Grundinformationen
- Standard-SMILES
c1cc2c3c(cccc3c1)CC2- InChIKey
CWRYPZZKDGJXCA-UHFFFAOYSA-N- Summenformel
- C12H10
- Durchschnittliche Molmasse
- 154,21 g/mol
- Monoisotopische Masse
- 154,07825032
Namen und Bezeichner
- Bevorzugter Name
- Acenaphthene
- IUPAC
- 1,2-dihydroacenaphthylene
- Lokaler Name
- Acenaphthen
- Englischer Name
- Acenaphthene
- Summenformel
- C12H10
- Molmasse
- 154.21
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
83-32-9- PubChem CID
- 6734
- DTXSID
DTXSID3021774- ChEMBL
CHEMBL1797271- ChEBI
CHEBI:22154- UNII
- V8UT1GAC5Y
- EC Number
- 201-469-6
- Nikkaji
- J3.533E
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,9
- Polarare Oberfläche (TPSA)
- 0 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 0
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 12
- Formalladung
- 0
- Komplexität
- 155
Experimentelle und physikochemische Eigenschaften
LogP
log Kow = 3.92
3.9/4.5
Density
1.024 at 210 °F (NTP, 1992) - Denser than water; will sink
1.222 g/cu cm at 20 °C
1.2 g/cm³
1.2 @25 °C
Color/Form
White needles
Orthorhombic bipyramidal needles from alcohol
Solubility
less than 1 mg/mL at 68 °F (NTP, 1992)
In water, 3.90 mg/L at 25 °C
In water, 3.57-3.93 mg/L at 22.2 to 25.04 °C (range of 7 values)
1 gram dissolves in 31 mL alcohol, 56 mL methanol, 25 ml propanol, 2.5 mL chloroform, 5 mL benzene or toluene
3.2 g/100 mL glacial acetic acid
Solubility in water, g/100ml at 25 °C: 0.0004
Flash Point
125.0 °C (257.0 °F) - closed cup
135 °C o.c.
Boiling Point
534 °F at 760 mmHg (NTP, 1992)
277.5 °C
279 °C
277.5 °C @760 [mm Hg]
Decomposition
Hazardous decomposition products formed under fire conditions - Carbon oxides.
When heated to decomposition it emits acrid smoke and irritating vapors.
Melting Point
203 °F (NTP, 1992)
93 °C
95 °C
95 °C
Vapor Density
5.32 (NTP, 1992) - Heavier than air; will sink (Relative to Air)
5.32 (Air = 1)
Relative vapor density (air = 1): 5.3
Odor Threshold
Odor detection in air, 8.0X10-2 ppm (chemically pure)
Threshhold odor concn in water at room temp: 0.08 ppm (range 0.02 to 0.22 ppm)
Odor low 0.5048 mg/cu m, odor high 0.5048 mg/cu m.
Vapor Pressure
0.001 to 0.01 mmHg at 68 °F ; 5 mmHg at 238.6 °F (NTP, 1992)
0.00215 [mmHg]
0.0022 mm Hg at 25 °C
Vapor pressure, Pa at 25 °C: 0.3
0.0016 [mm Hg] @25 °C
Physikochemische Eigenschaften
- Schmelzpunkt
- 90 · 90-94 °C(lit.)
- Siedepunkt
- 279 °C · 279 °C(lit.)
- Dichte
- 1.06 · 1.06
- Dampfdichte
- 5.32 · 5.32 (vs air)
- Dampfdruck
- 10 mm · 10 mm Hg ( 131 °C)
- Brechungsindex
- 1.6048 · 1.6048
- Flammpunkt
- 135 °C · 135 °C
- storage temp.
- 30 °C · Store below +30°C.
- Löslichkeit
- 50 mg/mL, · chloroform: 50 mg/mL, clear
- Aggregatzustand
- crystalline
- Farbe
- brown-beige
- Wasserlöslichkeit
- 0.000347 g/100 · 0.000347 g/100 mL
- Merck
- 14 · 14,28
- BRN
- 386081 · 386081
- Henry's Law Constant
- 3.47 · 3.47, 6.21, 10.8, 18.3, and 28.2 at 4.1, 11.0, 18.0, 25.0, and 31.0 °C, respectively (Bamford et al., 1998)
- Dielectric constant
- 3 · 3.0
- Stabilität
- Stable. Incompatible with strong oxidizing agents.
