6370. Naphthalene

Nomenclature

CAS number: 91-20-3
Naphthalin; naphthene; tar camphor.
C10H8; mol wt 128.17.
C 93.71%, H 6.29%.

Description and references

Major constituent of coal tar. Dry coal tar contains about 11%. Crystallizes from the middle or “carbolic oil” fraction of the distilled tar. Purified by hot pressing, which may be followed by washing with H2SO4, NaOH, and water, then by fractional distillation or by sublimation. Manuf: Faith, Keyes & Clark's Industrial Chemicals, F. A. Lowenheim, M. K. Moran, Eds. (Wiley-Interscience, New York, 4th ed., 1975) pp 556-562. Review: R. M. Gaydos in Kirk-Othmer Encyclopedia of Chemical Technology vol. 15 (Wiley-Interscience, New York, 3rd ed., 1981) pp 698-719. Review of toxicology and human exposure: Toxicological Profile for Naphthalene, 1-Methylnaphthalene, and 2-Methylnaphthalene (PB2006-100004, 2005) 347 pp.

Chemical structure

Properties

Monoclinic prismatic plates from ether or by sublimation; also sold as white scales, powder, balls, or cakes, mp 80.2°. Odor of moth balls. Volatilizes appreciably at room temp. d420 1.162. d4100 0.9628. Sublimes appreciably at temps above mp; volatile with steam. bp760 217.9°; bp400 193.2°; bp200 167.7°; bp100 145.5°; bp60 130.2°; bp40 119.3°; bp20 101.7°; bp10 85.8°. Flash pt, open cup 174°F (79°C); closed cup 190°F (88°C). Autoignition temp 1053°F (567°C). nD100 1.58212. Purple fluorescence in Hg light (petr ether soln). Ultraviolet absorption: Several characteristic bands between 217.5 and 320 nm in hexane. Insol in water. One gram dissolves in 13 ml methanol or ethanol, in 3.5 ml benzene or toluene, in 8 ml olive oil or turpentine, in 2 ml chloroform or carbon tetrachloride, in 1.2 ml carbon disulfide. Very sol in ether, hydronaphthalenes, in fixed and volatile oils.

Caution

Potential symptoms of overexposure are eye irritation; corneal damage, optical neuritis; dermatitis; headache, confusion, excitement, malaise; nausea, vomiting, abdominal pain; bladder irritation; profuse sweating; acute intravascular hemolysis, anemia, leukocytosis, fever; jaundice; hematuria, hemoglobinuria, renal shutdown. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 220; Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 4th ed., 1984) Section III, pp 307-311. This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-177.

Use

Manuf phthalic and anthranilic acids which are used in making indigo, indanthrene, and triphenylmethane dyes. Manuf of hydroxyl (naphthols), amino (naphthylamines), sulfonic acid and similar compds used in the dye industries. Manuf of synthetic resins, celluloid, lampblack, smokeless powder. Manuf of hydronaphthalenes (Tetralin, Decalin) which are used as solvents, in lubricants, and in motor fuels. Moth repellent and insecticide.

Therapeutic Category

Has been used as antiseptic (topical and intestinal); anthelmintic (Cestodes).

Therapeutic Category (Veterinary)

Has been used in dusting powders, as an insecticide and internally as an intestinal antiseptic and vermicide.

Keywords

Anthelmintic (Cestodes)