Fluoren-9-on

Other Classes -> Polycyclic Aromatic Hydrocarbons

Polycyclic aromatic compound

Log Kow = 3.58

3.58

INSOL IN WATER; SOL IN ALCOHOL, ACETONE, BENZENE; VERY SOL IN ETHER, TOLUENE, HOT BENZENE

Insoluble in water. Soluble in oxygenated and aromatic solvents

Dry Powder; Large Crystals

Yellow solid; [HSDB] Yellow chips; [MSDSonline]

This chemical does not meet GHS hazard criteria for 30% (6 of 20) of reports.

Warning

H315 (10%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 20 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Chemical: 9H-Fluoren-9-one

9H-Fluoren-9-one is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 9H-Fluoren-9-one 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)

REACH registered substance: Fluoren-9-one (EC: 207-630-7)

9H-Fluoren-9-one: Does not have an individual approval but may be used under an appropriate group standard

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 2300(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that fluorenone will have slight mobility in soil(SRC). Aerobic biodegradation of fluorenone is expected based on limited data and may be a major fate process for this compound in soil(SRC). Groundwater, taken from a gasoline contaminated aquifer, was used to inoculate samples containing fluorenone as the sole carbon source; complete degradation was observed by day 11-15(4). Fluorenone's estimated values for vapor pressure, 5.7X10-5 mm Hg(5,SRC), and Henry's Law constant(6,SRC) indicate that volatilization from dry and moist soil surfaces will not be a major fate process for this compound(SRC).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 2300(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that fluorenone should adsorb to suspended solids and sediment(SRC). Aerobic biodegradation of fluorenone is expected based on limited data and may be a major fate process for this compound in water(SRC). Groundwater, taken from a gasoline-contaminated aquifer, was used to inoculate samples containing fluorenone as the sole carbon source; complete degradation was observed by day 11-15(4). Fluorenone may volatilize from water surfaces, slowly, based on an estimated Henry's Law constant of 6.8X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). Estimated half-lives for a model river and model lake are 73 and 530 days, respectively(3,SRC). An estimated BCF value of 310(3,SRC), from a measured log Kow(2), suggests that fluorenone will bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(6). Fluorenone has been detected in samples of catfish(7) and snails(8).

ATMOSPHERIC FATE: According to a suggested classification scheme(1), an estimated vapor pressure of 5.7X10-5 mm Hg at 25 °C(2,SRC) indicates that fluorenone will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase fluorenone 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 about 3 days(3,SRC). Particulate-phase fluorenone may be physically removed from the air by wet and dry deposition(SRC).

Particulates and complex organic mixtures sampled from the exhaust of a flame retention head residential oil burner combusting No. 2 fuel oil under cyclic conditions(5 min on, 10 min off) contained fluorenone at unreported concentrations for 2 smoke densities(smoke 1 and 5)(1). Fine particle emissions from the combined exhaust of a vented natural gas-fired residential space heater plus a water heater contained up to 55.1 pg/kJ(2). Hardwood soot from residential wood stoves contained fluorenone(3). The organic extracts of emissions from burning wood (birch) and cereal straw (barley) contained fluorenone at 6414 ug/kg and 2711 ug/kg, respectively(4).

Chlorinated coal-tar leachate contained fluorenone at unreported concentrations(1). The coal tar pitch used in the Horizontal Stud Soderberg aluminum reduction process results in the emission of fluorenone(2). Sandy loam soil contaminated with coal tar more than 40 years earlier still contained fluorenone at unreported concentrations(3). During the process of rubber denuding, combustion products formed in the induction furnaces (at 677 °C) included fluorenone at 23,100 ug/kg rubber(4).

