Sample of pure compound | |
Names | |
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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) | |
ChemSpider | |
ECHA InfoCard | 100.157.526 |
PubChem CID | |
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 | |
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). |
TCPO, or bis(2,4,6-trichlorophenyl) oxalate, is a chemical used in some types of glow sticks.
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.
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.
TCPO can be prepared from a solution of 2,4,6-trichlorophenol in a solution of 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 triethylamine hydrochloride can be dissolved in water, methanol or ethanol, so the product is more purified. After washing it can be recrystallized from ethyl acetate.
In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively charged sodium ions and negatively charged chloride ions.
Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C14H10, consisting of three fused benzene rings. It is a component of coal tar. Anthracene is used in the production of the red dye alizarin and other dyes. Anthracene is colorless but exhibits a blue (400–500 nm peak) fluorescence under ultraviolet radiation.
A glow stick, also known as a light stick, chem light, light wand, light rod, and rave light, is a self-contained, short-term light-source. It consists of a translucent plastic tube containing isolated substances that, when combined, make light through chemiluminescence. The light cannot be turned off and can be used only once. The used tube is then thrown away. Glow sticks are often used for recreation, such as for events, camping, outdoor exploration, and concerts. Glow sticks are also used for light in military and emergency services applications. Industrial uses include marine, transportation, and mining.
Sodium acetate, CH3COONa, also abbreviated NaOAc, is the sodium salt of acetic acid. This colorless deliquescent salt has a wide range of uses.
Triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine or tetraethylammonium, for which TEA is also a common abbreviation. It is a colourless volatile liquid with a strong fishy odor reminiscent of ammonia. Like diisopropylethylamine (Hünig's base), triethylamine is commonly employed in organic synthesis, usually as a base.
Substances, mixtures and exposure circumstances in this list have been classified by the International Agency for Research on Cancer (IARC) as group 3: The agent is not classifiable as to its carcinogenicity to humans. This category is used most commonly for agents, mixtures and exposure circumstances for which the evidence of carcinogenicity is inadequate in humans and inadequate or limited in experimental animals. Exceptionally, agents (mixtures) for which the evidence of carcinogenicity is inadequate in humans but sufficient in experimental animals may be placed in this category when there is strong evidence that the mechanism of carcinogenicity in experimental animals does not operate in humans. Agents, mixtures and exposure circumstances that do not fall into any other group are also placed in this category.
Diphenyl oxalate 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. The dioxetanedione then reacts with a dye molecule, decomposing to form carbon dioxide and leaving the dye in an excited state. As the dye relaxes back to its unexcited state, it releases a photon of visible light.
Sodium formate, HCOONa, is the sodium salt of formic acid, HCOOH. It usually appears as a white deliquescent powder.
MCPO is a chemical compound that can be used to produce chemiluminescence. MCPO is mainly used for its chemiluminescent properties and is most commonly used in demonstrations of chemiluminescence as a safer alternative to TCPO. It is used as an alternative to TCPO due to its safer reaction product of methyl salicylate rather than the product of TCP, 2,4,6-trichlorophenol, a known carcinogen.
1-Chloro-9,10-bis(phenylethynyl)anthracene is a fluorescent dye used in lightsticks. It emits yellow-green light, used in 30-minute high-intensity Cyalume sticks.
5,12-Bis(phenylethynyl)naphthacene is a fluorescent dye used in lightsticks. It yields orange light.
Bis[2,4,5-trichloro-6-(pentyloxycarbonyl)phenyl]oxalate is a solid ester whose oxidation products are responsible for the chemiluminescence in a glowstick. It can be synthesized by reacting 2-carbopentoxy-3,5,6-trichlorophenol with oxalyl chloride.
Potassium ferrioxalate, also called potassium trisoxalatoferrate or potassium tris(oxalato)ferrate(III) is a chemical compound with the formula K
3[Fe(C
2O
4)
3]. It often occurs as the trihydrate K3[Fe(C2O4)3]·3H2O. Both are crystalline compounds, lime green in colour.
2-Chloro-9,10-bis(phenylethynyl)anthracene is a fluorescent dye used in lightsticks. It emits green light, used in 12-hour low-intensity Cyalume sticks.
Peroxyoxalates are esters initially formed by the reaction of hydrogen peroxide with oxalate diesters or oxalyl chloride, with or without base, although the reaction is much faster with base:
The molecular formula C30H17Cl (molar mass: 412.91 g/mol) may refer to:
Bis (2,4-dinitrophenyl) oxalate (DNPO) is a source of 1,2-dioxetanedione, a chemical used in glow sticks. Other chemicals related to DNPO used in glow sticks include bis(2,4,6-trichlorophenyl)oxalate (TCPO) and bis(2,4,5-trichlorophenyl-6-carbopentoxyphenyl)oxalate (CPPO).
2-Chloro-9,10-diphenylanthracene is a fluorescent dye used in glow sticks for a blue-green glow. It is a chlorinated derivative of 9,10-diphenylanthracene.
Ferrioxalate or trisoxalatoferrate(III) is a trivalent anion with formula [Fe(C2O4)3]3−. It is a transition metal complex consisting of an iron atom in the +3 oxidation state and three bidentate oxalate ions C2O2−4 anions acting as ligands.
Neodymium compounds are compounds formed by the lanthanide metal neodymium (Nd). In these compounds, neodymium generally exhibits the +3 oxidation state, such as NdCl3, Nd2(SO4)3 and Nd(CH3COO)3. Compounds with neodymium in the +2 oxidation state are also known, such as NdCl2 and NdI2. Some neodymium compounds have colors that vary based upon the type of lighting.