- InChI
- 1S/C12H10/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-6H,7-8H2
- InChIKey
- CWRYPZZKDGJXCA-UHFFFAOYSA-N
- SMILES
- C1Cc2cccc3cccc1c23
- LogP
- 4.04 at · 4.04 at 30℃ and pH5-8
- CAS Datenbank
- 83 · 83-32-9(CAS DataBase Reference)
- NIST chemische Informationen
- Acenaphthene(83-32-9)
- EPA chemische Informationen
- Acenaphthene (83-32-9)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 2.4% (3 of 127) of reports.
Warning
H319 (83.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H400 (89.8%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410 (90.6%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]
P264+P265, P273, P280, P305+P351+P338, P337+P317, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 127 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 3 of 127 reports by companies.;There are 9 notifications provided by 124 of 127 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Gefahrenhinweise
Regulatory Information
Chemical: Acenaphthylene, 1,2-dihydro-
Hazard Traits - Bioaccumulation; Carcinogenicity; Environmental Persistence; Hepatotoxicity and Digestive System Toxicity;Authoritative List - CWA 303(c); CWA 303(d); US EPA NWMP PBTs;Report - regardless of intended function of ingredient in the product
Acenaphthylene, 1,2-dihydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acenaphthylene, 1,2-dihydro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 06-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/10180;Status: No longer Valid Update: 18-08-2011 https://echa.europa.eu/registration-dossier/-/registered-dossier/6742
Restricted substance: Acenaphthene;EC: 201-469-6;Restriction condition document: PDF link
Acenaphthylene, 1,2-dihydro-: Does not have an individual approval but may be used under an appropriate group standard
Fire Hazards
Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Combustible. Finely dispersed particles form explosive mixtures in air.
Fire Potential
This chemical is a combustible solid.
Combustible.
Health Hazards
SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract. If ingested, it can cause vomiting. Chronic exposure may result in kidney and liver damage.;ACUTE/CHRONIC HAZARDS: This compound is harmful by inhalation, ingestion or skin absorption. It is an irritant of the skin, eyes, mucous membranes and upper respiratory tract. When heated to decomposition it emits toxic fumes of carbon monoxide and carbon dioxide. (NTP, 1992)
Special Reports
USEPA; Ambient Water Quality Criteria Doc: Acenaphthene (Draft) (1980)
USEPA; Ambient Water Quality Criteria Doc: Polynuclear Aromatic Hydrocarbons (Draft) (1980)
Health & Welfare Canada; Polycyclic Aromatic Hydrocarbons (1979) Report No. 80-EHD-50
USEPA; Health Assessment Document: Polycyclic Organic Matter (1979) EPA-600/9-79-008
For more Special Reports (Complete) data for ACENAPHTHENE (9 total), please visit the HSDB record page.
Sicherheit und Schutzausrüstung
Fire Fighting
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:;CAUTION: Fire involving Safety devices (UN3268) and Fire suppressant dispersing devices (UN3559) may have a delayed activation and a risk of hazardous projectiles. Extinguish the fire at a safe distance.;SMALL FIRE: Dry chemical, CO2, water spray or regular foam.;LARGE FIRE: Water spray, fog or regular foam. Do not scatter spilled material with high-pressure water streams. If it can be done safely, move undamaged containers away from the area around the fire. Dike runoff from fire control for later disposal.;FIRE INVOLVING TANKS: Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. (ERG, 2024)
Use water spray, dry powder, foam, carbon dioxide.
First Aid Measures
Fresh air, rest.
Remove contaminated clothes. Rinse and then wash skin with water and soap.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Rinse mouth.
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
Fire Fighting Procedures
Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical, or carbon dioxide.
Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.
Use dry chemical, carbon dioxide, water spray, or alcohol foam extinguishers. ... If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. ... The only respirators recommended for firefighting are self-contained breathing apparatuses that have full face-pieces and are operated in a pressure-demand or other positive-pressure mode.
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/
Storage Conditions
Keep container tightly closed in a dry and well-ventilated place. Storage class (TRGS 510): Non Combustible Solids.
Store in a secure poison location. ... Store in tightly closed containers in a cool, well-ventilated area. Sources of ignition, such as smoking and open flames, are prohibited where this chemical is used, handled, or stored in a manner that could create a potential for fire or explosion hazard.
Cleanup Methods
ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.
