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ACENAPHTHYLENE

CAS：208-96-8
MW:152.19192
MF：C12H8

Acenaphthylene is a PAH with three aromatic rings. It is an intermediate chemical forthe manufacture of dyes, soaps, pigments, pharmaceuticals, insecticides, fungicides,herbicides, plant growth hormones, naphthalic acids, naphthalic anhydride (pigments),and acenaphthylene (resins) and is used to manufacture plastics. The largest emissionsof PAHs result from incomplete combustion of organic materials during industrialprocesses and other human activities. These include (1) processing of coal, crudeoil, and natural gas, including coking, coal conversion, and petroleum refining; (2)production of carbon blacks, creosote, coal tar, and bitumen; (3) aluminium, iron, andsteel production in plants and foundries; (4) heating in power plants and residencesand cooking; (5) combustion of refuse; (6) motor vehicle traffic; and (7) environmentaltobacco smoke. View more+

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: ACENAPHTHYLENE

1.2 Synonyms: 1,2-dihydroacenaphthylene-1,2-diide; 1,8-ethylene-naphthalene; acenaphthene; acenaphthylene anion radical; Acenaphthylene Standard; acenaphthylene,industrial; cyclopenta(de)naphthalene; Cyclopenta[de]naphthalene; EINECS 205-917-1; MFCD00003806; NSC 59821;

1.3 CAS No.: 208-96-8

1.4 CID: 9161

1.5 EINECS: 205-917-1

1.6 Molecular Formula: C12H8

1.7 Inchi: InChI=1S/C12H8/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-8H

1.8 InChkey: HXGDTGSAIMULJN-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC2=C3C(=C1)C=CC3=CC=C2

1.10 Isomers Smiles: C1=CC2=C3C(=C1)C=CC3=CC=C2

2. Properties

2.1 Solubility: 3.93mg/L(25 ºC)

2.2 Appearance: Acenaphthylene is a colorless crystalline solid. Insoluble in water. Used in dye synthesis, insecticides, fungicides, and in the manufacture of plastics.

2.3 Atmospheric OH Rate Constant: 1.10e-10 cm3/molecule*sec

2.4 Chemical Properties: Acenaphthylene is a polycyclic aromatic hydrocarbon (PAH) with three aromatic rings. It is used to manufacture plastics. Intermediate for dyes, soaps, pigments, pharmaceuticals, insec-ticide, fungicide, herbicide, and plant growth hormones. Intermediate for naphthalic acids, naphthalic anhydride (intermediate for pigments), and acenaphthylene (intermediate for res-ins). The largest emissions of PAH result from incomplete combustion of organic materials during industrial processes and other human activities. These include (a) processing of coal, crude oil, and natural gas, including coal; (b) coking, coal conversion, petroleum refi ning, and production of carbon blacks, creosote, coal-tar, and bitumen; (c) aluminium, iron, and steel production in plants and foundries; (d) heating in power plants and residences and cooking; (e) combustion of refuse; (f) motor vehicle traffi c; and (g) environmental tobacco smoke.

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2.5 Physical Properties: Colorless to white prisms or crystalline plates from alcohol with an odor similar to coal tar oraromatic hydrocarbons.

2.6 Decomposition: Hazardous decomposition products formed under fire conditions - Carbon oxides.

2.7 Heat of Vaporization: 64.6-69.1 kJ/mol

2.8 HenrysLawConstant: 1.14e-04 atm-m3/mole

2.9 Water Solubility: Very soluble in ethanol, ether, benzene; slightly soluble in chloroform

2.10 Spectral Properties: MAX ABSORPTION (CYCLOHEXANE): 267 NM (LOG E= 3.48); 311 NM (LOG E= 3.88); 323 NM (LOG E= 3.98); 335 NM (LOG E= 3.66); 340 NM (LOG E= 3.67); SADTLER REFERENCE NUMBER: 13704 (IR, PRISM)
IR 7227 (Coblentz Society Spectral Collection)
NMR 16066 (Sadtler Research Laboratories Spectral Collection)
MASS 108 (Aldermaston, Eight Peak Index of Mass Spectra, UK)
UV: 3631 (Sadtler Research Laboratories Spectral Collection)
Intensity of mass spectral peaks: 152 m/z (100%), 151 m/z (20%), 76 m/z (17%), 153 m/z (14%)

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2.11 Stability: Stable. Incompatible with oxidizing agents.

2.12 StorageTemp: APPROX 4°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A ortho- and peri-fused tricyclic hydrocarbon that occurs in coal tar.

