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EC / List no.: 201-469-6
CAS no.: 83-32-9
Mol. formula: C12H10
Acenaphthene is a polycyclic aromatic hydrocarbon (PAH) consisting of naphthalene with an ethylene bridge connecting positions 1 and 8. Acenaphthene is a colourless solid. Coal tar consists of about 0.3% of this compound.
Production and reactions
Acenaphthene was prepared the first time from coal tar by Marcellin Berthelot.
Later Berthelot and Bardy synthesized the compound by cyclization of α-ethylnaphthalene.
Industrially, it is still obtained from coal tar together with its derivative acenaphthylene (and many other compounds).
Like other arenes, acenaphthene forms complexes with low valent metal centers.
One example is (η6-acenaphthene)Mn(CO)3]+.
Uses:
Acenaphthene is used on a large scale to prepare naphthalene dicarboxylic anhydride, which is a precursor to dyes and optical brighteners.
Naphthalene dicarboxylic anhydride is the precursor to perylenetetracarboxylic dianhydride, precursor to several commercial pigments and dyes.
Description
Acenaphthene is a tricyclic aromatic hydrocarbon and crystalline solid at ambient temperature.
Acenaphthene does not dissolve in water but is soluble in many organic solvents.
Acenaphthene is a component of crude oil and a product of combustion.
Acenaphthene occurs in coal tar produced during the high-temperature carbonisation or coking of coal.
Acenaphthene is used as a dye intermediate in the manufacture of some plastics and as an insecticide and fungicide.
Acenaphthene is a component of crude oil and a product of combustion which may be produced and released to the environment during natural fires.
Emissions from petroleum refining, coal tar distillation, coal combustion, and diesel-fuelled engines are major contributors of acenaphthene to the environment.
Acenaphthene is an environmental pollutant and has been detected in cigarette smoke, automobile exhausts, and urban air, in effluents from petrochemical, pesticide, and wood preservative industries, and in soils, groundwater, and surface waters at hazardous waste sites.
This compound is one among a number of polycyclic aromatic hydrocarbons (PAHs) on U.S. EPA’s (Environmental Protection Agency) priority pollutant list.
Chemical Properties
Acenaphthene is a tricyclic aromatic hydrocarbon, crystalline solid at ambient tempera- ture.
Acenaphthene does not dissolve in water, but is soluble in many organic solvents.
Acenaphthene occurs in coal tar produced during high temperature carbonization or cok- ing of coal.
Acenaphthene is used as a dye intermediate in the manufacture of some plastics and as an insecticide and fungicide.
Acenaphthene is a component of crude oil and a product of combustion that may be produced and released into the environment during natural fi res.
Emissions from petroleum refi ning, coal tar distillation, coal combustion, and diesel- fueled engines are major contributors of acenaphthene to the environment.
Acenaphthene is an environmental pollutant and has been detected in cigarette smoke, automobile exhausts, and urban air, in effl uents from petrochemical, pesticide, and wood preservative industries, and in soils, groundwater, and surface waters at hazardous waste sites.
This compound is one of a number of polycyclic aromatic hydrocarbons on the US EPA’s prior- ity pollutant list.
Acenaphthene is a white combustible, crystalline solid.
PAHs are compounds containing multiple benzene rings and are also called polynuclear aromatic hydrocarbons
white or pale yellow crystalline powder
Physical properties
White crystalline solid or orthorhombic bipyramidal needles from alcohol.
Coal tar-like odor.
The lowest odor threshold concentration in water that may result in rejection of contaminated water ranged from 0.02 to 0.22 ppm.
In Wisconsin, the taste and odor threshold concentration in water that is nontoxic to humans is 20 μg/L.
Uses:
Acenaphthene occurs in petroleum bottoms and is used as a dye intermediate, insecticide, and fungicide and in manufacturing plastics.
Polycyclic aromatic hydrocarbons as carcinogenic
Dye intermediate, manufacture of plastics, insecticide, fungicide.
Definition
ChEBI: A polycyclic aromatic hydrocarbon derived from naphthalene by the addition of an ethylene bridge connecting C-1 and C-8.
