling point | 500.9 °C (933.6 °F; 774.0 K) |
| 0.01962 mg/L | |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H315, H319, H335 | |
| P261, P264, P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501 | |
| Flash point | 190.6 °C (375.1 °F; 463.8 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Uses
When combined with a fluorescent dye like 9,10-bis(phenylethynyl)anthracene, a solvent (such as diethyl phthalate), and a weak base (usually sodium acetate or sodium salicylate), and hydrogen peroxide, the mixture will start a chemiluminescent reaction to glow a fluorescent green color.[1]
Red, yellow and blue colors can be made by replacing the 9,10-bis(phenylethynyl)anthracene with rhodamine B, rubrene and 9,10-diphenylanthracene respectively.[2]
The above fluorescent dyes absorb much of the energy produced during the decomposition of the oxalate ester, and convert that energy into light energy which is observed as the characteristic glow in products such as glowsticks.
Preparation
TCPO can be prepared from a solution of 2,4,6-trichlorophenol in dry toluene by reaction with oxalyl chloride in the presence of a base such as triethylamine. This method produces crude TCPO with a by-product of triethylamine hydrochloride. The product is washed with water to remove the byproduct and recrystallized from toluene.[3]