General Description
Colorless crystals or white crystalline solid.
Reactivity Profile
BENZO(E)PYRENE(192-97-2) may be sensitive to prolonged exposure to light.
Air & Water Reactions
Insoluble in water.
Fire Hazard
Flash point data for this compound are not available. BENZO(E)PYRENE is probably combustible.
Chemical Properties
yellow to yellow-green crystalline powder
Physical properties
Crystalline, solid, prisms, or plates. Benzo[e]pyrene is sensitive to ultraviolet light and may
degrade into diones.
Uses
Used for studies of immune suppressive activity of bezo[e]Pyrene on antibody response to DNP-Ficoll and sheep erythrocytes and "dispersive liquid -liquid micro extraction” technique by extracting organic compounds from water samples.
Definition
ChEBI: An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings. It is listed as a Group 3 carcinogen by the IARC.
Health Hazard
There is very little information available onits toxicity. The oral toxicity is expected to below. Its carcinogenic potential is lower thanthat of benz[a]pyrene. Animal studies gaveinconclusive results. Oral administration mayproduce tumors in the stomach. However, theevidence of carcinogenicity of this compoundin animals is inadequate. Benz[e]pyrene isa mutagen, testing positive to the histidinereversion–Ames test and in vitro unscheduled DNA synthesis (UDS)–human fibroblast.
Safety Profile
For occupational chemicalanalysis use NIOSH: Polynuclear Aromatic Hydrocarbons(HPLC), 5506; (GC), 5515.
Source
The concentration of benzo[e]pyrene in coal tar and the maximum concentration reported
in groundwater at a mid-Atlantic coal tar site were 3,700 and 0.0034 mg/L, respectively (Mackay
and Gschwend, 2001). Detected in 8 diesel fuels at concentrations ranging from 0.047 to 2.1 mg/L
with a mean value of 0.113 mg/L (Westerholm and Li, 1994). Identified in Kuwait and South
Louisiana crude oils at concentrations of 0.5 and 2.5 ppm, respectively (Pancirov and Brown,
1975).
Benzo[e]pyrene is produced from the combustion of tobacco and petroleum fuels. It also occurs
in low octane gasoline (0.18–0.87 mg/kg), high octane gasoline (0.45–1.82 mg/kg), used motor oil
(92.2–278.4 mg/kg), asphalt (≤0.0052 wt %), coal tar pitch (≤0.70 wt %), cigarette smoke (3
μg/1,000 cigarettes), and gasoline exhaust (quoted, Verschueren, 1983). Lehmann et al. (1984)
reported a benzo[e]pyrene concentration of 0.02 mg/g in a commercial anthracene oil.
Schauer et al. (2001) measured organic compound emission rates for volatile organic
compounds, gas-phase semi-volatile organic compounds, and particle phase organic compounds
from the residential (fireplace) combustion of pine, oak, and eucalyptus. The particle-phase
emission rates of benzo[e]pyrene were 0.459 mg/kg of pine burned, 0.231 mg/kg of oak burned,
and 0.212 mg/kg of eucalyptus burned.
Particle-phase tailpipe emission rates from gasoline-powered automobiles with and without
catalytic converters were 0.015 and 38.2 μg/km, respectively (Schauer et al., 2002).
Environmental Fate
Photolytic. Schwarz and Wasik (1976) reported a fluorescence quantum yield of ≈ 0.3 for
benzo[e]pyrene in water.
Chemical/Physical. Benzo[e]pyrene will not hydrolyze because it has no hydrolyzable
functional group.
Purification Methods
Purify it by passage through an Al2O3 column (Woelm, basic, activity I) and elute with *C6H6 and recrystallise from 2 volumes of EtOH/*C6H6 (4:1). It forms colourless or light yellow prisms or needles. [Campbell J Chem Soc 3659 1954, Buchta & Kr.ger Justus Liebigs Ann Chem 705 190 1967.] The 1,3,5-trinitrobenzene complex has m 253-254o (orange needles from EtOH), the picrate prepared by mixing 20mg in 1mL of *C6H6 with 20mg of picric acid in 2mL *C6H6, collecting the deep red crystals, and recrystallising from *C6H6 has m 228-229o [NMR: Cobb & Memory J Chem Phys 47 2020 1967]. [Beilstein 5 III 2520, 5 I V 2689.] CARCINOGEN.
