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Chrysene

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Chrysene Basic information
Chrysene Chemical Properties
  • Melting point:252-254 °C(lit.)
  • Boiling point:448 °C(lit.)
  • Density 1.274
  • vapor pressure 4.3 at 25 °C (de Kruif, 1980)
  • refractive index 1.7480 (estimate)
  • Flash point:-17℃
  • storage temp. 2-8°C
  • solubility <0.0001g/l
  • form neat
  • Water Solubility insoluble
  • Merck 14,2255
  • BRN 1909297
  • Henry's Law Constant1.97, 6.91, 18.8, 52.3, and 118 at 4.1, 11.0, 18.0, 25.0, and 31.0 °C, respectively (Bamford et al., 1998)
  • Stability:Stable. Combustible. Incompatible with strong oxidizing agents.
  • InChIKeyWDECIBYCCFPHNR-UHFFFAOYSA-N
  • CAS DataBase Reference218-01-9(CAS DataBase Reference)
  • IARC2B (Vol. 92) 2010
  • NIST Chemistry ReferenceChrysene(218-01-9)
  • EPA Substance Registry SystemChrysene (218-01-9)
Safety Information
MSDS
Chrysene Usage And Synthesis
  • DescriptionChrysene is a polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings. Some of its derivatives such as electroluminescent 3, 6, 9, 12-tetrasubstituted chrysenes are useful in electroluminescent applications such as being used in the organic light emitting dioxide (OLED). They are also relates to electronic devices in which the active layer includes such a chrysene composition. Chrysene is a potential carcinogen.
  • SourcesTokito, Shizuo, et al. Applied Physics Letters 77.2(2000):160-162.
    Gao, Weiying, D. T. Deibler, and V. Rostovtsev. "Chrysene derivative host materials." US, US8932733. 2015.
    Ionkin, Alex Sergey. "Tetra-substituted chrysenes for luminescent applications." US, US8115378. 2012.
    https://en.wikipedia.org/wiki/Chrysene
  • Chemical Propertiescrystalline powder
  • Chemical PropertiesChrysene is a combustible, white (when pure), red, or blue, fluorescent crystalline solid. Odorless. Chrysene 859 Polycyclic aromatic hydrocarbons (PAHs) are compounds containing multiple benzene rings and are also called polynuclear aromatic hydrocarbons
  • Physical propertiesOrthorhombic, bipyramidal plates from benzene exhibiting strong reddish-blue fluorescence under UV light
  • UsesOrganic synthesis.
  • UsesLaboratory reagent; formed during the pyrolysis of organic matter
  • Synthesis Reference(s)Tetrahedron Letters, 29, p. 3865, 1988 DOI: 10.1016/S0040-4039(00)82136-X
  • General DescriptionA crystalline solid. Denser than water and insoluble in water. The primary hazard is the threat to the environment. Immediate steps should be taken to limit spread to the environment. Toxic by ingestion. Used to make other chemicals.
  • Air & Water ReactionsInsoluble in water.
  • Reactivity ProfileVigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as Chrysene, and strong oxidizing agents. They can react exothermically with bases and with diazo compounds. Substitution at the benzene nucleus occurs by halogenation (acid catalyst), nitration, sulfonation, and the Friedel-Crafts reaction.
  • HazardPossible carcinogen.
  • Health HazardThere is very little information published onthe acute toxicity of chrysene. The oral toxicity is expected to be low. Animal studies showsufficient evidence of carcinogenicity. It produced skin cancer in animals. Subcutaneousadministration of chrysene in mice causedtumors at the site of application. Cancer-causing evidence in humans is not known. Ahistidine reversion–Ames test for mutagenicity showed positive.
  • Health HazardACUTE/CHRONIC HAZARDS: Toxic.
  • Fire HazardSome may burn but none ignite readily. Containers may explode when heated. Some may be transported hot.
  • Safety ProfileConfirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data by skin contact. Human mutation data reported. When heated to decomposition it emits acrid smoke and fumes.
  • Potential ExposureAlmost never found by itself, chrysene is found in gasoline and diesel exhaust as well as in cigarette smoke; and in coal tar; coal tar pitch; creosote. It is used in organic synthesis.
