Benzanthrone

@ 20 °C: 0.52 G IN 100 G GLACIAL ACETIC ACID

@ 20 °C: 1.61 G IN 100 G BENZENE

@ 20 °C: 2.05 G IN 100 G CHLOROBENZENE

SOL IN ALCOHOL & OTHER ORG SOLVENTS

338 °F (NTP, 1992)

170 °C

1 mmHg at 437 °F ; 40 mmHg at 662.0 °F (NTP, 1992)

0.00000022 [mmHg]

Benzanthrone appears as yellow needles. (NTP, 1992)

Pale yellow solid; [Merck Index] Light yellow powder; [Alfa Aesar MSDS]

145.71 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]

144 Ų [M+H]+

Warning

H315 (97.7%): Causes skin irritation [Warning Skin corrosion/irritation]

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

Aggregated GHS information provided per 44 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Low acute but high sub-chronic toxicity in rats, mice, and rabbits manifesting by damage to blood and liver; Histopathological and biochemical changes observed in blood, liver, testes, kidneys, and urinary bladder in 30-day feeding study of guinea pigs; [HSDB] May cause irritation to eyes, skin, upper respiratory tract, and mucous membranes; [CAMEO] A mild skin and moderate eye irritant; Causes changes in hepatic microsomal mixed oxidase, other transferases, and other enzymes when applied to skin of mice intermittently for 34 weeks; Causes impaired liver function, changes in liver and bladder weight, and changes in erythrocyte count in 30 and 90 day intermittent oral studies of rats; [RTECS] A skin and severe eye irritant; [Alfa Aesar MSDS] See POLYCYCLIC AROMATIC HYDROCARBONS.

WENS EJ, WARD DM; REVIEW OF THE TOXICOLOGY OF COLORED CHEMICAL SMOKES AND COLORED SMOKE DYES; US NTIS, AD/A REP 003827/3GA, 72 PP (1974). THIS REPORT IS A REVIEW OF THE INHALATION (TOTAL-BODY-EXPOSURE) STUDIES PERFORMED BY THE EDGEWOOD ARSENAL LAB DURING 1966 WITH THE M18 SERIES OF COLORED SMOKES.

DACRE JC ET AL; REPORT USAMBRDL-TR-7704; ORDER NO AD-A090631 101 PP (1979). A DATA BASE AND SUMMARY OF PHYSICAL/CHEMICAL PROPERTIES, ANALYTICAL METHODS, MAMMALIAN TOXICOLOGY, ENVIRONMENTAL CONSIDERATIONS, AND STANDARDS, WHERE AVAILABLE, ARE PROVIDED FOR BENZANTHRONE.

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.

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

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.

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 9.8X10+3(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that benzanthrone will have no mobility in soil(SRC). Volatilization of benzanthrone will not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 6.61X10-8 atm-cu m/mole(4,SRC), and from dry soil surfaces(SRC) based on an estimated vapor pressure of 2.21X10-7 mm Hg(5,SRC).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 1.5X10+6(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that benzanthrone would adsorb to suspended solids and sediment(SRC) in water. Benzanthrone will not volatilize from water surfaces based on an estimated Henry's Law constant of 6.61X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated half-lives for a model river and model lake are 840 and 6116 days, respectively(3,SRC). According to a classification scheme(5), an experimental BCF value of 181(2) suggests that benzanthrone will bioconcentrate moderately in aquatic organisms(SRC).

ATMOSPHERIC FATE: According to a suggested classification scheme(1), an estimated vapor pressure of 2.21X10-7 mm Hg at 25 °C(2,SRC) indicates that benzanthrone will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase benzanthrone 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 21 hours(3,SRC). Particulate-phase benzanthrone may be physically removed from the air by wet and dry deposition(SRC).

Benzanthrone has been detected but not quantified in National Bureau of Standards, Standard Reference Material 1650 (particulates from heavy duty diesel engines)(1), passenger car diesel exhaust particulates(2,3), other diesel engine exhaust particulates(4,7), municipal waste incinerator fly ash(4,5,7), and wood and coal smoke(4,6,7). In smoke from a forest fire, benzanthrone was the major oxo PAH component, present at 4.4 ug per cu m(8). Smoke from a horizontally baffeled residential wood-burning stove burning birch produced between 490 and 741 ug per kg of wood burned, while a stoker-fed furnace burning barley straw produced between 69 and 166 ug per kg straw burned(9). Smoke from hot styrene-butadiene rubber produced 6500 ug per kg rubber(10). Benzanthrone is also present in spent chlorination liquor from bleaching of sulfite pulp at 0.4-0.6 g per ton pulp depending on the conditions(11).

/ALL/ PERSONS /ESPECIALLY THOSE/ WITH FAIR SKIN ... & PERSONS WITH SKIN DISEASES /SRP: SHOULD BE PROTECTED FROM EXPOSURE TO BENZANTHRONE/.

EMPLOYMENT OF PERSONS WITH LIVER, DIGESTIVE SYSTEM &, ESP GASTRIC, DISEASES /SRP: MUST BE PROTECTED FROM BENZANTHRONE EXPOSURE/.

