83-32-9 Usage
Synthesis Reference(s)
Synthetic Communications, 14, p. 1119, 1984 DOI: 10.1080/00397918408059644
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Acenaphthene is incompatible with strong oxidizing agents. Incompatible with ozone and chlorinating agents. Forms crystalline complexes with desoxycholic acid .
Health Hazard
Carcinogenicity of acenaphthene in animalsis not established. Tests for mutagenicity havegiven inconclusive results.
Health Hazard
Exposures to acenaphthene cause poisoning and include symptoms such as irritation
to the skin, eyes, mucous membranes, and upper respiratory tract. Studies on labora-
tory animals orally exposed to acenaphthene showed loss of body weight, peripheral
blood changes (unspecifi
ed), increased aminotransferase levels in blood serum, and
mild morphological damage to the liver and kidneys. In chronic exposures, acenaph-
thene is known to cause damage to the kidneys and liver. Acenaphthene is irritating to
the skin and mucous membranes of humans and animals. Oral exposure of rats to ace-
naphthene for 32 days produced peripheral blood changes, mild liver and kidney dam-
age, and pulmonary effects. However, detailed studies with acenaphthene in humans
are limited.
Fire Hazard
Flash point data for Acenaphthene are not available. Acenaphthene is probably combustible.
Safety Profile
Moderately toxic by intraperitonealroute. Mutation data reported.Incompatible with strongoxidizing agents, ozone, chlorinating agents. When heatedto decomposition it emits acrid smoke and irritating vapors.
Potential Exposure
Acenaphthene occurs naturally in coal tar and in coal tar produced during the high-temperature carbonization or coking of coal; coal tar distilling; petroleum processing; shale oil processing. It is used as an intermediate for dyes, fungicides, insecticides, herbicides, pharmaceuticals, plant growth hormones; 1,8 naphthalic acid; in the manufacture of some plastics; and has been detected in cigarette smoke and gasoline exhaust condensates; a constituent of coal tar creosote, asphalt, and diesel fuel. It has been used as an polyploidy agent.
Source
Detected in groundwater beneath a former coal gasification plant in Seattle, WA at a
concentration of 180 g/L (ASTR, 1995). Acenaphthene is present in tobacco smoke, asphalt,
combustion of aromatic fuels containing pyridine (quoted, Verschueren, 1983). Acenaphthene was
detected in asphalt fumes at an average concentration of 18.65 ng/m3 (Wang et al., 2001). Present
in diesel fuel and corresponding aqueous phase (distilled water) at concentrations of 100 to 600
mg/L and 4 to 14 g/L, respectively (Lee et al., 1992).
Thomas and Delfino (1991) equilibrated contaminant-free groundwater collected from
Gainesville, FL with individual fractions of three individual petroleum products at 24–25 °C for
24 h. The aqueous phase was analyzed for organic compounds via U.S. EPA approved test method
625. Average acenaphthene concentrations reported in water-soluble fractions of unleaded gasoline, kerosene, and diesel fuel were 1, 2, and 6 g/L, respectively.
Acenaphthene occurs naturally in coal tar. Based on laboratory analysis of 7 coal tar samples,
acenaphthene concentrations ranged from 350 to 12,000 ppm (EPRI, 1990). Detected in 1-yr aged
coal tar film and bulk coal tar at concentrations of 5,800 and 5,900 mg/kg, respectively (Nelson et
al., 1996). A high-temperature coal tar contained acenaphthene at an average concentration of 1.05
wt % (McNeil, 1983). Lee et al. (1992a) equilibrated 8 coal tars with distilled water at 25 °C. The
maximum concentration of acenaphthene observed in the aqueous phase was 0.3 mg/L.
Nine commercially available creosote samples contained acenaphthene at concentrations
ranging from 9,500 to 110,000 mg/kg (Kohler et al., 2000).
Acenaphthene was detected in a diesel-powered medium duty truck exhaust at an emission rate
of 19.3 μg/km (Schauer et al., 1999) and is a component in cigarette smoke. Acenaphthene was
detected in soot generated from underventilated combustion of natural gas doped with 3 mole %
toluene (Tolocka and Miller, 1995).
Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without
catalytic converters were 6.55 and 177 μg/km, respectively (Schauer et al., 2002).