Diesel particle emissions from an Oldsmobile contained fluorenones at an approximate concentration of 4,000 ppm(1). Diesel exhaust from a 1979 Caterpillar Model 3208 running on No. 2 diesel fuel contained fluorenone at unreported concentrations(2). Combustion of both low and high sulfur kerosene type fuels in a gas turbine engine resulted in the release of fluorenone at concentrations of 16.25-296.6 and 1.75-95.22 ng/cu m, respectively, in the exhaust gas(3). Emissions from noncatalyst and catalyst automobiles contained 113.4 and 24.3 ug fluorenone/km; heavy-duty diesel trucks produced 65.0 ug fluorenone/km(4). Fluorenone was present in 2 of 3 samples of spent chlorination liquor from the bleaching of sulphite pulp at concentrations of 0.5 and 2 g/ton pulp(5). Fluorenone was detected in particles from brake linings and road dust at concentrations of 0.82 and 0.72 ug/g particle sample, respectively(6).

Fluorenone was found in 4 fly ash samples from 5 municipal incinerators (from Japan, Ontario, Canada, and The Netherlands); no fluorenone was found in the incinerator ash from The Netherlands(1). Fly ash samples from a municipal incinerator in Ontario, Canada contained fluorenone at unreported concentrations(2). Fluorenone has been identified in fly ash and stack emissions from coal combustion, in stack emissions of waste incinerators, and in fly ash from coal/refuse combustion(3). The combustion products of the Lurgi Eco Gas Procedure, where waste is gasified and the purified gas introduced into the reactor of a power station, included fluorenone at concentrations from not- detected to 290 g/normalized cu m in the crude gas, 38-160 g/normalized cu m in the purified gas, and not detected in the flue gas (detection limit = 2-20 ug/normalized cu m)(4).

A grab sample of final effluent from the Addison, OH treatment plant and a composite sample taken from the first manhole downstream from the Sauget, OH municipal wastewater treatment plant contained fluorenone at unreported concentrations(1). 1 of 15 wastewater samples collected from the inorganic chemicals manufacturing sector contained unreported concentrations of fluorenone(2).

The Koc of fluorenone is estimated as approximately 2300(SRC), using a measured log Kow of 3.58(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that fluorenone has only slight mobility in soil(SRC).

URBAN/SUBURBAN: Winter urban air from residential areas, city residential areas, and nonresidential areas of Minneapolis, MN (hardwood used in residential heating) contained fluorenone at concentrations of 3.7-11 ng/cu m, 2.0-5.3 ng/cu m, and 7.1-9.9 ng/cu m(1). Winter urban air from residential areas, city residential areas, and nonresidential areas of Salt Lake City (softwood used in residential heating) contained fluorenone at concentrations of 12-15 ng/cu m, 5.3-21 ng/cu m, and 5.1-8.0 ng/cu m(1). Air particulate samples collected in Barcelona, Spain, during Spring, Summer, Fall, and Winter contained fluorenone at 7, not detected, 2, and 7 ng/cu m (detection limit not given)(2). Mean gas and particulate-phase concentrations of fluorenone were 7.0 and 0.14 ng/cu m, respectively, in air samples collected in Portland, OR during 1984-1985(3). The mean air concentration of fluorenone in Portland, OR was 7 ng/cu m during 1984(4,5). Urban air particles from St. Louis, MO contained fluorenone at unreported concentrations(6).

INDOOR: Indoor and outdoor air from eight homes in Columbus, OH was sampled during the winter of 1986/1987; average concentrations of fluorenone in the kitchen, living room, and outdoors were 11, 12, and 4.2 ug/cu m, respectively(1). Kitchen, living room, and outdoor air samples contained fluorenone at 33, 40, 9.2, and 6.6, 7.4, 3.7 ng/cu m, respectively for two homes, a gas-heated home, occupied by smokers, using electricity for cooking, and an all-electric home with no smokers(2). The air in the potroom of a Soderberg aluminum reduction plant was sampled; fluorenone was identified at 51 ng/cu m(3).

Fluorenone's production and use as an intermediate(1) or reagent(2) may result in its release to the environment through various waste streams(SRC). Fluorenone is also found in fly ash from municipal incinerators(3), and in wood smoke(4) and fossil fuel combustion products(5). Soil contaminated with lubricating oil contained fluorenone as a biodegradation product(6).

