Naphthalin-1,8-dicarbonsureanhydrid

Light tan crystalline solid

Needles in alcohol

Slightly sol in acetic acid; very soluble in ether and alcohol.

Practically insoluble in water

272 °C

272 degree C (open cup)

Dry Powder

Light tan solid; [HSDB] Tan powder; Decomposed by water; [MSDSonline]

This chemical does not meet GHS hazard criteria for 4.3% (7 of 161) of reports.

Warning

H315 (30.4%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 161 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Chemical: 1H,3H-Naphtho[1,8-cd]pyran-1,3-dione

1H,3H-Naphtho[1,8-cd]pyran-1,3-dione is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1H,3H-Naphtho[1,8-cd]pyran-1,3-dione 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: 12-05-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/33522

1H,3H-Naphtho1,8-cdpyran-1,3-dione: Does not have an individual approval but may be used under an appropriate group standard

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Naphthalenedicarboxylic anhydride is included on this list.

LC50 Leuciscus idus (fresh water fish) 380 mg/L/28 hr (static)

LD50 Quail oral 4100 mg/kg bw

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from a structure estimation method(2), indicates that naphthalic anhydride is not expected to have high mobility in soil(SRC). Volatilization of naphthalic anhydride from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.2X10-7 atm-cu m/mole(SRC), determined using a fragment constant estimation method(3). Naphthalic anhydride is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.1X10-7 mm Hg(SRC), determined from a fragment constant method(4). Napthalic anhydride is formed by the degradation of acenaphthylene-1,2-dione. Degradation studies showed 50% degradation of naphthalic anhydride after 29 days using a pilot-scale bioslurry treatment(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from a structure estimation method(2), indicates that naphthalic anhydride is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant of 6.2X10-7 atm-cu m/mole(SRC), determined using a fragment constant estimation method(3). According to a classification scheme(4), an estimated BCF of 63(SRC), from an estimated log Kow of 3.24(5) indicates the potential for bioconcentration in aquatic organisms is moderate. Hydrolysis of the anhydride to form the naphthalene 1,8 dicarboxylic acid is expected to be an important fate process(6). Napthalic anhydride is formed by the degradation of acenaphthylene-1,2-dione. Degradation studies of a mixture of acenaphthylene-1,2-dione and naphthalic anhydride showed 50% degradation of naphthalic anhydride after 29 days using a pilot-scale bioslurry treatment(7). This indicates that biodegradation in water may be an important fate process(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), naphthalic anhydride, which has an estimated vapor pressure of 4.1X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase naphthalic anhydride 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 15.5 hours(SRC), calculated from its rate constant of 8.3X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase naphthalic anhydride may be removed from the air by wet and dry deposition(SRC). Naphthalic anhydride absorbs light at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight; however, the rate of this reaction is not known(SRC).

Water samples obtained from effluent of four urban and four rural sites in AL, FL, GA, and MS during April, July, and October of 1999, and January of 2000 were collected and analyzed(1). Naphthalic anhydride was detected in all 8 samples with concentrations ranging from 0.02-0.13 ng/cu m(1).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of naphthalic anhydride can be estimated to be 120(SRC). According to a classification scheme(2), this estimated Koc value suggests that naphthalic anhydride is expected to have high mobility in soil.

URBAN/SUBURBAN: Smog from Los Angles, CA was analyzed for poly aromatic hydrocarbons on September 8-9, 1993. Naphthalic anhydride was found in the fine particle organics at 0.41 ng/cu m(1). Monitoring data from Houston, TX indicate that the average concentration of naphthalic anhydride in the ambient atmosphere during fall of 1990 was 224-50.9 pg/cu m(2). Total concentration of vapor plus particulate phase concentrations of naphthalic anhydride ranged from 1,343-391 pg/cu m with the highest concentration in the fall and the lowest in the spring(2). Air samples collected from Boston, MA contained 1.766 ng/cu m naphthalic anhydride(3). Naphthalic anhydride was found in the air of all 12 Southern California sites tested during a children's health study in concentrations ranging from 0.03-0.894 ng/cu m(4).

INDOOR: Naphthalic anhydride was found in the air of homes during a study in the winter of 1986-1987(1). The concentration of naphthalic anhydride ranged from 1.7-4.9 ug/cu m. This value was independent of number of smokers in the house hold as well as methods used to heat and cook in the house(1).

SOURCE DOMINATED: Naphthalic anhydride was detected, not quantified, in heavy duty diesel exhaust particulates(1).

/OTHER TOXICITY INFORMATION/ In a plant for the production of 1,8-naphthalic anhydride a total of 61 workers were employed in the period from 1963 to 1993. The workers were under the company physician's medical supervision. They were not observed to develop any diseases with a causal relation to 1,8-naphthalic anhydride exposure. Reports from another company's occupational medicine and healthcare protection department stated that no cases of respiratory tract or skin sensitization had been observed in connection with the handling of 1,8-naphthalic anhydride.

Naphthalic anhydride's former production and use in the US as a seed protectant(1) is expected to have resulted in its direct release to the environment(SRC). Naphthalic anhydride's production and use as an intermediate in the manufacture of imides and imines(2,3) may result in its release to the environment through various waste streams.

