Acenaphthylen

Bezeichnung:Acenaphthylen

CAS-Nr208-96-8

Englisch Name:Acenaphthylene

CBNumberCB1665589

SummenformelC12H8

Molgewicht152.19

MOL-Datei208-96-8.mol

Synonyma

Acenaphthylen

Acenaphthylen physikalisch-chemischer Eigenschaften

Schmelzpunkt	78-82 °C(lit.)
Siedepunkt	280 °C(lit.)
Dichte	0.899 g/mL at 25 °C(lit.)
Dampfdruck	6.68 at 25 °C (gas saturation-HPLC/UV spectrophotometry, Sonnefeld et al., 1983)
Brechungsindex	1.6360 (estimate)
Flammpunkt	122°C
storage temp.	room temp
Löslichkeit	Soluble in ethanol, ether, and benzene (U.S. EPA, 1985)
Aggregatzustand	Solid
Farbe	Yellow
Wichte	0.899
Wasserlöslichkeit	3.93mg/L(25 ºC)
BRN	774092
Henry's Law Constant	1.14 at 25 °C (gas stripping-UV spectrophotometry, Warner et al., 1987)
Stabilität	Stable. Incompatible with oxidizing agents.
Major Application	environmental
InChI	1S/C12H8/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-8H
InChIKey	HXGDTGSAIMULJN-UHFFFAOYSA-N
SMILES	c1cc2C=Cc3cccc(c1)c23
CAS Datenbank	208-96-8(CAS DataBase Reference)
EPA chemische Informationen	Acenaphthylene (208-96-8)

Sicherheit

Kennzeichnung gefährlicher	Xn,N,F,T,Xi
R-Sätze:	22-36/37/38-67-65-50/53-38-11-39/23/24/25-23/24/25-20
S-Sätze:	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-Nr.	AB1254000
TSCA	TSCA listed
HazardClass	9
HS Code	29029090
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3
Giftige Stoffe Daten	208-96-8(Hazardous Substances Data)
Toxizität	LC₅₀ (21-d) for Folsomia fimetaria 145 mg/kg (Sverdrup et al., 2002).

Gefahreninformationscode (GHS)

Acenaphthylene Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R67:Dämpfe können Schläfrigkeit und Benommenheit verursachen.
R65:Gesundheitsschädlich: kann beim Verschlucken Lungenschäden verursachen.
R50/53:Sehr giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
R38:Reizt die Haut.
R11:Leichtentzündlich.
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.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S62:Bei Verschlucken kein Erbrechen herbeiführen. Sofort ärztlichen Rat einholen und Verpackung oder dieses Etikett vorzeigen.
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
S60:Dieses Produkt und sein Behälter sind als gefährlicher Abfall zu entsorgen.
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.
S7:Behälter dicht geschlossen halten.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Beschreibung
Acenaphthylene 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.
Chemische Eigenschaften
Acenaphthylene 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.
Physikalische Eigenschaften
Colorless to white prisms or crystalline plates from alcohol with an odor similar to coal tar or aromatic hydrocarbons.
Verwenden
Polycyclic aromatic hydrocarbons as carcinogenic
Verwenden
Acenaphthylene has been used to investigate the photodimerization of acenaphthylene in micellar and hydrogel media.
Verwenden
Acenaphthylene may be used as an analytical reference standard for the determination of the analyte in water using gas chromatography-flame ionization detection (GC-FID).
synthetische
It can be produced industrially by catalytic gas-phase dehydrogenation of acenaphthene.
Definition
ChEBI: 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.
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
Allgemeine Beschreibung
Acenaphthylene is a colorless crystalline solid. Insoluble in water. Used in dye synthesis, insecticides, fungicides, and in the manufacture of plastics.
Air & Water Reaktionen
Insoluble in water.
Reaktivität anzeigen
Vigorous 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 Hazard
Acenaphthene 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.
Health Hazard
Carcinogenic properties of this compound inanimals or humans are not known. Toxicitydata are not available.
Sicherheitsprofil
Moderately toxic by intraperitonealroute. Mutation data reported. When heated todecomposition it emits acrid smoke and irritating fumes.
mögliche Exposition
PAHs 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.
Source
Detected 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 Fate
Biological. 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).
Versand/Shipping
UN3143 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.
läuterung methode
Dissolve 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.]
Inkompatibilitäten
Keep 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
Filter für giftige stoffe
The Initial Threshold Screening Level (ITSL) for acenaphthylene is 35 μg/m3, with annual averaging time.
Waste disposal
Consult 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
Einzelnachweise
[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.

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