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 acenaphthene were 2.02 mg/kg of pine burned, 1.15 mg/kg of oak burned, and 0.893
mg/kg of eucalyptus burned.
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 acenaphthene emitted ranged from 1,272.4 ng/kg at 650 °C to 6,800.0 ng/kg at 750 °C.
The greatest amount of PAHs emitted was observed at 750 °C (Mastral et al., 1999).
Typical concentration of acenaphthene in a heavy pyrolysis oil is 1.6 wt % (Chevron Phillips,
May 2003).
Environmental fate
Biological. When acenaphthene 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, 95 and 100% biodegradation, respectively, were
observed after 7 d (Tabak et al., 1981). A Beijerinckia sp. and a mutant strain (Beijerinckia sp.
strain B8/36) cooxidized acenaphthene to the following metabolites: 1,2-acenaphthenediol,
acenaphthene-quinone, and a compound tentatively identified as 1,2-dihydroxyacenaphthylene
(Schocken and Gibson, 1984). The fungus Cunninghamella elegans ATCC 36112 degraded
approximately 64% acenaphthene added within 72 h of incubation. Metabolites identified and
their respective yields were 6-hydroxyacenaphthenone (24.8%), 1,2-acenaphthenedione (19.9%),
trans-1,2-dihydroxyacenaphthene (10.3%), 1,5-dihydroxyacenaphthene (2.7%), 1-acenaphthenol
(2.4%), 1-acenaphthenone (2.1%), and cis-1,2-dihydroxyacenaphthene (1.8%) (Pothuluri et al.,
1992). A recombinant strain of Pseudomonas aeruginosa PAO1(pRE695) degraded acenaphthene
via mono-oxygenation to 1-acenaphthenol which was converted to 1-acenaphthenone and cis- and
trans-1,2-dihydroxyacenaphthenes. The two latter compounds were subsequently converted to 1,2-
acenaphthoquinone which oxidized to naphthalene-1,8-dicarboxylic acid (Selifonov et al., 1996).
In a soil-water system, acenaphthene did not biodegrade under anaerobic conditions. Under
denitrification conditions, acenaphthene (water concentration 400 μg/L) degraded to nondetectable
levels in 40 d. In both studies, the acclimation period was approximately 2 d (Mihelcic
and Luthy, 1988).
Photolytic. Fukuda et al. (1988) studied the photodegradation of acenaphthene and alkylated
naphthalenes in distilled water and artificial seawater using a high-pressure mercury lamp. Based
upon a rate constant of 0.23/h, the photolytic half-life of acenaphthene in water is 3 h. Behymer
and Hites (1985) determined the effect of different substrates on the rate of photooxidation of
acenaphthene using a rotary photoreactor equipped with a 450-W medium pressure mercury lamp
(λ = 300–410 nm). The photolytic half-lives of acenaphthene absorbed onto silica gel, alumina,
and fly ash were 2.0, 2.2, and 44 h, respectively. The estimated photooxidation half-life of
acenaphthene in the atmosphere via OH radicals is 0.879 to 8.79 h (Atkinson, 1987).
Chemical/Physical. Ozonation in water at 60 °C produced 7-formyl-1-indanone, 1-indanone, 7-
hydroxy-1-indanone, 1-indanone-7-carboxylic acid, indane-1,7-dicarboxylic acid, and indane-1-
formyl-7-carboxylic acid (Chen et al., 1979). Wet oxidation of acenaphthene at 320 °C yielded
formic and acetic acids (Randall and Knopp, 1980). The measured rate constant for the gas-phase
reaction of acenaphthene with OH radicals is 8.0 x 10-11 cm3/molecule·sec (Reisen and Arey,
2002).
Purification Methods
It has also been purified by chromatography from CCl4 on alumina with *benzene as eluent [McLaughlin & Zainal J Chem Soc 2485 1960]. [Beilstein 5 IV 1834.]
Incompatibilities
Ozone and strong oxidizing agents, including perchlorates, chlorine, fluorine, and bromine
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. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office. Incineration or permanganate oxidation
Check Digit Verification of cas no
The CAS Registry Mumber 83-32-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 3 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 83-32:
(4*8)+(3*3)+(2*3)+(1*2)=49
49 % 10 = 9
So 83-32-9 is a valid CAS Registry Number.
