Naphthalic anhydride
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Naphthalic anhydride
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CAS No:
81-84-5
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Formula:
C12H6O3
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Chemical Name:
Naphthalic anhydride
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Synonyms:
1H,3H-Naphtho[1,8-cd]pyran-1,3-dione;Naphthalic anhydride;1,8-Naphthalic anhydride;Protect (agrochemical);1,8-Naphthalenedicarboxylic acid anhydride;1,8-Naphthalic acid anhydride;1,8-Naphthalenedicarboxylic anhydride;Protect;1,8-Naphthoic anhydride;NSC 5747;1,8-Naphthanoic anhydride;Naphthalene-2,6-dicarboxylic acid anhydride
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CAS No:
Naphthalic anhydride Basic Attributes
198.17
198.17
153190
201-380-2
32RS852X55
5747
DTXSID4026505
Light tan crystalline solid|Needles in alcohol
29173980
Characteristics
43.4
3.24 (est)
Beige to light brown Powder
1.5±0.1 g/cm3
270 °C
407.5±14.0 °C at 760 mmHg
272 °C
1.712
Decomposes in water
Store below +30°C.
4.12X10-7 mm Hg at 25 deg C (est)
Oral-Rat LD50: 12340 mg/kg
Inflammable in case of fire, high temperature and oxidant
Henry's Law constant = 6.2X10-7 atm-cu m/mole at 25 °C (est)
Hydroxy radical reaction rate constant = 8.3X10-12 cu cm/molec-sec at 25 °C (est)
Safety Information
NONH for all modes of transport
2
36/37/38
26-37/39-24/25
QK5350000
Xi
Treasury is ventilated, low temperature and dry; stored separately from oxidant
Stable under normal storage conditions; non-hygroscopic.
P261-P305 + P351 + P338
H315-H319-H335
|Warning|H315 (34.81%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 142 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
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).
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).
Toxicity
practically nontoxic
LD50 Rabbit dermal >2025 mg/kg|LD50 Rat (female) ip 480 mg/kg /from table/|LD50 Rat (male) ip 230 mg/kg /from table/|LD50 Mouse (male) ip 250 mg/kg /from table/|For more Non-Human Toxicity Values (Complete) data for NAPHTHALIC ANHYDRIDE (6 total), please visit the HSDB record page.
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.
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).
The rate constant for the vapor-phase reaction of naphthalic anhydride with photochemically-produced hydroxyl radicals has been estimated as 8.3X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 15.5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Hydrolysis of the anhydride to form the naphthalene 1,8 dicarboxylic acid is expected to be an important fate process(2). Naphthalic anhydride absorbs light at wavelengths >290 nm(3) and therefore is expected to be susceptible to direct photolysis by sunlight; however, the rate of this reaction is not known(SRC).
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).
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.
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).
Occupational exposure to napthalic anhydride may occur through dermal contact with this compound at workplaces where naphthalic anhydride is produced or used. Monitoring data indicate that the general population may be exposed to naphthalic anhydride via inhalation of ambient air where this compound has been detected in the fine particle organics. (SRC)
Drug Information
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
/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.
1,8-naphthalenedicarboxylic acid anhydride
Naphthalic anhydride Use and Manufacturing
Industrial acenaphthene is vaporized with primary air, mixed with secondary air, oxidized to 1, 8-naphthalenedicarboxylic acid anhydride with cobalt as a catalyst, and then cooled. Raw material consumption quota: industrial acenaphthene 1430-1500kg/t.
As an important raw material for the synthesis of perylene dyes, pigments and optical brighteners
Lubricants and lubricant additives
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
Technical /grade/ is > or = 98% pure.|Discontinued products: Protect
All other petroleum and coal products manufacturing|1H,3H-Naphtho[1,8-cd]pyran-1,3-dione: ACTIVE
Computed Properties
Molecular Weight:198.17
XLogP3:2.3
Hydrogen Bond Acceptor Count:3
Exact Mass:198.031694049
Monoisotopic Mass:198.031694049
Topological Polar Surface Area:43.4
Heavy Atom Count:15
Complexity:282
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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