Evacuate persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area after cleanup is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. ... May be isolated using bentonite lined dam.
IARC describes laboratory decontamination and 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 for the decontamination of its residues on glassware and petri dishes, for the clean-up of spills of liquid wastes, and 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/
Nonfire Spill Response
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:;Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. For Asbestos, avoid inhalation of dust. Cover spill with plastic sheet or tarp to minimize spreading. Do not clean up or dispose of, except under supervision of a specialist.;SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area.;SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal.;LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2024)
Disposal Methods
SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.
Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber; Contaminated packaging: Dispose of as unused product.
Incineration or permanganate oxidation.
For more Disposal Methods (Complete) data for ACENAPHTHENE (7 total), please visit the HSDB record page.
Spillage Disposal
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
Preventive Measures
ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.
Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. Provide appropriate exhaust ventilation at places where dust is formed.
Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.
Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.
For more Preventive Measures (Complete) data for ACENAPHTHENE (10 total), please visit the HSDB record page.
Isolation and Evacuation
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:;IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.;SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.;FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)
Toxikologische Informationen
Body Burden
Human milk samples collected from 39 women in Beijing, China in 2005-2006 contained a mean acenaphthene concentration of 0.845 ng/g fresh weight(1); placenta collected from 27 women contained a mean acenaphthene concentration of 0.824 ng/g fresh weight(1); umbilical cord blood collected from 30 women contained a mean acenaphthene concentration of 0.229 ng/g fresh weight(1). Adipose tissue collected from Korean women in 2007-2008 contained a mean acenaphthene concentration of 6.4 ng/g lipid weight(2). Blood plasma collected from 111 human donors in Hong Kong in 2008 contained mean acenaphthene levels of 54.6 and 54.4 ng/g lipid in females and males respectively(3).
Ecotoxicity Values
LC50; Species: Lepomis macrochirus (bluegill); Conditions: static bioassay; Concentration: 1,700 ug/L for 96 hr
LC50; Species: Lepomis macrochirus (Bluegill) weight 0.32-1.2 g; Conditions: freshwater, static, 21-23 °C, pH 6.5-7.9, hardness 32-48 mg/L CaCO3, alkalinity 28-34 mg/L CaCO3, dissolved oxygen 0.3-9.7 mg/L; Concentration: 7200 ug/L for 24 hr />/= 80% purity/
LC50; Species: Mysidopsis bahia (mysid shrimp); Conditions: static bioassay; Concentration: 970 ug/L for 96 hr
LC50; Species: Cyprinodon variegatus (sheepshead minnow); Conditions: static bioassay; Concentration: 2,230 ug/L for 96 hr
For more Ecotoxicity Values (Complete) data for ACENAPHTHENE (27 total), please visit the HSDB record page.
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), a Koc range of 2510 to 2.14X10+5 in soil(2,3), indicates that acenaphthene is expected to have slight to no mobility in soil(SRC). Volatilization of acenaphthene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.84X10-4 atm-cu m/mole(4). However, adsorption to soil is expected to attenuate volatilization(SRC). Acenaphthene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.0022 mm Hg at 25 °C(5). The biodegradation half-life of acenaphthene in soil has been reported to range from less than 10 days(6) to over 100 days(7). The presence of acclimated microbes appears to be an important factor in the degradation rate(8). In addition, acenaphthene has been shown to biodegrade readily in acclimated soil at low concentrations (5 mg/kg), but not at high concentrations (500 mg/kg), perhaps due to toxicity to the microbes(9). Acenaphthene absorbs strongly at wavelengths >290 nm(10) and is expected to be susceptible to direct photolysis on soil surfaces exposed to sunlight(11). The photolysis of acenaphthene, sorbed on surfaces of needles of a spruce tree, had a half-life of 45 hours under sunlight irradiation(12).
