1,2,4-Trichlorbenzol

Bezeichnung:1,2,4-Trichlorbenzol

CAS-Nr120-82-1

Englisch Name:1,2,4-Trichlorobenzene

CBNumberCB8852926

SummenformelC6H3Cl3

Molgewicht181.45

MOL-Datei120-82-1.mol

Synonyma

1,2,4-Trichlorbenzol

1,2,4-Trichlorbenzen

unsym-Trichlorbenzol

1,2,4-Trichlorbenzol physikalisch-chemischer Eigenschaften

Schmelzpunkt	16 °C(lit.)
Siedepunkt	214 °C(lit.)
Dichte	1.454 g/mL at 25 °C(lit.)
Dampfdichte	>6 (vs air)
Dampfdruck	1 mm Hg ( 40 °C)
Brechungsindex	n20/D 1.571(lit.)
Flammpunkt	>230 °F
storage temp.	2-8°C
Löslichkeit	water: insoluble
Aggregatzustand	Liquid
Farbe	Clear
Geruch (Odor)	Characteristic aromatic odor
Explosionsgrenze	6.6%, 150°F
Wasserlöslichkeit	INSOLUBLE
maximale Wellenlänge (λmax)	λ: 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 Constant	0.997 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)
Expositionsgrenzwerte	NIOSH REL: TWA ceiling 5 ppm (40 mg/m³); ACGIH TLV: ceiling 5 ppm (adopted).
Dielectric constant	2.2400000000000002
Stabilität	Stable. Incompatible with strong oxidizing agents. Combustible.
LogP	4.28
CAS Datenbank	120-82-1(CAS DataBase Reference)
NIST chemische Informationen	Benzene, 1,2,4-trichloro-(120-82-1)
EPA chemische Informationen	1,2,4-Trichlorobenzene (120-82-1)

Sicherheit

Kennzeichnung gefährlicher	Xn,N,Xi,T,F
R-Sätze:	22-38-50/53-52/53-39/23/24/25-23/24/25-11-51/53
S-Sätze:	23-37/39-60-61-45-36/37-16-7
RIDADR	UN 2321 6.1/PG 3
OEL	Ceiling: 5 ppm (40 mg/m3)
WGK Germany	3
RTECS-Nr.	DC2100000
Selbstentzündungstemperatur	571 °C
Hazard Note	Irritant
TSCA	Yes
HazardClass	6.1
PackingGroup	III
HS Code	29036990
Giftige Stoffe Daten	120-82-1(Hazardous Substances Data)
Toxizität	LD50 orally in Rabbit: 550 mg/kg LD50 dermal Rat 6139 mg/kg

Gefahreninformationscode (GHS)

