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Naphthalene

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Naphthalene
Skeletal formula and numbering system of naphthalene
Skeletal formula and numbering system of naphthalene
Ball-and-stick model of naphthalene
Ball-and-stick model of naphthalene
Spacefill model of naphthalene
Unit cells of naphthalene
Names
Preferred IUPAC name
Naphthalene[1]
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
Identifiers
  • 91-20-3 checkY
3D model (JSmol)
Beilstein Reference 1421310
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.863
EC Number
  • 214-552-7
Gmelin Reference 3347
KEGG
RTECS number
  • QJ0525000
UNII
  • c1ccc2ccccc2c1
Properties
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)[2]
1.0253 g/cm3 (20 °C)
0.9625 g/cm3 (100 °C)[2]
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[2]
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)[3]
Solubility Soluble in alcohols, liquid ammonia, carboxylic acids, C6H6, SO2,[3] CCl4, CS2, toluene, aniline[4]
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)[4]
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)[4]
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)[4]
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)[4]
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)[4]
log P 3.34
Vapor pressure 8.64 Pa (20 °C)
23.6 Pa (30 °C)
0.93 kPa (80 °C)[3]
2.5 kPa (100 °C)[5]
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)[6]
1.5898
Viscosity 0.964 cP (80 °C)
0.761 cP (100 °C)
0.217 cP (150 °C)[7]
Structure
Monoclinic[8]
P21/b[8]
C5
2h[8]
a = 8.235 Å

, b = 6.003 Å

, c = 8.658 Å[8]
α = 90°, β = 122.92°, γ = 90°


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[5]
Specific heat capacity, C 165.72 J/mol·K
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Flammable, sensitizer, possible carcinogen. Dust can form explosive mixtures with air
GHS labelling:
Template:GHS02Template:GHS07Template:GHS08Template:GHS09[9]
Danger
H228, H302, H351, H410
P210, P273, P281, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Flash point 80 °C (176 °F; 353 K)
525 °C (977 °F; 798 K)
Explosive limits 5.9%
10 ppm[10] (TWA), 15 ppm[10] (STEL)
Lethal dose or concentration (LD, LC):
1800 mg/kg (rat, oral)
490 mg/kg (rat, oral)
1200 mg/kg (guinea pig, oral)
533 mg/kg (mouse, oral)[11]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 10 ppm (50 mg/m3)
REL (Recommended)
 TWA 10 ppm (50 mg/m3) ST 15 ppm (75 mg/m3)
IDLH (Immediate danger)
 250 ppm[12]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 were published on something that matched 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

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  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. 1 2 3 "Ambient Water Quality Criteria for Naphthalene" (PDF). United States Environmental Protection Agency. 23 April 2014. Archived from the original (PDF) on 2015-11-06. Retrieved 2014-06-21.
  3. 1 2 3 Anatolievich, Kiper Ruslan. "naphthalene". chemister.ru. Archived from the original on 2014-12-22. Retrieved 2014-06-21.
  4. 1 2 3 4 5 6 Seidell, Atherton; Linke, William F. (1919). Solubility of Inorganic and Organic Compounds (2nd ed.). New York: D. Van Nostrand Company. pp. 443–446.
  5. 1 2 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)
  6. ↑ "Thermal Conductivity of Naphthalene". DDBST GmbH. Archived from the original on 2016-03-04. Retrieved 2014-06-21.
  7. ↑ "Dynamic Viscosity of Naphthalene". DDBST GmbH. Archived from the original on 2016-03-04. Retrieved 2014-06-21.
  8. 1 2 3 4 Douglas, Bodie E.; Ho, Shih-Ming (2007). Structure and Chemistry of Crystalline Solids. New York: Springer Science+Business Media, Inc. p. 288. ISBN 978-0-387-26147-8.
  9. ↑ Sigma-Aldrich Co., Naphthalene. Retrieved on 2014-06-21.
  10. 1 2 Template:CRC90
  11. ↑ "Naphthalene". Immediately Dangerous to Life or Health Concentrations. National Institute for Occupational Safety and Health.
  12. ↑ NIOSH Pocket Guide to Chemical Hazards. "#0439". National Institute for Occupational Safety and Health (NIOSH).

Other websites

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