AQUATIC FATE: Based on a classification scheme(1), a Koc range of 2510 to 2.14X10+5(2,3) indicates that acenaphthene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon a Henry's Law constant of 1.84X10-4 atm-cu m/mole(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 9.6 hours and 6.7 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is on the order of 1 to 10 months if adsorption is considered(6). According to a classification scheme(7), an observed BCF range of 254-1270(8) suggests the potential for bioconcentration in aquatic organisms is high to very high, provided the compound is not metabolized by the organism(SRC). Polycyclic aromatic hydrocarbons (PAHs), including acenaphthene, may not bioconcentrate in aquatic organisms which contain microsomal oxidase, such as some fish, as this enzyme enables the rapid metabolism of certain polycyclic aromatic hydrocarbons(9). The presence of acclimated microbes appears to be an important factor in the degradation rate in water(10). Acenaphthene was shown to biodegrade readily using acclimated groundwater aquifer inoculum, but very slowly using unacclimated or sterilized materials(10). The biotransformation half-lives for 2 mg/L of acenaphthene in pond and lake water with decreasing amounts of suspended solids range from 20 hours to 24.8 days for zero suspended solids(11). Acenaphthene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4). Acenaphthene absorbs strongly at wavelengths >290 nm(12) and is expected to be susceptible to direct photolysis at water surfaces exposed to sunlight(13).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), acenaphthene, which has a vapor pressure of 0.0022 mm Hg at 25 °C(2) is expected to exist solely as a vapor in the ambient atmosphere. However, gas/particle partitioning studies in chambers and outdoor monitoring have shown that acenaphthene can exist in both the vapor and particulate phases(3). Vapor-phase acenaphthene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 3.9 hours(SRC), calculated from its rate constant of 9.89X10-11 cu cm/molecule-sec at 25 °C(4). Vapor-phase acenaphthene is also degraded in the atmosphere by reaction with night-time nitrate radicals(SRC); the half-life for this reaction in air is estimated to be 1.9 hours(SRC), calculated from its rate constant of 4.16X10-13 cu cm/molecule-sec at 25 °C(4). Particulate-phase acenaphthene may be removed from the air by wet and dry deposition(SRC). Acenaphthene absorbs strongly at wavelengths >290 nm(5) and, therefore, is expected to be susceptible to direct photolysis by sunlight(SRC).
Food Survey Values
Acenaphthene was identified as a volatile component of cassava(1), roasted filberts(2) and nectarines(3). Assorted types of lima, pinto, red kidney, black, navy and mung beans, soybeans, split peas and lentils were found to contain acenaphthene at concentrations ranging from 2.8 to 49.2 ppb(4). Seven of 25 samples of margarines, butter and vegetable oils contained acenaphthene at concentrations of 2.9, 0.29, 1.43, 0.22, 1.1, 45 and 0.50 ug/kg(5). Foods collected from markets in Huelva, Spain in 2001 contained acenaphthene levels of 0.353-0.700 ng/g fresh wt in several fish products(6). Levels of acenaphthene detected in olive pomace oil in Spain ranged from 0.45-1.10 ug/kg(7). The following concentrations of acenaphthene (in ug/kg fresh wt) were detected in samples collected in the Czech Republic in 2003): cucumber, 0.07-0.45; parsley, 0.66-3.64; tomato, <0.07-0.16; apple, 0.17-0.31(8). Maximum acenaphthene levels (in ng/g wet wt) were detected in the following food items collected in Hong Kong in 2007: coconut milk (1.57), chicken breast (1.99), white wine (1.13), red wine (1.17), edible oils (1.34-3.07), pistachio (2.89), various seeds and nuts (1.57-3.09)(9). Acenaphthene was detected in the smoke from frying canola oil, sunflower oil, soybean oil and in fumes from fried chicken legs(10). Acenaphthene was detected in emissions from the charbroiling and grilling of beef and chicken(11).
Acenaphthene was detected in the following Finish cereal products, sampled in 1985(1):[Table#4133]
Exposure Routes
The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.
Oral (L10) ; inhalation (L10)
Milk Concentrations
ENVIRONMENTAL: Milk samples collected from farms in France near potential contamination sources in March 2000 contained mean acenaphthene concentrations of 0.3-1.0 ng/g milk fat(1). In a nationwide study of milk samples collected from 45 dairy farms in the US in 2000-2001, acenaphthene was not detected at a detection limit of 180 ng/L(2). Human milk samples collected from 39 women in Beijing, China in 2005-2006 contained a mean acenaphthene concentration of 0.845 ng/g fresh weight(3).