The Koc of benzanthrone is estimated as approximately 1.22X10+4(SRC), using an experimental log Kow of 4.81(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that benzanthrone is immobile in soil(SRC).

Benzanthrone is a product of wood and coal combustion and will be present in the smoke from naturally produced combustion such as forest fires(1-4). Benzanthrone appears to be a metabolite of diesel oil when incubated in soil(5), and may be present in soils contaminated with diesel oil(SRC).

URBAN/SUBURBAN: Benzanthrone was found in the ambient air in Portland, OR (Feb-Apr 1984, Feb-Mar 1985) at 1.7 ng per cu m adsorbed onto particles trapped by a glass fiber filter and 0.067 ng per cu m in the gas phase (trapped by a polyurethane foam plug or Tenax trap)(1). Benzanthrone was also found on particulate matter (less than 2.1 um) in the ambient air in the Los Angeles area(2). Samples were taken over a 24-hour period at 6-day intervals during 1982. The results showed the following: West Los Angeles (0.62 ng per cu m), downtown (0.81 ng per cu m), Pasadena (0.84 ng per cu m), Rubidom (0.24 ng per cu m). Extracts of particulate samples collected by the National Air Sampling Network January-June 1966 from 50 cities in 45 states and the District of Columbia showed a concentration range of 0.9-13 ng per cu m(3). Samples of air borne particulates taken at 5 locations in Toronto, Ontario, Canada during 1972 and 1973 showed an average summer concentration of 30.5 ug per g particulate and winter concentration of 39.1 ug per g particulate(4). In Duisburg, Germany, particulate samples collected from ambient air in February-April 1982 contained 0.46-3.66 ng per cu m(5). Particulate samples collected in Barcelona, Spain during spring (March 16-22, 1989), summer (June 27-July 7, 1989), fall (November 6-13, 1989), and winter (February 5-12, 1990) showed concentrations of 15, 722, 282, and 30 pg per cu m, respectively(6). The pattern of higher concentrations during the summer and fall was not seen with most other polynuclear aromatic hydrocarbons (PAH) or PAH ketones detected in this study; these molecules generally showed higher concentrations in winter. Benzanthrone was also detected but not quantified in the air over Elverum, Norway(7).

RURAL/REMOTE: Samples of air borne particulates taken over a 24-hour period at 6-day intervals during 1982 over San Nicholas Island off the coast of Southern California showed average benzanthrone concentrations of less than 0.01 ng per cu m(1). By contrast, aerosols collected over the southern North Atlantic Ocean contained 0.45 ng per cu m(2).

PERSONS WITH...EXPOSURE...BETWEEN MONTHS & YEARS COMPLAIN OF LOSS OF APPETITE, INTOLERANCE OF FATTY FOODS, FATIGUE & WEAKNESS. COMPLAINTS OF DECR IN SEXUAL POTENCY...OFTEN OBJECTIVE WT LOSS &...REPORTS OF NEURASTHENIC SYNDROME, CHANGES IN CORNEAL & CREMASTER REFLEXES...ACCELERATED PULSE & REDUCED BLOOD PRESSURE...

MOST COMMON HAZARD...IS SKIN SENSITIZATION DUE TO EXPOSURE TO...DUST, ESP IN PERSONS...BLOND OR RED-HEADED. ...AFTER EXPOSURE OF BETWEEN FEW MO OR SEVERAL YR, SENSITIVE PERSONS DEVELOP ECZEMA WHICH MAY BE INTENSE IN ITS COURSE & ACUTE PHASE...MAY LEAVE HAZEL OR SLATE-GREY PIGMENTATION, ESP AROUND EYES.

THERE HAVE...BEEN REPORTS OF LIVER FUNCTION IMPAIRMENT & GASTRITIS WITH DECR ACIDITY /IN PERSONS EXPOSED TO BENZANTHRONE FOR MONTHS OR YEARS/.

...HAZARD...ESP IN PERSONS WHO ARE BLOND OR RED-HEADED. ... SKIN DISORDERS DUE TO BENZANTHRONE ARE MORE FREQUENT IN WARM SEASON & ARE SIGNIFICANTLY AGGRAVATED BY HEAT & LIGHT.

IT HAS BEEN FOUND POSSIBLE TO DECR INCIDENCE OF SKIN DISEASE BY LIMITING USE OF BENZANTHRONE TO COLDER SEASONS.

DIESEL ENGINE SOOT CONTAINS BENZANTHRONE.

Benzanthrone's production and use as an intermediate in the production of dyes(1) may result in its release to the environment through various waste streams(SRC). Benzanthrone has been detected in particulates from heavy duty diesel engines(2), passenger car diesel exhaust particulates(3,4), other diesel engine exhaust particulates(5,8), municipal waste incinerator fly ash(5,6,8), and wood and coal smoke(5,7,8) all of which enter the environment(SRC).