1,2,4-Trichlorobenzene Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD
FARBLOSE FLüSSIGKEITODER WEISSE KRISTALLE MIT CHARAKTERISTISCHEM GERUCH.
CHEMISCHE GEFAHREN
Zersetzung beim Verbrennen unter Bildung giftiger Rauche mit Chlorwasserstoff. Reagiert sehr heftig mit Oxidationsmitteln.
ARBEITSPLATZGRENZWERTE
TLV: 5 ppm; (als STEL, ceiling); (ACGIH 2005).
EG Arbeitsplatz-Richtgrenzwerte: (als TWA) 2 ppm, 15.1 mg/m? (als STEL) 5 ppm, 37.8 mg/m? Hautresorption; (EU 2003).
MAK: Hautresorption; Krebserzeugend Kategorie 3B; (DFG 2006).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation, über die Haut und durch Verschlucken.
INHALATIONSGEFAHREN
Beim Verdampfen bei 20°C tritt langsam eine gesundheitsschädliche Kontamination der Luft ein; viel schneller jedoch beim Versprühen oder Dispergieren.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION:
Die Substanz reizt die Augen, die Haut und die Atemwege.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Die Flüssigkeit entfettet die Haut. Möglich sind Auswirkungen auf die Leber.
LECKAGE
Ausgelaufene Flüssigkeit möglichst in abdichtbaren Behältern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen. Verschüttetes Material in abdichtbaren Behältern sammeln., wenn in festem Zustand. NICHT in die Umwelt gelangen lassen. Persönliche Schutzausrüstung: Atemschutzfilter für organische Gase und Dämpfe.
R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R38:Reizt die Haut.
R50/53:Sehr giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
R52/53:Schädlich für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
R39/23/24/25:Giftig: ernste Gefahr irreversiblen Schadens durch Einatmen, Berührung mit der Haut und durch Verschlucken.
R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
R11:Leichtentzündlich.
S-Sätze Betriebsanweisung:
S23:Gas/Rauch/Dampf/Aerosol nicht einatmen(geeignete Bezeichnung(en) vom Hersteller anzugeben).
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S60:Dieses Produkt und sein Behälter sind als gefährlicher Abfall zu entsorgen.
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S16:Von Zündquellen fernhalten - Nicht rauchen.
Beschreibung
Trichlorobenzenes (TCBs) are synthetic chemicals that occur in three different isomeric forms. The three chlorinated cyclic aromatic isomers are 1,2,3-trichlorobenzene (1,2,3-TCB), 1,2,4-trichlorobenzene (1,2,4-TCB), and 1,3,5-trichlorobenzene (1,3,5-TCB). 1,2,4-TCB is one of the 188 chemicals designated as a hazardous air pollutant under the Clean Air Act.
Chemische Eigenschaften
1,2,4-Trichlorobenzene is a low-melting solid or liquid with a pleasant, aromatic odor. The Odor Threshold is 1.4 ppm.
Physikalische Eigenschaften
Colorless liquid with an odor similar to o-dichlorobenzene. Odor threshold concentration is 1.4 (quoted, Amoore and Hautala, 1983). Miscible with most organic solvents and oils; insoluble in water. Combustible.
Verwenden
1,2,4-Trichlorobenzene is used as a dielectric and heat transfer fluid in transformers. It acts as an intermediate, degreaser, wood preservative and solvent for dye. It is a high-temperature solvent used in gel permeation chromatography, especially for polyethylene and polypropylene. Further, it is used as a lubricant and as a synthetic transformer oil.
Definition
ChEBI: 1,2,4-trichlorobenzene is a trichlorobenzene with chloro substituents at positions 1, 2 and 4. It is a solvent in various organic chemical reactions.
Application
Trichlorobenzenes are primarily used as solvents in chemical manufacturing industries. 1,2,4-Trichlorobenzene is economically the most important isomer. It is used as a solvent in chemical reactions to dissolve oils, waxes, and resins. Furthermore, it is also used as a dye carrier. 1,2,4-Trichlorobenzene is a highly chlorinated aromatic solvent. It may be used as a solvent to prepare:
dimethylketene β-lactone dimer from tetramethyl-1,3-cyclobutanedione
salicyl-o-toluide by the reaction of phenyl salicylate and o-toluidine
Synthesis Reference(s)
Journal of the American Chemical Society, 74, p. 3890, 1952 DOI: 10.1021/ja01135a052
Allgemeine Beschreibung
Colorless liquid or white solid with a sharp chlorobenzene odor. Melting point 16.95°C (62.5°F) .
Reaktivität anzeigen
1,2,4-Trichlorobenzene can react vigorously with oxidizing materials . Yields hydrogen chloride and phosgene when heated to decomposition [USCG, 1999].
Health Hazard
Exposures 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.
Sicherheitsprofil
Poison 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.
mögliche Exposition
1,2,4-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 Fate
Biological. 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).
Versand/Shipping
UN2321 Trichlorobenzenes, liquid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
läuterung methode
Separate 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.]
Toxicity evaluation
The liver is themain target of trichlorobenzenes irrespective of the route of exposure. The mechanisms of liver toxicity induced by these chemicals have not been illustrated. It might involve intermediate arene oxides formed during initial transformation to trichlorophenols. In addition, exposure to 1,2,4-TCB induced porphyria in rats by inducing daminolevulinic acid (ALA) synthetase, a rate-limiting enzyme in the biosynthesis of heme, and also heme oxygenase, a ratelimiting enzyme in the degradation of heme synthetase, and therefore increasing heme production.
Inkompatibilitäten
Reacts violently with oxidants, acids, acid fumes; steam.
Waste disposal
Incineration, 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.

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