Toxicity Summary
IDENTIFICATION AND USE: Acenaphthene is a solid. It is used as an intermediate for manufacture of pharmaceuticals. Polycyclic aromatic hydrocarbons are a group of chemicals that are formed during the incomplete burning of coal, oil, gas, wood, garbage, or other organic substances, such as tobacco and charbroiled meat. HUMAN EXPOSURE AND TOXICITY: Acenaphthene is oxidized by human P450s 2A6 and 2A13 and other P450s to form several mono- and dioxygenated products. ANIMAL STUDIES: Acenaphthene at 2 g/kg body weight administered orally to seven young rats daily for 32 days caused loss of body weight and changes in peripheral blood, increased aminotransferase levels in blood serum, and produced mild morphological damage to both the liver and kidney. 100 rats were exposed for 5-months to acenaphthene at a level of 12 mg/cu m for four hours a day, six days per week. Toxic effects on the blood, lung, and glandular constituents were observed. The bronchial epithelium showed hyperplasia and metaplasia, which may have been symptoms of the pneumonia that killed a large number of animals. No signs of malignancy appeared during the 8-month post-exposure observation period. Acenaphthene at 0.10 % accelerated the liver regeneration in partially hepatectomized male rats. An acenaphthene-containing aromatic subfraction was isolated from shale-derived crude oil and tested for mutagenicity using Salmonella typhimurium TA98. No increases in mutation frequency were observed with or without metabolic activation. ECOTOXICITY STUDIES: Treatment of Allium cepa root meristem cells with acenaphthene vapor for 12-96 hr caused anomalies leading to random development of the cells. It caused disorientation of microtubules, in Allium cepa and Phleoeum pratense, resulting in altered cellular expansion. A set of embryo-larval bioassays were conducted with the fathead minnow. The no effect levels when compared to the controls was 0.226 mg/L acenaphthene.
The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (L10, L23, A27, A32)
Regulatorische Informationen
Regulatory Information
Chemical: Acenaphthylene, 1,2-dihydro-
Hazard Traits - Bioaccumulation; Carcinogenicity; Environmental Persistence; Hepatotoxicity and Digestive System Toxicity;Authoritative List - CWA 303(c); CWA 303(d); US EPA NWMP PBTs;Report - regardless of intended function of ingredient in the product
Acenaphthylene, 1,2-dihydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acenaphthylene, 1,2-dihydro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 06-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/10180;Status: No longer Valid Update: 18-08-2011 https://echa.europa.eu/registration-dossier/-/registered-dossier/6742
Restricted substance: Acenaphthene;EC: 201-469-6;Restriction condition document: PDF link
Acenaphthylene, 1,2-dihydro-: Does not have an individual approval but may be used under an appropriate group standard
CERCLA Reportable Quantities
Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).
Clean Water Act Requirements
Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations.
For the maximum protection of human health from the potential carcinogenic effects of exposure to polynuclear aromatic hydrocarbons through ingestion of contaminated water and contaminated aquatic organisms, the ambient water concentration should be zero, based on the nonthreshold assumption for this chemical. However, zero level may not be attainable at the present time. Therefore, the levels which may result in incremental increase of cancer risk over the lifetime are estimated at 1X10-5, 1X10-6, and 1X10-7. The corresponding recommended criteria are 28.0 ng/L, 2.8 ng/L, and 0.28 ng/L, respectively. If these estimates are made for consumption of aquatic organisms only, excluding consumption of water, the levels are 311.0 ng/L, 31.1 ng/L, and 3.11 ng/L, respectively. /Polynuclear aromatic hydrocarbons/.
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 3077 9/PG 3
- hs_code
- 29029080
- RTECS-Nr.
- AB1000000
- risk_code
- 36/37/38-50/53-39/23/24/25-23/24/25-11-52/53-67-65-38-51/53-20
- Toxizität
- LD50 orally in Rabbit: > 16000 mg/kg
- hazard_code
- Xi,N,T,F,Xn
- safety_code
- 26-36/37/39-60-61-37/39-45-36/37-16-7-62-36-33-25-9
- hazard_class
- 9
- packing_group
- III
- Speicherklasse
- 11 - Combustible Solids
- Giftige Stoffe Daten
- 83-32-9(Hazardous Substances Data)
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1
- Selbstentzündungstemperatur
- >450 °C
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
The filamentous fungus Cunninghamella elegans ATCC 36112 metabolized within 72 hr of incubation approximately 64% of the [1,8-(14)C]acenaphthene added. The radioactive metabolites were extracted with ethyl acetate and separated by thin-layer chromatography and reversed-phase high-performance liquid chromatography. Seven metabolites were identified by 1H nuclear magnetic resonance, UV, and mass spectral techniques as 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%). Parallel experiments with rat liver microsomes indicated that the major metabolite formed from acenaphthene by rat liver microsomes was 1-acenaphthenone. The fungal metabolism of acenaphthene was similar to bacterial and mammalian metabolism, since the primary site of enzymatic attack was on the two carbons of the five-member ring.
