Naphthalene is an organic compound with formula C10H8.
Naphthalene is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass.
As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings.
Naphthalene is best known as the main ingredient of traditional mothballs.
Preferred IUPAC name: Naphthalene
Systematic IUPAC name: Bicyclo[4.4.0]deca-1,3,5,7,9-pentaene
Other names: white tar, camphor tar, tar camphor, naphthalin, naphthaline, antimite, albocarbon, hexalene, mothballs, moth flakes
CAS Number: 91-20-3
Chemical formula: C10H8
Molar mass: 128.174 g·mol−1
Appearance: White solid crystals/ flakes
Odor: Strong odor of coal tar
1.145 g/cm3 (15.5 °C)
1.0253 g/cm3 (20 °C)
0.9625 g/cm3 (100 °C)
Melting point: 78.2 °C (172.8 °F; 351.3 K)
80.26 °C (176.47 °F; 353.41 K)at 760 mmHg
Boiling point: 217.97 °C (424.35 °F; 491.12 K) at 760 mmHg
Solubility in water
19 mg/L (10 °C)
31.6 mg/L (25 °C)
43.9 mg/L (34.5 °C)
80.9 mg/L (50 °C)
238.1 mg/L (73.4 °C)
Soluble in alcohols, liquid ammonia, Carboxylic acids, C6H6, SO2, CCl4, CS2, toluene, aniline
Solubility in ethanol
5 g/100 g (0 °C)
11.3 g/100 g (25 °C)
19.5 g/100 g (40 °C)
179 g/100 g (70 °C)
Solubility in acetic acid
6.8 g/100 g (6.75 °C)
13.1 g/100 g (21.5 °C)
31.1 g/100 g (42.5 °C)
111 g/100 g (60 °C)
Solubility in chloroform
19.5 g/100 g (0 °C)
35.5 g/100 g (25 °C)
49.5 g/100 g (40 °C)
87.2 g/100 g (70 °C)
Solubility in hexane
5.5 g/100 g (0 °C)
17.5 g/100 g (25 °C)
30.8 g/100 g (40 °C)
78.8 g/100 g (70 °C)
Solubility in butyric acid
13.6 g/100 g (6.75 °C)
22.1 g/100 g (21.5 °C)
131.6 g/100 g (60 °C)
log P 3.34
8.64 Pa (20 °C)
23.6 Pa (30 °C)
0.93 kPa (80 °C)
2.5 kPa (100 °C)
Henry's law constant (kH): 0.42438 L·atm/mol
Magnetic susceptibility (χ): -91.9·10−6 cm3/mol
0.1219 W/m·K (372.22 K)
0.1174 W/m·K (400.22 K)
0.1152 W/m·K (418.37 K)
0.1052 W/m·K (479.72 K)
Refractive index (nD) : 1.5898
0.964 cP (80 °C)
0.761 cP (100 °C)
0.217 cP (150 °C)
Naphthalene can be produced from coal or petroleum. Production volume in the United States decreased significantly from a peak of 409.000 tons in 1968 to 101.000 tons in 1994.
Production capacity has remained relatively stable in recent years, with estimated capacity for 2004 at 97.700 tons.
The major commercial use of naphthalene is in the manufacture of polyvinyl chloride (PVC) plastics.
The major consumer products made from naphthalene are moth repellents, in the form of mothballs or crystals, and toilet deodorant blocks.
It is also used for making dyes, resins, leather tanning agents, and the insecticide carbaryl.
It enters the environment from industrial uses, from its use as a moth repellent, from the burning of wood or tobacco and from accidental spills.
Most of the naphthalene entering the environment is discharged to the air.
The largest releases result from the combustion of wood and fossil fuels and the naphthalene-containing moth repellents.
Smaller amounts of naphthalene are introduced to water as the result of discharges from coal-tar production and distillation processes.
In the atmosphere naphthalene is broken down rapidly, usually within one day.
From the atmosphere it can also very slowly be depositioned in water.
It has a low water solubility of 31,7 µg/l and a rather low tendency to adsorb to particles.
It is expected that only 10% of the naphthalene in water bodies is associated with particles.
The main loss of naphthalene from water water bodies is by evaporation into the atmosphere.
Naphthalene has a very low potential towards bioaccumulation, and will be rapidly eliminated from vertebrates.
Therefore naphtalene is not expected to biomagnify through food chains.
Concentrations above 1 mg/l can cause acute toxicity to some species of fish, crustaceans and zooplankton
White, crystalline flakes with a strong Mothball odor.
Naphthalene is derived from coal tar.
It consists of two aromatic rings attached on one side. Naphthalene was formerly used as a dusting powder, Insecticide, Fungicide, and moth repellent.
It is not recommended for general use as an insecticide because it may recrystallize on specimens and can discolor wool in the presence of moisture.
Additionally, its actual effectiveness against insects is questionable.
It is used industrially as an intermediate in making dyes, explosives, and synthetic resins. Naphthalene can sublime at room temperature.
naphthalin; naphthene; tar camphor; mothballs; moth crystals; white tar; Moth Flakes; Naphthalin (Deut.); naftalina (Esp.); naphtalène (Fr.); naftalene (It.); naftaleen (Ned.); naftalen (Pol., Sven.)
Naphthalene [ACD/Index Name] [ACD/IUPAC Name] [Wiki]
MFCD00001742 [MDL number]
Naphtalène [French] [ACD/IUPAC Name]
Naphthalin [German] [ACD/IUPAC Name]
Ναφθαλίνιο [Modern Greek (1453-)]
Naphthalene is the simplest polyaromatic hydrocarbon (PAH) consisting of two fused benzene rings.
It has a distinct, pungent odor that can be detected at levels as low as 0.08 ppm.
Naphthalene is the most abundant single component of coal tar so most of it is now industrially derived from coal tar.
From the 1960s until the 1990s, significant amounts of naphthalene were also produced from heavy petroleum fractions during petroleum refining, but today petroleum-derived naphthalene represents only a minor component of naphthalene production.
Naphthalene is also produced naturally with trace amounts of naphthalene being produced by black walnuts, magnolias and specific types of deer, as well as the Formosan subterranean termite.
Some strains of the endophytic fungus (Muscodor albus) also produce naphthalene. Naphthalene and other polycyclic aromatic hydrocarbons (PAHs) are released from incomplete combustion processes originating in industry, cigarette smoke and motor vehicle exhaust, as well as natural events such as forest fires.
Industrially, naphthalene is used in the production of phthalic anhydride, as a solvent for chemical reactions, as a wetting agent and as a fumigant.
It is also used in pyrotechnic special effects such as the generation of black smoke and simulated explosions.
In the past, naphthalene was administered orally to kill parasitic worms in livestock.
Naphthalene was once the primary ingredient in mothballs, though its use has largely been replaced in favor of alternatives such as 1,4-dichlorobenzene.
In a sealed container containing naphthalene pellets, naphthalene vapors build up to levels that are toxic to both the adult and larval forms of many moths.
Naphthalene has been shown to exhibit apoptotic and catabolic functions (4, 5).
Exposure to large amounts of naphthalene may damage or destroy red blood cells.
Humans, in particular children, have developed this condition, known as hemolytic anemia, after ingesting mothballs or deodorant blocks containing naphthalene.
Naphthalene Zone Refined (number of passes:23)
white tar, camphor tar, naphthalin, naphthaline, antimite, albocarbon, hexalene, mothballs, moth flakes