  • CarcinogenicityThe IARC has determined that there is limited evidence that chrysene is carcinogenic to experimental animals.ACGIH has classified chrysene as a confirmed animal carcinogen with unknown relevance to humans; a numerical threshold limit value (TLV) is not recommended.
  • SourceIdentified in Kuwait and South Louisiana crude oils at concentrations of 6.9 and 17.5 ppm, respectively (Pancirov and Brown, 1975). Also present in high octane gasoline (6.7 mg/kg), bitumen (1.64–5.14 ppm), gasoline exhaust (27–318 μg/m3), cigarette smoke (60 μg/1,000 cigarettes), and South Louisiana crude oil (17.5 ppm) (quoted, Verschueren, 1983). Also detected in fresh motor oil (56 mg/L), used motor oil (10.17 mg/L) (Pasquini and Monarca, 1093).
    Detected in groundwater beneath a former coal gasification plant in Seattle, WA at a concentration of 10 μg/L (ASTR, 1995). The concentration of chrysene in coal tar and the maximum concentration reported in groundwater at a mid-Atlantic coal tar site were 3,600 and 0.0063 mg/L, respectively (Mackay and Gschwend, 2001). Based on laboratory analysis of 7 coal tar samples, chrysene concentrations ranged from 620 to 5,100 ppm (EPRI, 1990). Chrysene was also detected in 9 commercially available creosote samples at concentrations ranging from 19 to 620 mg/kg (Kohler et al., 2000).
    Identified in high-temperature coal tar pitches used in roofing operations at concentrations ranging from 2,600 to 88,000 mg/kg (Arrendale and Rogers, 1981; Malaiyandi et al., 1982).
    Chrysene was detected in asphalt fumes at an average concentration of 115.67 ng/m3 (Wang et al., 2001).
    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 chrysene emitted ranged from 127.9 ng/kg at 950 °C to 1,186.0 ng/kg at 750 °C. The greatest amount of PAHs emitted were observed at 750 °C (Mastral et al., 1999).
  • Environmental FateBiological. When chrysene was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, significant biodegradation with varied adaptation rates was observed. At concentrations of 5 and 10 mg/L, 59 and 38% biodegradation, respectively, were observed after 28 d (Tabak et al., 1981).
    Soil. The reported half-lives for chrysene in a Kidman sandy loam and McLaurin sandy loam are 371 and 387 d, respectively (Park et al., 1990).
    Surface Water. In a 5-m deep surface water body, the calculated half-lives for direct photochemical transformation at 40 °N latitude, in the midsummer during midday were 13 h and 68 d with and without sediment-water partitioning, respectively (Zepp and Schlotzhauer, 1979).
    Photolytic. Based on structurally related compounds, chrysene may undergo photolysis to yield quinones (U.S. EPA, 1985) and/or hydroxy derivatives (Nielsen et al., 1983). The atmospheric half-life was estimated to range from 0.802 to 8.02 h (Atkinson, 1987). Behymer and Hites (1985) determined the effect of different substrates on the rate of photooxidation of chrysene using a rotary photoreactor. The photolytic half-lives of chrysene using silica gel, alumina, and fly ash were 100, 78, and 38 h, respectively.
  • ShippingUN3077 Environmentally Hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.
  • Purification MethodsPurify chrysene by chromatography on alumina from pet ether in a darkened room. Its solution in *C6H6 is passed through a column of decolorising charcoal, then crystallised by concentrating the eluate. It has also been purified by crystallising from *C6H6 or *C6H6/pet ether, and by zone refining. [Gorman et al. J Am Chem Soc 107 4404 1985]. It is freed from 5H-benzo[b]carbazole by dissolving it in N,N-dimethylformamide and successively adding small portions of alkali and iodomethane until the fluorescent colour of the carbazole anion no longer appears when alkali is added. The chrysene (and alkylated 5H-benzo[b]carbazole) separate on addition of water. Final purification is by crystallisation from ethylcyclohexane and/or from 2-methoxyethanol [Bender et al. Anal Chem 36 1011 1964]. It can be sublimed in a vacuum. [Beilstein 5 IV 2554.]
  • IncompatibilitiesContact with strong oxidizers may cause fire and explosion hazard
  • Waste DisposalChrysene may be destroyed by permanganate oxidation, by high-temperature incinerator with scrubbing equipment; or by microwave plasma treatment.
Chrysene Preparation Products And Raw materials
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