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Acenaphthylene

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CAS:208-96-8
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Acenaphthylene Basic information
Product Name:Acenaphthylene
Synonyms:Acenaphthylene 100mg [208-96-8];cyclopenta(de)naphthalene;acenaphthylene anion radical;1,2-dihydroacenaphthylene-1,2-diide;ACENAPHTHYLENE;acenaphthylene,industrial;acenaphthylene solution;Acenaphthylene, 80%,tech
CAS:208-96-8
MF:C12H8
MW:152.19
EINECS:205-917-1
Product Categories:Aromatics;Mutagenesis Research Chemicals;Building Blocks;Chemical Synthesis;Organic Building Blocks;Industrial/Fine Chemicals;AA to ALAnalytical Standards;A;A-BAlphabetic;Alpha Sort;AromaticsChemical Class;Chemical Class;Hydrocarbons;NeatsAnalytical Standards;PAHs;Volatiles/ Semivolatiles;Arenes;Building Blocks;Organic Building Blocks;Naphthalenes;AA to AL;Alphabetic;PAH
Mol File:208-96-8.mol
Acenaphthylene Structure
Acenaphthylene Chemical Properties
Melting point 78-82 °C(lit.)
Boiling point 280 °C(lit.)
density 0.899 g/mL at 25 °C(lit.)
vapor pressure 6.68 at 25 °C (gas saturation-HPLC/UV spectrophotometry, Sonnefeld et al., 1983)
refractive index 1.6360 (estimate)
Fp 122°C
storage temp. room temp
solubility Soluble in ethanol, ether, and benzene (U.S. EPA, 1985)
form Solid
color Yellow
Specific Gravity0.899
Water Solubility 3.93mg/L(25 ºC)
BRN 774092
Henry's Law Constant1.14 at 25 °C (gas stripping-UV spectrophotometry, Warner et al., 1987)
Stability:Stable. Incompatible with oxidizing agents.
InChIKeyHXGDTGSAIMULJN-UHFFFAOYSA-N
CAS DataBase Reference208-96-8(CAS DataBase Reference)
EPA Substance Registry SystemAcenaphthylene (208-96-8)
Safety Information
Hazard Codes Xn,N,F,T,Xi
Risk Statements 22-36/37/38-67-65-50/53-38-11-39/23/24/25-23/24/25-20
Safety Statements 26-36/37/39-62-61-60-45-36/37-16-7-37/39-33-25-9
RIDADR UN 1145 3/PG 2
WGK Germany 3
RTECS AB1254000
TSCA Yes
HazardClass 9
HS Code 29029090
Hazardous Substances Data208-96-8(Hazardous Substances Data)
ToxicityLC50 (21-d) for Folsomia fimetaria 145 mg/kg (Sverdrup et al., 2002).
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
Acenaphthylene Usage And Synthesis
DescriptionAcenaphthylene is a polycyclic aromatic hydrocarbon (PAH) consisting of three fused aromatic rings. It is used in the production of plastics and serves as an intermediate in the manufacture of dyes, soaps, pigments, pharmaceuticals, insecticides, fungicides, herbicides, and plant growth regulators. It is also a precursor to naphthalic acids, naphthalic anhydride (which is used in pigment production), and can be utilized in the synthesis of resins.
The largest emissions of PAHs originate from the incomplete combustion of organic matter during industrial processes and other human activities. Major sources include:
(a) the processing of coal, crude oil, and natural gas;
(b) coking, coal conversion, petroleum refining, and the production of carbon black, creosote, coal tar, and bitumen;
(c) aluminum, iron, and steel production in plants and foundries;
(d) heating in power plants and households, as well as cooking;
(e) combustion of waste;
(f) motor vehicle emissions; 
(g) environmental tobacco smoke.
Chemical PropertiesAcenaphthylene is a flaky yellow crystalline powder that forms prismatic or plate-like crystals. It is freely soluble in organic solvents such as ethanol, methanol, propanol, diethyl ether, petroleum ether, and benzene, but insoluble in water. Additionally, it polymerizes in the presence of strong acids.
Physical propertiesColorless to white prisms or crystalline plates from alcohol with an odor similar to coal tar or aromatic hydrocarbons.
UsesPolycyclic aromatic hydrocarbons as carcinogenic
UsesAcenaphthylene may be used as an analytical reference standard for the determination of the analyte in water using ?gas chromatography-flame ionization detection (GC-FID).
UsesAcenaphthylene has been used to investigate the photodimerization of acenaphthylene in micellar and hydrogel media.
DefinitionChEBI: Acenaphthylene is a ortho- and peri-fused tricyclic hydrocarbon that occurs in coal tar. It is an ortho- and peri-fused polycyclic arene, a member of acenaphthylenes and an ortho- and peri-fused tricyclic hydrocarbon.
PreparationIt can be produced industrially by catalytic gas-phase dehydrogenation of acenaphthene.
Synthesis Reference(s)Journal of the American Chemical Society, 69, p. 1388, 1947 DOI: 10.1021/ja01198a044
The Journal of Organic Chemistry, 61, p. 324, 1996 DOI: 10.1021/jo951613a
General DescriptionAcenaphthylene is a colorless crystalline solid. Insoluble in water. Used in dye synthesis, insecticides, fungicides, and in the manufacture of plastics.
