TCPO

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TCPO
TCPO.png
Bis(2,4,6-trichlorophenyl) 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)
ChemSpider
ECHA InfoCard 100.157.526 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
  • InChI=/C14H4Cl6O4/c15-5-1-7(17)11(8(18)2-5)23-13(21)14(22)24-12-9(19)3-6(16)4-10(12)20/h1-4H
  • O=C(C(OC1=C(Cl)C=C(Cl)C=C1Cl)=O)OC2=C(Cl)C=C(Cl)C=C2Cl
Properties
C14H4Cl6O4
Molar mass 448.88 g·mol−1
AppearanceWhite 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.

Contents

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.

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 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.

See also

Related Research Articles

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<span class="mw-page-title-main">Anthracene</span> Chemical compound

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.

<span class="mw-page-title-main">Glow stick</span> Self-contained, short-term light source

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<span class="mw-page-title-main">Sodium acetate</span> Chemical compound

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.

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<span class="mw-page-title-main">Diphenyl oxalate</span> Chemical compound

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.

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<span class="mw-page-title-main">Sodium formate</span> Chemical compound

Sodium formate, HCOONa, is the sodium salt of formic acid, HCOOH. It usually appears as a white deliquescent powder.

<span class="mw-page-title-main">MCPO</span> Chemical compound

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.

<span class="mw-page-title-main">1-Chloro-9,10-bis(phenylethynyl)anthracene</span> Chemical compound

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.

<span class="mw-page-title-main">Bis(2,4,5-trichloro-6-(pentyloxycarbonyl)phenyl)oxalate</span> Chemical compound

Bis[2,4,5-trichloro-6-(pentyloxycarbonyl)phenyl]oxalate 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. It can be synthesized by reacting 2-carbopentoxy-3,5,6-trichlorophenol with oxalyl chloride.

<span class="mw-page-title-main">Potassium ferrioxalate</span> Chemical compound

Potassium ferrioxalate, also called potassium trisoxalatoferrate or potassium tris(oxalato)ferrate(III) is a chemical compound with the formula K3[Fe(C2O4)3]. It often occurs as the trihydrate K3[Fe(C2O4)3]·3H2O. Both are crystalline compounds, lime green in colour.

<span class="mw-page-title-main">Peroxyoxalate</span>

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:

<span class="mw-page-title-main">Bis(2,4-dinitrophenyl) oxalate</span> Chemical compound

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).

<span class="mw-page-title-main">2-Chloro-9,10-diphenylanthracene</span> Chemical compound

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.

<span class="mw-page-title-main">1,3-Diphenylisobenzofuran</span> Chemical compound

1,3-Diphenylisobenzofuran is a highly reactive diene that can scavenge unstable and short-lived dienophiles in a Diels-Alder reaction. It is furthermore used as a standard reagent for the determination of singlet oxygen, even in biological systems. Cycloadditions with 1,3-diphenylisobenzofuran and subsequent oxygen cleavage provide access to a variety of polyaromatics.

<span class="mw-page-title-main">Ferrioxalate</span> Ion

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.

<span class="mw-page-title-main">Neodymium compounds</span> Chemical compounds with at least one neodymium atom

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.

References

  1. Mohan, Arthur G.; Turro, Nicholas J. (August 1974). "A Facile and Effective Chemiluminescence Demonstration Experiment". Journal of Chemical Education. 51 (8): 528. Bibcode:1974JChEd..51..528M. doi:10.1021/ed051p528.