Naphthalene

Napthalene has a bond, C-H C-H C
And on this bond it has a C, C=C-H H-C
With a C-H here and a C-H there
Here a C, there an H, everywhere a C-H
Naphthalene has a bond
C=C-C-H C
-- sung by tes to the tune of Old MacDonald during an organic chemistry final exam, December 16, 1997

Naphthalene (C₁₀H₈) is a white solid with a strong odor; it is commonly known as mothballs, moth flakes, or tar camphor. It is often used in the long term storage of clothes to prevent pests from invading, as pests avoid the strong odor of the chemical.

Naphthalene is back... in POG form!

Below is a drawing of the naphthalene molecule. Single lines represent single bonds, and double lines represent double bonds.

      H     H
      |     |
      C     C
     / \\  / \\
    /   \\/   \\
H--C     C     C--H
   ||    |     |
   ||    |     |
H--C     C     C--H
    \   //\   //
     \ //  \ //
      C     C
      |     |
      H     H

Properties of Naphthalene

Molecular Weight; 128.16
Boiling Point: 218 C (424 F)
Melting Point: 80 C (176 F)
Specific Gravity: 1.2
Vapor Density (air = 1): 4.4
Solubility in water: Insoluble

Toxicity of Naphthalene

Naphthalene in a highly pure form is rather toxic and should not be ingested. Naphthalene can irritate the skin and, on prolonged contact, may cause rashes. It also causes severe eye watering and irritation. If ingested, it can cause a headache, a great deal of perspiration, listlessness, dark urine, nausea, vomiting, and disorientation can occur, and if ingested in large amounts, it can bring on a coma or even death due to renal failure.

Reactivity of Naphthalene

Naphthalene is fairly reactive; you need to keep it in a sealed container to prevent the substance from subliming. If heated, the substance will produce a significant amount of carbon dioxide and carbon mononxide gas. However, it will not produce hazardous polymers; it usually reacts with other carbon rings to form longer carbon chains or fullerenes.

Making Naphthalene

It is very difficult to make naphthalene with a high purity in the home, but it is quite easy to make a substance with a strong trace amount of naphthalene.

Simply take a piece of wood and burn it over an open flame, collecting the ash produced. The produced ash will contain a mishmash of large organic molecules, but one of the most common molecules in the substance will be naphthalene. It is one of the smallest molecules that will be found in the ash.

Another simple way to produce naphthalene is to smoke a cigarette; both the smoke and the ash contain significant amounts of naphthalene.

Common Applications of Naphthalene

Naphthalene is a fundamental part of our lives, whether we know it or not. For starters, it is a natural component of most fossil fuels such as petroleum and coal, so naphthalene plays an essential role in the heating of homes and transportation of people and goods. Whenever you turn on your home heater or start up your automobile (unless you are using alternative energy sources), you are utilizing naphthalene.

In manufacturing, naphthalene is used in the manufacture of resins, dyes, pharmaceuticals, insect repellents, leather tanning agents, and other materials. The strong odor that you smell whenever you use mothballs or apply insect repellent is largely due to the naphthalene content in the substance.

Naph"tha*lene (?), n. Chem.

A white crystalline aromatic hydrocarbon, C10H8, analogous to benzene, and obtained by the distillation of certain bituminous materials, such as the heavy oil of coal tar. It is the type and basis of a large number of derivatives among organic compounds. Formerly called also naphthaline.

Naphthalene red Chem., a dyestuff obtained from certain diazo derivatives of naphthylamine, and called also magdala red. -- Naphthalene yellow Chem., a yellow dyestuff obtained from certain nitro derivatives of naphthol.

© Webster 1913.