Cairo University
Faculty of Engineering
Chemical Engineering Department
Organig chemistry
Naphthalene
Cairo University
Faculty of Engineering
Chemical Engineering Department
Organig chemistry
Naphthalene
1-Afaf Hassanien
2-Ragaa Ramadan
3-Mervat Samy
4-Patricia Ernest
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 What is Naphthalene?
Naphthalene (also known as naphthalin, naphthaline, moth ball, tar
camphor, white tar, or albocarbon).Naphthalene is an organic compound
with formula C10H8. It is a white crystalline solid with a characteristic odor.
As an aromatic hydrocarbon, naphthalene's structure consists of a fused
pair of benzene rings. It is best known as the traditional ingredient(s) of
mothballs.
 History
In 1819–1820, at least two chemists reported a white solid with a pungent
odor derived from the distillation of coal tar.
In 1821, John Kidd described many of this substance's properties and the
means of its production, and proposed the name naphthalene, as it had
been derived from a kind of naphtha.
In 1826, Naphthalene's chemical formula was determined by Michael
Faraday.
In 1866, the structure of two fused benzene rings was proposed by Emil
Erlenmeyer, and confirmed by Carl Gräbe three years later.
 Properties
Molecular formula : C10H8
Molar mass
: 128.17052g/mol
Appearance
: White solid crystals/flakes,
Density
: 1.14 g/cm³
Melting point
: 81.2 °C
Boiling point
: 218 °C
Solubility
: Insoluble in wate
 production
Most naphthalene is derived from coal tar. From the 1960s until the 1990s,
significant amounts of naphthalene were also produced from heavy
petroleum fractions during petroleum refining, but today petroleum-derived
naphthalene represents only a minor component of naphthalene
production. Naphthalene is the most abundant single component of coal
tar. Although the composition of coal tar varies with the coal from which it
is produced, typical coal tar is about 10% naphthalene by weight. In
industrial practice, distillation of coal tar yields an oil containing about 50%
naphthalene, along with a variety of other aromatic compounds. This oil,
after being washed with aqueous sodium hydroxide to remove acidic
components (chiefly various phenols), and with sulfuric acid to remove
basic components, undergoes fractional distillation to isolate naphthalene.
The crude naphthalene resulting from this process is about 95%
naphthalene by weight, often referred to as 78°C (melting point).
 Uses
1- Naphthalene is used in explosives.
2- As a fumigant
The most familiar use of naphthalene is as a household fumigant, such as
in mothballs although 1,4-dichlorobenzene (or p-dichlorobenzene) is now
more widely used. In a sealed container containing naphthalene pellets,
naphthalene vapors build up to levels toxic to both the adult and larval
forms of many moths that attack textiles. Other fumigant uses of
naphthalene include use in soil as a fumigant pesticide, in attic spaces to
repel animals and insects, and in museum storage-drawers and cupboards
to protect the contents from attack by insect pests.
3- Naphthalene is used in engineering to study heat transfer
using mass sublimation.
4- It`s used in tanning leather applications, insecticide,
antiseptic, lubricant, dye, resin, solvents, and plastics.
 Health effects
Exposure to large amounts of naphthalene may damage or destroy
red blood cells. Humans, particularly children, have developed this
condition, known as hemolytic anemia, after ingesting mothballs or
deodorant blocks containing naphthalene. Symptoms include
fatigue, lack of appetite, restlessness, and pale skin. Exposure to
large amounts of naphthalene may cause confusion, nausea,
vomiting, diarrhea; blood in the urine .The International Agency for
Research on Cancer classifies naphthalene as possibly carcinogenic
to humans and animals.
 References
1- McMurry, John. 2004. Organic Chemistry, 6th ed. Belmont, CA:
Brooks/Cole.
2- Morrison, Robert T. and Robert N. Boyd. 1992. Organic
Chemistry, 6th ed. Englewood Cliffs, NJ: Prentice Hall.
3- Solomons, T.W. Graham and Craig B. Fryhle. 2004. Organic
Chemistry, 8th ed. Hoboken, NJ: John Wiley