naphthalene

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naphthalene

(năf`thəlēn'), colorless, crystalline, solid aromatic hydrocarbon with a pungent odor. It melts at 80°C;, boils at 218°C;, 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 benzenebenzene
, colorless, flammable, toxic liquid with a pleasant aromatic odor. It boils at 80.1°C; and solidifies at 5.5°C;. Benzene is a hydrocarbon, with formula C6H6.
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 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 It might be outdated or ideologically biased.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 FeCl3. The reaction of naphthalene and acetyl chloride in ethylene dichloride upon action of AlCl3. 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
References in periodicals archive ?
Cakmak, Synthetic route to 1,3-disubstituted naphthalene derivatives, J Chem Res-S, 524 (2002).
Chlorinated naphthalenes. Geneva: The Organization; 2001.
Polychlorinated naphthalenes: An environmental update.
In Biluo Co oil shale samples, 38 aromatic hydrocarbon compositions were detected, dominated by the following seven series: naphthalene (N), methylnaphthalene (MN), dimethynaphthalene (DMN), trimethynaphthalene (TMN), tetramethynaphthalene (TeMN), pentamethylnaphthalene (PMN) and ethylnaphthalene (EN).
The compounds mainly fall into the following 12 aromatic hydrocarbon series: naphthalene (m/z 128, m/z 142, m/z 156, m/z 170, m/z 184, m/z 198), phenanthrene (m/z 178, m/z 192, m/z 206, m/z 220), benzopyrene (m/z 252), fluoranthene (m/z 202, m/z 216), dibenzothiophene (m/z 184, m/z 198, m/z 212, m/z 226), benzonaphthothiophene (m/z 234), dibenzofuran (m/z 168, m/z 182, m/z 196), fluorene (m/z 166, m/z 180, m/z 194), chrysene (m/z 228, m/z 242, m/z 256), biphenyl (m/z 154, m/z 168, m/z 182), triaromatic sterane (m/z 231) and benzohopane (m/z 191).
The concentration of aromatic compounds, such as naphthalenes, phenanthrenes, dibenzothiophenes and their structural isomers are at present attracting increasing attention as maturity indicators for coals and shale source rocks.
Failure to consider the cancer risk from naphthalene. Naphthalene was one of' the most Frequently detected PAHs in Gulf seafood tested after the spill and vas the most prevalent PAH in the oil itself (FDA 201Oa; FDA, unpublished data).
From analyzing my oily rock samples, I know that naphthalene concentrations within the beached Cosco Busan oil decreased dramatically during the initial days after the spill and are still decreasing slowly in later samples.
Although a roller bioreactor limited stripping losses and was observed to be a workable design for naphthalene bioremediation (Purwaningsih et al., 2004), mass transfer rates that were two orders of magnitude less than those observed in a CSTR severely limited the rate at which naphthalene could be bioremediated from polluted water.
Key Players Mentioned in the Global Naphthalene and PCE based Admixtures Market Research Report:
Concretes with sulfonated naphthalene polymer-based SP1 and second-generation polycarboxylic ether-based SP3 exhibited better hardened performances in comparison with the concretes with other types of chemical admixture.