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Naphthalene
Naphthalene numbering.svg
Naphthalene-from-xtal-3D-balls.png
Naphthalene-from-xtal-3D-vdW.png
Naphthalene-xtal-3D-vdW-B.png
Other names white tar, camphor tar, tar camphor, naphthalin, naphthaline, antimite, albocarbon, hexalene, mothballs, moth flakes
Identifiers
CAS number 91-20-3
PubChem 931
EC number 214-552-7
KEGG C00829
ChEBI CHEBI:16482
RTECS number QJ0525000
SMILES c1ccc2ccccc2c1
Beilstein Reference 1421310
Gmelin Reference 3347
Properties
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)[3]
1.0253 g/cm3 (20 °C)
0.9625 g/cm3 (100 °C)[3]
Melting point

78.2 °C, 351 K, 173 °F

Boiling point

217.97 °C, 491 K, 424 °F

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)[4]
Solubility Soluble in alcohols, liquid ammonia, carboxylic acids, C6H6, SO2,[4] CCl4, CS2, toluene, aniline[5]
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)[5]
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)[5]
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)[5]
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)[5]
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)[5]
log P 3.34
Vapor pressure 8.64 Pa (20 °C)
23.6 Pa (30 °C)
0.93 kPa (80 °C)[4]
2.5 kPa (100 °C)[6]
kH 0.42438 L·atm/mol
-91.9·10−6 cm3/mol
Thermal conductivity 98 kPa:
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)[2]
Refractive index (nD) 1.5898
Viscosity 0.964 cP (80 °C)
0.761 cP (100 °C)
0.217 cP (150 °C)[7]
Structure
Crystal structure Monoclinic[8]
Space group P21/b[8]
C52h[8]
Lattice constant a = 8.235 Å, b = 6.003 Å, c = 8.658 Å[8]
Thermochemistry
Std enthalpy of
formation
ΔfHo298
78.53 kJ/mol
Std enthalpy of
combustion
ΔcHo298
-5156.3 kJ/mol
Standard molar
entropy
So298
167.39 J/mol·K[6]
Specific heat capacity, C 165.72 J/mol·K
Hazards
Main hazards Flammable, sensitizer, possible carcinogen. Dust can form explosive mixtures with air
NFPA 704

NFPA 704.svg

2
2
0
 
Explosive limits 5.9%
U.S. Permissible
exposure limit (PEL)
TWA 10 ppm (50 mg/m3)
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

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

  1. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 13, 35, 204, 207, 221–222, 302, 457, 461, 469, 601, 650. doi:10.1039/9781849733069-FP001 . ISBN 978-0-85404-182-4 . 
  2. "Thermal Conductivity of Naphthalene". DDBST GmbH. http://www.ddbst.com/en/EED/PCP/TCN_C123.php. Retrieved 2014-06-21. 
  3. 3.0 3.1 "Ambient Water Quality Criteria for Naphthalene". United States Environmental Protection Agency. http://water.epa.gov/scitech/swguidance/standards/upload/2001_10_12_criteria_ambientwqc_napthalene80.pdf. Retrieved 2014-06-21. 
  4. 4.0 4.1 4.2 Anatolievich, Kiper Ruslan. "naphthalene". http://chemister.ru/Database/properties-en.php?dbid=1&id=1005. Retrieved 2014-06-21. 
  5. 5.0 5.1 5.2 5.3 5.4 5.5 Seidell, Atherton; Linke, William F. (1919). Solubility of Inorganic and Organic Compounds (2nd ed.). New York: D. Van Nostrand Company. pp. 443–446. 
  6. 6.0 6.1 Naphthalene in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD), http://webbook.nist.gov (retrieved 2014-05-24)
  7. "Dynamic Viscosity of Naphthalene". DDBST GmbH. http://www.ddbst.com/en/EED/PCP/VIS_C123.php. Retrieved 2014-06-21. 
  8. 8.0 8.1 8.2 8.3 Douglas, Bodie E.; Ho, Shih-Ming (2007). Structure and Chemistry of Crystalline Solids. New York: Springer Science+Business Media, Inc.. p. 288. ISBN 0-387-26147-8 . https://books.google.com/books?id=hYRCAAAAQBAJ&pg=PA288. 

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