Metabolized to naphthalene-1,8-dicarboxylic acid in rats. /From table/
... Possibility of limited metabolism of acenaphthene to naphthalic acid and naphthalic anhydride.
A Beijerinckia species and a mutant strain, Beijerinckia species strain B8/36, were shown to oxidize the polycyclic aromatic hydrocarbons acenaphthene and acenaphthylene. Both organisms oxidized acenaphthene to the same spectrum of metabolites, which included 1-acenaphthenol, 1-acenaphtheneone, 1,2-acenaphthenediol, acenaphthenequinone, and a compound that was tentatively identified as 1,2-dihydroxyacenaphthylene. In contrast, acenaphthylene was oxidized to acenaphthenequinone and the compound tentatively identified as 1,2-dihydroxyacenaphthylene was also formed when the organism was incubated with synthetic cis-1,2-acenaphthenediol. A metabolite identified as cis-1,2-acenaphthenediol was formed from acenaphthylene by the mutant Beijerinckia species strain B8/36. Cell extracts prepared from the wild-type Beijerinckia strain contain a constitutive pyridine nucleotide-dependent dehydrogenase which can oxidize 1-acenaphthenol and 9-fluorenol. The results indicate that although acenaphthene and acenaphthylene are both oxidized to acenaphthenequinone, the pathways leading to the formation of this end product are different.
For more Metabolism/Metabolites (Complete) data for ACENAPHTHENE (7 total), please visit the HSDB record page.
PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (L10)
Verwendung und Herstellung
Uses
Derived from coal tar and used as a chemical intermediate in the production of dyes, plastics, insecticides, fungicides, and pharmaceuticals; [CAMEO]
For acenaphthene (USEPA/OPP Pesticide Code: 442200) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
Dye intermediate; manufacturing plastics; insecticide; fungicide.
Pharmaceuticals
PAHs are released into the environment via the combustion of fossil fuels, coke oven emissions and vehicle exhausts, as well as naturally from forest fires and volcanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (L10)
U.S. Imports
(1984) 6.49X10+7 g
(1986) 8.82X10+3 lb
Methods of Manufacturing
High-temperature coal tars contain on average 0.3% of acenaphthene. It 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.
By passing ethylene and benzene or naphthalene through a red hot tube. ... By heating tetrahydroacenaphthene with sulfur to 180 °C. ... From acenaphthenone or acenaphthenequinone by high pressure hydrogenation in decalin with nickel at 180-240 °C. ... From acenaphthenone oxime.
Formulations/Preparations
Component of dry tar. The avg percent weight for coke-oven tars and CVR (continuous vertical retort) tars is 0.96 in the United Kingdom, 0.3 in Federal Republic of Germany, and 1.05 in the USA (range 0.42-1.28). For low temp tars in the United Kingdom the avg percent weight is 0.19 and for lurgi tars the avg percent weight is 0.57. /From table/
Grade: Technical, 98%
General Manufacturing Information
Acenaphthylene, 1,2-dihydro-: ACTIVE
PAHs are a group of chemicals that are formed during the incomplete burning of coal, oil, gas, wood, garbage, or other organic substances, such as tobacco and charbroiled meat. There are more than 100 different PAHs. PAHs generally occur as complex mixtures (for example, as part of combustion products such as soot), not as single compounds. PAHs usually occur naturally, but they can be manufactured as individual compounds for research purposes; however, not as the mixtures found in combustion products. ... Others are contained in asphalt used in road construction. They can also be found in substances such as crude oil, coal, coal tar pitch, creosote, and roofing tar. They are found throughout the environment in the air, water, and soil. They can occur in the air, either attached to dust particles or as solids in soil or sediment. /Polycyclic aromatic hydrocarbons/
Anwendungen
BeschreibungAcenaphthene 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. It 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.
VerwendenAcenaphthene occurs in petroleum bottoms and is used as a dye intermediate, insecticide, and fungicide and in manufacturing plastics.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Ergänzende Hinweise
Definitionacenaphthene: A colourless crystallinearomatic compound, C12H10;m.p. 95°C; b.p. 278°C. It is an intermediatein the production of somedyes.
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