InChI:InChI=1/C10H8.C2H4/c1-2-6-10-8-4-3-7-9(10)5-1;1-2/h1-8H;1-2H2
83-32-9Relevant articles and documents
Time-delayed, two-color excimer laser photolysis of 1,8-bis(substituted-methyl)naphthalenes with group 16 atom leaving groups
Ouchi, Akihiko,Koga, Yoshinori
, p. 8999 - 9002 (1995)
Time-delayed, two-color photolysis of 1,8-bis(phenoxymethyl)-(1a), 1,8-bis(phenylthiomethyl)-(1b), and 1,8-bis(phenylselenomethyl)-naphthalene (1c) was conducted by successive irradiation of XeCl (308 nm) and XeF (351 nm) excimer lasers. The yield of the two-photon product, acenaphthene 3, was strongly dependent on the delay time and showed two maxima at different delay times.
Laser-jet Photolysis of 1,8-Bis(substituted-methyl)naphthalenes: the Effect of Heteroatom Leaving Groups on the Two-photon C-C Bond Formation
Ouchi, Akihiko,Adam, Waldemar
, p. 628 - 629 (1993)
The formation of acenaphthene 4 by laser-jet photolysis of 1,8-bis(phenoxymethyl)- (1a), 1,8-bis(phenylthiomethyl)- (1b) and 1,8-bis(phenylselenomethyl)-naphthalene (1c) strongly depends on the hetroatom of the leaving group; the increasing order of naphthalene consumption was 1c ca. 1b > 1a, whereas that for the formation of 4 was 1c > 1a > 1b.
Time-delayed, Two-color Excimer Laser Photolysis of 1,8-Bis(halomethyl)naphthalenes
Ouchi, Akihiko,Yabe, Akira
, p. 945 - 946 (1995)
Time-delayed two-color photolysis of 1,8-bis(bromomethyl)-naphthalene and 1,8-bis(chloromethyl)naphthalene was conducted by successive irradiation of XeCl (308 nm) and XeF (351 nm) excimer lasers.Increase in the yield of the two-photon product, acenaphthene, strongly depended on the delay time of the two lasers and showed two maxima at the delay times of 0-30 ns and 0.2-0.5 μs.
Reactivity of the 5-hydroacenaphthylene anion towards electrophiles
Van Loo, Marcia E.,Lugtenburg, Johan,Cornelisse, Jan
, p. 1907 - 1914 (1998)
The dianion of acenaphthylene can be converted into the 5-hydroanion by protonation with one equivalent of methanol. Subsequent reaction with electrophiles such as allyl bromide and propargyl bromide occurs selectively at position 1, resulting in the formation of the novel 1-allylacenaphthene and 1-propargylacenaphthene. In addition to what was observed in the case of methyl iodide, the hitherto unknown 1,1-dialkylated acenaphthene derivatives are formed as minor products; probably the lower reactivity of the unsaturated bromides is responsible for this side reaction. From the products of the reactions with 3,3-dimethylallyl bromide and (bromomethyl)cyclopropane the mechanism was found to be SN2. Reaction of the hydroanion with benzyl bromide takes place at position 1 as well as at position 2a. The reactivity of carbon 2a towards the soft electrophile benzyl bromide is attributed to the high HOMO coefficient at this position.
A laser-specific C-C bond formation of bichromophoric compounds
Ouchi, Akihiko,Yabe, Akira
, p. 1727 - 1730 (1990)
The formation of acenaphthene from less photoreactive 1,8-bis(bromomethyl)naphthalene and 1,8-bis(chloromethyl)naphthalene by high-fluence KrF excimer laser irradiation was observed; the result contrasts with failed attempts using a low-pressure mercury lamp.
Highly efficient C - C bond formation in the two-photon chemistry of 1,8-bis(substituted-methyl)naphthalenes by direct excitation of photoactive leaving groups
Ouchi, Akihiko,Yabe, Akira,Adam, Waldemar
, p. 6309 - 6312 (1994)
High efficiency in the two-photon intramolecular C - C bond formation to the two-photon product acenaphthene (4), obtained in a maximum yield of 72%, was achieved by direct activation of two separate leaving groups of 1,8-bis(phenoxymethyl)- (1a), 1,8-bis(phenylthiomethyl)- (1b), and 1,8-bis(phenylselenomethyl)-naphthalenes (1c) during KrF excimer laser (248 nm) and of 1,8-bis(4-benzoylphenoxymethyl)- (1d), 1,8-bis(3-benzoylphenoxymethyl)- (1e), and 1,8-bis(2-naphthoxymethyl)naphthalenes (1f) during XeF excimer laser (351 nm) photolyses.