Groundwater, taken from a gasoline contaminated aquifer, was used to inoculate samples measuring the biodegradability of fluorenone under aerobic conditions; complete degradation was observed by day 11-15(1). A laboratory adapted fixed-film culture, originally inoculated with groundwater bacteria degraded fluorenone with a leveling off of the reaction rate (at about 15 mg/sq m/day) at concentrations above 20 ug/L, indicating possible zero order reaction rate inside the biofilm(1). An increased reaction rate of 35-40 mg/sq m/day was seen in cultures taken one month later indicating that some adaptation of the bacterial population may have occurred(1). Two pure cultures of white rot fungi were able to completely biodegrade fluorenone (at 55.5 uM) within 14 days(2).

Fluorenone was present in sediment and suspended solid samples taken from the St. Louis Bay in the Duluth harbor(1). Fluorenone was identified in 4 of 7 sediment core sections collected from the left side of the Nervion River, Spain near an uncontrolled hazardous waste dump at concentrations of 0.7-34 ug/g(2). Superficial marine sediments of Cortiou Creek, in the sewage area of Marseilles, France, are contaminated with fluorenone at concentrations ranging from non-detectable to 300 ng/g (4 of 10 sites had measurable quantities of fluorenone; detection limit not given but is less than 0.5 ng/g)(3).

An estimated BCF value of 310 was calculated for fluorenone(SRC), using a measured log Kow of 3.58(1) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms will be an important fate process(SRC). Bullhead catfish from the Black River, Ohio(4), and snails from Pensacola Bay, Florida(5) contained fluorenone at 14 ppb and unreported concentrations, respectively, indicating that bioconcentration does occur in the aquatic environment.

The Henry's Law constant for fluorenone is estimated as 6.8X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that fluorenone will volatilize from water surfaces(2,SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 73 hours(2,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 530 days(2,SRC). Fluorenone's estimated values for vapor pressure, 5.7X10-5 mm Hg(3,SRC), and Henry's Law constant(1,SRC) indicate that volatilization from dry and moist soil will not be a major fate process for this compound(SRC).

In the course of analysis of the combustion products of fossil fuels, phenalen-1-one was identified. It was differentiated from fluoren-9-one and benzo(c)cinnoline, which exhibited similar mass spectra, by gas chromatographic mass spectrometry, high resolution mass spectrometry, and high performance liquid chromatography with high speed spectrophotometric detection. UV spectra were reported along with retention data for gas and liquid chromatography. Mutagenic activity was determined in Salmonella typhimurium, using resistance to the purine analogue 8-azaguanine as a genetic marker. Phenalen-1-one was a potent mutagen, while benzo(c)cinnoline was 6-fold less active. Fluoren-9-one was completely inactive as a bacterial mutagen.

FLUORENONE IS FORMED FROM 9-HYDROXYFLUORENE.

FLUORENONE WAS FORMED AS A METABOLITE OF FLUORENE IN MOSQUITO FISH (GAMBUSIA) OF THE MODEL ECOSYSTEM STUDY.

The metabolism of fluorene, a tricyclic aromatic hydrocarbon, by Cunninghamella elegans ATCC 36112 was investigated. Approximately 69% of the 9-(14)C-fluorene added to cultures was metabolized within 120 hours. The major ethyl acetate-soluble metabolites were 9-fluorenone (62%), 9-fluorenol, and 2-hydroxy-9-fluorenone (together, 7.0%). Similarly to bacteria, Cunninghamella elegans oxidized fluorene at the C-9 position of the five-member ring to form as alcohol and the corresponding ketone. In addition, Cunninghamella elegans produced the novel metabolite 2-hydroxy-9-fluorenone.

Used as an intermediate and a reagent (Oppenauer oxidation); [HSDB]

Intermediate

Reagent (Oppenauer oxidation)

Used as a chemical intermediate in the synthesis of: 2-methyl-3-phenylbenzyl alcohol; 2,3,7-trinitrofluorenone

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

9H-Fluoren-9-one: ACTIVE