naphthalene

naphthalene

naphthalene (năfˈthəlēnˌ), colorless, crystalline, solid aromatic hydrocarbon with a pungent odor. It melts at 80℃, boils at 218℃, and sublimes upon heating. It is insoluble in water, somewhat soluble in ethanol, soluble in benzene, and very soluble in ether, chloroform, or carbon disulfide. Naphthalene is obtained from coal tar, a byproduct of the coking of coal. It is used in mothballs and gives them their characteristic odor. From it are prepared derivatives that are used in the preparation of dyes and as insecticides and organic solvents. The molecular structure of naphthalene is that of two benzene rings fused together with two adjacent carbon atoms common to both rings.

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The following article is from The Great Soviet Encyclopedia (1979). It might be outdated or ideologically biased.

Naphthalene

 

an aromatic hydrocarbon; colorless lamellar crystals with a characteristic odor. Melting point, 80.3°C; boiling point, 218°C; density, 1.1517 g/cm³ (15°C).

Naphthalene is volatile; it sublimes at 50°C. It is poorly soluble in water but dissolves readily in most organic solvents; it is distilled over steam. In general, naphthalene is prepared commercially from coal tar (8–10 percent naphthalene content) and from products of petroleum pyrolysis; naphthalene extracted from the latter is considerably purer than that derived from coal tar.

Naphthalene readily enters into elecrophilic substitution reactions (for example, halogenation, nitration, sulfonation, alkylation, and acylation). The substitution rate in the α-position is higher than in the β-position, although β-substituted naphthalenes have greater thermodynamic stability than α-substituted forms. Therefore, mixtures of isomers are usually produced; their composition depends on the reagent, catalyst, and solvent used, and also on the temperature and reaction time. For example, both α-chloronaphthalene and 1,4- and 1,5-dichloronaphthalenes are produced upon cold chlorination of naphthalene in the presence of FeCl_3. The reaction of naphthalene and acetyl chloride in ethylene dichloride upon action of AlCl_3. produces α-acetylnaphthalene; a mixture of α- and β-derivatives is formed when no solvent is used. Sulfonation of naphthalene at low temperatures yields α-naphthalenesulfonic acid, which converts to the β-isomer upon heating. Further sulfonation produces a mixture of disulfonic and polysulfonic acids of naphthalene; this process yields no sulfonic acids containing sulfo groups in the ortho-, para-, and peri- (that is, 1,8 or 4,5) positions. Naphthalene nitration yields α-nitronaphthalene, and the β-isomer is obtained by an indirect method.

Hydrogenation of naphthalene yields Tetralin (I) and Decalin (II), whereas oxidation yields phthalic anhydride (III)—for example,

In industry, α-naphthylamine is prepared by reduction of α-nitronaphthalene, acid hydrolysis of α-naphthylamine yields α-naphthol, and alkaline fusion of β-naphthalenesulfonic acid produces β-naphthol:

Naphthalene is a valuable source material in the preparation of many organic intermediates (primarily phthalic anhydride) and dyes (based on naphthols, naphthylamines, and their sulfonic acids).

Methyl naphthalenes, the closest homologues of naphthalene, are also found in coal tar and have properties similar to those of naphthalenes. These homologues are used in the synthesis of plant growth regulators, whereas polymethyl naphthalenes are used as insecticides, and the sulfonic acid salts of higher naphthalene homologues are used as emulsifiers.

B. L. DIATKIN

The Great Soviet Encyclopedia, 3rd Edition (1970-1979). © 2010 The Gale Group, Inc. All rights reserved.

naphthalene

[′naf·thə‚lēn]

(organic chemistry)

C₁₀H₈ White, volatile crystals with coal tar aroma; insoluble in water, soluble in organic solvents; structurally it is represented as two benzenoid rings fused together; boiling point 218°C, melting point 80.1°C; used for moth repellents, fungicides, lubricants, and resins, and as a solvent. Also known as naphthalin; tar camphor.

McGraw-Hill Dictionary of Scientific & Technical Terms, 6E, Copyright © 2003 by The McGraw-Hill Companies, Inc.

naphthalene

, naphthaline, naphthalin

a white crystalline volatile solid with a characteristic penetrating odour: an aromatic hydrocarbon used in mothballs and in the manufacture of dyes, explosives, etc. Formula: C₁₀H₈

Collins Discovery Encyclopedia, 1st edition © HarperCollins Publishers 2005