3.2 Description: Acenaphthylene is a polycyclic aromatic hydrocarbon (PAH) with three aromatic rings. It is used to manufacture plastics. Intermediate for dyes, soaps, pigments, pharmaceuticals, insec-ticide, fungicide, herbicide, and plant growth hormones. Intermediate for naphthalic acids, naphthalic anhydride (intermediate for pigments), and acenaphthylene (intermediate for res-ins). The largest emissions of PAH result from incomplete combustion of organic materials during indust

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3.3 General Description: Colorless crystalline solid. Insoluble in water. Used in dye synthesis, insecticides, fungicides, and in the manufacture of plastics.

3.4 Methods of Manufacturing: Derived from acenaphthene by gas-phase catalytic dehydrogenation: put the industrial acenaphthene into the melting kettle and heat it with indirect steam to melt it all.?Pressurized liquid acenaphthene is pressed into the spiral gasification mixer, heated and vaporized with steam, the direct steam and acenaphthene steam are mixed into the superheating furnace, superheated to 450±20℃, enter the dehydrogenation reactor, after catalytic dehydrogenation reaction, then Crude acenaphthylene was obtained by condensation and drying.?Dissolve crude acenaphthene with ethanol, remove carbonized materials and mechanical impurities, and cool, crystallize, and dry to obtain the finished product.?The catalysts used are zinc oxide (85%), calcium oxide (5%), potassium sulfate (5%), potassium chromate (3%), and potassium hydroxide (2%).

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3.5 Potential Exposure: 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.

3.6 Purification Methods: 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.]

3.7 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.

3.8 Usage: Polycyclic aromatic hydrocarbons as carcinogenic

4. Safety and Handling

4.1 Octanol/Water Partition Coefficient: log Kow= 4.07

4.2 Other Preventative Measures: SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
In addition to a respirator selection, a complete respiratory protection program should be instituted which includes regular training, maintenance, inspection, cleaning, and evaluation. /Coal tar pitch volatiles/
Workers subject to skin contact with coal tar pitch volatiles should wash with soap or mild detergent and water any areas of the body which may have contacted coal tar pitch volatiles at the end of each work day. Employees who handle coal tar pitch volatiles should wash their hands thoroughly with soap or mild detergent and water before eating, smoking, or using toilet facilities. /Coal tar pitch volatiles/
Areas in which exposure to coal tar pitch volatiles may occur should be identified by signs or other appropriate means, & access to these areas should be limited to authorized persons. /Coal tar pitch volatiles/
Clothing contaminated with coal tar pitch volatiles should be placed in closed containers for storage until it can be discarded or until provision is made for the removal of coal tar pitch volatiles from the clothing. If the clothing is to be laundered or otherwise cleaned to remove the coal tar pitch volatiles, the person performing the operation should be informed of coal tar pitch volatiles' hazardous properties. /Coal tar pitch volatiles/
If the use of respirators is necessary, the only respirators permitted are those that have been approved by the Mine Safety and Health Administration (formerly Mining Enforcement and Safety Administration) or by the National Institute for Occupational Safety and Health. /Coal tar pitch volatiles/

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4.3 Cleanup Methods: IARC describes laboratory decontamination & destruction methods for some polycyclic aromatic hydrocarbons in this publication. When dealing with compounds other than those listed, the efficiency of the methods should first be verified. Acenaphthylene is not listed, but the methods may be applicable for the decontamination of its residues on glassware & petri dishes, for the clean-up of spills of liquid wastes, & for the clean-up of spills of the pure cmpd in solid state. /Polycyclic aromatic hydrocarbons/
... In surface waters, one-third of the total polycyclic aromatic hydrocarbons is bound to larger suspended particles, another one-third is bound to finely dispersed particles, and the remaining one-third is present in dissolved form. The particle-bound portion of polycyclic aromatic hydrocarbons can be removed by sedimentation, flocculation, and filtration processes. The remaining /material/ dissolved polycyclic aromatic hydrocarbons usually requires oxidation for partial removal and/or transformation. /Polynuclear aromatic hydrocarbons/

