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1,2,4-Trichlorobenzene

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1,2,4-Trichlorobenzene Basic information
1,2,4-Trichlorobenzene Chemical Properties
  • Melting point:16 °C(lit.)
  • Boiling point:214 °C(lit.)
  • Density 1.454 g/mL at 25 °C(lit.)
  • vapor density >6 (vs air)
  • vapor pressure 1 mm Hg ( 40 °C)
  • refractive index n20/D 1.571(lit.)
  • Flash point:>230 °F
  • storage temp.  0-6°C
  • solubility water: insoluble
  • form Liquid
  • color Clear
  • OdorCharacteristic aromatic odor
  • explosive limit6.6%, 150°F
  • Water Solubility INSOLUBLE
  • λmaxλ: 308 nm Amax: 1.00
    λ: 310 nm Amax: 0.50
    λ: 350 nm Amax: 0.05
    λ: 375-400 nm Amax: 0.01
  • Merck 14,9631
  • BRN 956819
  • Henry's Law Constant0.997 at 20.0 °C (wetted-wall column, ten Hulscher et al., 1992) 1.24, 2.27, 2.58, 3.06, and 3.90 at 2.0, 6.0, 10.0, 18.0, and 25.0 °C, respectively (EPICS-SPME, Dewulf et al., 1999)
  • Exposure limitsNIOSH REL: TWA ceiling 5 ppm (40 mg/m3); ACGIH TLV: ceiling 5 ppm (adopted).
  • Stability:Stable. Incompatible with strong oxidizing agents. Combustible.
  • CAS DataBase Reference120-82-1(CAS DataBase Reference)
  • NIST Chemistry ReferenceBenzene, 1,2,4-trichloro-(120-82-1)
  • EPA Substance Registry System1,2,4-Trichlorobenzene (120-82-1)
Safety Information
MSDS
1,2,4-Trichlorobenzene Usage And Synthesis
  • Chemical PropertiesColorless, stable liquid; odor similar to that of o-dichlorobenzene. Miscible with most organic solvents and oils; insoluble in water. Combustible.
  • Chemical Properties1,2,4-Trichlorobenzene is a low-melting solid or liquid with a pleasant, aromatic odor. The Odor Threshold is 1.4 ppm.
  • Physical propertiesColorless liquid with an odor similar to o-dichlorobenzene. Odor threshold concentration is 1.4 (quoted, Amoore and Hautala, 1983).
  • Uses1,2,4-Trichlorobenzene is a solvent in various organic chemical reactions.
  • DefinitionChEBI: A trichlorobenzene with chloro substituents at positions 1, 2 and 4.
  • Synthesis Reference(s)Journal of the American Chemical Society, 74, p. 3890, 1952 DOI: 10.1021/ja01135a052
  • General DescriptionColorless liquid or white solid with a sharp chlorobenzene odor. Melting point 16.95°C (62.5°F) .
  • Reactivity Profile1,2,4-Trichlorobenzene can react vigorously with oxidizing materials . Yields hydrogen chloride and phosgene when heated to decomposition [USCG, 1999].
  • Health HazardExposures to high concentrations via inhalation are potentially hazardous to the lungs, kidneys and liver. Prolonged or repeated exposures or short exposure to high concentrations via inhalation are potentially hazardous to the lungs, kidneys and liver. Prolonged or repeated exposure to the eyes is likely to result in moderate pain and transient irritation. Prolonged or repeated contact with the skin may result in moderate irritation and possible systemic effects. Ingestion: May cause kidney and liver damage.
  • Safety ProfilePoison by ingestion. Moderately toxic by intraperitoneal route. An experimental teratogen. Experimental reproductive effects. Mutation data reported. A slan irritant. Combustible when exposed to heat or flame. Can react vigorously with oxidizing materials. To fight fire, use water, foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of Cl-. See also CHLORINATED HYDROCARBONS, AROMATIC.
  • Potential Exposure1,2,4-Trichlorobenzene is used as a dye carrier, herbicide intermediate; a heat transfer medium; a dielectric fluid in transformers; a degreaser; a lubricant; as an industrial chemical; solvent, emulsifier, and as a potential insecticide against termites. The other trichlorobenzene isomers are not used in any quantity.
  • Environmental FateBiological. Under aerobic conditions, biodegradation products may include 1,2-dichlorobenzene, 1,3-dichlorobenzene, 1,4-dichlorobenzene, and carbon dioxide (Kobayashi and Rittman, 1982). A mixed culture of soil bacteria or a Pseudomonas sp. transformed 1,2,4-trichlorobenzene to 2,4,5- and 2,4,6-trichlorophenol (Ballschiter and Scholz, 1980). When 1,2,4- trichlorobenzene was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, significant biodegradation occurred, with gradual acclimation followed by a deadaptive process in subsequent subcultures. At a concentration of 5 mg/L, 54, 70, 59, and 24% losses were observed after 7, 14, 21, and 28-d incubation periods, respectively. At a concentration of 10 mg/L, only 43, 54, 14, and 0% were observed after 7, 14, 21, and 28-d incubation periods, respectively (Tabak et al., 1981). In activated sludge, <0.1% mineralized to carbon dioxide after 5 d (Freitag et al., 1985).
    In an enrichment culture derived from a contaminated site in Bayou d’Inde, LA, 1,2,4- trichlorobenzene underwent reductive dechlorination to 1,3- and 1,4-dichlorobenzene at relative molar yields of 4 and 96%, respectively. The maximum dechlorination rate, based on the recommended Michaelis-Menten model, was 4.6 nM/d (Pavlostathis and Prytula, 2000).
    Surface Water. Estimated half-lives of 1,2,4-trichlorobenzene (0.5 μg/L) from an experimental marine mesocosm during the spring (8–16 °C), summer (20–22 °C), and winter (3–7 °C) were 22, 11, and 12 d, respectively (Wakeham et al., 1983).
    Photolytic. A carbon dioxide yield of 9.8% was achieved when 1,2,4-trichlorobenzene adsorbed on silica gel was irradiated with light (λ >290 nm) for 17 h (Freitag et al., 1985).
    Chemical/Physical. The hydrolysis half-life was estimated to be >900 yr (Ellington et al., 1988). At 70.0 °C and pH values of 3.10, 7.11, and 9.77, the hydrolysis half-lives were calculated to be 18.4, 6.6, and 5.9 d, respectively (Ellington et al., 1986).
    At influent concentrations of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC adsorption capacities were 157, 77.6, 38.4, and 19.0 mg/g, respectively (Dobbs and Cohen, 1980).
  • ShippingUN2321 Trichlorobenzenes, liquid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
  • Purification MethodsSeparate it from a mixture of isomers by washing with fuming H2SO4, then water, drying with CaSO4 and slowly fractionally distilling. [Jensen et al. J Am Chem Soc 81 3303 1959, Beilstein 5 IV 664.]
  • IncompatibilitiesReacts violently with oxidants, acids, acid fumes; steam.
  • Waste DisposalIncineration, preferably after mixing with another combustible fuel. Care must be exercised to assure complete combustion to prevent the formation of phosgene. An acid scrubber is necessary to remove the halo acids produced.
1,2,4-Trichlorobenzene Preparation Products And Raw materials
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