A colorless crystalline derivative of naphthalene, used in producing some dyes.
acenaphthene: A colourless crystallinearomatic compound, C12H10;m.p. 95°C; b.p. 278°C.
Acenaphthene is an intermediatein the production of somedyes.
General Description
White needles.
Melting point 93.6°C.
Soluble in hot alcohol.
Denser than water and insoluble in water.
Hence sinks in water.
May irritate skin and mucous membranes.
Emits acrid smoke and irritating fumes when heated to decomposition.
Derived from coal tar and used to make dyes, pharmaceuticals, insecticides, fungicides, and plastics.
Acenaphthene appears as white needles.
Melting point 93.6°C.
Soluble in hot alcohol.
Denser than water and insoluble in water. Hence sinks in water. May irritate skin and mucous membranes.
Emits acrid smoke and irritating fumes when heated to decomposition.
Derived from coal tar and used to make dyes, pharmaceuticals, insecticides, fungicides, and plastics.
Acenaphthene is a polycyclic aromatic hydrocarbon derived from naphthalene by the addition of an ethylene bridge connecting C-1 and C-8.
Acenaphthene is a natural product found in Salvia coccinea and Gossypium hirsutum with data available.
Methods of Manufacturing
High-temperature coal tars contain on average 0.3% of acenaphthene.
Acenaphthene is also formed during coal tar distillation through hydrogenation of acenaphthalene.
Acenaphthene is concentrated to ca. 25% in the coal tar fraction boiling between 230 and 290 °C (wash oil) with about 7% recovery rate from continuous tar distillation.
The crystallizable acenaphthene fraction (bp ca. 270-275 °C) is obtained from the wash oil by redistillation.
Alternatively, it can be removed directly during primary tar distillation.
Technical acenaphthene (95-99%) is produced by crystallization in agitated coolers and centrifuges or by continuous countercurrent crystallization.
The pure compound is obtained by further distillation and recrystallization.
Bacterial oxidation of acenaphthene by Beijerinckia sp. and Beijerinckia sp. strain B8/36 has been reported.
Acenapthene forms 1:1:1 inclusion compound by complexing with inclusion compound of β-cyclodextrin and alcohol. Kinetics of the atmospherically important gas-phase reactions of acenaphthene with OH and NO3 radicals, O3 and N2O5 has been investigated at 296 ± 2K.
Acenaphthene is one of a group of chemicals called polycyclic aromatic hydrocarbons, PAHs for short.
PAHs are often found together in groups of two or more.
They can exist in over 100 different combinations but the most common are treated as a group of 15.
PAHs are found naturally in the environment but they can also be man-made.
Acenaphthene looks like a white crystal-like solid.
PAHs are created when products like coal, oil, gas, and garbage are burned but the burning process is not complete.
Very little information is available on the individual chemicals within the PAH group.
Most of the information available is for the PAH group as a whole.
Information specific to acenaphthene is included in this fact sheet when available.
What is acenaphthene used for?
Most of the PAHs are used to conduct research.
Like most PAHs, acenaphthene is used to make dyes, plastics and pesticides.
Acenaphthene has been found in cigarette smoke, in the exhaust from automobiles and in wood preservatives.
Formula: C12H10
Formula Weight: 154.21
Melting point: 92-95°
Boiling Point: 278°
Flash Point: 135°(275°F)
Density: 1.15
Storage & Sensitivity: Ambient temperatures.
Solubility
Soluble in chloroform, benzene, tolune, glacial acetic acid and methanol. Insoluble in water.
Applications
Acenaphthene is used in the preparation of naphthalene dicarboxylic anhydride, which is used as a precursor to dyes and optical brighteners.
Further, it is used in the preparation of active pharmaceutical ingredients and in plastics.
Acenaphthene is a natural component of crude oil and coal tar.
Acenaphthene is widespread in our environment as a result of the uses of oil and tar.
Acenaphthene can be created through incomplete combustion, such as forest fires, lightning strikes, and volcanic activity.
Acenaphthene has been found in car exhaust, wastewater, pesticides, and cigarette smoke.
Acenaphthene is also found in textile dyes.
Acenaphthene is one of over 100 different polycyclic aromatic hydrocarbons (PAHs).