A remarkable wavelength dependence on the laser-induced two-photon C-C bond formation
Ouchi,Yabe
, p. 5359 - 5362 (1992)
Two-photon intramolecular C-C bond formation of 1,8-bis(bromomethyl)naphthalene and 1,8-bis(chloromethyl)naphthalene by high fluence excimer laser irradiations showed a considerable wavelength dependence on the conversion, the efficiency, and the yield of the product; the results are interpreted by the selective excitation of the substrates.
Two-photon chemistry of 1,8-bis(bromomethyl)naphthalene in the laser-jet: Generation of acenaphthene by intramolecular C - C bond formation
Adam, Waldemar,Ouchi, Akihiko
, p. 1875 - 1878 (1992)
Argon ion laser-induced photolysis of 1,8-bis(bromomethyl)naphthalene (1) in the laser-jet with benzophenone as sensitizer gave ca. 8% (61% conversion) of acenaphthene (4) through cyclization of the intermediary non-Kekule diradical 1,8-dimethylenenaphthalene; in this two-photon process the first photon (333-nm) consumes 1, whereas the second photon (351 and 364 nm) forms 2, both steps are sensitized by benzophenone.
Two-photon laser-induced reaction of 1,8-bis(halomethyl)naphthalenes from different excited states and transient targeting of its intermediate by time-delayed, two-color photolysis and argon ion laser-jet photolysis techniques
Ouchi, Akihiko,Koga, Yoshinori,Adam, Waldemar
, p. 592 - 599 (1997)
Two-photon chemistry of 1,8-bis(bromomethyl)naphthalene (1a) and 1,8-bis(chloromethyl)naphthalene (1b) was studied by (a) laser photolysis with use of XeCl (308 nm), KrF (248 nm), and ArF (193 nm) excimer lasers, (b) time-delayed, two-color photolysis with use of XeCl and XeF (351 nm) lasers, and (c) argon ion laser-jet (333, 351, and 364 nm) photolysis by both direct and benzophenone sensitization. The reaction proceeds through an intermediate monoradical 2, which is generated by a one-photon process, followed by additional photolysis to the two-photon product acenaphthene (4). On excitation of substrate 1 to its S1 state, monoradical 2 is formed directly from the S1 state and subsequently from the T1 state through intersystem crossing, alternatively on benzophenone sensitization. Upper excited states, namely S2 and S3, of 1 are proposed in the KrF and AsF excimer laser irradiation, generating intermediate 2 through fast fragmentation of the T(σ*) state. Transient targeting of intermediate 2 by time-delayed, two-color photolysis and argon ion laser-jet photolysis increases considerably the yield of the two-photon product 4.
Synthesis of Decorated Carbon Structures with Encapsulated Components by Low-Voltage Electric Discharge Treatment
Bodrikov, I. V.,Pryakhina, V. I.,Titov, D. Yu.,Titov, E. Yu.,Vorotyntsev, A. V.
, p. 60 - 69 (2022/03/17)
Abstract: Polycondensation of complexes of chloromethanes with triphenylphosphine by the action of low-voltage electric discharges in the liquid phase gives nanosized solid products. The elemental composition involving the generation of element distribution maps (scanning electron microscopy–energy dispersive X?ray spectroscopy mapping) and the component composition (by direct evolved gas analysis–mass spectrometry) of the solid products have been studied. The elemental and component compositions of the result-ing structures vary widely depending on the chlorine content in the substrate and on the amount of triphenylphosphine taken. Thermal desorption analysis revealed abnormal behavior of HCl and benzene present in the solid products. In thermal desorption spectra, these components appear at an uncharacteristically high temperature. The observed anomaly in the behavior of HCl is due to HCl binding into a complex of the solid anion HCI-2 with triphenyl(chloromethyl)phosphonium chloride, which requires a relatively high temperature (up to 800 K) to decompose. The abnormal behavior of benzene is associated with its encapsulated state in nanostructures. The appearance of benzene begins at 650 K and continues up to temperatures above 1300?K.
