Omar Bennett
Trichlorobenzene (TCB) is any of three isomeric chlorinated derivatives of benzene with the molecular formula C6H3Cl3. The three isomers are differentiated by the positions of the chlorine atoms around the ring. The three possible isomers are 1,2,3-trichlorobenzene, 1,2,4-trichlorobenzene, and 1,3,5-trichlorobenzene.
| Characteristics | Values |
|---|---|
| Number of Constitutional Isomers | 3 |
| Isomers | 1,2,3-trichlorobenzene, 1,2,4-trichlorobenzene, and 1,3,5-trichlorobenzene |
| Chemical Identity | Shown in Table 4-1 of the Agency for Toxic Substances and Disease Registry (US) |
| Use | Used as an intermediate for pesticides production, pigments, dyes, degreasing agents, septic tanks, drain cleaners, wood preservatives, and abrasive formulations |
| Other Uses | Metal work, anticorrosive paint, corrosion inhibitor in sprays, termite control |
| Toxicity | Moderate to high toxicity with aquatic organisms |
| Administration Route | Inhalation, ingestion of food and drinking water |
| Target Organ | Liver |
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What You'll Learn
Trichlorobenzene has three isomers
Trichlorobenzene (TCB) has three isomers: 1,2,3-trichlorobenzene, 1,2,4-trichlorobenzene, and 1,3,5-trichlorobenzene. These isomers are derivatives of benzene with the molecular formula C6H3Cl3, and they differ by the positions of the chlorine atoms around the ring.
The isomers of trichlorobenzene have a variety of uses and applications. For example, 1,2,3-trichlorobenzene is used as an intermediate in the production of pesticides, pigments, and dyes. It is also used as a degreasing agent and in septic tanks and drain cleaners. On the other hand, 1,2,4-trichlorobenzene is listed as a hazardous air pollutant under the Clean Air Act, and it has been found to be cytotoxic to rat hepatocytes and Chinese hamster ovary cells. The third isomer, 1,3,5-trichlorobenzene, is not marketed commercially and has very limited use as a chemical intermediate.
The trichlorobenzenes, in general, are synthetic chemicals primarily used as solvents in chemical industries. They are relatively volatile and hydrophobic. They can also be used in wood preservatives, abrasive formulations, metal work, anticorrosive paint, and corrosion inhibitors in sprays. Historically, mixed isomers of trichlorobenzenes were used to control termites, but this practice has been discontinued.
The production of chlorobenzene, which can lead to the formation of trichlorobenzenes, has been declining since its peak in 1969 due to the substitution of more environmentally acceptable chemicals. This decline is expected to continue as more environmentally friendly alternatives are adopted.
In summary, trichlorobenzene has three isomers, each with distinct properties and applications. These isomers play a role in various industrial processes and have been studied for their potential environmental and health impacts.
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1,2,3-trichlorobenzene is used in pesticides
Trichlorobenzene (TCB) refers to any of the three isomeric chlorinated derivatives of benzene with the molecular formula C6H3Cl3. The three isomers are: 1,2,3-trichlorobenzene, 1,2,4-trichlorobenzene, and 1,3,5-trichlorobenzene.
1,2,3-Trichlorobenzene is used as an intermediate for pesticide production, pigments, and dyes. It is a colourless solid. It can react with oxidizing agents and may emit toxic hydrogen chloride and phosgene gases when burned. It is also known to be toxic to humans, with exposure potentially causing redness, irritation, and respiratory issues.
The other two isomers have different chemical and toxicological properties. 1,2,4-TCB is a hazardous air pollutant and has been found to be toxic to animals, causing liver issues and, in some cases, cancer. 1,3,5-Trichlorobenzene is not marketed commercially and has very limited use as a chemical intermediate.
In the past, mixed isomers of trichlorobenzenes were used to control termites, but their use has been discontinued. Trichlorobenzenes are now primarily used as solvents in chemical industries and have other minor uses, including in metal work, anticorrosive paint, and as a corrosion inhibitor in sprays.
Overall, while 1,2,3-trichlorobenzene is used in pesticide production, it is important to note that it is just one intermediate ingredient among many in the production process, and its use is subject to strict safety precautions due to its toxic nature.
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1,2,4-trichlorobenzene is a hazardous air pollutant
Trichlorobenzene (TCB) refers to any of the three isomeric chlorinated derivatives of benzene with the molecular formula C6H3Cl3. These isomers are differentiated by the positions of the chlorine atoms around the ring. The three isomers of trichlorobenzene are 1,2,3-trichlorobenzene, 1,2,4-trichlorobenzene, and 1,3,5-trichlorobenzene.
1,2,4-trichlorobenzene is one of the isomers of trichlorobenzene that is listed as a hazardous air pollutant under the Clean Air Act. It is a synthetic chemical that is primarily used as a solvent in chemical industries. 1,2,4-trichlorobenzene is released into the environment through its production and use, with an estimated release of approximately 30,373 pounds (13.8 metric tons) into the atmosphere from 17 domestic manufacturing and processing facilities in 2008. It has been detected in outdoor air, groundwater, drinking water, surface water, soil, and sediment, with an average concentration of less than 1 ppbv in most US locations sampled.