PAHs are chemicals that are formed during the incomplete burning of organic substances, such as fossil fuels.
They are usually found as a mixture containing two or more of these compounds
Acenapthene sublimation is a standard visualisation technique used in the ARA Transonic Wind Tunnel (TWT) to detect the position of transition from laminar to turbulent flow on the model surface.
Acenaphthene is an effective tool for checking the performance of model transition bands or dots, which are used to fix the point of transition at a desired location on the model.
The model surface is prepared by spraying a solution of napthelene crystals onto the area of interest.
The tunnel is run at the desired condition and the change in flow at the point of transition causes the crystals to be removed behind the point of transition.
About Acenaphthene
Helpful information
This substance is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, for intermediate use only.
This substance is used by professional workers (widespread uses), at industrial sites and in manufacturing.
Consumer Uses
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the routes by which Acenaphthene is most likely to be released to the environment.
Article service life
ECHA has no public registered data on the routes by which Acenaphthene is most likely to be released to the environment. ECHA has no public registered data indicating whether or into which articles the substance might have been processed.
Widespread uses by professional workers
This substance has an industrial use resulting in manufacture of another substance (use of intermediates).
This substance is used for the manufacture of: chemicals.
Release to the environment of Acenaphthene can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates).
Formulation or re-packing
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the routes by which Acenaphthene is most likely to be released to the environment.
Uses at industrial sites
This substance has an industrial use resulting in manufacture of another substance (use of intermediates). This substance is used for the manufacture of: chemicals. Release to the environment of Acenaphthene can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates).
Manufacture
Release to the environment of Acenaphthene can occur from industrial use: manufacturing of the substance.
IUPAC NAMES:
1,2-Dihydroacenaphthene
1,2-dihydroacenaphthylene
Acenaphthene
acenaphthene
SYNONYMS:
Acenaphthcn
Acenaphthylene, 1,2-dihydro-
ethylenenaphthalene
NSC 7657
ACENAPHTHENE FOR SYNTHESIS 100 G
ACENAPHTHENE
acenaphylene
NAPHTHYLENEETHYLENE
PERI-ETHYLENENAPHTHALENE
1,8-ETHYLENENAPHTHALENE
1,2-DIHYDROACENAPHTHENE
1,2-DIHYDROACENAPHTHYLENE
1，2-Dihydroaceno-phthylene
Acenaphthene Zone Refined (nuMber of passes:30), 99.5%(GC)
COLOREX SALMONELLA PLUS (6X20)
acenaphylene 1,8-Ethylenenaphthalene
Acenaphthene Standard
1,8-dihydroacenaphthalene
1,8-Ethylenenaphthalene1,2-Dihydroacenaphthylene
acenaphtene
1,2-dihydro-acenaphthylen
acenaphtalenethylene
acenaphthene solution
ACENAPHTHENE, 5000MG, NEAT
ACENAPHTHENE, 1X1ML, MEOH, 5000UG/ML
ACENAPHTHENE, 1X1ML, MEOH, 200UG/ML
ACENAPHTHENE 99%
ACENAPHTHENE 96+%
AcenaptheneGr
Acenaphthene,>98%
1,2-dihydroacenphthylene
Acenaphthene Zone Refined (number of passes:30)
Acenaphthene,1,8-Ethylenenaphthalene
Acenaphthene, extra pure
Acenaphthene 1g [83-32-9]
Acenaphthene 5g [83-32-9]
Acenaphthene Zone Refined
Acenaphthene, 99% 5GR
Acenaphthene,99%
AcenaphtheneSolution,10mg/L,1ml
AcenaphtheneSolution,2000mg/L,1ml
AcenaphtheneSolution,100mg/L,1ml
AcenaphtheneSolution,100mg/L,10ml
AcenaphtheneSolution,50mg/L,1ml
AcenaphtheneSolution,1000mg/L,1ml
Acenaphthene (1,2-Dihydro Acenaphthylene)
Acenaphthene Zone Refined (number of passes:30)>
AcenaphtheneSolution,500mg/L,1ml
Acenaphthene >
Acenaphthene, pract
Acenaphthene, for HPLC 98%+