AEROBIC: Soil samples were collected during a pilot-scale bioslurry treatment of soil from a former gasworks site in Stockholm, Sweden, operated from 1893 to 1972. Naphthalic anhydride was identified, not quantified in the soil slurry which was incubated in the reactor for 29 days at 27 °C with an oxygen concentration of 6 mg/L. Samples were taken on days 3, 7, 24, and 29. Degradation results showed 85, 66, 84, and 50% degradation, respectively. However, another compound present in the slurry, acenaphthylene-1,2-dione, was shown to degrade to naphthalic anhydride during the GC analysis(1).

An estimated BCF of 63 was calculated for naphthalic anhydride(SRC), using an estimated log Kow of 3.24(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC), provided the compound is not metabolized by the organism(SRC).

The Henry's Law constant for naphthalic anhydride is estimated as 6.2X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant(SRC). Naphthalic anhydride's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Naphthalic anhydride is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.1X10-7 mm Hg(SRC), determined from a fragment constant method(3).

/LABORATORY ANIMALS: Acute Exposure/ The skin sensitization potential of 1,8-naphthalic anhydride (purity of the test substance 99.06%) was assessed in 20 male Dunkin-Hartley guinea pigs... .The control group consisted of 10 male animals and was treated with the formulating agent, Alembicol D, a product of coconut oil. Intradermal induction using an 0.1% formulation accompanied by simultaneous intradermal administration of Freund's complete adjuvant was followed after 1 wk by a 48 hr occlusive dermal induction using a 50% formulation( minimum irritancy formulation). Dermal challenge, which followed 14 days after the second induction treatment, was accomplished by application under occlusive cover of a 5% formulation to an anterior site on the flank of each guinea pig and similar treatment was carried out by applying a 10% formulation (maximum non-irritant concentration) to a posterior site on the animal's flank for 24 hours. This challenge led to a clear positive skin reaction in 16 of the 20 animals and produced a questionable positive skin reaction in 1 of the 20 animals. 1,8-Naphthalic anhydride thus exhibited a skin sensitizing potential in the test.

/LABORATORY ANIMALS: Acute Exposure/ Inhalation of the dust by rats for 4 hr at 820 mg/cu m air revealed no toxic symptom.

/LABORATORY ANIMALS: Acute Exposure/ /In acute studies/... lethargy, weakness, piloerection, decreased respiratory rate, increased salivation, ptosis, tremors, diarrhea, increased diuresis, blood in the urine and other signs of toxicity have been described . The post-mortems conducted after oral administration of lethal doses revealed slight hemorrhage of the lungs and discoloration of the liver, the spleen and the kidneys. Post-mortems on the surviving animals killed at the end of the 14 day observation period yielded no appreciable findings.

/LABORATORY ANIMALS: Acute Exposure/ The irritant effect of 1,8-naphthalic anhydride (purity not specified) on the skin was studied in the abraded dorsal skin of rabbits using the patch test... . Each of 6 rabbits were treated with 500 mg of the test substance (in 0.5 mL of distilled water) for 24 hours by means of application under occlusive cover to the intact and the scarified skin (application area approx 2.5 cm X 2.5 cm). The findings obtained immediately upon removal of the dressing and in the observation period of 48 hours did not reveal any signs of irritation, and 1,8-naphthalic anhydride was classified as not irritating to the skin of the rabbit.

For more Non-Human Toxicity Excerpts (Complete) data for NAPHTHALIC ANHYDRIDE (13 total), please visit the HSDB record page.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Naphthalenedicarboxylic anhydride is included on this list.

Used as a seed protectant and to make dyestuffs and optical brighteners; [HSDB]

Seed protectant /Former, US/

Dyestuffs, organic synthesis in general.

Intermediate used in the manufacture of imides and imide derivatives, in particular imidazole dyestuffs and optical brighteners... .

2023: 500,000 - <1,000,000 lb

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

(1986) >1M-10M lbs

(1990) >1M-10M lbs

(1994) >1M-10M lbs

(1998) >1M-10M lbs

... Made by the liquid-phase oxidation of acenaphthene with chromic acid in aqueous sulfuric acid or acetic acid. A post-oxidation of the crude oxidation product with hydrogen peroxide or an alkali hypochlorite is advantageous. An alternative liquid-phase oxidation process involves the reaction of acenaphthene, molten or in alkanoic acid solvent, with oxygen or acid at about 70-200 °C in the presence of Mn resinate or stearate or Co or Mn salts and a bromide. Addition of an aliphatic anhydride accelerates the oxidation. The anhydride of 1,8-naphthalenedicarboxylic acid is obtained in about 95-116 wt % yield by the vapor-phase air-oxidation of acenaphthene at about 330-450 °C, using unsupported or supported vanadium oxide catalysts, with or without modifiers.

Technical /grade/ is > or = 98% pure.

Discontinued products: Protect

Synthetic Dye and Pigment Manufacturing

1H,3H-Naphtho[1,8-cd]pyran-1,3-dione: ACTIVE