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Naphthalene numbering.svg
IUPAC name Bicyclo[4.4.0]deca-1,3,5,7,9-pentene
Other names white tar, camphor tar, tar camphor, naphthalin, naphthaline, antimite, albocarbon, hexalene, mothballs, moth flakes
Molecular formula C10H8
Molar mass 128.17 g mol-1
Appearance White solid crystals/ flakes
Odor Strong odor of coal tar
Density 1.145 g/cm3 (15.5 °C)[1]
1.0253 g/cm3 (20 °C)[2]
0.9625 g/cm3 (100 °C)[1]
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)[2]
238.1 mg/L (73.4 °C)[3]
Solubility 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)[4]
EU classification Template:Hazchem Xn Dangerous for the Environment (Nature) N
Main hazards Flammable, sensitizer, possible carcinogen. Dust can form explosive mixtures with air
NFPA 704

NFPA 704.svg

R-phrases R22, R40, R50/53
S-phrases Template:S2, S36/37, Template:S46, S60, S61
Explosive limits 5.9%[5]
U.S. Permissible
exposure limit (PEL)
TWA 10 ppm (50 mg/m3)[6]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Naphthalene is a crystalline, white hydrocarbon, with a strong smell. It is best known as the main ingredient in mothballs, urinal deodorizer blocks, and can be used as an antiseptic. In mothballs, it is used as an insecticide or pesticide.

Naphthalene is toxic. In humans, being exposed to naphthalene can destroy red blood cells. Naphthalene may also cause cancer.

History[change | change source]

In the early 1820s, two different papers are published on something that matches the description of Naphthalene. Both groups made it by distilling coal tar. In 1821 John Kidd cited both reports, and condensed their results to accurately describe the properties of naphthalene, and how to make it. Kidd named it naphthalene because "naphtha"  means any explosive hydrocarbon mixture. By 1826, Michael Faraday discovered the formula for it. Emil Erlenmeyer proposes that it is two fused benzene rings in 1866, and Carl Gräbe confirms this three years later.

References[change | change source]

  1. 1.0 1.1 "Ambient Water Quality Criteria for Naphthalene" (PDF). United States Environmental Protection Agency. Retrieved 2014-06-21. 
  2. 2.0 2.1 Cite error: Invalid <ref> tag; no text was provided for refs named crc.
  3. Anatolievich, Kiper Ruslan. "naphthalene". Retrieved 2014-06-21. 
  4. Seidell, Atherton; Linke, William F. (1919). Solubilities of Inorganic and Organic Compounds (2nd ed.). New York: D. Van Nostrand Company. pp. 443–446. 
  5. Cite error: Invalid <ref> tag; no text was provided for refs named sigma.
  6. Cite error: Invalid <ref> tag; no text was provided for refs named PGCH.

Other websites[change | change source]