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4.4 DisposalMethods: The following wastewater treatment technologies have been investigated for acenaphthylene concentration process: Chemical precipitation.
IARC describes laboratory decontamination & destruction methods for some polycyclic aromatic hydrocarbons in this publication. When dealing with compounds other than those listed, the efficiency of the methods should first be verified. Acenaphthene is not listed, but the methods may be applicable to its destruction. The methods described are: Method 1: Destruction of Some Polycyclic Aromatic Hydrocarbons Using Potassium Permanganate Under Acidic Conditions, Method 2: Destruction of Some Polycyclic Aromatic Hydrocarbons Using Concentrated Sulfuric Acid, & Method 3: Destruction of Some Polycyclic Aromatic Hydrocarbons Using an Aqueous Saturated Potassium Permanganate Solution. The recommended destruction method (in order of preference) for specific waste categories are: methods 1, 3, 2 for pure compounds, for solutions of the polycyclic aromatic hydrocarbons in organic solvents (excluding dimethyl sulfoxide & dimethylformamide), for solutions of the polycyclic aromatic hydrocarbons in oil, & for the contents of petri dishes; methods 2, 1, 3 for solutions of the polycyclic aromatic hydrocarbons in dimethyl sulfoxide; methods 1,3 for solutions of the polycyclic aromatic hydrocarbons in dimethylformamide; & method 1 for aqueous solutions, & spills of solutions containing the polycyclic aromatic hydrocarbons, & for spills of the pure compound in solid state. /Polycyclic aromatic hydrocarbons/
A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 deg C and residence times of seconds for liquids and gases, and hours for solids. /Naphthalene/

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4.5 Fire Fighting Procedures: Foam, dry chemical, and carbon dioxide. /Coal tar pitch volatiles/
/During firefighting wear/ self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive pressure mode. /Coal tar pitch volatiles/

4.6 Safety Profile: Moderately toxic by intraperitonealroute. Mutation data reported. When heated todecomposition it emits acrid smoke and irritating fumes.

4.7 Incompatibilities: 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

4.8 Protective Equipment and Clothing: Respiratory protection for coal tar pitch volatiles is as follows: Particulate concentration of 2 mg/cu m or less: A chemical cartridge respirator with an organic vapor cartridge(s) and with a fume or high efficiency, or any supplied-air respirator, or any self-contained breathing apparatus. 10 mg/cu m or less: A chemical cartridge respirator with a full facepiece and an organic vapor cartridge(s) and with a fume or high-efficiency filter, or gas mask with a chin-style or a front- or back-mounted organic vapor canister and with a full facepiece and a fume or high-efficiency filter, or any supplied-air respirator with a full facepiece, helmet, or hood, or any self-contained breathing apparatus with a full facepiece. 200 mg/cu m or less: A type C supplied-air respirator operated in pressure-demand or other positive pressure or continuous-flow mode, a powered air-purifying respirator with an organic vapor cartridge and a high-efficiency particulate filter. 400 mg/cu m or less: A type C supplied-air respirator with a full facepiece operated in pressure-demand or other positive pressure mode or with a full facepiece, helmet, or hood operated in continuous-flow mode. Greater than 400 mg/cu m or entry and escape from unknown concentrations: A combination respirator which includes a type C supplied-air respirator with a full facepiece operated in pressure-demand or other positive pressure mode; Escape: Any gas mask providing protection against organic vapors and particulates, including pesticide respirators which meet the requirements of this class; any escape self-contained breathing apparatus. /Coal tar pitch volatiles/
Employees should be provided with and required to use impervious clothing, gloves, face-shields (eight-inch minimum), and other appropriate protective clothing necessary to prevent any possibility of skin contact with coal tar pitch volatiles. Employees should be provided with and required to use splash-proof goggles where there is any possibility of liquid coal tar volatiles contacting the eyes. /Coal tar pitch volatiles/
Respirator selection: upper limit devices recommended by NIOSH: Greater than any detectable concn: use any self-contained breathing apparatus with a full facepiece and operated in a pressure-demand or other positive pressure mode; or any supplied-air respirator with a full facepiece and operated in pressure-demand or other positive pressure mode in combination with an auxiliary self-contained breathing apparatus operated in pressure-demand or other positive pressure mode. Escape: Any air-purifying full facepiece respirator (gas mask) with a chin-style or front- or back-mounted organic vapor canister having a high-efficiency particulate filter, or any appropriate escape-type self-contained breathing apparatus. /Coal tar pitch volatiles/

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4.9 Safety: 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
22:Harmful if swallowed
36/37/38:Irritating to eyes, respiratory system and skin
67:Vapors may cause drowsiness and dizziness
65:Harmful: May cause lung damage if swallowed
50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
38:Irritating to the skin
11:Highly Flammable
39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed
23/24/25:Toxic by inhalation, in contact with skin and if swallowed
Safety Statements:26-36/37/39-62-61-60-45-36/37-16-7-37/39
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
62:If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label
61:Avoid release to the environment. Refer to special instructions safety data sheet
60:This material and/or its container must be disposed of as hazardous waste
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36/37:Wear suitable protective clothing and gloves
16:Keep away from sources of ignition - No smoking
7:Keep container tightly closed
37/39:Wear suitable protective clothing, gloves and eye/face protection
RIDADR:UN 1145 3/PG 2
WGK Germany:3

