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 and is a key chemical in many chemiluminescent reactions. TCPO is classified as damaging to human organs and toxic if inhaled with an inhalable toxicity of 3.02 mg/L and oral toxicity LD50 of 820 mg/kg (rat). Additionally, TCPO is considered a danger to drinking water if even small quantities leak into the ground, and if spilled it is recommended to soak up with wood chips or absorbent material then disposing of as hazardous waste. [1]
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. [2]
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.
Human SafetyRecommendations
Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection.
If on skin (or hair): Take off immediately all contaminated clothing. Rinse skin with water/shower. Call a POISON CENTER or doctor/physician.
If Inhaled : Remove person to fresh air and keep comfortable for breathing.Call a POISON CENTER or doctor/physician. In case of unconsciousness place patient stably in side position for transportation.
Environmental Safety and Waste Management Recommendations
Must not be disposed of together with household garbage. Do not allow product to reach sewage system. Disposal must be made according to official regulations. : Do not allow to enter sewers/ surface or ground water. If there is a spill, it is recommended to absorb with liquid-binding material (sand, diatomite, acid binders, universal binders, sawdust) then dispose of as 'hazardous waste'.
Toxic waste is any unwanted material in all forms that can cause harm. Mostly generated by industry, consumer products like televisions, computers, and phones contain toxic chemicals that can pollute the air and contaminate soil and water. Disposing of such waste is a major public health issue.
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.
Luminol (C8H7N3O2) is a chemical that exhibits chemiluminescence, with a blue glow, when mixed with an appropriate oxidizing agent. Luminol is a white-to-pale-yellow crystalline solid that is soluble in most polar organic solvents but insoluble in water.
Pentachlorophenol (PCP) is an organochlorine compound used as a pesticide and a disinfectant. First produced in the 1930s, it is marketed under many trade names. It can be found as pure PCP, or as the sodium salt of PCP, the latter of which dissolves easily in water. It can be biodegraded by some bacteria, including Sphingobium chlorophenolicum.
Oxalyl chloride is an organic chemical compound with the formula Cl−C(=O)−C(=O)−Cl. This colorless, sharp-smelling liquid, the diacyl chloride of oxalic acid, is a useful reagent in organic synthesis.
Ethylbenzene is an organic compound with the formula C6H5CH2CH3. It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as a reaction intermediate in the production of styrene, the precursor to polystyrene, a common plastic material. In 2012, more than 99% of ethylbenzene produced was consumed in the production of styrene.
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.
IARC group 3 substances, chemical mixtures and exposure circumstances are those that can not be classified in regard to their carcinogenicity to humans by the International Agency for Research on Cancer (IARC). This category is used most commonly for agents, mixtures and exposure circumstances for which the level of 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.
This is the list of extremely hazardous substances defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act. The list can be found as an appendix to 40 CFR 355. Updates as of 2006 can be seen on the Federal Register, 71 FR 47121.
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.
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.
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:
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.
Chemical safety includes all safety policies, procedures and practices designed to minimize the risk of exposure to potentially hazardous chemicals. This includes the risks of exposure to persons handling the chemicals, to the surrounding environment, and to the communities and ecosystems within that environment. Manufactured chemicals, either pure or in mixtures, solutions and emulsions, are ubiquitous in modern society, at industrial, occupational and private scale. However, there are chemicals that should not mix or get in contact with others, as they can produce byproducts that may be toxic, carcinogenic, explosive etc., or can be dangerous in themselves. To avoid disasters and mishaps, maintaining safety is paramount.
Ohio River Park is a Superfund Site located in Neville Island, Pennsylvania. Between the 1920s-1970s, the Site was used for municipal waste, pesticide manufacturing, coke sludge disposal, cement manufacturing disposal, and pesticide waste. In 1977, Neville Land Company donated the Site to Allegheny County who started developing the Site as a community park. In 1979, Allegheny County found various hazardous contaminants on the Site. On August 30, 1990, the Site was determined to be a Superfund Site due to VOCs, SVOCs, inorganics, and pesticides being present in the surface soil, subsurface soil, surface water, river sediment, and groundwater. Soil remediation began in February 1998 and ended in September 1999. Today, Ohio River Park has the Robert Morris University Island Sports Center and Coraopolis Bridge on top of it. Additionally, benzene continues to be monitored because it is still present in the Site's groundwater.
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.