Naphthalene
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 | |
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Naphthalene[1] | |
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 | |
| CAS number | |
| PubChem | |
| 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 | |
| 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 ΔfH |
78.53 kJ/mol |
| Std enthalpy of combustion ΔcH |
-5156.3 kJ/mol |
| Standard molar entropy S |
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 |
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 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.
Naphthalene Media
Resonance structures of naphthalene
Alpha vs beta symmetry-equivalent positions
Structure of azulene
Naphthalene Crystals
Propranolol is a beta blocker.
References
- ↑ 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.
- ↑ "Thermal Conductivity of Naphthalene". DDBST GmbH. DDBST GmbH. Retrieved 2014-06-21.
- ↑ 3.0 3.1 "Ambient Water Quality Criteria for Naphthalene" (PDF). United States Environmental Protection Agency. 23 April 2014. Retrieved 2014-06-21.
- ↑ 4.0 4.1 4.2 Anatolievich, Kiper Ruslan. "naphthalene". chemister.ru. Retrieved 2014-06-21.
- ↑ 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.
- ↑ 6.0 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)
- ↑ "Dynamic Viscosity of Naphthalene". DDBST GmbH. DDBST GmbH. Retrieved 2014-06-21.
- ↑ 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 978-0-387-26147-8.
Other websites
- Naphthalene (PIM 363) - mostly on toxicity of naphthalene