Benzanthrone at 100 ppm degraded 0% using 30 ppm sludge after 4 weeks of incubation(1). Benzanthrone was not present the first week in soil treated with diesel oil then incubated, but appeared after the second week and persisted through the ninth week(2). After the thirteenth week, no benzanthrone could be detected. The authors suggested that benzanthrone was possibly a degradation product that was subsequently also degraded.

BENZANTHRONE WAS EXCRETED BY RABBITS PARTLY UNCHANGED (ABOUT 30%).

The lipid peroxidation potential of benzanthrone in different subcellular organelles of liver was examined to elucidate the basis of benzanthrone induced hepatotoxicity. Male Wistar albino rats were given an intraperitoneal injection of benzanthrone oat 40 mg/kg daily for 3 consecutive days. The animals were killed 24 hours after the last treatment. Livers were removed for the preparation of subcellular fractions. Hepatic homogenate and subcellular fractions from control and treated rats were assayed for lipid peroxidation by determining the formation of malonaldehyde. The subcellular fractions included cell debris, nucleus, mitochondria, microsome, and cytosol. Protein content was determined as well. Benzanthrone caused statistically significant enhancements in NADPH dependent enzymatic and nonenzymatic hepatic lipid peroxidation in whole homogenate, nuclear, mitochondrial, and microsomal fractions. Benzanthrone induced a significant increase of 212 and 68% in the mitochondrial and microsomal fractions, respectively. A significant increase of 116, 91, and 67% in whole homogenate, mitochondrial, and microsomal fractions was induced by benzanthrone on prooxidant free nonenzymatic lipid peroxidation. Benzanthrone significantly enhanced prooxidant free FeSO4/ADP and ascorbate mediated nonenzymatic lipid peroxidation in hepatic in Fe(+2)/ADP and ascorbate dependent lipid peroxidation was also evident in the nuclear fraction. Increased production of lipid peroxides in nuclear, mitochondrial, and microsomal fractions suggested that these membranes were the vulnerable sites for benzanthrone induced toxicity.

The bioelimination and organ retention of (14)C benzanthrone, an anthraquinone dye intermediate, were determined in rats, mice and guinea pigs. Urinary excretion of benzanthrone during 96 hours was higher in guinea pigs (28%) compared with rats and mice (19%). However, fecal elimination during 96 hours was higher in rats (39%) and mice (42%) than in guinea pigs (25%). Urinary elimination of benzanthrone in rats and mice was highest between 12 and 24 hours. The maximum amount of radiolabelled benzanthrone was eliminated through feces at 24-48 hours in all the three animal species. The retention of (14)C benzanthrone in the liver was comparable in rats (11.2%) and mice (11.9%), while in guinea pigs it was substantially higher (21.9%). The testes of rats and mice were devoid of radioactivity, whereas those of guinea pigs showed a marginal retention (1.25%) of (14)C. The present study suggests that guinea pigs are more prone to benzanthrone toxicity than are rats and mice since the bioelimination of this compound is slower and its organ retention is higher in this species.

Used in the manufacture of dyes; [Merck Index] Has been found in the atmosphere in an aluminum plant and is one of the most common chemicals detected at superfund sites; [HSDB]

IN MFR OF DYES

...BY HEATING REDUCTION PRODUCT OF ANTHRAQUINONE WITH SULFURIC ACID & GLYCEROL.

(A) FROM ANTHRANOL & GLYCEROL BY CONDENSATION BY MEANS OF SULFURIC ACID (ANTHRANOL IS MADE FROM ANTHRAQUINONE); (B) FROM ANTHRACENE IN SULFURIC ACID SOLN BY ADDITION OF GLYCEROL & HEATING TO 100-110 °C UNTIL ANTHRACENE DISAPPEARS. REACTION MASS IS THEN DILUTED WITH WATER, SALTED OUT & PURIFIED.

7H-Benz[de]anthracen-7-one: ACTIVE

METHOD OF PURIFICATION: CRYSTALLIZATION FROM TOLUENE.

Benzanthrone is the starting product for an important group of vat dyes. Fusion of benzanthrone with potassium hydroxide produces dibenzanthrone (violanthrone). Dyes produced from violanthrone include Vat Green B (also known as Indanthrene Black BB), Vat Jade Green, Vat Olive Green B, Vat Olive T, and Indanthrene Brilliant Violet 2R. Benzanthrone and its derivatives are used as light sensitizers for degradation of plastics, daytime fluorescent pigments, and in colored chemical smokes, too.

Vat dyes derived from benzanthrone can be subdivided into two major groups: the peri ring-closure products of 3-anthraquinonylaminobenzanthrone, referred to as "imide-green" dyes, and the dyes of the violanthrone and the isoviolanthrone series. These include C.I. Vat Green 3 (CAS No. 3271-76-9), C.I. Vat Black 25 (CAS No. 4395-53-5), C.I. Vat Blue 25 (CAS No. 6247-39-8), C.I. Vat Blue 20 (CAS No. 116-71-2), C.I. Vat Green 1 (CAS No. 128-58-5), C.I. Vat Violet 1 (CAS No. 1324-55-6), and C.I. Vat Blue 26 (CAS No. 4430-55-1).