Benzo[k]fluoranthene

Description

Benzo(k)fluoranthene is primarily found in gasoline exhaust, cigarette smoke, coal tar, coal and oil combustion emissions, lubricating oils, used motor oils and crude oils. Synonyms for benzo(k)fluoranthene (BkF) include 8,9-benzfluoranthene, 8,9-benzofluoranthene, 1 1.12-benzofiuoranthene, 2,3,1,8-binaphthylene and dibenzo(bjk)fluorene. Its molecular weight is 252.32 and molecular formula C20H12. It is characterized by four benzene rings in various configurations containing only carbon and hydrogen atoms. It was absorbed through the skin, lungs, and gastrointestinal tract. In industrial processes it is considered to be environmental pollutants.

Clinical Trial

B(k)F is a weak carcinogen in mice and is also a weak tumor initiator. It is very much weaker than benzo(a)pyrene (BP). The observations regarding systemic tumors following topical application of these carcinogens to mice is of great importance. All too frequently, a dermal carcinogenicity study concentrates on skin tumors and no others. Thus, it is relatively unusual to have systemic tumors investigated. The fact that there was no difference in the level of systemic tumors in all groups, including the potent mouse carcinogen BP, would indicate that the level of systemic absorption through the skin was not significant.

Health Toxicity

B(k)F could penetrate the skin of some animals, especially mice, and remain present for a number of hours. The metabolism of B(k)F appears to follow a route leading to the predominant formation of its 5-hydroxy derivative. The further metabolism of this phenolic dihydrodiol to 5,9,10,trihydroxy-l1, 12-epoxy-9,10,11,12-tetrahydro- benzo(k)fluoranthene has been linked to the genotoxic effect of B(k)F in mouse skin. Care was taken to avoid contact with the head, axillae, and genital areas.

Chemical Properties

yellow crystals

Uses

Benzo[k]fluoranthene is used as an optical sensor for nitro-aromatic compounds due to fluorescence quenching of the molecule. It is also a carcinogen and mutagen.

Definition

ChEBI: Benzo[k]fluoranthene is a member of naphthalenes.

General Description

Pale yellow needles or yellow crystalline solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

BENZO[K]FLUORANTHENE can react with strong oxidizing agents. May react with electrophiles, peroxides, nitrogen oxides and sulfur oxides

Hazard

Possible carcinogen.

Health Hazard

Benzo[k]fluoranthene caused lungs and skincancers in animals. It produced tumors atthe site of application. Its carcinogenicity inhumans is not known.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition BENZO(K)FLUORANTHENE emits acrid smoke and irritating fumes.

Fire Hazard

Flash point data for BENZO(K)FLUORANTHENE are not available; however, BENZO(K)FLUORANTHENE is probably combustible.

Safety Profile

Confirmed carcinogen withexperimental tumorigenic data. Mutation data reported.When heated to decomposition it emits acrid smoke andirritating fumes.

Carcinogenicity

Benzo[k]fluoranthene wastested for carcinogenicity by dermal application in mice in one study, intraperitoneal injection into newborn mice in one study, and intrapulmonary implantation into rats in one study. Benzo[k]fluoranthene exhibited a significant carcinogenic activity in the dermal and intrapulmonary assays.

Source

Benzo[b]fluoranthene and benzo[k]fluoranthene were detected in 8 diesel fuels at concentrations ranging from 0.0027 to 3.1 mg/L with a mean value of 0.266 mg/L (Westerholm and Li, 1994). Also present in gasoline (9 μg/L), bitumen (34–1,140 μg/L), crude oil (<1 ppm) (quoted, Verschueren, 1983), and coal (32.5 g/kg) (Lao et al., 1975).
Based on laboratory analysis of 7 coal tar samples, benzo[k]fluoranthene concentrations ranged from 350 to 3,000 ppm (EPRI, 1990). Identified in high-temperature coal tar pitches used in roofing operations at concentrations ranging from 1,670 to 4,500 mg/kg (Malaiyandi et al., 1982).
Nine commercially available creosote samples contained benzo[k]fluoranthene at concentrations ranging from 2 to 67 mg/kg (Kohler et al., 2000).
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[k]fluoranthene were 0.671 mg/kg of pine burned, 0.303 mg/kg of oak burned, and 0.286 mg/kg of eucalyptus burned.
California Phase II reformulated gasoline contained benzo[k]fluoranthene at a concentration of 280 μg/kg. Particle-phase tailpipe emission rate from a noncatalyst-equipped gasoline-powered automobile was 32.7 μg/km (Schauer et al., 2002).
Under atmospheric conditions, a low rank coal (0.5–1 mm particle size) from Spain was burned in a fluidized bed reactor at seven different temperatures (50 °C increments) beginning at 650 °C. The combustion experiment was also conducted at different amounts of excess oxygen (5 to 40%) and different flow rates (700 to 1,100 L/h). At 20% excess oxygen and a flow rate of 860 L/h, the amount of benzo[k]fluoranthene emitted ranged from 0 ng/kg at three temperatures (650, 750, and 950 °C) to 180.5 ng/kg at 850 °C. The greatest amount of PAHs emitted were observed at 750 °C (Mastral et al., 1999).

Environmental Fate

Soil. Based on aerobic soil die-away test data, the half-life in soil ranged from 910 d to 5.86 yr (Bossert et al., 1984).
Photolytic. The atmospheric half-life was estimated to range from 1.1 to 11 h (Atkinson, 1987). Chemical/Physical. Benzo[k]fluoranthene will not hydrolyze because it has no hydrolyzable functional group (Kollig, 1995).