The general population may be exposed to 1,2,4-trichlorobenzene through inhalation and ingestion of contaminated food, drinking water, or occupational exposures. People residing near hazardous waste sites are at a higher risk of exposure. Certain food items, including vegetables, milk, eggs/meat, and oils produced from corn, soybeans, peanuts, and poppy seeds, have been found to contain 1,2,4-trichlorobenzene.
Toxicity studies in rodents have identified the liver as the primary target organ for 1,2,4-trichlorobenzene exposure. Chronic studies in animals have reported liver weight changes, hepatocellular hypertrophy, focal cystic degeneration, and hepatocellular carcinoma. In vitro assays have also shown cytotoxicity in rat hepatocytes and Chinese hamster ovary cells by inhibiting protein and DNA synthesis.
Overall, 1,2,4-trichlorobenzene is a hazardous air pollutant due to its toxic effects on the environment and human health, with potential exposure through various routes, including inhalation and ingestion of contaminated food and water.
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1,3,5-trichlorobenzene is not marketed commercially
Trichlorobenzene (TCB) refers to three isomeric chlorinated derivatives of benzene with the molecular formula C6H3Cl3. The three isomers are 1,2,3-trichlorobenzene, 1,2,4-trichlorobenzene, and 1,3,5-trichlorobenzene. While the first two isomers are commercially used, 1,3,5-trichlorobenzene is not marketed commercially and has very limited use as a chemical intermediate.
The three isomers of trichlorobenzene have different chemical and toxicological properties. 1,2,4-TCB is listed as a hazardous air pollutant under the Clean Air Act. It is used as a solvent in chemical reactions to dissolve oils, waxes, and resins, and as a dye carrier. It is the most economically important isomer of trichlorobenzene. 1,2,3-Trichlorobenzene is used as an intermediate for pesticides production, pigments, and dyes.
On the other hand, 1,3,5-trichlorobenzene is not widely sold commercially. It is used for some applications, such as a termite preparation and insecticide. It is an isomer of 1,2,4-Trichlorobenzene, which is a solvent in various organic chemical reactions. Trichlorobenzenes are primarily used as solvents in chemical manufacturing industries. However, 1,3,5-trichlorobenzene has limited use as a chemical intermediate.
The limited commercial availability of 1,3,5-trichlorobenzene could be due to various reasons. One possibility is that this particular isomer may have less favourable chemical or physical properties compared to the other two isomers. For example, it may have a lower solubility or reactivity that makes it less suitable for certain applications. Additionally, the economic viability of commercializing 1,3,5-trichlorobenzene may be a factor. The demand for this specific isomer might not be high enough to justify the costs of production and distribution on a large scale.
Another factor to consider is the regulatory environment surrounding hazardous substances. Given that trichlorobenzenes are synthetic chemicals with known toxicological effects, there may be strict regulations in place that limit the commercial use of certain isomers, including 1,3,5-trichlorobenzene. The potential health and environmental risks associated with this isomer could be a deterrent for commercial marketing.
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Trichlorobenzenes are used in metal work
Trichlorobenzenes are synthetic chemicals that exist in three isomeric forms: 1,2,3-trichlorobenzene, 1,2,4-trichlorobenzene, and 1,3,5-trichlorobenzene. They are primarily used as solvents in chemical industries and have a range of applications, including metal work.
In metal work, trichlorobenzenes can be used as degreasing agents, aiding in the removal of grease, oil, and other contaminants from metal surfaces. This is an important step in the metal fabrication process, as it prepares the metal for further treatment, such as painting or welding. Trichlorobenzenes are effective degreasers due to their hydrophobic and solvent properties. Their ability to dissolve grease and oil while repelling water makes them useful in cleaning and preparing metal surfaces.
Additionally, trichlorobenzenes can be used as corrosion inhibitors in metal work. They can be applied as anti-corrosive coatings or incorporated into paints and sprays to protect metal surfaces from oxidation and degradation. This application is particularly valuable in industries where metal structures are exposed to harsh environmental conditions, such as marine or industrial settings.
The use of trichlorobenzenes in metal work offers advantages in terms of their solvent strength and effectiveness in removing contaminants. However, it is important to consider the potential health and environmental hazards associated with these chemicals. Trichlorobenzenes are considered toxic and can pose risks through inhalation or skin contact. Proper protective equipment and handling procedures are essential when working with these substances.
Furthermore, trichlorobenzenes have been listed as hazardous air pollutants under the Clean Air Act. Their release into the environment during production or use can lead to contamination of water, soil, and sediment. Due to these concerns, the use of trichlorobenzenes has been declining, and efforts are being made to substitute them with more environmentally acceptable alternatives.
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Frequently asked questions
There are three constitutional isomers of trichlorobenzene: 1,2,3-trichlorobenzene, 1,2,4-trichlorobenzene, and 1,3,5-trichlorobenzene.
All three isomers have the molecular formula C6H3Cl3 and differ in the positions of the chlorine atoms around the ring. They are synthetic chemicals used primarily as solvents in the chemical industry. They are also used in pesticides, pigments, dyes, and other applications.
The 1,2,4-TCB isomer is listed as a hazardous air pollutant under the Clean Air Act. Trichlorobenzenes exhibit moderate to high toxicity to aquatic organisms and can enter the body through inhalation or ingestion. The liver is the target organ affected by these isomers.
Chlorobenzene production peaked in 1969 and has been declining due to the adoption of more environmentally friendly alternatives. In the past, mixed isomers of trichlorobenzenes were used for termite control, but this practice has been discontinued.