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4.10 Specification: yellow crystalline powder
Safety Statements:26-36/37/39-62-61-60-45-36/37-16-7-37/39
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
62:If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label
61:Avoid release to the environment. Refer to special instructions safety data sheet
60:This material and/or its container must be disposed of as hazardous waste
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36/37:Wear suitable protective clothing and gloves
16:Keep away from sources of ignition - No smoking
7:Keep container tightly closed
37/39:Wear suitable protective clothing, gloves and eye/face protection

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4.11 Toxicity: Celiac-rat LD50: 1700mg/kg

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Dermal, Category 1

Acute toxicity - Inhalation, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H310 Fatal in contact with skin H330 Fatal if inhaled
Precautionary statement(s)
Prevention	P262 Do not get in eyes, on skin, or on clothing. P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. P284 [In case of inadequate ventilation] wear respiratory protection.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P310 Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P361+P364 Take off immediately all contaminated clothing and wash it before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P320 Specific treatment is urgent (see ... on this label).
Storage	P405 Store locked up. P403+P233 Store in a well-ventilated place. Keep container tightly closed.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 400 MHz in CDCl3

IR : KBr disc

IR : nujol mull

Mass

Mass spectrum (electron ionization)

UV/Visible spectrum

7. Synthesis Route

208-96-8Total: 99 Synthesis Route

83-32-9 41 Suppliers

208-96-8 103 Suppliers

95-57-8 35 Suppliers

208-96-8 103 Suppliers

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8. Precursor and Product

precursor:

71-43-2

86-00-0

82-86-0

95-57-8

83-32-9

74-98-6

product:

2235-15-6

480-72-8

208-96-8

81-84-5

6306-07-6

82-86-0

191-48-0

83-32-9

203-42-9

518-05-8

9. Computed Properties

Molecular Weight：152.19192g/mol
Molecular Formula：C₁₂H₈
Compound Is Canonicalized：True
Exact Mass：3.7
XLogP3-AA：152.062600255
Monoisotopic Mass：152.062600255
Complexity：184
Rotatable Bond Count：0
Hydrogen Bond Donor Count：0
Hydrogen Bond Acceptor Count：0
Topological Polar Surface Area：0
Heavy Atom Count：：12
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADccBwAAAAAAAAAAAAAAAAAAAAAQAAAAAwYAAAAAAAAEDBUAAAGAAAAAAADACAGAAwAMAAAACAAiBCAAACAAAgAAAIiAAAAIgIICKAERCAIAAggAAIiAcAgMAOgAACAAAQAAAAAAQAACAAAAAAAAAAAA==

10.Other Information

Storage Conditions: Derived from acenaphthene by gas-phase catalytic dehydrogenation: put the industrial acenaphthene into the melting kettle and heat it with indirect steam to melt it all.?Pressurized liquid acenaphthene is pressed into the spiral gasification mixer, heated and vaporized with steam, the direct steam and acenaphthene steam are mixed into the superheating furnace, superheated to 450±20℃, enter the dehydrogenation reactor, after catalytic dehydrogenation reaction, then Crude acenaphthylene was obtained by condensation and drying.?Dissolve crude acenaphthene with ethanol, remove carbonized materials and mechanical impurities, and cool, crystallize, and dry to obtain the finished product.?The catalysts used are zinc oxide (85%), calcium oxide (5%), potassium sulfate (5%), potassium chromate (3%), and potassium hydroxide (2%).

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Storage features: Warehouse ventilated, low temperature and dry

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12. Related Questions

: What is ACENAPHTHYLENE and how is it prepared?Background and Overview ACENAPHTHYLENE, also known as acenaphthylene or 1,8-ethylnaphthalene, is a polycyclic aromatic hydrocarbon organic compound that contains a naphthalene ring bridged by an ethyl..; What is the synthesis and modification of ACENAPHTHYLENE?Introduction ACENAPHTHYLENE, a polycyclic aromatic hydrocarbon, is commonly used in organic optoelectronic materials due to its rich photophysical properties, such as organic field-effect transistors,..; Why is acenaphthylene aromatic when it has 12 pi electrons?Huckel's rule states that the aromaticity of a cyclic molecule should have (4n + 2) π electrons, where n is any whole number. The structural formula of acenaphthylene is shown below: Acenaphthylene i..

13. Realated Product Infomation