Air & Water ReactionsInsoluble in water.
Reactivity ProfileVigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as ACENAPHTHYLENE, 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.
Health HazardCarcinogenic properties of this compound inanimals or humans are not known. Toxicitydata are not available.
Health HazardAcenaphthene is irritating to the skin and mucous membranes of rabbits. Subchronic oral administration of acenaphthene adversely affected the kidneys, liver, blood, reproductive system, and lungs in experimental animals. In rats, prolonged inhalation of low doses caused pulmonary effects such as bronchitis, pneumonia, and desquamation of the bronchial and alveolar epithelium.
Safety ProfileModerately toxic by intraperitonealroute. Mutation data reported. When heated todecomposition it emits acrid smoke and irritating fumes.
Potential ExposurePAHs are compounds containing multiple benzene rings and are also called polynuclear aromatic hydrocarbons. Acenaphthylene is an aromatic hydrocarbon used in coal tar processing, as a dye intermediate; making insecticides, fungicides, plastics.
SourceDetected in groundwater at a former coal gasification plant in Seattle, WA at concentrations ranging from nondetect (method detection limit 5 μg/L) to 250 μg/L (ASTR, 1995). Based on laboratory analysis of 7 coal tar samples, acenaphthylene concentrations ranged from 260 to 18,000 ppm (EPRI, 1990). Lee et al. (1992a) equilibrated 8 coal tars with distilled water at 25 °C. The maximum concentration of acenaphthylene observed in the aqueous phase was 0.5 mg/L.
Acenaphthylene was detected in asphalt fumes at an average concentration of 6.93 ng/m3 (Wang et al., 2001).
Detected in a distilled water-soluble fraction of used motor oil at concentrations ranging from 4.5 to 4.6 μg/L (Chen et al., 1994).
Acenaphthylene was detected in a diesel-powered medium duty truck exhaust at an emission rate of 70.1 μg/km (Schauer et al., 1999). Acenaphthylene was also detected in soot generated from underventilated combustion of natural gas doped with toluene (3 mole %) (Tolocka and Miller, 1995).
Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were 37.0 and 2,180 μg/km, respectively (Schauer et al., 2002). Nine commercially available creosote samples contained acenaphthylene at concentrations ranging from 7 to 3,700 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 gas-phase emission rates of acenaphthylene were 18.6 mg/kg of pine burned, 10.8 mg/kg of oak burned, and 9.99 mg/kg of eucalyptus burned.
Environmental fateBiological. When acenaphthylene was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, significant biodegradation with rapid adaptation was observed. At concentrations of 5 and 10 mg/L, 100 and 94% biodegradation, respectively, were observed after 7 d (Tabak et al., 1981). A Beijerinckia sp. and a mutant strain were able to cooxidize acenaphthylene to the following metabolites: acenaphthenequinone and a compound tentatively identified as 1,2-dihydroxyacenaphthylene. When acenaphthylene was incubated with a mutant strain (Beijerinckia sp. strain B8/36) one metabolite formed which was tentatively identified as cis-1,2-acenaphthenediol (Schocken and Gibson, 1984). This compound also formed when acenaphthylene was deoxygenated by a recombinant strain of Pseudomonas aeruginosa PAO1(pRE695) (Selifonov et al., 1996).
Bossert and Bartha (1986) reported that acenaphthylene in a Nixon sandy loam soil (1 g/kg) completely disappeared in <4 months. They concluded volatilization was more important than biodegradation in the disappearance of acenaphthylene from soil.
Ozonation in water at 60 °C produced 1,8-naphthalene dialdehyde, 1,8- naphthalene anhydride, 1,2-epoxyacenaphthylene, 1-naphthoic acid, and 1,8-naphthaldehydic acid (Calvert and Pitts, 1966).
ShippingUN3143 Dye intermediates, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous material, Hazard, Technical Name Required. UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.
Purification MethodsDissolve acenaphthylene in warm redistilled MeOH, filter through a sintered glass funnel and cool to -78o to precipitate the material as yellow plates [Dainton et al. Trans Faraday Soc 56 1784 1960]. Alternatively it can be sublimed in vacuo. [Beilstein 5 H 625, 5 IV 2138.]
IncompatibilitiesKeep away from ozone and strong oxidizing agents. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides
Toxics Screening LevelThe Initial Threshold Screening Level (ITSL) for acenaphthylene is 35 μg/m3, with annual averaging time.
Waste DisposalConsult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Product residues and sorbent media may be packaged in epoxy-lined drums, then destroyed by incineration, permanganate oxidation or microwave plasma treatment. The United States Environmental Protection Agency has investigated chemical precipitation for wastewater treatment
References[1] Schmidt R et al; Hydrocarbons. Ullmann's Encyclopedia of Industrial Chemistry 7th ed. (1999-2016). NY, NY: John Wiley & Sons. Online Posting Date: November 24, 2014
[2] YUXUAN DAI . Photodegradation of acenaphthylene over plasmonic Ag/Ag3PO4 nanopolyhedrons synthesized via in-situ reduction[J]. Applied Surface Science, 2022, 572: Article 151421. DOI:10.1016/j.apsusc.2021.151421.
Tag:Acenaphthylene(208-96-8) Related Product Information
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