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.

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

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.

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
References in periodicals archive ?
In this case, however, it was found that growth on naphthalene could not induce the bioremediation of 1,5-dimethylnaphthalene.
The batch growth kinetics on naphthalene and 2-methylnaphthalene were simulated using first order growth kinetics assuming that PAHs were the limiting substrates.
Changes in the dissolved naphthalene concentration were due to particle dissolution adding to the naphthalene concentration in the water and utilization of naphthalene by the microorganisms:
p] is the substrate particle concentration (mg/l), S is the dissolved naphthalene concentration (mg/L), X is the bacteria concentration (mg dry weight/l), [micro]M is the maximum specific growth rate ([h.
Table 2 summarizes the maximum removal rates of both naphthalene and 2-methylnaphthalene in all bioremediation runs.
Due to its greater capacity for aqueous media, the baffled rotating bioreactor appears to be an optimum design for hydrophobic particles with bioremediation rates reaching as high as 61 mg/l-h for naphthalene (based on working volume of the bioreactor) and 30 mg/l-h for 2-methylnaphthalene.
Karegoudar, "Enhanced Degradation Rate of Naphthalene by Immobilization of Pseudomonas sp Strain NGK 1 in Polyurethane Foam," Appl.
Voice, "Comparison of Biodegradation Kinetic Parameters for Naphthalene in Batch and Sand Column Systems by Pseudomonas putida," Env.
Ethoxyresorufin O-deethylase (EROD) and aryl hydrocarbon hydroxylase (AHH)-inducing potency and lethality of chlorinated naphthalenes in chicken (Gallus domesticus) and eider duck (Somateria mollissima) embryos.
Swedish dioxin survey: determination of 2,3,7,8-TCDD toxic equivalent factors for some polychlorinated biphenyls and naphthalenes using biological tests.
In this study, we treated pregnant rats with 1,2,3,4,6,7-hexachlorinated naphthalene (1,2,3,4,6,7-HxCN) and examined the effects on the reproductive system of their male offspring at various phases of sexual maturation.
Polychlorinated naphthalene exposures and liver function changes.